CN1882623B - 包含聚氧化烯基团和季氮原子的共聚物 - Google Patents
包含聚氧化烯基团和季氮原子的共聚物 Download PDFInfo
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- CN1882623B CN1882623B CN2004800343326A CN200480034332A CN1882623B CN 1882623 B CN1882623 B CN 1882623B CN 2004800343326 A CN2004800343326 A CN 2004800343326A CN 200480034332 A CN200480034332 A CN 200480034332A CN 1882623 B CN1882623 B CN 1882623B
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- methyl
- monomer
- alkyl
- multipolymer
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- 229920000233 poly(alkylene oxides) Polymers 0.000 title claims abstract description 9
- 229920001577 copolymer Polymers 0.000 title abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims abstract description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000000129 anionic group Chemical group 0.000 claims abstract description 10
- 239000002734 clay mineral Substances 0.000 claims abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
- -1 ethylidene, propylidene Chemical group 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 28
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 5
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims description 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000003999 initiator Substances 0.000 description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004744 fabric Substances 0.000 description 12
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000001294 propane Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 9
- 229950007687 macrogol ester Drugs 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000005660 chlorination reaction Methods 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SNEBFJPGYXTAMX-UHFFFAOYSA-N S(=O)(=O)(OC)O.C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound S(=O)(=O)(OC)O.C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O SNEBFJPGYXTAMX-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- QNIRRHUUOQAEPB-UHFFFAOYSA-N 2-(prop-2-enoylamino)butane-2-sulfonic acid Chemical compound CCC(C)(S(O)(=O)=O)NC(=O)C=C QNIRRHUUOQAEPB-UHFFFAOYSA-N 0.000 description 2
- DMSRIHVZKOZKRV-UHFFFAOYSA-N 2-methyl-1-(2-methylprop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C(C)=C DMSRIHVZKOZKRV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-L ethenyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-L 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- FWFUWXVFYKCSQA-UHFFFAOYSA-M sodium;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C FWFUWXVFYKCSQA-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- JSYPRLVDJYQMAI-ODZAUARKSA-N (z)-but-2-enedioic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)\C=C/C(O)=O JSYPRLVDJYQMAI-ODZAUARKSA-N 0.000 description 1
- ZLPXFBBKYQYQEA-UHFFFAOYSA-N 1-(prop-2-enoylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(=O)C=C ZLPXFBBKYQYQEA-UHFFFAOYSA-N 0.000 description 1
- IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- UVQPDGXQIPNYNU-UHFFFAOYSA-N 1-ethenyl-3-ethyl-2h-imidazole Chemical compound CCN1CN(C=C)C=C1 UVQPDGXQIPNYNU-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- MVYVKSBVZFBBPL-UHFFFAOYSA-N 2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CC(C)NC(=O)C=C MVYVKSBVZFBBPL-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- 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 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- KEDHVYZRMXPBMP-UHFFFAOYSA-N 2-methyl-1-oxoprop-2-ene-1-sulfonic acid Chemical compound CC(=C)C(=O)S(O)(=O)=O KEDHVYZRMXPBMP-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- XERGTCWVYOKNAV-UHFFFAOYSA-N 2-methylpentane-1,2-diol Chemical compound CCCC(C)(O)CO XERGTCWVYOKNAV-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
- QXIQCNFSNJEMOD-UHFFFAOYSA-N 3-hydroxybutan-2-yl prop-2-enoate Chemical compound CC(O)C(C)OC(=O)C=C QXIQCNFSNJEMOD-UHFFFAOYSA-N 0.000 description 1
- CAMBAGZYTIDFBK-UHFFFAOYSA-N 3-tert-butylperoxy-2-methylpropan-1-ol Chemical compound CC(CO)COOC(C)(C)C CAMBAGZYTIDFBK-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
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- BNBOGOLZFVOCSC-UHFFFAOYSA-N N-methylprop-2-enehydrazide Chemical compound CN(N)C(=O)C=C BNBOGOLZFVOCSC-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000001792 White test Methods 0.000 description 1
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- IOMDIVZAGXCCAC-UHFFFAOYSA-M diethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](CC)(CC)CC=C IOMDIVZAGXCCAC-UHFFFAOYSA-M 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- UBTITNUVKXQFBF-UHFFFAOYSA-N ethanesulfonic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CCS(O)(=O)=O UBTITNUVKXQFBF-UHFFFAOYSA-N 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical group CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 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
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- LLBAPKIIGXPQIC-UHFFFAOYSA-N methanesulfonic acid;prop-2-enoic acid Chemical compound CS(O)(=O)=O.OC(=O)C=C LLBAPKIIGXPQIC-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 229940100573 methylpropanediol Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZOTWHNWBICCBPC-UHFFFAOYSA-N n-ethyl-n-methylprop-2-enamide Chemical compound CCN(C)C(=O)C=C ZOTWHNWBICCBPC-UHFFFAOYSA-N 0.000 description 1
- MUXRMEAOYBFTGZ-UHFFFAOYSA-N n-methyl-n-undecylprop-2-enamide Chemical compound CCCCCCCCCCCN(C)C(=O)C=C MUXRMEAOYBFTGZ-UHFFFAOYSA-N 0.000 description 1
- YUIVHZARNDKOHO-UHFFFAOYSA-N n-tert-butyl-n-methylprop-2-enamide Chemical compound CC(C)(C)N(C)C(=O)C=C YUIVHZARNDKOHO-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- BWJNKHVUFMTHNX-UHFFFAOYSA-N octan-3-yl but-2-enoate Chemical compound CCCCCC(CC)OC(=O)C=CC BWJNKHVUFMTHNX-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 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
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000000825 pharmaceutical preparation 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
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UOUAODFZKFGFKS-UHFFFAOYSA-N propane-1-sulfonic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCS(O)(=O)=O UOUAODFZKFGFKS-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
- C11D3/3776—Heterocyclic compounds, e.g. lactam
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
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Abstract
本发明涉及一种共聚物，其以共聚形式包含：(A)60-99重量％的至少一种式(I)的单烯键不饱和聚氧化烯单体，其中：当Y是-O-时，X是-CH2-或-CO-；当Y是-NH-时，X是-CO-；Y是-O-或-NH-；R1是氢或甲基；R2是相同或不同的C2-C6-亚烷基，其可以是直链或支化的和可以以嵌段或无规形式分布；R3是氢或C1-C4-烷基；n是3-50的整数；(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体；(C)0-39重量％的阴离子性单烯键不饱和单体；和(D)0-30重量％的其它非离子性单烯键不饱和单体，并且所述共聚物具有2000-100000的平均分子量Mw。本发明还涉及这些共聚物用作用于粘土矿物的分散剂的用途。
Description
本发明涉及新型共聚物，其以共聚形式包含
(A)60-99重量％的至少一种式I的单烯键不饱和聚氧化烯单体
其中的变量具有下述意义：
当Y是-O-时，X是-CH2-或-CO-；
当Y是-NH-时，X是-CO-；
Y是-O-或-NH-；
R1是氢或甲基；
R2是相同或不同的C2-C6-亚烷基，其可以是直链或支化的，和可以以嵌段或无规形式分布；
R3是氢或C1-C4-烷基；
n是3-50的整数，
(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体，
(C)0-39重量％的阴离子性单烯键不饱和单体，和
(D)0-30重量％的其它非离子性单烯键不饱和单体
并且具有2000-100000的平均分子量Mw。
另外，本发明涉及这些共聚物用作用于粘土矿物的分散剂的用途。
在洗涤方法中，一次去污力与二次去污力之间存在区别。一次去污力被理解为代表将污垢实际从纺织制品除去。二次去污力被理解为代表防止由于被脱离的污垢从洗液再沉积到织物所产生的影响。在反复洗涤操作中织物明显变灰，而且这种隐伏的变灰过程几乎不能逆转。为了防止棉质织物逐渐变灰，经常向洗涤剂中加入羧甲基纤维素(CMC)的钠盐。聚丙烯酸和丙烯酸-马来酸共聚物也具有抑制变灰的作用。但是，所述聚合物对于含粘土的污垢的作用不能令人满意。
WO-A-93/22358描述了用于化妆品制剂的稠化剂和分散剂，它们是基于至少50重量％的阴离子单体(如丙烯酸)和最高50重量％的烯键不饱和季铵化合物的共聚物。所述共聚物可以包含(甲基)丙烯酸酯作为其它单体，其中与氧化烯烃反应的醇的(甲基)丙烯酸酯也被规定为可能的共聚单体。但是，仅明确公开了包含甲基丙烯酸硬脂基酯作为共聚单体的共聚物，而且其仅以最多2.4重量％的量存在。
WO-00/39176公开了阴离子、阳离子和非离子性单体的共聚物作为用于化妆品和药物制剂的增稠剂或流变改进剂的用途。虽然烷氧基化醇的(甲基)丙烯酸酯被列为可能的非离子性共聚单体，但是已经指出，它们必须少量存在，否则共聚物的玻璃化转变温度会降低。
另外，WO-01/05874描述了适合用于从织物除去含粘土的污垢的两性多胺，它们通过多胺的烷氧基化反应和随后的季铵化和硫酸盐化作用获得。
最后，DE-A-100 62 355公开了用于表面处理的阴离子、阳离子和不溶于水的非离子性单体的共聚物。相应地，所述非离子性单体不具有氧化烯嵌段，而且它们在共聚物中的比例最多为16重量％。
本发明的目的是提供洗衣用洗涤剂的高分子添加剂，其以整体有利的应用性能为特征，尤其是具有改进的一次和二次去污力并且可容易且稳定地混入固体和液体洗衣用洗涤剂中。
我们发现，通过下述共聚物能够实现上述目的，所述共聚物以共聚形式包含：
(A)60-99重量％的至少一种式I的单烯键不饱和聚氧化烯单体
其中的变量具有下述意义：
当Y是-O-时，X是-CH2-或-CO-；
当Y是-NH-时，X是-CO-；
Y是-O-或-NH-；
R1是氢或甲基；
R2是相同或不同的C2-C6-亚烷基，其可以是直链或支化的，并且可以以嵌段或无规形式分布；
R3是氢或C1-C4-烷基；
n是3-50的整数，
(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体，
(C)0-39重量％的阴离子性单烯键不饱和单体，和
(D)0-30重量％的其它非离子性单烯键不饱和单体，
并且具有2000-100 000的平均分子量Mw。
优选的本发明共聚物包含其中变量具有下述意义的式I单烯键不饱和聚氧化烯单体作为共聚单体(A)：
X 是-CO-或-CH2-；
Y是-O-；
R1是氢或甲基；
R2是相同或不同的直链或支化的、以嵌段或无规形式分布的C2-C4-亚烷基，优选亚乙基、1，2-或1，3-亚丙基或它们的混合物，特别优选亚乙基；
R3是甲基；
n是5-30的整数。
与式I相对应，单体(A)是例如：
-(甲基)丙烯酸与聚亚烷基二醇的反应产物，其中所述聚亚烷基二醇不是末端封端的，不是一端被烷基封端的，不是一端被胺化的，或者不是一端被烷基封端和另一端被胺化的；
-聚亚烷基二醇的烷基醚，其中所述聚亚烷基二醇不是末端封端的，或不是一端被烷基、苯基或烷基苯基封端的。
优选的单体(A)是(甲基)丙烯酸酯和烯丙基醚，其中丙烯酸酯或主要甲基丙烯酸酯是特别优选的。
可以提及的特别合适的单体(A)的实例为：
-(甲基)丙烯酸甲基聚乙二醇酯，甲基聚乙二醇(甲基)丙烯酰胺，
(甲基)丙烯酸甲基聚丙二醇酯，甲基聚丙二醇(甲基)丙烯酰胺，
(甲基)丙烯酸甲基聚丁二醇酯，甲基聚丁二醇(甲基)丙烯酰胺，
(甲基)丙烯酸甲基聚(氧化丙烯/氧化乙烯)酯，甲基聚(氧化丙烯/氧化乙烯)(甲基)丙烯酰胺，(甲基)丙烯酸乙基聚乙二醇酯，乙基聚乙二醇(甲基)丙烯酰胺，(甲基)丙烯酸乙基聚丙二醇酯，乙基聚丙二醇酯(甲基)丙烯酰胺，(甲基)丙烯酸乙基聚丁二醇酯，聚丁二醇(甲基)丙烯酰胺，(甲基)丙烯酸乙基聚(氧化丙烯/氧化乙烯)酯，和乙基聚(氧化丙烯/氧化乙烯)(甲基)丙烯酰胺，各自具有3-50个、优选3-30个、特别优选5-30个氧化烯单元，其中丙烯酸甲基聚乙二醇酯是优选的，甲基丙烯酸甲基聚乙二醇酯是特别优选的；
-乙二醇烯丙基醚和甲基乙二醇烯丙基醚，丙二醇烯丙基醚和甲基丙二醇烯丙基醚，各自具有3-50个、优选3-30个、特别优选5-30个氧化烯单元。
单体(A)在本发明共聚物中的比例是60-99重量％，优选65-90重量％。
特别适用于本发明共聚物的单体(B)是1-乙烯基咪唑的季铵化产物，乙烯基吡啶的季铵化产物，(甲基)丙烯酸酯与氨基醇、特别是N，N-二(C1-C4-烷基)氨基-C2-C6-醇的季铵化产物，含氨基的(甲基)丙烯酰胺、特别是(甲基)丙烯酸的N，N-二(C1-C4-烷基)-氨基-C2-C6-烷基酰胺的季铵化产物，以及二烯丙基烷基胺、特别是二烯丙基-C1-C4-烷基胺的季铵化产物。
非常特别适合的单体(B)具有式IIa-IId：
这些式中的变量具有下述意义：
R 是C1-C4-烷基或苄基，优选甲基、乙基或苄基；
R′是氢或甲基；
Y 是-O-或-NH-；
A 是C1-C6-亚烷基，优选直链或支链C2-C4-亚烷基，特别是1，2-亚乙基，1，3-和1，2-亚丙基，或1，4-亚丁基；
X-是卤离子，例如碘离子，优选氯离子或溴离子，C1-C4-烷基硫酸根，优选甲基硫酸根或乙基硫酸根，C1-C4-烷基磺酸根，优选甲基磺酸根或乙基磺酸根，以及C1-C4-烷基碳酸根。
可以提及的特别优选的单体(B)的具体实例为：
-3-甲基-1-乙烯基氯化咪唑鎓，3-甲基-1-乙烯基咪唑鎓甲基硫酸盐，3-乙基-1-乙烯基咪唑鎓乙基硫酸盐，3-乙基-1-乙烯基氯化咪唑鎓和3-苄基-1-乙烯基氯化咪唑鎓；
-1-甲基-4-乙烯基氯化吡啶鎓，1-甲基-4-乙烯基吡啶鎓甲基硫酸盐和1-苄基-4-乙烯基氯化吡啶鎓；
-甲基丙烯酰胺丙基三甲基氯化铵，甲基丙烯酰胺乙基三甲基氯化铵，丙烯酸三甲基铵基乙酯的氯化物和甲基硫酸盐，甲基丙烯酸三甲基铵基乙酯的氯化物和甲基硫酸盐，丙烯酸二甲基乙基铵基乙酯的乙基硫酸盐，甲基丙烯酸二甲基乙基铵基甲酯的乙基硫酸盐，丙烯酸三甲基铵基丙酯的氯化物和甲基硫酸盐，甲基丙烯酸三甲基铵基丙酯的氯化物和甲基硫酸盐；
-二甲基二烯丙基氯化铵和二乙基二烯丙基氯化铵。
非常特别优选的单体(B)是3-甲基-1-乙烯基氯化咪唑鎓，3-甲基-1-乙烯基咪唑鎓甲基硫酸盐，甲基丙烯酰胺丙基三甲基氯化铵，甲基丙烯酸三甲基铵基乙酯的氯化物，甲基丙烯酸二甲基乙基铵基乙酯的乙基硫酸盐，以及二甲基二烯丙基氯化铵。
本发明的共聚物包含1-40重量％、优选3-30重量％的单体(B)。
(A)与(B)的重量比优选≥2∶1。
关于任选组分(C)，本发明共聚物可包含阴离子性单烯键不饱和单体。
合适的单体(C)是例如：
-α，β-不饱和一羧酸，其优选具有3-6个碳原子，例如丙烯酸、甲基丙烯酸、乙基丙烯酸、巴豆酸和乙烯基乙酸，优选丙烯酸和甲基丙烯酸；
-不饱和二羧酸，其优选具有4-6个碳原子，例如衣康酸和马来酸，它们的酸酐，如马来酸酐；
-烯键不饱和磺酸，例如乙烯基磺酸，丙烯酰胺基丙磺酸，甲基烯丙基磺酸，甲基丙烯酰基磺酸，间-和对-苯乙烯磺酸，(甲基)丙烯酰胺基甲磺酸，(甲基)丙烯酰胺基乙磺酸，(甲基)丙烯酰胺基丙磺酸，2-(甲基)丙烯酰胺基-2-甲基丙烷磺酸，2-丙烯酰胺基-2-丁烷磺酸，3-甲基丙烯酰胺基-2-羟基丙烷磺酸，甲磺酸丙烯酸酯，乙磺酸丙烯酸酯，丙磺酸丙烯酸酯，烯丙氧基苯磺酸，甲基烯丙氧基苯磺酸和1-烯丙氧基-2-羟基丙烷磺酸；
-烯键不饱和膦酸，例如乙烯基膦酸和间-和对-苯乙烯膦酸；
-C2-C4-亚烷基二醇单(甲基)丙烯酸酯和聚(C2-C4-亚烷基)二醇单(甲基)丙烯酸酯的酸性磷酸酯，例如乙二醇单(甲基)丙烯酸酯，丙二醇单(甲基)丙烯酸酯，聚乙二醇单(甲基)丙烯酸酯和聚丙二醇单(甲基)丙烯酸酯。
阴离子单体(C)可以游离酸或盐的形式存在，尤其以碱金属盐和铵盐的形式，特别是烷基铵盐，优选的盐为钠盐。
优选的单体(C)是丙烯酸、甲基丙烯酸、马来酸、乙烯基磺酸、2-(甲基)丙烯酰胺基-2-甲基丙烷磺酸和乙烯基膦酸，特别优选丙烯酸、甲基丙烯酸和2-丙烯酰胺基-2-甲基丙烷磺酸。
单体(C)在本发明共聚物中的比例可最高达39重量％，优选3-30重量％。
如果单体(C)存在于本发明聚合物中，那么(A)与(C)的重量比优选≥2∶1。
关于任选组分(D)，本发明共聚物可包含其它非离子性单烯键不饱和单体。
合适的单体(D)是例如：
-单烯键不饱和C3-C6-羧酸、尤其丙烯酸和甲基丙烯酸与一元C1-C22-醇、特别是C1-C16-醇形成的酯；和单烯键不饱和C3-C6-羧酸、尤其丙烯酸和甲基丙烯酸与二元C2-C4-醇形成的羟烷基酯，例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸仲丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸乙基己基酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸十六酯、(甲基)丙烯酸棕榈基酯和(甲基)丙烯酸硬脂基酯、(甲基)丙烯酸羟乙酯、(甲基)丙烯酸羟丙酯和(甲基)丙烯酸羟丁酯；
-单烯键不饱和C3-C6-羧酸、尤其丙烯酸和甲基丙烯酸与C1-C12-烷基胺和二(C1-C4-烷基)胺形成的酰胺，例如N-甲基(甲基)丙烯酰胺、N，N-二甲基(甲基)丙烯酰胺，N-乙基(甲基)丙烯酰胺、N-丙基(甲基)丙烯酰胺、N-叔丁基(甲基)丙烯酰胺、N-叔辛基(甲基)丙烯酰胺和N-十一烷基(甲基)丙烯酰胺，和(甲基)丙烯酰胺；
-饱和C2-C30-羧酸、特别是C2-C14-羧酸的乙烯基酯，例如乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、2-乙基己酸乙烯酯和月桂酸乙烯酯；
-乙烯基C1-C30-烷基醚，特别是乙烯基C1-C18-烷基醚，例如乙烯基甲基醚、乙烯基乙基醚、乙烯基正丙基醚、乙烯基异丙基醚、乙烯基正丁基醚、乙烯基异丁基醚、乙烯基2-乙基己基醚和乙烯基十八烷基醚；
-N-乙烯基酰胺和N-乙烯基内酰胺，例如N-乙烯基甲酰胺、N-乙烯基-N-甲基甲酰胺、N-乙烯基乙酰胺、N-乙烯基-N-甲基乙酰胺、N-乙烯基吡咯烷酮、N-乙烯基哌啶酮和N-乙烯基己内酰胺；
-脂族和芳族烯烃，例如乙烯、丙烯、C4-C24-α-烯烃，特别是C4-C16-α-烯烃，例如丁烯、异丁烯、二异丁烯、苯乙烯和α-甲基苯乙烯，以及具有活性双键的二烯烃，例如丁二烯；
-不饱和腈，例如丙烯腈和甲基丙烯腈。
优选的单体(D)是(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酰胺、乙酸乙烯酯、丙酸乙烯酯、乙烯基甲基醚、N-乙烯基甲酰胺、N-乙烯基吡咯烷酮和N-乙烯基己内酰胺。
如果单体(D)存在于本发明共聚物中，则它们的比例可高达30重量％。
本发明共聚物的平均分子量Mw是2000-100 000，优选3000-50 000，特别优选3000-25 000。
本发明共聚物可通过单体(A)和(B)和如果期望的话(C)和/或(D)的自由基聚合来制备。
代替季铵化的单体(B)，还可以使用相应的叔胺。在这种情况下，季铵化可以在聚合后通过使所得共聚物与烷基化试剂反应进行，烷基化试剂是例如卤代烷、硫酸二烷基酯和碳酸二烷基酯，或苄基卤化物如苄基氯。可以提及的合适的烷基化试剂的实例是氯代甲烷、溴代甲烷和碘代甲烷，氯代乙烷和溴代乙烷，硫酸二甲酯，硫酸二乙酯，碳酸二甲酯和碳酸二乙酯。
所述阴离子单体(C)可以游离酸形式或以部分或完全被碱中和的形式用于聚合中。适用于中和的碱是无机碱，例如碱金属氢氧化物、碱金属碳酸盐、碱金属碳酸氢盐和氨；和有机碱，例如胺，特别是醇胺。可以列举的具体实例为：氢氧化钠溶液、氢氧化钾溶液、碳酸钠、碳酸氢钠、乙醇胺、二乙醇胺和三乙醇胺。
单体的自由基聚合可依照所有的公知方法进行，优选溶液聚合和乳液聚合方法。
所述聚合有利地在水中进行。但是，还可以使用水和极性有机溶剂的混合物或极性溶剂本身作为反应介质。
合适的有机溶剂的实例为脂族和脂环族一元醇，例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇、正己醇和环己醇；多元醇，例如二醇，例如乙二醇、丙二醇和丁二醇，和甘油；多元醇的烷基醚，例如所述二元醇的甲基和乙基醚；醚醇，例如二甘醇、三甘醇和双丙甘醇；环醚，例如四氢呋喃和二噁烷；和酮，如丙酮。
合适的引发剂是能热分解或光化学分解(光引发剂)形成自由基的化合物。
在可热活化的聚合引发剂中，优选分解温度在20-180℃、尤其在50-90℃范围内的引发剂。特别优选的热引发剂的实例是无机过氧化合物，例如过硫酸氢盐(过硫酸氢铵，优选过硫酸氢钠)、过硫酸盐、过碳酸盐和过氧化氢；有机过氧化合物，例如过氧二乙酰、过氧化二叔丁基、过氧化二戊基、过氧化二辛酰、过氧化二癸酰、过氧化二月桂酰、过氧化二苯甲酰、过氧化二(邻-甲苯基)、过氧化琥珀酰、过乙酸叔丁酯、过马来酸叔丁酯、过异丁酸叔丁酯、过新戊酸叔丁酯、过辛酸叔丁酯、过新癸酸叔丁酯、过苯甲酸叔丁酯、过氧化叔丁基、氢化氧化叔丁基、氢过氧化枯烯、过氧-2-乙基己酸叔丁酯和过氧二氨基甲酸二异丙酯；偶氮化合物，例如2，2’-偶氮二异丁腈、2，2’-偶氮二(2-甲基丁腈)、2，2’-偶氮二(N，N’-二亚甲基异丁眯)二盐酸化物和偶氮二(2-脒基丙烷)二盐酸化物。
合适的光引发剂的实例是苯甲酮、苯乙酮、苯偶姻醚、苄基二烷基酮和它们的衍生物。
聚合引发剂是根据对要聚合的材料的要求使用，用量一般是基于要聚合的单体计的0.01-15重量％，优选0.5-5重量％，并且可以单独使用，或为了利用有利的协同效应而以彼此组合的方式使用。
为了限制本发明共聚物的摩尔质量，在聚合中可加入传统调节剂，如巯基化合物，例如巯基乙醇、巯基乙酸和亚硫酸氢钠。调节剂的合适用量一般是基于要聚合的单体计的0.01-10重量％，优选0.1-5重量％。
聚合温度一般为10-200℃，尤其50-100℃。
所述聚合优选在大气压力下进行。但是，也可以在闭合系统中在其自生压力下进行。
本发明共聚物特别适合用于分散粘土矿物。即使添加非常少量的所述共聚物(例如基于粘土矿物计的0.05-2重量％)也能够稳定粘土矿物的水分散液。
本发明共聚物特别适合作为固体和液体洗衣用洗涤剂的添加剂。在这方面，它们尤其以下述有利的应用性能为特征：它们以优异的方式分散污垢颗粒并进而防止污垢在洗涤过程中再沉积在织物上。因而防止织物变灰。另外，它们改善液体和固体洗涤剂的一次去污力。这特别适合粒状污垢，而且包含油和油脂的憎水性织物污垢更容易被除去。特别是，加入本发明共聚物能使土壤状污垢更容易被除去。另外，它们可以毫无问题地混入固体和液体洗涤剂制剂中。在这方面，应该强调的是液体洗涤剂的稳定性和均匀性不会被本发明共聚物削弱。即使在长期储存中也没有观察到不期望的相形成和沉淀。
实施例
1.本发明共聚物的制备
下面给出的平均分子量Mw是依照尺寸排除色谱方法使用窄分布的线性聚麦芽三糖和麦芽己糖作为校正标准测定的。
共聚物1
先将246.5g水装入装配有搅拌器、回流冷凝器、内部温度计和滴液漏斗的2升聚合容器中，在用氮气冲洗后，加热到80℃。然后连续滴加568.8g浓度50重量％的甲基丙烯酸甲基聚乙二醇酯水溶液(Mn是1000)(原料1)，34.7g浓度45重量％的3-甲基-1-乙烯基咪唑鎓甲基硫酸盐(原料2)，15g巯基乙醇与50g水的混合物(原料3)和6.0g 2，2’-偶氮(2-脒基丙烷)二盐酸化物和80g水的引发剂混合物(原料4)(原料1、2和3在3小时内添加，原料4在4小时内添加)。当引发剂添加完成后，反应混合物在80℃下再搅拌1小时，然后在该温度下将包含1.5g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和20g水的另一种引发剂混合物一次加入。在于80℃下搅拌2小时后，加入2.75g浓度30重量％的过氧化氢，然后在80℃下搅拌该混合物30分钟。在冷却到室温后，过滤该反应混合物。
这样产生一种淡黄色透明的聚合物溶液，其固含量为30.4重量％，pH为4.6。该聚合物的平均分子量Mw为4600。
共聚物2
先将239.0g水装入装配有搅拌器、回流冷凝器、内部温度计和滴液漏斗的2升聚合容器中，在用氮气冲洗后，加热到80℃。然后连续滴加51.5g浓度50重量％的2-丙烯酰胺基-2-甲基丙烷磺酸钠盐水溶液(原料1)，109.9g浓度45重量％的3-甲基-1-乙烯基咪唑鎓甲基硫酸盐(原料2)，449.6g浓度50重量％的甲基丙烯酸甲基聚乙二醇酯水溶液(Mn是1000)(原料3)，9g巯基乙醇和50g水的混合物(原料4)和6.0g 2，2’-偶氮(2-脒基丙烷)二盐酸化物和80g水的引发剂混合物(原料5)(原料1、2、3和4在3小时内添加，原料5在4小时内添加)。当引发剂添加完成后，反应混合物在80℃下再搅拌1小时，然后在该温度下将包含1.5g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和20g水的另一种引发剂混合物一次加入。在于80℃下搅拌2小时后，加入1.65g浓度30重量％的过氧化氢，然后在80℃下再搅拌该混合物30分钟。在冷却到室温并过滤后，将3.6g浓度10重量％的氢氧化钠溶液加入滤液中。
这样产生一种淡黄色透明的聚合物溶液，其固含量为30.7重量％，pH为6.5。该聚合物的平均分子量Mw为6100。
共聚物3
先将243.7g水装入装配有搅拌器、回流冷凝器、内部温度计和滴液漏斗的2升聚合容器中，在用氮气冲洗后，加热到80℃。然后连续滴加20.7g甲基丙烯酸和40g水的混合物(原料1)，64.7g浓度60重量％的二烯丙基二甲基氯化铵水溶液(原料2)，480.9g 浓度50重量％的甲基丙烯酸甲基聚乙二醇酯水溶液(Mn是1000)(原料3)，9g巯基乙醇与50g水的混合物(原料4)和6.0g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物与80g水的引发剂混合物(原料5)(原料1、2、3和4在3小时内添加，原料5在4小时内添加)。当引发剂添加完成后，反应混合物在80℃下再搅拌1小时，然后在该温度下将包含1.5g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和20g水的另一种引发剂混合物一次加入。在于80℃下搅拌2小时后，加入1.65g浓度30重量％的过氧化氢并在80℃下再搅拌该混合物30分钟。在冷却到室温并过滤后，将75g浓度10重量％的氢氧化钠溶液加入滤液中。
这样产生一种淡黄色透明的聚合物溶液，其固含量为28.8重量％，pH为6.5。该聚合物的平均分子量Mw为9800。
共聚物4
先将197.0g水装入装配有搅拌器、回流冷凝器、内部温度计和滴液漏斗的2升聚合容器中，在用氮气冲洗后，加热到80℃。然后连续滴加417.9g浓度50重量％的甲基丙烯酸甲基聚乙二醇酯水溶液(Mn是1000)(原料1)，92.1g浓度50重量％的甲基丙烯酰胺丙基三甲基氯化铵水溶液(原料2)，13g巯基乙醇与50g水的混合物(原料3)和5.1g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物与80g水的引发剂混合物(原料4)(原料1、2和3在3小时内添加，原料4在4小时内添加)。当引发剂添加完成后，反应混合物在80℃下再搅拌1小时，然后在该温度下将包含1.3g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和20g水的另一种引发剂混合物一次加入。在于80℃下搅拌2小时后，加入1.95g浓度30重量％的过氧化氢并在80℃下再搅拌该混合物30分钟。冷却到室温后，过滤该反应混合物。
这样产生一种淡黄色透明的聚合物溶液，其固含量为32.7重量％，pH为5.6。该聚合物的平均分子量Mw为5000。
共聚物5
先将250.1g水装入装配有搅拌器、回流冷凝器、内部温度计和滴液漏斗的2升聚合容器中，在用氮气冲洗后，加热到80℃。然后连续滴加51.5g浓度50重量％的2-丙烯酰胺基-2-甲基丙烷磺酸钠盐水溶液(原料1)，54.0g浓度50重量％的甲基丙烯酰胺丙基三甲基氯化铵水溶液(原料2)，489.8g浓度50重量％的甲基丙烯酸甲基聚乙二醇酯水溶液(Mn是1000)(原料3)，9g巯基乙醇与50g水的混合物(原料4)和6.0g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和80g水的引发剂混合物(原料5)(原料1、2、3和4在3小时内添加，原料5在4小时内添加)。当引发剂添加完成后，反应混合物在80℃下再搅拌1小时，然后在该温度下将包含1.5g 2，2’-偶氮二(2-脒基丙烷)二盐酸化物和20g水的另一种引发剂混合物一次加入。在于80℃下搅拌2小时后，加入1.65g浓度30重量％的过氧化氢并在80℃下再搅拌该混合物30分钟。在冷却到室温并过滤后，将0.8g浓度10重量％的氢氧化钠溶液加入滤液中。
这样产生一种淡黄色透明的聚合物溶液，其固含量为30.2重量％，pH为6.5。该聚合物的平均分子量Mw为6500。
II.本发明共聚物在洗衣用洗涤剂中的用途
测定本发明共聚物的一次和二次去污力。
为了进行洗涤实验，使用基于沸石的固体洗衣用洗涤剂制剂(LD 1)、基于磷酸盐的固体洗衣用洗涤剂制剂(LD 3)和液体洗衣用洗涤剂制剂(LD 2)，它们的组成示于表1，洗涤条件列于表2。
表1
| LD 1 | LD 2 | LD 3 | |
| 成分 | [重量％] | [重量％] | [重量％] |
| 直链烷基苯磺酸盐 | 5.0 | 20.0 | |
| C<sub>12</sub>-C<sub>18</sub>-烷基硫酸盐 | 26.7 | ||
| C<sub>12</sub>-脂肪醇硫酸盐x 2EO | 7.1 | ||
| C<sub>13</sub>C<sub>15</sub>-羰基合成醇x 7EO | 5.0 | ||
| C<sub>12</sub>C<sub>14</sub>-脂肪醇x 7EO | 6.0 | ||
| 皂 | 1.4 | ||
| 椰子脂酸 | 5.0 | ||
| 氢氧化钾 | 1.4 | ||
| 柠檬酸钠x 2H<sub>2</sub>O | 2.1 | ||
| 沸石A | 30.0 | ||
| 三磷酸五钠 | 20.0 | ||
| 碳酸钠 | 12.0 | 10.0 | |
| 硅酸钠×5H<sub>2</sub>O | 3.6 | 4.5 | |
| 四硼酸二钠 | 2.2 | ||
| 过硼酸钠一水合物 | 20.0 | ||
| 四乙酰基乙二胺 | 6.0 | ||
| 甲基丙基乙二醇 | 10 | ||
| 硫酸钠 | 7.0 | 25.0 |
| LD 1 | LD 2 | LD 3 | |
| 水 | 添加到100 | 添加到100 | 添加到100 |
表2
为了确定一次去污力，在洗涤前后分别利用Datacolor光度计(2000)以反射度(％)为参考测量被污染织物的白度。反射度值越高，一次去污力越好。
获得的结果总结在表3中。
表3
为了确定二次去污力，通过在洗涤之前和之后分别用Datacolor光度计(2000)以反射度(％)为参考测量被污染织物的白度来确定白色试验织物的变灰程度。白度值下降越多，织物的变灰程度越大，反之亦然。
获得的结果总结在表4中。
表4
Claims (6)
1.一种共聚物用作用于粘土矿物的分散剂的用途，所述共聚物以共聚形式包含
(A)60-99重量％的至少一种式I的单烯键不饱和聚氧化烯单体
其中的变量具有下述意义：
当Y是-O-时，X是-CH2-或-CO-；
当Y是-NH-时，X是-CO-；
Y是-O-或-NH-；
R1是氢或甲基；
R2是相同或不同的C2-C6-亚烷基，其可以以嵌段或无规形式分布；
R3是氢或C1-C4-烷基；
n是3-50的整数，
(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体，
(C)0-39重量％的阴离子性单烯键不饱和单体，和
(D)0-30重量％的其它非离子性单烯键不饱和单体，
并且所述共聚物具有2000-100000的平均分子量Mw。
2.如权利要求1所述的用途，其中所述共聚物以共聚形式包含至少一种其中变量具有下述意义的式I单体作为单体(A)：
X是-CO-或-CH2-；
Y是-O-；
R1是氢或甲基；
R2是亚乙基、亚丙基或它们的混合物；
R3是甲基；
n是5-30的整数。
3.如权利要求1或2所述的用途，其中所述共聚物以共聚形式包含至少一种式IIa至IId的单体作为单体(B)：
其中的变量具有下述意义：
R是C1-C4-烷基或苄基；
R′是氢或甲基；
Y是-O-或-NH-；
A是C1-C6-亚烷基；
X-是卤离子，C1-C4-烷基硫酸根，C1-C4-烷基磺酸根或C1-C4-烷基碳酸根。
4.如权利要求1或2所述的用途，其中所述共聚物以共聚形式包含60-98重量％的单体(A)、1-39重量％的单体(B)和1-39重量％的单体(C)。
5.如权利要求1或2所述的用途，其中(A)与(B)的重量比≥2∶1，并且在所述共聚物以共聚形式包含单体(C)的情况下，(A)与(C)的重量比也是≥2∶1。
6.一种共聚物，其以共聚形式包含：
(A)60-99重量％的至少一种式I的单烯键不饱和聚氧化烯单体
其中的变量具有下述意义：
当Y是-O-时，X是-CH2-或-CO-；
当Y是-NH-时，X是-CO-；
Y是-O-或-NH-；
R1是氢或甲基；
R2是相同或不同的C2-C6-亚烷基，其可以以嵌段或无规形式分布；
R3是氢或C1-C4-烷基；
n是3-50的整数，
(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体，其选自通式IIa或IIb的单体(B)或甲基丙烯酰胺丙基三甲基氯化铵：
其中的变量具有下述意义：
R是C1-C4-烷基或苄基；
X-是卤离子、C1-C4-烷基硫酸根、C1-C4-烷基磺酸根或C1-C4-烷基碳酸根，
(C)0-39重量％的阴离子性单烯键不饱和单体，和
(D)0-30重量％的其它非离子性单烯键不饱和单体，
并且所述共聚物具有2000-100000的平均分子量Mw，
或者
所述共聚物以共聚形式包含：
(A)60-99重量％的至少一种式I的单烯键不饱和聚氧化烯单体
其中的变量具有下述意义：
当Y是-O-时，X是-CH2-；
当Y是-NH-时，X是-CO-；
Y是-O-或-NH-；
R1是氢或甲基；
R2是相同或不同的C2-C6-亚烷基，其可以以嵌段或无规形式分布；
R3是氢或C1-C4-烷基；
n是3-50的整数，
(B)1-40重量％的至少一种季铵化的含氮单烯键不饱和单体，其选自：
通式IIa或IIb的单体(B)：
其中的变量具有下述意义：
R是C1-C4-烷基或苄基；
X-是卤离子，C1-C4-烷基硫酸根，C1-C4-烷基磺酸根或C1-C4-烷基碳酸根，或选自以下单体(B)：
-甲基丙烯酰胺丙基三甲基氯化铵，丙烯酸三甲基铵基乙酯的氯化物和甲基硫酸盐，甲基丙烯酸三甲基铵基乙酯的氯化物和甲基硫酸盐，丙烯酸二甲基乙基铵基乙酯的乙基硫酸盐，甲基丙烯酸二甲基乙基铵基甲酯的乙基硫酸盐，丙烯酸三甲基铵基丙酯的甲基硫酸盐，甲基丙烯酸三甲基铵基丙酯的甲基硫酸盐；
-二乙基二烯丙基氯化铵，
(C)0-39重量％的阴离子性单烯键不饱和单体，和
(D)0-30重量％的其它非离子性单烯键不饱和单体，
并且所述共聚物具有2000-100000的平均分子量Mw。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52366303P | 2003-11-21 | 2003-11-21 | |
| US60/523,663 | 2003-11-21 | ||
| PCT/EP2004/013020 WO2005049676A1 (de) | 2003-11-21 | 2004-11-17 | Polyalkylenoxidgruppen und quartäre stickstoffatome enthaltende copolymere |
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| Publication Number | Publication Date |
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| CN1882623A CN1882623A (zh) | 2006-12-20 |
| CN1882623B true CN1882623B (zh) | 2010-05-26 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2004800343326A Expired - Fee Related CN1882623B (zh) | 2003-11-21 | 2004-11-17 | 包含聚氧化烯基团和季氮原子的共聚物 |
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| Country | Link |
|---|---|
| US (1) | US20070129516A1 (zh) |
| EP (1) | EP1687348B1 (zh) |
| JP (1) | JP4427550B2 (zh) |
| CN (1) | CN1882623B (zh) |
| AT (1) | ATE414113T1 (zh) |
| BR (1) | BRPI0416513B1 (zh) |
| CA (1) | CA2545016A1 (zh) |
| DE (1) | DE502004008456D1 (zh) |
| ES (1) | ES2314493T3 (zh) |
| WO (1) | WO2005049676A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1685227B1 (en) * | 2003-11-21 | 2008-08-20 | The Procter & Gamble Company | Laundry compositions having copolymers containing polyalkylene oxide groups and quaternary nitrogen atoms and a surfactant system |
| JP5475270B2 (ja) * | 2008-11-20 | 2014-04-16 | 花王株式会社 | 洗剤組成物 |
| US8461245B2 (en) * | 2011-02-15 | 2013-06-11 | W.R. Grace & Co.-Conn. | Copolymers for treating construction aggregates |
| FR2985727B1 (fr) | 2012-01-16 | 2014-05-09 | Snf Sas | Nouveaux polymeres peignes utilisables en cosmetique et detergence |
| KR102043249B1 (ko) * | 2012-04-24 | 2019-11-11 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 공중합체로 그래프팅된 부직 물품 |
| EP2853550A1 (en) * | 2013-09-27 | 2015-04-01 | Construction Research & Technology GmbH | Cationic copolymers |
| US9127236B2 (en) | 2013-10-09 | 2015-09-08 | Ecolab Usa Inc. | Alkaline detergent composition containing a carboxylic acid terpolymer for hard water scale control |
| US9487738B2 (en) * | 2013-10-09 | 2016-11-08 | Ecolab Usa Inc. | Solidification matrix comprising a carboxylic acid terpolymer |
| US9127235B2 (en) * | 2013-10-09 | 2015-09-08 | Ecolab Usa Inc. | Alkaline detergent composition containing a carboxylic acid/polyalkylene oxide copolymer for hard water scale control |
| US10570306B2 (en) | 2015-07-30 | 2020-02-25 | Basf Se | Compositions containing polyanion, ethoxylated cationic polymer and phyllosilicates for improved oxygen barrier coatings |
| PL3196284T3 (pl) * | 2016-01-21 | 2018-11-30 | Henkel Ag & Co. Kgaa | Usuwanie zabrudzeń antyperspirantowych |
| ES2682801T3 (es) * | 2016-01-21 | 2018-09-21 | Henkel Ag & Co. Kgaa | Principios activos poliméricos que mejoran el poder de lavado primario |
| WO2017176501A1 (en) * | 2016-04-08 | 2017-10-12 | The Procter & Gamble Company | Automatic dishwashing cleaning composition |
| RU2736718C2 (ru) * | 2016-04-08 | 2020-11-19 | Басф Се | Сополимеры, содержащие полиалкиленоксидные группы и четвертичные атомы азота |
| EP3241889B1 (en) * | 2016-05-03 | 2019-03-20 | The Procter and Gamble Company | Cleaning composition |
| ES2874024T3 (es) * | 2017-10-05 | 2021-11-04 | Procter & Gamble | Composición de limpieza para el lavado de vajillas |
| CN111676003B (zh) * | 2020-07-22 | 2022-03-22 | 西南石油大学 | 一种环保型低分子量支化聚醚氨页岩插层抑制剂 |
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| CN1334830A (zh) * | 1998-12-29 | 2002-02-06 | B·F·谷德里奇公司 | 亲水性两性聚合物 |
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| DE19806482A1 (de) * | 1998-02-17 | 1999-08-19 | Sueddeutsche Kalkstickstoff | Wasserlösliche oder wasserquellbare sulfogruppenhaltige Copolymere, Verfahren zu deren Herstellung und ihre Verwendung |
| JP2000302649A (ja) * | 1999-04-26 | 2000-10-31 | Mitsubishi Chemicals Corp | 毛髪化粧料 |
| DE50015912D1 (de) * | 1999-07-15 | 2010-06-10 | Clariant Produkte Deutschland | Wasserlösliche Polymere und ihre Verwendung in kosmetischen und pharmazeutischen Mitteln |
| JP2001181354A (ja) * | 1999-12-28 | 2001-07-03 | Lion Corp | カチオン性ポリマー |
| FR2810669B1 (fr) * | 2000-06-27 | 2002-08-30 | Atofina | Copolymeres hydrosolubles thermosensibles a base de (meth) acrylate (poly)ethoxyle, leur fabrication et leur utilisation pour la preparation de film, adhesifs et liants pour nappes fibreuses |
| DE10059830A1 (de) * | 2000-12-01 | 2002-06-13 | Clariant Gmbh | Kationisch modifizierte Kammpolymere auf Basis von Acryloyldimethyltaurinsäure |
| DE10059828A1 (de) * | 2000-12-01 | 2002-06-13 | Clariant Gmbh | Kammförmige Copolymere auf Basis von Acryloyldimethyltaurinsäure |
| JP2004162207A (ja) * | 2002-11-13 | 2004-06-10 | Canon Inc | サイズ剤 |
| EP1685227B1 (en) * | 2003-11-21 | 2008-08-20 | The Procter & Gamble Company | Laundry compositions having copolymers containing polyalkylene oxide groups and quaternary nitrogen atoms and a surfactant system |
-
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- 2004-11-17 US US10/579,547 patent/US20070129516A1/en not_active Abandoned
- 2004-11-17 WO PCT/EP2004/013020 patent/WO2005049676A1/de not_active Application Discontinuation
- 2004-11-17 CA CA002545016A patent/CA2545016A1/en not_active Abandoned
- 2004-11-17 ES ES04818789T patent/ES2314493T3/es active Active
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- 2004-11-17 BR BRPI0416513A patent/BRPI0416513B1/pt not_active IP Right Cessation
- 2004-11-17 DE DE502004008456T patent/DE502004008456D1/de active Active
- 2004-11-17 CN CN2004800343326A patent/CN1882623B/zh not_active Expired - Fee Related
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| CN1334830A (zh) * | 1998-12-29 | 2002-02-06 | B·F·谷德里奇公司 | 亲水性两性聚合物 |
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| Publication number | Publication date |
|---|---|
| CN1882623A (zh) | 2006-12-20 |
| US20070129516A1 (en) | 2007-06-07 |
| BRPI0416513B1 (pt) | 2015-10-20 |
| DE502004008456D1 (de) | 2008-12-24 |
| CA2545016A1 (en) | 2005-06-02 |
| EP1687348B1 (de) | 2008-11-12 |
| BRPI0416513A (pt) | 2007-01-09 |
| EP1687348A1 (de) | 2006-08-09 |
| JP4427550B2 (ja) | 2010-03-10 |
| WO2005049676A1 (de) | 2005-06-02 |
| JP2007511654A (ja) | 2007-05-10 |
| ATE414113T1 (de) | 2008-11-15 |
| ES2314493T3 (es) | 2009-03-16 |
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