EP0285037A2 - Utilisation de polymères greffés à base d'oxydes de polyalkylènes comme agents antirédéposants pendant le lavage et le post-traitement de matières textiles contenant des fibres synthétiques - Google Patents
Utilisation de polymères greffés à base d'oxydes de polyalkylènes comme agents antirédéposants pendant le lavage et le post-traitement de matières textiles contenant des fibres synthétiques Download PDFInfo
- Publication number
- EP0285037A2 EP0285037A2 EP88104888A EP88104888A EP0285037A2 EP 0285037 A2 EP0285037 A2 EP 0285037A2 EP 88104888 A EP88104888 A EP 88104888A EP 88104888 A EP88104888 A EP 88104888A EP 0285037 A2 EP0285037 A2 EP 0285037A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- graft polymers
- oxide
- weight
- polyalkylene oxides
- number average
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 31
- 229920000233 poly(alkylene oxides) Polymers 0.000 title claims abstract description 26
- 229920002994 synthetic fiber Polymers 0.000 title claims abstract description 9
- 239000004753 textile Substances 0.000 title claims abstract description 9
- 238000005406 washing Methods 0.000 title claims description 13
- 239000003599 detergent Substances 0.000 claims abstract description 38
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003112 inhibitor Substances 0.000 claims abstract description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000012209 synthetic fiber Substances 0.000 claims abstract description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims abstract description 5
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- 239000000463 material Substances 0.000 claims abstract description 4
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- 239000004094 surface-active agent Substances 0.000 claims description 8
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- 239000000654 additive Substances 0.000 claims description 3
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- 238000012360 testing method Methods 0.000 description 11
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
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- 229920000728 polyester Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010559 graft polymerization reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002979 fabric softener Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 2
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
-
- 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
- C11D3/3788—Graft polymers
Definitions
- the object of the present invention is to provide other graying inhibitors for detergents and graying inhibitors for the aftertreatment of textile goods containing synthetic fibers.
- the products to be used according to the invention are known for example from GB-PS 922 457.
- the graft base used is the polyalkylene oxides of molecular weight (number average) from 300 to 100,000 based on ethylene oxide, propylene oxide and / or butylene oxide which are capped at one end and capped at one end.
- Homopolymers of ethylene oxide or ethylene oxide copolymers with an ethylene oxide content of 40 to 99 mol%, which are end group-capped at least on one side, are preferably used.
- the proportion of ethylene oxide polymerized in is therefore 40 to 100 mol% for the ethylene oxide polymers to be used with preference.
- Suitable comonomers for these copolymers are propylene oxide, n-butylene oxide and / or isobutylene oxide.
- copolymers of ethylene oxide and propylene oxide, copolymers of ethylene oxide and butylene oxide, and copolymers of ethylene oxide, propylene oxide and at least one butylene oxide are suitable.
- the ethylene oxide content of the copolymers is preferably 40 to 99 mol%, the propylene oxide content 1 up to 60 mol% and the proportion of butylene oxide in the copolymers 1 to 30 mol%.
- branched homopolymers or copolymers which are end group-capped at least on one side can also be used as the graft base.
- Branched copolymers are prepared, for example, by adding to polyhydric low molecular weight alcohols, for example trimethylolpropane, glycerol, pentoses or hexoses, ethylene oxide and, if appropriate, also propylene oxide and / or butylene oxides.
- the alkylene oxide units can be randomly distributed in the polymer or in the form of blocks.
- At least one terminal OH group of the polyalkylene oxides is end group-capped. This should be understood to mean that it is etherified, esterified, aminated or modified by reaction with an isocyanate, for example.
- the substituents of the terminal H atoms of the hydroxyl groups of the polyalkylene oxides are alkyl groups with 1 to 18 carbon atoms, substituted alkyl groups, such as the benzyl group, or phenyl groups.
- Polyalkylene oxides whose end groups are esterified are obtained, for example, by esterification of the polyalkylene oxides described above with carboxylic acids having 1 to 18 carbon atoms, e.g. by reaction with formic acid, acetic acid, propionic acid, butyric acid, malonic acid, succinic acid, stearic acid, maleic acid, terephthalic acid and phthalic acid.
- the end group capping of the polyalkylene oxides can also be carried out by reaction with the corresponding anhydrides, e.g. by reaction with maleic anhydride.
- the polyalkylene oxides can also be reacted at least on one side by reaction with isocyanants, e.g. Phenyl isocyanate, naphthyl isocyanate, methyl, ethyl and stearyl isocyanate can be modified.
- Aminated products are obtained by autoclaving the corresponding alkylene oxide with amines, e.g. C1 to C18 alkylamines obtained.
- vinyl esters are used which are derived from a saturated monocarboxylic acid containing 1 to 6 carbon atoms, as well as methyl acrylate, ethyl acrylate, methyl methacrylate, methyl methacrylate and mixtures of the above-mentioned monomers.
- Suitable vinyl esters are, for example, vinyl formate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, vinyl i-valerate and vinyl caproate.
- the graft copolymers are prepared by known processes, for example by the polyalkylene oxides of component (a) at least one end group capped with the monomers of component (b) in the presence of free radical initiators or by action grafting high-energy radiation, which should also be understood to mean the action of high-energy electrons.
- the procedure here can be such that component (a) is dissolved in at least one monomer from group (b) and the mixture is polymerized out after addition of a polymerization initiator.
- the graft copolymerization can also be carried out semi-continuously by initially introducing a portion, for example 10%, of the mixture of end-capped polyalkylene oxide to be polymerized, at least one monomer from group (b) and initiator, heating to the polymerization temperature and, after the polymerization has started, the rest of the polymerizing mixture is added according to the progress of the polymerization.
- the graft copolymers can also be obtained by placing the end-capped polyalkylene oxides of group (a) in a reactor, heating to the polymerization temperature and adding and polymerizing at least one monomer of group (b) and polymerization initiator either all at once, batchwise or, preferably, continuously.
- the weight ratio of components (a) :( b) is 1: 0.2 to 1:10, preferably 1: 0.5 to 1: 6.
- Suitable polymerization initiators are, in particular, organic peroxides, such as diacetyl peroxide, dibenzoyl peroxide, succinyl peroxide, di-tertiary butyl peroxide, tertiary butyl perbenzoate, tertiary butyl perpivalate, tertiary butyl permaleinate, cumene hydroperoxide, diamopropyl peroxide, diarbamate toloyl peroxide, Dioctanoyl peroxide, dilauroyl peroxide, tertiary butyl perisobutyrate, tertiary butyl peracetate, di-tertiary amyl peroxide, tertiary butyl hydroperoxide and mixtures of the initiators, redox initiators and azo starters mentioned.
- organic peroxides such as diacetyl peroxide, dibenzoyl peroxide, succinyl peroxid
- the graft polymerization takes place in the temperature range from 50 to 200, preferably 70 to 140 ° C. It is usually carried out under atmospheric pressure, but can also take place under reduced or elevated pressure. If desired, the graft copolymerization described above can also be carried out in a solvent.
- Suitable solvents are, for example, alcohols, for example methanol, ethanol, n-propanol, isopropanol, n-butanol, secondary butanol, tertiary butanol, n-hexanol and cyclohexanol, and glycols, such as ethylene glycol, propylene glycol and butylene glycol, and the methyl or ethyl ether dihydric alcohols, diethylene glycol, triethylene glycol, glycerin and dioxane.
- the graft polymerization can also be carried out in water as a solvent.
- a solution which, depending on the amount of the monomers of component (b) added, is more or less readily soluble in water and can assume a disperse character.
- organic solvents can be added, for example zen, for example monohydric alcohols with 1 to 3 carbon atoms, acetone or dimethylformamide.
- graft polymerization in water can also be carried out by converting the water-insoluble graft polymers into a finely divided dispersion by adding customary emulsifiers or protective colloids, for example polyvinyl alcohol.
- the emulsifiers used are, for example, ionic or nonionic surfactants whose HLB value is in the range from 3 to 13.
- HLB value For the definition of the HLB value, reference is made to the publication by WC Griffin, J. Suc. Cosmetic Chem., Vol. 5, 249 (1954).
- the amount of surfactants, based on the graft polymer is 0.1 to 5% by weight.
- water When water is used as the solvent, solutions or dispersions of the graft polymers are obtained. If solutions of the graft polymer are prepared in an organic solvent or in mixtures of an organic solvent and water, 5 to 200, preferably 10 to 100 parts by weight of the organic solvent or solvent mixture are used per 100 parts by weight of the graft polymer.
- the graft polymers have a K value of 5 to 200, preferably 5 to 50 (determined according to H. Fikentscher in dimethylformamide at 25 ° C. and a polymer concentration of 2% by weight).
- the graft polymer can optionally be subjected to a partial hydrolysis, in which up to 15 mol% of the grafted monomers of component (b) are hydrolyzed.
- a partial hydrolysis in which up to 15 mol% of the grafted monomers of component (b) are hydrolyzed.
- the hydrolysis of graft polymers for the preparation of which vinyl acetate was used as the preferred monomer of group (b), becomes graft polymers containing vinyl alcohol units.
- the hydrolysis can be carried out, for example, by adding a base, such as sodium hydroxide solution, potassium hydroxide solution, ammonia or amines, such as triethanolamine, morpholine or triethylamine, or by adding acids, e.g. HCl, and optionally heating the mixture.
- a base such as sodium hydroxide solution, potassium hydroxide solution, ammonia or amines, such as triethanolamine, morpholine or triethylamine
- acids e.g. HCl
- the graft polymers described above are used in detergents with a reduced phosphate content (this is to be understood as meaning a phosphate content of less than 25% by weight sodium triphosphate) or in phosphate-free detergents.
- the graft polymers described above are added to commercial detergent formulations in an amount of 0.1 to 5, preferably 0.3 to 3,% by weight, based on the detergent mixture.
- the graft polymers can be added to the detergent formulation in the form of granules, a paste, a highly viscous mass, as a dispersion or as a solution in a solvent.
- the graft polymers can also be adsorbed on the surface of fillers, for example sodium sulfate or builders (zeolites) and other solid auxiliaries in the detergent formulation.
- phosphate content is below 25% by weight or detergents which are free of phosphate at all contain surfactants as an essential component, e.g. C8 to C12 alkylphenol ethoxylates, C12 to C20 alkanol ethoxylates, and block copolymers of ethylene oxide and propylene oxide.
- the polyalkylene oxides are solids at room temperature up to temperatures of 70 ° C. and are readily soluble or dispersible in water. These are linear or branched reaction products of ethylene oxide with propylene oxide and / or isobutylene oxide, which have a block structure or which can also have a statistical structure.
- the end groups of the polyalkylene oxides can optionally be closed. This should be understood to mean that the free OH groups of the polyalkylene oxides can be etherified and / or esterified and / or aminated and / or reacted with isocyanates.
- Anionic surfactants such as C8 to C12 alkyl benzene sulfonates, C12 to C16 alkane sulfonates, C12 to C16 alkyl sulfates, C12 to C16 alkyl sulfosuccinates and sulfated ethoxylated C12 to C16 alkanols are also suitable as constituents of powder detergents.
- Powdery detergents usually contain 5 to 20% by weight of a surfactant or a mixture of surfactants.
- the surfactant content of liquid detergents is in the range from 15 to 50% by weight.
- the powder detergents can optionally also contain polycarboxylic acids or their salts, for example tartaric acid and citric acid.
- incrustation inhibitors are, for example, homopolymers of acrylic acid, methacrylic acid and maleic acid or copolymers, e.g. Copolymers of maleic acid and acrylic acid, copolymers of maleic acid and methacrylic acid or copolymers of a) acrylic acid and / or methacrylic acid with b) acrylic acid esters, methacrylic acid esters, vinyl esters, allyl esters, itaconic acid esters, itaconic acid, methylene malonic acid, methylene malonic acid esters, crotonic acid and crotonic acid esters.
- homopolymers of acrylic acid, methacrylic acid and maleic acid or copolymers e.g. Copolymers of maleic acid and acrylic acid, copolymers of maleic acid and methacrylic acid or copolymers of a) acrylic acid and / or methacrylic acid with b) acrylic acid esters, methacrylic acid esters, vinyl esters, allyl
- copolymers of olefins and C1 to C4 alkyl vinyl ethers come into consideration.
- the molecular weight of the homopolymers and copolymers is 1,000 to 100,000.
- the incrustation inhibitors are used in an amount of 0.5 to 10% by weight in detergents, whereby they are in non-neutralized form, as alkali or ammonium salt as well as in partially neutralized form, e.g. Neutralization of 40 to 60% of the carboxyl groups can be used.
- Powdered detergents may also contain zeolites, for example in an amount of 5 to 30% by weight.
- the detergent formulations can optionally also contain bleaches. If bleaching agents are used, the amounts usually used are 3 to 25% by weight.
- Sodium perborate for example, is suitable as a bleaching agent.
- the detergent formulations may also contain bleach activators, plasticizers, defoamers, perfumes, optical brighteners and enzymes.
- Detergents, such as sodium sulfate, can optionally be present in an amount of 10 to 30% by weight.
- the graft polymers described above can also be used as an additive to liquid detergents.
- the liquid detergents contain, as a mixing component, liquid or solid surfactants which are soluble or at least dispersible in the detergent formulation. Suitable surfactants for this are the products which are also used in powder detergents, and liquid polyalkylene oxides or polyalkoxylated compounds.
- a small amount of solubilizers e.g. Water or a water-miscible organic solvent, e.g. Prepare a homogeneous mixture of isopropanol, methanol, ethanol, glycol, diethylene glycol or triethylene glycol.
- the graft polymers are also suitable as an additive in the aftertreatment of textile material containing synthetic fibers.
- they are added to the last rinsing bath of a washing machine cycle, the addition either being carried out together with a fabric softener normally used at this point or — if a fabric softener is not desired — alone instead of the fabric softener.
- the amounts used are 0.01 to 0.3 g / l wash liquor.
- the use of the graft polymers in the last rinsing bath of a washing machine cycle has the advantage that the laundry is soiled less by detached dirt particles that are present in the washing liquor during the next washing cycle than without the addition of the graying inhibitor in the previous washing.
- the parts given in the examples are parts by weight, the figures in percent relate to the weight of the substances.
- the molecular weights (number average) of the polyalkylene oxides a) used were calculated from the OH number.
- the graft polymers were prepared by the process known from GB-PS 922 457 by grafting on the monomers (b) given in Table 1 (to 100 parts in each case of a polyalkylene oxide with the molecular weight (number average) also given in Table 1).
- the polymers 1, 3 to 10 and 18 to 20 were etherified, in the case of the polymers 2, 11 and 12 a terminal OH group of the polyalkylene oxide was esterified, in the case of polymer 15 a terminal OH group was aminated with a C10-amine, in which Polymers 16 and 17 were both both terminal OH groups of the polyalkylene oxide esterified with maleic acid and in polymer 19 one end group of the polyalkylene oxide was etherified with a C10-alkyl group while the other was esterified with maleic acid.
- the graying-inhibiting effect of the above-mentioned graft polymers was tested as follows: polyester test fabric and polyester / cotton blend fabric were subjected to a series of 3 washes together with a standard dirt fabric. The dirty fabric is renewed after each wash, the test fabric becoming more soiled after each wash. The whiteness of the test fabric after the 3rd wash is used to assess the degree of soiling. The values are secured by repeated repetition and averaging. The photometric measurement of the reflectance in% was measured in the present case on the Elrepho 2000 (Datacolor) at the wavelength 460 nm (barium primary white standard according to DIN 5033.
- the graying inhibitor was added in each case in an amount of 0.5%, based on the test detergent.
- the test vessels each contained 15 g of test fabric (5 g polyester, 5 g polyester-cotton blend and 5 g cotton fabric) and 10 g dirt fabric. Cotton dirt from the Krefeld laundry research institute was used as the dirt fabric, namely WFK 10D.
- the test detergent used had the following composition: C12 alkyl benzene sulfonate 6.25% Tallow fatty alcohol reacted with 11% 4.7% ethylene oxide Soap 2.8% Na triphosphate (90% degree of conservation) 20% Na perborate (tetrahydrate) 20% Na2SO4 24% Sodium disilicate 6% Mg silicate 1.25% Carboxymethyl cellulose (CMC), Na salt 0.6% Tetrasodium salt of ethylenediaminetetraacetic acid 0.2% Rest of water to 100%.
- CMC Carboxymethyl cellulose
- Table 2 shows the increase in reflectance of polyester and polyester / cotton blended fabrics after addition of 0.5% of the products to be used according to the invention, based on the weight of the test detergent used. Table 2 also shows the results of comparative examples.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Graft Or Block Polymers (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT88104888T ATE91499T1 (de) | 1987-04-03 | 1988-03-26 | Verwendung von propfpolymerisaten auf basis von polyalkylenoxiden als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3711298 | 1987-04-03 | ||
DE19873711298 DE3711298A1 (de) | 1987-04-03 | 1987-04-03 | Verwendung von propfpolymerisaten auf basis von polyalkylenoxiden als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0285037A2 true EP0285037A2 (fr) | 1988-10-05 |
EP0285037A3 EP0285037A3 (en) | 1990-09-19 |
EP0285037B1 EP0285037B1 (fr) | 1993-07-14 |
Family
ID=6324811
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88104888A Expired - Lifetime EP0285037B1 (fr) | 1987-04-03 | 1988-03-26 | Utilisation de polymères greffés à base d'oxydes de polyalkylènes comme agents antirédéposants pendant le lavage et le post-traitement de matières textiles contenant des fibres synthétiques |
Country Status (7)
Country | Link |
---|---|
US (1) | US4846995A (fr) |
EP (1) | EP0285037B1 (fr) |
JP (1) | JP2541616B2 (fr) |
AT (1) | ATE91499T1 (fr) |
CA (1) | CA1302832C (fr) |
DE (2) | DE3711298A1 (fr) |
ES (1) | ES2041721T3 (fr) |
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US4846994A (en) * | 1987-04-03 | 1989-07-11 | Basf Aktiengesellschaft | Use of graft polymers based on polyalkylene oxides as grayness inhibitors in the wash and aftertreatment of textile material containing synthetic fibers |
EP0429307A2 (fr) * | 1989-11-22 | 1991-05-29 | Rohm And Haas Company | Copolymères greffés solubles dans l'eau biodégradables, compositions contenant de tels copolymères et méthodes d'utilisation de tels copolymères |
WO1991019778A1 (fr) * | 1990-06-19 | 1991-12-26 | Basf Aktiengesellschaft | Utilisation de copolymeres greffes dans des produits de lavage et de nettoyage |
US6946004B2 (en) | 2000-08-30 | 2005-09-20 | Basf Aktiengesellschaft | Use of grafted polyalkylene oxides as greying inhibitors when washing |
WO2012079256A1 (fr) * | 2010-12-17 | 2012-06-21 | The Procter & Gamble Company | Compositions de nettoyage avec des polymères greffés de polycarboxylate - oxyde de polyalkylène à coiffe d'oxyde de polyoxyalkylène |
US8519060B2 (en) | 2006-05-31 | 2013-08-27 | Basf Se | Amphiphilic graft polymers based on polyalkylene oxides and vinyl esters |
WO2013132042A1 (fr) | 2012-03-09 | 2013-09-12 | Basf Se | Procédé continu de synthèse de polymères greffés basé sur des polyéthers |
US9068023B2 (en) | 2012-03-09 | 2015-06-30 | Basf Se | Continuous process for the synthesis of graft polymers based on polyethers |
EP2980198A1 (fr) * | 2014-07-31 | 2016-02-03 | The Procter and Gamble Company | Composition comprenant un polymère greffé amphiphile |
EP4134420A1 (fr) * | 2021-08-12 | 2023-02-15 | The Procter & Gamble Company | Composition détergente comprenant un tensioactif détergent et des polymères greffés biodégradables |
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US5750483A (en) * | 1995-12-06 | 1998-05-12 | Basf Corporation | Non-phosphate machine dishwashing compositions containing polycarboxylate polymers and nonionic graft copolymers of vinyl acetate and polyalkylene oxide |
JP3264837B2 (ja) * | 1996-08-23 | 2002-03-11 | 花王株式会社 | 濃厚系液体洗浄剤組成物 |
US5922663A (en) | 1996-10-04 | 1999-07-13 | Rhodia Inc. | Enhancement of soil release with gemini surfactants |
JP3983398B2 (ja) * | 1998-12-09 | 2007-09-26 | 花王株式会社 | 洗浄性向上剤 |
EP1629073B1 (fr) * | 2003-06-11 | 2008-11-12 | Ciba Specialty Chemicals Water Treatments Limited | Agent de surface polymere |
ATE502998T1 (de) * | 2006-07-07 | 2011-04-15 | Procter & Gamble | Waschmittelzusammensetzungen |
KR101358926B1 (ko) * | 2007-01-31 | 2014-02-06 | 주식회사 엘지생활건강 | 반응성 물질을 함유하는 섬유용 세제 및 유연제 조성물 |
CA2694212C (fr) * | 2007-08-03 | 2016-04-12 | Reinhold Leyrer | Dispersion d'epaississant associatif |
NZ584345A (en) * | 2007-11-14 | 2012-05-25 | Basf Se | Method for producing a thickener dispersion |
EP2083067A1 (fr) | 2008-01-25 | 2009-07-29 | Basf Aktiengesellschaft | Utilisation de complexants organiques et/ou de liaisons contenant des groupes d'acides de carbone polymères dans une composition de produit de lavage ou de nettoyage |
JP2010059243A (ja) * | 2008-09-01 | 2010-03-18 | Nippon Shokubai Co Ltd | 重合体組成物およびその製造方法 |
TW201031743A (en) | 2008-12-18 | 2010-09-01 | Basf Se | Surfactant mixture comprising branched short-chain and branched long-chain components |
WO2011003904A1 (fr) | 2009-07-10 | 2011-01-13 | Basf Se | Mélange de tensioactifs contenant des constituants à chaîne courte et à chaîne longue |
EP2534234B1 (fr) | 2010-02-12 | 2015-01-14 | Basf Se | Utilisation d'un copolymère comme épaississant dans les lessives liquides à tendance au grisage réduite |
WO2011157777A1 (fr) | 2010-06-17 | 2011-12-22 | Basf Se | Polymères à groupes latéraux saccharide et leurs applications |
JP2015518059A (ja) | 2012-03-09 | 2015-06-25 | ザ プロクター アンド ギャンブルカンパニー | 広い極性分布を有するグラフトポリマーを含む洗剤組成物 |
EP2980197A1 (fr) * | 2014-07-31 | 2016-02-03 | The Procter and Gamble Company | Composition détergente liquide pour le lavage |
US11326129B2 (en) | 2018-06-26 | 2022-05-10 | The Procter & Gamble Company | Fabric care compositions that include a graft copolymer and related methods |
EP4446302A1 (fr) | 2023-04-12 | 2024-10-16 | Basf Se | Acétate de vinyle synthétique ayant une faible teneur en deutérium à partir de ressources non-fosil |
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GB922457A (en) * | 1958-04-15 | 1963-04-03 | Hoechst Ag | Graft copolymers and process for preparing them |
EP0098803A1 (fr) * | 1982-07-06 | 1984-01-18 | Ciba-Geigy Ag | Polymères greffés solubles ou dispersables dans l'eau, leur fabrication et utilisation |
EP0219048A2 (fr) * | 1985-10-12 | 1987-04-22 | BASF Aktiengesellschaft | Utilisation de copolymères greffés d'oxydes de polyalkylènes et d'acétate de vinyle comme agents antiredéposants pendant le lavage et le post-traitement de matières textiles contenant des fibres synthétiques |
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DE3206883A1 (de) * | 1982-02-26 | 1983-09-15 | Basf Ag, 6700 Ludwigshafen | Verwendung von copolymerisaten, die basische gruppen enthalten, als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
DE3426368A1 (de) * | 1984-07-18 | 1986-01-23 | Basf Ag, 6700 Ludwigshafen | Copolymerisate fuer wasch- und reinigungsmittel |
DE3711296A1 (de) * | 1987-04-03 | 1988-10-13 | Basf Ag | Verwendung von alkoxylierten, carboxylgruppen enthaltenden polymerisaten in waschmitteln |
DE3711319A1 (de) * | 1987-04-03 | 1988-10-20 | Basf Ag | Verwendung von pfropfpolymerisaten auf basis von polyalkylenoxiden als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
DE3711318A1 (de) * | 1987-04-03 | 1988-10-20 | Basf Ag | Verwendung von pfropfpolymerisaten auf basis von polyalkylenoxiden als vergrauungsinhibitoren beim waschen und nachbehandeln von synthesefasern enthaltendem textilgut |
DE3712069A1 (de) * | 1987-04-09 | 1988-10-20 | Basf Ag | Verwendung von pfropfpolymerisaten auf basis von polyestern, polyesterurethanen und polyesteramiden als vergrauungsinhibitoren in waschmitteln |
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- 1987-04-03 DE DE19873711298 patent/DE3711298A1/de not_active Withdrawn
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1988
- 1988-03-25 CA CA000562575A patent/CA1302832C/fr not_active Expired - Lifetime
- 1988-03-26 DE DE8888104888T patent/DE3882260D1/de not_active Expired - Lifetime
- 1988-03-26 EP EP88104888A patent/EP0285037B1/fr not_active Expired - Lifetime
- 1988-03-26 ES ES198888104888T patent/ES2041721T3/es not_active Expired - Lifetime
- 1988-03-26 AT AT88104888T patent/ATE91499T1/de active
- 1988-03-29 JP JP63073482A patent/JP2541616B2/ja not_active Expired - Fee Related
- 1988-03-31 US US07/175,190 patent/US4846995A/en not_active Expired - Lifetime
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GB922457A (en) * | 1958-04-15 | 1963-04-03 | Hoechst Ag | Graft copolymers and process for preparing them |
EP0098803A1 (fr) * | 1982-07-06 | 1984-01-18 | Ciba-Geigy Ag | Polymères greffés solubles ou dispersables dans l'eau, leur fabrication et utilisation |
EP0219048A2 (fr) * | 1985-10-12 | 1987-04-22 | BASF Aktiengesellschaft | Utilisation de copolymères greffés d'oxydes de polyalkylènes et d'acétate de vinyle comme agents antiredéposants pendant le lavage et le post-traitement de matières textiles contenant des fibres synthétiques |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4846994A (en) * | 1987-04-03 | 1989-07-11 | Basf Aktiengesellschaft | Use of graft polymers based on polyalkylene oxides as grayness inhibitors in the wash and aftertreatment of textile material containing synthetic fibers |
EP0429307A2 (fr) * | 1989-11-22 | 1991-05-29 | Rohm And Haas Company | Copolymères greffés solubles dans l'eau biodégradables, compositions contenant de tels copolymères et méthodes d'utilisation de tels copolymères |
EP0429307A3 (en) * | 1989-11-22 | 1992-03-25 | Rohm And Haas Company | Biodegradable, water-soluble graft copolymers, compositions containing such copolymers, and methods of use of such copolymers |
TR26387A (tr) * | 1989-11-22 | 1995-03-15 | Rohm & Haas | BIYO-BOZUNUR SUDA CÖZüNüR ASI KOPOLIMERLERI, BU GIBI KOPOLIMERLERI IHTIVA EDEN BILESIMLER VE BU KOPOLIMERLERIN KULLANIM YÖNTEMLERI |
WO1991019778A1 (fr) * | 1990-06-19 | 1991-12-26 | Basf Aktiengesellschaft | Utilisation de copolymeres greffes dans des produits de lavage et de nettoyage |
US6946004B2 (en) | 2000-08-30 | 2005-09-20 | Basf Aktiengesellschaft | Use of grafted polyalkylene oxides as greying inhibitors when washing |
US8519060B2 (en) | 2006-05-31 | 2013-08-27 | Basf Se | Amphiphilic graft polymers based on polyalkylene oxides and vinyl esters |
WO2012079256A1 (fr) * | 2010-12-17 | 2012-06-21 | The Procter & Gamble Company | Compositions de nettoyage avec des polymères greffés de polycarboxylate - oxyde de polyalkylène à coiffe d'oxyde de polyoxyalkylène |
WO2013132042A1 (fr) | 2012-03-09 | 2013-09-12 | Basf Se | Procédé continu de synthèse de polymères greffés basé sur des polyéthers |
EP2862884A1 (fr) | 2012-03-09 | 2015-04-22 | Basf Se | Procédé continu pour la synthèse de polymères greffés à base de polyéthers |
EP2865692A1 (fr) | 2012-03-09 | 2015-04-29 | Basf Se | Procédé continu pour la synthèse de polymères greffés à base de polyéthers |
EP2886567A1 (fr) | 2012-03-09 | 2015-06-24 | Basf Se | Procédé continu pour la synthèse de polymères greffés à base de polyéthers |
US9068023B2 (en) | 2012-03-09 | 2015-06-30 | Basf Se | Continuous process for the synthesis of graft polymers based on polyethers |
EP2980198A1 (fr) * | 2014-07-31 | 2016-02-03 | The Procter and Gamble Company | Composition comprenant un polymère greffé amphiphile |
EP4134420A1 (fr) * | 2021-08-12 | 2023-02-15 | The Procter & Gamble Company | Composition détergente comprenant un tensioactif détergent et des polymères greffés biodégradables |
EP4134421A1 (fr) * | 2021-08-12 | 2023-02-15 | The Procter & Gamble Company | Composition détergente comprenant un tensioactif détergent et un polymère greffé |
WO2023019152A1 (fr) * | 2021-08-12 | 2023-02-16 | The Procter & Gamble Company | Composition détergente comprenant un tensioactif détersif et des polymères greffés biodégradables |
WO2023019153A1 (fr) * | 2021-08-12 | 2023-02-16 | The Procter & Gamble Company | Composition détergente comprenant un tensioactif détersif et un polymère greffé |
Also Published As
Publication number | Publication date |
---|---|
JP2541616B2 (ja) | 1996-10-09 |
CA1302832C (fr) | 1992-06-09 |
DE3711298A1 (de) | 1988-10-13 |
EP0285037B1 (fr) | 1993-07-14 |
EP0285037A3 (en) | 1990-09-19 |
US4846995A (en) | 1989-07-11 |
DE3882260D1 (de) | 1993-08-19 |
ATE91499T1 (de) | 1993-07-15 |
ES2041721T3 (es) | 1993-12-01 |
JPS63260994A (ja) | 1988-10-27 |
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