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Publication numberUS2438091 A
Publication typeGrant
Publication dateMar 16, 1948
Filing dateSep 6, 1943
Priority dateSep 6, 1943
Publication numberUS 2438091 A, US 2438091A, US-A-2438091, US2438091 A, US2438091A
InventorsLynch Kathryn L
Original AssigneeAmerican Cyanamid Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Aspartic acid esters and their preparation
US 2438091 A
Abstract  available in
Images(4)
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Claims  available in
Description  (OCR text may contain errors)

Patented Mar. 16, 1948 ASPARTIC ACID ESTERS AND THEIR PREPARATION Kathryn L. Lynch, Stamford, Comm, assignmto American .Cyanamid Company, New York,

N. Y., a corporation of Maine No Drawing.

Application September 6, 1943, Serial No. 501,417

Claims. -(CL 260-482) This invention relates to N-substituted aspartic acid esters and to their preparation. The invention includes the new compounds themselves, the novel method by which they are prepared and also compositions containing them.

I have found that primary alkyl and primary alkoxyalkyl amines may be caused to react with certain maleic acid esters to be hereinafter described to yield N-alkyl and N-alkoxyalkyl substituted aspartic acid esters having the general formula:

the

in which R and R1 are members of the group consisting of hydrogen and alkyl radicals of from 1 to 3 carbon atoms, R2 and Rs are alkyl radicals of from 1 to 18 carbon atoms and R4 is a member of the group consisting of alkyl and alkoxyalkyl radicals. The alkyl radicals, R2 and R3, may be interrupted, terminated or substituted with various types and kinds of substituent groups.

Many of the compounds of this class, particularly those which have in the R2, R3 and R4 positions a long chain hydrophobe group and a short chain group are cationically surface active in the form of their acid salts and possess wetting, foaming and detergent properties. The hydrophobe group may be a long chain alkyl or alkoxyalkyl group of about six or more carbon atoms and may be positioned at any of R2, R3 or R4 in the general formula above.

Although the compounds of the present invention may be used in the form of their acid salts as surface active agents, they are of greatest value as intermediates in the preparation of a class of superior wetting agents and detergents described and claimed in my copending application, Serial No. 501,851, filed September 10, 1943.

When used as intermediates in this process at least one of the groups R2, R3 or R4 should be a hydrophobe alkyl or alkoxyalkyl radical having four or more carbon atoms. Of course, one or two of the groups R2, R: or R4 may be a short chain alkyl. or alkoxyalkyl radical provided that the requisite number of carbon atoms is present in the molecule to give a portion thereof having hydro- 2 phobic properties sumciently strong to orient themolecule at an oil-water interface. In order that this condition may be met the total number of carbon atoms in R2, R3 and R4 should be at least twelve.

The compounds vary in physical character from oily liquids to hard wax-like materials. The compounds are in general colorless but some are pale yellow to light brown in color. Those compounds of low molecular weight are soluble in water and very readily soluble in aqueous solutions of acids. As the length of the substituent chains increases, however, the compounds become more dimcultly soluble in water but may. be dissolved in aqueous acids, mineral spirits, alcohols, and other organic solvents.

Although it would be expected in a reaction involving a maleic acid ester with a primary amine that the ester groups would be hydrolyzed with the formation of amides, I have found that by following the procedure to be described hereinafter the primary amine may be caused to react at the double bond of the maleic acid ester to form N- substituted aspartic acid esters directly in substantially quantitative yield. As a result of my studies of the reaction I have discovered that when a primary amine is mixed with a maleic acid ester of the type described hereinafter a number of difl'erent reactions may occur simultaneously at different rates depending upon the temperature of the reaction mass and the relative proportions of the reactants. At temperatures within the range of 10-100 C. the principal reaction involves the addition of the primary. amine at the double bond of the maleic acid ester with the formation of N-substituted aspartic acid esters. A second and concurrent reaction involves the conversion of unreacted maleic acid ester to the corresponding fumaric acid ester. The third, a much slower reaction, involves the reaction of the primary amine with the fumaric acid ester. A fourth reaction involves the reaction of the aspartic acid ester with itself to form undesirable by-products such as diketo piperazine derivatives. This latter reaction occurs principally at elevated temperatures and upon heating the reac tion mixture for long periods of time.

During the early stages of the reaction the addition of the primary mine to the maleic acid ester is rapid, an approximately 50% yield of diethyl I through replacement of the ester groups.

N-octadecyl aspartate being obtained in 80 minutes upon reacting octadecyl amine with diethyl maleate at 20 C. At higher temperatures the reaction proceeds even faster. The conversion of the maleate ester to the fumarate ester is also fairly rapid during the early stages of the reaction. Since as stated'before the reaction of the primary amine with the fumarate ester is quite slow, it will be seen that the evenual completion of the.reaction to form N-substituted aspartic acid esters depends to a considerable'extent upon 'the amount of fumarate ester formed. As high temperatures favor the conversion of the maleic acid ester to the fumaric acid ester more than they favor the reaction of the primary amine with maleic acid ester it is desirable that the reaction be conducted at low temperatures, preferably less than about 50 C., in the early stages of the reaction. This is desirable in order to secure the formation of N-substituted aspartic acid esters from the maleic acid ester in as high yields as possible, while the maleic acid ester remains as such in the reaction mixture. After holding the reaction mixture at relatively low temperatures until the maleic acid ester has either reacted with the primary amine or has been converted to the corresponding fumaric acid ester, the tempera.- ture may be raised thereby allowing the reaction of the' primary amine and the fumaric acid ester to proceed more rapidly with the formation of N-substituted aspartic acid esters.

Another important factor which enables me to obtain N-substituted aspartates of high purity and in good yield relates to the proportions of reactants used. I have found that the use of more than the theoretical quantity of primary alkyl or primary alkoxyalkyl amine necessary to react with the maleic acid esters at the double bond position results in the formation of amides Accordingly I employ an equal molecular proportion of the maleic acid ester or a slight excess thereof with each mole of primary amine.

From the foregoing it will be seen that my new method comprises the steps of reacting a primary alkyl amine or a primary alkoxyalkyl amine with at least a stoichiometric proportion of maleic acid ester at temperatures not in excess of about 100 C. Preferably I carry out the first phase of the reaction at temperatures not in excess of about 50 C. until substantially all of the maleic acid ester has reacted with the primary amine to yield the corresponding N-substituted aspartic acid ester. I then allow the mixture to react at temperatures not in excess of about 100 C. until substantially all of the primary amine has reacted with the fumarate ester formed from the maleic ester. This procedure avoids the formation of amides and all undesirable by-products which result from side reactions when the reaction is attempted at high temperature. As a result I obtain N-substituted aspartic acid esters of excellent purity with yields as high as theoretical.

The reaction may be carried out by simply mixing a suitable primary alkyl or primary alkoxy alkyl amine with a maleic acid ester and allowing the mixture to stand at room temperatures until reaction is complete. In most cases it is desirable, however, to carry out the reaction with the reactants dissolved in a suitable solvent such as an alcohol, mineral spirits, toluene, ethers, dioxane, etc. Since the reaction is,exothermic in character, it is generally advisable to add one of the reactants to the other slowly in small proportions to prevent an excessive rise in the tem- 4 perature of the reaction mixture. The reactionmixture is then allowed to stand until the reaction is substantially complete. Towards the end of the reaction period the reactants may be heated up to about C. for a short time to hasten completion of the reaction. As stated before, however, use of high temperatures for extended periods of time is to be avoided if a product of high purity is to be obtained.

The maleic acid esters which may be employed in the reaction described herein are those having the general formula:

in which R and R1 are members of the group consisting of hydrogen and alkyl radicals of from 1 to 3 carbon atoms, R: and R: are alkyl radicals of from 1 to 18 carbon atoms. The alkyl radicals, R: and R3, may be interrupted, terminated or substituted with various types and kinds of substituent groups. Specific examples of the maleic acid esters that may be employed in my invention are diethyl maleate, diamyl maleate, dibutyl maleate, dicapryl maleate, di (methyl amyl) maleate, d1 (ethyl hexyl) maleate, di-n-hexyl maleate, didecyl maleate, dioctyl ethyl maleate, di-hexylcitraconate, dicapryl pyrocinchonate, di-ethyl itaconate, h'exyl octyl maleate, diglycol maleate, dicyclohexyl maleate, di (2 cyclohexyl ethyl) maleate, and the like.

Primary alkyl and primary alkoxyalkyl amines which may be employed in my process include those such as butyl amine, amyl amine, octyl amine, dodecyl amine, octadecyl amine, methoxypropyl amine, ethoxypropyl amine, amoxypropyl amine, dodecoxypropyl amine and others of similar character.

The invention will now be illustrated in greater detail by means of the following specific examples. It should be understood that although these examples may describe in detail some of the more specific features of the present invention they are given primarily by way of illustration and the invention in its broader aspects in not to be limited thereto.

EXAMPLE 1 g. (1 mol) dimethyl maleate was added slowly with stirring to a solution of 265 g. (1 mol) of octadecyl amine in 500 cc. of tertiary butanol at 50 C. After standing at 28 C. for 10 hours the formation of dimethyl N-octadecyl aspartate was 91.2% complete. After standing 43 hours the reaction was 94.5% complete and after 65 hours was 96.2% complete.

EXAMPLEZ 900 g. (5 mols+5% excess) of diethyl maleate was added slowly with stirring to a solution of 1325 g. (5 mols) of technical octadecyl amine in 1500 cc. of tertiary butanol. After standing 17 hours at room temperature the condensation was 91.2% complete and after standing 50 hours it was 95.5% complete.

Reaction between diethyl maleate and octadecyl amine to form diethyl N-octadecyl aspartate was caused to take place at different temperatures and the course of the reaction followed by taking samples of the reaction mixture from time to time. The results of this series of experiments 75 are given in the following table.

Tm: Aspartate formatiorh-percent completion Time Temperature 1 Hour 1% Hours 3 Hours Per cent Per cent From the above it will be seen that the reaction proceeds rapidly in the earlier stages but requires a considerable period of time for completion even at the higher temperatures. At low temperatures, the reaction will go to approximately 98% of completion if given suilicient time for reaction.

EXAMPLE 3 50 g. of diglycol maleate was added to 66 g. of technical octadecyl amine dissolved in 250 cc. of tertiary butanol. The reaction mixture was kept at 895 C. for 2% hours at the end of which time the formation of diglycol noctadecyl aspartate was 82.5% complete. The reaction mixture was allowed to stand at 895 C. for 29.5 hours and then at 25 C. for 48 hours at which time the reaction was 96% complete. The product was an almost colorless pasty mass.

EXAMPLE 4 51.2 parts of diamyl maleate was stirred with 20.6 parts of ethoxypropyl amine at 26 C. The temperature of the reaction mass rose to 47 C. as the mixture was being stirred. Within 10 to 15 minutes diamyl N-ethoxypropyl asparate had been formed to such an extent that the product was soluble in dilute hydrochloric acid to give a foaming and wetting solution. The product was a colorless oil-like liquid.

EXAMPLE 20 parts. by weight of diisopropyl maleate was added slowly with stirring to 28 parts by weight or technical octadecyl amine dissolved in 39 parts by weight of tertiary butanol. The mixture was allowed to stand at room temperature for 113 hours at the end of which time the formation of diisopropyi n-octadecyl asp'artate was 95% complete.

EXAMPLE c 14.6 parts by weight of butyl amine was added to 68 parts by weight of dioctyl maleate at 24 C. In less than 2 minutes the temperature of the reaction mass had risen to 64 C. A clear colorless oil was obtained which was slightly soluble in dilute hydrochloric acid to give aqueous solutions having wetting and foaming properties.

ELE 7 57.6 g. (0.4 mol) of dimethyl maleate was dissolved in 150 cc. of ethanol. 51.6 g. (0.4 mol) of octyl amine was then added to the solution while keeping the temperature of the reaction mass below 49 C. by cooling. After allowing the mixture to stand at 28 C. for one hour dimethyl fumarate separated from the liquid as a solid. The mixture was filtered and 13 g. of dimethyl fumarate was obtained. The filtrate containing dimethyl N-octyl aspartate was very soluble in dilute hydrochloric acid solution to give a slightly roaming and wetting solution.

EXAMPLE 9 To a solution of 23 g. (0.2 mol) of n-heptylamine in 30 ml. of t-butanol was added 46 g. (0.2 mol) of dibutyl maleate and the mixture allowed to stand at room temperature. The reaction was more than 99% complete in seventy hours. The t-butanol was then removed by heating under reduced pressure until the temperature of the residual liquid rose to -100 C. There was obtained 69 g., a 99% yield of dlbutyl N-nheptylaspartate.

\EXAMPLE 10 To a solution of 15 g. (0.2 mol) of n-butylamine in 30 ml. of t-butanol was added 68 g. (0.2 mol) of di-n-octyl maleate and the mixture allowed to stand at room temperature. In seventytwo hours reaction had taken place to the extent of and was more than 99% complete in ninety hours. The t-butanol was then removed by heating the solution under reduced pressure until the temperature of the residue rose to 90-100 C. The yield was 82 g., a 99% yield of theoretical of di-n-octyl N-n-butylaspartate.

EXABTPLE 11 To 34 g. (0.08 mol) of di-undecyl maleate was added 25 ml. of t-butanol solution containing 0.08 mol of methylamine and the mixture was allowed to stand at room temperature. The reaction was more than 99% complete in sixtyseven hours. The t-butanol was evaporated by heating under reduced pressure until the temperature of the *residual liquid reached 110 C. After cooling, the yellow oily liquid was filtered to remove a small amount of white solid which separated. The yield was 30 g., a 82% yield of di-undecyl N-methylaspartate.

To 43 g. (0.2 mol) of n-tetradecylamine dissolved in 50 ml. of t-butanol was added 35 g. (0.2 mol) of diethyl maleate and the solution was allowed to stand at room temperature. The reaction was more than 99% complete in sixty-eight hours. The t-butanol was evaporated under reduced pressure with heating until the temperature of the liquid residue rose to 90-100" C.

There was obtained 77 g., a 98% yield of diethyl N-n-tetradecylaspartate.

To a solution of 18 g. (0.2 mol) of -y-methoxypropylamine in 300 ml. of t-butanol was added 57 g. (0.2 mol) of di-n-hexyl maleate and the mixture allowed to stand at room temperature. In seventy-two hours, the reaction was more than 99% complete. The t-butanol was evaporated by heating under reduced pressure until the temperature of the residual liquid rose to 90-100 C. There was obtained 75 g., a 100% yield, of di-n- 7 hexyl N-methoxypropylaspartate, a slightly yellow oily liquid To a solution of 50 g. (0.27 mol) of n-dodecylamine in 40 ml. of t-butanol was added 89 g. (0.27 mol) of dimethyl maleate. The mixture was allowed to stand at room temperature. The addition was found to be more than 99% comlete in sixty-nine hours. The t-butanol was evaporated by heating under reduced pressure until the temperature of the liquid residue rose to 90-l00 C. There was obtained 87 g., a 98% yield, of dimethyl N-n-dodecylaspartate.

EXAIMPLE 15.

To 81 g. (0.47 mol) of diethylmaleate was added at once 148 m1. of a t-butanol solution containing 0.47 mol of methylamine with cooling in a water bath. There was a noticeable heat of reaction. The addition was 91% complete in one hour. and in nineteen hours at room temperature, the addition was more than 99% complete. The t-butanol was evaporated under reduced pressure with heating until the residue reached a temperature of 100-110 C. There was obtained 93 g., a 98% yield, of diethyl N-methylaspartate.

The surface active characteristics of the products of the last flve examples are given in the table below in terms of their wetting power as measured by the standard Draves test. The wetting power is expressed as the number of seconds required for a 5.5 g. gray cotton skein attached to a 1.5 g. hook to sink in a designated concentration of the surface active agent in water. The

compounds were tested in the form of their 1131- drochloride salt.

As will be seen from the above results the compound diethyl N-methyl aspartate has no wetting power whatever. The reason being that it has no hydrophobe groups as do the other compounds shown above. As stated before the compounds must have a total of at least 12 carbon atoms in the groups R2, R: and R4, if they are to have surface active properties.

The last four compounds in the table, that is the products of Examples 11 to 14, inclusive, also showed a remarkable lowering of the surface tension of water when dissolved therein. As measured by the Du Nuoy tensiometer at 30 0., these four compounds at a concentration of 0.5% lowered the surface tension of distilled water from 71 dynes per centimeter to an average of about 34 dynes whereas diethyl N-methyl aspartate had no appreciable eifect on the surface tension at the same concentration. This latter compound also failed to give foaming solutions at all congeneral formula:

12 0 H-d-l-O-m in which R and R1 are members of the group consisting of hydrogen, and alkyl radicals having 1 to 3 carbon atoms, R: and R: are alkyl radicals of from 1 to 18 carbon atoms and R4 is a member of the group consisting of alkyl and alkoxyalkyl radicals. the total number of carbon atoms in Ra. R: and R4 being at least twelve.

2. Diallwl N-alkyl aspartates having surface active properties said compounds having at least 12 carbon atoms in the alkyl groups thereof.

3. Dialkyl N-alkoxyalkyl aspartates having surface active properties said compound having at least 12 carbon atoms in the alkyl groups thereof.

4. A method of preparing dialkyl esters of N- suhstituted aspartic acid which comprises mixing substantially equal molecular quantities of a primary amine of the group consisting of primary alkyl amines containing at least 4 carbon atoms and primary allromalkyl amines containing at least 4 carbon atoms with a dialkyl ester of maleic acid, allowing the mixture to react at temperatures not in excess of about 50 C. until substantially all of the maleic acid present has reacted with the primary amine, and then heating the mixture at temperatures of 50-100 C. to complete the reaction between the remaining primary amine and the fumarate ester formed from the maleic ester.

5. A method of preparing dialkyl esters of N- substituted aspartic acid which comprises mixing substantially equal molecular quantities of a primary alkyl amine containing 4 to 18 carbon atoms and a dialkyl ester of maleic acid, allowing the mixture to react at temperatures not in excess of about 50 C. until substantially all of the maleic acid ester present has reacted with the primary amine and then heating the mixture at temperatures of 50-100 C. to complete the reaction between the remaining primary amine and the fumarate ester formed from the maleic ester.

KATHRYN L. LYNCH.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,017,537 Hoifmann Oct. 15, 1935 2,200,220 Reppe May 7, 1940 2,317,378 Harris Apr. 27, 1943 2,324,712 Lynch July 20, 1943 OTHER REFERENCES Korner and Menozzi: Gazetta Chimica Italiana," vol. 19, pages 422, 426. 431 (1889)

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2017537 *Aug 11, 1932Oct 15, 1935Ig Farbenindustrie AgProduction of hydroxy-alkylamino carboxylic acid compounds
US2200220 *Jun 3, 1937May 7, 1940Ig Farbenindustrie AgNu-substituted aspartic acids and their functional derivatives and process of producig them
US2317378 *Feb 5, 1941Apr 27, 1943Benjamin R HarrisAntiseptic materials
US2324712 *Sep 25, 1940Jul 20, 1943American Cyanamid CoDialkyl esters of n-substituted aspartic acid and method of preparing the same
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Citing PatentFiling datePublication dateApplicantTitle
US2761874 *Sep 30, 1954Sep 4, 1956Dow Chemical CoAmino derivatives of n-alkyl substituted aspartic acids and their functional derivatives
US2816911 *Feb 23, 1954Dec 17, 1957Gen Mills IncProcess for the preparation of n-alkyl beta-alanines
US2992969 *Dec 10, 1959Jul 18, 1961Earl J RobertsMethod of repelling rodents
US3048615 *Dec 30, 1957Aug 7, 1962Standard Oil CoTertiary alkyl azomethine copolymers
US3048616 *Dec 30, 1957Aug 7, 1962Standard Oil CoTertlary alkyl azomethine copolymers
US3048617 *Dec 30, 1957Aug 7, 1962Standard Oil CoTertiary alkyl azomethine copolymers
US3048618 *Dec 30, 1957Aug 7, 1962Standard Oil CoTertiary alkyl azomethine copolymers
US3119794 *Sep 6, 1960Jan 28, 1964California Research CorpPoly-gamma-esters of optically active glutamic acid
US4133960 *Sep 9, 1977Jan 9, 1979Lever Brothers CompanyNovel ester derivatives of ether polycarboxylic acids and process for making same
US4790932 *Dec 3, 1987Dec 13, 1988Henkel Kommanditgesellschaft Auf AktienN-alkyl and N-alkenyl aspartic acids as co-collectors for the flotation of non-sulfidic ores
US4959409 *Jan 14, 1988Sep 25, 1990The Procter & Gamble CompanyAmino-functional compounds as builder/dispersants in detergent compositions
US5269974 *Sep 1, 1992Dec 14, 1993The Procter & Gamble CompanyLiquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions
US5308526 *Jul 7, 1992May 3, 1994The Procter & Gamble CompanyLiquid personal cleanser with moisturizer
US5332527 *Mar 30, 1993Jul 26, 1994The Procter & Gamble CompanyAmino-functional compounds as builder/dispersants in detergent compositions
US5529739 *Nov 15, 1994Jun 25, 1996Bayer CorporationProcess for the production of molded products using internal mold release agents
US5705147 *Sep 18, 1995Jan 6, 1998Stepan CompanyMethods and compositions for conditioning skin and hair
US5711936 *Jun 5, 1995Jan 27, 1998Whitehill Oral Technologies, Inc.Ultramulsion based ingestible compositions
US5730967 *Jun 5, 1995Mar 24, 1998Whitehill Oral Technologies, Inc.Ultramulsion based skin care compositions
US5733529 *Jun 5, 1995Mar 31, 1998Whitehill Oral Technologies, Inc.Ultramulsion based antigingivitis toothpaste compositions
US5733536 *Jun 5, 1995Mar 31, 1998Whitehill Oral Technologies, Inc.Containing a silicone insoluble in a nonionic surfactant
US6165955 *Mar 6, 1998Dec 26, 2000Rhodia Inc.Oil in water emulsion comprising a mixture of fatty ester or amide, nonionic and amphoteric surfactants, glycol emulsifier; shampoo
US6414189 *Nov 18, 1998Jul 2, 2002Mitsubishi Rayon Co., Ltd.Crystals of [S,S]-ethylenediamine-N,N′-disuccinic acid with high bulk density and method of obtaining the same
US6576702Jul 18, 2001Jun 10, 2003Noveon Ip Holdings Corp.Prepared by reacting a polyisocyanate and an active hydrogen compounds, dispersing the prepolymer in water, and chain extending the prepolymer by reaction with at least one of water, inorganic or organic polyamine, adding a plasticizer
US6630435Jun 27, 2000Oct 7, 2003Procter & GamblePreformed monoperoxycarboxylic acid, tertiary alkyl amine oxide and anionic hydrotrope or surfactant; laundry and hard surfaces; odorless; colorfastness; less damaging; chlorine free
US6660254May 5, 2000Dec 9, 2003Unilever Home & Personal Care Usa, Division Of Conopco, Inc.Leave-in foaming composition for conditioning, lightening and highlighting hair
US6677294Nov 29, 2000Jan 13, 2004The Procter & Gamble CompanyAnionic, amphoteric, and nonionic surfactants, and mixtures, dynamic viscosity in paste form is about 100,000 centipose; while using no or minimal eye irritation
US6838419Feb 26, 2004Jan 4, 2005Croda, Inc.Cosmetics; cleaning compounds
US6849584Nov 1, 2002Feb 1, 2005The Procter & Gamble CompanyComposition containing a cationic polymer and water insoluble solid material
US6897281Jun 19, 2002May 24, 2005Noveon Ip Holdings Corp.Breathable polyurethanes, blends, and articles
US6953773Jan 9, 2003Oct 11, 2005Croda, Inc.Mixtures of imidazoline quaternary ammonium and alkyl quaternary ammonium compounds
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US7026308Jun 22, 2000Apr 11, 2006The Procter & Gamble CompanyTopical anti-microbial compositions
US7045491Oct 21, 2004May 16, 2006Colgate-Palmolive Companyanionic soap, synthetic surfactant, a dibenzylidene- sorbitol, xylitol, or ribitol gelling agent, a glycerin humectant, and water; translucent, opalescent or opaque; good structural integrity and cleansing properties; pleasing aesthetics
US7091243Aug 9, 2002Aug 15, 2006Croda, Inc.Alkoxylated esters of dicarboxylic or tricarboxylic acids have an anti-irritating activity measured as a reduction in intracellular leakage of sodium fluorescein
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US7297668Apr 3, 2003Nov 20, 2007Colgate-Palmolive CompanyComposition
US7309496Jul 2, 2003Dec 18, 2007Colgate-Palmolive CompanyComposition
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US7485609Sep 29, 2005Feb 3, 2009Kimberly-Clark Worldwide, Inc.Personal cleansing article made of a capsule and a liquid cleansing composition contained within the capsule; capsule has a trigger such that upon occurrence of a specific event, the capsule releases the liquid; convenient to transport
US7524800Jun 12, 2008Apr 28, 2009Rhodia Inc.Mono-, di- and polyol phosphate esters in personal care formulations
US7524807Oct 31, 2003Apr 28, 2009The Procter & Gamble CompanyRinse-off personal care compositions comprising anionic and/or nonionic perfume polymeric particles
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US8211414Apr 18, 2005Jul 3, 2012Wsp Chemicals & Technology, LlcWater soluble polymer complexes with surfactants
US8226934Jun 26, 2008Jul 24, 2012Living Proof, Inc.controlling frizz in scalp hair by applying a mixture of a nonpolymeric fluorinated ester such as hexafluoroisopropyl 2-fluoroacrylate, water, emulsifiers and flow control agents
US8241618Aug 19, 2009Aug 14, 2012Lubrizol Advanced Materials, Inc.Process for producing a hydrophobically modified polymer for use with personal care compositions
US8268764Dec 8, 2009Sep 18, 2012The Procter & Gamble CompanyPorous, dissolvable solid substrate and surface resident starch perfume complexes
US8268765Nov 30, 2010Sep 18, 2012Rhodia OperationsMono-, di- and polyol phosphate esters in personal care formulations
US8273333Apr 16, 2009Sep 25, 2012The Procter & Gamble CompanyNon-lathering personal care composition in the form of an article
US8293699Jan 6, 2009Oct 23, 2012Rhodia OperationsHard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US8318138Jul 22, 2010Nov 27, 2012Living Proof, Inc.Hair care compositions and methods of treating hair using same
US8349300Apr 16, 2008Jan 8, 2013The Procter & Gamble CompanyPersonal care compositions containing at least two cationic polymers and an anionic surfactant
US8349301Sep 16, 2005Jan 8, 2013The Procter & Gamble CompanyMixture of surfactants, fatty amphiphiles and aqueous carrier
US8349302Jun 27, 2006Jan 8, 2013The Procter & Gamble CompanyShampoo containing a gel network and a non-guar galactomannan polymer derivative
US8349341Dec 8, 2010Jan 8, 2013The Procter & Gamble CompanyPorous, dissolvable solid substrate and a surface resident coating of cationic surfactant conditioner
US8349786Dec 8, 2009Jan 8, 2013The Procter & Gamble CompanyPorous, dissolvable solid substrates and surface resident cyclodextrin perfume complexes
US8349787Dec 8, 2010Jan 8, 2013The Procter & Gamble CompanyPorous, dissolvable solid substrate and a cationic surfactant conditioner material
US8361448Jun 27, 2006Jan 29, 2013The Procter & Gamble CompanyMixture of surfactants, crystalline fatty alcohol, and aqueous carrier; dispersed gel network
US8361449Mar 3, 2008Jan 29, 2013The Procter & Gamble CompanyShampoo containing a gel network
US8361450Nov 21, 2006Jan 29, 2013The Procter & Gamble CompanyShampoo containing a gel network and a non-guar galactomannan polymer derivative
US8361516Jul 31, 2007Jan 29, 2013SedermaComposition comprising sarsasapogenin
US8367048Nov 21, 2006Feb 5, 2013The Procter & Gamble CompanyShampoo containing a gel network
US8404648Feb 16, 2006Mar 26, 2013SedermaPolypeptides KXK and their use
US8414906Sep 22, 2009Apr 9, 2013Croda, Inc.Additives and products including oligoesters
US8415287Dec 8, 2009Apr 9, 2013The Procter & Gamble CompanyPorous, dissolvable solid substrate and surface resident inorganic particulate perfume complexes
US8425622May 23, 2012Apr 23, 2013The Procter & Gamble CompanySoluble solid hair coloring article
US8439981May 23, 2012May 14, 2013The Procter & Gamble CompanySoluble solid hair coloring article
US8440602Dec 20, 2010May 14, 2013The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition comprising a divinyl benzene cross-linked styrene polymer
US8440603Jun 19, 2012May 14, 2013The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition comprising a polylactic acid biodegradable abrasive
US8440604Sep 28, 2009May 14, 2013The Procter & Gamble CompanyLiquid hard surface cleaning composition
US8444716May 23, 2012May 21, 2013The Procter & Gamble CompanySoluble solid hair coloring article
US8445422Sep 20, 2011May 21, 2013The Procter & Gamble CompanyLiquid cleaning composition
US8450294Jan 8, 2009May 28, 2013Lubrizol Advanced Materials, Inc.Shampoo compositions
US8461090Dec 8, 2009Jun 11, 2013The Procter & Gamble CompanyPersonal care composition in the form of an article having a porous, dissolvable solid structure
US8461091Dec 8, 2009Jun 11, 2013The Procter & Gamble CompanyPersonal care composition in the form of an article having a porous, dissolvable solid structure
US8466099Dec 8, 2009Jun 18, 2013The Procter & Gamble CompanyProcess of making an article for dissolution upon use to deliver surfactants
US8470305Dec 7, 2007Jun 25, 2013The Procter & Gamble CompanyMixture of deteresive surfactant, solid, crystalline fatty acid gel network and aqueous carrier
US8470759Jun 19, 2012Jun 25, 2013The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition comprising a polyhydroxy-alkanoate biodegradable abrasive
US8476211Jul 30, 2012Jul 2, 2013The Procter & Gamble CompanyPorous, dissolvable solid substrates and surface resident starch perfume complexes
US8491877Mar 17, 2004Jul 23, 2013The Procter & Gamble Companycontaining a surfactant having an anionic group; treatment of microbial and fungal infections on the skin or scalp, especially dandruff; may also contain a pyrithione or polyvalent metal salt of pyrithione, particularly zinc pyrithione.
US8507649May 4, 2007Aug 13, 2013SedermaCosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
US8535651Jun 11, 2012Sep 17, 2013Wsp Chemicals & Technology, LlcWater soluble polymer complexes with surfactants
US8545818Jun 7, 2012Oct 1, 2013Living Proof, Inc.Hair care compositions and methods of treating hair using same
US8546316Sep 20, 2011Oct 1, 2013The Procter & Gamble CompanyLiquid detergent composition with natural abrasive particles
US8546317Jul 9, 2010Oct 1, 2013The Procter & Gamble CompanyHard surface cleaning composition
US8551463Jun 9, 2010Oct 8, 2013Living Proof, Inc.Hair care compositions and methods of treating hair
US8551932Sep 28, 2009Oct 8, 2013The Procter & Gamble CompanyLiquid hard surface cleaning composition
US8557223Jul 22, 2010Oct 15, 2013Living Proof, Inc.Hair care compositions and methods of treating hair using same
US8563496Dec 10, 2010Oct 22, 2013The Procter & Gamble CompanyLiquid acidic hard surface cleaning composition
US8568702Apr 26, 2011Oct 29, 2013The Procter & Gamble CompanyUse and application of defined zwitterionic copolymer
US8569223Sep 28, 2009Oct 29, 2013The Procter & Gamble CompanyLiquid hard surface cleaning composition
US8628706Aug 29, 2012Jan 14, 2014The Procter & Gamble CompanyNon-lathering personal care composition in the form of an article
US8629095Apr 20, 2011Jan 14, 2014The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition comprising polyurethane foam abrasive particles
US8653014Oct 5, 2012Feb 18, 2014The Procter & Gamble CompanyShampoo composition containing a gel network
US8658145Aug 3, 2009Feb 25, 2014The Lubrizol CorporationLow molecular weight ampholytic polymers for personal care applications
US8673274Dec 12, 2007Mar 18, 2014The Procter & Gamble CompanyComposition comprising pyrithione or a polyvalent metal salt of a pyrithione and furametpyr
US8680036Dec 20, 2010Mar 25, 2014The Procter & Gamble CompanyLiquid cleaning composition comprising color-stable polyurethane abrasive particles
US8697656Jan 15, 2010Apr 15, 2014SedermaCompounds, in particular peptides, compositions comprising them and cosmetic and dermo-pharmaceutical uses
US8703685Jun 19, 2012Apr 22, 2014The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition comprising polylactic acid abrasives
US8741357Jan 13, 2006Jun 3, 2014Sederma SasCosmetic or dermopharmaceutical composition comprising an euglena extract
US8759270Jun 14, 2012Jun 24, 2014The Procter & Gamble CompanyLiquid detergent composition with abrasive particles
US8765170Jan 29, 2009Jul 1, 2014The Procter & Gamble CompanyPersonal care composition in the form of an article
US8795695Aug 15, 2012Aug 5, 2014The Procter & Gamble CompanyPersonal care methods
US8796252Dec 23, 2004Aug 5, 2014Arch Chemicals, Inc.Pyrithione biocides enhanced by zinc metal ions and organic amines
US8808678Sep 25, 2013Aug 19, 2014The Procter & Gamble CompanyUse and application of defined zwitterionic copolymer
US8829118Oct 8, 2009Sep 9, 2014Nalco CompanyMethod for using hydrophobically modified polymers in consumer and industrial applications
US8840871Jul 28, 2009Sep 23, 2014The Procter & Gamble CompanyMultiphase personal care composition with enhanced deposition
EP1845152A1Apr 14, 2006Oct 17, 2007The Procter and Gamble CompanyProcess of cleaning a hard surface with zwitterionic copolymer
EP1938791A2Dec 21, 2007Jul 2, 2008L'OréalCosmetic composition for keratinous substrates containing triarylmethane compounds
EP2025742A1Apr 29, 2008Feb 18, 2009The Procter and Gamble CompanyLiquid acidic hard surface cleaning composition
EP2039749A1Sep 10, 2008Mar 25, 2009The Procter & Gamble CompanyProcess of treating inclined hard surface
EP2075324A1Dec 27, 2007Jul 1, 2009The Procter and Gamble CompanyLiquid acidic hard surface cleaning composition
EP2075325A1Nov 13, 2008Jul 1, 2009The Procter & Gamble CompanyLiquid acidic hard surface cleaning composition
EP2082723A1Jun 23, 2000Jul 29, 2009The Procter and Gamble CompanyTopical anti-microbial compositions
EP2105123A2Mar 19, 2002Sep 30, 2009The Procter & Gamble CompanySkin care compositions containing a sugar amine and a vitamin B3 compound
EP2112218A1Apr 25, 2008Oct 28, 2009The Procter and Gamble CompanyColored bleaching composition
EP2206766A1Dec 23, 2008Jul 14, 2010The Procter and Gamble CompanyLiquid acidic hard surface cleaning composition
EP2230226A1 *Dec 3, 2009Sep 22, 2010Infineum International LimitedAdditives for fuel oils
EP2272942A1Jul 8, 2009Jan 12, 2011The Procter and Gamble CompanyHard surface cleaning composition
EP2287214A1Nov 17, 2006Feb 23, 2011The Procter and Gamble CompanyUse and application of defined zwitterionic copolymer
EP2295531A1Sep 14, 2009Mar 16, 2011The Procter & Gamble CompanyA fluid laundry detergent composition
EP2319909A1Sep 28, 2010May 11, 2011Johnson & Johnson Consumer Companies, Inc.Soap bar containing hydrogel phase particles
EP2336282A1Dec 17, 2009Jun 22, 2011The Procter and Gamble CompanyLiquid acidic hard surface cleaning composition
EP2338962A1Dec 20, 2010Jun 29, 2011The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2338963A1Dec 20, 2010Jun 29, 2011The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2338964A2Dec 20, 2010Jun 29, 2011The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2338965A1Dec 20, 2010Jun 29, 2011The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2338966A1Dec 20, 2010Jun 29, 2011The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2365051A1Mar 11, 2011Sep 14, 2011The Procter and Gamble CompanyFluid detergent compositions comprising a di-amido gellant, and process for making
EP2365053A1Mar 11, 2011Sep 14, 2011The Procter and Gamble CompanyLiquid detergent compositions comprising pH tuneable amido-gellants, and processes for making
EP2371349A1Feb 10, 2004Oct 5, 2011Colgate-Palmolive CompanyMethod of detection of ashen skin
EP2399978A1Jun 24, 2010Dec 28, 2011The Procter and Gamble CompanyStable non-aqueous liquid compositions comprising a cationic polymer in particulate form
EP2399979A1Jun 24, 2010Dec 28, 2011The Procter and Gamble CompanySoluble unit dose articles comprising a cationic polymer
EP2399980A1Jun 24, 2010Dec 28, 2011The Procter and Gamble CompanyStable compositions comprising cationic cellulose polymer and cellulase
EP2431452A1Sep 20, 2011Mar 21, 2012The Procter and Gamble CompanyLiquid cleaning composition
EP2431453A1Sep 20, 2011Mar 21, 2012The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2431454A1Sep 20, 2011Mar 21, 2012The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2431455A1Sep 20, 2011Mar 21, 2012The Procter and Gamble CompanyLiquid cleaning and/or cleansing composition
EP2510982A1May 4, 2007Oct 17, 2012SedermaCosmetic compositions comprising at least one peptide with at least one immobilized aromatic cycle
EP2573156A1Sep 20, 2011Mar 27, 2013The Procter and Gamble CompanyLiquid cleaning composition
EP2586855A1Dec 23, 2008May 1, 2013The Procter and Gamble CompanyLiquid acidic hard surface cleaning composition
EP2612647A1Mar 21, 2008Jul 10, 2013Colgate-Palmolive CompanyStructured compositions comprising a clay
EP2631286A1Feb 23, 2012Aug 28, 2013The Procter and Gamble CompanyLiquid cleaning composition
EP2666457A2Apr 16, 2009Nov 27, 2013The Procter and Gamble CompanyProcess for forming a non-lathering personal care article in the form of a dissolvable solid foam
EP2666458A2Apr 16, 2009Nov 27, 2013The Procter and Gamble CompanyPre-mix for a non-lathering personal care article, the article having the form of a solid foam
EP2687287A2May 12, 2010Jan 22, 2014The Procter and Gamble CompanyDelivery particles
EP2687590A2May 12, 2010Jan 22, 2014The Procter and Gamble CompanyDelivery particles
EP2746379A1Dec 20, 2012Jun 25, 2014The Procter and Gamble CompanyProcess for the production of a liquid composition
WO2002030237A2Oct 9, 2001Apr 18, 2002Procter & GambleArticle for the delivery of foam products
WO2006044296A1Oct 11, 2005Apr 27, 2006Colgate Palmolive CoConditioning shampoos with detergent soluble silicones
WO2007109152A2 *Mar 16, 2007Sep 27, 2007Croda IncAmine/amide-functionalized lipophiles
WO2007119226A2Apr 18, 2007Oct 25, 2007Procter & GambleRheology modifying systems and detersive compositions
WO2008046258A1Dec 15, 2006Apr 24, 2008Zongren FangCosmetic composition and preparation method and use thereof
WO2008116147A2Mar 21, 2008Sep 25, 2008Colgate Palmolive CoStructured compositions comprising a clay
WO2010067327A1Dec 10, 2009Jun 17, 2010SedermaCosmetic composition containing acetylated oligoglucuronans
WO2010075120A1Dec 16, 2009Jul 1, 2010The Procter & Gamble CompanyLiquid acidic hard surface cleaning composition
WO2010077650A2Dec 8, 2009Jul 8, 2010The Procter & Gamble CompanyPersonal care composition in the form of an article having a porous, dissolvable solid structure
WO2010077653A2Dec 8, 2009Jul 8, 2010The Procter & Gamble CompanyPersonal care composition in the form of an article having a hydrophobic surface-resident coating
WO2010082175A2Jan 15, 2010Jul 22, 2010SedermaNew compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
WO2010082176A2Jan 15, 2010Jul 22, 2010SedermaCosmetic composition containing kxk type peptides and uses
WO2010082177A2Jan 15, 2010Jul 22, 2010SedermaNew compounds, in particular peptides, compositions comprising them and cosmetic and dermopharmaceutical uses
WO2010088350A2Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyPersonal care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials
WO2010088351A1Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyPersonal care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials
WO2010088352A1Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyPersonal care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials
WO2010088353A1Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyPersonal care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials
WO2010088354A1Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyMagnetic resonance imaging of a personal-care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials
WO2010088430A2Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyMethods for improving skin quality using rinse-off personal care compositions with variable amounts of hydrophobic benefit agents
WO2010088432A2Jan 28, 2010Aug 5, 2010The Procter & Gamble CompanyMethods for improving skin quality using rinse-off personal care compositions with variable amounts of hydrophobic benefit agents
WO2010136965A2May 25, 2010Dec 2, 2010SedermaCosmetic use of tyr-arg dipeptide to combat cutaneous sa
WO2010141683A2Jun 3, 2010Dec 9, 2010The Procter & Gamble CompanyMultiple product system for hair
WO2010144397A1Jun 8, 2010Dec 16, 2010The Procter & Gamble CompanyProcess for making a cleaning composition employing direct incorporation of concentrated surfactants
WO2011014401A2Jul 22, 2010Feb 3, 2011The Procter & Gamble CompanyOral care articles and methods
WO2011019883A2Aug 12, 2010Feb 17, 2011The Procter & Gamble CompanyRinse-off care products and consumer product line-ups comprising same
WO2011031712A2Sep 8, 2010Mar 17, 2011The Procter & Gamble CompanyA fluid laundry detergent composition
WO2011042409A2Oct 5, 2010Apr 14, 2011Momentive Performance Materials GmbhAqueous emulsions of polyorganosiloxanes
WO2011075466A1Dec 14, 2010Jun 23, 2011The Procter & Gamble CompanyLiquid acidic hard surface cleaning composition
WO2011076314A1Nov 11, 2010Jun 30, 2011Merck Patent GmbhElectroluminescent formulations
WO2011076323A1Nov 24, 2010Jun 30, 2011Merck Patent GmbhFormulations comprising phase-separated functional materials
WO2011079160A2Dec 22, 2010Jun 30, 2011Colgate-Palmolive CompanyVisually patterned and oriented compositions
WO2011084577A1Dec 16, 2010Jul 14, 2011The Procter & Gamble CompanyHard surface cleaning composition having a malodor control component and methods of cleaning hard surfaces
WO2011087733A1Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011087735A1Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011087736A1Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011087739A1Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011087744A2Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011087748A1Dec 20, 2010Jul 21, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011088338A2Jan 14, 2011Jul 21, 2011The Procter & Gamble CompanyMethods for improving skin quality
WO2011109319A1Mar 1, 2011Sep 9, 2011The Procter & Gamble CompanyDual-usage liquid laundry detergents
WO2011112886A1Mar 11, 2011Sep 15, 2011The Procter & Gamble CompanyFluid detergent compositions comprising a di-amido gellant, and processes for making
WO2011112910A1Mar 11, 2011Sep 15, 2011The Procter & Gamble CompanyLiquid detergent compositions comprising ph tuneable amido-gellants, and processes for making
WO2011116775A2Mar 25, 2011Sep 29, 2011Liquid Vanity ApsLaundry detergent
WO2011123727A2Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyOrganosilicones
WO2011123732A1Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyComposition comprising modified organosilicones
WO2011123734A1Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyCare polymers
WO2011123736A1Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyCare polymers
WO2011123739A1Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyCompositions comprising organosilicones
WO2011127102A1Apr 6, 2011Oct 13, 2011The Procter & Gamble CompanyOptimized release of bleaching systems in laundry detergents
WO2011133438A1Apr 18, 2011Oct 27, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011133508A1Apr 19, 2011Oct 27, 2011The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2011156551A1Jun 9, 2011Dec 15, 2011The Procter & Gamble CompanyMethod for preparing a non-ionic surfactant stable personal care dispersion
WO2011156558A1Jun 9, 2011Dec 15, 2011The Procter & Gamble CompanyCocoamide monoethanolamine (cmea) composition
WO2011156584A1Jun 9, 2011Dec 15, 2011The Procter & Gamble CompanyMethods of preparing personal care compositions
WO2011156672A2Jun 10, 2011Dec 15, 2011The Procter & Gamble CompanyCompositions for treating skin
WO2011163112A1Jun 20, 2011Dec 29, 2011The Procter & Gamble CompanyStable compositions comprising cationic cellulose polymers and cellulase
WO2011163371A1Jun 22, 2011Dec 29, 2011The Procter & Gamble CompanyStable non-aqueous liquid compositions comprising a cationic polymer in particulate form
WO2011163428A1Jun 23, 2011Dec 29, 2011The Procter & Gamble CompanySoluble unit dose articles comprising a cationic polymer
WO2012021436A2Aug 8, 2011Feb 16, 2012Croda, Inc."green" diester amines and personal care products
WO2012040136A1Sep 20, 2011Mar 29, 2012The Procter & Gamble CompanyLiquid cleaning composition
WO2012040141A1Sep 20, 2011Mar 29, 2012The Procter & Gamble CompanyLiquid cleaning composition
WO2012040142A1Sep 20, 2011Mar 29, 2012The Procter & Gamble CompanyLiquid cleaning composition
WO2012040143A1Sep 20, 2011Mar 29, 2012The Procter & Gamble CompanyLiquid cleaning composition
WO2012058557A2Oct 28, 2011May 3, 2012The Procter & Gamble CompanyPersonal care compositions comprising a pyrithione and an iron chelator
WO2012138685A1Apr 4, 2012Oct 11, 2012The Procter & Gamble CompanyPersonal care article
WO2012138696A2Apr 4, 2012Oct 11, 2012The Procter & Gamble CompanyShampoo compositions with increased deposition of polyacrylate microcapsules
WO2012138710A2Apr 4, 2012Oct 11, 2012The Procter & Gamble CompanyPersonal cleansing compositions with increased deposition of polyacrylate microcapsules
WO2012138716A2Apr 4, 2012Oct 11, 2012The Procter & Gamble CompanyDissolvable, personal cleansing compositions
WO2012138820A1Apr 5, 2012Oct 11, 2012The Procter & Gamble CompanyContinuous process of making an article of dissolution upon use to deliver surfactants
WO2012162331A2May 23, 2012Nov 29, 2012The Procter & Gamble CompanyCompositions comprising an efficient perfume bloom
WO2012166477A2May 23, 2012Dec 6, 2012The Procter & Gamble CompanySoluble solid hair coloring article
WO2012166478A2May 23, 2012Dec 6, 2012The Procter & Gamble CompanySoluble solid hair coloring article
WO2012170784A2Jun 8, 2012Dec 13, 2012The Procter & Gamble CompanyPersonal care compositions
WO2012174091A2Jun 13, 2012Dec 20, 2012The Procter & Gamble CompanyPERSONAL CARE COMPOSITIONS COMPRISING A pH TUNEABLE GELLANT AND METHODS OF USING
WO2012174096A2Jun 13, 2012Dec 20, 2012The Procter & Gamble CompanyPersonal care compositions comprising a di-amido gellant and methods of using
WO2012177615A1Jun 19, 2012Dec 27, 2012The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2012177617A1Jun 19, 2012Dec 27, 2012The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2012177628A1Jun 19, 2012Dec 27, 2012The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2012177676A1Jun 20, 2012Dec 27, 2012The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2012177757A2Jun 20, 2012Dec 27, 2012The Procter & Gamble CompanyPersonal care compositions comprising shaped abrasive particles
WO2012177886A2Jun 21, 2012Dec 27, 2012The Procter & Gamble CompanyProcess of forming crystals for use in a personal care composition
WO2013025743A2Aug 15, 2012Feb 21, 2013The Procter & Gamble CompanyPersonal care compositions having dried zinc pyrithione
WO2013025744A2Aug 15, 2012Feb 21, 2013The Procter & Gamble CompanyPersonal care methods
WO2013025745A2Aug 15, 2012Feb 21, 2013The Procter & Gamble CompanyPersonal care compositions having dried zinc pyrithione-polymer aggregates
WO2013025765A2Aug 15, 2012Feb 21, 2013The Procter & Gamble CompanyMethods of reducing odor
WO2013025769A2Aug 15, 2012Feb 21, 2013The Procter & Gamble CompanyMethods of enhancing skin hydration and improving non-diseased skin
WO2013025893A1Aug 16, 2012Feb 21, 2013The Gillette CompanyPersonal care compositions comprising an anti-irritation agent
WO2013039963A1Sep 12, 2012Mar 21, 2013The Procter & Gamble CompanyMicrocapsule compositions comprising ph tuneable di-amido gellants
WO2013043622A1Sep 19, 2012Mar 28, 2013The Procter & Gamble CompanyLiquid cleaning composition
WO2013043803A2Sep 20, 2012Mar 28, 2013The Procter & Gamble CompanyDetergent compositions comprising specific blend ratios of isoprenoid-based surfactants
WO2013043805A1Sep 20, 2012Mar 28, 2013The Procter & Gamble CompanyDetergent compositions comprising primary surfactant systems comprising highly branched surfactants especially isoprenoid - based surfactants
WO2013043852A2Sep 20, 2012Mar 28, 2013The Procter & Gamble CompanyEasy-rinse detergent compositions comprising isoprenoid-based surfactants
WO2013043855A2Sep 20, 2012Mar 28, 2013The Procter & Gamble CompanyHigh suds detergent compositions comprising isoprenoid-based surfactants
WO2013043857A1Sep 20, 2012Mar 28, 2013The Procter & Gamble CompanyDetergent compositions comprising sustainable surfactant systems comprising isoprenoid-derived surfactants
WO2013052802A2Oct 5, 2012Apr 11, 2013The Procter & Gamble CompanyShampoo composition containing a gel network
WO2013086178A2Dec 6, 2012Jun 13, 2013The Procter & Gamble CompanyPersonal care compositions
WO2013106367A2Jan 9, 2013Jul 18, 2013The Procter & Gamble CompanyHair care compositions
WO2013126535A1Feb 21, 2013Aug 29, 2013The Procter & Gamble CompanyLiquid cleaning composition with abrasive powder from olive kernels
WO2013142654A2Mar 21, 2013Sep 26, 2013The Procter & Gamble CompanyCompositions for delivering perfume to the skin
WO2013142672A2Mar 21, 2013Sep 26, 2013The Procter & Gamble CompanyPersonal care compositions and methods
WO2013158380A2Apr 5, 2013Oct 24, 2013The Procter & Gamble CompanyHair care composition comprising metathesized unsaturated polyol esters
WO2013158851A2Apr 18, 2013Oct 24, 2013The Procter & Gamble CompanyImproving skin appearance with increase in skin chroma
WO2013158877A1Apr 18, 2013Oct 24, 2013The Procter & Gamble CompanyPersonal cleansing compositions
WO2013158878A1Apr 18, 2013Oct 24, 2013The Procter & Gamble CompanyMethods relating to personal care compositions
WO2013176666A1May 23, 2012Nov 28, 2013The Procter & Gamble CompanySoluble solid hair coloring article
WO2013187917A1Jun 19, 2012Dec 19, 2013The Procter & Gamble CompanyLiquid cleaning and/or cleansing composition
WO2014059252A2Oct 11, 2013Apr 17, 2014The Procter & Gamble CompanyPersonal care composition in the form of a dissolvable article
WO2014070834A1Oct 30, 2013May 8, 2014The Procter & Gamble CompanyPersonal care compositions comprising self-assembling peptides
WO2014093819A2Dec 13, 2013Jun 19, 2014The Procter & Gamble CompanyAntiperspirant and deodorant compositions
WO2014093828A2Dec 13, 2013Jun 19, 2014The Procter & Gamble CompanyAntiperspirant and deodorant compositions
Classifications
U.S. Classification560/170, 560/171
International ClassificationC08L77/00
Cooperative ClassificationC08L77/00
European ClassificationC08L77/00