JP6768667B2 - ハロゲンフリー難燃性感圧性接着剤及びテープ - Google Patents
ハロゲンフリー難燃性感圧性接着剤及びテープ Download PDFInfo
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- JP6768667B2 JP6768667B2 JP2017535021A JP2017535021A JP6768667B2 JP 6768667 B2 JP6768667 B2 JP 6768667B2 JP 2017535021 A JP2017535021 A JP 2017535021A JP 2017535021 A JP2017535021 A JP 2017535021A JP 6768667 B2 JP6768667 B2 JP 6768667B2
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- Prior art keywords
- acrylate
- monomer
- flame
- adhesive
- retardant
- Prior art date
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- 239000003063 flame retardant Substances 0.000 title claims description 71
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 64
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims description 105
- 230000001070 adhesive effect Effects 0.000 claims description 80
- 239000000853 adhesive Substances 0.000 claims description 72
- 229920006243 acrylic copolymer Polymers 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 229920001519 homopolymer Polymers 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 6
- -1 ethylacryloyloxymethylphenylphosphinate Chemical compound 0.000 claims description 6
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- HLEGSOPLIFMPDB-UHFFFAOYSA-N 1,1'-biphenyl ethyl prop-2-enoate Chemical compound CCOC(=O)C=C.c1ccc(cc1)-c1ccccc1 HLEGSOPLIFMPDB-UHFFFAOYSA-N 0.000 claims description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical group CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 2
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 claims description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 2
- HZLFQUWNZMMHQM-UHFFFAOYSA-N piperazin-1-ylmethanol Chemical compound OCN1CCNCC1 HZLFQUWNZMMHQM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 2
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims 1
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 239000000463 material Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 28
- 239000000203 mixture Substances 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 13
- 239000000470 constituent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000758 substrate 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000010076 replication Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- XKWFZGCWEYYGSK-UHFFFAOYSA-N 3,3,5,5-tetramethyl-2-methylidenehexanamide Chemical compound CC(C)(C)CC(C)(C)C(=C)C(N)=O XKWFZGCWEYYGSK-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920005479 Lucite® Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- OFUDYQRFPVQABP-UHFFFAOYSA-N [ethoxy(phenyl)phosphoryl]methyl prop-2-enoate Chemical compound C(C=C)(=O)OCP(OCC)(=O)C1=CC=CC=C1 OFUDYQRFPVQABP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 239000004359 castor oil Substances 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- YJSXLGKPMXKZJR-UHFFFAOYSA-N ethoxy-oxo-phenylphosphanium Chemical compound CCO[P+](=O)C1=CC=CC=C1 YJSXLGKPMXKZJR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/02—Homopolymers or copolymers of monomers containing phosphorus
-
- 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
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
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- 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
- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/02—Homopolymers or copolymers of monomers containing phosphorus
-
- 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
- C09J133/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
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- 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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
- C09J7/381—Pressure-sensitive adhesives [PSA] based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C09J7/385—Acrylic polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
-
- 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
- C09J2433/00—Presence of (meth)acrylic polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
「ハロゲンフリー」及び「非ハロゲン化」とは、本明細書内で同じ意味で用いられ、ハロゲン、すなわち、フッ素、塩素、臭素、ヨウ素、及びアスタチンの実質的な不在、例えば、微量又は無効な量を意味し、
「難燃性接着剤又はテープ」とは、工業規格UL510(Underwriters Laboratories Inc.,Eighth Edition)の燃焼性試験により規定された要件に合格可能な、本明細書内で提案される難燃性組成物を組み込んだ接着剤及びテープを意味し、
「ハロゲンフリー難燃性材料」及び「非ハロゲン化難燃性材料」とは、ハロゲンを含有しない難燃性材料(例えば、モノマー及びポリマー)を意味し、
「(メタ)アクリレート」及び「(メタ)アクリル」とは、メタクリレート又はアクリレート官能基を含む化合物を意味し、
「アクリルコポリマー」とは、その構成モノマーのうちの1つ以上が(メタ)アクリレート官能基を有するコポリマーを意味し、
「低Tgモノマー」とは、重合して少なくとも約10,000g/molの分子量を有するホモポリマーを形成したとき、0℃未満のガラス転移温度(Tg)を有するホモポリマーを生じるモノマーを意味し、
「高Tgモノマー」とは、重合して少なくとも約10,000g/molの分子量を有するホモポリマーを形成したとき、0℃を超えるガラス転移温度(Tg)を有するホモポリマーを生じるモノマーを意味し、
「再生可能資源」とは、100年の時間枠内で補充できる天然資源を意味する。資源は、自然に又は農業技術により補充され得る。再生可能資源は、典型的には、植物(すなわち、樹木を含む全ての陸上植物が挙げられる様々な光合成生物のうちのいずれか)、海藻及び藻などの原生生物、動物、並びに魚である。これらは、天然に生じる、ハイブリッドの又は遺伝子操作された生物であってもよい。形成するのに100年よりも長く掛かる原油、石炭及び泥炭などの天然資源は、再生可能資源であるとは考慮されない。
[式中、x及びyはそれぞれ整数を表し、xは1〜5の範囲(両端の値を含む)であることができ、yは0〜5の範囲(両端の値を含む)であることができる]により表すことが可能なアクリレート官能性モノマーである。各種実施形態では、x及びyの値は同一であっても又は互いに異なっていてもよい。更なる一態様では、ホスフィネート系モノマーは、
[式中、Etはエチル基を示し、Phはフェニル基を示す]によって表すことが可能なエチルアクリロイルオキシメチルフェニルホスフィネート(Ethyl Acryloyloxymethylphenylphosphinate、EAMPP)を含む。EAMPPは、実施例セクションにて更に詳細に説明される通りに合成できる。
別途明記されない限り、下記試薬は一般に、Sigma−Aldrich Co.(USA)及びAlfa Aesar(USA)などの化学物質製造業者から入手できる。
本発明の例示的な難燃性コポリマーは、表1に列挙した材料を使用して、当該技術分野において既知の方法を使用して調製した。
比較例及び例示的実施例の重合に使用される各モノマーの量を表2に示す。各実施例について、モノマーを表2に示す量で100gサイズのガラス瓶に添加し、酢酸エチル溶媒中で混合した。約0.4phr(全モノマーの百分率)の熱反応開始剤VAZO67を添加した。混合物全体に対する固形分含有量は約40重量%であった。本混合物を均一に混合した後、混合物は窒素(N2)ガスを使用して脱酸素した。瓶を密封し、ケージホルダに保管した。ケージホルダを、60℃でLaunder−Ometer内で水中に浸し、24時間回転させた。24時間後、瓶を室温まで冷却してから、1.2mil(0.0012インチ、0.030mm)厚のPETバッキングフィルムにコーティングした。コーティングしたフィルムを炉内で15分間70℃で乾燥させた。接着剤サンプルを、試験前に25℃、50%の一定相対湿度(RH)で一晩調湿した。
各実施例について、モノマーを表2に示す量で8オンスのジャーに添加した。約0.04phrのIRGACURE651を添加した。IRGACURE651を溶解した後、本混合物を脱酸素し、次いで、ブラックライト電球を用いて低出力(10ミリワット/平方センチメートル未満)UV−A紫外線に暴露した。その出力が主に、UV−Aスペクトル領域と呼ばれる約350ナノメートルをピーク放射とする約320〜390ナノメートルで発生するため、このような電球はUV−A電球と呼ばれる。本混合物を、約1800cpsのBrookfield粘度を有するプレ接着剤ポリマーシロップが形成されるまで暴露した。次いで、空気をシロップ中に導入した。
剥離接着強度
この試験は、180°の角度で基材からテープ物品を剥離するのに必要とされる力を測定する。試験は、ステンレス鋼基材を使用して、参照したASTM試験方法ASTM D3330/D3330M−04、「Standard Test Method for Peel Adhesion of Pressure−Sensitive Tape」に記載の手順を使用して、実施例で調製した調湿テープに対して行った。
本発明の接着テープの静的せん断強度も測定した。試験は、後述の変量を使用して、参照したASTM試験方法ASTM D−3654/D 3654M 06、「Standard Test Method for Sheer Adhesion of Pressure−Sensitive Tape」に記載の手順を使用して、実施例で調製した調湿テープに対して行った。テープの端部をステンレス鋼板に接着し、水平から90°の角度で吊るし、重りをテープの自由端部に取り付けた。室温(RT、23℃)又は高温(70℃)のいずれかで試験を行った。
サンプルをUL510燃焼性/焼け試験に従って試験した。各テープサンプルを鋼ロッドに巻き付け、15秒間裸火にさらした。試験に合格するには、火にさらしたとき、試験試料(典型的には発火する)上の炎が60秒未満で消えなくてはならない。試験は5回繰り返した。消火時間が60秒を超えた場合は試料が不良であるとみなした。結果は以下「合格」又は「不合格」と報告される。加えて、落下が観察されるべきではなく、またロッド頂部近くに置かれたクラフト紙の旗に火がついてはならない。試験についての更なる詳細は、米国イリノイ州ノースブルック(Northbrook)のアンダーライターズ・ラボラトリー(UnderwritersLaboratory)が発行するUL510標準の説明を参照のこと。
接着特性
ステンレス鋼(Stainless Steel、SS)基材に対する表2に記載のコポリマーの接着特性を、表3及び表4に示す。表3では、「lr」の破壊モードは、接着剤が凝集破壊し、基材に少量の残留物が残ったことを意味し、「cl」は、接着剤が接着破壊し、基材から離れ、裸眼では基材がきれいに見えることを意味する。
ホスフィネート含有コポリマー接着剤の難燃特性を下表5に示す。一部の実施例については、2つの複製を試験し、両方の複製の結果を表5に示す。
Claims (9)
- 低ガラス転移温度(Tg)モノマーを含む第1のモノマーと、
高Tgモノマーを含む第2のモノマーと、
ホスフィネート含有アクリレート官能性モノマーと、
を含むモノマーの重合により調製可能なアクリルコポリマーを含み、
前記低Tgモノマーは、重合して少なくとも10,000g/molの分子量を有するホモポリマーを形成したとき、0℃未満のTgを有するホモポリマーを生じるモノマーであり、
前記高Tgモノマーは、重合して少なくとも10,000g/molの分子量を有するホモポリマーを形成したとき、0℃を超えるTgを有するホモポリマーを生じるモノマーであり、
前記第1のモノマー及び前記第2のモノマーのうちの少なくとも1つが(メタ)アクリレートを含み、
前記ホスフィネート含有アクリレート官能性モノマーは、
[式中、xは1〜5の整数(両端の値を含む)であり、yは0〜5の整数(両端の値を含む)である]により表されるモノマーを含み、
前記アクリルコポリマーは、27重量%〜50重量%の前記ホスフィネート含有アクリレート官能性モノマー単位を含む、ハロゲンフリー難燃性接着剤。 - 前記アクリルコポリマーは、40重量%〜60重量%の前記低Tg(メタ)アクリルモノマー単位を含む、請求項1に記載の難燃性接着剤。
- 前記第1のモノマーは、n−ヘキシルアクリレート、n−ブチルアクリレート、イソブチルアクリレート、n−オクチルアクリレート、2−オクチルアクリレート、ラウリルアクリレート、イソオクチルアクリレート、2−エチルヘキシルアクリレート、ジメチルアミノエチルアクリレート、トリデシルアクリレート、2−エトキシエチルアクリレート、エトキシエトキシエチルアクリレート、2−ヒドロキシエチルアクリレート、4−ヒドロキシブチルアクリレート、2−メトキシエチルアクリレート、2−フェノキシエチルアクリレート、ウレタンアクリレート、シリコーンアクリレート及びこれらの組み合わせからなる群から選択される(メタ)アクリレート系モノマーを含む、請求項1又は2に記載の難燃性接着剤。
- 前記第2のモノマーは、2重量%〜10重量%の前記高Tg(メタ)アクリルモノマー単位を含む、請求項1〜3のいずれか一項に記載の難燃性接着剤。
- 前記第2のモノマーは、アクリル酸、イソボルニルアクリレート、メチルアクリレート、メチルメタクリレート、ブチルメタクリレート、t−ブチルアクリレート、ヘキサデシルアクリレート、エチルメタクリレート、ベンジルアクリレート、シクロヘキシルアクリレート、ビフェニルエチルアクリレート、N,N−ジメチルアミノエチルメタクリレート、ヒドロキシルエチルメタクリレート、脂肪族ウレタンアクリレート、芳香族ウレタンアクリレート、エポキシアクリレート、アクリルアミド、N,N−ジメチルアクリルアミド、N−ビニルピロリドン、酢酸ビニル、N−オクチルアクリルアミド、N−イソプロピルアクリルアミド、t−オクチルアクリルアミド、アクリルアミド、N−ビニルカプロラクタム及びこれらの組み合わせからなる群から選択されるモノマーを含む、請求項1〜4のいずれか一項に記載の難燃性接着剤。
- 前記ホスフィネート含有アクリレート官能性モノマーはエチルアクリロイルオキシメチルフェニルホスフィネート(EAMPP)を含む、請求項1に記載の難燃性接着剤。
- 前記アクリルコポリマーの前記モノマーはマクロモノマーを更に含む、請求項1〜6のいずれか一項に記載の難燃性接着剤。
- 前記マクロモノマーは、反応性ビニル基を有するポリ(メチルメタクリレート)マクロモノマーを含む、請求項7に記載の難燃性接着剤。
- 表裏となる2つの主表面を有する支持層と、前記支持層の少なくとも1つの前記主表面上に配置される請求項1に記載の接着剤と、を含むテープ。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462097703P | 2014-12-30 | 2014-12-30 | |
US62/097,703 | 2014-12-30 | ||
PCT/US2015/066809 WO2016109261A1 (en) | 2014-12-30 | 2015-12-18 | Halogen-free flame retardant pressure sensitive adhesive and tape |
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WO2018087035A1 (en) | 2016-11-08 | 2018-05-17 | Henkel Ag & Co. Kgaa | Pressure sensitive adhesive compositions |
CN110577803B (zh) | 2018-06-11 | 2021-11-26 | 3M创新有限公司 | 一种阻燃压敏胶粘合剂、阻燃压敏胶粘合片及其制备方法 |
CN109628029A (zh) * | 2018-12-29 | 2019-04-16 | 广东安利华新材料科技有限公司 | 一种无卤阻燃丙烯酸酯压敏胶、制备方法及使用方法 |
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JP3454544B2 (ja) | 1993-08-02 | 2003-10-06 | 日本化薬株式会社 | (メタ)アクリル酸エステル、その製造方法、それを用いた硬化性樹脂組成物およびその硬化物 |
US5851663A (en) | 1994-05-25 | 1998-12-22 | Minnesota Mining And Manufacturing Company | Flame retardant pressure-sensitive adhesives and tapes |
US6022914A (en) | 1995-11-27 | 2000-02-08 | 3M Innovative Properties Company | Pressure-sensitive adhesive composition and tapes |
JPH10110082A (ja) | 1996-10-08 | 1998-04-28 | Sekisui Chem Co Ltd | 難燃性光重合性組成物及びこれを用いた難燃性粘接着テープもしくはシート |
JPH10140094A (ja) | 1996-11-13 | 1998-05-26 | Sekisui Chem Co Ltd | 粘着テープ |
JPH1135588A (ja) | 1997-07-16 | 1999-02-09 | Nippon Chem Ind Co Ltd | アクリル基を有するホスフィン酸化合物およびその製造方法 |
JP2002226314A (ja) * | 2001-02-07 | 2002-08-14 | Kuraray Co Ltd | 無柱エナメル質用の接着性組成物 |
DE10322898A1 (de) | 2003-05-21 | 2004-12-16 | Tesa Ag | Flammfeste und Hitze-aktivierbare Haftklebemassen |
DE10359269B4 (de) * | 2003-12-17 | 2012-05-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung hydroxylgruppenhaltiger Phosphinate als und zur Herstellung von Flammschutzmitteln, die sich zur Einbindung in Polymerharze eignen oder als Bestandteil flammgeschützter Polymere, mit diesen Phosphinaten hergestellte neue Phosphinate mit organisch polymerisierbaren Gruppen, deren Herstellung sowie Verwendung in flammgeschützten Polymerharzen |
US7385020B2 (en) | 2006-10-13 | 2008-06-10 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
US20090104444A1 (en) | 2007-10-19 | 2009-04-23 | 3M Innovative Properties Company | Halogen-free flame retardant adhesive compositions and article containing same |
JP5602374B2 (ja) | 2009-03-30 | 2014-10-08 | リンテック株式会社 | 粘着剤組成物および粘着シート |
JP2010235846A (ja) | 2009-03-31 | 2010-10-21 | Lintec Corp | 感圧接着剤組成物、感圧接着剤層及び感圧接着性積層体 |
CN101760145B (zh) | 2009-12-22 | 2012-05-30 | 广州鹿山新材料股份有限公司 | 一种无卤阻燃热熔压敏胶带及其制备方法 |
CN101805567B (zh) | 2010-03-12 | 2012-10-31 | 北京化工大学 | 一种结合磷型阻燃丙烯酸酯压敏胶的制备方法 |
JP5996861B2 (ja) | 2010-12-30 | 2016-09-21 | チェイル インダストリーズ インコーポレイテッド | ダイシングダイボンディングフィルム用粘着剤組成物 |
KR20140012736A (ko) * | 2011-03-24 | 2014-02-03 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 난연성 접착제 |
US20120288693A1 (en) | 2011-04-12 | 2012-11-15 | Stanley Scott K | Flexible barrier packaging derived from renewable resources |
MX351640B (es) | 2011-10-31 | 2017-10-23 | Lubrizol Advanced Mat Inc | Polimeros retardantes de llama sin halogeno. |
KR20150100733A (ko) | 2012-12-20 | 2015-09-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 난연 접착제 |
TWI481651B (zh) | 2013-05-23 | 2015-04-21 | Chi Mei Corp | (甲基)丙烯酸酯系-苯乙烯系共聚物組成物及其成型品 |
US9187597B1 (en) | 2014-10-21 | 2015-11-17 | International Business Machines Corporation | Flame-retardant polylactic acid (PLA) by grafting through of phosphorus-containing polymers directly to PLA backbone |
WO2016109262A1 (en) | 2014-12-30 | 2016-07-07 | 3M Innovative Properties Company | Halogen-free flame retardant pressure sensitive adhesive and tape |
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MX2017008298A (es) | 2017-10-02 |
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JP2018506614A (ja) | 2018-03-08 |
TW201631094A (zh) | 2016-09-01 |
EP3240849B1 (en) | 2024-08-21 |
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US10526515B2 (en) | 2020-01-07 |
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