JP4180656B2 - 水溶性アミノプラスト−エーテル コポリマー - Google Patents
水溶性アミノプラスト−エーテル コポリマー Download PDFInfo
- Publication number
- JP4180656B2 JP4180656B2 JP50183297A JP50183297A JP4180656B2 JP 4180656 B2 JP4180656 B2 JP 4180656B2 JP 50183297 A JP50183297 A JP 50183297A JP 50183297 A JP50183297 A JP 50183297A JP 4180656 B2 JP4180656 B2 JP 4180656B2
- Authority
- JP
- Japan
- Prior art keywords
- aminoplast
- copolymer
- carbon atoms
- ether
- ether copolymer
- 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.)
- Expired - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 89
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 229920003180 amino resin Polymers 0.000 claims abstract description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 33
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000002252 acyl group Chemical group 0.000 claims abstract description 8
- 125000005529 alkyleneoxy group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 229920000570 polyether Polymers 0.000 claims description 34
- 230000002209 hydrophobic effect Effects 0.000 claims description 31
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 27
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 239000003377 acid catalyst Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 12
- -1 aroxyalkyl Chemical group 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 229920001281 polyalkylene Polymers 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 2
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 2
- DSJAMCDTNOAPCS-UHFFFAOYSA-N C1=CC=C(C=C1)ON(C(=O)O)NC(=O)N Chemical compound C1=CC=C(C=C1)ON(C(=O)O)NC(=O)N DSJAMCDTNOAPCS-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 238000004132 cross linking Methods 0.000 claims 3
- 150000007516 brønsted-lowry acids Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 42
- 239000011347 resin Substances 0.000 description 42
- 239000002562 thickening agent Substances 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 229920000642 polymer Polymers 0.000 description 28
- 239000003973 paint Substances 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical group 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 9
- 239000004816 latex Substances 0.000 description 9
- 229920000126 latex Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 8
- 125000001165 hydrophobic group Chemical group 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical compound OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229920005684 linear copolymer Polymers 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229940114077 acrylic acid Drugs 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
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- 125000004185 ester group Chemical group 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
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- 239000000049 pigment Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
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- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
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- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
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- 239000002826 coolant Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000008131 herbal destillate Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002989 phenols Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/424—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compounds Of Unknown Constitution (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/476,193 | 1995-06-07 | ||
| US08/476,193 US5914373A (en) | 1995-06-07 | 1995-06-07 | Water soluble aminoplast-ether copolymers |
| PCT/US1996/009529 WO1996040815A1 (en) | 1995-06-07 | 1996-06-07 | Water-soluble aminoplast-ether copolymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001515525A JP2001515525A (ja) | 2001-09-18 |
| JP2001515525A5 JP2001515525A5 (enExample) | 2004-07-29 |
| JP4180656B2 true JP4180656B2 (ja) | 2008-11-12 |
Family
ID=23890884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50183297A Expired - Lifetime JP4180656B2 (ja) | 1995-06-07 | 1996-06-07 | 水溶性アミノプラスト−エーテル コポリマー |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5914373A (enExample) |
| EP (1) | EP0830409B1 (enExample) |
| JP (1) | JP4180656B2 (enExample) |
| AT (1) | ATE231528T1 (enExample) |
| AU (1) | AU721667B2 (enExample) |
| CA (1) | CA2221705C (enExample) |
| DE (1) | DE69625904T2 (enExample) |
| MX (1) | MX9709619A (enExample) |
| WO (1) | WO1996040815A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19714016A1 (de) * | 1997-04-04 | 1998-10-08 | Basf Ag | Emulgatoren für Aminoharze |
| US6140391A (en) * | 1998-10-09 | 2000-10-31 | Marconi Data Systems Inc. | Reactive jet ink composition |
| AU772095B2 (en) * | 1999-08-13 | 2004-04-08 | Sud-Chemie, Inc. | Nonionic associative thickener composition with improved viscosity retention upon tinting in architectural latex coating |
| US6528046B1 (en) * | 1999-10-22 | 2003-03-04 | Wella Ag | Clear hair treatment composition |
| FR2802089B1 (fr) * | 1999-12-08 | 2002-01-18 | Oreal | Composition de teinture d'oxydation pour fibres keranitiques comprenant un polymere epaississant a squelette aminoplaste-ether |
| FR2802092B1 (fr) | 1999-12-08 | 2002-01-18 | Oreal | Composition de decoloration pour fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| FR2802090B1 (fr) | 1999-12-08 | 2002-01-18 | Oreal | Composition de teinture directe pour fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| FR2802093B1 (fr) | 1999-12-08 | 2002-01-18 | Oreal | Composition pour la decoloration ou la deformation permanente des fibres keratiniques comprenant un polymere epaississant a squelette aminoplaste-ether |
| DE10002513A1 (de) * | 2000-01-21 | 2001-08-16 | Wella Ag | Zusammensetzung für ein Haarbehandlungsmittel in Form eines Aerosol-Schaumes |
| DE10023028A1 (de) * | 2000-05-11 | 2001-12-06 | Wella Ag | Mittel zum Färben von Keratinfasern |
| TW572965B (en) | 2000-08-04 | 2004-01-21 | Sued Chemie Ag | Use of amphiphilic polymers or copolymers for the surface modification of reactive inorganic fillers |
| DE10038147A1 (de) * | 2000-08-04 | 2002-02-14 | Sued Chemie Ag | Propfpolymere oder -copolymere |
| FR2815853B1 (fr) * | 2000-10-27 | 2002-12-27 | Oreal | Composition cosmetique capillaire sous forme de mousse comprenant au moins un polymere epaississant a squelette aminoplaste-ether |
| DE10119292A1 (de) * | 2001-04-19 | 2002-10-31 | Faber Castell Ag | Puderstift |
| DE10127104A1 (de) | 2001-06-02 | 2002-12-05 | Wella Ag | Zweiphasiges Haargel |
| DE20114179U1 (de) | 2001-08-28 | 2001-10-25 | Wella Ag, 64295 Darmstadt | Färbemittel für Keratinfasern |
| DE10147501A1 (de) | 2001-09-26 | 2003-04-10 | Wella Ag | Perlglänzende Haarkur |
| DE10163985A1 (de) * | 2001-12-24 | 2003-07-03 | Sued Chemie Ag | Aminoplasteinheiten enthaltende Copolymere und ihre Verwendung als Dispergier- oder Stabilisiermittel |
| DE60315103T2 (de) * | 2002-10-11 | 2008-04-10 | Rohm And Haas Co. | Verfahren zur Verbesserung von Viskosität von Verdickungsmitteln für wässrige Systeme |
| DE10310175A1 (de) * | 2003-03-08 | 2004-09-16 | Süd-Chemie AG | Assoziativverdickerpräparation |
| US7736631B2 (en) * | 2003-04-01 | 2010-06-15 | L'oreal S.A. | Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing |
| US6900255B2 (en) | 2003-05-16 | 2005-05-31 | Hercules Incorporated | Suppression of aqueous viscosity of nonionic associative thickeners |
| US7377946B2 (en) * | 2003-07-09 | 2008-05-27 | L'oréal | Composition comprising at least one substituted 2-[2-(4-amino phenyl)ethenyl]-1-pyridinium derivative, process for treating keratin fibres using it, device and use thereof |
| US7425221B2 (en) * | 2004-09-13 | 2008-09-16 | L'oreal S.A. | Composition comprising at least one substituted derivative of carbocyanine, method for treating keratin fibers using it, device and use |
| FR2875130B1 (fr) | 2004-09-13 | 2006-12-15 | Oreal | Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation |
| FR2875132B1 (fr) | 2004-09-13 | 2007-07-13 | Oreal | Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation |
| US7419511B2 (en) * | 2004-09-13 | 2008-09-02 | L'oreal, S.A. | Compositions comprising at least one substituted carbocyanin derivative, processes for treating keratin fibers using them, device therefor and uses thereof |
| FR2875131B1 (fr) | 2004-09-13 | 2007-09-28 | Oreal | Composition comprenant au moins un derive substitue de carbocyanine, procede de traitement des fibres keratiniques la mettant en oeuvre, dispositif et utilisation |
| US7427301B2 (en) * | 2004-09-13 | 2008-09-23 | L'ORéAL S.A. | Composition comprising at least one substituted carbocyanin derivative, process for treating keratin fibers using it, device therefor and use thereof |
| US7531008B2 (en) * | 2005-11-30 | 2009-05-12 | L'oreal S.A. | Use of at least one cationic cyanin derivative for dyeing the hair, composition containing it, process for treating keratin fibers using the composition, and device therefor |
| EP2195389A4 (en) * | 2007-10-01 | 2011-03-30 | Elementis Specialties Inc | METHOD FOR IMPROVING THE COLOR ACCEPTANCE OF VISCOSITY STABILIZED LATEX COLORS |
| US20090151601A1 (en) * | 2007-12-17 | 2009-06-18 | Elementis Specialties, Inc. | Low voc waterbased coatings with efflorescence resistance |
| US7868122B2 (en) * | 2008-06-19 | 2011-01-11 | Southern Clay Products, Inc. | Tint-viscosity stabilization polymeric thickeners |
| US20100069536A1 (en) * | 2008-07-17 | 2010-03-18 | Sau Arjun C | Process for tailoring water-borne coating compositions |
| US8048268B2 (en) * | 2009-10-27 | 2011-11-01 | Enzymatic Deinking Technologies, Llc | Method of controlling organic contaminants in pulp and paper making processes |
| FR2954093B1 (fr) | 2009-12-22 | 2012-02-24 | Oreal | Agent de coloration et/ou de decoloration des fibres keratiniques en deux parties ou plus sous forme d'emulsion et de dispersion |
| RS52961B (sr) * | 2010-01-26 | 2014-02-28 | Omya Development Ag | Premazna kompozicija koja obuhvata zrnasti submikronski kalcijumkarbonat, postupak za njenu pripremu i upotreba zrnastog submikronskog kalcijumkarbonata u premaznim kompozicijama |
| US8905135B2 (en) * | 2010-03-24 | 2014-12-09 | Halliburton Energy Services, Inc. | Zero shear viscosifying agent |
| DE102010031683A1 (de) | 2010-07-20 | 2012-01-26 | Bayer Materialscience Ag | Polyisocyanatgemische |
| MX345165B (es) | 2012-03-08 | 2017-01-19 | Hercules Inc | Supresion de viscosidad de espesantes asociativos usando organofosfatos. |
| EP2841047B1 (en) | 2012-04-24 | 2024-08-21 | L'oreal | Dyeing process using a mixture comprising a thickening polymer, obtained from an aerosol device, and device therefor |
| FR3044879B1 (fr) | 2015-12-14 | 2018-01-19 | L'oreal | Dispositif de distribution d'un produit de coloration et/ou d'eclaircissement des fibres keratiniques comprenant un polymere associatif |
| WO2024200254A1 (en) | 2023-03-24 | 2024-10-03 | Byk-Chemie Gmbh | Composition comprising an associative thickener |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1770068C3 (de) * | 1968-03-27 | 1981-01-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanen Bayer AG, 5090 Leverkusen |
| BE758703A (fr) * | 1969-11-10 | 1971-05-10 | Ciba Geigy | Procede servant a rendre la laine infeutrable |
| US4108816A (en) * | 1975-08-22 | 1978-08-22 | Mobil Oil Corporation | Cross-linkable emulsifying agents and aqueous emulsions containing the same |
| US4093579A (en) * | 1977-02-11 | 1978-06-06 | Formica Corporation | Low pressure melamine resins containing an ethylene glycol and an elastomer |
| US4228055A (en) * | 1978-09-06 | 1980-10-14 | Ppg Industries, Inc. | Aqueous coating compositions containing flatting agents and low molecular weight polyethers |
| US4229400A (en) * | 1978-09-18 | 1980-10-21 | Fiberite Corporation | Mold component comprising a mat impregnated with a reaction product of an aminoplast resin and a polyalkylene glycol |
| US4477618A (en) * | 1982-09-29 | 1984-10-16 | Ppg Industries, Inc. | Aminoplast curable coating compositions containing sulfonic acid esters as latent acid catalysts |
| US4525535A (en) * | 1984-10-24 | 1985-06-25 | Scm Corporation | Aqueous glycoluril thermosetting coating |
| US4833177A (en) * | 1987-12-03 | 1989-05-23 | Ppg Industries, Inc. | Method for preparing stably dispersed nonaqueous microparticle dispersion |
| US5084506A (en) * | 1987-12-03 | 1992-01-28 | Ppg Industries, Inc. | Stable nonaqueous microparticle dispersions prepared from aminoplast resins |
| US5071904A (en) * | 1989-05-30 | 1991-12-10 | Ppg Industries, Inc. | Waterborne coating compositions for automotive applications |
| US5276130A (en) * | 1991-10-30 | 1994-01-04 | Basf Corporation | Aminoplast resin or aminoplast resin precursor |
-
1995
- 1995-06-07 US US08/476,193 patent/US5914373A/en not_active Expired - Lifetime
-
1996
- 1996-06-07 EP EP96918343A patent/EP0830409B1/en not_active Expired - Lifetime
- 1996-06-07 WO PCT/US1996/009529 patent/WO1996040815A1/en not_active Ceased
- 1996-06-07 CA CA002221705A patent/CA2221705C/en not_active Expired - Lifetime
- 1996-06-07 AT AT96918343T patent/ATE231528T1/de not_active IP Right Cessation
- 1996-06-07 DE DE69625904T patent/DE69625904T2/de not_active Expired - Lifetime
- 1996-06-07 AU AU61030/96A patent/AU721667B2/en not_active Ceased
- 1996-06-07 JP JP50183297A patent/JP4180656B2/ja not_active Expired - Lifetime
-
1997
- 1997-12-05 MX MX9709619A patent/MX9709619A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2221705A1 (en) | 1996-12-19 |
| AU6103096A (en) | 1996-12-30 |
| DE69625904D1 (en) | 2003-02-27 |
| CA2221705C (en) | 2005-06-21 |
| US5914373A (en) | 1999-06-22 |
| DE69625904T2 (de) | 2003-12-24 |
| JP2001515525A (ja) | 2001-09-18 |
| ATE231528T1 (de) | 2003-02-15 |
| AU721667B2 (en) | 2000-07-13 |
| EP0830409B1 (en) | 2003-01-22 |
| EP0830409A1 (en) | 1998-03-25 |
| WO1996040815A1 (en) | 1996-12-19 |
| EP0830409A4 (enExample) | 1998-04-22 |
| MX9709619A (es) | 1998-10-31 |
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