US3451927A - Fabric conditioner - Google Patents

Fabric conditioner Download PDF

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US3451927A
US3451927A US468918A US3451927DA US3451927A US 3451927 A US3451927 A US 3451927A US 468918 A US468918 A US 468918A US 3451927D A US3451927D A US 3451927DA US 3451927 A US3451927 A US 3451927A
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water
composition
fabric
cationic
softening
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US468918A
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John Barry Tune
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Lever Brothers Co
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Lever Brothers Co
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402Amides imides, sulfamic acids
    • D06M13/432Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40Dyes ; Pigments
    • C11D3/42Brightening agents ; Blueing agents
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402Amides imides, sulfamic acids
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions

Definitions

  • the present invention relates to compositions for fabric conditioning. It relates particularly to fabric conditioning compositions which are suitable for use in a water rinse.
  • the compositions of the present invention provide both a softening effect and an antistatic finish.
  • the invention is concerned with a fabric conditioner composition which comprises a cationic softening agent and an alkyl ethanolamide.
  • the alkyl group has about 12-18 carbon atoms.
  • the cationic softening agent maybe a quaternary ammonium salt, imidaioline or hydrazine.
  • Suitable quaternary ammonium salts are those of formula wherein R is an aliphatic hydrocarbon group containing from 16-22 carbon atoms; R is an alkyl group containting from 1-3 carbon atoms, R is R or R and X is an anion, e.g. halide, sulphate, alkyl sulphate having 1-3 carbon atoms in the alkyl group, or acetate, and y is the valency of X.
  • the preferred cationic softening agent is di-(hardened tallow) dimethyl ammonium chloride.
  • alkyl ethanolamide class are relatively ineffective antistatic agents when used alone and especially at the low concentrations used in a rinse process, but we have found that, in combination with the cationic softening agent, particularly with the above-mentioned preferred cationic softener, an excellent antistatic effect is conferred on nylon. This effect is markedly better than that given by either the cationic softener alone or by an ethanolamide alone. It is preferred to use a mixture of tallow monoand di-ethanolamides.
  • Typical fabric conditioner compositions in accordance ice with the present invention contain from 1 to 10 parts by weight of fabric softening agent and from 1 to 10 parts by weight of tallow ethanolamide and may be formulated in any customary manner, for example, as aqueous emulsion concentrates having from 1 to 10 percent active fabric softener.
  • Table I shows that the greater antistatic effect of the cationic softener/ethanolamide mixture is not due to the greater content of active in this composition, since results 5 and 4 using products with softener alone and mixed ethanolamides alone, each with a total solid content equal to that of the preferred mixture, are inferior to result 3. Similar results are obtained when the mixture of tallow rnonoand diethanolamides is replaced by either the, monoor the diethnanolamide.
  • compositions of the present invention will be further described by way of the following examples.
  • compositions which comprise a cationic softening agent, an alkyl ethanolamide and an optical bridghtening agent of the 1,3-diphenyl pyrazoline class.
  • the optical brighteners used in the composition of the invention are (1-p-sulphoamidophenly)- 3-(p-chlorophenyl) A -pyrazoline (hereafter referred to as A) and 1-(p-methoxycarbonyl-phenyl)-3-(p-chloro phenyl) A -pyrazoline (hereafter referred to as B).
  • they may also provide optical brightening additional to that accruing from a wash cycle wherein a detergent containing an optical brightener was used.
  • the storage stability of the compositions can be determined by testing the nylon whitening effect of the composition immediately on preparation and after 3 months storage at 20 C. as follows: non-flourescent nylon is washed for 3 minutes at 45 C. in 0.4% fiuorescer-free commercial detergent, rinsed in water, and then for minutes at 40 C. in 0.15% concention of composition. 5 wash/rinse cycles were carried out, at a liquor/cloth ratio of 30/1 using distilled water. Results are tabulated below:
  • Example 4 The composition of Example 1 having 0.13% A or 0.13% B therein.
  • EXAMPLE 5 The composition of Example 2 having 0.20% A therein.
  • EXAMPLE 6 The composition of Example 3 having 0.13% A or 0.13% B therein.
  • Inorganic salts, perfume, colourants and ingredients which are similarly non-deleterious to the softening or fiuorescing activity can be included.
  • additives for the purpose of obtaining improved freeze-thaw characteristics e.g. ethylene glycol, polyethylene glycol and shortchain quaternary ammonium compounds, may be included.
  • the fabric conditioner is preferably made up as an aqueous dispersion by heating the mixed components at ca. C. and addition of water to The cooled product is thinned, if necessary, by addition of electrolyte, e.g. sodium carbonate with stirring.
  • the fabric conditioner may also be prepared in solid form by employing urea in place of the water. It is preferably employed at a concentration of 0. 1-0.5% by weight of conditioner in water. It can be applied to the fabric by immersing the fabric in a bath containing it. Other methods such as spraying or padding on may be employed.
  • the present invention is concerned also with the fabric so treated.
  • compositions according to this invention have the advantage of applicability to all the usual ingredients of the domestic wash and achieve softening and maintenance or enhancement of the whiteness level together with an antistatic finish where appropriate in a single rinse treatment.
  • a fabric softening composition for softening and rendering antistatic a textile fabric which consists essentially of a mixture of (i) 3.75% by weight of di-hardened tallow dimethyl ammonium chloride, and (ii) 2.25 by weight of tallow ethanolamide and 2.25% by weight of tallow diethanolamide, the balance of said composition consisting essentially of water.

Description

United States Patent 3,451,927 FABRIC CONDITIONER John Barry Tune, Higher Bebington, Cheshire, England, assignor to Lever Brothers Company, New York, N .Y.,
a corporation of Maine No Drawing. Filed July 1, 1965, Ser. No. 468,918 Int. Cl. D06m 13/40, 13/46 US. Cl. 252-8.75 2 Claims ABSTRACT OF THE DISCLOSURE The present invention relates to compositions for fabric conditioning. It relates particularly to fabric conditioning compositions which are suitable for use in a water rinse. The compositions of the present invention provide both a softening effect and an antistatic finish.
There are many compounds which are known to give a softening finish to fabrics. Of the many types commercially available, e.g. anionic, quaternary cationic, nonquaternary cationic or nonionic compounds, the cationic compounds are generally more substantive and the compositions of the present invention employ a known cationic softening agent.
It has been found, surprisingly, that the softening effect of the cationic agent is enhanced and considerably improved and an antistatic finish is achieved when the cationic softening agent is used in conjunction with an alkyl ethanolamide.
Accordingly, the invention is concerned with a fabric conditioner composition which comprises a cationic softening agent and an alkyl ethanolamide.
. Preferably the alkyl group has about 12-18 carbon atoms. v
The cationic softening agent maybe a quaternary ammonium salt, imidaioline or hydrazine. Suitable quaternary ammonium salts are those of formula wherein R is an aliphatic hydrocarbon group containing from 16-22 carbon atoms; R is an alkyl group containting from 1-3 carbon atoms, R is R or R and X is an anion, e.g. halide, sulphate, alkyl sulphate having 1-3 carbon atoms in the alkyl group, or acetate, and y is the valency of X.
The preferred cationic softening agent is di-(hardened tallow) dimethyl ammonium chloride.
Members of the alkyl ethanolamide class are relatively ineffective antistatic agents when used alone and especially at the low concentrations used in a rinse process, but we have found that, in combination with the cationic softening agent, particularly with the above-mentioned preferred cationic softener, an excellent antistatic effect is conferred on nylon. This effect is markedly better than that given by either the cationic softener alone or by an ethanolamide alone. It is preferred to use a mixture of tallow monoand di-ethanolamides.
Typical fabric conditioner compositions in accordance ice with the present invention contain from 1 to 10 parts by weight of fabric softening agent and from 1 to 10 parts by weight of tallow ethanolamide and may be formulated in any customary manner, for example, as aqueous emulsion concentrates having from 1 to 10 percent active fabric softener.
The enhanced antistatic effect referred to above is proven by the set of typical results, given in Table I, which were obtained by the following procedure: Woven nylon fabric was washed for 5 minutes at 45 C. in 0.2% commercial detergent and rinsed twice for 2 minutes in water. The wash and rinse procedure was repeated and the nylon finally rinsed for 3 minutes at 30 C. in 0.2% fabric conditioner having the effective ingredients detailed in Table I made up to 100% with water, at a liquor/cloth ratio of 60/1 in distilled water. The nylon was dried and its resistance measured with a Twenty Million Megohmmeter (E.I.L.) at 40% relative humidity.
Table I shows that the greater antistatic effect of the cationic softener/ethanolamide mixture is not due to the greater content of active in this composition, since results 5 and 4 using products with softener alone and mixed ethanolamides alone, each with a total solid content equal to that of the preferred mixture, are inferior to result 3. Similar results are obtained when the mixture of tallow rnonoand diethanolamides is replaced by either the, monoor the diethnanolamide.
TABLE I a (hardened Resistance tallow) X10- dimethyl ohms per ammo- Tallow Tallow square (2 nium ehtanoldiethanoldays after Composition No. chloride amide amide treatment) Nil 2. 25 2. 25 25 3. Nil Nil 50 3. 75 2. 25 2. 25 1: 0 Nil 4. 125 4. 125 25 8. 25 Nil Nil 11 50 Control (water only) That the ethanolamide improves the softening finish imparted by the cationic softener has been proven by the usual subjective appraisal test by an panel of women. Although this test is not an objective one, it is nevertheless an established and reliable procedure for determining the relative softness of treated fabrics. Testinghas shown that a composition containing cationic softener and alkyl ethanolamide gives appreciably greater softening than that of a product comprising the same concentration of the cationic softener only and to be significantly better than water alone.
The compositions of the present invention will be further described by way of the following examples.
EXAMPLE 1 Percent Di-(hardened tallow) dimethyl ammonium chlo- Water, up to nium methosulphate 4.5 Tallow ethanolamide 2.25 Tallow diethanolamide 2.25
Water, up to 100 The softening effect of a cationic softener in the rinsing of natural or synthetic fabric, particularly cotton, is sometimes accompanied by a reduction in the whiteness level of the fabric. It has now been found that this quench effect can be overcome by inclusion of a nonionic optical brightening agent of the 1,3-diphenyl pyrazoline class within the composition. Although there are other non ionic optical brightening agents which are known for improving whiteness of natural fabric, these are difiicult or impossible to include in a composition which softens by cationic softener, in the amount necessary to overcome the quench effect. The difficutly arises because these nonionic brightening agents, e.g. a-(l-hydroxyethylbenzirnidazol-2-yl)-B-benzimidazol-2-yl ethylene, (hereafter designated (C)) in the needed amount, crystallise out on storage. It has now been found that a brightener selected from the 1,3-diphenyl pyrazoline class of optical brighteners, usually employed exclusively in the treatment of nylon, can be included in amounts necessary to overcome the quench effect in natural or synthetic fabrics and remain stable in storage.
Accordingly, the present invention also concerns compositions which comprise a cationic softening agent, an alkyl ethanolamide and an optical bridghtening agent of the 1,3-diphenyl pyrazoline class.
Incorporation of the optical brightening agent does not impair the softening or the antistatic finish properties which are conferred by the cationic softener and ethanolamide.
Conveniently, the optical brighteners used in the composition of the invention are (1-p-sulphoamidophenly)- 3-(p-chlorophenyl) A -pyrazoline (hereafter referred to as A) and 1-(p-methoxycarbonyl-phenyl)-3-(p-chloro phenyl) A -pyrazoline (hereafter referred to as B).
In addition to overcoming the quench effect, they may also provide optical brightening additional to that accruing from a wash cycle wherein a detergent containing an optical brightener was used.
The storage stability of the compositions can be determined by testing the nylon whitening effect of the composition immediately on preparation and after 3 months storage at 20 C. as follows: non-flourescent nylon is washed for 3 minutes at 45 C. in 0.4% fiuorescer-free commercial detergent, rinsed in water, and then for minutes at 40 C. in 0.15% concention of composition. 5 wash/rinse cycles were carried out, at a liquor/cloth ratio of 30/1 using distilled water. Results are tabulated below:
Harrison fluorescence meter 1 reading After storage at C. On Preparation 3 months 6 months (i) 0.065% br' htener (C) 59 34 (ii) 0.13% brightener 76 54 (iii) 0.13% brightener (A) 61 62 60 l Commercially available instrument.
ing a fiuorescer used in the art as a cotton fluorescer. The cotton was rinsed for 1 minute in water at room temperature and liquor/cloth ratio of 50/1 and then rinsed in the products listed in Table II at 0.15% concentration in water, of 24 H., for 2 minutes at C. and a liquor/ cloth ratio of 100/ 1. The results after 5 wash/ rinse cycles are tabulated; these and visual comparisons clearly show that the modified composition is effective in overcoming the quench effect on fluorescent cotton.
TABLE 11 Product Harrison meter reading (1) Water alone 137 (2) Composition of Example 1 in water 102 (3) Modified composition in water 134 Nylon: non-fluorescent.-Non-fiuorescent nylon was washed for 3 minutes at C. in 0.4% fiuorescer-free commercial detergent, rinsed in water and then for 5 minutes at 40 C. in 0.15 concentrtaion of the modified composition in water. 5 wash/rinse cycles were carried out. A liquor/cloth ratio of 30/1 and distilled water were used. The results are shown in Table III and demonstrate the enhancing of the whiteness level by the modified composition.
TABLE III Harrison meter reading Rinse in water alone 10 Rinse in modified composition solution 66 Nylon: Fluorescent.--Fluorescent nylon, prepared by rinsing for 10 minutes at C. in 5 ppm. of optical brightener (A) at a liquor/cloth ratio of 100 1, was washed for 3 minutes at 45 C. in 0.15% of a commercial detergent, rinsed for 2 minutes in water and for 2 minutes at 40 C. in the products of Table IV. Distilled water and a liquor/ cloth ratio of 30/1 were used.
TABLE IV After 5 Alter 10 wash/rinse wash/rinse Initially cycles cycles (1) Water 142 135 130 (2) Composition of Example 1 in water (0.15% solution in water) 142 137 130 (3) Modified composition (0.15%
solution in water) 142 148 152 EXAMPLE 4 The composition of Example 1 having 0.13% A or 0.13% B therein.
EXAMPLE 5 The composition of Example 2 having 0.20% A therein.
EXAMPLE 6 The composition of Example 3 having 0.13% A or 0.13% B therein.
Inorganic salts, perfume, colourants and ingredients which are similarly non-deleterious to the softening or fiuorescing activity can be included. Also, additives for the purpose of obtaining improved freeze-thaw characteristics, e.g. ethylene glycol, polyethylene glycol and shortchain quaternary ammonium compounds, may be included.
The fabric conditioner is preferably made up as an aqueous dispersion by heating the mixed components at ca. C. and addition of water to The cooled product is thinned, if necessary, by addition of electrolyte, e.g. sodium carbonate with stirring. The fabric conditioner may also be prepared in solid form by employing urea in place of the water. It is preferably employed at a concentration of 0. 1-0.5% by weight of conditioner in water. It can be applied to the fabric by immersing the fabric in a bath containing it. Other methods such as spraying or padding on may be employed.
The present invention is concerned also with the fabric so treated.
The compositions according to this invention have the advantage of applicability to all the usual ingredients of the domestic wash and achieve softening and maintenance or enhancement of the whiteness level together with an antistatic finish where appropriate in a single rinse treatment.
What is claimed is:
1. A fabric softening composition for softening and rendering antistatic a textile fabric which consists essentially of a mixture of (i) 3.75% by weight of di-hardened tallow dimethyl ammonium chloride, and (ii) 2.25 by weight of tallow ethanolamide and 2.25% by weight of tallow diethanolamide, the balance of said composition consisting essentially of water.
References Cited UNITED STATES PATENTS 3,256,180 6/1966 Weiss et al. 252-8.8 3,255,203 6/1966 Schinzel et al. 252-3012 3,216,944 11/1965 Frederick'son 252-8.8 3,223,545 12/1965 Gallaugher et al. 252-8.8 X 2,067,202 1/ 1937 Pool et al. 117-1395 X 2,089,212 8/1937 Kritchevsky 252-357 X 3,135,742 6/1964 Wagner et al. 117-335 X 3,357,988 12/1967 Hausermann et al. 117-335 HERBERT B. GUYNN, Primary Examiner.
US. Cl. X.R. 117-335, 139.5; 252-8.8, 301.2
US468918A 1964-07-08 1965-07-01 Fabric conditioner Expired - Lifetime US3451927A (en)

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Application Number Priority Date Filing Date Title
GB2812464A GB1104441A (en) 1964-07-08 1964-07-08 Fabric conditioner
US46891865A 1965-07-01 1965-07-01

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DE (1) DE1469497B2 (en)
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SE (1) SE333130B (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2053194A1 (en) * 1969-07-28 1971-04-16 Colgate Palmolive Co
US3674688A (en) * 1969-10-20 1972-07-04 Rlr Chem Co Inc Wrinkle removing product and process
US3936537A (en) * 1974-11-01 1976-02-03 The Procter & Gamble Company Detergent-compatible fabric softening and antistatic compositions
EP0075770A2 (en) * 1981-09-25 1983-04-06 Bayer Ag Textile treating composition and its use in finishing textile materials
US4421514A (en) * 1982-08-03 1983-12-20 Colgate-Palmolive Antistatic laundry treatment
US4622154A (en) * 1984-04-19 1986-11-11 Lever Brothers Company Aqueous fabric softening composition
US4627925A (en) * 1984-04-19 1986-12-09 Lever Brothers Company Aqueous concentrated fabric softening composition
EP0547723A1 (en) * 1991-12-18 1993-06-23 Colgate-Palmolive Company Free-flowing powder fabric softening composition and process for its manufacture

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2928141A1 (en) * 1979-07-12 1981-02-05 Hoechst Ag SOFT SOFTENER
DE2930061A1 (en) * 1979-07-25 1981-02-19 Hoechst Ag SOFT SOFTENER

Citations (8)

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Publication number Priority date Publication date Assignee Title
US2067202A (en) * 1930-09-29 1937-01-12 Celanese Corp Textile operation
US2089212A (en) * 1936-06-08 1937-08-10 Kritchevsky Wolf Hydrotropic fatty material and method of making same
US3135742A (en) * 1956-03-03 1964-06-02 Bayer Ag 1, 3-diaryl and 1, 3, 5-triaryl-pyrazoline derivatives
US3216944A (en) * 1961-09-11 1965-11-09 Procter & Gamble Stabilized fabric softener composition
US3223545A (en) * 1962-10-08 1965-12-14 Phillips Petroleum Co Dialkanol amide antistatic composition for polyolefins
US3255203A (en) * 1966-06-07 Ii chz xn
US3256180A (en) * 1962-08-14 1966-06-14 Little Inc A Fabric softener compositions
US3357988A (en) * 1964-05-27 1967-12-12 Geigy Chem Corp Pyrazoline optical brighteners

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3255203A (en) * 1966-06-07 Ii chz xn
US2067202A (en) * 1930-09-29 1937-01-12 Celanese Corp Textile operation
US2089212A (en) * 1936-06-08 1937-08-10 Kritchevsky Wolf Hydrotropic fatty material and method of making same
US3135742A (en) * 1956-03-03 1964-06-02 Bayer Ag 1, 3-diaryl and 1, 3, 5-triaryl-pyrazoline derivatives
US3216944A (en) * 1961-09-11 1965-11-09 Procter & Gamble Stabilized fabric softener composition
US3256180A (en) * 1962-08-14 1966-06-14 Little Inc A Fabric softener compositions
US3223545A (en) * 1962-10-08 1965-12-14 Phillips Petroleum Co Dialkanol amide antistatic composition for polyolefins
US3357988A (en) * 1964-05-27 1967-12-12 Geigy Chem Corp Pyrazoline optical brighteners

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2053194A1 (en) * 1969-07-28 1971-04-16 Colgate Palmolive Co
US3674688A (en) * 1969-10-20 1972-07-04 Rlr Chem Co Inc Wrinkle removing product and process
US3936537A (en) * 1974-11-01 1976-02-03 The Procter & Gamble Company Detergent-compatible fabric softening and antistatic compositions
EP0075770A2 (en) * 1981-09-25 1983-04-06 Bayer Ag Textile treating composition and its use in finishing textile materials
US4446034A (en) * 1981-09-25 1984-05-01 Bayer Aktiengesellschaft Textile-treatment agents, and their use for finishing textile materials
EP0075770A3 (en) * 1981-09-25 1985-01-16 Bayer Ag Textile treating composition and its use in finishing textile materials
US4421514A (en) * 1982-08-03 1983-12-20 Colgate-Palmolive Antistatic laundry treatment
US4622154A (en) * 1984-04-19 1986-11-11 Lever Brothers Company Aqueous fabric softening composition
US4627925A (en) * 1984-04-19 1986-12-09 Lever Brothers Company Aqueous concentrated fabric softening composition
EP0547723A1 (en) * 1991-12-18 1993-06-23 Colgate-Palmolive Company Free-flowing powder fabric softening composition and process for its manufacture
US5259964A (en) * 1991-12-18 1993-11-09 Colgate-Palmolive Co. Free-flowing powder fabric softening composition and process for its manufacture
GR1001506B (en) * 1991-12-18 1994-02-28 Colgate Palmolive Co Free-flowing powder fabric softening composition and process for its manufacture.

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CH461426A (en) 1968-08-31
DE1469497B2 (en) 1975-10-09
SE333130B (en) 1971-03-08
DE1469497A1 (en) 1969-01-02

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