Source: http://www.google.com/patents/US5721202?dq=7800613
Timestamp: 2014-07-13 16:24:57
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Matched Legal Cases: ['application No. 08', 'application No. 08', 'application No. 08', 'application No. 08', 'application No. 08', 'application No. 08', 'application No. 08']

Patent US5721202 - Perfumes for laundry and cleaning composition - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign in<nobr>Advanced Patent Search</nobr>PatentsEsters of perfume alcohols having at least one free carboxylate group are provided. The esters have the general formula: ##STR1## wherein R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group; R' is...http://www.google.com/patents/US5721202?utm_source=gb-gplus-sharePatent US5721202 - Perfumes for laundry and cleaning compositionAdvanced Patent SearchPublication numberUS5721202 APublication typeGrantApplication numberUS 08/552,909Publication dateFeb 24, 1998Filing dateNov 3, 1995Priority dateNov 3, 1995Fee statusPaidAlso published asCA2236658A1, DE69623820D1, EP0876467A1, EP0876467B1, WO1997016523A1Publication number08552909, 552909, US 5721202 A, US 5721202A, US-A-5721202, US5721202 A, US5721202AInventorsScott William Waite, John Cort Severns, Mark Robert Sivik, Frederick Anthony HartmanOriginal AssigneeThe Procter & Gamble CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (24), Non-Patent Citations (40), Referenced by (26), Classifications (13), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetPerfumes for laundry and cleaning compositionUS 5721202 AAbstract Esters of perfume alcohols having at least one free carboxylate group are provided. The esters have the general formula: ##STR1## wherein R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group; R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300� C.; and m and n are independently an integer of 1 or greater. The esters are employed as perfume components in laundry and cleaning compositions such as fabric softening compositions.
What is claimed is: 1. Laundry and cleaning compositions comprising:(a) a perfume component having at least about 2% by weight of an ester of a perfume alcohol wherein the ester has at least one free carboxylate group, said ester having the formula: ##STR14## wherein R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, aryl group; or ring containing a heteroatom, R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300� C.; and m and n are independently an integer of 1 or greater; and (b) ingredients useful for formulating laundry and cleaning compositions selected from the group consisting of cationic or nonionic fabric softening agents, enzymes, enzyme stabilizers, detersive surfactants, builders, bleaching compounds, polymeric soil release agents, dye transfer inhibiting agents, polymeric dispersing agents, suds suppressors, optical brighteners, chelating agents, fabric softening clays, anti-static agents, and mixtures thereof. 2. The laundry and cleaning compositions as claimed in claim 1, wherein said perfume component comprises from about 0.01% to about 10% by weight of said composition.
FIELD OF THE INVENTION The present invention relates to laundry and cleaning products comprising esters of alcohol perfumes.
BACKGROUND OF THE INVENTION Consumer acceptance of cleaning and laundry products is determined not only by the performance achieved with these products but the aesthetics associated therewith. The perfume systems are therefore an important aspect of the successful formulation of such commercial products.
BACKGROUND ART Mechanistic studies are described in Schmid, Tetrahedron Letters, 33, p. 757 (1992); and Cori et al., J. Org. Chem., 51, p. 1310 (1986). Carey et al., Advanced Organic Chemistry, Part A, 2nd Ed., pp. 421-426 (Plenum, New York; 1984) describes ester chemistry more generally.
SUMMARY OF THE INVENTION The present invention relates to laundry and cleaning compositions having a perfume component. The perfume component includes at least about 2% by weight of an ester of a perfume alcohol wherein the ester has at least one free carboxylate group. The esters of the present invention provide a superior consumer noticeable benefit to fabrics laundered in the compositions of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The compositions of the present invention include a perfume component which comprises at least about 2% by weight and more preferably at least about 5% by weight of an ester of a perfume alcohol wherein the ester has at least one free carboxylate group. The esters of the present invention have the general formula: ##STR3## wherein R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group; R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300� C.; and m and n are independently an integer of 1 or greater. Preferably, R is selected from the group consisting of substituted or unsubstituted C1 -C20 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, aryl group or ring containing a heteroatom. Most preferably, the esters are maleate, succinate, pyromellitate, trimellitate citrate, phthalate or adipate esters of the alcohol perfume. As can be seen, formula (I) includes at least one free carboxylate group.
EXAMPLE I Mono-geranyl succinate
EXAMPLE II Mono-(cis-3-hexenyl)maleate cis-3-Hexenol in the amount of 30.00 g (0.299 mol) and maleic anhydride powder in the amount of 24.46 g (0.249 mol) were combined in a 250 mL three-necked round-bottomed flask fitted with a condenser, argon inlet, mechanical stirrer and internal thermometer. The mixture was heated to 100�-105� C. for 2 hours during which time the mixture became homogeneous. The product mixture was cooled to room temperature, filtered, and concentrated by Kugelrohr distillation at 40 � C. (0.3 mm Hg) for 4 hours. Mono-(cis-3-hexenyl)maleate was isolated as a colorless oil. Purity of the product was determined by thin layer and gas chromatography and the structure confirmed by 1 H and 13 C NMR.
EXAMPLE III Mono-phenoxanyl maleate
EXAMPLE IV Mono-phenoxanyl fumarate
EXAMPLE V cis- and trans-Di-(β-citronellyl)pyromellitate
EXAMPLE VI Mono-(β-citronellyl)succinate
EXAMPLE VII Mono-phenoxyethyl succinate
EXAMPLE VIII Mono-(β-citronellyl)phthalate
EXAMPLE IX Liquid fabric softener compositions according to the present invention are formulated as follows:
EXAMPLE X Additional liquid fabric conditioner formulas include the following.
EXAMPLE XI A fabric conditioner bar is prepared having the following components.
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Toxicol., 1974, 12, p. 891.2"Geranyl phenylacetate", Food Cosmet. Toxicol., 1974, 12, p. 895.3 *Carey et al., Advanced Organic Chemistry, Part A, 2nd Ed.,pp. 421 426 (Penum, NY; 1984).4Carey et al., Advanced Organic Chemistry, Part A, 2nd Ed.,pp. 421-426 (Penum, NY; 1984).5Chemical Abstracts Service, Abstract #115(4): 141973x (1991).6Chemical Abstracts Service, Abstract #117(26): 253848k (1992).7Chemical Abstracts Service, Abstract #66(7): 28371h (1967).8Chemical Abstracts Service, Abstract #71:24728, Weitzel (1989).9 *Chemical Abstracts Service, Abstract 115(4): 141973x (1991).10 *Chemical Abstracts Service, Abstract 117(26): 253848k (1992).11 *Chemical Abstracts Service, Abstract 66(7): 28371h (1967).12 *Chemical Abstracts Service, Abstract 71:24728, Weitzel (1989).13Cori, Osvaldo, "Rearrangement of Linalool, Geraniol, and Nerol and Their Derivatives", J. Org. Chem. (1986) vol. 51, pp. 1310-1316.14 *Cori, Osvaldo, Rearrangement of Linalool, Geraniol, and Nerol and Their Derivatives , J. Org. Chem. (1986) vol. 51, pp. 1310 1316.15 *Derwent Abstract, JP 2034696, Feb. 5, 1990 (Kao Corporation).16 *Derwent Abstract, JP 2166195, Jun. 26, 1990 (Lion Corporation).17 *Derwent Abstract, JP 3181599, Aug. 7, 1991 (Lion Corporation).18 *Derwent Abstract, JP 48043329 (Toray Ind.).19 *Derwent Abstract, JP 59001410, Jan. 6, 1984 (Toray Ind.).20 *Derwent Abstract, JP 60023498, Feb.6, 1985 (Lion Corporation).21 *Derwent Abstract, JP 63035696, Feb. 16, 1988 (Lion Corporation).22 *Derwent Abstract, JP 6400179, Jan. 6, 1989 (Kao Corporation).23Erdmann, Ernst, "Ueber einige Ester und einen krystallisirten Pseudoester des Rhodinols", Chem. Ber., 31, (1898), pp. 356-360.24 *Erdmann, Ernst, Ueber einige Ester und einen krystallisirten Pseudoester des Rhodinols , Chem. Ber., 31, (1898), pp. 356 360.25 *Geranyl crotonate , Food Cosmet. Toxicol., 1974, 12, p. 891.26 *Geranyl phenylacetate , Food Cosmet. Toxicol., 1974, 12, p. 895.27Mohacsi, Erno, "Regioselective Epoxidation of Geranyl Palmitate with Metacholoroperbenzoic Acid", Synthetic Communications, 21(21), (1991), pp. 2257-2261.28 *Mohacsi, Erno, Regioselective Epoxidation of Geranyl Palmitate with Metacholoroperbenzoic Acid , Synthetic Communications, 21(21), (1991), pp. 2257 2261.29 *Mukaiyama et al., Chem. Letters, pp. 563 566 (1980).30Mukaiyama et al., Chem. Letters, pp. 563-566 (1980).31 *Patent Abstracts of Japan, JP 59001446, Jan. 6, 1984 (Toray).32 *Schmid, Tetrahedron Letters, 33, pp. 757 760 (1992).33Schmid, Tetrahedron Letters, 33, pp. 757-760 (1992).34 *U.S. application No. 08/277,558, Hartman et al., filed Jun. 19, 1994.35 *U.S. application No. 08/482,668, Sivik, filed Jul. 7, 1995.36 *U.S. application No. 08/499,158, Severns et al., filed Aug. 7, 1995.37 *U.S. application No. 08/499,282, Severns et al., filed Jul. 7, 1995.38 *U.S. application No. 08/517,941, Hartman et al., filed Aug. 22, 1995.39 *U.S. application No. 08/522,764, Waite et al., Nov. 3, 1995.40 *U.S. application No. 08/601,881, Hartman et al., filed Feb. 15, 1996.* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS5922083 *Mar 12, 1996Jul 13, 1999Procter & Gamble CompanyFabric pretreating composition comprising hydrogen peroxide source, bleach activator, builder, anionic surfactant, proteolytic enzyme, oxidative stability enhanced amylase enzymeUS6020302 *Sep 18, 1997Feb 1, 2000The Procter & Gamble CompanyColor care compositionsUS6083892 *Aug 19, 1997Jul 4, 2000The Procter & Gamble CompanyAutomatic dishwashing detergents comprising β-ketoester pro-fragrancesUS6136769 *Apr 21, 1999Oct 24, 2000The Procter & Gamble CompanyAlkoxylated cationic detergency ingredientsUS6147045 *Jul 18, 1996Nov 14, 2000The Procter & Gamble Co.Mixture of nonionic and anionic surfactantsUS6187727 *Jul 12, 1999Feb 13, 2001Bush Boake Allen, Inc.Use of 2-methyl-3-cyclohexylpropanol, esters thereof or mixtures thereofUS6228821Oct 25, 1999May 8, 2001Amway CorporationCleaning composition comprising ingredients useful for formulating laundry and cleaning compositions, enzymes, perfume, stabilizer selected from group consisting of thiosulfate, thiosulfuric acid and mixtures thereofUS6303563 *Feb 10, 1999Oct 16, 2001The Procter & Gamble CompanyFor cleaning and softening in domestic laundry processesUS6610646May 30, 2001Aug 26, 2003The Procter & Gamble CompanyA) a pro-fragrance component; and b) a free fragrance component; enhanced longevity of the initial fragrance accords.US6939835 *Jan 30, 2003Sep 6, 2005Firmenich SaCyclic compounds and their use as precursors of fragrant alcoholsUS6984618 *Dec 5, 2002Jan 10, 2006The Procter & Gamble CompanyMixture of quaternary ammonium compound and clayUS7648953May 8, 2008Jan 19, 2010The Dial CorporationEco-friendly laundry detergent compositions comprising natural essenceUS7709436Jul 24, 2008May 4, 2010The Dial CorporationLow carbon footprint compositions for use in laundry applicationsEP1760142A1Aug 31, 2006Mar 7, 2007The Procter and Gamble CompanyLaundry Scent CustomizationEP1992680A2Sep 6, 2002Nov 19, 2008The Procter and Gamble CompanyScented candlesEP2322593A1Nov 12, 2009May 18, 2011The Procter and Gamble CompanyLiquid laundry detergent compositionEP2322595A1Nov 12, 2009May 18, 2011The Procter and Gamble CompanySolid laundry detergent compositionWO1998038269A1 *Feb 20, 1998Sep 3, 1998Procter & GambleLaundry detergent bars with improved physical propertiesWO2001091712A2Jun 1, 2001Dec 6, 2001Procter & GambleEnhanced duration fragrance delivery systems having a non-distorted initial fragrance impressionWO2006010087A1Jul 8, 2005Jan 26, 2006Procter & GambleRoller for providing benefits to fabricWO2011002872A1Jun 30, 2010Jan 6, 2011The Procter & Gamble CompanyMultiple use fabric conditioning composition with aminosiliconeWO2011059714A1Oct 28, 2010May 19, 2011The Procter & Gamble CompanySolid laundry detergent compositionWO2011060028A1Nov 10, 2010May 19, 2011The Procter & Gamble CompanyLiquid laundry detergent compositionWO2011123737A1Apr 1, 2011Oct 6, 2011The Procter & Gamble CompanyCare polymersWO2011143321A1May 11, 2011Nov 17, 2011The Procter & Gamble CompanyCare polymersWO2011143322A1May 11, 2011Nov 17, 2011The Procter & Gamble CompanyFabric and home care product comprising care polymers* Cited by examinerClassifications U.S. Classification510/102, 510/276, 510/515, 510/107, 510/519International ClassificationC11D3/00, C11D3/50, C11B9/00, C11D3/20Cooperative ClassificationC11D3/507, C11D3/0015European ClassificationC11D3/00B3L, C11D3/50B4Legal EventsDateCodeEventDescriptionJun 22, 2009FPAYFee paymentYear of fee payment: 12Jun 30, 2005FPAYFee paymentYear of fee payment: 8Jul 30, 2001FPAYFee paymentYear of fee payment: 4Apr 8, 1996ASAssignmentOwner name: PROCTER & GAMBLE COMPANY, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WAITE, SCOTT WILLIAM;SEVERNS, JOHN CORT;SIVIK, MARK ROBERT;AND OTHERS;REEL/FRAME:007891/0126Effective date: 19951115RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services©2012 Google