WO2004048506A1 - Dye transfer inhibitors for laundry detergents - Google Patents
Dye transfer inhibitors for laundry detergents Download PDFInfo
- Publication number
- WO2004048506A1 WO2004048506A1 PCT/US2003/038680 US0338680W WO2004048506A1 WO 2004048506 A1 WO2004048506 A1 WO 2004048506A1 US 0338680 W US0338680 W US 0338680W WO 2004048506 A1 WO2004048506 A1 WO 2004048506A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sulfonic acid
- detergent
- hydrocarbyl
- dye transfer
- polymer
- Prior art date
Links
- 238000012546 transfer Methods 0.000 title claims abstract description 45
- 239000003112 inhibitor Substances 0.000 title claims abstract description 38
- 239000003599 detergent Substances 0.000 title claims description 46
- -1 hydrocarbyl sulfonic acid Chemical compound 0.000 claims abstract description 52
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 35
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000003222 pyridines Chemical class 0.000 claims abstract description 18
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims abstract description 17
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000004900 laundering Methods 0.000 claims abstract description 6
- 239000000975 dye Substances 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 50
- 239000000178 monomer Substances 0.000 claims description 33
- 239000004744 fabric Substances 0.000 claims description 21
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 13
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- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- VKZRWSNIWNFCIQ-UHFFFAOYSA-N 2-[2-(1,2-dicarboxyethylamino)ethylamino]butanedioic acid Chemical compound OC(=O)CC(C(O)=O)NCCNC(C(O)=O)CC(O)=O VKZRWSNIWNFCIQ-UHFFFAOYSA-N 0.000 description 2
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- 102000004882 Lipase Human genes 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000004965 Silica aerogel Substances 0.000 description 1
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- 229920002472 Starch Polymers 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- 235000019418 amylase Nutrition 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- RLYNGYDVXRKEOO-SQQVDAMQSA-N but-2-enoic acid;(e)-but-2-enoic acid Chemical compound CC=CC(O)=O.C\C=C\C(O)=O RLYNGYDVXRKEOO-SQQVDAMQSA-N 0.000 description 1
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
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- 239000013522 chelant Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
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- 239000004927 clay Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- OQEVSCYDUYRAAM-UHFFFAOYSA-N disodium;oxido-[oxido(oxo)silyl]oxy-oxosilane Chemical compound [Na+].[Na+].[O-][Si](=O)O[Si]([O-])=O OQEVSCYDUYRAAM-UHFFFAOYSA-N 0.000 description 1
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- PMYUVOOOQDGQNW-UHFFFAOYSA-N hexasodium;trioxido(trioxidosilyloxy)silane Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])O[Si]([O-])([O-])[O-] PMYUVOOOQDGQNW-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- UNNFEYPNQVSVJX-UHFFFAOYSA-N pentane-3-sulfonic acid Chemical compound CCC(CC)S(O)(=O)=O UNNFEYPNQVSVJX-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- 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
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/378—(Co)polymerised monomers containing sulfur, e.g. sulfonate
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0021—Dye-stain or dye-transfer inhibiting compositions
Definitions
- the present invention generally relates to water-soluble dye transfer inhibitors (DTI) and their use in washing textiles and related processes.
- One component is a hydrocarbyl substituted pyridine in monomer, oligomer or polymer form.
- a second component is a hydrocarbyl sulfonic acid such as 2-acrylamido-2- methylpropane sulfonic acid (AMPS®) monomer.
- AMPS® 2-acrylamido-2- methylpropane sulfonic acid
- the first and second components interact with each other as a reaction product or a salt.
- Dye transfer inhibitors are characterized by their ability to inhibit the tendency of colored fabrics to transfer dye to other fabrics or to other portions of the same fabric during laundering.
- the mechanism of dye transfer inhibitors is typically to complex or adsorb fugitive dyes in the wash liquor so as to prevent them from re-depositing onto fabrics that did not originally have those dyes.
- U.S. Patent 5,607,618 to Hoechst Aktiengesellschaft discusses the use of water-soluble copolymers, based on acrylamidoalkylenesulfonic acid, vinylacetamide, and, if appropriate, other monomers, as a detergent additive for preventing reabsorption of detached dyestuffs and dyestuff degradation products.
- a dye fixative compositions comprising a) polymethacrylic acid, b) copolymers of methacrylic acid with specified other monomers, c) sulfamic acid, and combinations of a, b, and c.
- U.S. Patent 6,159,921 to Henkel Corp. discloses a detergent composition comprising an alkali component selected from a group, a dye transfer inhibition additive selected from the group consisting of (i) a sugar surfactant selected from alkyl polyglycosides having a particular formula, (ii) an alkyl sulfate, (iii) an aminocarboxylic acid amphoteric surfactant, and (iv) mixtures of (i), (ii), and (iii).
- US 6,306,815 to National Starch and Chemical Investment Holding Corp. discloses water-soluble quaternary polyvinylpyrridinium derivative which inhibits dye transfer in detergent compositions without adversely affecting stain or soil removal or soil redeposition.
- U.S. Patent 6,432,909 to ISP Investments Inc. discloses dye complexing polymers such as isopropenylpyridine betaines containing a quaternary nitrogen and a carboxylate salt or carboxylic acid group that have effective dye complexing properties for use, for example, in laundry detergent and fabric softener compositions.
- polymers which have been used in detergent compositions to inhibit dye transfer include polyvinylimidazole, polyvinylpyridine N-oxide, and copolymers of polyvinylpyridine and polyvinylimidazole.
- DE 2 814 287-A describes detergent compositions containing N-vinyl imidazole homo- or copolymer in combination with anionic and/or nonionic surfactants and other detergent ingredients.
- WO 95/03390 describes dye inhibiting polymers of polyvinylpyrrolidone, polyamine N- oxide, and vinylimidazole.
- U.S. Patent No. 5,460,752 describes polyamine N-oxide polymers.
- Patent 5,627,151 describes copolymers of vinylpyrrolidone or vinylimidazole, vinylpyridine or dimethylaminoethyl methacrylate or dimethylaminopiOpyl-methacrylamide, including up to 20% vinylacetate, for use in laundry detergents.
- U.S. Patent No. 5,466,802 describes poly(4-vinylpyridine-N- oxide) and copolymers of vinylpyrrolidone and vinylimidazole.
- EP 754748 describes vinylpyridine copolymers and formic acid.
- U.S. Patent No. 5,458,809 describes poly(4-vinylpyridine-N-oxide).
- WO 95/27038 describes poly(4- vinylpyridine-N-oxide), polyvinylpyrrolidone, polyvinylpyrrolidone-vinylimidazole and copolymers of vinylpyrrolidone and vinylimidazole.
- EP 372 291 describes a process for washing discoloration-sensitive textiles.
- the wash liquor contains anionic/nonionic surfactants and water-soluble polymers, for example, copolymers of N-vinylimidazole, N-vinyloxazolidone or N- vinylpyrrolidone.
- EP 327 927 describes a granular detergent additive comprising water-soluble polymeric compounds based on N-vinylpyrrolidone and or N- vinylimidazole and or N-vinyloxazolidone and cationic compounds.
- DE 4027832 describes electrolyte-free liquid detergent compositions comprising zeolite A, nonionic surfactants and homo- and copolymers selected from N-vinylpyrrolidone and/or N-vinylimidazole and/or N-vinyloxazolidone.
- U.S. Patent No. 5,776,879 describes water-soluble poly(vinylpyridine betaines) containing a quaternary nitrogen and a carboxylate salt, which have effective dye transfer inhibitor properties.
- U.S. Patent Application Serial No. 09/300,913, filed April 28, 1999 describes polyvinylpyrridinium derivatives containing a quaternary nitrogen and an anionic moiety selected from a sulfonate or a carboxylate functionality, for use in detergent compositions.
- the invention provides dye transfer inhibitors that are more effective at minimizing redeposition of fugitive dyes and fugitive dye degradation products than prior art dye transfer inhibitors.
- the dye transfer inhibitors of the invention comprise a combination of a) hydrocarbyl substituted pyridine or a polymer or oligomer including vinylpyridine monomer units and b) a hydrocarbyl sulfonic acid such as 2-acrylamido-2-methylpropane sulfonic acid monomer or a polymer formed from said monomer.
- the a) and b) components can react together to form an adduct where the ⁇ -carbon of the vinyl portion of the vinylpyridine or 2- acrylamido-2-methylpropane sulfonic acid chemically bonds to the nitrogen atom of the pyridine.
- the sulfonic acid of the hydrocarbyl sulfonic acid such as 2-acrylamido-2-methylpropane sulfonic acid can protonate the nitrogen of the pyridine and then the cationic protonated nitrogen atom can form an ionic salt with the anionic sulfonic group of the 2-acrylamido-2-methylpropane sulfonic acid.
- the dye transfer inhibitors of this invention do not include copolymer having backbone repeating units of both vinylpyridine and 2-acrylamido- 2-methylpropane sulfonic acid when the copolymers contain certain protonated pyridinium species disclosed in US 6,306,815.
- hydrocarbyl substituted pyridine and the 2-acrylamido-2-methylpropane sulfonic acid can be contained
- the hydrocarbyl substituted pyridine e.g. vinyl pyridine monomer or the repeat units from polymerizing vinylpyridine is present in the final detergent or soap composition at a concentration from about 0.1 percent to about 50 percent based on the weight of the detergent.
- the hydrocarbyl sulfonic acid such as 2-acrylamido-2-methylpropane sulfonic acid is present at a molar ratio of from about 0.5 to about 5 relative to the moles of hydrocarbyl substituted pyridine e.g. vinylpyridine monomer or repeat units from polymerizing the hydrocarbyl substituted pyridine.
- Other components common to laundry or other textile cleaning products may be included in the final composition for their conventional purposes.
- This invention relates to water-soluble dye transfer inhibitors.
- the compounds are useful as dye transfer inhibitors and color protection agents in detergent compositions, especially detergent compositions containing a high level of anionic surfactants.
- hydrocarbyl sulfonic acids can be the AMPS® monomer (2-acrylamido-2-methylpropane sulfonic acid) which has the formula shown below.
- hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
- hydrocarbyl groups include:
- hydrocarbon substituents that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring);
- aliphatic e.g., alkyl or alkenyl
- alicyclic e.g., cycloalkyl, cycloalkenyl
- aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring);
- substituted hydrocarbon substituents that is, substituents containing non- hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
- hetero substituents that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms.
- Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents as pyridyl, furyl, thienyl and imidazolyl.
- no more than three, preferably no more than one or two, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; typically, there will be no non-hydrocarbon substituents in the hydrocarbyl group.
- hydrocarbyl sulfonic acids When hydrocarbyl sulfonic acids are described it is preferred that the hydrocarbyl group have from about 6 to about 20 carbon atoms. This description would be relevant to the hydrocarbyl sulfonic acid as a compound (including monomer) or as a repeat unit in a larger oligomer or polymer. However when referring to a polymer that contains a hydrocarbyl sulfonic acid, only the hydrocarbyl sulfonic acid repeat unit will be required to have the specified number of carbon atoms (i.e. the average number of carbon atoms per sulfonic acid in the polymer will not be required to fall within the specified range).
- hydrocarbyl sulfonic acids include styrene sulfonic acid, methallyl sulfonic acid, vinyl sulfonic acid, allyloxy sulfonic acid, various benzene sulfonic acids, alkyl sulfonic acids, etc.
- Polymers containing repeating units including a portion of hydrocarbyl sulfonic acid e.g. 2-acrylamido-2-n ethylpropane sulfonic acid
- the polymers are water soluble after reacting with the hydrocarbyl substituted pyridine portion of the dye transfer inhibitor.
- hydrocarbyl sulfonic acids do not offer dye transfer inhibition by themselves but must be used in combination with a hydrocarbyl substituted pyridine, in monomer, oligomer, or polymer form.
- the hydrocarbyl substituted pyridine entities are pyridine molecules substituted with the various hydrocarbyl groups discussed above. Desirably for the hydrocarbyl substituted pyridine the hydrocarbyl group has from about 2 to about 10 carbon atoms and is substantially free of heteroatoms other than nitrogen.
- a preferred hydrocarbyl group is a vinyl group and most preferably the vinyl group is para to the nitrogen atom of the pyridine (e.g. 4- vinylpyridine).
- the hydrocarbyl sulfonic acid and the hydrocarbyl substituted pyridine are allowed to react to form the dye transfer inhibitor. They may undergo a chemical reaction forming a new chemical compound (e.g. adduct(s)) or they may react together to form a salt of the basic pyridine and the acidic sulfonic acid. It is known that some of the materials described above may interact in the final formulation. Nevertheless, all such modifications and reaction products are included within the scope of the present invention; the present invention encompasses the composition prepared by admixing the components described above. Either the hydrocarbyl sulfonic acid or the hydrocarbyl substituted pyridine may be used as an oligomer or polymer as well as a low molecular weight compound.
- a new chemical compound e.g. adduct(s)
- the hydrocarbyl substituted pyridine may be used as an oligomer or polymer as well as a low molecular weight compound.
- both of these compounds are readily copolymerizable with a variety of ethylenically unsaturated monomers.
- the ethylenically unsaturated monomers should be carefully selected so that the resulting polymer has reasonable water solubility. Any ethylenically unsaturated monomer may be used. Such monomers are known to those skilled in the art. A combination of ethylenically unsaturated monomers may also be used.
- the ethylenically unsaturated monomers have an anionic charge or become anionic upon treatment with a base.
- examples of such monomers are acrylic acid, sodium salt of 2-acrylamido-2-methyl propane sulfonic acid, sodium methallyl sufonate, sodium vinyl sulfonate, sulfonated styrene, sodium salt of allyloxybenzene sulfonic acid, methacrylic acid, alpha-chloro-acrylic acid, alpha-cyano acrylic acid, alpha-chloro-acrylic acid, alpha-cyano acrylic acid, beta methyl-acrylic acid (crotonic acid), alpha-phenyl acrylic acid, beta-acryloxy propionic acid, sorbic acid, alpha-chloro sorbic acid, angelic acid cinnamic acid, p- chloro cinnamic acid, beta styryl acrylic acid (l-carboxy-4-phenyl butadiene- 1,3),
- the ethylenically unsaturated monomers are nonionic nitrogen containing monomers.
- examples of such monomers are acrylamide, N, N-dimethylacrylamide, N-octyl acrylamide, N-methylol acrylamide, dimethylaminoethylacrylate, vinyl pyrrolidone, vinyl imidazole, N-vinyl formamide,
- the water-soluble hydrocarbyl substituted pyridine e.g. 4-vinylpyridine compound of the invention are made by polymerizing a monomer such as 4- vinylpyridine under suitable polymerization conditions to form a poly(vinylpyridine) intermediate, and then reacting the poly(vinylpyridine) intermediate with a hydrocarbyl sulfonic acid.
- the reaction product is a salt of the poly(4-vinylpyridine) with the hydrocarbyl sulfonic acid.
- the dye transfer inhibitor of the invention is used in detergent compositions.
- the level of the dye transfer inhibitor of the invention in the detergent compositions is from about 0.01 to about 90 weight percent, more preferably from about 0.05 to about 20 weight percent, most preferably from about 0.1 to about 10 weight percent, based on the total weight of the detergent composition.
- the dye transfer inhibitor may be used outside laundry applications in other fabric applications such as in compositions to minimize dye transfer on newly manufactured fabrics, including clothing, upholstery and carpeting. Further the dye transfer inhibitor can be used in other areas where the fabric is contacted with water, e.g. fabric softener treatments or other aqueous treatments of a fabric.
- the detergent composition may be a solid or liquid composition. If the detergent composition is solid, the detergent composition may be in any of the usual physical forms, such as for example, powders, beads, flakes, bars, tablets, noodles, pastes, and slurries. If the detergent composition is liquid, the detergent composition preferably disperses or solubilizes the dye transfer inhibitor.
- the detergent composition may be aqueous or nonaqueous.
- the dye transfer inhibitor may be dissolved or dispersed in water, in one or more solvents or inert diluents.
- the detergent composition is aqueous.
- the detergent compositions may contain any additional components which are used in detergent compositions.
- Such additional components include one or more surfactants, builders, ion exchangers, alkalies, anticorrosion materials, antiredeposition materials, optical brighteners, fragrances, dyes, chelating agents, enzymes, whiteners, brighteners, antistatic agents, sudsing control agents, solvents, hydrotropes, bleaching agents, perfumes, bleach precursors, water, buffering agents, soil removal agents, soil release agents, softening agents, opacifiers, inert diluents, buffering agents, corrosion inhibitors, graying inhibitors, and stabilizers. Combinations of such additional components may also be used.
- Suitable surfactants are nonionic, anionic, cationic, ampholytic, zwitterionic and semi-polar surfactants. A combination of surfactants may also be used.
- Anionic surfactants include, for example, from C 8 to C 20 alkylbenzenesulfonates, from C 8 to C 2 o alkanesulfonates, from C 8 to C 2 o alkylsulfates, from C 8 to C 20 alkylsulfosuccinates or from C8 to C20 sulfated ethoxylated alkanols.
- Nonionic surfactants include, for example, from C 6 to C 12 alkylphenol ethoxylates, from C 8 to C 20 alkanol alkoxylates, and block copolymers of ethylene oxide and propylene oxide.
- the end groups of polyalkylene oxides can be blocked, whereby the free OH groups of the polyalkylene oxides can be etherified, esterified, acetalized and/or aminated.
- Another modification consists of reacting the free OH groups of the polyalkylene oxides with isocyanates.
- the nonionic surfactants also include C 4 to 8 alkyl glucosides as well as the alkoxylated products obtainable therefrom by alkoxylation, particularly those obtainable by reaction of alkyl glucosides with ethylene oxide.
- Cationic surfactants contain hydrophilic functional groups where the charge of the functional groups are positive when dissolved or dispersed in an aqueous solution.
- Typical cationic surfactants include, for example, amine compounds, oxygen containing amines, and quaternary amine salts.
- Amphoteric surfactants contain both acidic and basic hydrophilic groups
- Amphoteric surfactants are preferably derivatives of secondary and tertiary amines, derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds.
- the cationic atom in the quaternary compound can be part of a heterocyclic ring.
- the amphoteric surfactant preferably contains at least one aliphatic group, containing about 3 to about 18 carbon atoms. At least one aliphatic group preferably contains an anionic water-solubilizing group such as a carboxy, sulfonate, or phosphono.
- anionic surfactants such as linear alkyl sulfonates (LAS) are preferred for use in solid detergent compositions containing the dye transfer inhibitor.
- Nonionic and anionic surfactant mixtures such as alcohol ethoxylates and
- LAS are preferred in liquid detergent compositions containing the dye transfer inhibitor.
- the surfactants are optionally present in an amount of from about 0 to about 50 weight percent, preferably from about 2 to about 45 weight percent, and more preferably from about 5 to about 40 weight percent, based on the total weight of the detergent composition.
- bleaching agents are perborates, percarbonates, or chlorine- generating substances such as chloroisocyanurates.
- silicates used as corrosion inhibitors are sodium silicate, sodium disilicate, and sodium metasilicate.
- graying inhibitors are carboxymethylcellulose, methylcellulose, hydroxypropylmethyl-cellulose, and polyacrylic acid and copolymers of acrylic and maleic acid.
- enzymes are proteases, amylases, lipases, cellulases, and peroxidases, as well as mixtures thereof. Other types of enzymes may also be included. They may be of any suitable origin, such as vegetable, animal, bacterial, fungal and yeast origin.
- Any conventional builder system is suitable for use in the detergent composition including aluminosilicate materials, silicates, polycarboxylates and fatty acids, materials such as ethylenediamine tetraacetate, metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid.
- aluminosilicate materials silicates, polycarboxylates and fatty acids
- materials such as ethylenediamine tetraacetate
- metal ion sequestrants such as aminopolyphosphonates, particularly ethylenediamine tetramethylene phosphonic acid and diethylene triamine pentamethylenephosphonic acid.
- phosphate builders can also be used herein.
- Suitable builders can be an inorganic ion exchange material, commonly an inorganic hydrated aluminosilicate material, more particularly a hydrated synthetic zeolite such as hydrated zeolite A, X, B or HS.
- Another suitable inorganic builder material is layered silicate, e.g., SKS-6 (Hoechst).
- SKS-6 is a crystalline layered silicate consisting of sodium silicate (Na2Si2O5).
- the preferred polycarboxylates are hydroxycarboxylates containing up to three carboxy groups per molecule, more particularly citrates.
- Preferred builder systems for use in the detergent compositions include a mixture of a water-insoluble aluminosilicate builder such as zeolite A or of a layered silicate (SKS/6), and a water-soluble carboxylate chelating agent such as citric acid.
- a water-insoluble aluminosilicate builder such as zeolite A or of a layered silicate (SKS/6)
- a water-soluble carboxylate chelating agent such as citric acid.
- a suitable chelant for inclusion in the detergent compositions is ethylenediamine-N,N'-disuccinic acid (EDDS) or the alkali metal, alkaline earth metal, ammonium, or substituted ammonium salts thereof, or mixtures thereof.
- EDDS ethylenediamine-N,N'-disuccinic acid
- Examples of suds suppressors are silicones and silica-silicone mixtures. Silicones can be generally represented by alkylated polysiloxane materials while silica is normally used in finely divided forms exemplified by silica aerogels and xerogels and hydrophobic silicas of various types.
- Examples of antiredeposition and soil suspension agents are cellulose derivatives such as methylcellulose, carboxymethylcellulose and hydroxyethylcellulose, and homopolymers of acrylic acid and copolymers of maleic acid and acrylic acid.
- optical brighteners examples include disodium 4,4-bis-(2-diethanolamino-4- anilino-s-triazin-6-ylamino)stilbene-2:2disulphonate, disodium 4,-4-bis-(2- morpholino-4-anilino-s-triazin-6-ylaminostilbene-2:2-disulphonate, disodium 4,4- bis-(2,4-dianilino-s-triazin-6-ylamino)stilbene-2:2-disulphonate, monosodium 4,4- bis-(2,4-dianilino-s-triazin-6ylamino)stilbene-2-sulphonate, disodium 4,4-bis-(2- anilino-4-(N-methyl-N-2-hydroxyethylamino)-s-triazin-6-ylamino)stilbene-2,2- disulphonate, disodium 4,4-bis-(4-phenyl-2,l,3-triazol-2-y
- 2,2disulphonate disodium 4,4bis(2-anilino-4-(l-methyl-2-hydroxyethylamino)-s- triazin-6-ylamino)stilbene-2,2disulphonate, and sodium 2(stilbyl-4-(naphtho- 1, 2:4,5)- l,2,3-triazole-2-sulphonate.
- polyethylene glycols particularly those of molecular weight 1000-
- soil release agents are conventional copolymers or terpolymers of terephthalic acid with ethylene glycol and/or propylene glycol units in various arrangements, as well as the ethoxylated/propoxylated polyamines.
- Modified polyesters may also be used as soil release agents, and include random copolymers of dimethyl terephtalate, dimethyl sulfoisophtalate ethylene glycol and 1-2 propane diol, the end groups consisting primarily of sulphobenzoate and secondarily of mono esters of ethylene glycol and or propane-diol.
- Example 1 4-vinylpyridine (5 grams) and AMPS monomer (9.85 grams) were combined in 50 grams of methanol. The clear solution was stirred at room temperature for 3 hours and subsequently for 5 hours at 60-65°C. The volatiles were removed with a rotary evaporator to give a light pink solid.
- Example 2 4-vinyl ⁇ yridine (10.5 grams), water (50 grams) and AMPS (20.7 grams) were combined at room temperature until all of the AMPS was dissolved. The reaction was exothermic and stirring was continued for 1 hour. The product was a light red solution.
- AMPS (2.07) (grams) was added. The mixture was stirred at 30-40°C for 15 minutes. The clear solution contained 10% water. The AMPS/ Poly-4- vinylpyridine content could be varied.
- hydrocarbyl group is shown in the para position to the nitrogen atom of the vinylpyridine, but the hydrocarbyl may be in the ortho or meta positions.
- adduct is shown as being a single 4-Vinylpyridine with a single AMPS molecule, further study has indicated a major amount of an adduct or oligomer from adding the vinyl group from a 4-vinylpyridine to the nitrogen of another 4-vinylpyridine.
- Red 80 was the dye used in carrying out the testing.
- the effectiveness of the dye transfer inhibitor compositions was tested using a six position Terg-O-Tometer instrument. Each washing composition contained 10 ppm of dye, 1 g/1 Wisk laundry detergent and a given amount of dye transfer inhibitor additive. These components were diluted with synthetic hard water (110 ppm Ca:Mg 3:1) to a volume of one liter. Two undyed cotton swatches (Scientific Services SID, Inc.) were immersed in the test solutions. The solutions were agitated for ten minutes. The swatches were then removed, excess solution drained from the Terg-O-Tometer and the swatches rinsed in clean hard water for three minutes.
- the swatches were then air dried for at least one hour. Reflectance measurements were taken on a Hunter Lab Color Quest colorimeter. The reflectance readings were recorded as ⁇ E, which is a composite of the degree of whiteness, redness and blueness indices in the dyed cloth. These readings were taken as a direct measure of the degree of dye deposition under the test washing condition.
- the test parameter percent inhibition was calculated using the "a" value from the ⁇ E equation where "a" is a measure of the redness and greenness of the sample being measured. To calculate percent inhibition use the following equation:
- Typical treat levels of dye transfer inhibitor in laundry detergent are between l-30ppm.
- the 4-vinylpyridine / AMPS salt was characterized by NMR and was very effective at dye transfer inhibition, particularly at low levels (5-10ppm), when compared to the commercial materials at the same concentration.
- reaction products of 4-vinylpyridine and AMPS contain adduct structure shown previously and 4-vinylpyridine self -polymerized and oligomerized species.
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Abstract
Description
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AU2003298918A AU2003298918A1 (en) | 2002-11-26 | 2003-11-25 | Dye transfer inhibitors for laundry detergents |
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US42947902P | 2002-11-26 | 2002-11-26 | |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023041739A1 (en) * | 2021-09-16 | 2023-03-23 | Reckitt Benckiser Vanish B.V. | Laundry composition for the removal of stains |
WO2023131463A1 (en) * | 2022-01-06 | 2023-07-13 | Henkel Ag & Co. Kgaa | Color-protecting detergents |
WO2023131528A1 (en) * | 2022-01-06 | 2023-07-13 | Henkel Ag & Co. Kgaa | Color-protecting detergents |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5458809A (en) * | 1992-07-15 | 1995-10-17 | The Procter & Gamble Co. | Surfactant-containing dye transfer inhibiting compositions |
US6191098B1 (en) * | 1999-04-28 | 2001-02-20 | National Starch And Chemical Investment Holding Corporation | Polyvinylpyridinium derivatives as anti-dye transfer agents |
US6306815B1 (en) * | 1999-09-10 | 2001-10-23 | National Starch And Chemical Investment Holding Corporation | Quaternary polyvinylpyrridinium derivatives as anti-dye transfer agents |
-
2003
- 2003-11-25 AU AU2003298918A patent/AU2003298918A1/en not_active Abandoned
- 2003-11-25 WO PCT/US2003/038680 patent/WO2004048506A1/en not_active Application Discontinuation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5458809A (en) * | 1992-07-15 | 1995-10-17 | The Procter & Gamble Co. | Surfactant-containing dye transfer inhibiting compositions |
US6191098B1 (en) * | 1999-04-28 | 2001-02-20 | National Starch And Chemical Investment Holding Corporation | Polyvinylpyridinium derivatives as anti-dye transfer agents |
US6306815B1 (en) * | 1999-09-10 | 2001-10-23 | National Starch And Chemical Investment Holding Corporation | Quaternary polyvinylpyrridinium derivatives as anti-dye transfer agents |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023041739A1 (en) * | 2021-09-16 | 2023-03-23 | Reckitt Benckiser Vanish B.V. | Laundry composition for the removal of stains |
WO2023131463A1 (en) * | 2022-01-06 | 2023-07-13 | Henkel Ag & Co. Kgaa | Color-protecting detergents |
WO2023131528A1 (en) * | 2022-01-06 | 2023-07-13 | Henkel Ag & Co. Kgaa | Color-protecting detergents |
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