JP4968763B2 - 安定なアミノ含有ポリマーラテックスブレンドを含む接着剤組成物 - Google Patents
安定なアミノ含有ポリマーラテックスブレンドを含む接着剤組成物 Download PDFInfo
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- JP4968763B2 JP4968763B2 JP2001587072A JP2001587072A JP4968763B2 JP 4968763 B2 JP4968763 B2 JP 4968763B2 JP 2001587072 A JP2001587072 A JP 2001587072A JP 2001587072 A JP2001587072 A JP 2001587072A JP 4968763 B2 JP4968763 B2 JP 4968763B2
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- JP
- Japan
- Prior art keywords
- water
- acetoacetoxy
- aqueous
- latex
- functional polymer
- 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 - Fee Related
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- 239000004816 latex Substances 0.000 title claims abstract description 178
- 229920000126 latex Polymers 0.000 title claims abstract description 178
- 239000000203 mixture Substances 0.000 title claims abstract description 152
- 229920000642 polymer Polymers 0.000 title claims abstract description 130
- 239000000853 adhesive Substances 0.000 title claims abstract description 100
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 219
- 229920001002 functional polymer Polymers 0.000 claims abstract description 161
- 239000002245 particle Substances 0.000 claims abstract description 137
- 150000002081 enamines Chemical class 0.000 claims abstract description 39
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 26
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- -1 acetoacetoxy Chemical group 0.000 claims description 204
- 239000000178 monomer Substances 0.000 claims description 71
- 229920002554 vinyl polymer Polymers 0.000 claims description 40
- 239000004094 surface-active agent Substances 0.000 claims description 39
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 38
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 17
- 230000009477 glass transition Effects 0.000 claims description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001240 enamine group Chemical group 0.000 claims description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 239000004743 Polypropylene Substances 0.000 claims description 9
- 229920000058 polyacrylate Polymers 0.000 claims description 9
- 229920001155 polypropylene Polymers 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 7
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000010030 laminating Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 229920000573 polyethylene Polymers 0.000 claims description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 6
- 239000004800 polyvinyl chloride Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000003475 lamination Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YHSYGCXKWUUKIK-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C=C YHSYGCXKWUUKIK-UHFFFAOYSA-N 0.000 claims description 3
- FJKZPONBPMKPLO-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC(=O)C=C FJKZPONBPMKPLO-UHFFFAOYSA-N 0.000 claims description 3
- PICTWXAWDCLLKO-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCCOC(=O)C=C PICTWXAWDCLLKO-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000839 emulsion Substances 0.000 abstract description 92
- 238000002360 preparation method Methods 0.000 abstract description 43
- 239000012939 laminating adhesive Substances 0.000 abstract description 12
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000009472 formulation Methods 0.000 abstract description 10
- 238000004132 cross linking Methods 0.000 abstract description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 102
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 86
- 239000000243 solution Substances 0.000 description 79
- 239000003999 initiator Substances 0.000 description 73
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 61
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 48
- 229920002873 Polyethylenimine Polymers 0.000 description 46
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 43
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 42
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 42
- 238000010926 purge Methods 0.000 description 42
- 239000000463 material Substances 0.000 description 37
- 239000007787 solid Substances 0.000 description 36
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 32
- YXLIYGUJLJFLJH-UHFFFAOYSA-L disodium;4-(octadecylamino)-4-oxo-2-sulfonatobutanoate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCCNC(=O)CC(C([O-])=O)S([O-])(=O)=O YXLIYGUJLJFLJH-UHFFFAOYSA-L 0.000 description 28
- 238000006116 polymerization reaction Methods 0.000 description 27
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 22
- 229910000029 sodium carbonate Inorganic materials 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 15
- 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 15
- 239000000758 substrate Substances 0.000 description 15
- 101100030424 Bombyx mori PPAE gene Proteins 0.000 description 14
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000000872 buffer Substances 0.000 description 10
- 239000008199 coating composition Substances 0.000 description 10
- 238000007720 emulsion polymerization reaction Methods 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 8
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000002736 nonionic surfactant Substances 0.000 description 8
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 7
- 238000002835 absorbance Methods 0.000 description 7
- 239000001099 ammonium carbonate Substances 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 239000003945 anionic surfactant Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000008034 disappearance Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 150000003141 primary amines Chemical class 0.000 description 7
- 238000005096 rolling process Methods 0.000 description 7
- 150000003335 secondary amines Chemical class 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 230000008961 swelling Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 6
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 6
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 235000010350 erythorbic acid Nutrition 0.000 description 6
- 229940026239 isoascorbic acid Drugs 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 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 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 240000007651 Rubus glaucus Species 0.000 description 4
- 235000011034 Rubus glaucus Nutrition 0.000 description 4
- 235000009122 Rubus idaeus Nutrition 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 4
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- SUODCTNNAKSRHB-UHFFFAOYSA-N 2-ethylhexyl 3-sulfanylpropanoate Chemical compound CCCCC(CC)COC(=O)CCS SUODCTNNAKSRHB-UHFFFAOYSA-N 0.000 description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 239000004594 Masterbatch (MB) Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012943 hotmelt Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
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- 150000003254 radicals Chemical class 0.000 description 3
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- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000011115 styrene butadiene Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 150000003512 tertiary amines Chemical group 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 2
- FKOZPUORKCHONH-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid Chemical compound CC(C)CS(O)(=O)=O FKOZPUORKCHONH-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- AIUMIDJSSGINNR-UHFFFAOYSA-N 4-methoxybut-1-enyl 2-methylprop-2-enoate Chemical compound COCCC=COC(=O)C(C)=C AIUMIDJSSGINNR-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—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
- C09J133/062—Copolymers with monomers not covered by C09J133/06
-
- 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
- C08F220/283—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/576,639 US6417267B1 (en) | 1996-05-28 | 2000-05-24 | Adhesive compositions containing stable amino-containing polymer latex blends |
| US09/576,639 | 2000-05-24 | ||
| PCT/US2001/016242 WO2001090272A2 (en) | 2000-05-24 | 2001-05-22 | Adhesive compositions containing stable amino-containing polymer latex blends |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003535163A JP2003535163A (ja) | 2003-11-25 |
| JP2003535163A5 JP2003535163A5 (https=) | 2008-06-26 |
| JP4968763B2 true JP4968763B2 (ja) | 2012-07-04 |
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| JP2001587072A Expired - Fee Related JP4968763B2 (ja) | 2000-05-24 | 2001-05-22 | 安定なアミノ含有ポリマーラテックスブレンドを含む接着剤組成物 |
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| US (1) | US6417267B1 (https=) |
| EP (1) | EP1290101B1 (https=) |
| JP (1) | JP4968763B2 (https=) |
| CN (1) | CN1443229A (https=) |
| AT (1) | ATE280207T1 (https=) |
| BR (1) | BR0111096A (https=) |
| DE (1) | DE60106608T2 (https=) |
| MX (1) | MXPA02011518A (https=) |
| WO (1) | WO2001090272A2 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10148731A1 (de) * | 2001-10-02 | 2003-04-17 | Tesa Ag | Haftklebrige Polyacrylate |
| AU2002301310B2 (en) * | 2001-10-17 | 2007-12-20 | Rohm And Haas Company | Polymer composition |
| WO2004112760A1 (ja) | 2003-06-24 | 2004-12-29 | Saitama Daiichi Pharmaceutical Co., Ltd. | 医療用経皮吸収テープ製剤用非水性粘着剤並びに医療用経皮吸収テープ製剤およびその製造法 |
| WO2007059516A1 (en) | 2005-11-15 | 2007-05-24 | Valspar Sourcing, Inc. | Crush resistant latex topcoat composition for fiber cement substrates |
| CA2636435C (en) * | 2006-01-31 | 2013-10-22 | Valspar Sourcing, Inc. | Coating system for cement composite articles |
| US9783622B2 (en) | 2006-01-31 | 2017-10-10 | Axalta Coating Systems Ip Co., Llc | Coating system for cement composite articles |
| US20070219307A1 (en) * | 2006-03-17 | 2007-09-20 | Yong Yang | Emulsion polymer blend coating compositions and methods for increasing chalky substrate adhesion |
| DE602007012700D1 (de) | 2006-06-02 | 2011-04-07 | Valspar Sourcing Inc | Wässrige hochleistungsbeschichtungszusammensetzungen |
| ES2716987T3 (es) | 2006-07-07 | 2019-06-18 | Swimc Llc | Sistemas de recubrimiento para artículos composite de cemento |
| MX2008002220A (es) | 2007-02-16 | 2009-02-25 | Valspar Sourcing Inc | Tratamiento para articulos compuestos de cemento. |
| DE102008032571A1 (de) | 2008-07-11 | 2010-01-14 | Tesa Se | Haftklebemassen und Verfahren zu deren Herstellung |
| MX2011001736A (es) | 2008-08-15 | 2011-05-10 | Valspar Sourcing Inc | Composicion de recubrimiento de sustrato cementoso de auto-grabado. |
| AU2009316285A1 (en) | 2008-11-24 | 2010-05-27 | Valspar Sourcing, Inc. | Coating system for cement composite articles |
| US8338515B1 (en) | 2009-05-14 | 2012-12-25 | DT-SP IP Holding LLC | Silicone-modified tackifier and use thereof in pressure sensitive adhesive compositions and laminates with improved guillotinability |
| WO2012050872A1 (en) * | 2010-09-28 | 2012-04-19 | Industrias Negromex, S.A. De C.V. | Pressure sensitive adhesive soluble in acetone |
| US8809447B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
| 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 |
| US20130084437A1 (en) * | 2011-09-29 | 2013-04-04 | Dennis E. McGee | Film Coatings Based on Polyalkylimine Condensation Polymers |
| CN102504090A (zh) * | 2011-10-12 | 2012-06-20 | 辽宁恒星精细化工有限公司 | 一种纺织品涂料印花用粘合剂及其制备方法 |
| EP2945994B1 (en) | 2013-01-18 | 2018-07-11 | Basf Se | Acrylic dispersion-based coating compositions |
| TWI713498B (zh) | 2015-03-24 | 2020-12-21 | 美商羅門哈斯公司 | 核-殼水性乳膠 |
| EP3085713A1 (en) * | 2015-04-21 | 2016-10-26 | Rohm And Haas Company | Co2 abating latex coating composition |
| EP3434701A1 (en) * | 2017-07-25 | 2019-01-30 | Arkema France | Stable aqueous polymer dispersions |
| CN109294453A (zh) * | 2018-10-12 | 2019-02-01 | 扬州中涂科技集团有限公司 | 一种瓷砖背涂胶乳液 |
| US12522756B2 (en) | 2018-12-28 | 2026-01-13 | Saint-Gobain Performance Plastics Corporation | Adhesive composition and methods of forming the same |
| EP3902887A4 (en) | 2018-12-28 | 2022-11-02 | Saint-Gobain Performance Plastics Corporation | ADHESIVE COMPOSITIONS AND METHODS OF MAKING THEREOF |
| EP4031510A1 (en) * | 2019-09-20 | 2022-07-27 | Omnova Solutions Inc | Green compositions for making refractory ceramic |
| US20240150630A1 (en) * | 2021-03-23 | 2024-05-09 | Celanese International Corporation | Adhesives for film lamination and products made therefrom |
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| US3113038A (en) | 1961-01-19 | 1963-12-03 | Interchem Corp | Nonwoven fabric coating containing propylenimine-cross linking agent for carboxyl containing acrylic polymer |
| US3356627A (en) | 1963-06-17 | 1967-12-05 | Rohm & Haas | Aqueous blends of two water-insoluble polymers, one of which has 1 to 15% of a monomer containing an alcoholic hydroxyl, amino, amido or ureido group |
| US3290417A (en) | 1965-06-01 | 1966-12-06 | Pittsburgh Plate Glass Co | Thermosetting coating compositions modified with an alkylenimine |
| US3261796A (en) | 1964-07-01 | 1966-07-19 | Du Pont | Aqueous dispersion of vinyl addition polymer containing aminoester radicals |
| US3261797A (en) | 1964-10-28 | 1966-07-19 | Du Pont | Process for iminating polymeric latices |
| US3386939A (en) | 1964-11-27 | 1968-06-04 | Du Pont | Acrylic dispersions for wire enamels |
| NL134017C (https=) | 1965-10-29 | |||
| US3325443A (en) | 1966-01-07 | 1967-06-13 | Pittsburgh Plate Glass Co | Hydroxyalkyl-substituted alkylenimine modified alkyl methacrylate resins |
| US3483149A (en) | 1966-05-19 | 1969-12-09 | Inter Chem Corp | Novel coating composition |
| US3551357A (en) | 1967-06-14 | 1970-12-29 | Bayer Ag | Process for the production of crosslinked acrylated copolymers |
| DE1644988B2 (de) | 1967-06-28 | 1973-09-06 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Ueberzugs- und verklebungsmittel auf basis von gemischen von acetylacetatgruppen aufweisenden polymerisaten aethylenisch ungesaettigterverbindungen, acetoacetaten mehrwertiger metalle und verduennungsmittel |
| US3553116A (en) | 1967-08-30 | 1971-01-05 | Du Pont | Mechanically and freeze-thaw stable aqueous emulsions of iminated carboxylic vinyl acetate/ethylene copolymers and process for preparing same |
| US3639327A (en) | 1968-05-27 | 1972-02-01 | Johnson & Johnson | Adhesive composition |
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-
2000
- 2000-05-24 US US09/576,639 patent/US6417267B1/en not_active Expired - Lifetime
-
2001
- 2001-05-22 DE DE60106608T patent/DE60106608T2/de not_active Expired - Lifetime
- 2001-05-22 EP EP01941515A patent/EP1290101B1/en not_active Expired - Lifetime
- 2001-05-22 MX MXPA02011518A patent/MXPA02011518A/es not_active Application Discontinuation
- 2001-05-22 CN CN01813167A patent/CN1443229A/zh active Pending
- 2001-05-22 AT AT01941515T patent/ATE280207T1/de not_active IP Right Cessation
- 2001-05-22 BR BR0111096-9A patent/BR0111096A/pt not_active Application Discontinuation
- 2001-05-22 JP JP2001587072A patent/JP4968763B2/ja not_active Expired - Fee Related
- 2001-05-22 WO PCT/US2001/016242 patent/WO2001090272A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA02011518A (es) | 2004-09-06 |
| DE60106608D1 (de) | 2004-11-25 |
| DE60106608T2 (de) | 2006-02-02 |
| WO2001090272A2 (en) | 2001-11-29 |
| CN1443229A (zh) | 2003-09-17 |
| JP2003535163A (ja) | 2003-11-25 |
| WO2001090272A3 (en) | 2002-04-11 |
| EP1290101A2 (en) | 2003-03-12 |
| US6417267B1 (en) | 2002-07-09 |
| BR0111096A (pt) | 2003-04-08 |
| EP1290101B1 (en) | 2004-10-20 |
| ATE280207T1 (de) | 2004-11-15 |
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