WO2023286767A1 - Thermoconductive material composition - Google Patents
Thermoconductive material composition Download PDFInfo
- Publication number
- WO2023286767A1 WO2023286767A1 PCT/JP2022/027393 JP2022027393W WO2023286767A1 WO 2023286767 A1 WO2023286767 A1 WO 2023286767A1 JP 2022027393 W JP2022027393 W JP 2022027393W WO 2023286767 A1 WO2023286767 A1 WO 2023286767A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- group
- thermally conductive
- compound
- mass
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 239000000463 material Substances 0.000 title claims abstract description 21
- 238000004132 cross linking Methods 0.000 claims abstract description 37
- 229920000800 acrylic rubber Polymers 0.000 claims abstract description 36
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 36
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 18
- -1 aziridine compound Chemical class 0.000 claims description 123
- 239000000178 monomer Substances 0.000 claims description 78
- 239000004020 conductor Substances 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000011231 conductive filler Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 229910052582 BN Inorganic materials 0.000 claims description 8
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000000344 soap Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 229920000768 polyamine Polymers 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 4
- 150000001541 aziridines Chemical class 0.000 claims description 4
- 150000004659 dithiocarbamates Chemical class 0.000 claims description 4
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 5
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- 239000003505 polymerization initiator Substances 0.000 description 10
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
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- 238000012546 transfer Methods 0.000 description 5
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000000701 coagulant Substances 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
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- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 2
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
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- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
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- 239000004800 polyvinyl chloride Substances 0.000 description 2
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- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000012744 reinforcing agent Substances 0.000 description 2
- 238000010057 rubber processing Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
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- 239000008117 stearic acid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LPXPSTWBTULMJE-UHFFFAOYSA-N n-phenylbutan-1-imine Chemical compound CCCC=NC1=CC=CC=C1 LPXPSTWBTULMJE-UHFFFAOYSA-N 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- GNHGCDCAOUNOCA-UHFFFAOYSA-N naphthalene-2,6-dicarbohydrazide Chemical compound C1=C(C(=O)NN)C=CC2=CC(C(=O)NN)=CC=C21 GNHGCDCAOUNOCA-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZWWQICJTBOCQLA-UHFFFAOYSA-N o-propan-2-yl (propan-2-yloxycarbothioyldisulfanyl)methanethioate Chemical compound CC(C)OC(=S)SSC(=S)OC(C)C ZWWQICJTBOCQLA-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- HATIEXJZXOLRAO-UHFFFAOYSA-N octanedihydrazide Chemical compound NNC(=O)CCCCCCC(=O)NN HATIEXJZXOLRAO-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003004 phosphinoxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VMBJJCDVORDOCF-UHFFFAOYSA-N prop-2-enyl 2-chloroacetate Chemical group ClCC(=O)OCC=C VMBJJCDVORDOCF-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 239000006235 reinforcing carbon black Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical class [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 150000003497 tellurium Chemical class 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical class [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 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 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-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
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- RRMGUSMHFWKTGB-UHFFFAOYSA-N tridecanedihydrazide Chemical compound NNC(=O)CCCCCCCCCCCC(=O)NN RRMGUSMHFWKTGB-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/14—Solid materials, e.g. powdery or granular
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K7/00—Constructional details common to different types of electric apparatus
- H05K7/20—Modifications to facilitate cooling, ventilating, or heating
Abstract
Provided are: a thermoconductive material composition having excellent thermal conductivity; and a thermoconductive material (for example, a thermoconductive sheet) obtained by crosslinking same. This thermoconductive material composition containing at least an acrylic elastomer, a cross-linking agent, and a thermoconductive filler, and a thermoconductive material (for example, a thermoconductive sheet) produced from said thermoconductive material composition, both have excellent thermal conductivity, and, by using an acrylic elastomer as a medium for securing the thermoconductive filler, do not generate an outgas, which causes short-circuiting in an electronic circuit, such as a low-molecular weight siloxane which is a problem associated with silicone rubbers.
Description
本発明は熱伝導用素材組成物、および、それを架橋してなる熱伝導性素材(例えば、熱伝導性シート)に関するものであり、詳しくは、熱伝導用素材組成物から作製される熱伝導性素材(例えば、熱伝導性シート)が高い熱導電性を有する。
TECHNICAL FIELD The present invention relates to a thermally conductive material composition and a thermally conductive material (for example, a thermally conductive sheet) obtained by cross-linking it. A thermally conductive material (for example, a thermally conductive sheet) has high thermal conductivity.
従来、電子機器等から発せられる熱を外部へ放出するために熱伝導性シート等の熱伝導性素材が用いられている。一般的に熱伝導性シート等の熱伝導性素材は、熱源から発せられる熱を引き受け、その後、ヒートシンクへ伝える役割を担っている。近年、電子機器の実装技術の向上に伴い、機器の小型化、薄型化が進んでおり、機器から発生する熱を効率的に外部へ放出することが重要となっており、より高い熱伝導率が求められている。
Conventionally, thermally conductive materials such as thermally conductive sheets are used to release the heat generated by electronic devices to the outside. In general, thermally conductive materials such as thermally conductive sheets have the role of receiving heat emitted from a heat source and then transferring it to a heat sink. In recent years, along with improvements in mounting technology for electronic devices, devices have become smaller and thinner. is required.
このような状況下において、1分子中に2個以上のアルケニル基を有するオルガノポリシロキサン、Si-H基を2個以上有するオルガノハイドロジェンポリシロキサン、熱伝導性充填材、白金族金属系硬化触媒を含み、熱伝導性充填材として、重質炭酸カルシウムを含む熱伝導性シリコーン組成物が提供されている(特許文献1)。しかしながら、シリコーンゴムは熱劣化により発生する低分子シロキサンが電子機器の発熱によって揮発し、アウトガスとなることで電子回路を短絡させる原因となる可能性がある。
Under these circumstances, organopolysiloxanes having two or more alkenyl groups in one molecule, organohydrogenpolysiloxanes having two or more Si—H groups, thermally conductive fillers, and platinum group metal curing catalysts and, as a thermally conductive filler, a thermally conductive silicone composition containing ground calcium carbonate is provided (Patent Document 1). However, in silicone rubber, low-molecular-weight siloxane generated by heat deterioration volatilizes due to heat generation of electronic devices, and outgassing may cause short-circuiting of electronic circuits.
本発明は、上記課題を鑑み、熱伝導率に優れる熱伝導用素材組成物およびそれを架橋してなる熱伝導性素材(例えば、熱伝導性シート)を提供することを目的とする。
In view of the above problems, an object of the present invention is to provide a thermally conductive material composition with excellent thermal conductivity and a thermally conductive material (for example, a thermally conductive sheet) obtained by cross-linking it.
本発明者らは、上記課題を達成するために種々検討した結果、アクリル系エラストマー、架橋剤、熱伝導フィラーを少なくとも含む熱伝導用素材組成物、および、熱伝導用素材組成物から作製される熱伝導性素材(例えば、熱伝導性シート)が、熱伝導性に優れたものであることを見出し、本発明を完成させた。
The inventors of the present invention have made various studies to achieve the above objects, and as a result, have found a thermally conductive material composition containing at least an acrylic elastomer, a cross-linking agent, and a thermally conductive filler, and a thermally conductive material composition produced from the thermally conductive material composition. The inventors have found that a thermally conductive material (for example, a thermally conductive sheet) has excellent thermal conductivity, and completed the present invention.
本発明の態様は以下のとおりである。
項1 (a)アクリル系エラストマー、(b)架橋剤、(c)熱伝導フィラーを少なくとも含む熱伝導用素材組成物であって、前記熱伝導用素材組成物の架橋後の熱伝導率が1.0W/(m・K)以上である熱伝導用素材組成物。
項2 (a)アクリル系エラストマーは、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、およびエポキシ基を有する不飽和単量体に由来する構成単位からなる群より選択される少なくとも1種の構成単位を含有する項1記載の熱伝導用素材組成物。
項3 (b)架橋剤が、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、アジリジン化合物、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、硫黄、ジチオカルバミン酸塩化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種である項1または2記載の熱伝導用素材組成物。
項4 架橋基を有する不飽和単量体と架橋剤の組合せが、
架橋基がハロゲン基の場合、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、および硫黄からなる群より選択される少なくとも1種との組み合わせ、
架橋基がカルボキシル基の場合、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、およびアジリジン化合物からなる群より選択される少なくとも1種との組み合わせ、または
架橋基がエポキシ基の場合、有機カルボン酸アンモニウム塩化合物、ジチオカルバミン酸塩化合物、多価アミン化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種との組み合わせである項1~3のいずれかに記載の熱伝導用素材組成物。
項5 (c)熱伝導フィラーが水酸化アルミニウム、酸化アルミニウム(アルミナ)、窒化アルミニウム、窒化ホウ素、および炭化ケイ素からなる群より選択される少なくとも1種である項1~4のいずれかに記載の熱伝導用素材組成物。
項6 項1~5のいずれかに記載の熱伝導用素材組成物を架橋させてなる熱伝導性素材。 Aspects of the present invention are as follows.
Item 1 A thermally conductive material composition containing at least (a) an acrylic elastomer, (b) a cross-linking agent, and (c) a thermally conductive filler, wherein the thermally conductive material composition has a thermal conductivity of 1 after cross-linking. .0 W/(m·K) or more of the material composition for heat conduction.
Item 2 (a) The acrylic elastomer comprises a structural unit derived from an unsaturated monomer having a halogen group, a structural unit derived from an unsaturated monomer having a carboxyl group, and an unsaturated monomer having an epoxy group. Item 2. The heat conductive material composition according to Item 1, containing at least one structural unit selected from the group consisting of structural units derived from.
Item 3 (b) The cross-linking agent is a polyvalent amine compound, a polyhydrazide compound, a polyepoxy compound, a polyisocyanate compound, an aziridine compound, a triazinethiol derivative compound, an organic carboxylic acid ammonium salt compound, a metal soap, sulfur Item 1 or 2, which is at least one selected from the group consisting of , a dithiocarbamate compound, an imidazole compound, a polycarboxylic acid compound, a quaternary ammonium salt compound, and a quaternary phosphonium salt compound. material composition.
Item 4 A combination of an unsaturated monomer having a cross-linking group and a cross-linking agent is
When the cross-linking group is a halogen group, combination with at least one selected from the group consisting of a triazine thiol derivative compound, an organic carboxylate ammonium salt compound, a metal soap, and sulfur;
When the cross-linking group is a carboxyl group, it is combined with at least one selected from the group consisting of polyamine compounds, polyhydrazide compounds, polyepoxy compounds, polyisocyanate compounds, and aziridine compounds, or the cross-linking group is In the case of an epoxy group, it is selected from the group consisting of organic carboxylic acid ammonium salt compounds, dithiocarbamate compounds, polyvalent amine compounds, imidazole compounds, polycarboxylic acid compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds. Item 4. The material composition for heat conduction according to any one of Items 1 to 3, which is a combination with at least one of
Item 5 (c) The thermally conductive filler is at least one selected from the group consisting of aluminum hydroxide, aluminum oxide (alumina), aluminum nitride, boron nitride, and silicon carbide. Material composition for heat conduction.
Item 6. A thermally conductive material obtained by cross-linking the thermally conductive material composition according to any one of Items 1 to 5.
項1 (a)アクリル系エラストマー、(b)架橋剤、(c)熱伝導フィラーを少なくとも含む熱伝導用素材組成物であって、前記熱伝導用素材組成物の架橋後の熱伝導率が1.0W/(m・K)以上である熱伝導用素材組成物。
項2 (a)アクリル系エラストマーは、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、およびエポキシ基を有する不飽和単量体に由来する構成単位からなる群より選択される少なくとも1種の構成単位を含有する項1記載の熱伝導用素材組成物。
項3 (b)架橋剤が、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、アジリジン化合物、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、硫黄、ジチオカルバミン酸塩化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種である項1または2記載の熱伝導用素材組成物。
項4 架橋基を有する不飽和単量体と架橋剤の組合せが、
架橋基がハロゲン基の場合、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、および硫黄からなる群より選択される少なくとも1種との組み合わせ、
架橋基がカルボキシル基の場合、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、およびアジリジン化合物からなる群より選択される少なくとも1種との組み合わせ、または
架橋基がエポキシ基の場合、有機カルボン酸アンモニウム塩化合物、ジチオカルバミン酸塩化合物、多価アミン化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種との組み合わせである項1~3のいずれかに記載の熱伝導用素材組成物。
項5 (c)熱伝導フィラーが水酸化アルミニウム、酸化アルミニウム(アルミナ)、窒化アルミニウム、窒化ホウ素、および炭化ケイ素からなる群より選択される少なくとも1種である項1~4のいずれかに記載の熱伝導用素材組成物。
項6 項1~5のいずれかに記載の熱伝導用素材組成物を架橋させてなる熱伝導性素材。 Aspects of the present invention are as follows.
Item 1 A thermally conductive material composition containing at least (a) an acrylic elastomer, (b) a cross-linking agent, and (c) a thermally conductive filler, wherein the thermally conductive material composition has a thermal conductivity of 1 after cross-linking. .0 W/(m·K) or more of the material composition for heat conduction.
Item 2 (a) The acrylic elastomer comprises a structural unit derived from an unsaturated monomer having a halogen group, a structural unit derived from an unsaturated monomer having a carboxyl group, and an unsaturated monomer having an epoxy group. Item 2. The heat conductive material composition according to Item 1, containing at least one structural unit selected from the group consisting of structural units derived from.
Item 3 (b) The cross-linking agent is a polyvalent amine compound, a polyhydrazide compound, a polyepoxy compound, a polyisocyanate compound, an aziridine compound, a triazinethiol derivative compound, an organic carboxylic acid ammonium salt compound, a metal soap, sulfur Item 1 or 2, which is at least one selected from the group consisting of , a dithiocarbamate compound, an imidazole compound, a polycarboxylic acid compound, a quaternary ammonium salt compound, and a quaternary phosphonium salt compound. material composition.
Item 4 A combination of an unsaturated monomer having a cross-linking group and a cross-linking agent is
When the cross-linking group is a halogen group, combination with at least one selected from the group consisting of a triazine thiol derivative compound, an organic carboxylate ammonium salt compound, a metal soap, and sulfur;
When the cross-linking group is a carboxyl group, it is combined with at least one selected from the group consisting of polyamine compounds, polyhydrazide compounds, polyepoxy compounds, polyisocyanate compounds, and aziridine compounds, or the cross-linking group is In the case of an epoxy group, it is selected from the group consisting of organic carboxylic acid ammonium salt compounds, dithiocarbamate compounds, polyvalent amine compounds, imidazole compounds, polycarboxylic acid compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds. Item 4. The material composition for heat conduction according to any one of Items 1 to 3, which is a combination with at least one of
Item 5 (c) The thermally conductive filler is at least one selected from the group consisting of aluminum hydroxide, aluminum oxide (alumina), aluminum nitride, boron nitride, and silicon carbide. Material composition for heat conduction.
Item 6. A thermally conductive material obtained by cross-linking the thermally conductive material composition according to any one of Items 1 to 5.
本発明の熱伝導用素材組成物、および、これより作製される素材(例えば、シート)は熱伝導率に優れ、さらに熱伝導フィラーを担保する媒体としてアクリル系エラストマーを使用することで、シリコーンゴムが抱える課題である低分子シロキサンのような電子回路を短絡させるアウトガスの発生がない。
The thermal conductive material composition of the present invention and the material (for example, sheet) produced from it have excellent thermal conductivity. There is no outgassing that short-circuits electronic circuits like low-molecular siloxane, which is a problem faced by
<熱伝導用素材組成物>
本発明の熱伝導用素材組成物は、(a)アクリル系エラストマー、(b)架橋剤、(c)熱伝導フィラーを少なくとも含む熱伝導用素材組成物である。 <Material composition for thermal conduction>
The thermally conductive material composition of the present invention is a thermally conductive material composition containing at least (a) an acrylic elastomer, (b) a cross-linking agent, and (c) a thermally conductive filler.
本発明の熱伝導用素材組成物は、(a)アクリル系エラストマー、(b)架橋剤、(c)熱伝導フィラーを少なくとも含む熱伝導用素材組成物である。 <Material composition for thermal conduction>
The thermally conductive material composition of the present invention is a thermally conductive material composition containing at least (a) an acrylic elastomer, (b) a cross-linking agent, and (c) a thermally conductive filler.
<(a)アクリル系エラストマー>
本発明の(a)アクリル系エラストマーは、アクリル酸、アクリル酸誘導体、メタクリル酸、およびメタクリル酸誘導体からなる群より選択される少なくとも1種の単量体に由来する構成単位を有するエラストマーであれば特に限定されないが、(メタ)アクリル酸エステル単量体に由来する構成単位を少なくとも含むことが好ましい。これらの構造単位は、単独、または2種以上を組み合わせて使用することもできる。 <(a) acrylic elastomer>
The (a) acrylic elastomer of the present invention is an elastomer having structural units derived from at least one monomer selected from the group consisting of acrylic acid, acrylic acid derivatives, methacrylic acid, and methacrylic acid derivatives. Although not particularly limited, it preferably contains at least a structural unit derived from a (meth)acrylic acid ester monomer. These structural units can also be used individually or in combination of 2 or more types.
本発明の(a)アクリル系エラストマーは、アクリル酸、アクリル酸誘導体、メタクリル酸、およびメタクリル酸誘導体からなる群より選択される少なくとも1種の単量体に由来する構成単位を有するエラストマーであれば特に限定されないが、(メタ)アクリル酸エステル単量体に由来する構成単位を少なくとも含むことが好ましい。これらの構造単位は、単独、または2種以上を組み合わせて使用することもできる。 <(a) acrylic elastomer>
The (a) acrylic elastomer of the present invention is an elastomer having structural units derived from at least one monomer selected from the group consisting of acrylic acid, acrylic acid derivatives, methacrylic acid, and methacrylic acid derivatives. Although not particularly limited, it preferably contains at least a structural unit derived from a (meth)acrylic acid ester monomer. These structural units can also be used individually or in combination of 2 or more types.
<(メタ)アクリル酸エステル単量体に由来する構成単位>
(メタ)アクリル酸エステル単量体に由来する構成単位としては、特に限定されるものではなく、炭素数1~16のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位、および/または、炭素数2~8のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位を例示することができる。なお、(メタ)アクリル酸アルキルエステル単量体とは、アクリル酸アルキルエステル単量体、または、メタクリル酸アルキルエステル単量体を意味し、(メタ)アクリル酸アルコキシアルキルエステル単量体とは、アクリル酸アルコキシアルキルエステル単量体、または、メタクリル酸アルコキシアルキルエステル単量体を意味する。 <Structural Unit Derived from (Meth)Acrylic Acid Ester Monomer>
Structural units derived from (meth)acrylic acid ester monomers are not particularly limited, and structural units derived from (meth)acrylic acid alkyl ester monomers having an alkyl group having 1 to 16 carbon atoms. and/or a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkoxyalkyl group having 2 to 8 carbon atoms. The (meth)acrylic acid alkyl ester monomer means an acrylic acid alkyl ester monomer or a methacrylic acid alkyl ester monomer, and the (meth)acrylic acid alkoxyalkyl ester monomer means Means an alkoxyalkyl acrylate monomer or an alkoxyalkyl methacrylate monomer.
(メタ)アクリル酸エステル単量体に由来する構成単位としては、特に限定されるものではなく、炭素数1~16のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位、および/または、炭素数2~8のアルコキシアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位を例示することができる。なお、(メタ)アクリル酸アルキルエステル単量体とは、アクリル酸アルキルエステル単量体、または、メタクリル酸アルキルエステル単量体を意味し、(メタ)アクリル酸アルコキシアルキルエステル単量体とは、アクリル酸アルコキシアルキルエステル単量体、または、メタクリル酸アルコキシアルキルエステル単量体を意味する。 <Structural Unit Derived from (Meth)Acrylic Acid Ester Monomer>
Structural units derived from (meth)acrylic acid ester monomers are not particularly limited, and structural units derived from (meth)acrylic acid alkyl ester monomers having an alkyl group having 1 to 16 carbon atoms. and/or a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkoxyalkyl group having 2 to 8 carbon atoms. The (meth)acrylic acid alkyl ester monomer means an acrylic acid alkyl ester monomer or a methacrylic acid alkyl ester monomer, and the (meth)acrylic acid alkoxyalkyl ester monomer means Means an alkoxyalkyl acrylate monomer or an alkoxyalkyl methacrylate monomer.
<(メタ)アクリル酸アルキルエステル単量体に由来する構成単位>
(メタ)アクリル酸アルキルエステル単量体に由来する構成単位は、炭素数1~16のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることが好ましく、炭素数1~8のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることがより好ましく、炭素数1~6のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることがさらに好ましい。 <Structural unit derived from (meth)acrylic acid alkyl ester monomer>
The structural unit derived from a (meth)acrylic acid alkyl ester monomer is preferably a structural unit derived from a (meth)acrylic acid alkyl ester monomer having an alkyl group having 1 to 16 carbon atoms, and the number of carbon atoms It is more preferably a structural unit derived from a (meth)acrylic acid alkyl ester monomer having an alkyl group of 1 to 8, and a (meth)acrylic acid alkyl ester monomer having an alkyl group of 1 to 6 carbon atoms. Structural units derived from are more preferred.
(メタ)アクリル酸アルキルエステル単量体に由来する構成単位は、炭素数1~16のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることが好ましく、炭素数1~8のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることがより好ましく、炭素数1~6のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位であることがさらに好ましい。 <Structural unit derived from (meth)acrylic acid alkyl ester monomer>
The structural unit derived from a (meth)acrylic acid alkyl ester monomer is preferably a structural unit derived from a (meth)acrylic acid alkyl ester monomer having an alkyl group having 1 to 16 carbon atoms, and the number of carbon atoms It is more preferably a structural unit derived from a (meth)acrylic acid alkyl ester monomer having an alkyl group of 1 to 8, and a (meth)acrylic acid alkyl ester monomer having an alkyl group of 1 to 6 carbon atoms. Structural units derived from are more preferred.
炭素数1~16のアルキル基を有する(メタ)アクリル酸アルキルエステル単量体に由来する構成単位としては、例えば、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸n-プロピル、(メタ)アクリル酸イソプロピル、(メタ)アクリル酸n-ブチル、(メタ)アクリル酸イソブチル、(メタ)アクリル酸n-ペンチル、(メタ)アクリル酸n-ヘキシル、(メタ)アクリル酸n-ヘプチル、(メタ)アクリル酸n-オクチル、(メタ)アクリル酸2-エチルヘキシル、(メタ)アクリル酸シクロヘキシル、(メタ)アクリル酸n-デシル、(メタ)アクリル酸イソデシル、(メタ)アクリル酸n-ドデシル、(メタ)アクリル酸n-ラウリル、(メタ)アクリル酸n-オクタデシル、(メタ)アクリル酸イソデシル等の(メタ)アクリル酸アルキルエステル単量体に由来する構成単位等を例示することができる。これらは、単独、または2種以上を組み合わせて使用できる。中でも、(メタ)アクリル酸メチル、(メタ)アクリル酸エチル、(メタ)アクリル酸n-ブチル、(メタ)アクリル酸2-エチルへキシルに由来する構成単位であることが好ましい。
Structural units derived from (meth)acrylic acid alkyl ester monomers having an alkyl group having 1 to 16 carbon atoms include, for example, methyl (meth)acrylate, ethyl (meth)acrylate, (meth)acrylic acid n -propyl, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-(meth)acrylate -heptyl, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth)acrylate, n-(meth)acrylate -Dodecyl, n-lauryl (meth)acrylate, n-octadecyl (meth)acrylate, isodecyl (meth)acrylate, etc. Structural units derived from (meth)acrylic acid alkyl ester monomers can be exemplified. can. These can be used singly or in combination of two or more. Among them, structural units derived from methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, and 2-ethylhexyl (meth)acrylate are preferred.
<(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位>
(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位としては、炭素数2~8のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位を含むことが好ましく、炭素数2~6のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位であることがより好ましく、炭素数2~4のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位であることがさらに好ましい。 <Structural Unit Derived from (Meth)Acrylic Acid Alkoxyalkyl Ester Monomer>
The structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer preferably contains a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkyl group having 2 to 8 carbon atoms. , It is more preferably a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkyl group having 2 to 6 carbon atoms, and an alkoxy (meth)acrylate having an alkyl group having 2 to 4 carbon atoms Structural units derived from alkyl ester monomers are more preferred.
(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位としては、炭素数2~8のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位を含むことが好ましく、炭素数2~6のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位であることがより好ましく、炭素数2~4のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位であることがさらに好ましい。 <Structural Unit Derived from (Meth)Acrylic Acid Alkoxyalkyl Ester Monomer>
The structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer preferably contains a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkyl group having 2 to 8 carbon atoms. , It is more preferably a structural unit derived from a (meth)acrylic acid alkoxyalkyl ester monomer having an alkyl group having 2 to 6 carbon atoms, and an alkoxy (meth)acrylate having an alkyl group having 2 to 4 carbon atoms Structural units derived from alkyl ester monomers are more preferred.
炭素数2~8のアルキル基を有する(メタ)アクリル酸アルコキシアルキルエステル単量体に由来する構成単位としては、例えば、(メタ)アクリル酸メトキシメチル、(メタ)アクリル酸メトキシエチル、(メタ)アクリル酸エトキシメチル、(メタ)アクリル酸2-エトキシエチル、(メタ)アクリル酸2-プロポキシエチル、(メタ)アクリル酸2-ブトキシエチル、(メタ)アクリル酸2-メトキシプロピル、(メタ)アクリル酸2-エトキシプロピル、(メタ)アクリル酸3-メトキシプロピル、(メタ)アクリル酸3-エトキシプロピル、(メタ)アクリル酸4-メトキシブチル、(メタ)アクリル酸4-エトキシブチル等の(メタ)アクリル酸アルコキシエステル単量体に由来する構成単位等を例示することができる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of structural units derived from (meth)acrylic acid alkoxyalkyl ester monomers having an alkyl group having 2 to 8 carbon atoms include methoxymethyl (meth)acrylate, methoxyethyl (meth)acrylate, and (meth)acrylate. Ethoxymethyl acrylate, 2-ethoxyethyl (meth)acrylate, 2-propoxyethyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, 2-methoxypropyl (meth)acrylate, (meth)acrylic acid (Meth)acryl such as 2-ethoxypropyl, 3-methoxypropyl (meth)acrylate, 3-ethoxypropyl (meth)acrylate, 4-methoxybutyl (meth)acrylate and 4-ethoxybutyl (meth)acrylate Structural units derived from acid alkoxy ester monomers can be exemplified. These can be used singly or in combination of two or more.
(a)アクリル系エラストマーの全構成単位に対する(メタ)アクリル酸エステル単量体に由来する構成単位の含有量は、下限としては50質量%以上であることが好ましく、60質量%以上であることがより好ましく、70質量%以上であることがさらに好ましい。上限としては99.5質量%以下であることが好ましく、99質量%以下であることがより好ましく、98.5質量%以下であることがさらに好ましい。
(a) The content of structural units derived from (meth)acrylic acid ester monomers relative to all structural units of the acrylic elastomer is preferably 50% by mass or more as a lower limit, and 60% by mass or more. is more preferable, and 70% by mass or more is even more preferable. The upper limit is preferably 99.5% by mass or less, more preferably 99% by mass or less, and even more preferably 98.5% by mass or less.
<架橋基を有する不飽和単量体に由来する構成単位>
また、本発明の(a)アクリル系エラストマーは架橋基を有する不飽和単量体に由来する構成単位を含んでいてもよく、例えば、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、エポキシ基を有する不飽和単量体に由来する構成単位が挙げられる。すなわち、(a)アクリル系エラストマーは、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、およびエポキシ基を有する不飽和単量体に由来する構成単位からなる群より選択される少なくとも1種の構成単位を含有することが好ましく、カルボキシル基を有する不飽和単量体に由来する構成単位を含有することがより好ましい。これらは、単独、または2種以上を組み合わせて使用することもできる。 <Structural Unit Derived from Unsaturated Monomer Having Crosslinking Group>
In addition, the (a) acrylic elastomer of the present invention may contain a structural unit derived from an unsaturated monomer having a cross-linking group. For example, a structural unit derived from an unsaturated monomer having a halogen group, Structural units derived from unsaturated monomers having a carboxyl group and structural units derived from unsaturated monomers having an epoxy group can be mentioned. That is, (a) the acrylic elastomer comprises a structural unit derived from an unsaturated monomer having a halogen group, a structural unit derived from an unsaturated monomer having a carboxyl group, and an unsaturated monomer having an epoxy group. It preferably contains at least one structural unit selected from the group consisting of structural units derived from and more preferably contains a structural unit derived from an unsaturated monomer having a carboxyl group. These can also be used individually or in combination of 2 or more types.
また、本発明の(a)アクリル系エラストマーは架橋基を有する不飽和単量体に由来する構成単位を含んでいてもよく、例えば、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、エポキシ基を有する不飽和単量体に由来する構成単位が挙げられる。すなわち、(a)アクリル系エラストマーは、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、およびエポキシ基を有する不飽和単量体に由来する構成単位からなる群より選択される少なくとも1種の構成単位を含有することが好ましく、カルボキシル基を有する不飽和単量体に由来する構成単位を含有することがより好ましい。これらは、単独、または2種以上を組み合わせて使用することもできる。 <Structural Unit Derived from Unsaturated Monomer Having Crosslinking Group>
In addition, the (a) acrylic elastomer of the present invention may contain a structural unit derived from an unsaturated monomer having a cross-linking group. For example, a structural unit derived from an unsaturated monomer having a halogen group, Structural units derived from unsaturated monomers having a carboxyl group and structural units derived from unsaturated monomers having an epoxy group can be mentioned. That is, (a) the acrylic elastomer comprises a structural unit derived from an unsaturated monomer having a halogen group, a structural unit derived from an unsaturated monomer having a carboxyl group, and an unsaturated monomer having an epoxy group. It preferably contains at least one structural unit selected from the group consisting of structural units derived from and more preferably contains a structural unit derived from an unsaturated monomer having a carboxyl group. These can also be used individually or in combination of 2 or more types.
ハロゲン基を有する不飽和単量体に由来する構成単位として、ハロゲン基としては、活性塩素基、活性臭素基、活性ヨウ素基などが挙げられるが、本発明においては活性塩素基を有する不飽和単量体に由来する構成単位であることが好ましく、具体的には、例えば、クロロ酢酸ビニル、2-クロロプロピオン酸ビニル、およびクロロ酢酸アリルなどの活性塩素基含有飽和カルボン酸の不飽和アルコールエステル;(メタ)アクリル酸クロロメチル、(メタ)アクリル酸1-クロロエチル、(メタ)アクリル酸2-クロロエチル、(メタ)アクリル酸1,2-ジクロロエチル、(メタ)アクリル酸2-クロロプロピル、(メタ)アクリル酸3-クロロプロピル、および(メタ)アクリル酸2,3-ジクロロプロピルなどの(メタ)アクリル酸クロロアルキルエステル;(メタ)アクリル酸2-(クロロアセトキシ)エチル、(メタ)アクリル酸2-(クロロアセトキシ)プロピル、(メタ)アクリル酸3-(クロロアセトキシ)プロピル、および(メタ)アクリル酸3-(ヒドロキシクロロアセトキシ)プロピルなどの(メタ)アクリル酸クロロアシロキシアルキルエステル;(メタ)アクリル酸2-(クロロアセチルカルバモイルオキシ)エチル、および(メタ)アクリル酸3-(クロロアセチルカルバモイルオキシ)プロピルの(メタ)アクリル酸(クロロアセチルカルバモイルオキシ)アルキルエステル;クロロメチルビニルエーテル、2-クロロエチルビニルエーテル、3-クロロプロピルビニルエーテル、2-クロロエチルアリルエーテル、および3-クロロプロピルアリルエーテルなどの活性塩素基含有不飽和エーテル;2-クロロエチルビニルケトン、3-クロロプロピルビニルケトン、および2-クロロエチルアリルケトンなどの活性塩素基含有不飽和ケトン;p-クロロメチルスチレン、m-クロロメチルスチレン、o-クロロメチルスチレン、およびp-クロロメチル-α-メチルスチレンなどのクロロメチル基含有芳香族ビニル化合物;N-クロロメチル(メタ)アクリルアミドなどの活性塩素基含有不飽和アミド;3-(ヒドロキシクロロアセトキシ)プロピルアリルエーテル、p-ビニルベンジルクロロ酢酸エステルなどのクロロアセチル基含有不飽和単量体に由来する構成単位が挙げられる。これらは単独、または、2種以上を組み合わせて使用することができる。
Examples of structural units derived from unsaturated monomers having a halogen group include an active chlorine group, an active bromine group, an active iodine group, and the like. It is preferably a structural unit derived from a mer, specifically, for example, unsaturated alcohol esters of saturated carboxylic acids containing active chlorine groups such as vinyl chloroacetate, vinyl 2-chloropropionate, and allyl chloroacetate; Chloromethyl (meth) acrylate, 1-chloroethyl (meth) acrylate, 2-chloroethyl (meth) acrylate, 1,2-dichloroethyl (meth) acrylate, 2-chloropropyl (meth) acrylate, (meth) ) chloroalkyl (meth)acrylates such as 3-chloropropyl acrylate and 2,3-dichloropropyl (meth)acrylate; 2-(chloroacetoxy)ethyl (meth)acrylate, 2 (meth)acrylic acid - (meth)acrylate chloroacyloxyalkyl esters such as (chloroacetoxy)propyl, 3-(chloroacetoxy)propyl (meth)acrylate, and 3-(hydroxychloroacetoxy)propyl (meth)acrylate; (Meth)acrylic acid (chloroacetylcarbamoyloxy)alkyl esters of 2-(chloroacetylcarbamoyloxy)ethyl acrylate and 3-(chloroacetylcarbamoyloxy)propyl (meth)acrylate; chloromethyl vinyl ether, 2-chloroethyl Active chlorine group-containing unsaturated ethers such as vinyl ether, 3-chloropropyl vinyl ether, 2-chloroethyl allyl ether, and 3-chloropropyl allyl ether; 2-chloroethyl vinyl ketone, 3-chloropropyl vinyl ketone, and 2-chloro Active chlorine group-containing unsaturated ketones such as ethyl allyl ketone; chloromethyl group-containing aromatic vinyls such as p-chloromethylstyrene, m-chloromethylstyrene, o-chloromethylstyrene, and p-chloromethyl-α-methylstyrene Compounds; active chlorine group-containing unsaturated amides such as N-chloromethyl (meth)acrylamide; 3-(hydroxychloroacetoxy) propyl allyl ether, p-vinylbenzyl chloroacetic acid esters and other unsaturated monomers containing chloroacetyl groups structural units derived from These can be used alone or in combination of two or more.
カルボキシル基を有する不飽和単量体に由来する構成単位としては、例えば、メタクリル酸、アクリル酸、クロトン酸、2-ペンテン酸、桂皮酸などのエチレン性不飽和モノカルボン酸類に由来する構成単位、フマル酸、マレイン酸、イタコン酸などのエチレン性不飽和ジカルボン酸類に由来する構成単位およびフマル酸モノメチル、フマル酸モノエチル、フマル酸モノプロピル、フマル酸モノブチル、フマル酸モノヘキシル、フマル酸モノオクチル等のフマル酸モノアルキルエステル、マレイン酸モノメチル、マレイン酸モノエチル、マレイン酸モノプロピル、マレイン酸モノブチル、マレイン酸モノペンチル、マレイン酸モノデシル等のマレイン酸モノアルキルエステル、イタコン酸モノメチル、イタコン酸モノエチル、イタコン酸モノプロピル、イタコン酸モノブチル等のイタコン酸モノアルキルエステルなどのエチレン性不飽和ジカルボン酸モノエステル類に由来する構成単位を挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Structural units derived from unsaturated monomers having a carboxyl group include, for example, methacrylic acid, acrylic acid, crotonic acid, 2-pentenoic acid, structural units derived from ethylenically unsaturated monocarboxylic acids such as cinnamic acid, structural units derived from ethylenically unsaturated dicarboxylic acids such as fumaric acid, maleic acid and itaconic acid; Acid monoalkyl esters, maleic acid monoalkyl esters such as monomethyl maleate, monoethyl maleate, monopropyl maleate, monobutyl maleate, monopentyl maleate, monodecyl maleate, monomethyl itaconate, monoethyl itaconate, monopropyl itaconate and structural units derived from ethylenically unsaturated dicarboxylic acid monoesters such as itaconic acid monoalkyl esters such as monobutyl itaconate. These can be used singly or in combination of two or more.
エポキシ基を有する不飽和単量体に由来する構成単位としては、例えば、(メタ)アクリル酸グリシジルなどのエポキシ基含有(メタ)アクリル酸エステルに由来する構成単位、p-ビニルベンジルグリシジルエーテルなどのエポキシ基含有スチレンに由来する構成単位、アリルグリシジルエーテルおよびビニルグリシジルエーテル、3,4-エポキシ-1-ペンテン、3,4-エポキシ-1-ブテン、4,5-エポキシ-2-ペンテン、4-ビニルシクロヘキシルグリシジルエーテル、シクロヘキセニルメチルグリシジルエーテル、3,4-エポキシ-1-ビニルシクロヘキセンおよびアリルフェニルグリシジルエーテルなどのエポキシ基含有エーテルに由来する構成単位が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of structural units derived from unsaturated monomers having epoxy groups include structural units derived from epoxy group-containing (meth)acrylic acid esters such as glycidyl (meth)acrylate, p-vinylbenzyl glycidyl ether and the like. Structural units derived from epoxy group-containing styrene, allyl glycidyl ether and vinyl glycidyl ether, 3,4-epoxy-1-pentene, 3,4-epoxy-1-butene, 4,5-epoxy-2-pentene, 4- Structural units derived from epoxy group-containing ethers such as vinylcyclohexylglycidyl ether, cyclohexenylmethylglycidyl ether, 3,4-epoxy-1-vinylcyclohexene and allylphenylglycidyl ether can be mentioned. These can be used singly or in combination of two or more.
(a)アクリル系エラストマーの全構成単位に対する架橋基を有する不飽和単量体に由来する構成単位の含有量は、下限として0.1質量%以上であることが好ましく、0.3質量%以上であることがより好ましく、0.5質量%以上であることがさらに好ましい。上限として10質量%以下であることが好ましく、5質量%以下であることがより好ましく、2.5質量%以下であることがさらに好ましい。また、好ましい範囲としては、0.1~10質量%、0.1~5質量%、0.1~2.5質量%、0.3~10質量%、0.3~5質量%、0.3~2.5質量%、0.5~10質量%、0.5~5質量%、0.5~2.5質量%が挙げられる。架橋基を有する不飽和単量体由来の構成単位が上記の範囲であることにより、強度や圧縮永久歪性等の物性、および加工性の点で好ましい。
(a) The content of structural units derived from unsaturated monomers having cross-linking groups in all structural units of the acrylic elastomer is preferably 0.1% by mass or more as a lower limit, and 0.3% by mass or more. and more preferably 0.5% by mass or more. The upper limit is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 2.5% by mass or less. Further, the preferred range is 0.1 to 10% by mass, 0.1 to 5% by mass, 0.1 to 2.5% by mass, 0.3 to 10% by mass, 0.3 to 5% by mass, 0 .3 to 2.5% by mass, 0.5 to 10% by mass, 0.5 to 5% by mass, and 0.5 to 2.5% by mass. When the structural unit derived from the unsaturated monomer having a cross-linking group is within the above range, it is preferable in terms of physical properties such as strength and compression set, and workability.
<その他の共重合性単量体に由来する構成単位>
(a)アクリル系エラストマーには、本発明の趣旨を逸脱しない限り、上記以外の共重合性単量体に由来する構成単位を含有してもよい。上記以外の共重合性単量体としては、例えば、エチレン性不飽和ニトリル系単量体、(メタ)アクリルアミド系単量体、芳香族ビニル系単量体、共役ジエン系単量体、非共役ジエン系単量体、その他のオレフィン系単量体等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。 <Structural units derived from other copolymerizable monomers>
(a) The acrylic elastomer may contain constitutional units derived from copolymerizable monomers other than those described above, as long as it does not deviate from the scope of the present invention. Examples of copolymerizable monomers other than the above include ethylenically unsaturated nitrile-based monomers, (meth)acrylamide-based monomers, aromatic vinyl-based monomers, conjugated diene-based monomers, non-conjugated Diene-based monomers, other olefin-based monomers, and the like are included. These can be used singly or in combination of two or more.
(a)アクリル系エラストマーには、本発明の趣旨を逸脱しない限り、上記以外の共重合性単量体に由来する構成単位を含有してもよい。上記以外の共重合性単量体としては、例えば、エチレン性不飽和ニトリル系単量体、(メタ)アクリルアミド系単量体、芳香族ビニル系単量体、共役ジエン系単量体、非共役ジエン系単量体、その他のオレフィン系単量体等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。 <Structural units derived from other copolymerizable monomers>
(a) The acrylic elastomer may contain constitutional units derived from copolymerizable monomers other than those described above, as long as it does not deviate from the scope of the present invention. Examples of copolymerizable monomers other than the above include ethylenically unsaturated nitrile-based monomers, (meth)acrylamide-based monomers, aromatic vinyl-based monomers, conjugated diene-based monomers, non-conjugated Diene-based monomers, other olefin-based monomers, and the like are included. These can be used singly or in combination of two or more.
エチレン性不飽和ニトリル系単量体としては、例えば、アクリロニトリル、メタクリロニトリル、α-メトキシアクリロニトリル、シアン化ビニリデン等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of ethylenically unsaturated nitrile-based monomers include acrylonitrile, methacrylonitrile, α-methoxyacrylonitrile, and vinylidene cyanide. These can be used singly or in combination of two or more.
(メタ)アクリルアミド系単量体としては、例えば、アクリルアミド、メタクリルアミド、ジアセトンアクリルアミド、ジアセトンメタクリルアミド、N-ブトキシメチルアクリルアミド、N-ブトキシメチルメタクリルアミド、N-ブトキシエチルアクリルアミド、N-ブトキシエチルメタクリルアミド、N-メトキシメチルアクリルアミド、N-メトキシメチルメタクリルアミド、N-プロピオキシメチルアクリルアミド、N-プロピオキシメチルメタクリルアミド、N-メチルアクリルアミド、N-メチルメタクリルアミド、N,N-ジメチルアクリルアミド、N,N-ジメチルメタクリルアミド、N,N-ジエチルアクリルアミド、N,N-ジエチルメタクリルアミド、N-メチロールアクリルアミド、N-メチロールメタクリルアミド、エタクリルアミド、クロトンアミド、ケイ皮酸アミド、マレインジアミド、イタコンジアミド、メチルマレインアミド、メチルイタコンアミド、マレインイミド、イタコンイミド等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
(Meth)acrylamide-based monomers include, for example, acrylamide, methacrylamide, diacetoneacrylamide, diacetonemethacrylamide, N-butoxymethylacrylamide, N-butoxymethylmethacrylamide, N-butoxyethylacrylamide, N-butoxyethyl methacrylamide, N-methoxymethylacrylamide, N-methoxymethylmethacrylamide, N-propioxymethylacrylamide, N-propioxymethylmethacrylamide, N-methylacrylamide, N-methylmethacrylamide, N,N-dimethylacrylamide, N , N-dimethylmethacrylamide, N,N-diethylacrylamide, N,N-diethylmethacrylamide, N-methylolacrylamide, N-methylolmethacrylamide, ethacrylamide, crotonamide, cinnamic acid amide, malediamide, itacondiamide, methyl maleamide, methylitaconamide, maleimide, itaconimide and the like. These can be used singly or in combination of two or more.
芳香族ビニル系単量体としては、例えば、スチレン、α-メチルスチレン、o-メチルスチレン、p-メチルスチレン、o-エチルスチレン、p-エチルスチレン、α-フルオロスチレン、p-トリフルオロメチルスチレン、p-メトキシスチレン、p-アミノスチレン、p-ジメチルアミノスチレン、p-アセトキシスチレン、スチレンスルホン酸あるいはその塩、α-ビニルナフタレン、1-ビニルナフタレン-4-スルホン酸あるいはその塩、2-ビニルフルオレン、2-ビニルピリジン、4-ビニルピリジン、ジビニルベンゼン、ジイソプロペニルベンゼン、ビニルベンジルクロライド等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of aromatic vinyl monomers include styrene, α-methylstyrene, o-methylstyrene, p-methylstyrene, o-ethylstyrene, p-ethylstyrene, α-fluorostyrene and p-trifluoromethylstyrene. , p-methoxystyrene, p-aminostyrene, p-dimethylaminostyrene, p-acetoxystyrene, styrenesulfonic acid or its salts, α-vinylnaphthalene, 1-vinylnaphthalene-4-sulfonic acid or its salts, 2-vinyl fluorene, 2-vinylpyridine, 4-vinylpyridine, divinylbenzene, diisopropenylbenzene, vinylbenzyl chloride and the like. These can be used singly or in combination of two or more.
共役ジエン系単量体としては、例えば、1,3-ブタジエン、2-メチル-1,3-ブタジエン、2-クロロ-1,3-ブタジエン、1,2-ジクロロ-1,3-ブタジエン、2,3-ジクロロ-1,3-ブタジエン、2,3-ジメチル-1,3-ブタジエン、2-ネオペンチル-1,3-ブタジエン、2-ブロモ-1,3-ブタジエン、2-シアノ-1,3-ブタジエン、1,3-ペンタジエン、1,3-ヘキサジエン、クロロプレン、ピペリレン等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene, 2-chloro-1,3-butadiene, 1,2-dichloro-1,3-butadiene, 2 ,3-dichloro-1,3-butadiene, 2,3-dimethyl-1,3-butadiene, 2-neopentyl-1,3-butadiene, 2-bromo-1,3-butadiene, 2-cyano-1,3 -butadiene, 1,3-pentadiene, 1,3-hexadiene, chloroprene, piperylene and the like. These can be used singly or in combination of two or more.
非共役ジエン系単量体としては、例えば、1,4-ペンタジエン、1,4-ヘキサジエン、エチリデンノルボルネン、ノルボルナジエン、ジシクロペンタジエン等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Examples of non-conjugated diene-based monomers include 1,4-pentadiene, 1,4-hexadiene, ethylidenenorbornene, norbornadiene, dicyclopentadiene and the like. These can be used singly or in combination of two or more.
その他のオレフィン系単量体としては、例えば、アクリル酸ジシクロペンタジエニル、メタクリル酸ジシクロペンタジエニルメタクリレート、アクリル酸ジシクロペンタジエニルエチル、メタクリル酸ジシクロペンタジエニルエチル等のエステル類、エチレン、プロピレン、塩化ビニル、塩化ビニリデン、1,2-ジクロロエチレン、酢酸ビニル、フッ化ビニル、フッ化ビニリデン、1,2-ジフルオロエチレン、臭化ビニル、臭化ビニリデン、1,2-ジブロモエチレン、エチルビニルエーテル、ブチルビニルエーテル等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Other olefinic monomers include esters such as dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, dicyclopentadienylethyl acrylate, and dicyclopentadienylethyl methacrylate. , ethylene, propylene, vinyl chloride, vinylidene chloride, 1,2-dichloroethylene, vinyl acetate, vinyl fluoride, vinylidene fluoride, 1,2-difluoroethylene, vinyl bromide, vinylidene bromide, 1,2-dibromoethylene, Examples include ethyl vinyl ether and butyl vinyl ether. These can be used singly or in combination of two or more.
(a)アクリル系エラストマーの全構成単位に対するその他の共重合性単量体に由来する構成単位の含有量は、10質量%以下であることが好ましく、5質量%以下であることがより好ましく、2質量%以下であることがさらに好ましい。
(a) The content of structural units derived from other copolymerizable monomers relative to all structural units of the acrylic elastomer is preferably 10% by mass or less, more preferably 5% by mass or less, It is more preferably 2% by mass or less.
本発明の(a)アクリル系エラストマーにおいて、その構成単位の含有量については、得られた重合体の核磁気共鳴スペクトルにより決定することができる。
In the (a) acrylic elastomer of the present invention, the content of the structural units can be determined by the nuclear magnetic resonance spectrum of the obtained polymer.
<(a)アクリル系エラストマーの製造方法>
本発明で用いる(a)アクリル系エラストマーは、それぞれ各種単量体を重合することで製造することができ、使用する単量体はいずれも市販品であってよく、特に制約はない。 <(a) Method for producing acrylic elastomer>
The (a) acrylic elastomer used in the present invention can be produced by polymerizing various monomers, and the monomers used may be commercially available products without any particular restrictions.
本発明で用いる(a)アクリル系エラストマーは、それぞれ各種単量体を重合することで製造することができ、使用する単量体はいずれも市販品であってよく、特に制約はない。 <(a) Method for producing acrylic elastomer>
The (a) acrylic elastomer used in the present invention can be produced by polymerizing various monomers, and the monomers used may be commercially available products without any particular restrictions.
重合反応の形態(重合工程)としては、乳化重合法、懸濁重合法、塊状重合法、および溶液重合法のいずれも用いることができるが、重合反応の制御の容易性などの点から、従来公知のアクリル系エラストマーの製造法として一般的に用いられている常圧下での乳化重合法によるのが好ましい。
As the form of polymerization reaction (polymerization step), any of emulsion polymerization method, suspension polymerization method, bulk polymerization method, and solution polymerization method can be used. Emulsion polymerization under normal pressure, which is generally used as a method for producing known acrylic elastomers, is preferred.
乳化重合による重合の場合には、通常の方法を用いればよく、重合開始剤、乳化剤、連鎖移動剤、重合停止剤等は一般的に使用される従来公知のものが使用できる。
In the case of polymerization by emulsion polymerization, a conventional method may be used, and generally used conventionally known polymerization initiators, emulsifiers, chain transfer agents, polymerization terminators, etc. can be used.
本発明で用いられる乳化剤は特に限定されず、乳化重合法おいて一般的に用いられるノニオン性乳化剤およびアニオン性乳化剤等を使用することができる。ノニオン乳化剤としては、例えば、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルコールエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン多環フェニルエーテル、ポリオキシアルキレンアルキルエーテル、ソルビタン脂肪酸エステル、ポリオキシエチレン脂肪酸エステルおよびポリオキシエチレンソルビタン脂肪酸エステル等が挙げられ、アニオン性乳化剤としては、アルキルベンゼンスルホン酸塩、アルキル硫酸エステル塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシアルキレンアルキルエーテルリン酸エステルまたはその塩、脂肪酸塩等が挙げられ、これらを1種または2種以上用いてもよい。アニオン性乳化剤の代表例としてはドデシル硫酸ナトリウム、ドデシルベンゼンスルホン酸ナトリウム、ドデシル硫酸トリエタノールアミンが挙げられる。
The emulsifier used in the present invention is not particularly limited, and nonionic emulsifiers and anionic emulsifiers generally used in emulsion polymerization can be used. Examples of nonionic emulsifiers include polyoxyethylene alkyl ethers, polyoxyethylene alcohol ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene polycyclic phenyl ethers, polyoxyalkylene alkyl ethers, sorbitan fatty acid esters, polyoxyethylene fatty acid esters, and Examples include polyoxyethylene sorbitan fatty acid esters, and examples of anionic emulsifiers include alkylbenzene sulfonates, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyalkylene alkyl ether phosphates or salts thereof, and fatty acid salts. etc., and one or more of these may be used. Representative examples of anionic emulsifiers include sodium dodecyl sulfate, sodium dodecylbenzenesulfonate, and triethanolamine dodecyl sulfate.
本発明で用いられる乳化剤の使用量は乳化重合法おいて一般的に用いられる量であればよい。具体的には、(a)アクリル系エラストマーを構成する単量体100質量部に対して、0.01質量部~10質量部の範囲であり、好ましくは0.03質量部~7質量部、さらに好ましくは0.05質量部~5質量部である。単量体成分として、反応性界面活性剤を用いる場合は、乳化剤の添加は必ずしも必要でない。
The amount of the emulsifier used in the present invention may be the amount generally used in the emulsion polymerization method. Specifically, it is in the range of 0.01 parts by mass to 10 parts by mass, preferably 0.03 parts by mass to 7 parts by mass, based on 100 parts by mass of the monomer constituting the (a) acrylic elastomer. More preferably, it is 0.05 to 5 parts by mass. When using a reactive surfactant as a monomer component, addition of an emulsifier is not necessarily required.
本発明で用いられる重合開始剤は特に限定されず、乳化重合法おいて一般的に用いられる重合開始剤を使用することができる。その具体例としては、過硫酸カリウム、過硫酸ナトリウムおよび過硫酸アンモニウムなどの過硫酸塩に代表される無機系重合開始剤、2,2-ジ(4,4-ジ-(t-ブチルパーオキシ)シクロヘキシル)プロパン、1-ジ-(t-ヘキシルパーオキシ)シクロヘキサン、1,1-ジ-(t-ブチルパーオキシ)シクロヘキサン、4,4-ジ-(t-ブチルパーオキシ)吉草酸n-ブチル、2,2-ジ(t-ブチルパーオキシ)ブタン、t-ブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、ジイソプロピルベンゼンハイドロパーオキサイド、p-メンタンハイドロパーオキサイド、1,1,3,3-テトラメチルブチルハイドロパーオキサイド、t-ブチルクミルパーオキサイド、ジ-t-ブチルパーオキサイド、ジ-t-ヘキシルパーオキサイド、ジ(2-t-ブチルパーオキシイソプロピル)ベンゼン、ジクミルパーオキサイド、ジイソブチリルパーオキサイド、ジ(3,5,5-トリメチルヘキサノイル)パーオキサイド、ジラウロイルパーオキサイド、ジコハク酸パーオキサイド、ジベンゾイルパーオキサイド、ジ(3-メチルベンゾイル)パーオキサイド、ベンゾイル(3-メチルベンゾイル)パーオキサイド、ジイソプロピルパーオキシジカーボネート、ジ-n-プロピルパーオキシジカーボネート、ジ(4-t-ブチルシクロヘキシル)パーオキシジカーボネート、ジ(2-エチルヘキシル)パーオキシジカーボネート、ジ-sec-ブチルパーオキシジカーボネート、クミルパーオキシネオデカネート、1,1,3,3-テトラメチルブチルパーオキシネオデカネート、t-ヘキシルパーオキシネオデカネート、t-ブチルパーオキシネオデカネート、t-ヘキシルパーオキシピバレート、t-ブチルパーオキシピバレート、2,5-ジメチル-2,5-ジ(2-エチルヘキサノイルパーオキシ)ヘキサン、1,1,3,3-テトラメチルブチルパーオキシ-2-エチルヘキサネート、t-ヘキシルパーオキシ-2-エチルヘキサネート、t-ブチルパーオキシ-2-エチルヘキサネート、t-ブチルパーオキシラウレート、t-ブチルパーオキシ-3,5,5-トリメチルヘキサネート、t-ヘキシルパーオキシイソプロピルモノカーボネート、t-ブチルパーオキシイソプロピルモノカーボネート、t-ブチルパーオキシ2-エチルヘキシルモノカーボネート、2,5-ジメチル-2,5-ジ(ベンゾイルパーオキシ)ヘキサン、t-ブチルパーオキシアセテート、t-ヘキシルパーオキシベンゾエート、t-ブチルパーオキシベンゾエート、2,5-ジメチル-2,5-ジ(t-ブチルパーオキシ)ヘキサン等の有機過酸化物系の重合開始剤、ハイドロパーオキサイド、アゾビスイソブチロニトリル、4-4’-アゾビス(4-シアノ吉草酸)、2-2’-アゾビス[2-(2-イミダゾリン-2-イル)プロパン、2-2’-アゾビス(プロパン-2-カルボアミジン)2-2’-アゾビス[N-(2-カルボキシエチル)-2-メチルプロパンアミド、2-2’-アゾビス{2-[1-(2-ヒドロキシエチル)-2-イミダゾリン-2-イル]プロパン}、2-2’-アゾビス(1-イミノ-1-ピロリジノ-2-メチルプロパン)および2-2’-アゾビス{2-メチル-N-[1,1-ビス(ヒドロキシメチル)-2-ヒドロキシエチル]プロパンアミド}などのアゾ系開始剤等が挙げられる。これらの重合開始剤は、単独または2種以上組み合わせて使用することができる。
The polymerization initiator used in the present invention is not particularly limited, and polymerization initiators commonly used in emulsion polymerization can be used. Specific examples thereof include inorganic polymerization initiators represented by persulfates such as potassium persulfate, sodium persulfate and ammonium persulfate, 2,2-di(4,4-di-(t-butylperoxy) cyclohexyl)propane, 1-di-(t-hexylperoxy)cyclohexane, 1,1-di-(t-butylperoxy)cyclohexane, 4,4-di-(t-butylperoxy)n-butyl valerate , 2,2-di(t-butylperoxy)butane, t-butyl hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, p-menthane hydroperoxide, 1,1,3,3-tetramethyl Butyl hydroperoxide, t-butylcumyl peroxide, di-t-butyl peroxide, di-t-hexyl peroxide, di(2-t-butylperoxyisopropyl)benzene, dicumyl peroxide, diisobutyryl peroxide , di(3,5,5-trimethylhexanoyl) peroxide, dilauroyl peroxide, disuccinic acid peroxide, dibenzoyl peroxide, di(3-methylbenzoyl) peroxide, benzoyl(3-methylbenzoyl) peroxide , diisopropylperoxydicarbonate, di-n-propylperoxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate, di(2-ethylhexyl)peroxydicarbonate, di-sec-butylperoxydicarbonate Carbonate, cumyl peroxyneodecanate, 1,1,3,3-tetramethylbutylperoxyneodecanate, t-hexylperoxyneodecanate, t-butylperoxyneodecanate, t-hexylperoxypi Valate, t-butylperoxypivalate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa t-hexylperoxy-2-ethylhexanate, t-butylperoxy-2-ethylhexanate, t-butylperoxylaurate, t-butylperoxy-3,5,5-trimethylhexanate, t-hexyl peroxyisopropyl monocarbonate, t-butyl peroxy isopropyl monocarbonate, t-butyl peroxy 2-ethylhexyl monocarbonate, 2,5-dimethyl-2 ,5-di(benzoylperoxy)hexane, t-butylperoxyacetate, t-hexylperoxybenzoate, t-butylperoxybenzoate, 2,5-dimethyl-2,5-di(t-butylperoxy) Organic peroxide polymerization initiators such as hexane, hydroperoxide, azobisisobutyronitrile, 4-4'-azobis(4-cyanovaleric acid), 2-2'-azobis[2-(2- imidazolin-2-yl) propane, 2-2′-azobis (propane-2-carbamidine) 2-2′-azobis[N-(2-carboxyethyl)-2-methylpropanamide, 2-2′-azobis {2-[1-(2-hydroxyethyl)-2-imidazolin-2-yl]propane}, 2-2′-azobis(1-imino-1-pyrrolidino-2-methylpropane) and 2-2′- and azo initiators such as azobis {2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propanamide}. These polymerization initiators can be used alone or in combination of two or more.
本発明で用いられる重合開始剤の使用量は乳化重合法おいて一般的に用いられる量であればよい。具体的には、(a)アクリル系エラストマーを構成する単量体100質量部に対して、0.01質量部~5質量部の範囲であり、好ましくは0.015質量部~4質量部、さらに好ましくは0.02質量部~3質量部である。
The amount of the polymerization initiator used in the present invention may be the amount generally used in the emulsion polymerization method. Specifically, it is in the range of 0.01 parts by mass to 5 parts by mass, preferably 0.015 parts by mass to 4 parts by mass, based on 100 parts by mass of the monomer constituting the acrylic elastomer (a). More preferably, it ranges from 0.02 parts by mass to 3 parts by mass.
また、重合開始剤としての有機過酸化物および無機過酸化物は、還元剤と組み合わせることにより、レドックス系重合開始剤として使用することができる。組み合わせて用いる還元剤としては、特に限定されないが、硫酸第一鉄、ナフテン酸第一銅等の還元状態にある金属イオンを含有する化合物、メタンスルホン酸ナトリウム等のメタン化合物、ジメチルアニリン等のアミン化合物、アスコルビン酸およびその塩、亜硫酸およびチオ硫酸のアルカリ金属塩などの還元性を有する無機塩などが挙げられる。これらの還元剤は単独でまたは2種以上を組み合わせて使用することができる。還元剤の使用量は、(a)アクリル系エラストマーを構成する単量体100質量部に対して好ましくは0.0003~10.0質量部である。
In addition, organic peroxides and inorganic peroxides as polymerization initiators can be used as redox polymerization initiators by combining them with reducing agents. The reducing agent used in combination is not particularly limited, but compounds containing metal ions in a reduced state such as ferrous sulfate and cuprous naphthenate, methane compounds such as sodium methanesulfonate, and amines such as dimethylaniline. compounds, ascorbic acid and its salts, and reducing inorganic salts such as alkali metal salts of sulfurous acid and thiosulfate. These reducing agents can be used alone or in combination of two or more. The amount of the reducing agent used is preferably 0.0003 to 10.0 parts by weight per 100 parts by weight of the monomers constituting the (a) acrylic elastomer.
連鎖移動剤は必要に応じて用いることができる。連鎖移動剤の具体例としては、n-ヘキシルメルカプタン、n-オクチルメルカプタン、t-オクチルメルカプタン、n-ドデシルメルカプタン、t-ドデシルメルカプタン、n-ステアリルメルカプタン等のアルキルメルカプタン、2,4-ジフェニル-4-メチル-1-ペンテン、2,4-ジフェニル-4-メチル-2-ペンテン、ジメチルキサントゲンジサルファイド、ジイソプロピルキサントゲンジサルファイド等のキサントゲン化合物、ターピノレン、テトラメチルチウラムジスルフィド、テトラエチルチウラムジスルフィド、テトラメチルチウラムモノスルフィド等のチウラム系化合物、2,6-ジ-t-ブチル-4-メチルフェノール、スチレン化フェノール等のフェノール系化合物、アリルアルコール等のアリル化合物、ジクロルメタン、ジブロモメタン、四臭化炭素等のハロゲン化炭化水素化合物、α-ベンジルオキシスチレン、α-ベンジルオキシアクリロニトリル、α-ベンジルオキシアクリルアミド等のビニルエーテル、トリフェニルエタン、ペンタフェニルエタン、アクロレイン、メタアクロレイン、チオグリコール酸、チオリンゴ酸、2-エチルヘキシルチオグリコレート等が挙げられ、これらを1種または2種以上用いてもよい。これらの連鎖移動剤の量は特に限定されないが、(a)アクリル系エラストマーを構成する単量体100質量部に対して0質量部~5質量部にて使用される。
A chain transfer agent can be used as needed. Specific examples of chain transfer agents include alkylmercaptans such as n-hexylmercaptan, n-octylmercaptan, t-octylmercaptan, n-dodecylmercaptan, t-dodecylmercaptan and n-stearylmercaptan, 2,4-diphenyl-4 -methyl-1-pentene, 2,4-diphenyl-4-methyl-2-pentene, xanthogen compounds such as dimethylxanthogen disulfide, diisopropylxanthogen disulfide, terpinolene, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetramethylthiuram mono Thiuram compounds such as sulfide, phenolic compounds such as 2,6-di-t-butyl-4-methylphenol, styrenated phenol, allyl compounds such as allyl alcohol, halogens such as dichloromethane, dibromomethane, and carbon tetrabromide Hydrocarbon compounds, vinyl ethers such as α-benzyloxystyrene, α-benzyloxyacrylonitrile, α-benzyloxyacrylamide, triphenylethane, pentaphenylethane, acrolein, methacrolein, thioglycolic acid, thiomalic acid, 2-ethylhexylthio Glycolate and the like may be mentioned, and one or more of these may be used. Although the amount of these chain transfer agents is not particularly limited, they are used in an amount of 0 to 5 parts by mass with respect to 100 parts by mass of the monomers constituting the (a) acrylic elastomer.
重合停止剤としては、例えば、ヒドロキシルアミン、ヒドロキシアミン硫酸塩、ジエチルヒドロキシアミン、ヒドロキシアミンスルホン酸およびそのアルカリ金属塩、ジメチルジチオカルバミン酸ナトリウムおよびヒドロキノンなどのキノン化合物などが挙げられる。重合停止剤の使用量は、特に限定されないが、(a)アクリル系エラストマーを構成する単量体100質量部に対して0質量部~2質量部である。
Examples of the polymerization terminator include hydroxylamine, hydroxylamine sulfate, diethylhydroxyamine, hydroxylaminesulfonic acid and alkali metal salts thereof, sodium dimethyldithiocarbamate, and quinone compounds such as hydroquinone. The amount of the polymerization terminator used is not particularly limited, but is 0 to 2 parts by mass with respect to 100 parts by mass of the monomers constituting the (a) acrylic elastomer.
さらに上記の方法によって得られた重合体は、必要に応じてpH調整剤として塩基を用いることでpHを調整することができる。塩基の具体例としては、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸水素ナトリウム、アンモニア、無機アンモニウム化合物、有機アミン化合物等が挙げられる。pHの範囲はpH1~11、好ましくはpH1.5~10.5、さらに好ましくはpH2~10の範囲である。
Further, the pH of the polymer obtained by the above method can be adjusted by using a base as a pH adjuster as needed. Specific examples of bases include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium hydrogen carbonate, ammonia, inorganic ammonium compounds, organic amine compounds and the like. The pH range is pH 1-11, preferably pH 1.5-10.5, more preferably pH 2-10.
これ以外にも必要に応じて、粒径調整剤、キレート化剤、酸素捕捉剤等の重合副資材を使用することができる。
In addition to this, if necessary, secondary polymerization materials such as particle size modifiers, chelating agents, and oxygen scavengers can be used.
乳化重合は、回分式、半回分式、連続式のいずれでもよい。重合時間および重合温度は特に限定されない。使用する重合開始剤の種類等から適宜選択できるが、一般的に、重合温度は10℃~100℃であり、重合時間は0.5時間~100時間である。
Emulsion polymerization may be batch, semi-batch or continuous. Polymerization time and polymerization temperature are not particularly limited. Although it can be appropriately selected depending on the type of polymerization initiator to be used, generally, the polymerization temperature is 10° C. to 100° C. and the polymerization time is 0.5 hour to 100 hours.
上記の方法で得られた重合体を回収する工程(凝固工程)において、その方法については特に制限はなく、一般に行われている方法を採用することができる。その方法の一例として、重合液を凝固剤含有水溶液に連続的または回分的に供給する方法が挙げられ、この操作によって含水クラムが得られる。その際凝固剤を含む水溶液の温度は、単量体の種類と使用量、撹拌等による剪断力などの凝固条件の影響を受けるため、これを一律に規定することはできないが、一般的には50℃~100℃であり、60℃~100℃の範囲であることが好ましい。
In the process of recovering the polymer obtained by the above method (coagulation process), there is no particular limitation on the method, and a commonly used method can be adopted. As an example of the method, there is a method of continuously or batchwise supplying the polymerization liquid to the coagulant-containing aqueous solution, and by this operation, the water-containing crumbs are obtained. At that time, the temperature of the aqueous solution containing the coagulant is affected by the type and amount of the monomer used, the coagulation conditions such as the shear force due to stirring, etc., so it cannot be uniformly defined, but in general 50°C to 100°C, preferably 60°C to 100°C.
さらに上記の凝固工程中に老化防止剤を添加することができる。老化防止剤の具体例としてはフェノール系の酸化防止剤、アミン系の酸化防止剤、フォスファノール系の酸化防止剤、ヒンダートアミン系の老化防止剤などが挙げられる。
Furthermore, an anti-aging agent can be added during the above solidification process. Specific examples of anti-aging agents include phenol-based antioxidants, amine-based antioxidants, phosphanol-based antioxidants, and hindered amine-based anti-aging agents.
さらに上記の方法によって得られた含水クラムは、必要に応じてpH調整剤として塩基を用いることでpHを調整することができる。塩基の具体例としては、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸水素ナトリウム、アンモニア、無機アンモニウム化合物、有機アミン化合物等が挙げられる。pHの範囲はpH1~11、好ましくはpH2~10、さらに好ましくはpH4~8の範囲である。
Furthermore, the pH of the water-containing crumbs obtained by the above method can be adjusted by using a base as a pH adjuster as needed. Specific examples of bases include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium hydrogen carbonate, ammonia, inorganic ammonium compounds, organic amine compounds and the like. The pH range is pH 1-11, preferably pH 2-10, more preferably pH 4-8.
上記の方法で得られた含水クラムは、凝固剤を除去するために水洗洗浄を行なうことが好ましい(水洗洗浄工程)。水洗洗浄を全く行わないあるいは洗浄が不十分である場合、凝固剤に由来するイオン残留物が成形工程で析出してしまう恐れがある。
The wet crumbs obtained by the above method are preferably washed with water to remove the coagulant (washing step). If the washing with water is not performed at all or the washing is insufficient, there is a risk that ion residues derived from the coagulant will be precipitated during the molding process.
水洗洗浄後の含水クラムから水分を除去し乾燥する工程(乾燥工程)を経ることでアクリル系エラストマーを得ることができる。乾燥の方法としては特に限定されないが一般的にはフラッシュドライヤーや流動乾燥機などを用いて乾燥される。また、乾燥工程の前に遠心分離機等による脱水工程を経ても良い。
The acrylic elastomer can be obtained by removing water from the water-containing crumbs after washing with water and drying them (drying process). Although the drying method is not particularly limited, it is generally dried using a flash dryer, a fluidized bed dryer, or the like. Also, a dehydration step using a centrifugal separator or the like may be performed before the drying step.
このようにして製造される本発明の(a)アクリル系エラストマーの分子量範囲は、加工性の観点から、JIS K 6300に定めるムーニースコーチ試験での100℃におけるムーニー粘度(ML1+4)表示で、10~100であることが好ましく、15~90であることがより好ましく、20~80であることがさらに好ましい。
The molecular weight range of the (a) acrylic elastomer of the present invention thus produced is, from the standpoint of workability, 10 to 10 in terms of Mooney viscosity (ML1+4) at 100°C in the Mooney scorch test defined in JIS K 6300. It is preferably 100, more preferably 15-90, even more preferably 20-80.
本発明の熱伝導用素材組成物において、ポリマー成分(エラストマー成分)100質量%中の(a)アクリル系エラストマーの含有量は、好ましくは60質量%以上、より好ましくは80質量%以上、さらに好ましくは90質量%以上、特に好ましくは95質量%以上、最も好ましくは98質量%以上であり、100質量%であってもよい。これにより、良好な熱伝導率が付与できると共に、シリコーンゴムが抱える課題である低分子シロキサンのような電子回路を短絡させるアウトガスの発生を抑制できる。
In the heat-conducting material composition of the present invention, the content of (a) the acrylic elastomer in 100% by mass of the polymer component (elastomer component) is preferably 60% by mass or more, more preferably 80% by mass or more, and even more preferably 80% by mass or more. is 90% by mass or more, particularly preferably 95% by mass or more, most preferably 98% by mass or more, and may be 100% by mass. As a result, good thermal conductivity can be imparted, and outgassing that short-circuits electronic circuits, such as low-molecular-weight siloxane, which is a problem with silicone rubber, can be suppressed.
本発明の熱伝導用素材組成物において、ポリマー成分(エラストマー成分)100質量%中のシリコーンゴムの含有量は、シリコーンゴムが抱える課題である低分子シロキサンのような電子回路を短絡させるアウトガスの発生を抑制できるという理由から、好ましくは5質量%以下、より好ましくは1質量%以下、さらに好ましくは0.5質量%以下、特に好ましくは0.1質量%以下、最も好ましくは0質量%である。同様に、本発明の熱伝導用素材組成物において、ポリマー成分(エラストマー成分)100質量%中のオルガノポリシロキサンの含有量は、好ましくは5質量%以下、より好ましくは1質量%以下、さらに好ましくは0.5質量%以下、特に好ましくは0.1質量%以下、最も好ましくは0質量%である。
In the heat-conducting material composition of the present invention, the content of silicone rubber in 100% by mass of the polymer component (elastomer component) is such that outgassing that short-circuits electronic circuits such as low-molecular siloxane, which is a problem with silicone rubber, is generated. is preferably 5% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, particularly preferably 0.1% by mass or less, and most preferably 0% by mass. . Similarly, in the heat-conducting material composition of the present invention, the content of organopolysiloxane in 100% by mass of the polymer component (elastomer component) is preferably 5% by mass or less, more preferably 1% by mass or less, and even more preferably 1% by mass or less. is 0.5% by mass or less, particularly preferably 0.1% by mass or less, and most preferably 0% by mass.
熱伝導用素材組成物における各ポリマー成分の含有量については、核磁気共鳴スペクトルにより決定することができる。
The content of each polymer component in the heat-conducting material composition can be determined by nuclear magnetic resonance spectroscopy.
<(b)架橋剤>
本発明の熱伝導用素材組成物に用いる(b)架橋剤としては、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、アジリジン化合物、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、硫黄、ジチオカルバミン酸塩化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種を用いることができる。なかでも、多価アミン化合物、トリアジンチオール誘導体化合物、金属石ケン、硫黄からなる群より選択される少なくとも1種が好ましく、多価アミン化合物がより好ましい。 <(b) Crosslinking agent>
Examples of the (b) cross-linking agent used in the heat-conducting material composition of the present invention include polyamine compounds, polyhydrazide compounds, polyepoxy compounds, polyisocyanate compounds, aziridine compounds, triazinethiol derivative compounds, organic carboxylic acids, At least one selected from the group consisting of acid ammonium salt compounds, metal soaps, sulfur, dithiocarbamate compounds, imidazole compounds, polycarboxylic acid compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds. can be used. Among them, at least one selected from the group consisting of polyvalent amine compounds, triazinethiol derivative compounds, metallic soaps and sulfur is preferred, and polyvalent amine compounds are more preferred.
本発明の熱伝導用素材組成物に用いる(b)架橋剤としては、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、アジリジン化合物、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、硫黄、ジチオカルバミン酸塩化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種を用いることができる。なかでも、多価アミン化合物、トリアジンチオール誘導体化合物、金属石ケン、硫黄からなる群より選択される少なくとも1種が好ましく、多価アミン化合物がより好ましい。 <(b) Crosslinking agent>
Examples of the (b) cross-linking agent used in the heat-conducting material composition of the present invention include polyamine compounds, polyhydrazide compounds, polyepoxy compounds, polyisocyanate compounds, aziridine compounds, triazinethiol derivative compounds, organic carboxylic acids, At least one selected from the group consisting of acid ammonium salt compounds, metal soaps, sulfur, dithiocarbamate compounds, imidazole compounds, polycarboxylic acid compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds. can be used. Among them, at least one selected from the group consisting of polyvalent amine compounds, triazinethiol derivative compounds, metallic soaps and sulfur is preferred, and polyvalent amine compounds are more preferred.
トリアジンチオール誘導体化合物としては、例えば、6-トリメルカプト-s-トリアジン、2-アニリノ-4,6-ジチオール-s-トリアジン、1-ジブチルアミノ-3,5-ジメルカプトトリアジン、2-ジブチルアミノ-4,6-ジチオール-s-トリアジン、1-フェニルアミノ-3,5-ジメルカプトトリアジン、2,4,6-トリメルカプト-s-トリアジン、1-ヘキシルアミノ-3,5-ジメルカプトトリアジンなどが挙げられる。
Examples of triazinethiol derivative compounds include 6-trimercapto-s-triazine, 2-anilino-4,6-dithiol-s-triazine, 1-dibutylamino-3,5-dimercaptotriazine, 2-dibutylamino- 4,6-dithiol-s-triazine, 1-phenylamino-3,5-dimercaptotriazine, 2,4,6-trimercapto-s-triazine, 1-hexylamino-3,5-dimercaptotriazine, etc. mentioned.
有機カルボン酸アンモニウム塩化合物としては、例えば、安息香酸アンモニウム、アジピン酸アンモニウムなどが挙げられる。
Examples of organic carboxylic acid ammonium salt compounds include ammonium benzoate and ammonium adipate.
金属石ケンとしては、例えば、酢酸、プロピオン酸、カプロン酸、ラウリル酸、ステアリン酸等の炭素数8~18の脂肪酸のリチウム塩、ナトリウム塩、カリウム塩、セシウム塩が挙げられる。
Examples of metal soaps include lithium salts, sodium salts, potassium salts, and cesium salts of fatty acids having 8 to 18 carbon atoms such as acetic acid, propionic acid, caproic acid, lauric acid, and stearic acid.
硫黄化合物としては、例えば、硫黄、4,4’-ジチオモルホリンやテトラメチルチウラムジスルフィド、テトラエチルチウラムジスルフィドなどが挙げられる。
Examples of sulfur compounds include sulfur, 4,4'-dithiomorpholine, tetramethylthiuram disulfide, and tetraethylthiuram disulfide.
多価アミン化合物としては、例えば、ヘキサメチレンジアミン、ヘキサメチレンジアミンカルバメート、N,N-ジシンナミリデン-1,6-ヘキサンジアミン、テトラメチレンペンタミン、ヘキサメチレンジアミンシンナムアルデヒド付加物などの脂肪族多価アミン類;4,4-メチレンジアニリン、m-フェニレンジアミン、4,4-ジアミノジフェニルエーテル、3,4-ジアミノジフェニルエーテル、4,4-(m-フェニレンジイソプロピリデン)ジアニリン、4,4-(p-フェニレンジイソプロピリデン)ジアニリン、2,2-ビス[4-(4-アミノフェノキシ)フェニル]プロパン、4,4-ジアミノベンズアニリド、4,4-ビス(4-アミノフェノキシ)ビフェニル、m-キシリレンジアミン、p-キシリレンジアミン、1,3,5-ベンゼントリアミンなどの芳香族多価アミン類などが挙げられる。なかでも、ヘキサメチレンジアミンカルバメート、2,2-ビス[4-(4-アミノフェノキシ)フェニル]プロパン、N,N-ジシンナミリデン-1,6-ヘキサンジアミンが好ましく、ヘキサメチレンジアミンカルバメートがより好ましい。
Examples of polyvalent amine compounds include aliphatic polyvalent amines such as hexamethylenediamine, hexamethylenediamine carbamate, N,N-dicinnamylidene-1,6-hexanediamine, tetramethylenepentamine, and hexamethylenediamine cinnamaldehyde adducts. 4,4-methylenedianiline, m-phenylenediamine, 4,4-diaminodiphenyl ether, 3,4-diaminodiphenyl ether, 4,4-(m-phenylenediisopropylidene)dianiline, 4,4-(p- phenylenediisopropylidene)dianiline, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 4,4-diaminobenzanilide, 4,4-bis(4-aminophenoxy)biphenyl, m-xylylene aromatic polyvalent amines such as amines, p-xylylenediamine and 1,3,5-benzenetriamine; Among them, hexamethylenediamine carbamate, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, and N,N-dicinnamylidene-1,6-hexanediamine are preferred, and hexamethylenediamine carbamate is more preferred.
多価ヒドラジド化合物としては、例えば、イソフタル酸ジヒドラジド、テレフタル酸ジヒドラジド、フタル酸ジヒドラジド、2,6-ナフタレンジカルボン酸ジヒドラジド、ナフタレン酸ジヒドラジド、シュウ酸ジヒドラジド、マロン酸ジヒドラジド、コハク酸ジヒドラジド、グルタミン酸ジヒドラジド、アジピン酸ジヒドラジド、ピメリン酸ジヒドラジド、スベリン酸ジヒドラジド、アゼライン酸ジヒドラジド、セバシン酸ジヒドラジド、ブラッシル酸ジヒドラジド、ドデカン二酸ジヒドラジド、アセトンジカルボン酸ジヒドラジド、フマル酸ジヒドラジド、マレイン酸ジヒドラジド、イタコン酸ジヒドラジド、トリメリット酸ジヒドラジド、アコニット酸ジヒドラジド、1,3,5-ベンゼントリカルボン酸ジヒドラジド、ピロメリット酸ジヒドラジドなどが挙げられる。
Polyvalent hydrazide compounds include, for example, isophthalic acid dihydrazide, terephthalic acid dihydrazide, phthalic acid dihydrazide, 2,6-naphthalenedicarboxylic acid dihydrazide, naphthalic acid dihydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutamic acid dihydrazide, and adipine. acid dihydrazide, pimelic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, brassylic acid dihydrazide, dodecanedioic acid dihydrazide, acetonedicarboxylic acid dihydrazide, fumaric acid dihydrazide, maleic acid dihydrazide, itaconic acid dihydrazide, trimellitic acid dihydrazide, Examples include aconitic acid dihydrazide, 1,3,5-benzenetricarboxylic acid dihydrazide, and pyromellitic acid dihydrazide.
多価エポキシ化合物としては、例えば、フェノールノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、クレゾール型エポキシ化合物、ビスフェノールA型エポキシ化合物、ビスフェノールF型エポキシ化合物、臭素化ビスフェノールA型エポキシ化合物、臭素化ビスフェノールF型エポキシ化合物、水素添加ビスフェノールA型エポキシ化合物などのグリシジルエーテル型エポキシ化合物、脂環式エポキシ化合物、グリシジルエステル型エポキシ化合物、グリシジルアミン型エポキシ化合物、イソシアヌレート型エポキシ化合物などのその他の多価エポキシ化合物が挙げられる。
Polyepoxy compounds include, for example, phenol novolac type epoxy compounds, cresol novolak type epoxy compounds, cresol type epoxy compounds, bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, brominated bisphenol A type epoxy compounds, brominated bisphenol F type epoxy compounds, glycidyl ether type epoxy compounds such as hydrogenated bisphenol A type epoxy compounds, alicyclic epoxy compounds, glycidyl ester type epoxy compounds, glycidyl amine type epoxy compounds, other polyvalent epoxy compounds such as isocyanurate type epoxy compounds is mentioned.
多価イソシアナート化合物としては、例えば、2,4-トリレンジイソシアナート、2,6-トリレンジイソシアナート、4,4'-ジフェニルメタンジイソシアナート、ヘキサメチレンジイソシアナート、p-フェニレンジイソシアナート、m-フェニレンジイソシアナート、1,5-ナフチレンジイソシアナート、1,3,6-ヘキサメチレントリイソシアナート、1,6,11- ウンデカントリイソシアナート、ビシクロヘプタントリイソシアナート等が挙げられる。
Examples of polyvalent isocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, hexamethylene diisocyanate, and p-phenylene diisocyanate. , m-phenylene diisocyanate, 1,5-naphthylene diisocyanate, 1,3,6-hexamethylene triisocyanate, 1,6,11-undecane triisocyanate, bicycloheptane triisocyanate and the like.
アジリジン化合物としては、例えば、トリス- 2,4,6-(1-アジリジニル)-1,3,5-トリアジン、トリス〔1-(2-メチル)アジリジニル〕ホスフィノキシド、ヘキサ〔1-(2-メチル) アジリジニル〕トリホスファトリアジン等が挙げられる。
Examples of aziridine compounds include tris-2,4,6-(1-aziridinyl)-1,3,5-triazine, tris[1-(2-methyl)aziridinyl]phosphinoxide, hexa[1-(2-methyl ) aziridinyl]triphosphatriazine and the like.
ジチオカルバミン酸塩化合物としては、例えば、ジメチルジチオカルバミン酸、ジエチルジチオカルバミン酸、ジブチルジチオカルバミン酸、エチルフェニルジチオカルバミン酸、ジベンジルジチオカルバミン酸などのナトリウム塩、銅塩、亜鉛塩、鉄塩、テルル塩等が挙げられる。
Examples of dithiocarbamate compounds include sodium salts, copper salts, zinc salts, iron salts, tellurium salts of dimethyldithiocarbamate, diethyldithiocarbamate, dibutyldithiocarbamate, ethylphenyldithiocarbamate, dibenzyldithiocarbamate and the like. .
イミダゾール類化合物としては、例えば、1-メチルイミダゾール、1,2-ジメチルイミダゾール、1-メチル-2-エチルイミダゾール、1-ベンジル-2-メチルイミダゾール、1-ベンジル-2-エチルイミダゾール、1-ベンジル-2-エチル-5-メチルイミダゾール、1-ベンジル-2-フェニルイミダゾール、1-ベンジル-2-フェニルイミダゾール・トリメリット酸塩、1-アミノエチルイミダゾール、1-アミノエチル-2-メチルイミダゾール、1-アミノエチル-2-エチルイミダゾール、1-シアノエチル-2-メチルイミダゾール、1-シアノエチル-2-フェニルイミダゾール、1-シアノエチル-2-エチル-4-メチルイミダゾ-ル、1-シアノエチル-2-ウンデシルイミダゾール、1-シアノエチル-2-メチルイミダゾールトリメリテート、1-シアノエチル-2-フェニルイミダゾールトリメリテート、1-シアノエチル-2-エチル-4-メチルイミダゾールトリメリテート、1-シアノエチル-2-ウンデシル-イミダゾールトリメリテート、2,4-ジアミノ-6-〔2’-メチルイミダゾリル-(1)’〕エチル-s-トリアジン・イソシアヌール酸付加物、1-シアノエチル-2-フェニル-4,5-ジ-(シアノエトキシメチル)イミダゾール、N-(2-メチルイミダゾリル-1-エチル)尿素、N,N’-ビス-(2-メチルイミダゾリル-1-エチル)尿素、1-(シアノエチルアミノエチル)-2-メチルイミダゾール、N,N’-〔2-メチルイミダゾリル-(1)-エチル〕-アジボイルジアミド、N,N’-〔2-メチルイミダゾリル-(1)-エチル〕-ドデカンジオイルジアミド、N,N’-〔2-メチルイミダゾリル-(1)-エチル〕-エイコサンジオイルジアミド、2,4-ジアミノ-6-〔2’-メチルイミダゾリル-(1)’〕-エチル-s-トリアジン、2,4-ジアミノ-6-〔2’-ウンデシルイミダゾリル-(1)’〕-エチル-s-トリアジン、1-ドデシル-2-メチル-3-ベンジルイミダゾリウムクロライド、1,3-ジベンジル-2-メチルイミダゾリウムクロライド等が挙げられる。
Examples of imidazole compounds include 1-methylimidazole, 1,2-dimethylimidazole, 1-methyl-2-ethylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-ethylimidazole, 1-benzyl -2-ethyl-5-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-phenylimidazole trimellitate, 1-aminoethylimidazole, 1-aminoethyl-2-methylimidazole, 1 -aminoethyl-2-ethylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecyl imidazole, 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl-2-phenylimidazole trimellitate, 1-cyanoethyl-2-ethyl-4-methylimidazole trimellitate, 1-cyanoethyl-2-undecyl- Imidazole trimellitate, 2,4-diamino-6-[2′-methylimidazolyl-(1)′]ethyl-s-triazine isocyanuric acid adduct, 1-cyanoethyl-2-phenyl-4,5-di -(Cyanoethoxymethyl)imidazole, N-(2-methylimidazolyl-1-ethyl)urea, N,N'-bis-(2-methylimidazolyl-1-ethyl)urea, 1-(cyanoethylaminoethyl)-2 -methylimidazole, N,N'-[2-methylimidazolyl-(1)-ethyl]-aziboyldiamide, N,N'-[2-methylimidazolyl-(1)-ethyl]-dodecanedioyldiamide, N , N′-[2-methylimidazolyl-(1)-ethyl]-eicosandioyldiamide, 2,4-diamino-6-[2′-methylimidazolyl-(1)′]-ethyl-s-triazine, 2 , 4-diamino-6-[2′-undecylimidazolyl-(1)′]-ethyl-s-triazine, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 1,3-dibenzyl-2- and methylimidazolium chloride.
ポリカルボン酸化合物としては、例えば、シュウ酸、コハク酸、アジピン酸、セバシン酸、ドデカン二酸、テレフタル酸、トリメシン酸、3,4-ビス(カルボキシメチル)シクロペンタンカルボン酸などが挙げられる。
Examples of polycarboxylic acid compounds include oxalic acid, succinic acid, adipic acid, sebacic acid, dodecanedioic acid, terephthalic acid, trimesic acid, and 3,4-bis(carboxymethyl)cyclopentanecarboxylic acid.
第4級アンモニウム塩化合物としては、例えば、テトラエチルアンモニウムブロマイド、テトラブチルアンモニウムクロライド、テトラブチルアンモニウムブロマイド、テトラブチルアンモニウムアイオダイド、n-ドデシルトリメチルアンモニウムブロマイド、セチルジメチルベンジルアンモニウムクロライド、メチルセチルジベンジルアンモニウムブロマイド、セチルジメチルエチルアンモニウムブロマイド、オクタデシルトリメチルアンモニウムブロマイド、セチルピリジウムクロライド、セチルピリジウムブロマイド、1,8-ジアザ-ビシクロ(5,4,0)ウンデセン-7-メチルアンモニウムメトサルフェート、1,8-ジアザ-ビシクロ(5,4,0)ウンデセン-7-ベンジルアンモニウムクロライド、セチルトリメチルアンモニウムアルキルフェノキシポリ(エチレンオキシ)エチルホスフェート、セチルピリジウムアイオダイド、セチルピリジウムサルフェート、テトラエチルアンモニウムアセテート、トリメチルベンジルアンモニウムベンゾエート、トリメチルベンジルアンモニウムパラトルエンスルホネート、トリメチルベンジルアンモニウムボレートなどが挙げられる。
Examples of quaternary ammonium salt compounds include tetraethylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, n-dodecyltrimethylammonium bromide, cetyldimethylbenzylammonium chloride, and methylcetyldibenzylammonium bromide. , cetyldimethylethylammonium bromide, octadecyltrimethylammonium bromide, cetylpyridium chloride, cetylpyridium bromide, 1,8-diaza-bicyclo(5,4,0)undecene-7-methylammonium methosulfate, 1,8-diaza -bicyclo(5,4,0)undecene-7-benzylammonium chloride, cetyltrimethylammonium alkylphenoxypoly(ethyleneoxy)ethyl phosphate, cetylpyridium iodide, cetylpyridium sulfate, tetraethylammonium acetate, trimethylbenzylammonium benzoate, trimethylbenzylammonium p-toluenesulfonate, trimethylbenzylammonium borate and the like.
第4級ホスホニウム塩化合物としては、例えば、トリフェニルベンジルホスホニウムクロライド、トリフェニルベンジルホスホニウムブロマイド、トリフェニルベンジルホスホニウムアイオダイド、トリフェニルメトキシメチルホスホニウムクロライド、トリエチルベンジルホスホニウムクロライド、トリシクロヘキシルベンジルホスホニウムクロライド、トリオクチルメチルホスホニウムジメチルホスフェート、テトラブチルホスホニウムブロマイド、トリオクチルメチルホスホニウムアセテートなどが挙げられる。
Examples of quaternary phosphonium salt compounds include triphenylbenzylphosphonium chloride, triphenylbenzylphosphonium bromide, triphenylbenzylphosphonium iodide, triphenylmethoxymethylphosphonium chloride, triethylbenzylphosphonium chloride, tricyclohexylbenzylphosphonium chloride, trioctyl methylphosphonium dimethyl phosphate, tetrabutylphosphonium bromide, trioctylmethylphosphonium acetate and the like.
ハロゲン基を有する不飽和単量体に由来する構成単位を用いた場合、(b)架橋剤としてはトリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、および硫黄からなる群より選択される少なくとも1種との組み合わせが好ましい。
When a structural unit derived from an unsaturated monomer having a halogen group is used, the (b) cross-linking agent is selected from the group consisting of a triazine thiol derivative compound, an organic carboxylate ammonium salt compound, a metal soap, and sulfur. A combination with at least one of
カルボキシル基を有する不飽和単量体に由来する構成単位を用いた場合、(b)架橋剤としては多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、およびアジリジン化合物からなる群より選択される少なくとも1種との組み合わせが好ましく、多価アミン化合物、多価エポキシ化合物、アジリジン化合物からなる群より選択される少なくとも1種との組み合わせがより好ましく、多価アミン化合物との組み合わせがさらに好ましい。
When a structural unit derived from an unsaturated monomer having a carboxyl group is used, the (b) cross-linking agent includes a polyamine compound, a polyhydrazide compound, a polyepoxy compound, a polyisocyanate compound, and an aziridine compound. A combination with at least one selected from the group consisting of is preferred, and a combination with at least one selected from the group consisting of a polyamine compound, a polyepoxy compound, and an aziridine compound is more preferred, and a polyamine compound and is more preferred.
エポキシ基を有する不飽和単量体に由来する構成単位を用いた場合、(b)架橋剤としては有機カルボン酸アンモニウム塩化合物、ジチオカルバミン酸塩化合物、多価アミン化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種との組み合わせが好ましい。
When a structural unit derived from an unsaturated monomer having an epoxy group is used, the (b) cross-linking agent includes an organic carboxylic acid ammonium salt compound, a dithiocarbamate compound, a polyvalent amine compound, an imidazole compound, and a polycarboxylic acid. A combination with at least one selected from the group consisting of compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds is preferred.
これらの(b)架橋剤は単独、または2種以上を組み合わせて使用することもできる。本発明の熱伝導用素材組成物において、(b)架橋剤の含有量は、本発明の(a)アクリル系エラストマー100質量部に対して0.05質量部~20質量部であることが好ましく、0.1質量部~10質量部であることがより好ましい。
These (b) cross-linking agents can be used alone or in combination of two or more. In the heat conductive material composition of the present invention, the content of (b) the cross-linking agent is preferably 0.05 to 20 parts by mass with respect to 100 parts by mass of the (a) acrylic elastomer of the present invention. , more preferably 0.1 to 10 parts by mass.
<(c)熱伝導フィラー>
本発明の(c)熱伝導フィラーは、大別して導電性熱伝導フィラー、絶縁性熱伝導フィラーの2種類あり、本発明においては、導電性熱伝導フィラーを用いることで電気回路の短絡を招く危険性を考慮し、絶縁性熱伝導フィラーを用いることが好ましい。 <(c) Thermal conductive filler>
The (c) thermally conductive filler of the present invention is roughly divided into two types: an electrically conductive thermally conductive filler and an insulating thermally conductive filler. In consideration of the properties, it is preferable to use an insulating thermally conductive filler.
本発明の(c)熱伝導フィラーは、大別して導電性熱伝導フィラー、絶縁性熱伝導フィラーの2種類あり、本発明においては、導電性熱伝導フィラーを用いることで電気回路の短絡を招く危険性を考慮し、絶縁性熱伝導フィラーを用いることが好ましい。 <(c) Thermal conductive filler>
The (c) thermally conductive filler of the present invention is roughly divided into two types: an electrically conductive thermally conductive filler and an insulating thermally conductive filler. In consideration of the properties, it is preferable to use an insulating thermally conductive filler.
絶縁性熱伝導フィラーとしては、例えば、水酸化アルミニウム、酸化アルミニウム(アルミナ)、酸化亜鉛、二酸化チタン、酸化ベリリウム、酸化マグネシウム、酸化ニッケル、酸化バナジウム、酸化銅、酸化鉄、酸化銀、石英粉、窒化ケイ素、炭化ケイ素、雲母、窒化ホウ素、窒化アルミニウムなどが挙げられる。これらのなかでも、水酸化アルミニウム、酸化アルミニウム(アルミナ)、窒化アルミニウム、窒化ホウ素、および炭化ケイ素からなる群より選択される少なくとも1種を使用することが好ましく、酸化アルミニウム(アルミナ)、窒化アルミニウム、および窒化ホウ素からなる群より選択される少なくとも1種を使用することがより好ましい。また、形状としては、鱗片状、球状、粒状、粉状、繊維状、針状、ウィスカー状から任意の形状のものが使用できる。これら熱伝導フィラーは、単独使用、もしくは2種以上を組み合わせて使用することができる。また、これらを主原料とした複合材料を使用することもできる。
Examples of insulating and thermally conductive fillers include aluminum hydroxide, aluminum oxide (alumina), zinc oxide, titanium dioxide, beryllium oxide, magnesium oxide, nickel oxide, vanadium oxide, copper oxide, iron oxide, silver oxide, quartz powder, Silicon nitride, silicon carbide, mica, boron nitride, aluminum nitride and the like. Among these, it is preferable to use at least one selected from the group consisting of aluminum hydroxide, aluminum oxide (alumina), aluminum nitride, boron nitride, and silicon carbide, and aluminum oxide (alumina), aluminum nitride, and boron nitride. Moreover, as for the shape, those having an arbitrary shape from scaly, spherical, granular, powdery, fibrous, needle-like, and whisker-like can be used. These thermally conductive fillers can be used singly or in combination of two or more. Composite materials containing these as main raw materials can also be used.
(c)熱伝導フィラーの粒子径としては、0.1~200μmであることが好ましく、0.5~150μmであることがより好ましく、0.5~100μmであることがさらに好ましく、2~40μmであることが特に好ましい。この範囲にあることで熱伝導フィラー同士の接触点が多くなり、期待される熱伝導率が得られやすい。
本明細書において、熱伝導フィラーの粒子径は、透過型電子顕微鏡(TEM)観察により測定できる。具体的には、熱伝導フィラーを透過型電子顕微鏡で写真撮影し、形状が球形の場合には球の直径を粒子径とし、針状または棒状の場合には短径を粒子径とし、不定型などその他の形状の場合には中心部からの平均粒子径を粒子径とし、粒子100個の粒子径の平均値を粒子径(平均粒子径)として測定される。 (c) The particle size of the thermally conductive filler is preferably 0.1 to 200 μm, more preferably 0.5 to 150 μm, even more preferably 0.5 to 100 μm, and 2 to 40 μm. is particularly preferred. Within this range, the number of contact points between the thermally conductive fillers increases, and the expected thermal conductivity can be easily obtained.
In this specification, the particle size of the thermally conductive filler can be measured by observation with a transmission electron microscope (TEM). Specifically, the thermally conductive filler is photographed with a transmission electron microscope. In the case of other shapes such as, the average particle diameter from the center is defined as the particle diameter, and the average value of the particle diameters of 100 particles is measured as the particle diameter (average particle diameter).
本明細書において、熱伝導フィラーの粒子径は、透過型電子顕微鏡(TEM)観察により測定できる。具体的には、熱伝導フィラーを透過型電子顕微鏡で写真撮影し、形状が球形の場合には球の直径を粒子径とし、針状または棒状の場合には短径を粒子径とし、不定型などその他の形状の場合には中心部からの平均粒子径を粒子径とし、粒子100個の粒子径の平均値を粒子径(平均粒子径)として測定される。 (c) The particle size of the thermally conductive filler is preferably 0.1 to 200 μm, more preferably 0.5 to 150 μm, even more preferably 0.5 to 100 μm, and 2 to 40 μm. is particularly preferred. Within this range, the number of contact points between the thermally conductive fillers increases, and the expected thermal conductivity can be easily obtained.
In this specification, the particle size of the thermally conductive filler can be measured by observation with a transmission electron microscope (TEM). Specifically, the thermally conductive filler is photographed with a transmission electron microscope. In the case of other shapes such as, the average particle diameter from the center is defined as the particle diameter, and the average value of the particle diameters of 100 particles is measured as the particle diameter (average particle diameter).
(c)熱伝導フィラーの熱伝導率としては、特に制限されることはないが、下限としては、20W/m・K以上であることが好ましく、30W/m・K以上であることがさらに好ましく、40W/m・K以上であることが好ましい。上限としては、1000W/m・K以下であることが好ましく、700W/m・K以下であることがより好ましく、500W/m・K以下であることがさらに好ましい。
本明細書において、熱伝導フィラーの熱伝導率は、レーザーフラッシュ法(JIS R1611)により測定される。 (c) The thermal conductivity of the thermally conductive filler is not particularly limited, but the lower limit is preferably 20 W/m·K or more, more preferably 30 W/m·K or more. , 40 W/m·K or more. The upper limit is preferably 1000 W/m·K or less, more preferably 700 W/m·K or less, and even more preferably 500 W/m·K or less.
In this specification, the thermal conductivity of the thermally conductive filler is measured by the laser flash method (JIS R1611).
本明細書において、熱伝導フィラーの熱伝導率は、レーザーフラッシュ法(JIS R1611)により測定される。 (c) The thermal conductivity of the thermally conductive filler is not particularly limited, but the lower limit is preferably 20 W/m·K or more, more preferably 30 W/m·K or more. , 40 W/m·K or more. The upper limit is preferably 1000 W/m·K or less, more preferably 700 W/m·K or less, and even more preferably 500 W/m·K or less.
In this specification, the thermal conductivity of the thermally conductive filler is measured by the laser flash method (JIS R1611).
本発明の熱伝導用素材組成物において、(c)熱伝導フィラー(好ましくは絶縁性熱伝導フィラー)の含有量は、(a)アクリル系エラストマー100質量部に対して、100質量部~900質量部であることが好ましく、150質量部~800質量部であることがより好ましく、200質量部~700質量部であることがさらに好ましい。この範囲未満であれば、期待される熱伝導率が得られず、また上限を超えると加工性が著しく劣る可能性がある。(c)熱伝導フィラーの含有量を上記数値範囲の下限値以上とすることにより、熱伝導用素材組成物の架橋後の熱伝導率を1.0W/(m・K)以上とすることが可能となる。
In the material composition for thermal conduction of the present invention, the content of (c) thermally conductive filler (preferably insulating thermally conductive filler) is 100 parts by mass to 900 parts by mass with respect to 100 parts by mass of (a) acrylic elastomer. parts, more preferably 150 to 800 parts by mass, even more preferably 200 to 700 parts by mass. If it is less than this range, the expected thermal conductivity cannot be obtained, and if it exceeds the upper limit, workability may be significantly deteriorated. (c) By setting the content of the thermally conductive filler to be equal to or higher than the lower limit of the above numerical range, the thermal conductivity of the thermally conductive material composition after cross-linking can be 1.0 W/(m·K) or higher. It becomes possible.
本発明の熱伝導用素材組成物において、導電性熱伝導フィラーの含有量は、(a)アクリル系エラストマー100質量部に対して、好ましくは20質量部以下、より好ましくは10質量部以下、さらに好ましくは5質量部以下、特に好ましくは1質量部以下、最も好ましくは0質量部である。これにより、電気回路の短絡を招く危険性をより低減できる傾向がある。
In the heat conductive material composition of the present invention, the content of the conductive heat conductive filler (a) is preferably 20 parts by mass or less, more preferably 10 parts by mass or less, with respect to 100 parts by mass of the acrylic elastomer. It is preferably 5 parts by mass or less, particularly preferably 1 part by mass or less, and most preferably 0 parts by mass. This tends to further reduce the risk of causing a short circuit in the electrical circuit.
また、本発明の熱伝導用素材組成物は、当該技術分野で通常使用される他の添加剤、例えば滑剤、老化防止剤、光安定化剤、充填剤、補強剤、可塑剤、加工助剤、顔料、着色剤、架橋促進剤、架橋助剤、架橋遅延剤、帯電防止剤、発泡剤等を任意に配合できる。これらは、単独、または2種以上を組み合わせて使用することもできる。
In addition, the heat-conducting material composition of the present invention may contain other additives commonly used in the art, such as lubricants, antioxidants, light stabilizers, fillers, reinforcing agents, plasticizers, and processing aids. , pigments, colorants, cross-linking accelerators, cross-linking auxiliaries, cross-linking retarders, antistatic agents, foaming agents and the like can be arbitrarily blended. These can also be used individually or in combination of 2 or more types.
補強剤としては、カーボンブラック等を例示することができ、その含有量は、(a)アクリル系エラストマー100質量部に対して、5質量部以上であることが好ましく、10質量部以上であることがより好ましく、15質量部以上であることがさらに好ましく、120質量部以下であることが好ましく、100質量部以下であることがより好ましい。
As the reinforcing agent, carbon black or the like can be exemplified, and the content thereof is preferably 5 parts by mass or more and 10 parts by mass or more with respect to 100 parts by mass of the (a) acrylic elastomer. is more preferably 15 parts by mass or more, preferably 120 parts by mass or less, and more preferably 100 parts by mass or less.
老化防止剤としては、例えば、アミン系、フォスフェート系、キノリン系、クレゾール系、フェノール系、ジチオカルバメート金属塩等が挙げられる。本発明においては、アミン系、フェノール系の老化防止剤を使用することが好ましい。これらは、単独、または2種以上を併用してもよい。
Anti-aging agents include, for example, amine-based, phosphate-based, quinoline-based, cresol-based, phenol-based, and dithiocarbamate metal salts. In the present invention, it is preferable to use an amine-based or phenol-based antioxidant. These may be used alone or in combination of two or more.
アミン系老化防止剤としては、例えば、フェニル-α-ナフチルアミン、フェニル-β-ナフチルアミン、p-(p-トルエンスルホニルアミド)-ジフェニルアミン、4,4'-ビス(α,α-ジメチルベンジル)ジフェニルアミン、N,N-ジフェニル-p-フェニレンジアミン、N-イソプロピル-N'-フェニル-p-フェニレンジアミン、ブチルアルデヒド-アニリン縮合物などが挙げられる。
Examples of amine antioxidants include phenyl-α-naphthylamine, phenyl-β-naphthylamine, p-(p-toluenesulfonylamido)-diphenylamine, 4,4′-bis(α,α-dimethylbenzyl)diphenylamine, N,N-diphenyl-p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, butyraldehyde-aniline condensate and the like.
フェノール系老化防止剤としては、例えば、2,6-ジ-t-ブチル-4-メチルフェノール、2,6-ジ-t-ブチルフェノール、ブチルヒドロキシアニソール、2,6-ジ-t-ブチル-α-ジメチルアミノ-p-クレゾール、オクタデシル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、スチレン化フェノール、2,2'-メチレン-ビス(6-α-メチルベンジル-p-クレゾール)、4,4'-メチレンビス(2,6-ジ-t-ブチルフェノール)、2,2'-メチレン-ビス(4-メチル-6-t-ブチルフェノール)、2,4-ビス[(オクチルチオ)メチル]-6-メチルフェノール、2,2'-チオビス-(4-メチル-6-t-ブチルフェノール)、4,4'-チオビス-(6-t-ブチル-o-クレゾール)、2,6-ジ-t-ブチル-4-(4,6-ビス(オクチルチオ)-1,3,5-トリアジン-2-イルアミノ)フェノールなどが挙げられる。
Phenolic antioxidants include, for example, 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butylphenol, butylhydroxyanisole, 2,6-di-t-butyl-α -dimethylamino-p-cresol, octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, styrenated phenol, 2,2′-methylene-bis(6-α-methylbenzyl- p-cresol), 4,4′-methylenebis(2,6-di-t-butylphenol), 2,2′-methylene-bis(4-methyl-6-t-butylphenol), 2,4-bis[( octylthio)methyl]-6-methylphenol, 2,2′-thiobis-(4-methyl-6-t-butylphenol), 4,4′-thiobis-(6-t-butyl-o-cresol), 2, 6-di-t-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol and the like.
老化防止剤の含有量は、(a)アクリル系エラストマー100質量部に対して、0.1~10質量部であることが好ましく、0.1~5質量部であることがより好ましく、0.3~3質量部であることが特に好ましい。
The content of the anti-aging agent is preferably 0.1 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, and 0.1 to 10 parts by mass, based on 100 parts by mass of the acrylic elastomer (a). 3 to 3 parts by mass is particularly preferred.
架橋促進剤としては、ジアザビシクロアルケン化合物、グアニジン化合物、アミン化合物、チオウレア化合物、チアゾール化合物、スルフェンアミド化合物、チウラム化合物、四級アンモニウム塩等が挙げられ、グアニジン化合物、アミン化合物が好ましい。これらは、単独、または2種以上を併用してもよい。
Examples of cross-linking accelerators include diazabicycloalkene compounds, guanidine compounds, amine compounds, thiourea compounds, thiazole compounds, sulfenamide compounds, thiuram compounds, and quaternary ammonium salts, with guanidine compounds and amine compounds being preferred. These may be used alone or in combination of two or more.
架橋促進剤の含有量は、(a)アクリル系エラストマー100質量部に対して、0.1~15質量部であることが好ましく、0.1~10質量部であることがより好ましく、0.1~5質量部であることが特に好ましい。
The content of the crosslinking accelerator is preferably 0.1 to 15 parts by mass, more preferably 0.1 to 10 parts by mass, more preferably 0.1 to 10 parts by mass, based on 100 parts by mass of the acrylic elastomer (a). 1 to 5 parts by mass is particularly preferred.
さらに、本発明の趣旨を逸脱しない範囲で、当該技術分野で通常使用されているゴム、樹脂等とのブレンドを行うことも可能である。本発明に用いることのできる通常使用されているゴムとしては、例えば、ブタジエンゴム、スチレン-ブタジエンゴム、イソプレンゴム、天然ゴム、アクリロニトリル-ブタジエンゴム、アクリロニトリル-ブタジエン-イソプレンゴム、エチレン-プロピレン-ジエンゴム、エピクロルヒドリンゴム等が挙げられ、また樹脂としては、例えば、PMMA(ポリメタクリル酸メチル)樹脂、PS(ポリスチレン)樹脂、PUR(ポリウレタン)樹脂、PVC(ポリ塩化ビニル)樹脂、EVA(エチレン/酢酸ビニル)樹脂、AS(スチレン/アクリロニトリル)樹脂、PE(ポリエチレン)樹脂等が挙げられる。これらは、単独、または2種以上を組み合わせて使用できる。
Furthermore, it is also possible to blend with rubbers, resins, etc. that are commonly used in the technical field within the scope of the present invention. Commonly used rubbers that can be used in the present invention include, for example, butadiene rubber, styrene-butadiene rubber, isoprene rubber, natural rubber, acrylonitrile-butadiene rubber, acrylonitrile-butadiene-isoprene rubber, ethylene-propylene-diene rubber, Examples include epichlorohydrin rubber and the like, and resins include, for example, PMMA (polymethyl methacrylate) resin, PS (polystyrene) resin, PUR (polyurethane) resin, PVC (polyvinyl chloride) resin, EVA (ethylene/vinyl acetate). resin, AS (styrene/acrylonitrile) resin, PE (polyethylene) resin, and the like. These can be used singly or in combination of two or more.
上記ゴム、樹脂の合計配合量は、本発明の(a)アクリル系エラストマー100質量部に対して、50質量部以下、好ましくは10質量部以下、より好ましくは1質量部以下である。
The total amount of the above rubber and resin compounded is 50 parts by mass or less, preferably 10 parts by mass or less, more preferably 1 part by mass or less per 100 parts by mass of the (a) acrylic elastomer of the present invention.
<熱伝導性素材(例えば、熱伝導性シート)>
本発明の熱伝導性素材は、本発明の熱伝導用素材組成物を架橋させることで得ることができる。熱伝導性素材の形状は特に限定されないが、加工のしやすさという理由から、シート状(すなわち、熱伝導性シート)であることが好ましい。 <Thermal conductive material (eg, thermally conductive sheet)>
The thermally conductive material of the present invention can be obtained by cross-linking the thermally conductive material composition of the present invention. Although the shape of the thermally conductive material is not particularly limited, it is preferably in the form of a sheet (that is, a thermally conductive sheet) for ease of processing.
本発明の熱伝導性素材は、本発明の熱伝導用素材組成物を架橋させることで得ることができる。熱伝導性素材の形状は特に限定されないが、加工のしやすさという理由から、シート状(すなわち、熱伝導性シート)であることが好ましい。 <Thermal conductive material (eg, thermally conductive sheet)>
The thermally conductive material of the present invention can be obtained by cross-linking the thermally conductive material composition of the present invention. Although the shape of the thermally conductive material is not particularly limited, it is preferably in the form of a sheet (that is, a thermally conductive sheet) for ease of processing.
本発明の熱伝導性素材(例えば、熱伝導性シート)を得るための熱伝導用素材組成物の配合方法としては、従来ゴム加工の分野において利用されている任意の手段、例えばオープンロール、バンバリーミキサー、各種ニーダー類等を利用することができる。その配合手順としては、ゴム加工の分野において行われている通常の手順で行うことができる。例えば、最初にゴムのみを混練りし、次いで架橋剤、架橋促進剤以外の配合剤を投入したA練りコンパウンドを作製し、その後、架橋剤、架橋促進剤を投入するB練りを行う手順で行うことができる。
As a method for compounding the thermally conductive material composition for obtaining the thermally conductive material (for example, a thermally conductive sheet) of the present invention, any means conventionally used in the field of rubber processing, such as open roll, Banbury, etc., can be used. A mixer, various kneaders, etc. can be used. As the compounding procedure, it can be carried out according to a usual procedure in the field of rubber processing. For example, first, only the rubber is kneaded, then A-kneaded compound is prepared by adding compounding agents other than the cross-linking agent and the cross-linking accelerator, and then B-kneading is performed by adding the cross-linking agent and the cross-linking accelerator. be able to.
本発明の熱伝導性素材(例えば、熱伝導性シート)は、上記熱伝導用素材組成物を、通常100℃~250℃に加熱、架橋させることで得ることができる。架橋時間は温度によって異なるが、0.5分~300分の間で行われるのが普通である。架橋成形は架橋と成形を一体的に行う場合や、先に成形した熱伝導用素材組成物を加熱することで熱伝導性素材(例えば、熱伝導性シート)とする場合のほか、先に加熱して熱伝導性素材(例えば、熱伝導性シート)とした後に成形加工を施す場合のいずれでもよい。架橋成形の具体的な方法としては、金型による圧縮成形、射出成形、スチーム缶、エアーバス、赤外線、あるいはマイクロウェーブによる加熱等任意の方法を用いることができる。
The thermally conductive material (for example, a thermally conductive sheet) of the present invention can be obtained by heating the above-mentioned thermally conductive material composition to usually 100°C to 250°C to crosslink it. The cross-linking time varies depending on the temperature, but is generally carried out between 0.5 minutes and 300 minutes. In cross-linking molding, in addition to the case where crosslinking and molding are performed integrally, or the case in which a thermally conductive material (for example, a thermally conductive sheet) is formed by heating a previously molded thermally conductive material composition, It may be formed into a thermally conductive material (for example, a thermally conductive sheet) and then subjected to a molding process. Specific methods for cross-linking molding include compression molding using a mold, injection molding, steam can, air bath, heating with infrared rays, or microwaves.
本発明の熱伝導用素材組成物を熱伝導性素材(例えば、熱伝導性シート)にした際、すなわち、本発明の熱伝導用素材組成物の架橋後の熱伝導率としては、1.0W/(m・K)以上であることが好ましく、1.1W/(m・K)以上であることがより好ましく、1.2W/(m・K)以上であることがさらに好ましく、大きければ大きいほど好ましいが、通常は20W/(m・K)以下である。熱伝導率が1.0W/(m・K)以上であれば、熱伝導材料として好適に使用できる。
本明細書において、熱伝導用素材組成物の架橋後の熱伝導率は、実施例の方法により測定される。 When the thermally conductive material composition of the present invention is made into a thermally conductive material (for example, a thermally conductive sheet), that is, the thermal conductivity of the thermally conductive material composition of the present invention after crosslinking is 1.0 W /(m K) or more, more preferably 1.1 W/(m K) or more, even more preferably 1.2 W/(m K) or more, the larger the larger It is preferably 20 W/(m·K) or less. A material having a thermal conductivity of 1.0 W/(m·K) or more can be suitably used as a thermally conductive material.
In this specification, the thermal conductivity of the thermally conductive material composition after cross-linking is measured by the method of Examples.
本明細書において、熱伝導用素材組成物の架橋後の熱伝導率は、実施例の方法により測定される。 When the thermally conductive material composition of the present invention is made into a thermally conductive material (for example, a thermally conductive sheet), that is, the thermal conductivity of the thermally conductive material composition of the present invention after crosslinking is 1.0 W /(m K) or more, more preferably 1.1 W/(m K) or more, even more preferably 1.2 W/(m K) or more, the larger the larger It is preferably 20 W/(m·K) or less. A material having a thermal conductivity of 1.0 W/(m·K) or more can be suitably used as a thermally conductive material.
In this specification, the thermal conductivity of the thermally conductive material composition after cross-linking is measured by the method of Examples.
本発明の熱伝送用素材組成物を熱伝導性素材(例えば、熱伝導性シート)にした際、すなわち、本発明の熱伝導用素材組成物の架橋後の硬度(JIS-A)としては、特に制限されるものではないが、80以下であることが好ましい。
本明細書において、上記硬度は、タイプAデュロメータによる硬度試験(JIS K6253-3)により測定される。 When the heat transfer material composition of the present invention is made into a heat conductive material (for example, a heat conductive sheet), that is, the hardness (JIS-A) after crosslinking of the heat transfer material composition of the present invention is as follows. Although not particularly limited, it is preferably 80 or less.
As used herein, the hardness is measured by a type A durometer hardness test (JIS K6253-3).
本明細書において、上記硬度は、タイプAデュロメータによる硬度試験(JIS K6253-3)により測定される。 When the heat transfer material composition of the present invention is made into a heat conductive material (for example, a heat conductive sheet), that is, the hardness (JIS-A) after crosslinking of the heat transfer material composition of the present invention is as follows. Although not particularly limited, it is preferably 80 or less.
As used herein, the hardness is measured by a type A durometer hardness test (JIS K6253-3).
このようにして本発明の熱伝導用素材組成物から得られる熱伝導性素材(例えば、熱伝導性シート)は、高い熱伝導率を備えており、電子機器等の熱伝導性素材(例えば、熱伝導性シート)としての使用に好適である。
A thermally conductive material (for example, a thermally conductive sheet) obtained from the thermally conductive material composition of the present invention in this way has a high thermal conductivity, and is a thermally conductive material for electronic devices (for example, It is suitable for use as a heat conductive sheet).
本発明を実施例、比較例をもって説明する。なお、本発明はこれらに限定されるものではない。本実施例および比較例では、熱伝導用素材組成物から作製する熱伝導性シートの物性を評価した。
The present invention will be explained with examples and comparative examples. In addition, this invention is not limited to these. In the present examples and comparative examples, physical properties of thermally conductive sheets produced from thermally conductive material compositions were evaluated.
評価項目については以下のとおりである。
<加工性>
加工性について、材料の混練工程において、フィラーが均一に分散し、シート化できたものを「○」、フィラーが均一に分散できず、シート化できなかったものを「×」として評価を行った。
<熱伝導率>
熱伝導率は熱線法(JIS R2251-2)にて行った。詳しくは、室温下においてセンサを予め熱伝導率が分かっている試料(標準サンプル)と熱伝導率を測定する試料とで熱線と熱電対とを挟み込み、5分間、熱線に定電流を流し一定発熱させて熱線の温度上昇を熱電対で計測し、標準サンプルの熱伝導率との偏差をプロットし、偏差0との交点から熱伝導率を算出した。この手法によって3回測定を行い、その平均値を算出した。 Evaluation items are as follows.
<Workability>
Regarding workability, in the kneading process of the material, the filler was uniformly dispersed and the sheet could be formed as "○", and the filler could not be uniformly dispersed and the sheet could not be formed as "x". Evaluation was performed. .
<Thermal conductivity>
Thermal conductivity was measured by the hot wire method (JIS R2251-2). Specifically, at room temperature, a hot wire and a thermocouple are sandwiched between a sample whose thermal conductivity is known in advance (standard sample) and a sample whose thermal conductivity is to be measured. The temperature rise of the hot wire was measured with a thermocouple, the deviation from the thermal conductivity of the standard sample was plotted, and the thermal conductivity was calculated from the intersection with the deviation of 0. Measurement was performed three times by this method, and the average value was calculated.
<加工性>
加工性について、材料の混練工程において、フィラーが均一に分散し、シート化できたものを「○」、フィラーが均一に分散できず、シート化できなかったものを「×」として評価を行った。
<熱伝導率>
熱伝導率は熱線法(JIS R2251-2)にて行った。詳しくは、室温下においてセンサを予め熱伝導率が分かっている試料(標準サンプル)と熱伝導率を測定する試料とで熱線と熱電対とを挟み込み、5分間、熱線に定電流を流し一定発熱させて熱線の温度上昇を熱電対で計測し、標準サンプルの熱伝導率との偏差をプロットし、偏差0との交点から熱伝導率を算出した。この手法によって3回測定を行い、その平均値を算出した。 Evaluation items are as follows.
<Workability>
Regarding workability, in the kneading process of the material, the filler was uniformly dispersed and the sheet could be formed as "○", and the filler could not be uniformly dispersed and the sheet could not be formed as "x". Evaluation was performed. .
<Thermal conductivity>
Thermal conductivity was measured by the hot wire method (JIS R2251-2). Specifically, at room temperature, a hot wire and a thermocouple are sandwiched between a sample whose thermal conductivity is known in advance (standard sample) and a sample whose thermal conductivity is to be measured. The temperature rise of the hot wire was measured with a thermocouple, the deviation from the thermal conductivity of the standard sample was plotted, and the thermal conductivity was calculated from the intersection with the deviation of 0. Measurement was performed three times by this method, and the average value was calculated.
[実施例1]
アクリル系エラストマー(商品名:ラクレスターCH、架橋基:カルボキシル基、大阪ソーダ社製)を100質量部、窒化アルミニウム1(商品名:トーヤルナイトTFZ-S20P、粒子径20μm、球状、東洋アルミ社製)を400質量部、ポリエーテルエステル系化合物(商品名:アデカサイザーRS-735、ADEKA社製)を20質量部、4,4’-ビス(α,α-ジメチルベンジル)ジフェニルアミン(商品名:ノクラックCD、大内新興化学工業社製)を2質量部、ステアリン酸を2質量部、パラフィンワックスを2質量部加えて、ラボプラストミル混練機(東洋精機社製)にて温度100℃、回転数30rpmの条件でA練りを行い、A練りコンパウンドを得た。その後、A練りコンパウンドにヘキサメチレンジアミンカルバメート(商品名:HA-36MC、大阪ソーダ社製)を0.6質量部、架橋促進剤(商品名:VULCOFAC ACT-55、Salfic Alcan社製)を1質量部添加し、オープンロールにて室温条件下でB練りを行い、B練りコンパウンド(熱伝導用素材組成物)を得た。次いで、得られた熱伝導用素材組成物をニーダーおよびオープンロールで混練し、厚さ2mmの未架橋の熱伝導性シートを作製し、180℃で5分プレス処理し、熱伝導性シートを得た。上記の評価項目に従って評価を行い、その結果を表1に示す。 [Example 1]
100 parts by mass of acrylic elastomer (trade name: Lacresta CH, crosslinking group: carboxyl group, manufactured by Osaka Soda Co., Ltd.), aluminum nitride 1 (trade name: Toyal Night TFZ-S20P, particle size 20 μm, spherical, manufactured by Toyo Aluminum Co., Ltd. ) of 400 parts by mass, 20 parts by mass of a polyether ester compound (trade name: ADEKA CIZER RS-735, manufactured by ADEKA), 4,4′-bis(α,α-dimethylbenzyl)diphenylamine (trade name: Nocrack 2 parts by mass of CD, manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.), 2 parts by mass of stearic acid, and 2 parts by mass of paraffin wax are added, and the temperature is 100 ° C. and the number of revolutions is 100 ° C. with a Laboplastomill kneader (manufactured by Toyo Seiki Co., Ltd.). A kneading was performed at 30 rpm to obtain an A kneading compound. After that, 0.6 parts by mass of hexamethylenediamine carbamate (trade name: HA-36MC, manufactured by Osaka Soda Co., Ltd.) and 1 mass of a cross-linking accelerator (trade name: VULCOFAC ACT-55, manufactured by Salfic Alcan) were added to the A kneading compound. and B-kneading was performed on an open roll at room temperature to obtain a B-kneading compound (heat-conducting material composition). Next, the obtained thermal conductive material composition was kneaded with a kneader and an open roll to prepare an uncrosslinked thermal conductive sheet with a thickness of 2 mm, and pressed at 180° C. for 5 minutes to obtain a thermal conductive sheet. rice field. Evaluation was performed according to the above evaluation items, and the results are shown in Table 1.
アクリル系エラストマー(商品名:ラクレスターCH、架橋基:カルボキシル基、大阪ソーダ社製)を100質量部、窒化アルミニウム1(商品名:トーヤルナイトTFZ-S20P、粒子径20μm、球状、東洋アルミ社製)を400質量部、ポリエーテルエステル系化合物(商品名:アデカサイザーRS-735、ADEKA社製)を20質量部、4,4’-ビス(α,α-ジメチルベンジル)ジフェニルアミン(商品名:ノクラックCD、大内新興化学工業社製)を2質量部、ステアリン酸を2質量部、パラフィンワックスを2質量部加えて、ラボプラストミル混練機(東洋精機社製)にて温度100℃、回転数30rpmの条件でA練りを行い、A練りコンパウンドを得た。その後、A練りコンパウンドにヘキサメチレンジアミンカルバメート(商品名:HA-36MC、大阪ソーダ社製)を0.6質量部、架橋促進剤(商品名:VULCOFAC ACT-55、Salfic Alcan社製)を1質量部添加し、オープンロールにて室温条件下でB練りを行い、B練りコンパウンド(熱伝導用素材組成物)を得た。次いで、得られた熱伝導用素材組成物をニーダーおよびオープンロールで混練し、厚さ2mmの未架橋の熱伝導性シートを作製し、180℃で5分プレス処理し、熱伝導性シートを得た。上記の評価項目に従って評価を行い、その結果を表1に示す。 [Example 1]
100 parts by mass of acrylic elastomer (trade name: Lacresta CH, crosslinking group: carboxyl group, manufactured by Osaka Soda Co., Ltd.), aluminum nitride 1 (trade name: Toyal Night TFZ-S20P, particle size 20 μm, spherical, manufactured by Toyo Aluminum Co., Ltd. ) of 400 parts by mass, 20 parts by mass of a polyether ester compound (trade name: ADEKA CIZER RS-735, manufactured by ADEKA), 4,4′-bis(α,α-dimethylbenzyl)diphenylamine (trade name: Nocrack 2 parts by mass of CD, manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.), 2 parts by mass of stearic acid, and 2 parts by mass of paraffin wax are added, and the temperature is 100 ° C. and the number of revolutions is 100 ° C. with a Laboplastomill kneader (manufactured by Toyo Seiki Co., Ltd.). A kneading was performed at 30 rpm to obtain an A kneading compound. After that, 0.6 parts by mass of hexamethylenediamine carbamate (trade name: HA-36MC, manufactured by Osaka Soda Co., Ltd.) and 1 mass of a cross-linking accelerator (trade name: VULCOFAC ACT-55, manufactured by Salfic Alcan) were added to the A kneading compound. and B-kneading was performed on an open roll at room temperature to obtain a B-kneading compound (heat-conducting material composition). Next, the obtained thermal conductive material composition was kneaded with a kneader and an open roll to prepare an uncrosslinked thermal conductive sheet with a thickness of 2 mm, and pressed at 180° C. for 5 minutes to obtain a thermal conductive sheet. rice field. Evaluation was performed according to the above evaluation items, and the results are shown in Table 1.
[実施例2]
実施例1の窒化アルミニウム1 400質量部のうち200質量部を粒子径の異なる窒化アルミニウム2(商品名:トーヤルナイトTFZ-S05P、粒子径5μm、球状、東洋アルミ社製)に変更し、合計400質量部とした以外は実施例1と同様に熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 2]
Of the 400 parts by mass of aluminum nitride 1 in Example 1, 200 parts by mass was changed to aluminum nitride 2 with a different particle size (trade name: Toyalnite TFZ-S05P, particle size 5 μm, spherical, manufactured by Toyo Aluminum Co., Ltd.), totaling 400 parts by mass. A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that parts by mass were used. Evaluation was performed as described above, and the results are shown in Table 1.
実施例1の窒化アルミニウム1 400質量部のうち200質量部を粒子径の異なる窒化アルミニウム2(商品名:トーヤルナイトTFZ-S05P、粒子径5μm、球状、東洋アルミ社製)に変更し、合計400質量部とした以外は実施例1と同様に熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 2]
Of the 400 parts by mass of aluminum nitride 1 in Example 1, 200 parts by mass was changed to aluminum nitride 2 with a different particle size (trade name: Toyalnite TFZ-S05P, particle size 5 μm, spherical, manufactured by Toyo Aluminum Co., Ltd.), totaling 400 parts by mass. A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that parts by mass were used. Evaluation was performed as described above, and the results are shown in Table 1.
[実施例3]
実施例1の窒化アルミニウム1 400質量部をアルミナ系熱伝導フィラー(商品名:ダイピロキサイド7330、アルミナと他種金属酸化物との複合材料、粒子径10μm、球状、大日精化社製)300質量部に変更した以外は実施例1と同様に熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 3]
300 parts by mass of aluminum nitride 1 of Example 1 and 300 parts by mass of alumina-based thermal conductive filler (trade name: Dipyroxide 7330, composite material of alumina and other metal oxides, particle size 10 μm, spherical, manufactured by Dainichiseika Co., Ltd.) A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that the parts were changed to parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
実施例1の窒化アルミニウム1 400質量部をアルミナ系熱伝導フィラー(商品名:ダイピロキサイド7330、アルミナと他種金属酸化物との複合材料、粒子径10μm、球状、大日精化社製)300質量部に変更した以外は実施例1と同様に熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 3]
300 parts by mass of aluminum nitride 1 of Example 1 and 300 parts by mass of alumina-based thermal conductive filler (trade name: Dipyroxide 7330, composite material of alumina and other metal oxides, particle size 10 μm, spherical, manufactured by Dainichiseika Co., Ltd.) A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that the parts were changed to parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
[実施例4]
実施例3のアルミナ系熱伝導フィラー300質量部を400質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 4]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 3, except that 300 parts by mass of the alumina-based thermally conductive filler in Example 3 was changed to 400 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
実施例3のアルミナ系熱伝導フィラー300質量部を400質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 4]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 3, except that 300 parts by mass of the alumina-based thermally conductive filler in Example 3 was changed to 400 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
[実施例5]
実施例3のアルミナ系熱伝導フィラー300質量部を六方晶窒化ホウ素(商品名:ショウビーエヌUHP-1K、粒子径8μm、鱗片状、昭和電工社製)300質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 5]
Example except that 300 parts by mass of the alumina-based thermally conductive filler in Example 3 was changed to 300 parts by mass of hexagonal boron nitride (trade name: SHOBN UHP-1K, particle size 8 μm, scale shape, manufactured by Showa Denko) A heat conductive material composition and a heat conductive sheet were prepared in the same manner as in 3. Evaluation was performed as described above, and the results are shown in Table 1.
実施例3のアルミナ系熱伝導フィラー300質量部を六方晶窒化ホウ素(商品名:ショウビーエヌUHP-1K、粒子径8μm、鱗片状、昭和電工社製)300質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 5]
Example except that 300 parts by mass of the alumina-based thermally conductive filler in Example 3 was changed to 300 parts by mass of hexagonal boron nitride (trade name: SHOBN UHP-1K, particle size 8 μm, scale shape, manufactured by Showa Denko) A heat conductive material composition and a heat conductive sheet were prepared in the same manner as in 3. Evaluation was performed as described above, and the results are shown in Table 1.
[実施例6]
実施例5の六方晶窒化ホウ素300質量部を400質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 6]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 3, except that 300 parts by mass of hexagonal boron nitride in Example 5 was changed to 400 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
実施例5の六方晶窒化ホウ素300質量部を400質量部に変更した以外は実施例3と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Example 6]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 3, except that 300 parts by mass of hexagonal boron nitride in Example 5 was changed to 400 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
[比較例1]
実施例1の窒化アルミニウム1 400質量部を酸化アルミニウム(商品名:アルミナビーズCB-A50BC、粒子径50μm、球状、昭和電工社製)50質量部に変更した以外は実施例1と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Comparative Example 1]
Heating was performed in the same manner as in Example 1 except that 400 parts by mass of aluminum nitride 1 in Example 1 was changed to 50 parts by mass of aluminum oxide (trade name: alumina beads CB-A50BC, particle size 50 μm, spherical, manufactured by Showa Denko). A material composition for conduction and a thermally conductive sheet were produced. Evaluation was performed as described above, and the results are shown in Table 1.
実施例1の窒化アルミニウム1 400質量部を酸化アルミニウム(商品名:アルミナビーズCB-A50BC、粒子径50μm、球状、昭和電工社製)50質量部に変更した以外は実施例1と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Comparative Example 1]
Heating was performed in the same manner as in Example 1 except that 400 parts by mass of aluminum nitride 1 in Example 1 was changed to 50 parts by mass of aluminum oxide (trade name: alumina beads CB-A50BC, particle size 50 μm, spherical, manufactured by Showa Denko). A material composition for conduction and a thermally conductive sheet were produced. Evaluation was performed as described above, and the results are shown in Table 1.
[比較例2]
実施例5の窒化ホウ素300質量部を1000質量部に変更した以外は実施例1と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Comparative Example 2]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that 300 parts by mass of boron nitride in Example 5 was changed to 1000 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
実施例5の窒化ホウ素300質量部を1000質量部に変更した以外は実施例1と同様にして熱伝導用素材組成物、熱伝導性シートを作製した。上記の通りの評価を行い、その結果を表1に示す。 [Comparative Example 2]
A thermally conductive material composition and a thermally conductive sheet were produced in the same manner as in Example 1, except that 300 parts by mass of boron nitride in Example 5 was changed to 1000 parts by mass. Evaluation was performed as described above, and the results are shown in Table 1.
実施例1~6の本発明の熱伝導用素材組成物は、加工性もよく、これより作製される熱伝導性シートは高い熱伝導率を有していることが分かる。一方、比較例1のように熱伝導フィラーが少ないと加工性に問題はないが、熱伝導率が1.0W/(m・K)未満となってしまい、熱伝導性シートとしては使えないことが分かった。また、逆に比較例2のように熱伝導フィラーが多すぎると混練時にまとまらず、シート作製ができなかった。
It can be seen that the thermally conductive material compositions of Examples 1 to 6 of the present invention have good workability, and the thermally conductive sheets produced therefrom have high thermal conductivity. On the other hand, if the thermally conductive filler is small as in Comparative Example 1, there is no problem with workability, but the thermal conductivity is less than 1.0 W / (m K), and it cannot be used as a thermally conductive sheet. I found out. On the other hand, when the amount of the thermally conductive filler was too large, as in Comparative Example 2, the mixture did not come together during kneading, making it impossible to produce a sheet.
本発明の熱伝導用素材組成物は加工性に優れており、またこれより作製される熱伝導性素材(例えば、熱伝導性シート)は熱伝導率に優れているため、小型化、薄膜化が進む電子機器類における熱伝導性素材(例えば、熱伝導性シート)として好適であり、産業上の利用可能性が高い。
The thermally conductive material composition of the present invention has excellent workability, and the thermally conductive material (for example, thermally conductive sheet) produced from it has excellent thermal conductivity, so that it can be made smaller and thinner. It is suitable as a thermally conductive material (for example, a thermally conductive sheet) in electronic devices, and has high industrial applicability.
The thermally conductive material composition of the present invention has excellent workability, and the thermally conductive material (for example, thermally conductive sheet) produced from it has excellent thermal conductivity, so that it can be made smaller and thinner. It is suitable as a thermally conductive material (for example, a thermally conductive sheet) in electronic devices, and has high industrial applicability.
Claims (6)
- (a)アクリル系エラストマー、(b)架橋剤、(c)熱伝導フィラーを少なくとも含む熱伝導用素材組成物であって、前記熱伝導用素材組成物の架橋後の熱伝導率が1.0W/(m・K)以上である熱伝導用素材組成物。 A thermally conductive material composition containing at least (a) an acrylic elastomer, (b) a cross-linking agent, and (c) a thermally conductive filler, wherein the thermally conductive material composition has a thermal conductivity of 1.0 W after cross-linking. / (m·K) or more of the material composition for heat conduction.
- (a)アクリル系エラストマーは、ハロゲン基を有する不飽和単量体に由来する構成単位、カルボキシル基を有する不飽和単量体に由来する構成単位、およびエポキシ基を有する不飽和単量体に由来する構成単位からなる群より選択される少なくとも1種の構成単位を含有する請求項1記載の熱伝導用素材組成物。 (a) The acrylic elastomer is derived from a structural unit derived from an unsaturated monomer having a halogen group, a structural unit derived from an unsaturated monomer having a carboxyl group, and an unsaturated monomer having an epoxy group. 2. The heat-conducting material composition according to claim 1, comprising at least one structural unit selected from the group consisting of
- (b)架橋剤が、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、アジリジン化合物、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、硫黄、ジチオカルバミン酸塩化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種である請求項2記載の熱伝導用素材組成物。 (b) The cross-linking agent is a polyamine compound, polyhydrazide compound, polyepoxy compound, polyisocyanate compound, aziridine compound, triazinethiol derivative compound, organic carboxylate ammonium salt compound, metal soap, sulfur, dithiocarbamine 3. The heat-conducting material composition according to claim 2, wherein the compound is at least one selected from the group consisting of an acid salt compound, an imidazole compound, a polycarboxylic acid compound, a quaternary ammonium salt compound, and a quaternary phosphonium salt compound. .
- 架橋基を有する不飽和単量体と架橋剤の組合せが、
架橋基がハロゲン基の場合、トリアジンチオール誘導体化合物、有機カルボン酸アンモニウム塩化合物、金属石ケン、および硫黄からなる群より選択される少なくとも1種との組み合わせ、
架橋基がカルボキシル基の場合、多価アミン化合物、多価ヒドラジド化合物、多価エポキシ化合物、多価イソシアナート化合物、およびアジリジン化合物からなる群より選択される少なくとも1種との組み合わせ、または
架橋基がエポキシ基の場合、有機カルボン酸アンモニウム塩化合物、ジチオカルバミン酸塩化合物、多価アミン化合物、イミダゾール類化合物、ポリカルボン酸化合物、第4級アンモニウム塩化合物、および第4級ホスホニウム塩化合物からなる群より選択される少なくとも1種との組み合わせである請求項3記載の熱伝導用素材組成物。 A combination of an unsaturated monomer having a cross-linking group and a cross-linking agent is
When the cross-linking group is a halogen group, combination with at least one selected from the group consisting of a triazine thiol derivative compound, an organic carboxylate ammonium salt compound, a metal soap, and sulfur;
When the cross-linking group is a carboxyl group, it is combined with at least one selected from the group consisting of polyamine compounds, polyhydrazide compounds, polyepoxy compounds, polyisocyanate compounds, and aziridine compounds, or the cross-linking group is In the case of an epoxy group, it is selected from the group consisting of organic carboxylic acid ammonium salt compounds, dithiocarbamate compounds, polyvalent amine compounds, imidazole compounds, polycarboxylic acid compounds, quaternary ammonium salt compounds, and quaternary phosphonium salt compounds. 4. The material composition for heat conduction according to claim 3, which is a combination with at least one of - (c)熱伝導フィラーが、水酸化アルミニウム、酸化アルミニウム(アルミナ)、窒化アルミニウム、窒化ホウ素、および炭化ケイ素からなる群より選択される少なくとも1種である請求項1記載の熱伝導用素材組成物。 (c) The thermally conductive material composition according to claim 1, wherein the thermally conductive filler is at least one selected from the group consisting of aluminum hydroxide, aluminum oxide (alumina), aluminum nitride, boron nitride, and silicon carbide. .
- 請求項1~5のいずれかに記載の熱伝導用素材組成物を架橋させてなる熱伝導性素材。
A thermally conductive material obtained by cross-linking the thermally conductive material composition according to any one of claims 1 to 5.
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JP2007184392A (en) * | 2006-01-06 | 2007-07-19 | Taika:Kk | Thermoconductive structural body, and heat dissipating memeber and electronic device using the same |
JP2008120928A (en) * | 2006-11-13 | 2008-05-29 | Kitagawa Ind Co Ltd | Damping material and damping device |
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