US3480377A - Solvent dyeing of living human hair - Google Patents
Solvent dyeing of living human hair Download PDFInfo
- Publication number
- US3480377A US3480377A US451642A US3480377DA US3480377A US 3480377 A US3480377 A US 3480377A US 451642 A US451642 A US 451642A US 3480377D A US3480377D A US 3480377DA US 3480377 A US3480377 A US 3480377A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- dye
- acid
- solvent
- blue
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004043 dyeing Methods 0.000 title description 57
- 239000002904 solvent Substances 0.000 title description 32
- 210000004209 hair Anatomy 0.000 title description 21
- 239000000975 dye Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 33
- 150000001491 aromatic compounds Chemical class 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- -1 aliphatic alcohols Chemical class 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 235000019445 benzyl alcohol Nutrition 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 6
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- GTKIEPUIFBBXJQ-UHFFFAOYSA-M sodium;2-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]-5-methylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GTKIEPUIFBBXJQ-UHFFFAOYSA-M 0.000 description 6
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 3
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 3
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005844 Thymol Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940051250 hexylene glycol Drugs 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229960000790 thymol Drugs 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- 229940099540 acid violet 43 Drugs 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 239000000982 direct dye Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 2
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- AMMWFYKTZVIRFN-UHFFFAOYSA-N sodium 3-hydroxy-4-[(1-hydroxynaphthalen-2-yl)diazenyl]-7-nitronaphthalene-1-sulfonic acid Chemical compound [Na+].C1=CC=CC2=C(O)C(N=NC3=C4C=CC(=CC4=C(C=C3O)S(O)(=O)=O)[N+]([O-])=O)=CC=C21 AMMWFYKTZVIRFN-UHFFFAOYSA-N 0.000 description 2
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FKVXIGHJGBQFIH-UHFFFAOYSA-K trisodium 5-amino-3-[[4-[4-[(7-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C=C4C=CC(=CC4=C3[O-])N)S(=O)(=O)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)[O-])N)[O-].[Na+].[Na+].[Na+] FKVXIGHJGBQFIH-UHFFFAOYSA-K 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 description 1
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 1
- DHTGRDDBCWWKQJ-UHFFFAOYSA-N 2-(2,2-dihydroxyethoxy)ethane-1,1-diol Chemical compound OC(O)COCC(O)O DHTGRDDBCWWKQJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical compound ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- QFVHZQCOUORWEI-UHFFFAOYSA-N 4-[(4-anilino-5-sulfonaphthalen-1-yl)diazenyl]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1N=NC(C1=CC=CC(=C11)S(O)(=O)=O)=CC=C1NC1=CC=CC=C1 QFVHZQCOUORWEI-UHFFFAOYSA-N 0.000 description 1
- YBUXKQSCKVQATK-UHFFFAOYSA-N 4-amino-n-phenylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1 YBUXKQSCKVQATK-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- HOWITLLZNKSJOJ-UHFFFAOYSA-M chembl471028 Chemical compound [Na+].C1=CC=CC2=C(O)C(N=NC3=C4C=CC=CC4=C(C=C3O)S([O-])(=O)=O)=CC=C21 HOWITLLZNKSJOJ-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- AOMZHDJXSYHPKS-UHFFFAOYSA-L disodium 4-amino-5-hydroxy-3-[(4-nitrophenyl)diazenyl]-6-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC=CC=3)C(O)=C2C(N)=C1N=NC1=CC=C([N+]([O-])=O)C=C1 AOMZHDJXSYHPKS-UHFFFAOYSA-L 0.000 description 1
- LARMRMCFZNGNNX-UHFFFAOYSA-L disodium 7-anilino-3-[[4-[(2,4-dimethyl-6-sulfonatophenyl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].[Na+].COc1cc(N=Nc2c(C)cc(C)cc2S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O LARMRMCFZNGNNX-UHFFFAOYSA-L 0.000 description 1
- UHXQPQCJDDSMCB-UHFFFAOYSA-L disodium;3-[[9,10-dioxo-4-(2,4,6-trimethyl-3-sulfonatoanilino)anthracen-1-yl]amino]-2,4,6-trimethylbenzenesulfonate Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C(S([O-])(=O)=O)=C1C UHXQPQCJDDSMCB-UHFFFAOYSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- QVBODZPPYSSMEL-UHFFFAOYSA-N dodecyl sulfate;2-hydroxyethylazanium Chemical compound NCCO.CCCCCCCCCCCCOS(O)(=O)=O QVBODZPPYSSMEL-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005209 naphthoic acids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LCUPSBNRQZFCAC-UHFFFAOYSA-N nitro N-oxosulfamate Chemical compound [O-][N+](=O)OS(=O)(=O)N=O LCUPSBNRQZFCAC-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- VRDAELYOGRCZQD-NFLRKZIHSA-M sodium;4-[(2z)-2-[(5e)-5-[(2,4-dimethylphenyl)hydrazinylidene]-4,6-dioxocyclohex-2-en-1-ylidene]hydrazinyl]benzenesulfonate Chemical compound [Na+].CC1=CC(C)=CC=C1N\N=C(/C(=O)C=C\1)C(=O)C/1=N\NC1=CC=C(S([O-])(=O)=O)C=C1 VRDAELYOGRCZQD-NFLRKZIHSA-M 0.000 description 1
- FHIODWDKXMVJGO-UHFFFAOYSA-N sodium;8-anilino-5-[[4-[(5-sulfonaphthalen-1-yl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonic acid Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC(C1=CC=CC(=C11)S(O)(=O)=O)=CC=C1NC1=CC=CC=C1 FHIODWDKXMVJGO-UHFFFAOYSA-N 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
- D06P1/628—Compounds containing nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/6422—Compounds containing nitro or nitroso groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6491—(Thio)urea or (cyclic) derivatives
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65112—Compounds containing aldehyde or ketone groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/653—Nitrogen-free carboxylic acids or their salts
- D06P1/6536—Aromatic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/922—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents hydrocarbons
- D06P1/924—Halogenated hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/90—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof
- D06P1/92—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dyes dissolved in organic solvents or aqueous emulsions thereof in organic solvents
- D06P1/928—Solvents other than hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Definitions
- This invention relates to dyeing.
- Organic compounds which may be used in the process include: aliphatic alcohols, for example n-butyl alcohol and amyl 'alcohol; aromatic hydroxy compounds, for example benzyl alcohol; esters, for example amyl lactate; aldehydes; ketones; and aromatic hydrocarbons.
- British patent specification 872,506 describes a dyeing process similar to that described in the above specification although in specification 872,506 the treatment is applied to leather, skins and/or animal fibers attached thereto.
- the solvents that can be used are similar to those that can be used in the process of specification 856,381.
- British patent specifications 826,479 and 918,597 also describe a dyeing procedure similar to that described in patent specification 856,381, although in specifications 826,479 and 918,597 the process is applied to the dyeing of human hair.
- the solvents used in the hair dyeing process of these patents include aliphatic and aralkyl alcohols, for example amyl alcohol and benzyl alcohol, and esters, for example amyl lactate.
- British patent specification 840,904 describes a dyeing process similar to that described in British patent specification 826,479 although in this case the organic solvent must be one of a number of specified alcohols and it must be miscible with water in the proportion in which it is present.
- Alcohols for use in the process described in spec ification 840,904 include butyl alcohol; aralkanols, for example benzyl alcohol; and cycloaliphatic alcohols, for example cyclohexanol.
- British patent specification 979,405 discloses the use as solvents of certain urea derivatives which are liquid at the dyeing temperature.
- Benzyl alcohol as well as other slightly water miscible and .water immiscible solvents referred to in the above specifications increase the rate of dyeing of the fiber or other material treated. This effect is particularly useful in the dying of living human hair because it enables a good uptake of dye to be obtained even at the relatively low temperatures that have to be employed for such dyeing.
- British patent specification 669,192 which concerns the dyeing of furs and skins also disclosesa dyeing procedure in which an organic solvent for the dye is included in the dyeing composition.
- the solvent employed is a partially or completely Water miscible aliphatic low molecular alcohol, ketone or ester or mixture thereof.
- the dyeing composition described contains 10% or more of the solvent.
- the dyeing can be carried out at relatively low temperatures, for example between 20 and C.
- the solvents employed are ethyl alcohol, glycol, acetone and ethyl acetate.
- R represents a monovalent aliphatic or araliphatic hydrocarbon group containing not more than 8 carbon atoms and n is from 1 to 4.
- these solvents are 2-butoxyethanol and 2-[(beta-ethoxy)-ethoxy]-etha- 1101. The use of these solvents increases the rate of uptake of the dye on the hair and enables keratinous fibers, e.g. live hair, to be dyed at ambient temperatures.
- the present invention provides a dyeing composition which comprises an aqueous solution, suspension or dispersion of a dye and an organic solvent for the dye, the composition additionally comprising dissolved therein a solid aromatic compound so as to improve the rate of uptake of the dye on the material to be dyed.
- Dye is used in this paragraph and hereinafter to include direct dyestuffs, i.e. dyestuffs capable of being fixed directly and in the final shade by the product to be dyed, without it being necessary to interpose any chemical transformation, and water insoluble colored organic compounds.
- the invention also provides a process which comprises contacting the material to be dyed with a dyeing composition comprising an aqueous solution, suspension or dispersion of a dye and an organic solvent for the dye, which solvent is liquid under the conditions of dyeing, the dyeing composition additionally comprising a solid aromatic compound which acts to increase the rate-of uptake ofthe dye by the material contacted.
- a dyeing composition comprising an aqueous solution, suspension or dispersion of a dye and an organic solvent for the dye, which solvent is liquid under the conditions of dyeing, the dyeing composition additionally comprising a solid aromatic compound which acts to increase the rate-of uptake ofthe dye by the material contacted.
- the invention may be applied to the dyeing of the various materials mentioned in the prior patent specifications referred to.
- fibers these can either be in the natural state or Woven or otherwise made up into fabrics or garments.
- the invention is particularly applicable to the dyeing of keratinous fibers such as hair.
- the solid aromatic compounds effective as increasing the rate of uptake of the dye from dyeing compositions containing solvents are those containing an aromatic ring and at least one of the following groups as substituents of the ring: carboxylic acid, amide and substituted amide, hydroxyl and esters thereof, nitrile, aldehyde, ketone, halogen, amine, alkoxy, ureido, and aliphatic groups, for example saturated or unsaturated groups containing up to 6 carbon atoms, which aliphatic groups are themselves substituted by at least one hydroxyl or carboxyl group.
- the solid aromatic compound molecule may contain a phenyl or naphthyl ring.
- the classes of compounds from which the solid aromatic compound may be chosen include: carboxylic acids, e.g. benzoic, cinnamic, salicylic, hippuric, and naphthoic acids; monoand polyhydric phenols; and chloro benzenes.
- Examples of compounds containing more than one of the above substituent groups are o-anisaldehyde, o-amino phenol and p-chloro phenol.
- the substituent groups may be the same as in, for example, p-dichlorobenzene and o-dimethoxy benzene.
- Examples of compounds containing a substituted aliphatic group are methoxy phenyl acetic acid, p-nitro benzyl alcohol and cinnamic acid.
- the solid aromatic compound may comprise an unsubstituted hydrocarbon group attached to the aromatic ring.
- a group may be a phenyl group or an aliphatic group such as an alkyl or alkenyl group having up to 6 carbon atoms, for example.
- Other groups may be present, for example nitro, nitroso, sulphonic acid or substituted sulphonic acid groups.
- Examples of compounds having other substituents present are o-cresol, thymol, sulphanilic acid, rn-nitrobenzaldehyde, p-nitro-benzyl alcohol, sulphanilanilide, pnitrobenzyl alcohol and 2,4-dichloronitrobenzene.
- the optimum amount of the solid aromatic compound to be used will to some extent be dependent on the other components of the dyeing composition such as the dye and solvent. In most cases an amount of at least 0.5% by weight of the dyeing composition will be necessary to produce a significant increase in the dyeing effect. For the dyeing of hair usually amounts in the range 1 to give the best results. Amounts of the solid aromatic compound in excess of its solubility in the dyeing composition are not objectionable but do not give any significant advantage and usually such an excess will not be used.
- the solid aromatic compound used in this instance can have a melting point as low as 45 C., or even lower depending on the actual dyeing temperature used. Higher temperatures may be used in other dyeing treatments, for instance in wooldyeing, but then the range of solid aromatic compounds that can be used is smaller. Thus for W001 dyeing one employs solid aromatic compounds having a melting point above about 80 C. or in any event above the actual dyeing temperature used.
- dyes that can be used are reactive dyes which contain chromophoric groups linked to a reactive group such as monoor di-chlorotriazine, dior tri-chloropyrimidine or vinyl sulphone.
- Reactive dyes free from a sulphonic or non-chelated carboxylic acid group such as described in British patent specification 953,230 can also be used.
- Neolan Black 2R 15691 Acid Black 43 Mordant dyes e.g.:
- Solochrome Black 6RN 14640 Mordant Black 3 Acid Alizarine Black N 15690 Mordant Black 15 Solochrome Black F 26695 Mordant Black 5 Disperse dyes, e.g.:
- Celliton Blue B 61500 Disperse Blue 14
- Celliton Fast Blue FFB 62050 Disperse Blue 6
- Celliton Blue 36 64505 Disperse Blue 31
- Direct dyes e.g.:
- aliphatic alcohols e.g. those containing 1-6 carbon atoms
- aralkanols e.g. benzyl alcohol
- alkoxy alcohols e.g. 3-methoxybutanol, ethoxyethanol and methoxyethanol;
- aliphatic ketones e.g. ethyl methyl ketone and methyl isobutyl ketone
- higher glycols e.g. hexylene glycol
- aliphatic esters e.g. amyl lactate
- Carbitols are monoethers and monoesters of dihydroxyethyl ether.
- the dyeing composition may also contain further ingredients known in the art.
- thickeners such as acetic or lactic acid.
- surface active agents such as acetic or lactic acid.
- aliphatic acids such as acetic or lactic acid.
- solvent is not miscible with water, a liquid miscible with both the water and solvent.
- the material to be dyed is contacted successively with an aqueous solution or dispersion of the dye and also with a liquid organic solvent for the dye (either the said solution or solvent being applied first), the solid aromatic compound being dissolved in either the aqueous solution or in the organic solvent or in both of them.
- the material to be dyed is contacted successively with a solution of the dye in a liquid organic solvent for the dye and also with water (either the organic solvent or the water being applied first), the solid aromatic compound being dissolved in either the organic solvent or in the water or in both of them.
- the dyeing compositions employed in the following examples each comprised an organic solvent, a solid aromatic compound (in solution in the composition), 1% dye, 1% monoethanolamine lauryl sulphate and the balance water.
- the pH of the dyeing composition in each case was about 4.
- the dye in each of Examples 1 to 34 was the acid dye Solway Purple R 125 (C.I. 60730 Acid Violet 43).
- Example 1 to 26 the amount of the solvent was in Examples 27-30, 5%; and in Examples 31-34, In Examples 1 to 9 the concentration of the solid aromatic compound was 2% and in Examples 10-34, 3%.
- Cinnamic acid Methoxy phenyl-acetic acid. Salicylic acid.
- Example 35 to 40 the composition employed was the same as that in Example 27 except that the dye employed was Coomassie Dark Blue BL (CI. 50330 Acid Blue 61) and instead of benzyl alcohol the solvent was as set out in Table 11.
- the dye employed was Coomassie Dark Blue BL (CI. 50330 Acid Blue 61) and instead of benzyl alcohol the solvent was as set out in Table 11.
- Example 42 to 52 the composition employed was the same as that in Example 31 except that the dye employed was as indicated in Table HI.
- Coomassie Violet 212s I 45190 Solvent Violet Switches of human hair were dyed with each of the compositions ofithe above examples by immersing the switches for 10 minutes in the dyeing compositions at 25 C. They were then washed with water and dried. Switches of hair" were also treated in a similar manner with the corresponding compositions from which the solid aromatic compound had been omitted. In every case the intensity of the color of the hair was noticeably greater in the case of dyeings with the compositions set out in the tables than with those compositions from which the solid organic compounds had been omitted.
- Examples 53 to 55 materials other than human hair were dyed.
- the dyeing composition used in each case consisted of Percent Monoethanolarnine lauryl sulphate 0.3 n-Propanol 15.0 Benzoic acid 3.0 Solway Purple R 1.0 Water to 100.0%.
- the fibers were dyed by immersing them for 10 minutes in the dyeing composition at 25 C. They were then washed with water and dried. The intensity of color of the dyed fibers was in each case greater than that obtained using dyeing compositions of the same pH but containing no benzoic acid or containing in place of the npropanol and benzoic acid, 6% of benzyl alcohol.
- a process for dyeing human hair attached to the head which comprises contacting the hair at a temperature below about 45 C. with an effective amount of a dyeing composition comprising an aqueous solution, suspension or dispersion of a direct dye and an organic solvent for the dye which solvent is liquid at the dyeing temperature and is selected from the group consisting of aliphatic alcohols, aralkanols, alkoxy alkanols, aliphatic ketones, hexylene glycol, aliphatic esters, tetraethyl urea and 2-(betaethoxy)-ethoxyethanol, the dyeing composition additionally comprising dissolved therein from about 1% to about 5% by weight of the composition of an aromatic compound which compound is solid at the dyeing temperature, acts to increase the rate of uptake of the dye by the hair and contains one phenyl or naphthyl ring.
- a dyeing composition comprising an aqueous solution, suspension or dispersion of a direct dye and an organic solvent for the dye
Description
United States Patent US. Cl. 8--10.1 4 Claims ABSTRACT OF THE DISCLOSURE A process for dyeing human hair which comprises contacting the hair with a dyeing composition comprising an aqueous solution, suspension or dispersion of a dye, an organic solvent for the dye, and a dissolved aromatic compound which is solid at the dyeing temperature and acts to increase the rate of uptake of the dye by the hair.
This invention relates to dyeing.
It is well known that the dyeing of a wide variety of materials by treatment with an aqueous solution, dispersion or suspension of a dye can be improved by including an organic solvent for the dye in the aqueous dyeing composition. 7
Thus, it is known from British patent specification 856,381 to include in the aqueous solution, dispersion or suspension of a dye with which keratinous fibers, such as silk and wool, orregenerated protein fibers are to be contacted to effect the dyeing thereof, an organic compound which is a solvent for the dye, and which is a liquid under the conditions of dyeing an insoluble or only slightly soluble in water, the solubility of the dye in the organic compound being greater than the solubility of the dye in water. Organic compounds (solvents) which may be used in the process include: aliphatic alcohols, for example n-butyl alcohol and amyl 'alcohol; aromatic hydroxy compounds, for example benzyl alcohol; esters, for example amyl lactate; aldehydes; ketones; and aromatic hydrocarbons.
British patent specification 872,506 describes a dyeing process similar to that described in the above specification although in specification 872,506 the treatment is applied to leather, skins and/or animal fibers attached thereto. The solvents that can be used are similar to those that can be used in the process of specification 856,381.
British patent specifications 826,479 and 918,597 also describe a dyeing procedure similar to that described in patent specification 856,381, although in specifications 826,479 and 918,597 the process is applied to the dyeing of human hair. The solvents used in the hair dyeing process of these patents include aliphatic and aralkyl alcohols, for example amyl alcohol and benzyl alcohol, and esters, for example amyl lactate.
British patent specification 840,904 describes a dyeing process similar to that described in British patent specification 826,479 although in this case the organic solvent must be one of a number of specified alcohols and it must be miscible with water in the proportion in which it is present. Alcohols for use in the process described in spec ification 840,904 include butyl alcohol; aralkanols, for example benzyl alcohol; and cycloaliphatic alcohols, for example cyclohexanol.
British patent specification 979,405 discloses the use as solvents of certain urea derivatives which are liquid at the dyeing temperature.
Benzyl alcohol as well as other slightly water miscible and .water immiscible solvents referred to in the above specifications increase the rate of dyeing of the fiber or other material treated. This effect is particularly useful in the dying of living human hair because it enables a good uptake of dye to be obtained even at the relatively low temperatures that have to be employed for such dyeing.
British patent specification 669,192 which concerns the dyeing of furs and skins also disclosesa dyeing procedure in which an organic solvent for the dye is included in the dyeing composition. In the procedure described in specification 669,192 the solvent employed is a partially or completely Water miscible aliphatic low molecular alcohol, ketone or ester or mixture thereof. The dyeing composition described contains 10% or more of the solvent. The dyeing can be carried out at relatively low temperatures, for example between 20 and C. Examples of the solvents employed are ethyl alcohol, glycol, acetone and ethyl acetate.
British patent specification 819,184 which relates to the dyeing of keratinous fibers, particularly hair, also describes the use of an organic solvent which is completely miscible with-the water in the proportion in which it is present. In this instance the solvent employed is one having the general formula:
.where R represents a monovalent aliphatic or araliphatic hydrocarbon group containing not more than 8 carbon atoms and n is from 1 to 4. Examples of these solvents are 2-butoxyethanol and 2-[(beta-ethoxy)-ethoxy]-etha- 1101. The use of these solvents increases the rate of uptake of the dye on the hair and enables keratinous fibers, e.g. live hair, to be dyed at ambient temperatures.
We have now discovered that the increase in the rate of dye uptake that results from the use of solvents as mentioned in the above specifications can be further improved by including dissolved in the dyeing composition a wide range of aromatic compounds which are solid at the dyeing temperature; such a compound will hereinafter be referred to as a solid aromatic compound.
Accordingly, the present invention provides a dyeing composition which comprises an aqueous solution, suspension or dispersion of a dye and an organic solvent for the dye, the composition additionally comprising dissolved therein a solid aromatic compound so as to improve the rate of uptake of the dye on the material to be dyed. Dye is used in this paragraph and hereinafter to include direct dyestuffs, i.e. dyestuffs capable of being fixed directly and in the final shade by the product to be dyed, without it being necessary to interpose any chemical transformation, and water insoluble colored organic compounds.
The invention also provides a process which comprises contacting the material to be dyed with a dyeing composition comprising an aqueous solution, suspension or dispersion of a dye and an organic solvent for the dye, which solvent is liquid under the conditions of dyeing, the dyeing composition additionally comprising a solid aromatic compound which acts to increase the rate-of uptake ofthe dye by the material contacted.
The invention may be applied to the dyeing of the various materials mentioned in the prior patent specifications referred to. In the case of fibers, these can either be in the natural state or Woven or otherwise made up into fabrics or garments. The invention is particularly applicable to the dyeing of keratinous fibers such as hair.
Experiments carried out have indicated that the solid aromatic compounds effective as increasing the rate of uptake of the dye from dyeing compositions containing solvents are those containing an aromatic ring and at least one of the following groups as substituents of the ring: carboxylic acid, amide and substituted amide, hydroxyl and esters thereof, nitrile, aldehyde, ketone, halogen, amine, alkoxy, ureido, and aliphatic groups, for example saturated or unsaturated groups containing up to 6 carbon atoms, which aliphatic groups are themselves substituted by at least one hydroxyl or carboxyl group.
The solid aromatic compound molecule may contain a phenyl or naphthyl ring.
The classes of compounds from which the solid aromatic compound may be chosen include: carboxylic acids, e.g. benzoic, cinnamic, salicylic, hippuric, and naphthoic acids; monoand polyhydric phenols; and chloro benzenes.
Examples of compounds containing more than one of the above substituent groups are o-anisaldehyde, o-amino phenol and p-chloro phenol. The substituent groups may be the same as in, for example, p-dichlorobenzene and o-dimethoxy benzene.
Examples of compounds containing a substituted aliphatic group are methoxy phenyl acetic acid, p-nitro benzyl alcohol and cinnamic acid.
The solid aromatic compound may comprise an unsubstituted hydrocarbon group attached to the aromatic ring. Such a group may be a phenyl group or an aliphatic group such as an alkyl or alkenyl group having up to 6 carbon atoms, for example. Other groups may be present, for example nitro, nitroso, sulphonic acid or substituted sulphonic acid groups.
Examples of compounds having other substituents present are o-cresol, thymol, sulphanilic acid, rn-nitrobenzaldehyde, p-nitro-benzyl alcohol, sulphanilanilide, pnitrobenzyl alcohol and 2,4-dichloronitrobenzene.
The optimum amount of the solid aromatic compound to be used will to some extent be dependent on the other components of the dyeing composition such as the dye and solvent. In most cases an amount of at least 0.5% by weight of the dyeing composition will be necessary to produce a significant increase in the dyeing effect. For the dyeing of hair usually amounts in the range 1 to give the best results. Amounts of the solid aromatic compound in excess of its solubility in the dyeing composition are not objectionable but do not give any significant advantage and usually such an excess will not be used.
As the dyeing of living hair is usually carried out below 45 C. the solid aromatic compound used in this instance can have a melting point as low as 45 C., or even lower depending on the actual dyeing temperature used. Higher temperatures may be used in other dyeing treatments, for instance in wooldyeing, but then the range of solid aromatic compounds that can be used is smaller. Thus for W001 dyeing one employs solid aromatic compounds having a melting point above about 80 C. or in any event above the actual dyeing temperature used.
As is known from the abovementioned specifications, a wide variety of dyes can be used in solvent-containing dye systems and those mentioned can be employed in performing this invention.
Among the dyes that can be used are reactive dyes which contain chromophoric groups linked to a reactive group such as monoor di-chlorotriazine, dior tri-chloropyrimidine or vinyl sulphone. Reactive dyes free from a sulphonic or non-chelated carboxylic acid group such as described in British patent specification 953,230 can also be used.
As examples of dyes which may be employed in carrying out this invention are mentioned the following- C.I. classification 13390 Acid Blue 92 19140 Acid Yellow 23 45190 Acid Violet 9 Solway Purple R 60730 Acid Violet 43 Brilliant Alizarine Milling Blue 61585 Acid Blue 80 Carbolan Violet 2RS 62165 Acid Violet 51 Carbolan Blue HR 62075 Acid Blue 138 Premetallized dyes:
Both 1:1 and 2:1 complexes e.g. Neolan Black 2R 15691 Acid Black 43 Mordant dyes, e.g.:
Solochrome Black 6RN 14640 Mordant Black 3 Acid Alizarine Black N 15690 Mordant Black 15 Solochrome Black F 26695 Mordant Black 5 Disperse dyes, e.g.:
Celliton Blue B 61500 Disperse Blue 14 Celliton Fast Blue FFB 62050 Disperse Blue 6 Celliton Blue 36 64505 Disperse Blue 31 Direct dyes, e.g.:
Melanthine BH 22590 Direct Blue 2 Diphenyl Fast Black B 27720 Direct Black 51 Diphenyl Brilliant Violet BC 27905 Direct Violet 51 Solvent dyes, e.g.:
Zapon Fast Violet R 15680 Coomassie Violet 2RS 45190 Solvent Violet 10 As will be seen from the above mentioned specifications, a large number of different solvents are known to be used in dyeing compositions and those mentioned can be used in carrying out this invention. Among the solvents which may be used in accordance with the present .invention are:
aliphatic alcohols, e.g. those containing 1-6 carbon atoms,
including cyclohexanol;
aralkanols, e.g. benzyl alcohol;
alkoxy alcohols e.g. 3-methoxybutanol, ethoxyethanol and methoxyethanol;
aliphatic ketones, e.g. ethyl methyl ketone and methyl isobutyl ketone; higher glycols, e.g. hexylene glycol; aliphatic esters, e.g. amyl lactate;
as well as ethanol 2-methoxyacetate, geraniol, Carbitols and digols, and tetraethyl urea. Carbitols are monoethers and monoesters of dihydroxyethyl ether.
As is known, the more miscible the solvent the greater the proportion that is to be used.
The dyeing composition may also contain further ingredients known in the art. For instance, in compositions intended for dyeing human hair there may be included thickeners, surface active agents or aliphatic acids, such as acetic or lactic acid. One may also include where the solvent is not miscible with water, a liquid miscible with both the water and solvent.
In a modification of the invention the material to be dyed is contacted successively with an aqueous solution or dispersion of the dye and also with a liquid organic solvent for the dye (either the said solution or solvent being applied first), the solid aromatic compound being dissolved in either the aqueous solution or in the organic solvent or in both of them.
In a further modification of the invention the material to be dyed is contacted successively with a solution of the dye in a liquid organic solvent for the dye and also with water (either the organic solvent or the water being applied first), the solid aromatic compound being dissolved in either the organic solvent or in the water or in both of them.
The following examples illustrate the invention. All percentages are by weight.
The dyeing compositions employed in the following examples each comprised an organic solvent, a solid aromatic compound (in solution in the composition), 1% dye, 1% monoethanolamine lauryl sulphate and the balance water. The pH of the dyeing composition in each case was about 4.
The dye in each of Examples 1 to 34 was the acid dye Solway Purple R 125 (C.I. 60730 Acid Violet 43).
In Examples 1 to 26 the amount of the solvent was in Examples 27-30, 5%; and in Examples 31-34, In Examples 1 to 9 the concentration of the solid aromatic compound was 2% and in Examples 10-34, 3%.
The solvent and solid aromatic compound used in Examples 1 to 34 are set out in Table I TABLE I Solid aromatic compound Benzolc acid.
Cinnamic acid. Methoxy phenyl-acetic acid. Salicylic acid.
p-Amino benzoic acid.
. Hippuric acid.
. Acetyl salicylic acid.
. Phthalic acid.
. Sulphanilic acid.
Solvent Resorciuol.
Hydroquinone.
. Thymol.
o-Amino phenol. p-Chloro phenol. p-Nitro-benzyl alcohol.
. Phenylurea.
...- m-Nitrobenzaldehyde. o-Anisaldehyde.
24dichloronitro benzene.
Benzyl alcohol- Benzoic acid. ....-do Salicylic acid.
-.. p-Amino benzoic acid.
-. Thymol. Benzoic acid. Salicylic acid. p-Aminobenzoic acid.
In Examples 35 to 40 the composition employed was the same as that in Example 27 except that the dye employed was Coomassie Dark Blue BL (CI. 50330 Acid Blue 61) and instead of benzyl alcohol the solvent was as set out in Table 11.
TABLE II Example: Solvent 35 Cyclohexanol. 36 3-methoxybutanol. 37 Ethyl methyl ketone. 38 Hexylene glycol. 39 Ethanol Z-methoxy acetate. 40 2-[( 8-ethoxy)-ethoxy]-ethanol.
41 Tetraethyl urea.
In Examples 42 to 52 the composition employed was the same as that in Example 31 except that the dye employed was as indicated in Table HI.
TABLE III Example Name of dye C.I. classification of dye 42 Coomassie Blue R.L 13390 Acid Blue 92. 43. Resorcine Brown 20170 Acid Orange 24. 44. Disulphine Blue 42045 Acid Blue 1. 45 Coomassie Voilet; 2R8 45100 Acid Violet 9. 46 Nigrosine 50420 Acid Black 2. 47 Neolan Black 2R 15691 Acid Black 43. 48.- Solochro'me Black GRN 14640 Mordant Black 3. 49. CellitonBiue B... 61500 Disperse Blue 14. 50- Melan thine BH.-. 22590 Direct Blue 2.
Coomassie Violet 212s I 45190 Solvent Violet Switches of human hair were dyed with each of the compositions ofithe above examples by immersing the switches for 10 minutes in the dyeing compositions at 25 C. They were then washed with water and dried. Switches of hair" were also treated in a similar manner with the corresponding compositions from which the solid aromatic compound had been omitted. In every case the intensity of the color of the hair was noticeably greater in the case of dyeings with the compositions set out in the tables than with those compositions from which the solid organic compounds had been omitted.
In Examples 53 to 55 materials other than human hair were dyed. The dyeing composition used in each case consisted of Percent Monoethanolarnine lauryl sulphate 0.3 n-Propanol 15.0 Benzoic acid 3.0 Solway Purple R 1.0 Water to 100.0%.
The materials used are indicated in Table IV.
The fibers were dyed by immersing them for 10 minutes in the dyeing composition at 25 C. They were then washed with water and dried. The intensity of color of the dyed fibers was in each case greater than that obtained using dyeing compositions of the same pH but containing no benzoic acid or containing in place of the npropanol and benzoic acid, 6% of benzyl alcohol.
What is claimed is:
1. A process for dyeing human hair attached to the head which comprises contacting the hair at a temperature below about 45 C. with an effective amount of a dyeing composition comprising an aqueous solution, suspension or dispersion of a direct dye and an organic solvent for the dye which solvent is liquid at the dyeing temperature and is selected from the group consisting of aliphatic alcohols, aralkanols, alkoxy alkanols, aliphatic ketones, hexylene glycol, aliphatic esters, tetraethyl urea and 2-(betaethoxy)-ethoxyethanol, the dyeing composition additionally comprising dissolved therein from about 1% to about 5% by weight of the composition of an aromatic compound which compound is solid at the dyeing temperature, acts to increase the rate of uptake of the dye by the hair and contains one phenyl or naphthyl ring.
2. A process as claimed in claim 1, in which the organic solvent is benzyl alcohol.
3. A process as claimed in claim 2, in which the aromatic compound is a carboxylic acid.
4. A process as claimed in claim 3, in which the carboxylic acid is benzoic acid.
(References on following page) References Cited FOREIGN PATENTS UNITED STATES PATENTS 918,597 2/1963 Great Britain. 12/1931 Kern et a1 X 1,227,621 3/1960 France. 1,296,934 5/1962 France.
1/1940 Krltchevsky 16788 1 I X 5 70,067 10/1958 France. 2/ 946 Heman (Addition to No. 1,138,955 11/1960 Bashford 1,159,331 2/1958 France.
5/1961 Seemuller 167-88 7/ 1965 Brechner 167-88 ALBERT T. MYERS, Primary Examiner 8/1965 Sherburne 10 v. c. CLARKE, Assistant Examiner 9/1965 Lecher et a1. 167-88 11/1967 Lerner et a1. 167-88
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB18932/64A GB1096943A (en) | 1964-05-06 | 1964-05-06 | Solvent assisted dyeing |
Publications (1)
Publication Number | Publication Date |
---|---|
US3480377A true US3480377A (en) | 1969-11-25 |
Family
ID=10120941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US451642A Expired - Lifetime US3480377A (en) | 1964-05-06 | 1965-04-28 | Solvent dyeing of living human hair |
Country Status (3)
Country | Link |
---|---|
US (1) | US3480377A (en) |
DE (1) | DE1519516A1 (en) |
GB (1) | GB1096943A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3619102A (en) * | 1967-06-09 | 1971-11-09 | Oreal | Dyeing keratinic fibers with aqueous solutions of direct dyes and organic solvents |
US3933422A (en) * | 1972-02-18 | 1976-01-20 | Avon Products, Inc. | Non-staining keratinic coloring product |
DE2836300A1 (en) * | 1977-08-19 | 1979-03-01 | Oreal | COLORANTS FOR KERATIN FIBERS |
US4145413A (en) * | 1977-08-15 | 1979-03-20 | The Gillette Company | Artificial skin darkening composition and method of using the same |
US4873079A (en) * | 1987-08-21 | 1989-10-10 | Clairol Incorporated | Hair coloring composition and its method of use |
US6440175B1 (en) * | 2001-06-28 | 2002-08-27 | Stanley, Iii Virgil E. | Hair coloring kit |
EP1555012A1 (en) * | 2004-01-10 | 2005-07-20 | Clariant GmbH | Hair dyeing composition containing anthraquinones |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3660015A (en) * | 1969-01-24 | 1972-05-02 | Hodogaya Chemical Co Ltd | Process for the dyeing of modified polyester fibers with basic dyes in the presence of aromatic carboxylic acids |
US3702229A (en) * | 1970-12-29 | 1972-11-07 | Ciba Geigy Corp | Printing of anionic dyes on polycarbon-amides of bis(para-aminocyclohexyl)methane and dodecanedioic acid |
US3700405A (en) * | 1970-12-29 | 1972-10-24 | Ciba Geigy Corp | Dyeing of polycarbonamides of bis(paraamino-cyclohexyl)methane and dodecanediodic acid with anionic dyes |
US8790623B2 (en) | 2005-01-18 | 2014-07-29 | Il'Oreal | Composition for treating keratin fibers, comprising at least one aromatic alcohol, at least one aromatic carboxylic acid, and at least one protecting agent |
FR2880801B1 (en) † | 2005-01-18 | 2008-12-19 | Oreal | COMPOSITION FOR TREATING KERATIN FIBERS COMPRISING AROMATIC ALCOHOL, AROMATIC CARBOXYLIC ACID AND PROTECTIVE AGENT |
FR2907005B1 (en) † | 2006-10-17 | 2009-04-24 | Oreal | USE OF ORCEIN FOR COLORING HUMAN HAIR |
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US3619102A (en) * | 1967-06-09 | 1971-11-09 | Oreal | Dyeing keratinic fibers with aqueous solutions of direct dyes and organic solvents |
US3933422A (en) * | 1972-02-18 | 1976-01-20 | Avon Products, Inc. | Non-staining keratinic coloring product |
US4145413A (en) * | 1977-08-15 | 1979-03-20 | The Gillette Company | Artificial skin darkening composition and method of using the same |
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US6440175B1 (en) * | 2001-06-28 | 2002-08-27 | Stanley, Iii Virgil E. | Hair coloring kit |
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Also Published As
Publication number | Publication date |
---|---|
GB1096943A (en) | 1967-12-29 |
DE1519516A1 (en) | 1970-01-15 |
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