CA2064918A1 - Compositions having a physiological cooling effect and active compounds suitable for these compositions - Google Patents

Compositions having a physiological cooling effect and active compounds suitable for these compositions

Info

Publication number
CA2064918A1
CA2064918A1 CA002064918A CA2064918A CA2064918A1 CA 2064918 A1 CA2064918 A1 CA 2064918A1 CA 002064918 A CA002064918 A CA 002064918A CA 2064918 A CA2064918 A CA 2064918A CA 2064918 A1 CA2064918 A1 CA 2064918A1
Authority
CA
Canada
Prior art keywords
ketal
compositions
cooling effect
alkylene radical
composition according
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.)
Abandoned
Application number
CA002064918A
Other languages
French (fr)
Inventor
Helmut Grub
Ralf Pelzer
Rudolf Hopp
Roland Emberger
Heinz-Jurgen Bertram
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Haarmann and Reimer GmbH
Original Assignee
Helmut Grub
Ralf Pelzer
Rudolf Hopp
Roland Emberger
Heinz-Jurgen Bertram
Haarmann & Reimer G.M.B.H.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Helmut Grub, Ralf Pelzer, Rudolf Hopp, Roland Emberger, Heinz-Jurgen Bertram, Haarmann & Reimer G.M.B.H. filed Critical Helmut Grub
Publication of CA2064918A1 publication Critical patent/CA2064918A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24—Thermal properties
    • A61K2800/244—Endothermic; Cooling; Cooling sensation

Abstract

Compositions having a physiological cooling effect, and active compounds suitable for these compositions A b s t r a c t Ketals, preferably glycerol ketals such as, for example, l-menthone glycerol ketal or 3,3,5-trimethylcyclohexanone glycerol ketal, have a physiological cooling effect and are therefore suitable as active compounds in composi-tions which are intended to cause a sensation of freshness on human skin or mucous membrane.

HR 123-Foreign countries

Description

3~

The invention relates to compositions which do not have an interfering odour and taste ,and which cauqe a physio-logical cooling effect when ap]plied to the skin or the mucous membranes. It seems that the effect which conveys to the person concerned a sensation of freshness can be attributed to stimulation of th~s corresponding receptors of the human nervous system. I'he invention furthermore relates to new compounds which are capable of causing thi~ effect.

The best known natural compound which ha~ a physiological cooling effect is, without doubt, ~ menthol, which is a component of peppexmint oil (e~ Mentha arvensis~. It is employed, for example, for manufacturing dentifrices, mouth washes, foodstuffs, beverages and cosmetics.
However, the typical strong peppermint flavour and ~he bitter and stinging taste are frequently found unpleasant.

There has therefore been no lack of attemp~s to find substances which have the positive cooling effect without the abovementioned shortcomings of menthol. For example, German Offenlegungsschrift 2,202,535 proposes p-menthane-3-carboxamide and esters of p-menthane-3-carboxylic acid, German Offenlegung~schrift 2,205,255 propo~es N-substituted p-menthane-3-carboxamides, German Offen-legungsschrift 2,317,538 pxoposes alipha~ic amides, German Offenlegungs~chrift 2,334,985 proposes cyclic and HR 123-Forei~n countries - 1 -.: ' ~ ` ' . ' `~ ''' ` ' ' acyclic sulphoxides and ~ulphones, and German Offen-legungssch~ift 2,345,156 proposes aliphatic substituted phosphine oxide~. However, these compounds do not occur naturally and are also not degraded by the h~man organism to give substances which occur in nature. Cons equently the use of these substances in foodstuffs can be considered as being questionable.
Menthol derivatives have also been investigated; however, they do not completely meet lhc set requirements. For example, 1-menthylethyl car})onate, which has been proposed in German Offenlegungsschrift 2,022,364, smells of oranges, menthyl N-acetylglycinate, which has been proposed in German Offenlegungsschrift 2,433,165, and the menthol esters of heterocyclic carboxylic acids, which have been proposed in German Offenlegungsschrift 2,339,661, are bitter, and some of the menthyl keto esters which hav~ been pr~posed in US Patent Specification 3,830,930 are bitter over a prolonged period and their cooling effect is only poor.

German Offenlegungsschrift 2,608,226 discloses menthol esters of naturally occurring C2-C6-hydroxycarboxylic acids (which, in turn, may be es~erified on the hydroxyl group with Cl-C4-carboxylic acids), which are odourless and flavourless and have a prolonged cooling effect.
l-Menthyl lactate, in particular, has proven itself in practice. Howsver, the product is not stable to alkalis, so ~hat it is not suitabla for all types of application (for exa~ple soaps~.

HR_123-Foreiqn countrie~ - 2 -' :. ' ' '`': .. ~. :::
' ;, . ' . . :. ~ ' :
, :: . '.
3~

Other products too are already being employed in practice, for example 3-1-menthoxypropane-1,2-diol (European Patent Specification 80,148) and N-ethyl~p-menthane~3~carboxamide (German Offenlegungsschrift 2,205,255 and 2,413,63g). ~owever, there wa~ a demand for compositions with an increased cooling effect or a better price/performance ratio.

Surprisingly, it has now been found that selected ketals have the desired advantageous combination of desirable properties.

The invention relates to compositions which ha~e a physiological cooling effect and which contain at least one ketal of the formula R3 ~o R1 (X) in which Rl represents a C2-C~-alkylene radical having at least 1, but not more than 3, hydroxyl group(s~, prefer~bly 1 hydro~yl group, and either R2 and R3 independently of one another represent Cl-C1O-alkyl which is optionally subs~
tuted by 1 to 3 radicals selected ~rom the ~roup comprising hydroxyl, amino and halogen (such as fluorine, chlorine, HR 123-Foreiqn countries - 3 - . . ~. i : :

:

z~
bromine or iodine), C5 C7-cycloalkyl, preferably cyclohexyl, C6-Cl2-axyl, preferably phenyl, with the proviso that the total o~ the C
atoms of R2 and R3 is not less than 3, or R2 and R3 together represent an alkylene radical which, together with the carbon atom which carries the radicals R2 and R3, forms a 5-7-membered ring, it being possible for this alkylene radical, in turn, to be substituted ~y Cl-C6-alkyl groups.
.
Preferred radicals R2 and R3 comprise methyl, isopropyl and tert.-butyl.

The length of the radic ls R2 and R3 influences the effect of the compounds I: shorter radicals lead to an immediate, hort effect; longer radicals lead to a ~ -delayed, but prolonged effect. An important aspect for the cosme~ics inidustry is the solubility of tha compounds in water; this is the case, in particular, with short ~radicals R2 and R3. ;~

Pre~erred radicals R1 embrace 1,2- and 1,3-alkylene radicals which, together with $he two oxygen atoms and HR 123-Foreian countrie~ - 4 -, ' , ` ' ,' ' : '' ~ . ' ' :' `

~?~ 8 with the carbon atom to which the two oxygen atoms are attached, form a dioxolane or dioxane ring.

Preferred compounds I in wh.ich R2 and R3 together represent an alkylene radical are those of the form~la R12 R13 R14 ~?15 ~ Rlo ~ ~ Rl (Ia) [ R9~R4 in which R4 to Rl5independently of one another denote hydrogen or Cl-C~-alkyl, preferably hydrogen or Cl-C4-alkyl, and , m and n independently of one another denote zero or 1.

Preferred compounds of the formula Ia are those in which the total of m + n is 1, i.e. ketals of an optionally substituted cyclohexanone.

Preferred sub~tituents, of which here may be present, in HR 123-Foreiqp countries - 5 -. . ~ , .
"; ~

,: :
'......... . - .

, :~
, ' 9~

particular, 1 to 3, axe methyl, isopropyl and tert.-butyl.

The ket~ls I are eith~r knowT~, or they have no~ been known to date and can be prepared by analogous, known processes. For example, ketal I will generally be prepared by acid-catalysed reaction of the ketone on which ketal I is based and not less than the e~uivalent amount of aliphatic C3-C6-alcohol having not less than 3 and not more than 5, preferably 3, hydroxyl groups. In general, ~he ketone on which ketal I is based and not les~ than 0.5 mol equivalents, but, as a rule, a 1.2- to 4-fold, preferably 1.5- to 3-fold excess of this amount of ~he C3-C6-alcohol having 3 to 5 hydroxyl groups will be employed. Examples of acid catalysts which can be u~ed are p-toluenesulphonic acid, phosphoric acid or potassium hydrogen sulphate in catalytically effective amounts (for example 0.1 to 3 g of p-toluenesulphonic acid per mole of ketone)~ The reaction will preferably be carried out either in an organic solvent which together with water forms an a~eotrope, so that the water, which is liberated during the formation of the ketal, can be elLminated by azeotropic entrainment, or water-consuming corea~ents such as, for example, trialkyl ortho esters are used.
Examples of prefarred organic solvents comprise benzene, toluene, xylene, chloroform, methylene chloride and trichloroethylene. The reaction can be regarded as comple~e when water no longer ~eparates out or wh~n an ester/alcohol mixture is no longer separated out. It is recommended to wash the pxoducts subsequently with dilute HR 123-Forei n countries - 6 -,~
,, ~ , ~ . , 20-l~lhR-lY92 14: 0g 13f~ R hG LE~JERKUSE~`J -~'19 21~ 3034EIZ S. 02 alkali ~ncl ~ ith wat~ co ~ ?a~at~ and dx~ th~ orS~anic ph~Ye, to ~t~ip of ~ th~ Y~lv~nt:, ~nd, if ~p~op~iate, t,o 5 purlfy t}~e r~ ue~ fc)~ ~xa~pl~ ~ d~ ation~

Particul~rly p~erxed k~ I ar~ ~ho~e o~ t~ onnula~a I

~o~

t~I~ tI~I~

$~)~ 1 ~S~O~R 1 ~Iv) ~v~
~ .

tYI
2s in which ~I h~s th~ a~oveinentioned ~ea~ing a~d pref~rab1y stands ~or CH2jC~ 2- ~- 4f` ~C~ 2- . JKetals ~roln ~Iycerol ~ ~OEI C~C~20~ ~3 ~zC)~
30 ~nd i~s hosnol~gues a~ p~icularly pre~red.
The inventio1l also ~dates to the ~e~ls ~II to VI.

3-~rç~b~ 7 , : , -713~ R-1992 14~ 3h`l'ER h~i l E~IER~';U~EN +49 214 3034~32 5,03 The k~3t~1~ I tc~ b~ ~mployo~ in th~ com~o~it~o~ ~c~ordi~ç
~o ~h~ in~rention c~n h~v~ ric C ~to~s ~ optlcal i m can ~h~ro~or~ oc~S~ h~pendin~ on th* ~tar~in~
mat~ri~l ~nd ~h~ b~re~a~a~ion m~thod8 ufied, ~h~ar can ~xls:t ln th~ ~orr~ o f, ~aixl:~u~ o~ t~e op~ al i~om~r~ o~ ~.n th~
fo~m o~ pu~6~ L~iom~r~. ~rhe cooling ~ff~c:t o tl ~ lsiom~
may cli~ert so tha~ on~ oJ: the o~ch~ er m~Sr be pre~e~r~d .

13esidf~ th~ X{3tals I, th0 cc)~aposi~ion~ ~c¢oxcllng 'co thæ
~nvention may conta~ n ~ carri~rs ancUor dilu6an~ . Th~
na~-ure o~ t~ dc~p~3nd~ on the int~ 3d u~ o~ 'ch~
compo~i'CiOSl -"'h~ omposi~ions acc~ din~ ~o tll6~ in~ontion C~A~ be u~
for all purpuse~ wher~ a phy~iological coolin~ ~f ~ect i~
d~si~ed. ~xample~ o~ product~ in ~hich ~uch cc~ol~nt. a~e f~equ~ ly usl~d are lllxu~y itern~ ~3uc:h ~3 ch~,ring S~ura, c~ewin~ toba,c~:o, cigaxet~es, ~e~r~rages, ic~ cx~am, conect~ ,nary, ~;ltS u3ed in the r~anufacture o~ wa~ s, ph~rma~euti~al ~?:repara~ions, body cax~ product~ or cos-me~ic pxepa~s.tions~ such as den~riXic~, mouth wash~esr preparations ~or ~rg~in~, p~r~:~n~, powdexs, ~c~tions, ointme~t~, oili~, c~ , shavin5~ fo~, ~f1;e3:sha~
~harnpoo~ e~c.

The rea~y to ~se prod~ts contaln the ketals I in dn ~mo~lnt which is suffic7en1; for provoking ~h~ six~d Pi~nsation o~ :
cold. ~ a rulet 0.01 ~o 3, pre~e~ra.bly 0.05 ~o 1, per ... _ . . ......
., , ,, , :.

.. ..
, .
~, , . . .

oen~ ~ weight ar~ u~od r~l~tiv~ to the ~ hl: o~ t~
r~a~y t~ uj~ ~r~luCt (~,~. toothpaste~ mouthwash).

Thla ~x~;>le~ which ;~ollow illu~ratia th~ inv~3htiono llnl~ o~herwi~e indicat~d, ~rc:*ntag~ e ~ nt by S w~ai~h~.
~a~
~s ~-~n-ths; n~ glyc:erol, Icet:~l ( kr~own ~xom S~i~ihchuk, A.~.; M~hn~Ykii, 1~7.~, Mi3cryuko~a, N.~Ch. Uk~ Rh~ h. (RUS8. ~d.
~,3~2), 1~3-6, 1~77 C~ 87(5); 3g6~7U~

Tn a 2 1 three-ns~Ck~d ~iask th~3xe ~r~ introduo~cl 3û8 ~ of nc~one t ~ mol J, ;~ or glycerol ~ 3 sQol ) ~nd ~ g of potas~ hydroc~n ~ul~hate in tol~en~. Thi~ mixtur~2 i8 ro~ x~c~ in a ~at~ ~epa~ator. A~2r 7 hour~, 42 ~ Of a~hO,~ p~ O,L~. T~ UlJCl;U~ eu~ ec~ an~
distillad.

A~ ~0~106~CJl mbar, 441 g o~ a colc~urless, cl~j~r liquid A f e~ f ~ S oi~m~t~ ph~ ~ lo ~h~t t;l ~ ~u ~
~s ovex 9~ Accor~in~ to the ~ s~ctr~m, the r~ul~cin~
20compo-~nc~ cantains a 3, 3-dioxolan~3 rin~.
n20 ~ 4~: a~ 14 . 1~; d~!5~ 1 .038t~.

~_9C~ _ g _ ~t3-5 ZOP~ Z Gt:~l r;~~,rl~ 5t~ ~Q,l,t~ l 05~ ZGG~ ~t,~W t3Z

, , .
:
. ~

~" ' ' ~' ' '', ~ ' ~ . ' ' 2~ 3~ 8 ~ 3, 3, S-~rim~th.yl~y~loh~xallon~ yaerol k~t~l A 2ni~t~ o~ 140 9 o1 3, 3 " S~ loh-~anon~
ol ), 184 S~ o~ ~lycerol ( 2 ms~l ) and ~ q o . p-tolueno sulphonic ~ in ~oluQn~ reat~d ~ in Ex~mpl6~ 1~

A~ J;C'C;~1-5 m~ Z3!3 5~ O~ OlC:)Urle~ a~ id distll over. Ga~ c~owato~Aphy ~ ra~ th~t the ~urit~
is ~v~3~ 999~ .
n~ a 1.4699; d(25~C) = 1.0~6~ m.~ 20~C~

3-~th~ 2-bu~anon~ ~lys:eJcol ke~al A n~ixtur~a o~ &g4 ~ 3-mQthyl-2-but~nonai~ (5~75 mol) S~9 g o:~ glyoe~ol ( 5 . 75 mol ~ and 4 g o~ p-tolu~ ul-phonic acid i8 introduced in~o a :r~action Vd3~i5ei and 670 y o trimetl~yl orthoforma~ ~ S ~ 32 ~1) ~ e ~ub~-quentl$t ~d~d drop~ise. During thi~ prc~c:e~s, ~h~3 tç~mperatur~ of the reac:tio~ mixtur~ risos to alpprox.
~5~-50C. ~rhe r~asllltin~ met~hanol/ma~hyl l~orm~te mixture L~ L~ u~ sprserl~ p~e~sur~: ~o a hotrc~m temp~ratu~e o~ C. It i~ th~n ~ool~d ~o 50C, a vacuu~
i~ appl~i3d ~1DW1Y/ ~nd th~ mixture i~ ~u~je::ted to Y, ~ ~L ,.~llaS~.t ~ lyl~ v ~uul~l . ~ull~ ;i g;
nD = 1.4~13~; d~5~C~ ~ 1.0294.

50'5 Zab0 b~Z 6b+ ~135~ 13031 ~ ~3,~ 1 6S:b~ Z661~ 0Z

2~

~a~ chrom~to~ra~hy r~veal~; ~h~t ~e purity 1~ 97, S~ .
Th~ pr~c~ was al50 U~ ro~ pr~p~rin~ ~he ~411Os~-in~ compoundl~:
, ~2 ~ 20 d(~5~3 W~i~h~
the 2q~1n ~r~cti~n 1 0 ~
4 ~ ~utyl ~3thyl 1 . 4 4 2 5 0 . 9 9 g 5 74 8 t~Butyl ~e~hyl 1,44R6 1.0160 B21 6 E:thyl Ethyl 1.4447 1.~330 667 7 i-Prop~ Pxopyl 1.455~ 1.0167 830 9 ~h3,rl :M~th$~ 341 1,0655 667 FJXamplCt8 3-8 ~ te ~o su~s~anc~3s ~ith l::ooling ei~ t;
~ ow~19 ~ ou~ ~ac~ L ,v~ y t~

~xasnple l-~enthone l.l.1-~imethylol~thane ketal (~ 7-I~opropyl-3.lO d~nethyl-l.S-dioxa-~ ]Un~CaTI-3~meUl~nOl) 2s l-Menthone ar~d 1.1.1~trimethylolethan~ we~e ~ac~d in analo~y so Example 1, A
cololl~le~8 hi~h-vi~c~ i1 hs~v;n~ th~. follcl~in$ r)rnperLi~ w~ ht~ A
l~.p,: 134~C: (1 m~ i n 20: 1 4g33; ~ 27.3.

~}nple 11:

I-Menth~l-e I.I.I-trim~.rhylolpr~p~e ke~l (~ hyl 7-i~oprop~ ~mothyl-1.5 dioxa~piro[S.5]undecan-3-nlcth~nol) 35 I-Menthone and 1.1.1-srime~lylolpropane wer~ reacle;i in analogy to Ex~mple l. A
Iourlss~ high-~ ou4 oil h~vin~ o follc~wi~l~s pr~ps:r~i~S WZIS C~ ilU;~;
b.p.: 148C (I mb~r~; n D: 1 .4850; ~x 24s -25). 1.

90 S ZSI70 blZ 6b+ 113-.rl:~kl31l31 ~W ~13~ [ 00:Sr Z661~ W-0Z

:
~.

.~.'. ' : . ~, .

'~ 9~8 ~m~4 I~ cnsh~ 2.4-butAn~,u~ X~ yl~ yl-1.4-~liu~splr decan-~eth~n~lJ
l-Menthon~ d l.~.~bulanet~iol were reacte~i in analogy lo Ex~nple l.

~o ~o ~6 '~

~ ~n~

~ C~ ~J~ IU~~ J Ll~ ~OCI~ U~ DC

. - . . ; , ~ .
, , . , / " . . . , , ~
~ . .
.,

Claims (8)

1. Composition which have a physiological cooling effect and which contain at least one ketal of the formula (I) in which R1 represents a C2-C8-alkylene radical having at least 1, but not more than 3, hydroxyl group(s), and either R2 and R3 independently of one another represent C1-C10-alkyl which is optionally substituted by 1 to 3 radicals selected from the group comprising hydroxyl, amino and halogen, or C5-C7-cycloalkyl, or C6-C12-aryl, with the proviso that the total of the C
atoms of R2 and R3 is not less than 3, or R2 and R3 together represent an alkylene radical which, together with the carbon atom which carries the radicals R2 and R3, forms a 5-7-membered ring, it being possible for this alkylene radical, in turn, to be substituted by C1-C?-alkyl groups.

HR 123-Foreign countries -13-
2. Composition according to Claim 1, where R1 denotes a 1,2- or 1,3-alkylene radical.
3. Composition according to Claim 1, where R1 denotes , or .
4. Composition according to Claim 1, where the ketal is one of the formula (Ia) in which R4 to R15 independently of one another denote hydrogen or C1-C8-alkyl and m and n independently of one another denote zero or 1.
5. Composition according to Claim 4, where the total of m+n is 1.

HR 123-Foreign Countries -14-
6. Compounds of the formulae (III) (IV) (V) (VI) where R1 is as defined in Claim 1.
7. Compound selected from the group consisting of 3.3.5-trimethylcyclohex?
none glycerol ketal, 1-menthone 1.1.1-trimethylolethane ketal, 1-menthone 1.1.1-trimethylolpropane ketal, and 1-menthone 1.2.4-butanetriol ketal.
8. Use of compounds of the formula (I) according to Claim 1 for achieving a cooling effect on human skin or mucous membrane.

HR 123-Foreign countries -15-
CA002064918A 1991-04-05 1992-04-02 Compositions having a physiological cooling effect and active compounds suitable for these compositions Abandoned CA2064918A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4110973A DE4110973A1 (en) 1991-04-05 1991-04-05 MEDIUM WITH A PHYSIOLOGICAL COOLING EFFECT AND EFFECTIVE COMPOUNDS SUITABLE FOR THIS MEDIUM
DEP4110973.2 1991-04-05

Publications (1)

Publication Number Publication Date
CA2064918A1 true CA2064918A1 (en) 1992-10-06

Family

ID=6428853

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002064918A Abandoned CA2064918A1 (en) 1991-04-05 1992-04-02 Compositions having a physiological cooling effect and active compounds suitable for these compositions

Country Status (10)

Country Link
US (1) US5266592A (en)
EP (1) EP0507190B1 (en)
JP (1) JP3071030B2 (en)
AT (1) ATE123936T1 (en)
AU (1) AU653999B2 (en)
CA (1) CA2064918A1 (en)
DE (2) DE4110973A1 (en)
DK (1) DK0507190T3 (en)
ES (1) ES2073205T3 (en)
IE (1) IE67879B1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303817B1 (en) 2000-08-10 2001-10-16 International Flavors & Fragrances Inc. Method for making amides
US7025997B2 (en) 2003-09-24 2006-04-11 International Flavors & Fragrances Inc. Coolant plant extract compositions containing monomenthyl succinate

Families Citing this family (271)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5348750A (en) * 1990-11-06 1994-09-20 Wm. Wrigley Jr. Company Enhanced flavors using menthone ketals
DK0485170T3 (en) * 1990-11-06 1995-12-11 Wrigley W M Jun Co Improved taste using menthon catals
CA2134977C (en) * 1992-05-18 1998-12-15 Deanna K. Furman Coolant compositions
ES2105293T3 (en) 1992-06-17 1997-10-16 Procter & Gamble REFRESHING COMPOSITIONS WITH REDUCED IRRITATING EFFECT.
US5602178A (en) * 1994-11-14 1997-02-11 Ciba-Geigy Corporation Bath products containing menthyl lactate
US5649914A (en) * 1994-12-22 1997-07-22 Kimberly-Clark Corporation Toilet training aid
US5681298A (en) * 1994-12-22 1997-10-28 Kimberly-Clark Worldwide, Inc. Toilet training aid creating a temperature change
US6100233A (en) * 1996-08-19 2000-08-08 The Procter & Gamble Company Odor control compositions comprising β-ketoester pro-fragrances
US6126953A (en) * 1996-08-19 2000-10-03 The Procter & Gamble Company Fragrance delivery systems for personal care articles
WO1998007455A1 (en) 1996-08-19 1998-02-26 The Procter & Gamble Company ODOR CONTROL COMPOSITIONS COMPRISING β-KETOESTER PRO-FRAGRANCES
US6093691A (en) * 1996-08-19 2000-07-25 The Procter & Gamble Company Rinse added fabric softening compositions and method of use for the delivery of fragrance derivatives
US6150310A (en) * 1996-08-19 2000-11-21 The Procter & Gamble Company Laundry detergent compositions comprising β-ketoester pro-fragrances
EP0977830B1 (en) 1997-04-24 2005-12-28 The Procter & Gamble Company Personal care composition comprising orthocarbonate pro-fragrances
US6087322A (en) * 1997-04-24 2000-07-11 The Procter & Gamble Company Fragrance pro-accords
US6316397B1 (en) 1997-06-27 2001-11-13 The Procter & Gamble Co. Pro-fragrance linear acetals and ketals
US6083892A (en) * 1997-08-19 2000-07-04 The Procter & Gamble Company Automatic dishwashing detergents comprising β-ketoester pro-fragrances
US6455080B1 (en) 1997-12-29 2002-09-24 Wm. Wrigley Jr., Company Chewing gum containing controlled release acyclic carboxamide and method of making
WO1999013734A1 (en) 1997-09-18 1999-03-25 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
US6627233B1 (en) 1997-09-18 2003-09-30 Wm. Wrigley Jr. Company Chewing gum containing physiological cooling agents
AU9757398A (en) † 1997-11-27 1999-06-16 Firmenich S.A. Novel compounds derived from menthol and use as refreshing agent
SG71877A1 (en) * 1997-12-19 2000-04-18 Johnson & Johnson Consumer Novel powder compositions
US7588793B1 (en) 1998-06-05 2009-09-15 Cadbury Adams Usa, Llc Enhanced flavoring compositions containing N-ethyl-p-menthane-3-carboxamide and method of making and using same
US20010018579A1 (en) 1998-12-18 2001-08-30 Walter Klemp Disposable absorbent garment having stretchable side waist regions
CA2361046A1 (en) * 1999-02-02 2000-08-10 Avon Products, Inc. Methods for alleviating discomfort of a hot flash and compositions therefor
ES2298932T3 (en) 1999-03-31 2008-05-16 Firmenich Sa FLAVORING COMPOSITION CONTAINING CUBEBOL AND AT LEAST REFRESHING AGENT.
DE10012949A1 (en) * 2000-03-16 2001-09-27 Henkel Kgaa Mixtures of cyclic and linear silicic esters of lower alcohols and fragrance and/or biocide alcohols are used as fragrance and/or biocide in liquid or solid laundry and other detergents and in skin and hair cosmetics
US8512718B2 (en) 2000-07-03 2013-08-20 Foamix Ltd. Pharmaceutical composition for topical application
EP1250941A1 (en) * 2001-04-17 2002-10-23 The Procter & Gamble Company Articles comprising a mint odor-free cooling agent
US20040082654A1 (en) * 2001-04-17 2004-04-29 The Procter & Gamble Company Cooling compositons
ES2338297T3 (en) * 2001-04-17 2010-05-06 THE PROCTER & GAMBLE COMPANY AN ABSORBENT ARTICLE UNDERSTANDING AN AGENT ABLE TO PROVIDE A PERCEPTION TO THE USER.
US6972010B2 (en) * 2001-04-17 2005-12-06 The Procter & Gamble Company Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived
US8273367B2 (en) * 2001-04-17 2012-09-25 The Procter And Gamble Company Articles comprising a mint odor-free cooling agent
US20050222546A1 (en) * 2004-04-01 2005-10-06 The Procter & Gamble Company Disposable absorbent article having refastenable side seams and a wetness sensation member
US6642427B2 (en) 2001-05-14 2003-11-04 The Procter & Gamble Company Wearable article having a temperature change element
US6627786B2 (en) 2001-11-26 2003-09-30 The Procter & Gamble Company Wearable article having a wetness sensation member
US8445743B2 (en) * 2001-11-26 2013-05-21 The Procter & Gamble Company Wearable article enhancing awareness of urination
US20030139291A1 (en) * 2001-12-04 2003-07-24 Kimberly-Clark Worldwide, Inc. Absorbent composites having cooling effect
IL152486A0 (en) 2002-10-25 2003-05-29 Meir Eini Alcohol-free cosmetic and pharmaceutical foam carrier
WO2004037225A2 (en) 2002-10-25 2004-05-06 Foamix Ltd. Cosmetic and pharmaceutical foam
US7700076B2 (en) 2002-10-25 2010-04-20 Foamix, Ltd. Penetrating pharmaceutical foam
US9211259B2 (en) 2002-11-29 2015-12-15 Foamix Pharmaceuticals Ltd. Antibiotic kit and composition and uses thereof
US9265725B2 (en) 2002-10-25 2016-02-23 Foamix Pharmaceuticals Ltd. Dicarboxylic acid foamable vehicle and pharmaceutical compositions thereof
US7704518B2 (en) 2003-08-04 2010-04-27 Foamix, Ltd. Foamable vehicle and pharmaceutical compositions thereof
US9668972B2 (en) 2002-10-25 2017-06-06 Foamix Pharmaceuticals Ltd. Nonsteroidal immunomodulating kit and composition and uses thereof
US8486376B2 (en) 2002-10-25 2013-07-16 Foamix Ltd. Moisturizing foam containing lanolin
US10117812B2 (en) 2002-10-25 2018-11-06 Foamix Pharmaceuticals Ltd. Foamable composition combining a polar solvent and a hydrophobic carrier
US8900554B2 (en) 2002-10-25 2014-12-02 Foamix Pharmaceuticals Ltd. Foamable composition and uses thereof
US7820145B2 (en) 2003-08-04 2010-10-26 Foamix Ltd. Oleaginous pharmaceutical and cosmetic foam
US20080138296A1 (en) 2002-10-25 2008-06-12 Foamix Ltd. Foam prepared from nanoemulsions and uses
US8592361B2 (en) 2002-11-25 2013-11-26 Colgate-Palmolive Company Functional fragrance precursor
US7575739B2 (en) 2003-04-28 2009-08-18 Foamix Ltd. Foamable iodine composition
EP1479361B1 (en) * 2003-05-19 2010-09-08 The Procter & Gamble Company Volatile material-containing sanitary absorbent article with barrier package
US20040254550A1 (en) * 2003-06-16 2004-12-16 Kimberly-Clark Worldwide, Inc. Temperature change element for use in personal care products
US7250548B2 (en) * 2003-06-16 2007-07-31 Kimberly-Clark Worldwide, Inc. Absorbent article with temperature change member disposed on the outer cover and between absorbent assembly portions
US8486374B2 (en) 2003-08-04 2013-07-16 Foamix Ltd. Hydrophilic, non-aqueous pharmaceutical carriers and compositions and uses
US8795693B2 (en) 2003-08-04 2014-08-05 Foamix Ltd. Compositions with modulating agents
CA2535265C (en) 2003-08-22 2014-01-28 Dendreon Corporation Compositions and methods for the treatment of disease associated with trp-p8 expression
US7767876B2 (en) * 2003-10-30 2010-08-03 The Procter & Gamble Company Disposable absorbent article having a visibly highlighted wetness sensation member
US8591972B2 (en) 2005-05-23 2013-11-26 Kraft Foods Global Brands Llc Delivery system for coated active components as part of an edible composition
US9271904B2 (en) 2003-11-21 2016-03-01 Intercontinental Great Brands Llc Controlled release oral delivery systems
US8389032B2 (en) 2005-05-23 2013-03-05 Kraft Foods Global Brands Llc Delivery system for active components as part of an edible composition having selected particle size
US8591968B2 (en) 2005-05-23 2013-11-26 Kraft Foods Global Brands Llc Edible composition including a delivery system for active components
US8591973B2 (en) 2005-05-23 2013-11-26 Kraft Foods Global Brands Llc Delivery system for active components and a material having preselected hydrophobicity as part of an edible composition
US8591974B2 (en) * 2003-11-21 2013-11-26 Kraft Foods Global Brands Llc Delivery system for two or more active components as part of an edible composition
US8597703B2 (en) 2005-05-23 2013-12-03 Kraft Foods Global Brands Llc Delivery system for active components as part of an edible composition including a ratio of encapsulating material and active component
US20050112236A1 (en) 2003-11-21 2005-05-26 Navroz Boghani Delivery system for active components as part of an edible composition having preselected tensile strength
US20050137166A1 (en) * 2003-12-19 2005-06-23 Alcon, Inc. Use of cooling agents to relieve mild ocular irritation and enhance comfort
WO2006020754A1 (en) * 2004-08-11 2006-02-23 Cadbury Adams Usa Llc Sensate compositions and delivery systems therefor
US7955630B2 (en) 2004-09-30 2011-06-07 Kraft Foods Global Brands Llc Thermally stable, high tensile strength encapsulated actives
US20070148284A1 (en) 2004-08-25 2007-06-28 Cadbury Adams Usa Llc. Liquid-filled chewing gum
US20060142716A1 (en) * 2004-12-29 2006-06-29 Kimberly-Clark Worldwide, Inc. Absorbent article featuring a non-abrasive temperature change member
US20060142713A1 (en) * 2004-12-29 2006-06-29 Long Andrew M Absorbent article featuring a temperature change member
US7956235B2 (en) 2004-12-29 2011-06-07 Kimberly-Clark Worldwide, Inc. Absorbent article featuring a temperature change member
US8129582B2 (en) * 2004-12-29 2012-03-06 Kimberly-Clark Worldwide, Inc. Absorbent article featuring a temperature change member
RU2375049C2 (en) * 2005-01-04 2009-12-10 ТЕЙКОКУ ФАРМА ЮЭсЭй, ИНК. Local cooling plaster
US9198448B2 (en) 2005-02-07 2015-12-01 Intercontinental Great Brands Llc Stable tooth whitening gum with reactive ingredients
EP1716837B1 (en) 2005-02-28 2017-06-07 The Procter & Gamble Company Use of a volatile cooling sensate on fibrous tissues to provide a sensation of rhinological decongestion
US7632978B2 (en) 2005-04-29 2009-12-15 Kimberly-Clark Worldwide, Inc. Absorbent article featuring an endothermic temperature change member
US7851005B2 (en) 2005-05-23 2010-12-14 Cadbury Adams Usa Llc Taste potentiator compositions and beverages containing same
CA2602494C (en) 2005-05-23 2011-10-04 Cadbury Adams Usa Llc Liquid-filled chewing gum composition
WO2006127934A2 (en) 2005-05-23 2006-11-30 Cadbury Adams Usa, Llc Taste potentiator compositions and edible confectionery and chewing gum products containing same
PL1895856T3 (en) 2005-05-23 2017-09-29 Intercontinental Great Brands Llc Confectionery composition including an elastomeric component, a cooked saccharide component, and a functional ingredient
ES2688772T3 (en) 2005-05-23 2018-11-06 Intercontinental Great Brands Llc Composition of chewing gum with central filling
US7851006B2 (en) 2005-05-23 2010-12-14 Cadbury Adams Usa Llc Taste potentiator compositions and beverages containing same
CN101179943B (en) 2005-05-23 2013-06-26 卡夫食品环球品牌有限责任公司 Liquid-filled chewing gum composition
US20060280852A1 (en) * 2005-05-27 2006-12-14 Cadbury Adams Usa Llc. Vanilla-flavored compositions and delivery systems therefor
US7947317B2 (en) * 2005-06-01 2011-05-24 Kraft Foods Global Brands Llc Interconnected confectionery products and method of making and marketing same
WO2006134013A1 (en) * 2005-06-14 2006-12-21 Symrise Gmbh & Co. Kg Mixtures comprising anthranilic acid amides and cooling agents as cosmetic and pharmaceutical compositions for alleviating itching
CN101242807B (en) * 2005-08-12 2014-12-10 洲际大品牌有限责任公司 Mouth-moistening compositions, delivery systems containing same and methods of making same
US8268371B2 (en) 2005-08-22 2012-09-18 Kraft Foods Global Brands Llc Degradable chewing gum
US8287928B2 (en) * 2005-08-22 2012-10-16 Kraft Foods Global Brands Llc Degradable chewing gum
US8263143B2 (en) * 2005-08-22 2012-09-11 Kraft Foods Global Brands Llc Degradable chewing gum
US8282971B2 (en) 2005-08-22 2012-10-09 Kraft Foods Global Brands Llc Degradable chewing gum
US20070221236A1 (en) * 2005-10-05 2007-09-27 Cadbury Adams Usa Llc. Cooling compositions including menthyl esters
US20070077331A1 (en) * 2005-10-05 2007-04-05 Cadbury Adams Usa Llc. Cooling compositions
US7297835B2 (en) * 2005-10-07 2007-11-20 Kimberly-Clark Worldwide, Inc. Absorbent article featuring a temperature change member
US20070083173A1 (en) * 2005-10-07 2007-04-12 Kimberly-Clark Worldwide, Inc. Absorbent article featuring a temperature change member
BRPI0613067A2 (en) * 2005-10-24 2010-12-21 Teikoku Pharma Usa Inc n, 2,3-trimethyl-2-isopropylbutamide pain relief topical compositions and methods of using them
JP5305918B2 (en) 2005-11-22 2013-10-02 サジティス・インコーポレイテッド Glycerol levulinate ketals and their use
US7432413B2 (en) 2005-12-16 2008-10-07 The Procter And Gamble Company Disposable absorbent article having side panels with structurally, functionally and visually different regions
RU2398476C2 (en) 2005-12-23 2010-09-10 КЭДБЕРИ АДАМС ЮЭсЭй ЛЛС Compositions that provide for feelings similar to feelings caused by menthol
US8846007B2 (en) * 2005-12-23 2014-09-30 Intercontinental Great Brands Llc Compositions providing a heating sensation for oral or dermal delivery
WO2007089652A2 (en) * 2006-01-27 2007-08-09 Cadbury Adams Usa Llc Flavor-enhancing compositions, methods of manufacture, and methods of use
CN101420942B (en) 2006-02-15 2014-03-12 登德雷恩股份有限公司 Small-molecule modulators of TRP-P8 activity
US7772266B2 (en) * 2006-02-15 2010-08-10 Dendreon Corporation Small-molecule modulators of TRP-P8 activity
CA2642595C (en) * 2006-02-20 2013-08-27 Gumlink A/S Resin encapsulated food acid
US8491558B2 (en) 2006-03-31 2013-07-23 The Procter & Gamble Company Absorbent article with impregnated sensation material for toilet training
US8057450B2 (en) 2006-03-31 2011-11-15 The Procter & Gamble Company Absorbent article with sensation member
US8664467B2 (en) 2006-03-31 2014-03-04 The Procter & Gamble Company Absorbent articles with feedback signal upon urination
EP2001436B1 (en) 2006-04-05 2017-01-04 Intercontinental Great Brands LLC Calcium phosphate complex and salts in oral delivery systems
US20070275129A1 (en) * 2006-04-21 2007-11-29 Cadbury Adams Usa Llc Coating compositions, confectionery and chewing gum compositions and methods
ES2462925T3 (en) * 2006-06-14 2014-05-26 Symrise Ag Compounds with antimicrobial effect for the treatment of oral fetidity
JP4658222B2 (en) 2006-06-28 2011-03-23 キャドバリー・アダムズ・ユーエスエイ・エルエルシー Process for producing a delivery system for an active ingredient as part of an edible composition
US8319004B2 (en) * 2006-08-17 2012-11-27 Kimberly-Clark Worldwide, Inc. Training article for delivering unique sensations
ES2348675T3 (en) * 2006-08-17 2010-12-10 Gumlink A/S HIGH INTENSITY EDULCORANT ENCAPSULATED IN RESIN.
PL2079321T3 (en) * 2006-09-27 2013-11-29 Intercontinental Great Brands Llc Cooling confectioneries and beverages
US20080260655A1 (en) 2006-11-14 2008-10-23 Dov Tamarkin Substantially non-aqueous foamable petrolatum based pharmaceutical and cosmetic compositions and their uses
US20080166449A1 (en) 2006-11-29 2008-07-10 Cadbury Adams Usa Llc Confectionery compositions including an elastomeric component and a saccharide component
CA2851763A1 (en) 2006-12-04 2008-06-12 The Procter & Gamble Company Absorbent articles comprising graphics
US7875066B2 (en) 2006-12-11 2011-01-25 Kimberly-Clark Worldwide, Inc. Thermal grill for heating articles
GB0703525D0 (en) * 2007-02-23 2007-04-04 Cadbury Schweppes Plc Method of making sweetner compositions
GB0703524D0 (en) * 2007-02-23 2007-04-04 Cadbury Schweppes Plc Improved sweetener compositions
US20080213440A1 (en) 2007-03-01 2008-09-04 Cadbury Adams Usa Llc Non-Aldehyde Cinnamon Flavor and Delivery Systems Therefor
US20090017080A1 (en) * 2007-03-15 2009-01-15 Paul Robert Tanner Personal care kit having skin care compositions with a readily perceptible difference
WO2008122286A1 (en) * 2007-04-04 2008-10-16 Gumlink A/S Center-filled chewing gum product for dental care
US8338659B2 (en) * 2007-04-30 2012-12-25 Kimberly-Clark Worldwide, Inc. Absorbent article featuring leakage warning
GB0713297D0 (en) 2007-07-10 2007-08-15 Cadbury Schweppes Plc Chocolate compositions having improved flavour characteristics
GB0715226D0 (en) * 2007-08-01 2007-09-12 Cadbury Schweppes Plc Sweetener compositions
US8636982B2 (en) 2007-08-07 2014-01-28 Foamix Ltd. Wax foamable vehicle and pharmaceutical compositions thereof
EP2033688B1 (en) 2007-08-20 2012-10-17 Symrise AG Oxalic acid derivatives and their use as physiological cooling agents
EP2209770A1 (en) 2007-10-09 2010-07-28 Segetis, Inc. Method of making ketals and acetals
GB0720516D0 (en) * 2007-10-18 2007-11-28 Cadbury Schweppes Plc Comestible products
WO2009061871A1 (en) * 2007-11-09 2009-05-14 The Hershey Company Multi-layered fondant containing chewing gum
WO2009067587A1 (en) * 2007-11-20 2009-05-28 Cadbury Adams Usa Llc Dual coated confectionery product
MX358121B (en) * 2007-11-29 2018-08-06 Kraft Foods Global Brands Llc Multi-region chewing gum with actives.
MX2010005424A (en) * 2007-11-29 2010-06-01 Cadbury Adams Usa Llc Particulate coating processing.
US9439857B2 (en) 2007-11-30 2016-09-13 Foamix Pharmaceuticals Ltd. Foam containing benzoyl peroxide
WO2010041141A2 (en) 2008-10-07 2010-04-15 Foamix Ltd. Oil-based foamable carriers and formulations
WO2009072007A2 (en) 2007-12-07 2009-06-11 Foamix Ltd. Carriers, formulations, methods for formulating unstable active agents for external application and uses thereof
US8134042B2 (en) * 2007-12-14 2012-03-13 Kimberly-Clark Worldwide, Inc. Wetness sensors
US20090162476A1 (en) * 2007-12-21 2009-06-25 Cadbury Adams Usa Llc Parallel Gum Component Mixing Systems And Methods
EP2242476A2 (en) 2008-01-14 2010-10-27 Foamix Ltd. Poloxamer foamable pharmaceutical compositions with active agents and/or therapeutic cells and uses
WO2009108769A2 (en) 2008-02-27 2009-09-03 Cadbury Adams Usa, Llc Multi-region confectionery
EP2273892A1 (en) 2008-05-02 2011-01-19 Cadbury Adams USA LLC Multilayered sugar free polyol confectionery and methods of making same
US8044258B2 (en) * 2008-06-27 2011-10-25 Kimberly-Clark Worldwide, Inc. Absorbent article featuring leakage warning
US7924142B2 (en) 2008-06-30 2011-04-12 Kimberly-Clark Worldwide, Inc. Patterned self-warming wipe substrates
AU2009282004A1 (en) * 2008-08-15 2010-02-18 The Procter & Gamble Company Solution of menthane carboxamides for use in consumer products
BRPI0917999A2 (en) 2008-08-15 2015-11-17 Procter & Gamble synthesis of cyclohexane derivatives useful as sensory elements in consumer products
GB0817368D0 (en) * 2008-09-23 2008-10-29 Cadbury Uk Ltd Confectionery and methods of production thereof
GB0817369D0 (en) * 2008-09-23 2008-10-29 Cadbury Uk Ltd Confectionery and methods of production thereof
GB0817367D0 (en) 2008-09-23 2008-10-29 Cadbury Uk Ltd Confectionery and methods of production thereof
GB0817366D0 (en) * 2008-09-23 2008-10-29 Cadbury Uk Ltd Confectionery and methods of production thereof
GB0817370D0 (en) * 2008-09-23 2008-10-29 Cadbury Uk Ltd Chewing gum and methods of production thereof
WO2010036884A1 (en) 2008-09-25 2010-04-01 Segetis, Inc. Ketal ester derivatives
US20100129489A1 (en) * 2008-11-12 2010-05-27 Bharani Ashokan Sensate-plated sanding composition and products made therefrom
AU2009318056B2 (en) 2008-11-20 2014-07-24 The Procter & Gamble Company Personal care compositions providing enhanced cooling sensation
US9700065B2 (en) * 2008-11-28 2017-07-11 Intercontinental Great Brands Llc Multi-region non-chewing gum confectionery composition
US20100152689A1 (en) 2008-12-15 2010-06-17 Andrew Mark Long Physical sensation absorbent article
BRPI1006838B1 (en) 2009-01-15 2019-05-14 Intercontinental Great Brands Llc TREATMENT FOR DISORDER TREATMENT TREATMENT
CN102438463A (en) 2009-01-22 2012-05-02 卡夫食品环球品牌有限责任公司 Confectionery processing
CA2760186C (en) 2009-04-28 2019-10-29 Foamix Ltd. Foamable vehicle and pharmaceutical compositions comprising aprotic polar solvents and uses thereof
EP2445894B1 (en) 2009-06-22 2016-03-02 Segetis, Inc. Ketal compounds and uses thereof
CA2769677A1 (en) 2009-07-29 2011-02-03 Foamix Ltd. Non surface active agent non polymeric agent hydro-alcoholic foamable compositions, breakable foams and their uses
CA2769625C (en) 2009-07-29 2017-04-11 Foamix Ltd. Non surfactant hydro-alcoholic foamable compositions, breakable foams and their uses
US8945516B2 (en) 2009-10-02 2015-02-03 Foamix Pharmaceuticals Ltd. Surfactant-free water-free foamable compositions, breakable foams and gels and their uses
US9849142B2 (en) 2009-10-02 2017-12-26 Foamix Pharmaceuticals Ltd. Methods for accelerated return of skin integrity and for the treatment of impetigo
EP2485601A4 (en) 2009-10-08 2014-08-13 Intercontinental Great Brands Llc Co-extruded layered candy and gum apparatus and methods
US9247761B2 (en) * 2009-10-30 2016-02-02 Intercontinental Great Brands Llc Sugar free confectionery; methods of making same; and use in preparing multilayered confectionery
DE102010002558A1 (en) 2009-11-20 2011-06-01 Symrise Ag Use of physiological cooling agents and agents containing such agents
US20130052307A1 (en) 2009-12-21 2013-02-28 Cesar Carlos Elejalde Particulate coating compositions, coated confectionery, and methods of making the same
JP5643341B2 (en) 2010-01-21 2014-12-17 インターコンチネンタル グレート ブランズ エルエルシー Systems and methods for forming and sizing chewing gum and / or systems and methods for changing chewing gum temperature
GB201004890D0 (en) 2010-03-23 2010-05-05 Cadbury Uk Ltd Confectionery product containing active and/or reactive components and methods of production thereof
WO2011139943A1 (en) 2010-05-03 2011-11-10 Kraft Foods Global Brands Llc Natural chewing gum including cellulose materials
CN102970967A (en) 2010-05-10 2013-03-13 赛格提斯有限公司 Fragrant formulations, methods of manufacture thereof and articles comprising the same
MX2012013889A (en) 2010-06-02 2013-02-15 Nihon Kraft Foods Ltd Multi-region confectionery.
EP2584911A1 (en) 2010-06-25 2013-05-01 Kraft Foods Global Brands LLC Enhanced release of lipophilic ingredients from chewing gum with hydrocolloids
BR112013001142A2 (en) 2010-07-19 2016-05-17 Procter & Gamble compositions comprising derivatives of essential oil compounds and use in personal care products
CN103140142B (en) 2010-07-30 2015-09-23 洲际大品牌有限责任公司 A kind of delivery system for active component as comestible composition part
US20120035376A1 (en) 2010-08-03 2012-02-09 Segetis, Inc. Methods for the manufacture of acetals and ketals, and the acetals and ketals produced thereby
EP2603836A4 (en) 2010-08-12 2017-08-02 Segetis, Inc. Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof
CN103052691B (en) 2010-08-12 2014-05-28 赛格提斯有限公司 Latex coating compositions including carboxy ester ketal coalescents, methods of manufacture, and uses thereof
WO2012033813A2 (en) 2010-09-07 2012-03-15 Segetis, Inc. Compositions for dyeing keratin fibers
EP2613649A1 (en) 2010-09-09 2013-07-17 Kraft Foods Global Brands LLC Chewing gum compositions providing flavor release profiles
WO2012037122A2 (en) 2010-09-13 2012-03-22 Segetis, Inc. Fabric softener compositions and methods of manufacture thereof
AU2011308857B2 (en) 2010-10-01 2015-11-05 The Procter & Gamble Company Oral care compositions with improved flavor
EP2630205A4 (en) 2010-10-18 2015-01-21 Segetis Inc Water reducible coating compositions including carboxy ester ketals, methods of manufacture, and uses thereof
JP5989009B2 (en) 2011-02-14 2016-09-07 インターコンチネンタル グレート ブランズ エルエルシー Confectionery with multiple flavors and multiple textures
CA2825543C (en) 2011-02-23 2016-01-19 Intercontinental Great Brands Llc Flavor pre-blends for chewing gum, methods of making flavor pre-blends and chewing gum compositions thereof
CA2829351A1 (en) 2011-03-11 2012-09-20 Intercontinental Great Brands Llc System and method of forming multilayer confectionery
JP5856288B2 (en) 2011-04-29 2016-02-09 インターコンチネンタル グレート ブランズ エルエルシー Encapsulated acid, method for preparing encapsulated acid, and chewing gum containing encapsulated acid
JP2014524901A (en) 2011-06-13 2014-09-25 ザ プロクター アンド ギャンブル カンパニー Personal care compositions containing diamide gelling agents and methods of use
CN104039396A (en) 2011-06-13 2014-09-10 宝洁公司 PERSONAL CARE COMPOSITIONS COMPRISING A pH TUNEABLE GELLANT AND METHODS OF USING
CA2839992C (en) 2011-06-20 2016-10-04 The Procter & Gamble Company Personal care compositions comprising shaped abrasive particles
CN108925737A (en) 2011-07-21 2018-12-04 洲际大品牌有限责任公司 The system and method for being used to form and cooling down chewing gum
WO2013013045A2 (en) 2011-07-21 2013-01-24 Kraft Foods Global Brands Llc Advanced gum forming
RU2585462C2 (en) 2011-07-21 2016-05-27 ИНТЕРКОНТИНЕНТАЛ ГРЕЙТ БРЭНДЗ ЭлЭлСи Methods of moulding chewing gum and caramel confectionery material (versions)
US20130042482A1 (en) 2011-08-16 2013-02-21 Valerie Jean Bradford Skin Engaging Member Comprising An Anti-Irritation Agent
ES2689171T3 (en) 2011-09-01 2018-11-08 The Procter & Gamble Company Compositions for oral care with improved rheology
WO2013041621A1 (en) 2011-09-20 2013-03-28 Basf Se Low molecular weight modulators of the cold-menthol receptor trpm8 and use thereof
JP2013195289A (en) 2012-03-21 2013-09-30 Takasago Internatl Corp Method for evaluating sense stimulating component
EP3666084A1 (en) 2012-04-20 2020-06-17 Intercontinental Great Brands LLC System and method for manufacturing chewing gum
WO2013170433A1 (en) 2012-05-15 2013-11-21 The Procter & Gamble Company Absorbent article having characteristic waist end
US20130315843A1 (en) 2012-05-25 2013-11-28 The Procter & Gamble Company Composition for reduction of trpa1 and trpv1 sensations
US9271912B2 (en) 2012-06-13 2016-03-01 The Procter & Gamble Company Personal care compositions comprising a pH tuneable gellant and methods of using
ES2710513T3 (en) 2012-06-19 2019-04-25 Intercontinental Great Brands Llc Uncoated chewing gum, packed in bulk
EP2695597B1 (en) 2012-08-07 2019-07-24 Symrise AG Cosmetic compositions
RU2015106110A (en) 2012-08-22 2016-10-20 Интэрконтинентал Грэйт Брэндс Ллс COMPOSITIONS OF CHEWING RUBBER AND METHODS OF THEIR MANUFACTURE
EP2897468B1 (en) 2012-09-21 2017-11-08 Intercontinental Great Brands LLC Advanced gum forming
US9458414B2 (en) 2012-09-21 2016-10-04 Gfbiochemicals Limited Cleaning, surfactant, and personal care compositions
SG11201501430VA (en) 2012-09-28 2015-03-30 Gillette Co A skin engaging member comprising at least one thermally resilient sensate
WO2014052389A2 (en) 2012-09-28 2014-04-03 The Gillette Company A skin engaging shaving aid member comprising at least one thermally resilient sensate
JP2016506383A (en) 2012-11-29 2016-03-03 サジティス・インコーポレイテッド Carboxyester ketal, process for its production and use
WO2014128566A2 (en) 2013-02-21 2014-08-28 Mondelez International Chewing gum and methods of making thereof field
BR122016000483A2 (en) 2013-03-29 2018-06-19 Intercontinental Great Brands Llc SUGAR-FREE LIQUID EDIBLE COMPOSITION AND PASTA PRODUCT OR MEDICINAL PRODUCT
JP2016514487A (en) 2013-04-17 2016-05-23 インターコンチネンタル グレート ブランズ エルエルシー System and method for making a chewing gum product comprising at least one ingredient
CN105283082A (en) 2013-05-31 2016-01-27 洲际大品牌有限责任公司 Chewing gum with hard, amorphous inclusions and methods of making thereof
WO2015051056A1 (en) 2013-10-02 2015-04-09 Intercontinental Great Brands Llc Particulate coated chewing gum and confectionery; and methods of making the same
US9884130B2 (en) 2013-11-13 2018-02-06 The Procter & Gamble Company Compositions for delivery of oral comfort sensations
EP3110510A1 (en) 2014-02-27 2017-01-04 The Procter & Gamble Company Oral care compositions with a reduced bitter taste perception
JP2017508449A (en) 2014-02-28 2017-03-30 インターコンチネンタル グレート ブランズ エルエルシー Edible core coatings, coating systems and processes, and coated products made therefrom
US10334867B2 (en) 2014-03-03 2019-07-02 Intercontinental Great Brands Llc Method for manufacturing a comestible
US20150273711A1 (en) 2014-03-26 2015-10-01 The Gillette Company Razor Comprising A Molded Shaving Aid Composition Comprising A Thermally Resilient Sensate
US20150272847A1 (en) 2014-03-26 2015-10-01 The Gillette Company Skin Engaging Shaving Aid Comprising A Thermally Resilient Sensate And A TRPA1 Receptor Inhibitor
AU2015249706A1 (en) 2014-04-23 2016-11-03 The Procter & Gamble Company Cyclohexanecarboxamide with cooling properties
EP3142494A1 (en) 2014-05-15 2017-03-22 Intercontinental Great Brands LLC Multi-textured chewing gum and methods of making thereof
WO2015195534A2 (en) 2014-06-16 2015-12-23 Intercontinental Great Brands Llc Degradable chewing gum
BR112017002061A2 (en) 2014-08-15 2017-12-26 Procter & Gamble oral treatment compositions and regimens
CN106659650A (en) 2014-08-15 2017-05-10 宝洁公司 Oral care compositions with an enhanced sensory experience
CN111939090A (en) 2014-08-15 2020-11-17 宝洁公司 Dentifrice with extending chemical
KR20170070196A (en) 2014-11-26 2017-06-21 더 질레트 컴퍼니 엘엘씨 A skin engaging member comprising ethylene vinyl acetate
FR3029777B1 (en) 2014-12-15 2019-11-29 L'oreal USE OF THE ASSOCIATION OF AN ASSOCIATIVE NON-IONIC POLYURETHANE POLYETHER AND A CYCLOHEXANOL DERIVATIVE AS A SKIN-REFRESHING AGENT
WO2016105879A1 (en) 2014-12-22 2016-06-30 Intercontinental Great Brands Llc Confectionery and multi-layer chewing gum confectionery composition and article
US9951295B2 (en) 2015-02-19 2018-04-24 The Procter & Gamble Company Compositions for deposition on biological surfaces
CA2976512A1 (en) 2015-02-27 2016-09-01 Kimberly-Clark Worldwide, Inc. Absorbent article leakage assessment system
ES2736875T3 (en) 2015-03-04 2020-01-08 Symrise Ag Compositions comprising menthol compounds as calming agents
CN107532063B (en) 2015-03-25 2020-03-10 高砂香料工业株式会社 Methylmenthol derivative and cold-sensitive composition containing the same
EP3280411B1 (en) 2015-04-09 2020-02-19 The Procter and Gamble Company Reduction in cpc taste aversion by reducing cpc activation of trpa1 receptors, tprv1 receptors, or both
AU2016316869B2 (en) * 2015-08-31 2020-09-10 Kimberly-Clark Worldwide, Inc. Article of commerce treated with sublimable material
BR112018006735A2 (en) 2015-10-22 2018-10-16 Procter & Gamble chromatographic separation method
MX2018004814A (en) 2015-10-22 2019-04-01 Procter & Gamble Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products.
EP3390352A1 (en) 2015-12-18 2018-10-24 The Procter and Gamble Company Synthesis of cyclohexane ester derivatives useful as sensates in consumer products
EP3435958A1 (en) 2016-04-01 2019-02-06 The Procter and Gamble Company Oral care compositions containing a gel network phase and potassium nitrate
MX2018011991A (en) 2016-04-01 2019-02-13 Procter & Gamble Oral care compositions with an effective flavor display.
MX2018011989A (en) 2016-04-01 2019-02-13 Procter & Gamble Oral care compositions containing a gel network phase.
AU2017240032B2 (en) 2016-04-01 2019-07-18 The Procter & Gamble Company Oral care compositions containing gel networks and potassium nitrate
WO2017173272A1 (en) 2016-04-01 2017-10-05 The Procter & Gamble Company Oral care compositions containing potassium nitrate and peroxide
US20170334082A1 (en) 2016-05-18 2017-11-23 The Gillette Company Llc Skin Engaging Member Comprising Ethylene Vinyl Acetate
CA2978573A1 (en) 2016-09-08 2018-03-08 Foamix Pharmaceuticals Ltd. Compositions and methods for treating rosacea and acne
WO2018081190A1 (en) 2016-10-25 2018-05-03 The Procter & Gamble Company Fibrous structures
US20180117780A1 (en) 2016-11-03 2018-05-03 The Gillette Company Llc Skin engaging member comprising ethylene vinyl acetate
BR112019009754B1 (en) 2016-11-17 2022-11-22 The Gillette Company Llc SKIN CONTACT MEMBERS COMPRISING ETHYLENE VINYL ACETATE AND A FRAGRANCE
MX2019008278A (en) 2017-01-10 2019-09-09 Takasago Perfumery Co Ltd Methylmenthol derivative and cool-sensation imparter composition containing same.
MX2019008796A (en) 2017-02-06 2019-09-26 Intercontinental Great Brands Llc Dual-textured confectionery; and methods of making the same.
US11013641B2 (en) 2017-04-05 2021-05-25 Kimberly-Clark Worldwide, Inc. Garment for detecting absorbent article leakage and methods of detecting absorbent article leakage utilizing the same
DK3850950T3 (en) 2017-06-05 2024-01-15 Perfetti Van Melle Benelux B V Chewing gum compositions and methods of making the same
EP4256969A3 (en) 2017-08-18 2024-03-06 Perfetti Van Melle Benelux B.V. Chewing gum compositions and methods of making thereof
WO2019043164A1 (en) 2017-08-31 2019-03-07 Basf Se Use of physiological cooling active ingredients, and compositions comprising such active ingredients
WO2019078185A1 (en) 2017-10-16 2019-04-25 高砂香料工業株式会社 Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative
WO2019241146A1 (en) 2018-06-11 2019-12-19 Seattle Gummy Company Low glycemic gummy composition and methods of making and using thereof
EP3806657A4 (en) 2018-06-14 2022-03-30 Seattle Gummy Company Low glycemic composition and methods of making and using thereof
AU2019365078B2 (en) 2018-10-26 2022-08-18 Intercontinental Great Brands Llc Center-filled confectionery product; coated product; and methods of making
EP3689324A1 (en) 2019-02-04 2020-08-05 Symrise AG New cooling agents and preparations comprising them
MX2022001381A (en) 2019-08-14 2022-03-25 Intercontinental Great Brands Llc Confectionery chip product; and methods of making the same.
CN111004224B (en) * 2019-12-11 2021-03-12 中国烟草总公司郑州烟草研究院 Cyclomethine compound, synthesis method and application thereof, and tobacco product
MX2023003549A (en) 2020-09-28 2023-04-21 Procter & Gamble Oral care composition comprising hops and flavor.
MX2023003711A (en) 2020-10-09 2023-04-21 Intercontinental Great Brands Llc Unwrapped hard candy product; isomalt confectionery; method of making and use thereof.
WO2022105986A1 (en) 2020-11-17 2022-05-27 Symrise Ag Novel cooling agents and preparations containing same
US20220370334A1 (en) 2021-05-11 2022-11-24 The Procter & Gamble Company Oral Care Compositions Comprising Block Copolymer
WO2023143741A1 (en) 2022-01-28 2023-08-03 Symrise Ag New coolants, and preparations containing same
WO2023248187A1 (en) 2022-06-24 2023-12-28 Nicoventures Trading Limited Oral composition comprising a receptor modulator
WO2022207944A2 (en) 2022-07-11 2022-10-06 Symrise Ag Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL295574A (en) * 1962-08-03
US3349150A (en) * 1962-08-03 1967-10-24 Carlisle Chemical Works Polyether diphosphonates
US3257480A (en) * 1962-08-03 1966-06-21 Carlisle Chemical Works Acetal and ketal phosphites
US3206474A (en) * 1962-08-03 1965-09-14 Carlisle Chemical Works Acetal and ketal phosphonates
US3830930A (en) * 1969-05-14 1974-08-20 Nickstadt Moeller Inc Labial compositions containing menthyl keto esters
DE2022369B2 (en) * 1970-05-08 1972-03-02 Joh Andre Sebald GmbH, 3200 Hildes heim Cosmetic products and room sprays contain 1 Menthyl ethyl carbonate
US4150052A (en) * 1971-02-04 1979-04-17 Wilkinson Sword Limited N-substituted paramenthane carboxamides
PH10359A (en) * 1971-02-04 1977-01-05 Wilkinson Sword Ltd N-substituted-p-methane-3-carboxamides having physiological cooling activity and compositions containing them
US4136163A (en) * 1971-02-04 1979-01-23 Wilkinson Sword Limited P-menthane carboxamides having a physiological cooling effect
US4178459A (en) * 1971-02-04 1979-12-11 Wilkinson Sword Limited N-Substituted paramenthane carboxamides
US4190643A (en) * 1971-02-04 1980-02-26 Wilkinson Sword Limited Compositions having a physiological cooling effect
US4193936A (en) * 1971-02-04 1980-03-18 Wilkinson Sword Limited N-substituted paramenthane carboxamides
US4157384A (en) * 1972-01-28 1979-06-05 Wilkinson Sword Limited Compositions having a physiological cooling effect
US4059118A (en) * 1972-01-28 1977-11-22 Wilkinson Sword Limited Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity
US4033994A (en) * 1972-01-28 1977-07-05 Wilkinson Sword Limited Substituted p-menthanes
US4153679A (en) * 1972-04-18 1979-05-08 Wilkinson Sword Limited Acyclic carboxamides having a physiological cooling effect
GB1421743A (en) * 1972-04-18 1976-01-21 Wilkinson Sword Ltd Ingestible topical and other compositions
CA1027347A (en) * 1972-07-20 1978-03-07 David G. Rowsell Compounds having a physiological cooling effect and compositions containing them
GB1436329A (en) * 1972-08-07 1976-05-19 Unilever Ltd Esters of menthol and a heterocyclic carboxylic acid and their use in cosmetic preparations
GB1434728A (en) * 1972-09-27 1976-05-05 Wilkinson Sword Ltd Compositions and articles containing phospine oxides having a physiological cooling effect and phosphine oxides for use therein
US4070449A (en) * 1972-10-24 1978-01-24 Wilkinson Sword Limited Compounds having a physiological cooling effect and compositions containing them
GB1422998A (en) * 1973-03-22 1976-01-28 Wilkinson Sword Ltd Cyclohexanecarboxamides having a physiological cooling effect and compositions containing them
US4296093A (en) * 1973-04-16 1981-10-20 Wilkinson Sword Limited Cyclic carboxamides having a physiological cooling effect
LU68016A1 (en) * 1973-07-13 1975-04-11
DE2608226A1 (en) * 1976-02-28 1977-09-08 Haarmann & Reimer Gmbh AGENTS WITH PHYSIOLOGICAL COOLING EFFECT
JPS5888334A (en) * 1981-11-20 1983-05-26 Takasago Corp 3-l-menthoxypropane-1,2-diol
DK0485170T3 (en) * 1990-11-06 1995-12-11 Wrigley W M Jun Co Improved taste using menthon catals

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6303817B1 (en) 2000-08-10 2001-10-16 International Flavors & Fragrances Inc. Method for making amides
US6437183B1 (en) 2000-08-10 2002-08-20 International Flavors & Fragrances Inc. Method for making amides
US7025997B2 (en) 2003-09-24 2006-04-11 International Flavors & Fragrances Inc. Coolant plant extract compositions containing monomenthyl succinate

Also Published As

Publication number Publication date
JPH05125073A (en) 1993-05-21
DE59202585D1 (en) 1995-07-27
US5266592A (en) 1993-11-30
IE921084A1 (en) 1992-10-07
DK0507190T3 (en) 1995-10-09
EP0507190B1 (en) 1995-06-21
AU653999B2 (en) 1994-10-20
JP3071030B2 (en) 2000-07-31
EP0507190A1 (en) 1992-10-07
AU1390992A (en) 1992-10-08
ATE123936T1 (en) 1995-07-15
ES2073205T3 (en) 1995-08-01
IE67879B1 (en) 1996-05-01
DE4110973A1 (en) 1992-10-08

Similar Documents

Publication Publication Date Title
CA2064918A1 (en) Compositions having a physiological cooling effect and active compounds suitable for these compositions
US5626852A (en) Composition containing body activated fragrance for contacting the skin and method of use
US4828849A (en) Surfactant inhibition of dental plaque
JP3304219B2 (en) Sustained release fragrance composition for human body surface
EP1838652A1 (en) Novel odorant compounds, synthesis method, and uses of said compounds
JP2000351987A (en) Substituted phenols as pfrfume, flavor and antimicrobial compound
EP2442783B1 (en) Novel deodorising compositions and deodorising products containing same
EP1167362A1 (en) Fragance precursors
CA1337299C (en) Perfumery materials
JP5579255B2 (en) Acetal as a scented ingredient
US6440400B1 (en) Trimethylcylohexane derivatives and melanin-formation inhibitors and perfumeholding agents with the use of the same
EP2904080A2 (en) Flavor and fragrance formulation (i)
US7816566B2 (en) p-Menthan-3-ol alkylated derivatives and their use as refreshing agents
JP2002542382A (en) Pre-fragrance
EP1687291A2 (en) Novel cyclic oxygenated compounds having cooling, fragrance, and flavor properties, and uses thereof
US4606849A (en) Perfumery compositions
US4623537A (en) Oral hygiene compositions
EP1458705B1 (en) Thiophene derivatives and their use as fragrants
EP1773284A1 (en) Beta-substituted tetrahydropyran(on)s and method for the synthesis and the use thereof
Elmorsy et al. Use of reductive properties of iodotrichlorosilane II: chemoselective reduction of α, β-unsaturated ketones and nitriles
EP0522965A1 (en) Oral composition to reduce or eliminate bad breath and process of oral hygiene for eliminating bad breath
JPH01128994A (en) Methyl-4,6-0-alkylidene-d-glycoside
US7138368B2 (en) Sesquiterpene oxides as perfuming and flavoring agents
JP2546263B2 (en) Bad breath remover
JPH027931B2 (en)

Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued