JP2012149183A - Flame-retardant adhesive agent and flame-retardant adhesive tape - Google Patents
Flame-retardant adhesive agent and flame-retardant adhesive tape Download PDFInfo
- Publication number
- JP2012149183A JP2012149183A JP2011009357A JP2011009357A JP2012149183A JP 2012149183 A JP2012149183 A JP 2012149183A JP 2011009357 A JP2011009357 A JP 2011009357A JP 2011009357 A JP2011009357 A JP 2011009357A JP 2012149183 A JP2012149183 A JP 2012149183A
- Authority
- JP
- Japan
- Prior art keywords
- flame retardant
- acrylic polymer
- parts
- flame
- sensitive adhesive
- 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.)
- Granted
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 115
- 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 abstract description 109
- 239000000853 adhesive Substances 0.000 title claims abstract description 18
- 239000002390 adhesive tape Substances 0.000 title abstract description 29
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 75
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 239000002245 particle Substances 0.000 claims abstract description 18
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 7
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 50
- 230000001070 adhesive effect Effects 0.000 claims description 16
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 239000010410 layer Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052787 antimony Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052732 germanium Inorganic materials 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- 230000007774 longterm Effects 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 5
- 239000006185 dispersion Substances 0.000 description 80
- 238000000034 method Methods 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 43
- 238000003786 synthesis reaction Methods 0.000 description 43
- 239000000203 mixture Substances 0.000 description 30
- 239000007788 liquid Substances 0.000 description 21
- -1 phosphorus compound Chemical class 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 239000004114 Ammonium polyphosphate Substances 0.000 description 4
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 description 4
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 4
- 229920001276 ammonium polyphosphate Polymers 0.000 description 4
- 239000011162 core material Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical class C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ANALBGQGSOHBHD-UHFFFAOYSA-K CC(CP([O-])=O)(C)C.[Al+3].CC(CP([O-])=O)(C)C.CC(CP([O-])=O)(C)C Chemical compound CC(CP([O-])=O)(C)C.[Al+3].CC(CP([O-])=O)(C)C.CC(CP([O-])=O)(C)C ANALBGQGSOHBHD-UHFFFAOYSA-K 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
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- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- PMOVRVGWLWHABA-UHFFFAOYSA-J [Ti+4].CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O Chemical compound [Ti+4].CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O.CC(C)C(C)(C)P([O-])=O PMOVRVGWLWHABA-UHFFFAOYSA-J 0.000 description 1
- HZSAGZAJGQNWSD-UHFFFAOYSA-J [Ti+4].[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1 Chemical compound [Ti+4].[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1.[O-]P(=O)(c1ccccc1)c1ccccc1 HZSAGZAJGQNWSD-UHFFFAOYSA-J 0.000 description 1
- BBUVVWFDWAGLPU-UHFFFAOYSA-L [Zn++].CC(C)(C)P([O-])=O.CC(C)(C)P([O-])=O Chemical compound [Zn++].CC(C)(C)P([O-])=O.CC(C)(C)P([O-])=O BBUVVWFDWAGLPU-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- QNNHFEIZWVGBTM-UHFFFAOYSA-K aluminum;diphenylphosphinate Chemical compound [Al+3].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 QNNHFEIZWVGBTM-UHFFFAOYSA-K 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
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- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
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- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
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- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
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- 238000007607 die coating method Methods 0.000 description 1
- HFVKYLPSHXAMME-UHFFFAOYSA-J diethylphosphinate;titanium(4+) Chemical compound [Ti+4].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC HFVKYLPSHXAMME-UHFFFAOYSA-J 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
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- 238000001879 gelation Methods 0.000 description 1
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007759 kiss coating Methods 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 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 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 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
- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、優れた難燃性と粘着力を有する難燃性粘着剤及び難燃性粘着テープに関するものである。詳しくは、粘着性、長期保存性および難燃性に優れた粘着剤で、電気・電子部品や家電、建材などの各分野で難燃性が必要な部分の固定用に好適な粘着テープに関する。 The present invention relates to a flame retardant adhesive having excellent flame retardancy and adhesive strength, and a flame retardant adhesive tape. More specifically, the present invention relates to an adhesive tape excellent in adhesiveness, long-term storage and flame retardancy, and suitable for fixing a portion that requires flame retardance in various fields such as electric / electronic parts, home appliances, and building materials.
近年、電気・電子機器の高集積化、高性能化が進み、それに伴い内部の高温化や畜熱による発火の危険性が非常に高くなってきている。そのような危険を防止する必要性から、機器内の各種部品はもちろん、それらの接着用部材にも高度な難燃性が要求されるようになってきている。また、家電、建材などの各分野でも、プラスチック材料の難燃化について様々な研究が盛んに行われており、それらの固定に用いられる接着材料にも、当然ながら高い難燃性が要求されるようになってきている。 In recent years, electrical and electronic devices have been highly integrated and enhanced in performance, and accordingly, the risk of ignition due to high internal temperatures and livestock heat has become extremely high. Due to the necessity of preventing such danger, a high degree of flame retardancy has been required not only for various parts in equipment but also for their bonding members. In various fields such as home appliances and building materials, various studies have been actively conducted on the flame retardancy of plastic materials, and naturally, high flame retardancy is also required for adhesive materials used for fixing them. It has become like this.
粘着剤の難燃化手法については、ハロゲン系の難燃剤と酸化アンチモンとを併用する手法が知られている（特許文献１参照）。しかしながら、ハロゲン系の難燃剤は燃焼時に人体に毒性のあるハロゲン系ガスを発生することや、機器などを腐食せしめるという問題があった。このような観点から、ハロゲン系難燃剤を用いない難燃化方法の開発が求められるようになっている。 As a flame retardant method for the pressure-sensitive adhesive, a method in which a halogen-based flame retardant and antimony oxide are used in combination is known (see Patent Document 1). However, halogen-based flame retardants have problems in that they generate halogen-based gases that are toxic to the human body during combustion and corrode equipment. From such a viewpoint, development of a flame retardant method that does not use a halogen-based flame retardant has been demanded.
ハロゲン系難燃剤以外の難燃化手法としては、無機系難燃剤、窒素系難燃剤などが知られているが、これらの難燃剤は、ハロゲン系難燃剤よりも難燃効果が遙かに劣っている為、粘着剤中に大量に配合しなければならず、粘着力を大幅に低下させるという問題があった。 Inorganic flame retardants and nitrogen flame retardants are known as flame retardant methods other than halogen flame retardants, but these flame retardants are far inferior in flame retardant effect to halogen flame retardants. Therefore, it has to be blended in a large amount in the pressure-sensitive adhesive, and there is a problem that the adhesive strength is greatly reduced.
また、ハロゲン系難燃剤程の高い難燃性ではないが、比較的難燃効果が高いリン系化合物を用いることも知られている。中でも、ポリリン酸アンモニウム等の窒素元素を含有したリン系難燃剤と赤リンとの組み合わせが高い難燃性を示すことが知られているが（特許文献２参照）、赤リンを使用している為、焼却時に有害なホスフィンガスを発生したり、ポリリン酸アンモニウムの吸湿性のため、湿熱環境で十分な性能がでないという問題点があり、用途や難燃剤量が限られてしまう（非特許文献１参照）。 It is also known to use a phosphorus compound that is not as flame retardant as a halogen flame retardant, but has a relatively high flame retardant effect. Among them, it is known that a combination of a phosphorus flame retardant containing nitrogen element such as ammonium polyphosphate and red phosphorus exhibits high flame retardancy (see Patent Document 2), but red phosphorus is used. Therefore, there is a problem that harmful phosphine gas is generated during incineration and the hygroscopicity of ammonium polyphosphate does not provide sufficient performance in a moist heat environment, and the usage and amount of flame retardant are limited (Non-Patent Documents) 1).
前記窒素含有リン系化合物以外のリン系難燃剤として、リン酸エステル系難燃剤を用いることが知られているが、リン酸エステル系化合物の性状が液状の場合には、粘着剤層を可塑化して凝集力を低下させたり，粘着剤層表面に該難燃剤がブリードしたりするといった問題があり、又、リン酸エステル系難燃剤の性状が固体の場合には、粘着剤層表面に該難燃剤粒子が析出するという問題があった。 It is known to use a phosphate ester flame retardant as a phosphorus flame retardant other than the nitrogen-containing phosphorus compound, but when the property of the phosphate ester compound is liquid, the adhesive layer is plasticized. If the properties of the phosphoric acid ester flame retardant are solid, the cohesive force is reduced and the flame retardant bleeds on the surface of the pressure-sensitive adhesive layer. There was a problem that the fuel particles were deposited.
本発明は、上記のような従来技術における問題点を解決しようとするものであり、難燃性、粘着性および長期保存性に優れた粘着テープを得ることができる粘着剤、ならびに粘着テープを提供することを目的とする。 The present invention is intended to solve the above-described problems in the prior art, and provides an adhesive capable of obtaining an adhesive tape excellent in flame retardancy, adhesiveness and long-term storage, and an adhesive tape The purpose is to do.
本発明者らは、上記課題を解決するために鋭意検討した結果、特定のアクリル系粘着剤と、特定のホスフィン酸塩を配合すると、難燃性を持ち、粘着性、長期保存性に優れたアクリル粘着剤が得られることを見出した。 As a result of intensive studies to solve the above problems, the present inventors have blended a specific acrylic pressure-sensitive adhesive and a specific phosphinic acid salt, have flame retardancy, and are excellent in adhesiveness and long-term storage stability. It has been found that an acrylic pressure-sensitive adhesive can be obtained.
すなわち、第一の発明は、少なくともカルボキシル基含有モノマー（ａ）を０．１〜１５重量％用いてなるアクリル系ポリマー（Ａ）と、イソシアネート系硬化剤（Ｂ）と、下記一般式（１）で示されるホスフィン酸塩（Ｃ）とを含む難燃性粘着剤であって、
前記ホスフィン酸塩（Ｃ）を、アクリル系ポリマー（Ａ）１００重量部に対して、３０〜７０重量部含有し、
さらに前記ホスフィン酸塩（Ｃ）の平均粒子径が０．１μｍ以上〜２０μｍ以下であることを特徴とする難燃性粘着剤である。
一般式（１）
That is, the first invention is an acrylic polymer (A) comprising at least 0.1 to 15% by weight of a carboxyl group-containing monomer (a), an isocyanate curing agent (B), and the following general formula (1): A flame retardant adhesive comprising a phosphinic acid salt (C) represented by
The phosphinate (C) is contained in an amount of 30 to 70 parts by weight with respect to 100 parts by weight of the acrylic polymer (A).
Furthermore, the flame retardant pressure-sensitive adhesive is characterized in that the phosphinic acid salt (C) has an average particle size of 0.1 μm to 20 μm.
General formula (1)
(但し、式中Ｒ1、Ｒ2は同一かまたは異なり、直鎖状もしくは分岐状の炭素数１〜６のアルキル基、またはアリール基を示し、Ｍは、Ｍｇ、Ｃａ、Ａｌ、Ｓｂ、Ｓｎ、Ｇｅ、Ｔｉ、Ｚｎ、Ｆｅ、Ｚｒ、Ｃｅ、Ｂｉ、Ｓｒ、Ｍｎ、Ｌｉ、Ｎａ、Ｋから成る群より選択される少なくとも一種の金属を示し、ｍは、１〜４の整数である。)
第二の発明は、基材と請求項１記載の難燃性粘着剤から形成されてなる粘着剤層を有することを特徴とする難燃性粘着テープである。
(In the formula, R 1 and R 2 are the same or different and represent a linear or branched alkyl group having 1 to 6 carbon atoms or an aryl group, and M represents Mg, Ca, Al, Sb, Sn. , Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K represents at least one metal selected, and m is an integer of 1 to 4.
2nd invention is a flame-retardant adhesive tape characterized by having an adhesive layer formed from a base material and the flame-retardant adhesive of Claim 1.
本発明によって、従来のような難燃化方法における問題点を解決しようとするものであり、難燃性を持ち、粘着性に優れたアクリル粘着剤、ならびに、該粘着剤を用いた塗工物を提供することができる。 According to the present invention, an acrylic pressure-sensitive adhesive having flame retardancy and excellent adhesiveness, and a coated product using the pressure-sensitive adhesive, which is intended to solve the problems in the conventional flame-retarding method. Can be provided.
まず、本発明に用いるアクリル系ポリマー（Ａ）について説明する。 First, the acrylic polymer (A) used in the present invention will be described.
本発明に用いるアクリル系ポリマー（Ａ）は、カルボキシル基含有モノマー（ａ）と、カルボキシル基含有モノマー（ａ）以外のモノマーを共重合して得られる共重合体である。 The acrylic polymer (A) used in the present invention is a copolymer obtained by copolymerizing a carboxyl group-containing monomer (a) and a monomer other than the carboxyl group-containing monomer (a).
カルボキシル基含有モノマー（ａ）の具体例としては、（メタ）アクリル酸、β − カルボキシエチルアクリレート、イタコン酸、クロトン酸、フマル酸、無水フマル酸、マレイン酸、無水マレイン酸、マレイン酸ブチル等が挙げられるが、これに限定されるものではない。これらはモノマー１００重量％中０．１〜１５．０重量％、好ましくは０．３〜１０重量％、さらに好ましく１〜６重量％の割合で用いられる。 Specific examples of the carboxyl group-containing monomer (a) include (meth) acrylic acid, β-carboxyethyl acrylate, itaconic acid, crotonic acid, fumaric acid, fumaric anhydride, maleic acid, maleic anhydride, butyl maleate and the like. Although it is mentioned, it is not limited to this. These are used in a proportion of 0.1 to 15.0% by weight, preferably 0.3 to 10% by weight, more preferably 1 to 6% by weight in 100% by weight of the monomer.
ここで、カルボキシル基含有モノマー（ａ）の量が０．１重量部未満であると、得られるアクリル系ポリマーとホスフィン酸塩粒子の微細分散安定性が得られにくい。また、１５．０重量部以上であると、アクリル系ポリマーの合成が困難であったり、またイソシアネート系硬化剤（Ｂ）との反応でゲル化したり、また該粘着テープにおいて十分な接着力を得られにくい。 Here, when the amount of the carboxyl group-containing monomer (a) is less than 0.1 parts by weight, it is difficult to obtain the fine dispersion stability of the obtained acrylic polymer and phosphinate particles. Moreover, when it is 15.0 parts by weight or more, it is difficult to synthesize an acrylic polymer, or it is gelled by reaction with an isocyanate curing agent (B), and sufficient adhesive strength is obtained in the pressure-sensitive adhesive tape. It's hard to be done.
カルボキシル基含有モノマー（ａ）以外のモノマーは、(メタ)アルキルアクリレートモノマー（ｂ）、（ａ）または（ｂ）と共重合可能な分子内にカルボキシル基以外の極性基を有する共重合性モノマー（ｃ）（以下、モノマー（ｃ）ともいう）を挙げることができる。 The monomer other than the carboxyl group-containing monomer (a) is a copolymerizable monomer having a polar group other than a carboxyl group in a molecule copolymerizable with the (meth) alkyl acrylate monomer (b), (a) or (b) ( c) (hereinafter also referred to as monomer (c)).
(メタ)アルキルアクリレートモノマー（ｂ）の具体例としては、アクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸ブチル、アクリル酸イソブチル、アクリル酸イソアミル、アクリル酸ヘキシル、アクリル酸２−エチルヘキシル、アクリル酸オクチル、アクリル酸イソオクチル、アクリル酸イソノニル、アクリル酸イソデシル、アクリル酸ラウリル、エタクリル酸メチル、メタクリル酸ブチル、メタクリル酸ヘキシル、メタクリル酸２−エチルヘキシル、メタクリル酸イソデシル、メタクリル酸ラウリル等が挙げられる。 Specific examples of the (meth) alkyl acrylate monomer (b) include methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, isobutyl acrylate, isoamyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, acrylic Examples include octyl acid, isooctyl acrylate, isononyl acrylate, isodecyl acrylate, lauryl acrylate, methyl ethacrylate, butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, lauryl methacrylate, and the like.
モノマー（ｃ）は、例えば(メタ)アクリルアミド、置換アクリルアミド、Ｎ−ビニルピロリドン、Ｎ−ビニルカプロラクタム、(メタ)アクリロイルモルフォリン、(メタ)アクリルアミド等の窒素含有モノマー、２−ヒドロキシエチル(メタ)アクリレート、２−ヒドロキシプロピル(メタ)アクリレート、４−ヒドロキシブチル(メタ)アクリレート等の水酸基含有モノマーなどが挙げられるがこれに限定されるものではない。これら共重合性モノマー（ｂ）および（ｃ）は、モノマー混合物中８５．０〜９９．９重量部、好ましくは９０．０〜９９．７重量部、さらに好ましくは９４．０重量部〜９９．０重量部の割合で用いられる。 Monomer (c) is, for example, nitrogen-containing monomer such as (meth) acrylamide, substituted acrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, (meth) acryloylmorpholine, (meth) acrylamide, 2-hydroxyethyl (meth) acrylate , Hydroxyl group-containing monomers such as 2-hydroxypropyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate, but are not limited thereto. These copolymerizable monomers (b) and (c) are 85.0 to 99.9 parts by weight, preferably 90.0 to 99.7 parts by weight, more preferably 94.0 parts by weight to 99.99 parts by weight, in the monomer mixture. Used in a proportion of 0 parts by weight.
本発明で好ましく用いられるアクリル系ポリマー（Ａ）の重量平均分子量は、好ましくは３０万〜１２０万、より好ましくは４０万〜８０万、さらに好ましくは５０万〜７０万である。ここで、重量平均分子量は、ゲルパーミエーションクロマトグラフィー（ＧＰＣ）で測定したポリスチレン換算の値である。 The weight average molecular weight of the acrylic polymer (A) preferably used in the present invention is preferably 300,000 to 1,200,000, more preferably 400,000 to 800,000, and further preferably 500,000 to 700,000. Here, the weight average molecular weight is a value in terms of polystyrene measured by gel permeation chromatography (GPC).
次に、本発明に用いるイソシアネート系硬化剤（Ｂ）について説明する。 Next, the isocyanate curing agent (B) used in the present invention will be described.
本発明に用いるイソシアネート系硬化剤（Ｂ）は、トリレンジイソシアネート、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、キシリレンジイソシアネート、水添キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、水添ジフェニルメタンジイソシアネート、テトラメチルキシリレンジイソシアネート、ナフタレンジイソシアネート、トリフェニルメタントリイソシアネート、ポリメチレンポリフェニルイソシアネートなどのポリイソシアネート化合物、およびこれらポリイソシアネート化合物とトリメチロールプロパン等のポリオール化合物とのアダクト体、これらポリイソシアネート化合物のビュレット体やイソシアヌレート体、更にはこれらポリイソシアネート化合物と公知のポリエーテルポリオールやポリエステルポリオール、アクリルポリオール、ポリブタジエンポリオール、ポリイソプレンポリオール等とのアダクト体等が挙げられる。 The isocyanate curing agent (B) used in the present invention is tolylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tetramethylxylylene diisocyanate, naphthalene diisocyanate. , Polyisocyanate compounds such as triphenylmethane triisocyanate and polymethylene polyphenyl isocyanate, adducts of these polyisocyanate compounds and polyol compounds such as trimethylolpropane, burettes and isocyanurates of these polyisocyanate compounds, These polyisocyanate compounds and known polyether polyols And polyester polyols, acrylic polyols, polybutadiene polyols, adducts, etc. and polyisoprene polyol and the like.
イソシアネート系硬化剤（Ｂ）は、上記アクリル系ポリマー（Ａ）１００重量部に対して、０．０１〜１０重量部用いることが好ましい。 It is preferable to use 0.01 to 10 parts by weight of the isocyanate curing agent (B) with respect to 100 parts by weight of the acrylic polymer (A).
次に、本発明において難燃剤として下記一般式（１）で示されるホスフィン酸塩（Ｃ）（以下、単にホスフィン酸塩（Ｃ）ともいう）を用いることが重要である。ホスフィン酸塩（Ｃ）は、化合物中のリン含有率が高いため、難燃性を大きく向上できる。またホスフィン酸塩（Ｃ）は、高温高湿条件下においても加水分解しにくいため難燃性が低下しにくい傾向にある上に、粘着性が低下しにくい特徴がある。また、本発明において、有機フィラーとは、微粉末状の有機化合物であり、有機溶剤や水等に難溶または不溶なものである。
一般式（１）
Next, it is important to use a phosphinic acid salt (C) represented by the following general formula (1) (hereinafter also simply referred to as a phosphinic acid salt (C)) as a flame retardant in the present invention. Since the phosphinic acid salt (C) has a high phosphorus content in the compound, flame retardancy can be greatly improved. The phosphinic acid salt (C) is not easily hydrolyzed even under high-temperature and high-humidity conditions, so that the flame retardancy tends not to be lowered and the adhesiveness is hardly lowered. Moreover, in this invention, an organic filler is an organic compound of a fine powder form, and is hardly soluble or insoluble in an organic solvent, water, etc.
General formula (1)
（式（１）中、Ｒ1およびＲ2は、それぞれ独立に直鎖状のまたは枝分かれした炭素数１〜６のアルキル基またはアリール基であり、Ｍは、Ｍｇ、Ｃａ、Ａｌ、Ｓｂ、Ｓｎ、Ｇｅ、Ｔｉ、Ｆｅ、Ｚｒ、Ｚｎ、Ｃｅ、Ｂｉ、Ｓｒ、Ｍｎ、Ｌｉ、Ｎａ、Ｋまたはプロトン化した窒素塩基であり、ｍは１〜４の整数である。）
上記ホスフィン酸塩（Ｃ）としては、たとえば、トリスジエチルホスフィン酸アルミニウム、トリスメチルエチルホスフィン酸アルミニウム、トリスジフェニルホスフィン酸アルミニウム、ビスジエチルホスフィン酸亜鉛、ビスメチルエチルホスフィン酸亜鉛、ビスジフェニルホスフィン酸亜鉛、ビスジエチルホスフィン酸チタニル、テトラキスジエチルホスフィン酸チタン、ビスメチルエチルホスフィン酸チタニル、テトラキスメチルエチルホスフィン酸チタン、ビスジフェニルホスフィン酸チタニル、テトラキスジフェニルホスフィン酸チタン等およびそれらの任意の混合物よりなる群から選択されるもの等が挙げられる。これらの中でもトリスジエチルホスフィン酸アルミニウムが特に好適に用いられる。
(In the formula (1), R 1 and R 2 are each independently a linear or branched alkyl group or aryl group having 1 to 6 carbon atoms, and M is Mg, Ca, Al, Sb, Sn. , Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K or a protonated nitrogen base, and m is an integer of 1 to 4.)
Examples of the phosphinic acid salt (C) include aluminum trisdiethylphosphinate, aluminum trismethylethylphosphinate, aluminum trisdiphenylphosphinate, zinc bisdiethylphosphinate, zinc bismethylethylphosphinate, zinc bisdiphenylphosphinate, Selected from the group consisting of titanyl bisdiethylphosphinate, titanium tetrakisdiethylphosphinate, titanyl bismethylethylphosphinate, titanium tetrakismethylethylphosphinate, titanyl bisdiphenylphosphinate, titanium tetrakisdiphenylphosphinate and the like and any mixture thereof And the like. Of these, aluminum trisdiethylphosphinate is particularly preferably used.
また、ホスフィン酸塩（Ｃ）は、平均粒子径が０．１μｍ以上〜２０μｍ以下であることが重要である。さらに０．５μｍ以上〜１０μ ｍ以下が好ましく、さらに１μｍ以上５μｍ以下がより好ましい。平均粒子径が２０μｍ以下よりも大きいと、単位重量当りの表面積が低下する傾向にあり、難燃性の不足や、分散不良が生じる恐れがある。一方０．１μｍに満たない場合は、分散溶液の粘度の増大を引き起こし、塗工性が悪化する可能性がある。本発明においてホスフィン酸塩（Ｃ）は、上記の通り有機フィラーであるため粘着物性に寄与できる。なお本発明における平均粒子径は、体積基準での累積分布の５０％に相当する粒子径を意味し、動的光散乱法を利用した粒子径分布測定装置（例えば、日機装株式会社製、「マイクロトラック」）によって測定した数値である。 In addition, it is important that the phosphinic acid salt (C) has an average particle diameter of 0.1 μm to 20 μm. Furthermore, 0.5 μm or more and 10 μm or less are preferable, and 1 μm or more and 5 μm or less are more preferable. When the average particle diameter is larger than 20 μm or less, the surface area per unit weight tends to decrease, and there is a risk of insufficient flame retardancy and poor dispersion. On the other hand, when it is less than 0.1 μm, the viscosity of the dispersion solution is increased, and the coatability may be deteriorated. In the present invention, since the phosphinic acid salt (C) is an organic filler as described above, it can contribute to the physical properties of the adhesive. The average particle size in the present invention means a particle size corresponding to 50% of the cumulative distribution on a volume basis, and a particle size distribution measuring device using a dynamic light scattering method (for example, “Microdevices manufactured by Nikkiso Co., Ltd.”). It is a numerical value measured by the track ").
ホスフィン酸塩（Ｃ）は、上記アクリル系ポリマー（Ａ）１００に対して、好ましくは３０〜７０重量部、より好ましくは３５〜６５重量部、さらに好ましくは４０〜６０重量部用いることが好ましい。配合量が３０重量部に満たない場合は、難燃性が不足する恐れがある。一方、配合量が７０重量部を超える場合は、著しく粘着性が低下する恐れがある。 The phosphinic acid salt (C) is preferably used in an amount of 30 to 70 parts by weight, more preferably 35 to 65 parts by weight, and still more preferably 40 to 60 parts by weight with respect to the acrylic polymer (A) 100. If the blending amount is less than 30 parts by weight, the flame retardancy may be insufficient. On the other hand, when the blending amount exceeds 70 parts by weight, there is a fear that the adhesiveness is remarkably lowered.
本発明の難燃性粘着剤には、必要に応じて、メラミン樹脂微粒子やグアナミン樹脂（Ｎ含有）など、また水酸化マグネシウムや水酸化アルミニウムなどの水和金属化合物を少量添加することにより、難燃性をさらに向上させることもできる。 また、難燃性を損なわない範囲で、粘着特性などの向上のため、ロジン系樹脂などの各種粘着付与剤などを添加することもできる。 By adding a small amount of hydrated metal compound such as melamine resin fine particles, guanamine resin (N-containing) or magnesium hydroxide or aluminum hydroxide to the flame retardant pressure-sensitive adhesive of the present invention as needed, The flammability can be further improved. In addition, various tackifiers such as a rosin resin can be added in order to improve the adhesive properties and the like within a range not impairing the flame retardancy.
また、前記粘着剤中には、本発明の難燃性及び接着性を損なわない範囲で、必要に応じて、酸化防止剤、耐候剤、軟化剤、安定剤、充填剤、増量剤、補強剤等の各種添加剤を１ 種、又は２種以上を組み合わせて加えることができる。 Further, in the pressure-sensitive adhesive, an antioxidant, a weathering agent, a softening agent, a stabilizer, a filler, an extender, and a reinforcing agent are added as necessary within the range not impairing the flame retardancy and adhesiveness of the present invention. These additives can be added singly or in combination of two or more.
こうして得られた難燃性粘着剤は剥離シート上に塗布し、乾燥させ成膜し、基材と貼りあわせ、該粘着剤を積層してなる片面粘着テープとすることができる。もちろん、この難燃性粘着剤を用いて基材レスの粘着シートとすることができるし、芯材を用いて両面に前記粘着剤層を設けて両面粘着テープとすることもできる。 The flame retardant pressure-sensitive adhesive thus obtained can be applied onto a release sheet, dried to form a film, bonded to a base material, and a single-sided pressure-sensitive adhesive tape formed by laminating the pressure-sensitive adhesive. Of course, this flame-retardant pressure-sensitive adhesive can be used as a baseless pressure-sensitive adhesive sheet, or a double-sided pressure-sensitive adhesive tape can be provided by providing the pressure-sensitive adhesive layer on both sides using a core material.
剥離シートとしては、例えば、紙、またはポリエステル、ポリプロピレン、ポリエチレン、セルロースアセテート等のプラスチックフィルムや、アルミ、ステンレスなどの金属箔等を用いることができ、表面に厚みが１０ 〜２５０μm のものが好適に使用される。 As the release sheet, for example, paper, plastic films such as polyester, polypropylene, polyethylene, and cellulose acetate, metal foils such as aluminum and stainless steel, and the like are preferably used with a thickness of 10 to 250 μm on the surface. used.
基材としては、例えば、ポリエステル、ポリプロピレン、ポリエチレン、ポリフェニレンサルファイド、ポリイミド、ポリアミド、ポリフェニレンサルファイド、ポリアセテート、ポリエーテルエーテルケトン等のフィルム基材や、ガラスクロス、アセテートクロス等の布基材やペーパー基材、芯材等を用いることができ、厚みが１０〜２５０μｍのものが好適に使用される。 Examples of the base material include film base materials such as polyester, polypropylene, polyethylene, polyphenylene sulfide, polyimide, polyamide, polyphenylene sulfide, polyacetate and polyether ether ketone, cloth base materials such as glass cloth and acetate cloth, and paper bases. A material, a core material, and the like can be used, and those having a thickness of 10 to 250 μm are preferably used.
両面粘着テープの一般的な芯材としては、例えば， 和紙、レーヨン紙、マニラ紙など、合成樹脂フィルム類のポリエステル、ポリエチレン、ポリプロピレン、ポリスチレン、アクリル、ポリカーボネート、ナイロン、ポリアミド、ポリイミド、ポリアミドイミドなど、及び織布の布類又は不織布の合成樹脂類などを挙げることができ、厚みが４．５〜２５０μｍのものが好適に使用される。 As a general core material of double-sided adhesive tape, for example, Japanese paper, rayon paper, Manila paper, synthetic resin film polyester, polyethylene, polypropylene, polystyrene, acrylic, polycarbonate, nylon, polyamide, polyimide, polyamideimide, etc. And woven fabrics or non-woven synthetic resins, and those having a thickness of 4.5 to 250 μm are preferably used.
また必要に応じて、これら基材や芯材には易接着処理を施してもよい。処理方法としては、例えば、支持体の表面性の違いを利用して、粘着剤面に凹凸を持たせる方法、粘着剤塗布面にコロナ放電を処理する方法、および公知のアンカーコート剤を粘着剤層と支持体の境界に施す方法などが挙げられる。 Moreover, you may give an easily bonding process to these base materials and core materials as needed. As the treatment method, for example, a method of giving unevenness to the pressure-sensitive adhesive surface utilizing the difference in surface properties of the support, a method of treating corona discharge on the pressure-sensitive adhesive coating surface, and a known anchor coating agent as a pressure-sensitive adhesive Examples of the method include a method applied to the boundary between the layer and the support.
難燃性粘着剤の塗布は、従来公知の方法、例えば、グラビアコート方式、キスコート方式、ダイコート方式、リップコート方式、コンマコート方式、ブレードコート方式、ロールコート方式、ナイフコート方式、カーテンコート方式、スロットオリフィス方式、スプレーコート方式、バーコート方式等により行うことができる。難燃性粘着剤は、数回に分けて塗布してもよいし、１回で塗布してもよい。また、異なる方式を複数組み合わせてもよい。 Application of the flame retardant adhesive is a conventionally known method, for example, gravure coating method, kiss coating method, die coating method, lip coating method, comma coating method, blade coating method, roll coating method, knife coating method, curtain coating method, A slot orifice method, a spray coating method, a bar coating method, or the like can be used. The flame retardant adhesive may be applied in several times or may be applied once. A plurality of different methods may be combined.
本発明の難燃性粘着テープは、粘着剤層の膜厚が１０〜２００μｍ程度が好ましいが、この範囲内に限定されるものではなく、用途、要求性能に適した膜厚となるように塗布すればよい。 The flame-retardant pressure-sensitive adhesive tape of the present invention preferably has a thickness of the pressure-sensitive adhesive layer of about 10 to 200 μm, but is not limited to this range, and is applied so as to have a film thickness suitable for use and required performance. do it.
本発明の難燃性粘着テープの難燃性は、着火・延焼の危険性を排除する面から、ＵＬ９４ＶＴＭ−０を満足する事が好ましい。 The flame retardancy of the flame retardant adhesive tape of the present invention preferably satisfies UL94VTM-0 from the viewpoint of eliminating the risk of ignition and fire spread.
以下に、本発明を実施例によって詳しく説明するが、本発明は以下の実施例に限定されるものではない。また「部」、「％」は、それぞれ「重量部」、「重量％」を意味する。
＜アクリル系ポリマー（Ａ）合成例１＞
攪拌機、温度計、還流冷却器、滴下装置、窒素導入管を備えた反応容器に、ｎ−ブチル
アクリレート９９．８５部、アクリル酸０．１５部、酢酸エチル１２１．０部、ベンゾイルパーオキサイド０．２部を仕込み、攪拌しながら反応器中の空気を窒素置換し、還流するまで昇温して保持し、合計５ 時間反応させた。反応終了後、酢酸エチル３４．４部、トルエン２８．３部、重合禁止剤として２、５−ジターシャリブチルハイドロキノン０．５部を添加して希釈し、室温まで冷却し、不揮発分３４．０％のアクリル系ポリマー１の溶液を得た。アクリル系ポリマー１の重量平均分子量は５０万であった。
EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples. “Parts” and “%” mean “parts by weight” and “% by weight”, respectively.
<Acrylic polymer (A) synthesis example 1>
In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introducing tube, 99.85 parts of n-butyl acrylate, 0.15 parts of acrylic acid, 121.0 parts of ethyl acetate, 0. 2 parts were charged, and the air in the reactor was purged with nitrogen while stirring, and the temperature was raised to reflux until the reaction was continued for a total of 5 hours. After completion of the reaction, 34.4 parts of ethyl acetate, 28.3 parts of toluene, 0.5 part of 2,5-ditertiarybutyl hydroquinone as a polymerization inhibitor were added and diluted, cooled to room temperature, and a non-volatile content of 34.0. % Acrylic polymer 1 solution was obtained. The weight average molecular weight of the acrylic polymer 1 was 500,000.
＜アクリル系ポリマー（Ａ）合成例２＞
ｎ−ブチルアクリレート９９．７部、アクリル酸０．３部とした以外は、合成例１と同様な手順で反応を行い、不揮発分３４．０％のアクリル系ポリマー２の溶液を得た。アクリル系ポリマー２の重量平均分子量は５５万であった。
<Acrylic polymer (A) synthesis example 2>
A reaction was carried out in the same procedure as in Synthesis Example 1 except that 99.7 parts of n-butyl acrylate and 0.3 part of acrylic acid were used to obtain a solution of acrylic polymer 2 having a nonvolatile content of 34.0%. The weight average molecular weight of the acrylic polymer 2 was 550,000.
＜アクリル系ポリマー（Ａ）合成例３＞
ｎ−ブチルアクリレート９８．０部、アクリル酸２．０部とした以外は、合成例１と同様な手順で反応を行い、不揮発分３４．０％のアクリル系ポリマー３の溶液を得た。アクリル系ポリマー３の重量平均分子量は６０万であった。
<Acrylic polymer (A) synthesis example 3>
A reaction was carried out in the same procedure as in Synthesis Example 1 except that 98.0 parts of n-butyl acrylate and 2.0 parts of acrylic acid were used to obtain a solution of acrylic polymer 3 having a nonvolatile content of 34.0%. The weight average molecular weight of the acrylic polymer 3 was 600,000.
＜アクリル系ポリマー（Ａ）合成例４＞
ｎ−ブチルアクリレート９４．０部、アクリル酸６．０部とした以外は、合成例１と同様な手順で反応を行い、不揮発分３４．０％のアクリル系ポリマー４の溶液を得た。アクリル系ポリマー４の重量平均分子量は６１万であった。
<Acrylic polymer (A) synthesis example 4>
A reaction was carried out in the same procedure as in Synthesis Example 1 except that 94.0 parts of n-butyl acrylate and 6.0 parts of acrylic acid were used to obtain a solution of acrylic polymer 4 having a nonvolatile content of 34.0%. The weight average molecular weight of the acrylic polymer 4 was 610,000.
＜アクリル系ポリマー（Ａ）合成例５＞
ｎ−ブチルアクリレート９０．０部、アクリル酸１０．０部とした以外は、合成例１と同様な手順で反応を行い、不揮発分３４．０％のアクリル系ポリマー５の溶液を得た。アクリル系ポリマー５の重量平均分子量は７０万であった。
<Acrylic polymer (A) synthesis example 5>
A reaction was carried out in the same procedure as in Synthesis Example 1 except that 90.0 parts of n-butyl acrylate and 10.0 parts of acrylic acid were used to obtain a solution of acrylic polymer 5 having a nonvolatile content of 34.0%. The weight average molecular weight of the acrylic polymer 5 was 700,000.
＜アクリル系ポリマー（Ａ）合成例６＞
ｎ−ブチルアクリレート８０．０部、アクリル酸２０．０部とした以外は、合成例１と同様な手順で反応を行ったが、反応途中でゲル化してしまった。
<Acrylic polymer (A) synthesis example 6>
The reaction was performed in the same procedure as in Synthesis Example 1 except that 80.0 parts of n-butyl acrylate and 20.0 parts of acrylic acid were used, but gelation occurred during the reaction.
＜アクリル系ポリマー（Ａ）合成例７＞
ｎ−ブチルアクリレート１００．０部とした以外は、合成例１と同様な手順で反応を行い、不揮発分３４．０％のアクリル系ポリマー７の溶液を得た。アクリル系ポリマー７の重量平均分子量は５５万であった。
<Acrylic polymer (A) synthesis example 7>
The reaction was performed in the same procedure as in Synthesis Example 1 except that 100.0 parts of n-butyl acrylate was used, to obtain a solution of acrylic polymer 7 having a non-volatile content of 34.0%. The weight average molecular weight of the acrylic polymer 7 was 550,000.
＜難燃剤分散液調整例１＞
合成例１で得られたアクリル系ポリマー（Ａ）溶液１００部、ホスフィン酸塩（Ｂ）としてトリスジエチルホスフィン酸アルミニウム（クラリアントジャパン株式会社製：エクソリットＯＰ−９３５ 平均粒子径２〜３μｍ）６８部、ついでこの溶液にメチルエチルケトンを加えて、不揮発分が３０．０％になるように調製し、溶液を十分に攪拌した後に直径３．０ｍｍのガラスビーズ（ポッターズ・バロティーニ社製）を用いてペイントコンデショナーで１時間分散し難燃剤分散液１を得た。
<Flame retardant dispersion adjustment example 1>
100 parts of the acrylic polymer (A) solution obtained in Synthesis Example 1, 68 parts of aluminum trisdiethylphosphinate (manufactured by Clariant Japan Co., Ltd .: Exolit OP-935, average particle diameter of 2 to 3 μm) as the phosphinate (B), Next, methyl ethyl ketone was added to this solution to prepare a non-volatile content of 30.0%. After sufficiently stirring the solution, a paint conditioner was prepared using glass beads having a diameter of 3.0 mm (Potters Barotini). To obtain a flame retardant dispersion 1.
＜難燃剤分散液調整例２＞
アクリル系ポリマー（Ａ）として合成例２で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液２を得た。
<Flame retardant dispersion adjustment example 2>
Flame retardant dispersion 2 was obtained in the same composition and procedure as in Flame retardant dispersion preparation example 1 except that the acrylic polymer solution obtained in Synthesis Example 2 was used as the acrylic polymer (A).
＜難燃剤分散液調整例３＞
アクリル系ポリマー（Ａ）として合成例２で得られたアクリル系ポリマー溶液、ホスフィン酸塩（Ｂ）としてトリスジエチルホスフィン酸アルミニウム（クラリアントジャパン株式会社製：エクソリットＯＰ−９３５ 平均粒子径２〜３μｍ）１０２部を用いた以外は、分散液調整例１と同様の配合、手順で難燃剤分散液３を得た。
<Flame retardant dispersion adjustment example 3>
The acrylic polymer solution obtained in Synthesis Example 2 as the acrylic polymer (A), and aluminum trisdiethylphosphinate (manufactured by Clariant Japan Co., Ltd .: Exolit OP-935, average particle diameter of 2 to 3 μm) as the phosphinate (B) 102 The flame retardant dispersion liquid 3 was obtained by the same composition and procedure as in the dispersion liquid adjustment example 1 except that the parts were used.
＜難燃剤分散液調整例４＞
アクリル系ポリマー（Ａ）として合成例３で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液４を得た。
<Flame retardant dispersion liquid adjustment example 4>
A flame retardant dispersion 4 was obtained by the same composition and procedure as in Flame retardant dispersion preparation example 1 except that the acrylic polymer solution obtained in Synthesis Example 3 was used as the acrylic polymer (A).
＜難燃剤分散液調整例５＞
アクリル系ポリマー（Ａ）として合成例４で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液５を得た。
<Flame retardant dispersion liquid adjustment example 5>
Flame retardant dispersion 5 was obtained by the same composition and procedure as in Flame retardant dispersion preparation example 1 except that the acrylic polymer solution obtained in Synthesis Example 4 was used as the acrylic polymer (A).
＜難燃剤分散液調整例６＞
アクリル系ポリマー（Ａ）として合成例４で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例３と同様の配合、手順で難燃剤分散液６を得た。
<Flame retardant dispersion liquid adjustment example 6>
Flame retardant dispersion 6 was obtained by the same composition and procedure as in Flame retardant dispersion preparation example 3 except that the acrylic polymer solution obtained in Synthesis Example 4 was used as the acrylic polymer (A).
＜難燃剤分散液調整例７＞
アクリル系ポリマー（Ａ）として合成例５で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液７を得た。
<Flame retardant dispersion adjustment example 7>
A flame retardant dispersion liquid 7 was obtained by the same composition and procedure as the flame retardant dispersion preparation example 1 except that the acrylic polymer solution obtained in Synthesis Example 5 was used as the acrylic polymer (A).
＜難燃剤分散液調整例８＞
アクリル系ポリマー（Ａ）として合成例７で得られたアクリル系ポリマー溶液を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液８を得た。
<Flame retardant dispersion adjustment example 8>
A flame retardant dispersion liquid 8 was obtained by the same composition and procedure as the flame retardant dispersion preparation example 1 except that the acrylic polymer solution obtained in Synthesis Example 7 was used as the acrylic polymer (A).
＜難燃剤分散液調整例９＞
アクリル系ポリマー（Ａ）として合成例３で得られたアクリル系ポリマー溶液とホスフィン酸塩（Ｂ）の代わりに水酸化アルミニウム（日本軽金属株式会社製：ＢＦ−０１３ 平均粒子径１〜２μｍ）を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液９を得た。
<Flame retardant dispersion liquid adjustment example 9>
As the acrylic polymer (A), aluminum hydroxide (manufactured by Nippon Light Metal Co., Ltd .: BF-013 average particle size of 1 to 2 μm) is used instead of the acrylic polymer solution obtained in Synthesis Example 3 and the phosphinate (B). Except for the above, flame retardant dispersion liquid 9 was obtained by the same formulation and procedure as in Flame retardant dispersion preparation example 1.
＜難燃剤分散液調整例１０＞
アクリル系ポリマー（Ａ）として合成例４で得られたアクリル系ポリマー溶液とホスフィン酸塩（Ｂ）の代わりに水酸化アルミニウム（日本軽金属株式会社製：ＢＦ−０１３平均粒子径１〜２μｍ）を用いた以外は、難燃剤分散液調整例３と同様の配合、手順で難燃剤分散液１０を得た。
<Flame retardant dispersion liquid adjustment example 10>
As the acrylic polymer (A), aluminum hydroxide (manufactured by Nippon Light Metal Co., Ltd .: BF-013 average particle size of 1 to 2 μm) is used instead of the acrylic polymer solution obtained in Synthesis Example 4 and the phosphinate (B). Except for the above, flame retardant dispersion liquid 10 was obtained by the same formulation and procedure as in Preparation 3 of flame retardant dispersion liquid.
＜難燃剤分散液調整例１１＞
アクリル系ポリマー（Ａ）として合成例３で得られたアクリル系ポリマー溶液とホスフィン酸塩（ Ｂ ）の代わりにメラミンシアヌレート（ＣＢＣ株式会社：ＢＵＤＩＴ３１５Ｓ 平均粒子径３μｍ）を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液１１を得た。
<Flame retardant dispersion liquid adjustment example 11>
A flame retardant, except that melamine cyanurate (CBC Co., Ltd .: BUDIT315S average particle diameter 3 μm) was used as the acrylic polymer (A) in place of the acrylic polymer solution obtained in Synthesis Example 3 and the phosphinate (B). Flame retardant dispersion 11 was obtained by the same formulation and procedure as in Dispersion Preparation Example 1.
＜難燃剤分散液調整例１２＞
アクリル系ポリマー（Ａ）として合成例４で得られたアクリル系ポリマー溶液とホスフィン酸塩（Ｂ）の代わりにメラミンシアヌレート（ＣＢＣ株式会社：ＢＵＤＩＴ３１５Ｓ 平均粒子径３μｍ）を用いた以外は、難燃剤分散液調整例３と同様の配合、手順で難燃剤分散液１２を得た。
<Flame retardant dispersion adjustment example 12>
A flame retardant, except that melamine cyanurate (CBC Corporation: BUDIT315S average particle size 3 μm) was used in place of the acrylic polymer solution obtained in Synthesis Example 4 and the phosphinate (B) as the acrylic polymer (A). Flame retardant dispersion liquid 12 was obtained by the same formulation and procedure as in Dispersion Preparation Example 3.
＜難燃剤分散液調整例１３＞
アクリル系ポリマー（Ａ）として合成例３で得られたアクリル系ポリマー溶液とホスフィン酸塩（Ｂ）の代わりにポリリン酸アンモニウム（ＣＢＣ株式会社：Ｃ−６０ 平均粒子径７〜８μｍ）を用いた以外は、難燃剤分散液調整例１と同様の配合、手順で難燃剤分散液１３を得た。
<Flame retardant dispersion adjustment example 13>
Ammonium polyphosphate (CBC Corporation: C-60 average particle diameter: 7 to 8 μm) was used in place of the acrylic polymer solution obtained in Synthesis Example 3 and the phosphinate (B) as the acrylic polymer (A). Obtained the flame retardant dispersion liquid 13 in the same composition and procedure as in the flame retardant dispersion preparation example 1.
＜難燃剤分散液調整例１４＞
アクリル系ポリマー（Ａ）として合成例４で得られたアクリル系ポリマー溶液とホスフィン酸塩（Ｂ）の代わりにポリリン酸アンモニウム（ＣＢＣ株式会社：Ｃ−６０ 平均粒子径７〜８μｍ）を用いた以外は、難燃剤分散液調整例３と同様の配合、手順で難燃剤分散液１４を得た。
<Flame retardant dispersion adjustment example 14>
Ammonium polyphosphate (CBC Corporation: C-60 average particle diameter: 7 to 8 μm) was used in place of the acrylic polymer solution obtained in Synthesis Example 4 and the phosphinate (B) as the acrylic polymer (A). Obtained the flame retardant dispersion liquid 14 by the same composition and procedure as the flame retardant dispersion preparation example 3.
［難燃剤分散液の安定性の評価］
得られた難燃剤分散液を２３℃で放置し、経時での安定性を確認し、次の基準で評価した。結果は表１に示す。
◎・・・１週間放置後の分散液に変化がない
○・・・１週間放置後の分散液にほとんど変化がない
△・・・１週間放置後の分散液に凝集物が生じた
×・・・１週間以内に分散液がゲル化した。
[Evaluation of stability of flame retardant dispersion]
The obtained flame retardant dispersion was allowed to stand at 23 ° C., stability over time was confirmed, and evaluation was performed according to the following criteria. The results are shown in Table 1.
◎ ・ ・ ・ No change in dispersion after standing for 1 week ○ ・ ・ ・ No change in dispersion after standing for 1 week △ ・ ・ ・ Agglomerates formed in dispersion after standing for 1 week × -The dispersion gelled within one week.
＜実施例１＞
難燃剤分散液例１で得られた難燃剤分散液１００部に対して、合成例１で得られたアクリル系ポリマー（Ａ）を８８．２部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．７部を添加して良く攪拌し、粘着剤溶液を得た。得られた粘着剤溶液を、ドクターブレードで乾燥膜厚４５μｍとなるように、厚さ７５μｍ の剥離シート上に塗布し、乾燥させ、粘着剤層を形成し、次いで厚さ２５μｍのＰＥＴフィルムの片面、及び坪量が６ｇ／ｍ2のレーヨン不織布の両面にラミネートして、ＰＥＴフィルム／粘着剤層／剥離シートからなる片面粘着テープ１及び、剥離シート／粘着剤層／不織布／粘着剤層／剥離シートからなる両面粘着テープ１をそれぞれ得た。この粘着テープを２３℃５０％ＲＨの雰囲気下で７日間熟成させた。
<Example 1>
88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 1 and TDI / TMP (tolylene diisocyanate) as a crosslinking agent with respect to 100 parts of the flame retardant dispersion obtained in Example 1 of the flame retardant dispersion 0.7 parts of trimethylolpropane adduct of Nate) was added and stirred well to obtain an adhesive solution. The obtained pressure-sensitive adhesive solution was applied onto a 75 μm-thick release sheet with a doctor blade so as to have a dry film thickness of 45 μm, dried to form a pressure-sensitive adhesive layer, and then one side of a 25 μm-thick PET film And laminated on both sides of a rayon nonwoven fabric having a basis weight of 6 g / m 2 and a single-sided adhesive tape 1 comprising PET film / adhesive layer / release sheet and release sheet / adhesive layer / nonwoven fabric / adhesive layer / release The double-sided pressure-sensitive adhesive tape 1 made of a sheet was obtained. This adhesive tape was aged for 7 days in an atmosphere of 23 ° C. and 50% RH.
＜実施例２＞
難燃剤分散液例２で得られた難燃剤分散液１００部に対して、合成例２で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ２及び両面粘着テープ２を得た。
<Example 2>
The same composition as in Example 1 except that 88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 2 was used for 100 parts of the flame retardant dispersion obtained in Flame Retardant Dispersion Example 2. The single-sided adhesive tape 2 and the double-sided adhesive tape 2 were obtained by the procedure.
＜実施例３＞
難燃剤分散液例４で得られた難燃剤分散液１００部に対して、合成例３で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ３及び両面粘着テープ３を得た
<Example 3>
The same composition as in Example 1 except that 88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 3 was used for 100 parts of the flame retardant dispersion liquid obtained in Flame retardant dispersion example 4. The single-sided adhesive tape 3 and the double-sided adhesive tape 3 were obtained by the procedure.
＜実施例４＞
難燃剤分散液例５で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）１３８．７部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）１．１部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ４及び両面粘着テープ４を得た。
<Example 4>
138.7 parts of the acrylic polymer (A) obtained in Synthesis Example 4 with respect to 100 parts of the flame retardant dispersion obtained in Flame Retardant Dispersion Example 5, and TDI / TMP (tolylene diisocyanate as a crosslinking agent) A single-sided pressure-sensitive adhesive tape 4 and a double-sided pressure-sensitive adhesive tape 4 were obtained by the same composition and procedure as in Example 1 except that 1.1 parts of trimethylolpropane adduct were used.
＜実施例５＞
難燃剤分散液例５で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ５及び両面粘着テープ５を得た。
<Example 5>
The same composition as in Example 1 except that 88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 4 was used for 100 parts of the flame retardant dispersion obtained in Flame Retardant Dispersion Example 5. The single-sided adhesive tape 5 and the double-sided adhesive tape 5 were obtained by the procedure.
＜実施例６＞
難燃剤分散液例５で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）６１．１部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．６部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ６及び両面粘着テープ６を得た。
<Example 6>
61.1 parts of the acrylic polymer (A) obtained in Synthesis Example 4 with respect to 100 parts of the flame retardant dispersion obtained in Flame Retardant Dispersion Example 5, and TDI / TMP (tolylene diisocyanate) as a crosslinking agent A single-sided pressure-sensitive adhesive tape 6 and a double-sided pressure-sensitive adhesive tape 6 were obtained by the same composition and procedure as in Example 1 except that 0.6 part of trimethylolpropane adduct was used.
＜実施例７＞
難燃剤分散液例７で得られた難燃剤分散液１００部に対して、合成例５で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ７及び両面粘着テープ７を得た。
<Example 7>
The same composition as in Example 1 except that 88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 5 was used for 100 parts of the flame retardant dispersion obtained in Flame retardant dispersion Example 7. The single-sided adhesive tape 7 and the double-sided adhesive tape 7 were obtained by the procedure.
＜比較例１＞
難燃剤分散液例５で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）１６６．７部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）１．３部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ８及び両面粘着テープ８を得た。
<Comparative Example 1>
166.7 parts of the acrylic polymer (A) obtained in Synthesis Example 4 with respect to 100 parts of the flame retardant dispersion obtained in Example 5 of the flame retardant dispersion, and TDI / TMP (tolylene diisocyanate) as a crosslinking agent The single-sided pressure-sensitive adhesive tape 8 and the double-sided pressure-sensitive adhesive tape 8 were obtained in the same composition and procedure as in Example 1 except that 1.3 parts of trimethylolpropane adduct was used.
＜比較例２＞
難燃剤分散液例５で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）２９．４部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．４部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ９及び両面粘着テープ９を得た。
<Comparative example 2>
29.4 parts of the acrylic polymer (A) obtained in Synthesis Example 4 with respect to 100 parts of the flame retardant dispersion obtained in Example 5 of the flame retardant dispersion, and TDI / TMP (tolylene diisocyanate) as a crosslinking agent A single-sided pressure-sensitive adhesive tape 9 and a double-sided pressure-sensitive adhesive tape 9 were obtained by the same composition and procedure as in Example 1 except that 0.4 part of trimethylolpropane adduct was used.
＜比較例３＞
難燃剤分散液例８で得られた難燃剤分散液１００部に対して、合成例７で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１０及び両面粘着テープ１０を得た。
<Comparative Example 3>
The same composition as in Example 1 except that 88.2 parts of the acrylic polymer (A) obtained in Synthesis Example 7 was used with respect to 100 parts of the flame retardant dispersion obtained in Flame Retardant Dispersion Example 8. The single-sided adhesive tape 10 and the double-sided adhesive tape 10 were obtained by the procedure.
＜比較例４＞
難燃剤分散液例９で得られた難燃剤分散液１００部に対して、合成例３で得られたアクリル系ポリマー（Ａ）２９．４部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．４部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１１及び両面粘着テープ１１を得た。
<Comparative example 4>
29.4 parts of the acrylic polymer (A) obtained in Synthesis Example 3 with respect to 100 parts of the flame retardant dispersion obtained in Example 9 of the flame retardant dispersion, and TDI / TMP (tolylene diisocyanate) as a crosslinking agent A single-sided pressure-sensitive adhesive tape 11 and a double-sided pressure-sensitive adhesive tape 11 were obtained by the same composition and procedure as in Example 1 except that 0.4 part of trimethylolpropane adduct was used.
＜比較例５＞
難燃剤分散液例１１で得られた難燃剤分散液１００部に対して、合成例３で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１２及び両面粘着テープ１２を得た。
<Comparative Example 5>
The same composition as Example 1 except having used 88.2 parts of acrylic polymers (A) obtained by the synthesis example 3 with respect to 100 parts of flame retardant dispersion liquid obtained by the flame retardant dispersion liquid example 11. The single-sided adhesive tape 12 and the double-sided adhesive tape 12 were obtained by the procedure.
＜比較例６＞
難燃剤分散液例１１で得られた難燃剤分散液１００部に対して、合成例３で得られたアクリル系ポリマー（Ａ）２９．４部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．４部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１３及び両面粘着テープ１３を得た。
<Comparative Example 6>
29.4 parts of the acrylic polymer (A) obtained in Synthesis Example 3 and TDI / TMP (tolylene diisocyanate) as a crosslinking agent with respect to 100 parts of the flame retardant dispersion obtained in Example 11 of the flame retardant dispersion A single-sided pressure-sensitive adhesive tape 13 and a double-sided pressure-sensitive adhesive tape 13 were obtained in the same composition and procedure as in Example 1 except that 0.4 part of trimethylolpropane adduct was used.
＜比較例７＞
難燃剤分散液例１４で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）８８．２部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１４及び両面粘着テープ１４を得た。
<Comparative Example 7>
The same composition as Example 1 except having used 88.2 parts of acrylic polymers (A) obtained by the synthesis example 4 with respect to 100 parts of flame retardant dispersion liquid obtained by the flame retardant dispersion example 14. The single-sided adhesive tape 14 and the double-sided adhesive tape 14 were obtained by the procedure.
＜比較例８＞
難燃剤分散液例１４で得られた難燃剤分散液１００部に対して、合成例４で得られたアクリル系ポリマー（Ａ）２９．４部、架橋剤としてＴＤＩ／ＴＭＰ（トリレンジイソシネートのトリメチロールプロパンアダクト体）０．４部を用いた以外は、実施例１と同様な配合、手順で片面粘着テープ１５及び両面粘着テープ１５を得た。
<Comparative Example 8>
29.4 parts of the acrylic polymer (A) obtained in Synthesis Example 4 with respect to 100 parts of the flame retardant dispersion obtained in Example 14 of the flame retardant dispersion, and TDI / TMP (tolylene diisocyanate) as a crosslinking agent Single-sided pressure-sensitive adhesive tape 15 and double-sided pressure-sensitive adhesive tape 15 were obtained by the same composition and procedure as in Example 1 except that 0.4 part of trimethylolpropane adduct was used.
＜比較例９＞
合成例４で得られたアクリル系ポリマー（Ａ）を１００重量部に対して、難燃剤としてホスフィン酸塩（Ｂ）の代わりにホスファゼン（大塚化学株式会社：ＳＰＢ−１００）１７部を１７部のＭＥＫで溶解させて添加して良く攪拌し、粘着剤溶液を得た以外は、実施例１と同様な配合、手順で片面粘着テープ１６及び両面粘着テープ１６を得た
<Comparative Example 9>
For 100 parts by weight of the acrylic polymer (A) obtained in Synthesis Example 4, 17 parts of phosphazene (Otsuka Chemical Co., Ltd .: SPB-100) instead of phosphinate (B) as a flame retardant A single-sided pressure-sensitive adhesive tape 16 and a double-sided pressure-sensitive adhesive tape 16 were obtained by the same composition and procedure as in Example 1 except that the pressure-sensitive adhesive solution was obtained by dissolving with MEK and stirring well.
以上、各実施例及び比較例として得られた粘着テープの物性評価を以下の方法で行った。得られた結果を〔表２〕〜〔表４〕に示した。 As described above, the physical properties of the pressure-sensitive adhesive tapes obtained as Examples and Comparative Examples were evaluated by the following methods. The obtained results are shown in [Table 2] to [Table 4].
〔粘着力〕
上記片面粘着テープを２３℃×５０％ＲＨの標準状態において、それぞれ２５ｍｍ幅×１００ｍｍ長さでカットし、ステンレス板に２ｋｇのゴムローラーを１往復させて貼り付け、同標準状態で２４時間放置後、８５℃及び６０℃×９５％ＲＨ環境下で１６８時間放置後、引っ張り速度３００ｍｍ／分、剥離角度１８０°の条件で引っ張り試験機にて粘着力を測定した。
〔Adhesive force〕
The above single-sided adhesive tape is cut in a standard condition of 23 ° C. × 50% RH, each with a width of 25 mm × 100 mm, and pasted on a stainless steel plate by reciprocating a 2 kg rubber roller, and left in the standard condition for 24 hours. After being left for 168 hours in an environment of 85 ° C. and 60 ° C. × 95% RH, the adhesive strength was measured with a tensile tester under the conditions of a tensile speed of 300 mm / min and a peeling angle of 180 °.
〔保持力〕
上記片面粘着テープを２３℃×５０％ＲＨの標準状態において、それぞれ２５ｍｍ幅×１００ｍｍ長さでカットし、そのうち２５ｍｍ幅×２５ｍｍ長さをステンレス板に２ｋｇのゴムローラーを１往復させて貼り付け、貼付から２０分後に８０℃雰囲気下１ｋｇｆの荷重をかけ、１時間後のズレ距離または落下時間を測定した。
[Retention force]
In the standard state of 23 ° C. × 50% RH, the single-sided adhesive tape was cut into 25 mm width × 100 mm length, and 25 mm width × 25 mm length was pasted on a stainless steel plate by reciprocating a 2 kg rubber roller once, A load of 1 kgf was applied in an 80 ° C. atmosphere 20 minutes after application, and the displacement distance or drop time after 1 hour was measured.
〔難燃性〕
上記両面粘着テープを用いて、ＵＬ規格（ＵＬ９４：薄手材料垂直燃焼試験）に準じて燃焼試験を行って判定した。
○：ＵＬ９４規格ＶＴＭ−０グレードを達成できる。
△：ＵＬ９４規格ＶＴＭ−１グレードを達成できる。
×：ＵＬ９４規格ＶＴＭ−０、ＶＴＭ−１グレードを達成できない。
〔Flame retardance〕
Using the double-sided adhesive tape, a combustion test was performed in accordance with UL standards (UL94: thin material vertical combustion test).
A: UL94 standard VTM-0 grade can be achieved.
Δ: UL94 standard VTM-1 grade can be achieved.
X: UL94 standard VTM-0, VTM-1 grade cannot be achieved.
表２〜表４の結果から明らかのように、本発明における難燃性アクリル粘着剤及び該粘着剤を用いた塗工物は、優れた粘着性と難燃性を持ち、８５℃および６５℃−９５％経時後においてもそれぞれ高い粘着性を維持することから長期保存性にも優れていることがわかる。 As apparent from the results of Tables 2 to 4, the flame-retardant acrylic pressure-sensitive adhesive and the coated product using the pressure-sensitive adhesive in the present invention have excellent tackiness and flame retardancy, and are 85 ° C and 65 ° C. It can be seen that since the high adhesiveness is maintained even after lapse of −95%, it is excellent in long-term storage.
Claims (2)
前記ホスフィン酸塩（Ｃ）を、アクリル系ポリマー（Ａ）１００重量部に対して、３０〜７０重量部含有し、
さらに前記ホスフィン酸塩（Ｃ）の平均粒子径が０．１μｍ以上〜２０μｍ以下であることを特徴とする難燃性粘着剤。
一般式（１）
The phosphinate (C) is contained in an amount of 30 to 70 parts by weight with respect to 100 parts by weight of the acrylic polymer (A).
Furthermore, the flame retardant pressure-sensitive adhesive, wherein the phosphinic acid salt (C) has an average particle size of 0.1 μm to 20 μm.
General formula (1)
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013060535A (en) * | 2011-09-14 | 2013-04-04 | Denki Kagaku Kogyo Kk | High viscosity acrylic resin composition and application of the same |
| WO2014069461A1 (en) * | 2012-10-29 | 2014-05-08 | リンテック株式会社 | Flame-retardant adhesive composition and flame-retardant adhesive sheet |
| JP2015067653A (en) * | 2013-09-27 | 2015-04-13 | リンテック株式会社 | Pressure sensitive adhesive sheet |
| CN112437797A (en) * | 2018-07-24 | 2021-03-02 | 汉高股份有限及两合公司 | Flame retardant adhesive composition |
| CN113861898A (en) * | 2021-10-20 | 2021-12-31 | 福建友谊胶粘带集团有限公司 | Automobile PE wire harness flame-retardant adhesive tape and preparation method thereof |
| WO2023152913A1 (en) * | 2022-02-10 | 2023-08-17 | ビッグテクノス株式会社 | Electrically removable pressure-sensitive adhesive sheet and production method therefor |
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| JP2010132820A (en) * | 2008-12-05 | 2010-06-17 | Somar Corp | Flame-retardant resin composition, self-adhesive sheet using the same and method of manufacturing the same |
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| JP2008291217A (en) * | 2007-03-29 | 2008-12-04 | Clariant Internatl Ltd | Adhesive and sealing material made flame-retardant |
| JP2010132820A (en) * | 2008-12-05 | 2010-06-17 | Somar Corp | Flame-retardant resin composition, self-adhesive sheet using the same and method of manufacturing the same |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013060535A (en) * | 2011-09-14 | 2013-04-04 | Denki Kagaku Kogyo Kk | High viscosity acrylic resin composition and application of the same |
| WO2014069461A1 (en) * | 2012-10-29 | 2014-05-08 | リンテック株式会社 | Flame-retardant adhesive composition and flame-retardant adhesive sheet |
| JPWO2014069461A1 (en) * | 2012-10-29 | 2016-09-08 | リンテック株式会社 | Flame retardant adhesive composition and flame retardant adhesive sheet |
| JP2015067653A (en) * | 2013-09-27 | 2015-04-13 | リンテック株式会社 | Pressure sensitive adhesive sheet |
| CN112437797A (en) * | 2018-07-24 | 2021-03-02 | 汉高股份有限及两合公司 | Flame retardant adhesive composition |
| JP2021532233A (en) * | 2018-07-24 | 2021-11-25 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co. KGaA | Flame-retardant adhesive composition |
| JP7295939B2 (en) | 2018-07-24 | 2023-06-21 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | Flame-retardant adhesive composition |
| CN113861898A (en) * | 2021-10-20 | 2021-12-31 | 福建友谊胶粘带集团有限公司 | Automobile PE wire harness flame-retardant adhesive tape and preparation method thereof |
| WO2023152913A1 (en) * | 2022-02-10 | 2023-08-17 | ビッグテクノス株式会社 | Electrically removable pressure-sensitive adhesive sheet and production method therefor |
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