TW393506B - Improved crosslinkable surface coatings and process of preparation - Google Patents
Improved crosslinkable surface coatings and process of preparation Download PDFInfo
- Publication number
- TW393506B TW393506B TW087108414A TW87108414A TW393506B TW 393506 B TW393506 B TW 393506B TW 087108414 A TW087108414 A TW 087108414A TW 87108414 A TW87108414 A TW 87108414A TW 393506 B TW393506 B TW 393506B
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- Prior art keywords
- acid
- item
- patent application
- phenyl
- polymer
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 42
- 238000000576 coating method Methods 0.000 title description 20
- 238000002360 preparation method Methods 0.000 title description 10
- 230000008569 process Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 150000001412 amines Chemical class 0.000 claims abstract description 91
- 239000000178 monomer Substances 0.000 claims abstract description 75
- 238000009472 formulation Methods 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
- 239000004816 latex Substances 0.000 claims abstract description 41
- 229920000126 latex Polymers 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 150000002081 enamines Chemical group 0.000 claims abstract description 26
- 239000004615 ingredient Substances 0.000 claims abstract description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims description 182
- -1 hydroxy, phenyl Chemical group 0.000 claims description 79
- 239000000839 emulsion Substances 0.000 claims description 49
- 239000002245 particle Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 29
- 238000012644 addition polymerization Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000004132 cross linking Methods 0.000 claims description 20
- 239000003999 initiator Substances 0.000 claims description 20
- 239000008365 aqueous carrier Substances 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 17
- 230000002079 cooperative effect Effects 0.000 claims description 17
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 16
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 15
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 239000001530 fumaric acid Substances 0.000 claims description 7
- 235000015170 shellfish Nutrition 0.000 claims description 7
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- XTBMQKZEIICCCS-UHFFFAOYSA-N hexane-1,5-diamine Chemical compound CC(N)CCCCN XTBMQKZEIICCCS-UHFFFAOYSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 4
- CFGGNXFNDNQZKD-UHFFFAOYSA-N 2-(9H-fluoren-1-yl)prop-2-enoic acid Chemical compound C1C2=CC=CC=C2C2=C1C(C(=C)C(=O)O)=CC=C2 CFGGNXFNDNQZKD-UHFFFAOYSA-N 0.000 claims description 4
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 3
- 101100258315 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-1 gene Proteins 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 210000004080 milk Anatomy 0.000 claims description 3
- 238000007639 printing Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- JMLPVHXESHXUSV-UHFFFAOYSA-N dodecane-1,1-diamine Chemical compound CCCCCCCCCCCC(N)N JMLPVHXESHXUSV-UHFFFAOYSA-N 0.000 claims description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 210000003127 knee Anatomy 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
- 239000008267 milk Substances 0.000 claims description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 6
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 claims 5
- 125000000732 arylene group Chemical group 0.000 claims 3
- 150000004985 diamines Chemical class 0.000 claims 3
- 238000004898 kneading Methods 0.000 claims 3
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 claims 3
- 229920003169 water-soluble polymer Polymers 0.000 claims 3
- 150000001336 alkenes Chemical class 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims 2
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- DNIDAYOSPDNUKP-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C=CC=2C=CC=CC=2)=C1N DNIDAYOSPDNUKP-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 229910052778 Plutonium Inorganic materials 0.000 claims 1
- UTKBLLDLHPDWDU-TYYBGVCCSA-N acetic acid;(e)-but-2-enedioic acid Chemical compound CC(O)=O.OC(=O)\C=C\C(O)=O UTKBLLDLHPDWDU-TYYBGVCCSA-N 0.000 claims 1
- QLVHFTGKDGTJDH-UHFFFAOYSA-N acetic acid;ethenyl acetate Chemical compound CC(O)=O.CC(=O)OC=C QLVHFTGKDGTJDH-UHFFFAOYSA-N 0.000 claims 1
- WRVRNZNDLRUXSW-UHFFFAOYSA-N acetic acid;prop-2-enoic acid Chemical compound CC(O)=O.OC(=O)C=C WRVRNZNDLRUXSW-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 229910052786 argon Inorganic materials 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 239000000123 paper Substances 0.000 description 12
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
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- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical compound C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 2
- POIHBQZRXFDOPO-UHFFFAOYSA-N 1,2-bis(ethenyl)-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(C=C)C(C=C)=C3CC2=C1 POIHBQZRXFDOPO-UHFFFAOYSA-N 0.000 description 2
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- ZOZNCAMOIPYYIK-UHFFFAOYSA-N 1-aminoethylideneazanium;acetate Chemical class CC(N)=N.CC(O)=O ZOZNCAMOIPYYIK-UHFFFAOYSA-N 0.000 description 2
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- AIAMDEVDYXNNEU-UHFFFAOYSA-N 6-methylheptyl propanoate Chemical compound CCC(=O)OCCCCCC(C)C AIAMDEVDYXNNEU-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical group CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011850 water-based material Substances 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/866,217 US6090882A (en) | 1997-05-30 | 1997-05-30 | Crosslinkable surface coatings and process of preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW393506B true TW393506B (en) | 2000-06-11 |
Family
ID=25347176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087108414A TW393506B (en) | 1997-05-30 | 1998-06-02 | Improved crosslinkable surface coatings and process of preparation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6090882A (enExample) |
| EP (1) | EP0986611B1 (enExample) |
| JP (1) | JP2002501568A (enExample) |
| KR (1) | KR100521291B1 (enExample) |
| CN (1) | CN1140576C (enExample) |
| AR (1) | AR012895A1 (enExample) |
| AT (1) | ATE287926T1 (enExample) |
| AU (1) | AU733823B2 (enExample) |
| BR (1) | BR9810237A (enExample) |
| CA (1) | CA2291028A1 (enExample) |
| DE (1) | DE69828785T2 (enExample) |
| DK (1) | DK0986611T3 (enExample) |
| ES (1) | ES2236907T3 (enExample) |
| NZ (1) | NZ501255A (enExample) |
| TW (1) | TW393506B (enExample) |
| WO (1) | WO1998054256A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6417267B1 (en) * | 1996-05-28 | 2002-07-09 | Eastman Chemical Company | Adhesive compositions containing stable amino-containing polymer latex blends |
| US6660801B1 (en) | 2000-04-20 | 2003-12-09 | Rohm And Haas Company | Coating composition with improved adhesion to friable surface |
| EP1050561B1 (en) * | 1999-05-07 | 2005-07-06 | Rohm And Haas Company | Aqueous Coating composition |
| US7614197B2 (en) * | 1999-11-08 | 2009-11-10 | Premark Rwp Holdings, Inc. | Laminate flooring |
| GB0015245D0 (en) * | 2000-06-22 | 2000-08-16 | Avecia Ltd | Composition and process |
| FR2819520B1 (fr) * | 2001-01-18 | 2004-10-22 | Atofina | Application des latex porteurs de fonction acide a l'impregnation de substrat poreux |
| AU2002301310B2 (en) | 2001-10-17 | 2007-12-20 | Rohm And Haas Company | Polymer composition |
| US20040094236A1 (en) * | 2002-11-14 | 2004-05-20 | Crown Technology, Inc. | Methods for passivating stainless steel |
| US20050131176A1 (en) * | 2003-12-10 | 2005-06-16 | Cheng-Le Zhao | Process for production of polymer dispersions containing an acetoacetate moiety |
| GB0413630D0 (en) * | 2004-06-18 | 2004-07-21 | Avecia Ltd | Process |
| US9624342B2 (en) * | 2008-02-06 | 2017-04-18 | Valspar Sourcing, Inc. | Process for manufacturing medium and high molecular weight polyesters |
| US20090198004A1 (en) * | 2008-02-06 | 2009-08-06 | Valspar Sourcing, Inc. | Process for manufacturing high molecular weight polyesters |
| US8809446B2 (en) * | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Substituted 3-oxopentanoates and their uses in coating compositions |
| US9029451B2 (en) | 2010-12-15 | 2015-05-12 | Eastman Chemical Company | Waterborne coating compositions that include 2,2,4-trimethyl-3-oxopentanoate esters as reactive coalescents |
| US8809447B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
| TR201904462T4 (tr) * | 2011-03-30 | 2019-05-21 | Basf Se | Çok kademeli sulu polimer dispersiyonlarının üretimi için metot ve bunların zeminlerin kaplanması için bağ maddesi olarak kullanımı. |
| US11535762B2 (en) * | 2012-09-18 | 2022-12-27 | Ennis Flint | Fast drying aqueous amine free coating composition(s) |
| WO2014111292A1 (en) | 2013-01-18 | 2014-07-24 | Basf Se | Acrylic dispersion-based coating compositions |
| EP4077405A1 (en) * | 2019-12-20 | 2022-10-26 | Basf Se | Combination of crosslinkers to improve coating properties |
| CN116589641B (zh) * | 2023-06-19 | 2024-07-19 | 山东诺尔生物科技有限公司 | 一种聚丙烯酰胺类微球乳液及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0492847B2 (en) * | 1990-12-21 | 2002-11-20 | Rohm And Haas Company | Air curing polymer composition |
| US5391624A (en) * | 1992-02-10 | 1995-02-21 | S. C. Johnson & Son, Inc. | Thermosettable compositions |
| US5362816A (en) * | 1992-06-04 | 1994-11-08 | Rohm And Haas Company | High cohesive strength pressure-sensitive adhesives incorporating acetoacetate |
| US5270380A (en) * | 1992-10-13 | 1993-12-14 | Rohm And Haas Company | Method for extending the open time of an aqueous coating composition |
| US5534310A (en) * | 1994-08-17 | 1996-07-09 | Rohm And Haas Company | Method of improving adhesive of durable coatings on weathered substrates |
| US5872297A (en) * | 1995-08-24 | 1999-02-16 | S. C. Johnson Commercial Markets, Inc. | Ethylenically-unsaturated 1,3-diketoamide functional compounds |
| US5672379A (en) * | 1995-09-22 | 1997-09-30 | Rohm And Haas Company | Method of producing wear resistant traffic markings |
| US5756573A (en) * | 1995-10-05 | 1998-05-26 | Sc Johnson Commerical Markets, Inc. | Seed polymerized latex polymer having a gradient polymeric morphology and process for preparing the same |
| AU742196B2 (en) * | 1997-01-18 | 2001-12-20 | Rohm And Haas Company | Coating compositions |
-
1997
- 1997-05-30 US US08/866,217 patent/US6090882A/en not_active Expired - Lifetime
-
1998
- 1998-05-28 AT AT98924952T patent/ATE287926T1/de not_active IP Right Cessation
- 1998-05-28 CA CA002291028A patent/CA2291028A1/en not_active Abandoned
- 1998-05-28 NZ NZ501255A patent/NZ501255A/xx unknown
- 1998-05-28 WO PCT/US1998/010877 patent/WO1998054256A1/en not_active Ceased
- 1998-05-28 EP EP98924952A patent/EP0986611B1/en not_active Revoked
- 1998-05-28 DK DK98924952T patent/DK0986611T3/da active
- 1998-05-28 AU AU77006/98A patent/AU733823B2/en not_active Ceased
- 1998-05-28 JP JP50090599A patent/JP2002501568A/ja not_active Ceased
- 1998-05-28 ES ES98924952T patent/ES2236907T3/es not_active Expired - Lifetime
- 1998-05-28 CN CNB988063654A patent/CN1140576C/zh not_active Expired - Fee Related
- 1998-05-28 BR BR9810237-0A patent/BR9810237A/pt not_active Application Discontinuation
- 1998-05-28 DE DE69828785T patent/DE69828785T2/de not_active Revoked
- 1998-05-28 KR KR10-1999-7011180A patent/KR100521291B1/ko not_active Expired - Fee Related
- 1998-06-01 AR ARP980102557A patent/AR012895A1/es unknown
- 1998-06-02 TW TW087108414A patent/TW393506B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1264403A (zh) | 2000-08-23 |
| ATE287926T1 (de) | 2005-02-15 |
| WO1998054256A1 (en) | 1998-12-03 |
| DE69828785T2 (de) | 2006-01-05 |
| JP2002501568A (ja) | 2002-01-15 |
| EP0986611B1 (en) | 2005-01-26 |
| US6090882A (en) | 2000-07-18 |
| AU7700698A (en) | 1998-12-30 |
| CA2291028A1 (en) | 1998-12-03 |
| EP0986611A1 (en) | 2000-03-22 |
| DK0986611T3 (da) | 2005-06-06 |
| AU733823B2 (en) | 2001-05-24 |
| MX9911054A (enExample) | 2000-04-30 |
| KR100521291B1 (ko) | 2005-10-17 |
| NZ501255A (en) | 2002-09-27 |
| DE69828785D1 (de) | 2005-03-03 |
| ES2236907T3 (es) | 2005-07-16 |
| BR9810237A (pt) | 2001-11-20 |
| CN1140576C (zh) | 2004-03-03 |
| AR012895A1 (es) | 2000-11-22 |
| KR20010013194A (ko) | 2001-02-26 |
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Legal Events
| Date | Code | Title | Description |
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| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |