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WO2001023512A1 - Utilisation dans une composition de detergent d'un copolyester sulfo-fonctionnel comme element permettant de retenir le parfum - Google Patents

Utilisation dans une composition de detergent d'un copolyester sulfo-fonctionnel comme element permettant de retenir le parfum Download PDF

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Publication number
WO2001023512A1
WO2001023512A1 PCT/EP2000/009340 EP0009340W WO0123512A1 WO 2001023512 A1 WO2001023512 A1 WO 2001023512A1 EP 0009340 W EP0009340 W EP 0009340W WO 0123512 A1 WO0123512 A1 WO 0123512A1
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WIPO (PCT)
Prior art keywords
sulfo
functional
formula
radicals
fragrance
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Ceased
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PCT/EP2000/009340
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English (en)
Inventor
Gladys Saliba Gabriel
Jeanne Chang
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Rhodia Chimie SAS
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Rhodia Chimie SAS
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Application filed by Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Priority to AU76591/00A priority Critical patent/AU7659100A/en
Publication of WO2001023512A1 publication Critical patent/WO2001023512A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3715—Polyesters or polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention relates to the use, in a detergent composition comprising a fragrance and intended for the treatment of surfaces, of a water- soluble or water-dispersible sulfo-functional copolyester of low molecular mass as a retainer for the fragrances on said treated surfaces, especially as a fragrance retainer on laundry or textiles after they have been washed using said detergent composition.
  • water-soluble or water- dispersible sulfo-functional copolyesters of low molecular mass especially sulfo-functional copolyesters having a numerical molecular mass of less than 20,000 and obtained from at least one nonsulfo- functional diacid monomer, at least one sulfo- functional diacid monomer and at least one polyol, especially those obtained from a diester of terephthalic acid, isophthalic acid, a diester of sulfoisophthalic acid and a diol as soil release agents in detergent compositions for laundry or textiles, based in particular on polyester (WO 95/32997).
  • the applicant has now found that the presence of a water-soluble or water-dispersible sulfo- functional copolyester of low molecular mass in a detergent composition comprising a fragrance and intended for the treatment of surfaces made it possible to increase the fragrance retention on said treated surfaces, especially on laundry or textiles after washing it or them using said composition.
  • the invention first provides for the use, in a detergent composition comprising a fragrance and intended for the treatment of surfaces, especially for washing laundry or textiles, of a water-soluble or water-dispersible sulfo-functional copolyester essentially comprising units of general formula (I) [-0-C(0)-A-C(0)-(0-CH 2 -CH 2 -) n -] (I) where . the symbol A represents
  • n is 1, 2, 3 or 4
  • the molar percentage of the subunits of formula (0-CH 2 -CH 2 -) n i n which n is 1 relative to the sum of the subunits of formula (0-CH 2 -CH 2 -) n in which n is 1, 2, 3 and 4 in the subunits of formula (I) being of the order of from 10 to 80, preferably of the order of from 20 to 60 ; and the ponderal molecular mass of said copolyesters being less than 20,000, preferably less than 15,000, especially from 5000 to 10,000; as a retainer of fragrances on said treated surfaces, especially as a fragrance retainer on laundry or textiles after washing it or them using said composition.
  • the ponderal molecular masses are measured by gel permeation chromatography in dimethylacetamide containing 10 "2 N of LiB
  • nonionic radicals As examples of nonionic radicals (NA) , mention may be made of nonionic C 6 -C 14 mono- or polyarylene radicals and nonionic C ⁇ -Cg alkylene radicals such as the radicals 1, 4-phenylene, 1, 3-phenylene, 1, 6-naphthalene, 1, 6-cyclohexylene, ethylene, trimethylene, tetramethylene and hexamethylene .
  • SA sulfo-functional radicals
  • sulfo-functional C 6 -C ⁇ 4 mono- or polyarylene radicals and sulfo-functional C ⁇ C? alkylene radicals which carry at least one sulfomc acid function, preferably m the form of a sulfonate of an alkali metal, especially sodium, such as sodio- oxysulfonyiphenylene, sodio-oxysulfonylnaphthalene, sodio-oxysulfonylbiphenylene and sodio-oxysulfoethylene radicals,
  • the nonionic radical (NA) is a 1, 4-phenylene (NA1) or 1, 3-phenylene (NA2) radical and the sulfo-functional radical (SA) a 5-sodio- oxysulfonyl-1 , 3-phenylene radical .
  • the radicals (NA) of the nonionic units of formula (I) are 1, 4-phenylene radicals (NA1) or a mixture of 1, 4-phenylene (NA1) and 1, 3-phenylene (NA2) radicals, the molar percentage of the subunits of formula -C (0) -A-C (0) - where A is a radical (NA1) relative to the sum of the subunits of formula -C (0) -A-C (0) - where A is a nonionic radical (NA) being of the order of from 50 to 100, preferably from 70 to 90.
  • Said sulfo-functional copolyesters can be obtained conventionally; for example, by esterification and/or transesterification and polycondensation of a monomer composition based: - on a nonsulfo-functional diacid monomer
  • MNA consisting of at least one aromatic or aliphatic dicarboxylic acid or anhydride, diesters thereof, in an amount corresponding to a molar ratio (MNA) / (MNA) + (MSA) of the order of from 95/100 to 60/100, preferably of the order of from 93/100 to 65/100
  • a sulfo-functional diacid monomer consisting of at least one sulfo-functional aliphatic or sulfo-functional aromatic dicarboxylic acid or anhydride or diesters thereof, in an amount corresponding to a molar ratio (MSA) / (MNA) + (MSA) of the order of from 5/100 to 40/100, preferably of the order of from 7/100 to 35/100
  • a polyol monomer (P) comprising ethylene glycol and optionally diethylene glycol, in an amount corresponding to a ratio of the number of OH functions of the polyol monomer (P) to the number of COOH functions or COOH-function equivalents of the diacid monomers (MNAr) + (MSAr ) of the order of from 1.05 to 4, preferably of the order of from 1.1 to 3.5, and especially of the order of from 1.8 to 3.
  • MNA mole of monomer
  • MSA mole of monomer
  • nonsulfo-functional diacid monomers mention may be made of terephthalic, isophthalic, 2, 6-naphthalenedicarboxylic, cyclohexanedicarboxylic, succinic, glutaric, adipic and suberic acid, and their anhydrides or lower diesters.
  • the nonsulfo-functional diacid monomer consists preferably of from 50 to 100 molar %, especially of from 70 to 90 molar %, of terephthalic acid or anhydride or of one of its lower diesters (methyl, ethyl, propyl, isopropyl or butyl diesters) and of from 0 to 50 molar %, especially from 10 to 30 molar %, of isophthalic acid or anhydride or of one of its lower diesters (methyl, ethyl, propyl, isopropyl or butyl diesters); the preferred diesters are those of methyl.
  • the sulfo-functional diacid monomer has at least one sulfonic acid group, preferably in the form of a sulfonate of an alkali metal (preferably sodium) and two acid functions or acid-function equivalents (that is, one anhydride function or two ester functions) attached to one or more aromatic rings when said monomer is aromatic.
  • an alkali metal preferably sodium
  • two acid functions or acid-function equivalents that is, one anhydride function or two ester functions
  • the sulfonic acid group can be bonded to a carbon atom of an alkylene radical either directly or indirectly via an alkylene, alkoxyalkylene, oxyalkylene, arylalkylene, alkylarylalkylene or alkoxyarylene group.
  • sulfo-functional diacid monomers examples include aliphatic or aromatic sulfo-functional dicarboxylic acids such as sulfoisophthalic, sulfoterephthalic, sulfoorthophthalic, 4-sulfonaphthalene-2, 7-dicarboxylic, sulfodiphenyldicarboxylic and sulfosuccinic acids and their anhydrides or lower diesters.
  • aliphatic or aromatic sulfo-functional dicarboxylic acids such as sulfoisophthalic, sulfoterephthalic, sulfoorthophthalic, 4-sulfonaphthalene-2, 7-dicarboxylic, sulfodiphenyldicarboxylic and sulfosuccinic acids and their anhydrides or lower diesters.
  • the preferred sulfo-functional diacid monomers are sulfoisophthalic acids or anhydrides and their methyl diesters, and especially dimethyl 5-sodio-oxysulfonyl- isophthalate .
  • Said sulfo-functional copolyesters can be obtained by the usual processes of esterification and/or transesterification and polycondensation; for example, by esterification and/or transesterification reaction, in the presence of an esterification/ transesterification catalyst, of the polyol monomer (P) with the various diacid monomers, each diacid being in the acid or anhydride form or in the form of one of its diesters, and polycondensation of the polyol esters under reduced pressure in the presence of a polycondensation catalyst.
  • said sulfo-functional copolyesters are obtained by conducting the following successive steps:
  • transesterification (interchange) step between, on the one hand, the sulfo-functional diacid monomer (MSA) , in diester form, and from 50 to 100 molar %, especially from 30 to 90 molar %, of the total amount of the nonsulfo-functional diacid monomer (MNA) , in diester form, and, on the other hand, an amount of polyol monomer (P) corresponding to a ratio of the number of OH functions of the polyol monomer (P) to the number of COOH-function equivalents of said monomers (MNA) and (MSA) , in diester form, of the order of from 1.05 to 4, preferably of the order of from 1.1 to 3.5, and especially of the order of from 1.8 to 3.0 - an optional step of esterification between the optional remaining amount of the nonsulfo- functional diacid monomer (MNA) , in diacid or anhydride form, and an amount of polyol monomer (P
  • the sulfo-functional (MSA) and nonsulfo- functional (MNA) dicarboxylic diesters employed in the transesterification (interchange) step are preferably methyl diesters.
  • the preferred sulfo-functional copolyesters can be obtained from
  • MNA1 - terephthalic acid
  • MNA2 isophthalic acid
  • transesterification (interchange) step between, on the one hand, the diester (preferably methyl diester) of terephthalic acid (MNA1) and the diester (preferably methyl diester) of sulfoisophthalic acid (MSA) and, on the other hand, monoethylene glycol (P), the ratio of the number of OH functions (P) to the number of COOH-function equivalents of (MNA1)+(MSA) being of the order of from 1.05 to 4, preferably of the order of from 1.1 to 3.5, and especially of the order of from 1.8 to 3
  • MNA1 terephthalic acid
  • MSA sulfoisophthalic acid
  • P monoethylene glycol
  • the ratio of the number of OH functions (P) to the number of COOH-function equivalents of (MNA1)+(MSA) being of the order of from 1.05 to 4, preferably of the order of from 1.1 to 3.5, and especially of the order of from 1.8 to 3
  • MNA2 isophthalic acid
  • P monoethylene glycol
  • subunits may additionally be present at the chain ends, and m minor amounts, such as groups of formula -A-CO-OH (II' i) where A is as defined above.
  • said sulfo- functional copolyesters carry at the chain ends identical or different groups selected from those of formula (Hi) to (II 4 ) of formula
  • Z represents a C 2 -C 3 ⁇ alkyloyl or aryloyl group, optionally carrying an amomc function, preferablv sulfonate, such as sulfobenzoyl M0 3 SC 6 H 4 C (0) - where M is an alkali metal .
  • Z' represents a polyalkoxysulfonate group, m particular of formula (M0 3 S) (CH 2 ) q (CH 2 -CH 2 -0) (RO) r -, where M is an alkali metal, q is 0 or 1, R is an ethylene or propylene group, and r ranges from 0 to 2 .
  • Chain ends of a formula of the type (II 2 ), (II 3 ) and (II 4 ) can be obtained by employing monoacid monomers for the chain ends of formula (II 2 ), a hydroxypolyalkoxy- alkylsulfonate for the chain ends of formula (II 3 ), and a polyalkylene glycol monoether or a monoacid for the chain ends of formula (II 4 ) .
  • Said sulfo-functional copolyesters can be employed as retainers of fragrances on surfaces, especially on laundry or polyester-based textiles in particular, in detergent compositions for surface treatment, in particular for washing laundry and polyester-based textiles in particular, in a proportion of from 0.01 to 10%, preferably from 0 05 to 5%, especially from 0.1 to 1% of the weight of said detergent composition.
  • fragrances can be present in the detergent compositions in a proportion of from 0.05 to 1%, preferably from 0.1 to 0.5% by weight.
  • Said detergent compositions can be compositions for the treatment of hard surfaces, such as those of ceramic, glass, porcelain, formica or another hard polymer, especially for cleaning crockery, bathrooms, kitchens, etc. They further comprise at least one surfactant, preferably anionic, nonionic or amphoteric.
  • the detergent compositions concerned are for the hand or machine washing of laundry or textiles.
  • Said detergent compositions for laundry or textiles in which said sulfo-functional copolyesters can be employed as fragrance retainers may further comprise customary constituents such as:
  • surfactants preferably anionic, nonionic or amphoteric, in an amount of the order of from 5 to 70%, preferably from 5 to 50% of the weight of said composition, surfactants such as: anionic surfactants, for instance
  • alkyl ester sulfonates of formula R-CH ( S0 3 M) -COOR' where R' represents a C 8 _ 20 , preferably C ⁇ 0 -C 16 , alkyl radical, R' a preferably C ⁇ C 3 , alkyl radical and M an alkali metal cation (sodium, potassium, lithium), substituted or unsubstituted ammonium (methyl-, dimethyl-, t ⁇ methyl-, tetramethylammonium, dimethylpiperidmium, etc.) or a cation derived from an alkanolamme (monoethanolamme, diethanolamme, t ⁇ ethanolamme, etc.);
  • alkyl sulfates of formula ROS0 3 M where R represents a Cs _ C 24 , preferably C ⁇ 0 -C ⁇ 8 , alkyl or hydroxyalkyl radical, M representing a hydrogen atom or a cation as defined above, and also ethoxylenated (EO) and/or propoxylenated (PO) derivatives thereof, having on average from 0.5 to 30, preferably from 0.5 to 10, EO and/or PO subunits; . alkyla ide sulfates of formula RCONHR'OS0 3 M where R represents a C 2 -C 22 , preferably C 6 -C 20 , alkyl radical and R' a C 2 -C 3 alkyl radical,
  • M representing a nydrogen atom or a cation as defined above, and also ethoxylenated (EO) and/or propoxylenated (PO) derivatives thereof, having on average from 0.5 to 60 EO and/or PO subunits; .
  • EO ethoxylenated
  • PO propoxylenated
  • C 8 -C 24 saturated or unsaturated C 8 -C 24 , preferably C ⁇ 4 -C 20 / fatty acid salts, C 9 -C 20 alkylbenzenesulfonates, primary or secondary C 8 -C 22 alkylsulfonates , alkylglycerol- sulfonates, the sulfo-functional polycarboxylic acids described m GB-A-1 082 179, paraffmsulfonates, N- acyl-N-alkyltaurates, alkyl phosphates, lsethionates, alkylsuccmamates alkylsulfosuccmates, monoesters or diesters of sulfosuccmates, N-acylsarcosmates, alkylglycoside sulfates and polyethoxycarboxylates the cation being an alkali metal (sodium, potassium, lithium) , a substituted or unsubstit
  • sophorolipids such as those m acid or lactone form which are derived from 17-hydroxyoctadecen ⁇ c acid; nonionic surfactants, for instance .
  • polyoxyalkyenated C 8 -C 22 aliphatic alcohols containing 1 to 25 oxyalkylene (oxyethylene, oxypropylene) units by way of example, mention may be made of TERGITOL 15-S-9 and TERGITOL 24-L-6 NMW marketed by Union Carbide Corp., NEODOL 45-9, NEODOL 23-65, NEODOL 45-7, and NEODOL 45-4 marketed by Shell Chemical Cy, KYRO EOB marketed by The Procter & Gamble Cy, SYNPERONIC A3 to A9 from ICI, and RHODASURF IT, DB and B from RHONE- POULENC;
  • products resulting from the condensation of ethylene oxide or propylene oxide with ethylenediamine such as the TETRONICS marketed by BASF;
  • alkoxylated amidoamines containing 1 to 50, preferably 1 to 25, especially 2 to 20 oxyalkylene (preferably oxyethylene units;
  • amine oxides such as C 10 -C 18 -alkyldimethylamine oxides and C 8 -C 22 -alkoxyethyldihydroxyethylamine oxides; . alkoxylated terpenic hydrocarbons such as ethoxylated and/or propoxylated a- or b- pmenes containing 1 to 30 oxyethylene and/or oxypropylene units; .
  • alkylpolyglycosides obtainable by condensation (for example, by acid catalysis) of glucose with primary fatty alcohols (US-A-3 598 865; US-A-4 565 647; EP-A-132 043, EP-A-132 046, etc.) having a C 4 -C 20 , preferably C 8 -C ⁇ 8 , alkyl group and an average number of glucose units of the order from 0.5 to 3, preferably of the order of 1.1 to 1.8 per mole of alkypolyglycoside (APG) ; mention may be made particular of those having
  • GLUCOPON 600 CSUP GLUCOPON 650 EC , GLUCOPON 225 CSUP
  • amphot eric surfactant s for inst ance alkylbetames , alkyldimethylbet a es , alkylamidopropylbetames , alkylamidopropyldimethylbeta es , alkyltrimethyl- sulfobetames , lmidazolme derivatives such as alkylamphoacetates, alkyla phodiacetates, alkylampho- propionates, alkylamphodipropionates, alkylsultames or alkylamidopropylhydroxysultames, condensation products of fatty acids and protein hydrolysates, amphoteric derivatives of alkylpolyammes such as Amphionic XL ®,
  • detergency adjuvants such as
  • polyphosphates tripolyphosphates, pyrophosphates, orthophosphates, hexametaphosphates ) of alkali metals, of ammonium or of alkanolammes
  • alkali metal or alkaline earth metal carbonates (bicarbonates, sesquicarbonates)
  • glutamic acid for instance, N, N-bis ( carboxymethyl) glutamic acid and its salts, especially sodium salts
  • other ammo acids for instance, N, N-bis ( carboxymethyl) glutamic acid and its salts, especially sodium salts
  • - ammophosphonates such as nitrilot ⁇ s (methylene- phosphonates)
  • m amounts of the order of 0.01-10%, preferably of the order of from 0.1 to 5%, and especially of the order of 0.2-3% by weight, agents such as
  • cellulose derivatives such as cellulose hydroxyethers, methylcellulose, ethylcellulose, hydroxypropylmethylcellulose and hydroxybutyl- methylcellulose
  • polyester copolymers based on ethylene terephthalate and/or propylene terephthalate and polyoxyethylene terephthalate units, w th an ethylene terephthalate and/or propylene terephthalate (number of units) /poloxyethylene terephthalate (number of units) ratio of the order of from 1/10 to 10/1, the polyoxyethylene terephthalate units having polyoxyethylene subunits havmg a molecular weight of the order of from 300 to 10,000, with a molecular mass of the copolyester of the order of from 1000 to 100,000
  • polyester oligomers obtained by sulfonation of an oligomer derived from ethoxylated allyl alcohol, dimethyl terephthalate and 1,2- propylenediol, having from 1 to 4 sulfo-functional groups (US-A-4 968 451) .
  • - antiredeposition agents m amounts of approximately 0.01-10% by weight for a powder detergent composition and approximately 0.01-5% by weight for a liquid detergent composition, agents such as
  • - sulfo-functional polyester oligomers obtained by condensation of isophthalic acid, dimethyl sulfosuccmate and diethylene glycol (FR-A-2 236 926) ; - bleaches m an amount of approximately 0.1-20%, preferably 1-10% of the weight of said powder detergent composition, such as
  • peroxygenated compounds such as sodium carbonate peroxyhydrate, pyrophosphate peroxyhydrate, urea peroxyhydrate, sodium peroxide and sodium persulfate - percarboxylic acids and their salts (which are called "percarbonates” ) such as magnesium monoperoxyphthalate hexahydrate, magnesium metachloroperbenzoate, 4-nonylammo-4-oxo- peroxybutyric acid, 6-nonylammo-6-oxoperoxycapro ⁇ c acid, diperoxydodecanedioic acid, peroxysuccmic acid nonyl amide, and decyldiperoxysuccmic acid, preferably combined with a bleach activator which generates a carboxylic peroxy acid m situ m the washing medium; among these activators, mention may be made of tetraacetylethylenediamme, tetraacetyl- methylened amme, tetraacetylglycoluryl, sodium p-
  • n an amount of approximately 0.05 to 5% by weight, for instance .
  • polyvmylpyrrolidones . copolymers of N-vmylpyrrolidone and N-vmylimidazole . polyamine N-oxides
  • agents such as stilbene derivatives, pyrazoline, coumarin, fumaric acid, cinnamic acid, azoles, methinecyanines, thiophenes, etc. foam suppressants in amounts possibly ranging up to 5% by weight, agents such as
  • enzymes in an amount possibly ranging up to 5 mg by weight, preferably of the order of 0.05-3 mg of active enzyme/g of detergent composition, enzymes such as proteases, amylases, lipases, peroxydases, cellulase (US-A-3 553 139, US-A-4 101 457, US-A-4 507 219, US-A-4 261 868, US-A-4 , 435 , 307 , GB-A-2 075 028, GB-A-2 095 275, GB-A-1 368 599, WO 92/13057) and other additives such as
  • buffers or fillers such as sodium sulfate and the carbonates or bicarbonates of alkaline earth metals .
  • said detergent compositions are substantially devoid of polyorganosiloxane compounds which carry ammo functions.
  • the present invention also provides a process for cleaning surfaces, especially laundry or textiles, using a detergent composition comprising a fragrance and a water-soluble or water-dispersible sulfo- functional copolyester of formula (I) m an amount which is effective for prolonging the persistence of said fragrance on said surfaces after cleaning.
  • Said detergent composition is substantially devoid of polyorganosiloxane compounds which carry ammo functions .
  • the invention more particularly provides a process for washing laundry or textiles using a washing me ⁇ ium comprising a fragrance and a water-soluble or water-dispersible sulfo-functional copolyester of formula (I) m an amount which is effective for prolonging the persistence of said fragrance on said laundry or said textiles after washing.
  • the washing operation can be conducted at a temperature of the order of from 20 to 90°C, preferably from 30 to 60°C.
  • Said detergent composition is substantially devoid of polyorganosiloxane compounds which carry ammo functions .
  • the sulfo-functional copolyester thus obtained is employed within the detergent composition for the machine washing of laundry, featuring in the following table.

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Abstract

L'invention concerne l'utilisation, dans une composition de détergent contenant un parfum et destinée au traitement de surfaces, et tout particulièrement au lavage de linge ou de textiles, d'un copolyester hydrosoluble ou d'un copolyester sulfo-fonctionnel dispersable dans l'eau, comme élément servant à retenir les parfums sur lesdites surfaces traitées.
PCT/EP2000/009340 1999-09-28 2000-09-13 Utilisation dans une composition de detergent d'un copolyester sulfo-fonctionnel comme element permettant de retenir le parfum Ceased WO2001023512A1 (fr)

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Application Number Priority Date Filing Date Title
AU76591/00A AU7659100A (en) 1999-09-28 2000-09-13 Use in a detergent composition of a sulfo-functional copolyester as fragrance retainer

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US15638499P 1999-09-28 1999-09-28
US60/156,384 1999-09-28
US18554000P 2000-02-28 2000-02-28
US60/185,540 2000-02-28

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2682454A1 (fr) 2012-07-04 2014-01-08 InnovaTec Sensorización y Communication S.L. Procédé et composition d'infusion d'un ingrédient actif dans des tissus et utilisation d'un agent liant pour les microcapsules de ladite composition
EP2745878A1 (fr) * 2012-12-19 2014-06-25 Symrise AG Compositions cosmétiques
CN109320440A (zh) * 2018-11-20 2019-02-12 上海炼升化工股份有限公司 一种合成间苯二甲酸二乙二醇酯-5-磺酸钠的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019448A1 (fr) * 1993-02-26 1994-09-01 The Procter & Gamble Company Additifs de blanchissage comprenant des parfums encapsules et des polyesters modifies
EP0989183A2 (fr) * 1998-08-19 2000-03-29 Henkel KGaA Fixage de perfumes aux surfaces dures et douces
FR2791992A1 (fr) * 1999-04-12 2000-10-13 Rhodia Chimie Sa Systeme multi-particulaire vecteur de matiere(s) active(s), sa preparation et ses utilisations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994019448A1 (fr) * 1993-02-26 1994-09-01 The Procter & Gamble Company Additifs de blanchissage comprenant des parfums encapsules et des polyesters modifies
EP0989183A2 (fr) * 1998-08-19 2000-03-29 Henkel KGaA Fixage de perfumes aux surfaces dures et douces
FR2791992A1 (fr) * 1999-04-12 2000-10-13 Rhodia Chimie Sa Systeme multi-particulaire vecteur de matiere(s) active(s), sa preparation et ses utilisations

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2682454A1 (fr) 2012-07-04 2014-01-08 InnovaTec Sensorización y Communication S.L. Procédé et composition d'infusion d'un ingrédient actif dans des tissus et utilisation d'un agent liant pour les microcapsules de ladite composition
EP2745878A1 (fr) * 2012-12-19 2014-06-25 Symrise AG Compositions cosmétiques
US9708566B2 (en) 2012-12-19 2017-07-18 Symrise Ag Cosmetic compositions
CN109320440A (zh) * 2018-11-20 2019-02-12 上海炼升化工股份有限公司 一种合成间苯二甲酸二乙二醇酯-5-磺酸钠的方法

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