JP2015105375A - Resin composition, thermally conductive cured product, silicon compound, silane coupling agent composition and carrier - Google Patents
Resin composition, thermally conductive cured product, silicon compound, silane coupling agent composition and carrier Download PDFInfo
- Publication number
- JP2015105375A JP2015105375A JP2013249861A JP2013249861A JP2015105375A JP 2015105375 A JP2015105375 A JP 2015105375A JP 2013249861 A JP2013249861 A JP 2013249861A JP 2013249861 A JP2013249861 A JP 2013249861A JP 2015105375 A JP2015105375 A JP 2015105375A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- coupling agent
- silane coupling
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- -1 ethylmethylamino Chemical group 0.000 claims description 46
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 8
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 20
- 239000000047 product Substances 0.000 description 46
- 229920005989 resin Polymers 0.000 description 44
- 239000011347 resin Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 36
- 238000000034 method Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000000945 filler Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 12
- 229920000647 polyepoxide Polymers 0.000 description 12
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 239000011231 conductive filler Substances 0.000 description 10
- 238000001179 sorption measurement Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 0 *c1ccc(*=*c2ccc(*)cc2)cc1 Chemical compound *c1ccc(*=*c2ccc(*)cc2)cc1 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 239000011888 foil Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000005011 phenolic resin Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
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- 239000000538 analytical sample Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- 229930195733 hydrocarbon Natural products 0.000 description 4
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 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 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 3
- 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
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 150000002460 imidazoles Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
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- 239000003086 colorant Substances 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
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- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
本発明は、樹脂組成物、該樹脂組成物を硬化させて得られる熱伝導性硬化物、特定の構造を有する新規なケイ素化合物、該ケイ素化合物を含有するシランカップリング剤組成物、及び該シランカップリング剤組成物を担持した担持体に関する。 The present invention relates to a resin composition, a thermally conductive cured product obtained by curing the resin composition, a novel silicon compound having a specific structure, a silane coupling agent composition containing the silicon compound, and the silane The present invention relates to a carrier carrying a coupling agent composition.
近年、電気機器や電子機器の高速化及び高機能化に伴い、半導体素子やパワートランジスタ等の電子部品は高集積化且つ高密度化される傾向にある。しかし、電子部品を高集積化及び高密度化すると、消費電力が増大して発熱量が増加してしまうという問題点がある。電子部品内部で発生した熱は、電子部品の劣化や誤作動等の不具合を引き起こす場合がある。 2. Description of the Related Art In recent years, electronic components such as semiconductor elements and power transistors tend to be highly integrated and highly densified as electrical devices and electronic devices become faster and more functional. However, when electronic components are highly integrated and densified, there is a problem that power consumption increases and the amount of heat generation increases. The heat generated inside the electronic component may cause problems such as deterioration and malfunction of the electronic component.
このような不具合を抑制する方法として、様々な報告がなされている。例えば、電子部品から熱を取り除く方法として、冷却ファンに代表される冷却用部品を用いて強制的に空冷する方法が知られている。また、シリコーングリースを塗布して放熱する方法や、熱伝導性シートを用いて熱を電子部品から冷却用部品に伝達させる方法が知られている。 Various reports have been made as methods for suppressing such problems. For example, as a method of removing heat from an electronic component, a method of forcibly cooling air using a cooling component typified by a cooling fan is known. In addition, there are known a method of dissipating heat by applying silicone grease and a method of transferring heat from an electronic component to a cooling component using a heat conductive sheet.
電子部品から冷却用部品に効率よく熱を伝達させる方法に用いられる熱伝導性シートとしては、様々なものが報告されている。例えば、特許文献1には、エポキシ樹脂、硬化剤、フィラー、表面処理剤、及び溶媒を含有する樹脂組成物を用いて形成した熱伝導性エポキシ樹脂シート材が開示されている。また、特許文献2には、シリコーン系共重合体と熱伝導性フィラーを含有する熱伝導シート、並びに熱伝導性フィラーとして窒化アルミニウム、酸化アルミニウム、及び窒化ホウ素が好ましいことが開示されている。さらに、特許文献2には、シランカップリング剤を含有させると、熱伝導性フィラーの分散性や、シリコーン系共重合体と熱伝導性フィラーの密着性が向上することが開示されている。 Various thermal conductive sheets have been reported as methods for efficiently transferring heat from electronic components to cooling components. For example, Patent Document 1 discloses a thermally conductive epoxy resin sheet material formed using a resin composition containing an epoxy resin, a curing agent, a filler, a surface treatment agent, and a solvent. Patent Document 2 discloses that a heat conductive sheet containing a silicone copolymer and a heat conductive filler, and that aluminum nitride, aluminum oxide, and boron nitride are preferable as the heat conductive filler. Furthermore, Patent Document 2 discloses that when a silane coupling agent is contained, the dispersibility of the heat conductive filler and the adhesion between the silicone copolymer and the heat conductive filler are improved.
電子部品から冷却用部品に効率よく熱を伝達させるための熱伝導性シートとして、シート状の熱伝導性硬化物を用いる場合、この熱伝導性硬化物は高い熱伝導性を有するものであることが求められる。従来、熱伝導性硬化物の熱伝導性を向上させるために、フィラーの種類やその含有量について検討されてきたが、所望の熱伝導性を有する熱伝導性硬化物を得ることはできなかった。このため、熱伝導性硬化物の熱伝導性を効果的に向上させうる添加剤等を開発することが望まれていた。 When a sheet-like thermally conductive cured product is used as a thermally conductive sheet for efficiently transferring heat from an electronic component to a cooling component, the thermally conductive cured product must have high thermal conductivity. Is required. Conventionally, in order to improve the thermal conductivity of the thermally conductive cured product, the type of filler and its content have been studied, but a thermally conductive cured product having a desired thermal conductivity could not be obtained. . For this reason, it has been desired to develop an additive or the like that can effectively improve the thermal conductivity of the thermally conductive cured product.
本発明者等は、検討を重ねた結果、特定の構造を有するケイ素化合物を含有するシランカップリング剤組成物を担持した担持体を含有する樹脂組成物を硬化させて得られる硬化物が、特に優れた熱伝導性を示すことを知見し、本発明を完成するに至った。 As a result of repeated studies, the present inventors have found that a cured product obtained by curing a resin composition containing a carrier carrying a silane coupling agent composition containing a silicon compound having a specific structure, The inventors have found that it exhibits excellent thermal conductivity, and have completed the present invention.
すなわち、本発明は、シランカップリング剤組成物を担持した担持体を含有し、前記シランカップリング剤組成物が、下記一般式(1)で表されるケイ素化合物を含有する樹脂組成物を提供する。さらに、本発明は、この樹脂組成物を硬化させて得られる熱伝導性硬化物を提供する。 That is, the present invention provides a resin composition containing a carrier carrying a silane coupling agent composition, wherein the silane coupling agent composition contains a silicon compound represented by the following general formula (1). To do. Furthermore, this invention provides the heat conductive hardened | cured material obtained by hardening this resin composition.
(前記一般式(1)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A1は単結合又は炭素原子数1〜4のアルカンジイル基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す。Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Xが下記式(X−1)で表される基である場合のZは−NHCO−であり、Xが下記式(X−2)〜(X−6)のいずれかで表される基である場合のZは単結合又は−NHCO−である) (In the general formula (1), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, and A 1 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched oxyalkyl group having 1 to 12 carbon atoms, a dimethylamino group, a diethylamino group, or ethyl Represents a methylamino group, X represents a group represented by any one of the following formulas (X-1) to (X-6), and X represents a group represented by the following formula (X-1). Z is -NHCO-, and Z is a single bond or -NHCO- when X is a group represented by any one of the following formulas (X-2) to (X-6))
また、本発明は、下記一般式(2)で表されるケイ素化合物、このケイ素化合物を含有するシランカップリング剤組成物、及びこのシランカップリング剤組成物を担持した担持体を提供する。 Moreover, this invention provides the silicon compound represented by following General formula (2), the silane coupling agent composition containing this silicon compound, and the support body which carry | supported this silane coupling agent composition.
(前記一般式(2)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A2は炭素原子数1〜4のアルカンジイル基を表し、Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す) (In the general formula (2), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, A 2 represents an alkanediyl group having 1 to 4 carbon atoms, X represents a group represented by any of the following formulas (X-1) to (X-6), Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or the number of carbon atoms. 1 to 12 linear or branched oxyalkyl group, dimethylamino group, diethylamino group, or ethylmethylamino group)
本発明によれば、優れた熱伝導性を有する熱伝導性硬化物を製造可能な樹脂組成物を提供することができる。また、本発明によれば、優れた熱伝導性を有する熱伝導性硬化物を提供することができる。さらに、本発明によれば、新規なケイ素化合物を提供することができる。この新規なケイ素化合物を用いれば、特に優れた熱伝導性を有する熱伝導性硬化物を製造可能な樹脂組成物に用いられる担持体を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the resin composition which can manufacture the heat conductive hardened | cured material which has the outstanding heat conductivity can be provided. Moreover, according to this invention, the heat conductive hardened | cured material which has the outstanding heat conductivity can be provided. Furthermore, according to the present invention, a novel silicon compound can be provided. By using this novel silicon compound, it is possible to provide a carrier used for a resin composition capable of producing a thermally conductive cured product having particularly excellent thermal conductivity.
本明細書における「担持」とは、化学結合(例えば、共有結合、電気原子価結合、及びイオン結合等)、ファンデルワールス力、静電気力、付着、吸着、固着、及びその他の種類の会合など、シランカップリング剤組成物と被担持体とのあらゆる形態の結合をも意味するものとする。 As used herein, “supported” refers to chemical bonds (eg, covalent bonds, electric valence bonds, and ionic bonds), van der Waals forces, electrostatic forces, adhesion, adsorption, fixation, and other types of associations. In addition, all forms of bonding between the silane coupling agent composition and the support are meant.
本発明の樹脂組成物は、シランカップリング剤組成物を担持した担持体を含有する。そして、シランカップリング剤組成物が、下記一般式(1)で表されるケイ素化合物を含有するものである。 The resin composition of this invention contains the support body which carry | supported the silane coupling agent composition. And a silane coupling agent composition contains the silicon compound represented by following General formula (1).
(前記一般式(1)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A1は単結合又は炭素原子数1〜4のアルカンジイル基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す。Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Xが下記式(X−1)で表される基である場合のZは−NHCO−であり、Xが下記式(X−2)〜(X−6)のいずれかで表される基である場合のZは単結合又は−NHCO−である) (In the general formula (1), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, and A 1 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched oxyalkyl group having 1 to 12 carbon atoms, a dimethylamino group, a diethylamino group, or ethyl Represents a methylamino group, X represents a group represented by any one of the following formulas (X-1) to (X-6), and X represents a group represented by the following formula (X-1). Z is -NHCO-, and Z is a single bond or -NHCO- when X is a group represented by any one of the following formulas (X-2) to (X-6))
上記一般式(1)において、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表す。炭素原子数1〜3の直鎖又は分岐状のアルキル基としては、メチル基、エチル基、プロピル基、及びイソプロピル基が挙げられる。 In the general formula (1), R 1 each independently represents a linear or branched alkyl group having 1 to 3 carbon atoms. Examples of the linear or branched alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
上記一般式(1)において、A1は単結合又は炭素原子数1〜4のアルカンジイル基を表す。炭素原子数1〜4のアルカンジイル基としては、メチレン基、エチレン基、プロピレン基、及びブチレン基が挙げられる。 In the general formula (1), A 1 represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. Examples of the alkanediyl group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, and a butylene group.
上記一般式(1)において、Xは上記式(X−1)〜(X−6)のいずれかで表される基を表す。そして、Xが式(X−1)で表される基である場合のZは、−NHCO−である。また、Xが式(X−2)〜(X−6)で表される基である場合のZは、単結合又は−NHCO−である。 In the general formula (1), X represents a group represented by any one of the above formulas (X-1) to (X-6). Z in the case where X is a group represented by the formula (X-1) is —NHCO—. Z in the case where X is a group represented by formulas (X-2) to (X-6) is a single bond or —NHCO—.
上記一般式(1)において、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す。炭素原子数1〜12の直鎖又は分岐状のアルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、第二ブチル基、第三ブチル基、ペンチル基、アミル基、イソアミル基、ヘキシル基、ヘプチル基、イソヘプチル基、オクチル基、イソオクチル基、2−エチルヘキシル基、ノニル基、イソノニル基、デシル基、及びドデシル基等が挙げられる。また、炭素原子数1〜12の直鎖又は分岐状のオキシアルキル基としては、メチルオキシ、エチルオキシ、プロピルオキシ、イソプロピルオキシ、ブチルオキシ、第二ブチルオキシ、第三ブチルオキシ、イソブチルオキシ、アミルオキシ、イソアミルオキシ、第三アミルオキシ、ヘキシルオキシ、シクロヘキシルオキシ、ヘプチルオキシ、イソヘプチルオキシ、第三ヘプチルオキシ、n−オクチルオキシ、イソオクチルオキシ、第三オクチルオキシ、及び2−エチルヘキシルオキシ等が挙げられる。 In the general formula (1), Y is a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched oxyalkyl group having 1 to 12 carbon atoms, a dimethylamino group, Represents a diethylamino group or an ethylmethylamino group. Examples of the linear or branched alkyl group having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, pentyl group, amyl Group, isoamyl group, hexyl group, heptyl group, isoheptyl group, octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, isononyl group, decyl group, dodecyl group and the like. Examples of the linear or branched oxyalkyl group having 1 to 12 carbon atoms include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, Tertiary amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy and the like.
上記一般式(1)中のZは、−NHCO−であることが好ましい。一般式(1)中のZが−NHCO−であるケイ素化合物を用いると、得られる熱伝導性硬化物の熱伝導度を大きく向上させることができる。また、一般式(1)中のA1がプロピレン基である場合は、経済面から好ましい。 Z in the general formula (1) is preferably —NHCO—. When a silicon compound in which Z in the general formula (1) is —NHCO— is used, the thermal conductivity of the resulting thermally conductive cured product can be greatly improved. Further, when A 1 in the general formula (1) is a propylene group is preferable from the economic.
一般式(1)で表されるケイ素化合物の好ましい具体例としては、下記化学式No.1〜No.99で表される化合物No.1〜No.99が挙げられる。なお、下記化学式中の「Me」はメチル基を表し、「Et」はエチル基を表す。一般式(1)で表されるケイ素化合物には、アゾ基による2つの幾何異性体が存在する場合がある。本発明においてはこれらを区別するものではなく、1つの幾何異性体でもよいし、2つの幾何異性体の混合物であってもよい。 As preferable specific examples of the silicon compound represented by the general formula (1), 1-No. Compound No. 99 1-No. 99. In the following chemical formula, “Me” represents a methyl group, and “Et” represents an ethyl group. The silicon compound represented by the general formula (1) may have two geometric isomers due to an azo group. In the present invention, these are not distinguished, and may be one geometric isomer or a mixture of two geometric isomers.
一般式(1)で表されるケイ素化合物は周知の反応を応用して製造することができ、その製造方法によって何ら限定されるものではない。一般式(1)におけるZが単結合であるケイ素化合物は、例えば、目的化合物に対応する構造のフェニル化合物とトリアルコキシシランを、ヘキサクロロ白金(IV)酸等に代表される触媒存在下で反応させることによって製造することができる。また、一般式(1)におけるZが−NHCO−であるケイ素化合物は、例えば、目的化合物に対応する構造のカルボン酸と3−アミノプロピルトリアルコキシシランに代表されるアミノ基を有するトリアルコキシシランを、塩基性下においてO−(ベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスファートに代表される縮合剤とともに反応させることによって製造することができる。 The silicon compound represented by the general formula (1) can be produced by applying a known reaction, and is not limited by the production method. In the silicon compound in which Z in the general formula (1) is a single bond, for example, a phenyl compound having a structure corresponding to the target compound and trialkoxysilane are reacted in the presence of a catalyst typified by hexachloroplatinic (IV) acid or the like. Can be manufactured. Moreover, the silicon compound in which Z in the general formula (1) is —NHCO— is, for example, a carboxylic acid having a structure corresponding to the target compound and a trialkoxysilane having an amino group represented by 3-aminopropyltrialkoxysilane. And can be produced by reacting with a condensing agent represented by O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate under basic conditions. .
本発明の樹脂組成物は、通常、シランカップリング剤組成物を担持した担持体30〜80質量%と、樹脂成分20〜70質量%(但し、担持体+樹脂成分=100質量%)とを含有する。 The resin composition of the present invention usually comprises 30 to 80% by mass of a carrier carrying a silane coupling agent composition and 20 to 70% by mass of a resin component (provided that the carrier + resin component = 100% by mass). contains.
本発明の樹脂組成物は、例えば、一般式(1)で表されるケイ素化合物を含有するシランカップリング剤組成物を被担持体に担持させたものである。被担持体にシランカップリング剤組成物を担持させる方法としては、公知な方法を用いることができる。例えば、気層吸着、液層吸着等の方法を用いることができる。なお、液層吸着の例として、一般式(1)で表されるケイ素化合物を溶媒に溶解して得た溶液に被担持体を浸漬することで、被担持体にケイ素化合物を吸着させる方法が挙げられる。 The resin composition of the present invention is obtained, for example, by supporting a silane coupling agent composition containing a silicon compound represented by the general formula (1) on a support. As a method of supporting the silane coupling agent composition on the support, a known method can be used. For example, methods such as gas layer adsorption and liquid layer adsorption can be used. In addition, as an example of liquid layer adsorption, there is a method in which a silicon compound is adsorbed on a supported body by immersing the supported body in a solution obtained by dissolving the silicon compound represented by the general formula (1) in a solvent. Can be mentioned.
樹脂成分の種類は特に限定されるものではない。樹脂成分としては、例えば、熱硬化性樹脂や熱可塑性樹脂が挙げられる。なかでも、熱硬化性樹脂が好適に用いられる。熱硬化性樹脂としては、例えば、アミノ樹脂、シアネート樹脂、イソシアネート樹脂、ポリイミド、エポキシ樹脂、オキセタン樹脂、ポリエステル、アリル樹脂、フェノール樹脂、ベンゾオキサジン樹脂、キシレン樹脂、ケトン樹脂、フラン樹脂、COPNA樹脂、ケイ素樹脂、ジシクロペンタジエン樹脂、ベンゾシクロブテン樹脂、エピスルフィド樹脂、エン−チオール樹脂、ポリアゾメチン樹脂、ポリビニルベンジルエーテル、アセナフチレンなどが挙げられる。なかでも、樹脂成分としては、シアネート樹脂、イソシアネート樹脂、エポキシ樹脂、フェノール樹脂が好ましい。 The kind of resin component is not particularly limited. Examples of the resin component include a thermosetting resin and a thermoplastic resin. Among these, a thermosetting resin is preferably used. Examples of the thermosetting resin include amino resin, cyanate resin, isocyanate resin, polyimide, epoxy resin, oxetane resin, polyester, allyl resin, phenol resin, benzoxazine resin, xylene resin, ketone resin, furan resin, COPNA resin, Examples of the resin include silicon resin, dicyclopentadiene resin, benzocyclobutene resin, episulfide resin, ene-thiol resin, polyazomethine resin, polyvinyl benzyl ether, and acenaphthylene. Especially, as a resin component, cyanate resin, isocyanate resin, an epoxy resin, and a phenol resin are preferable.
シアネート樹脂としては、例えば、ハロゲン化シアン化合物と、フェノール類やナフトール類とを反応させ、必要に応じて加熱等してプレポリマー化することにより得られるシアネート樹脂などがある。シアネート樹脂としては、例えば、ノボラック型シアネート樹脂、ビスフェノールA型シアネート樹脂、ビスフェノールE型シアネート樹脂、テトラメチルビスフェノールF型シアネート樹脂等のビスフェノール型シアネート樹脂、及びナフトールアラルキル型シアネート樹脂等を挙げることができる。より具体的には、2,2’−ビス(4−シアナトフェニル)イソプロピリデン、1,1’−ビス(4−シアナトフェニル)エタン、ビス(4−シアナト−3,5−ジメチルフェニル)メタン、1,3−ビス(4−シアナトフェニル−1−(1−メチルエチリデン))ベンゼン、ジシクロペンタジエン型シアネートエステル、フェノールノボラック型シアネートエステル、ビス(4−シアナトフェニル)チオエーテル、ビス(4−シアナトフェニル)エーテル、1,1,1−トリス(4−シアナトフェニル)エタン、トリス(4−シアナトフェニル)ホスファイト、ビス(4−シアナトフェニル)スルホン、2,2−ビス(4−シアナトフェニル)プロパン、1,3−、1,4−、1,6−、1,8−、2,6−又は2,7−ジシアナトナフタレン、1,3,6−トリシアナトナフタレン、4,4−ジシアナトビフェニル、及びフェノールノボラック型、クレゾールノボラック型の多価フェノール類と、ハロゲン化シアンとの反応で得られるシアネート樹脂;ナフトールアラルキル型の多価ナフトール類と、ハロゲン化シアンとの反応で得られるシアネート樹脂等が挙げられる。 Examples of the cyanate resin include a cyanate resin obtained by reacting a halogenated cyanide compound with phenols or naphthols and prepolymerizing them by heating as necessary. Examples of the cyanate resin include novolak type cyanate resin, bisphenol A type cyanate resin, bisphenol E type cyanate resin, bisphenol type cyanate resin such as tetramethylbisphenol F type cyanate resin, and naphthol aralkyl type cyanate resin. . More specifically, 2,2′-bis (4-cyanatophenyl) isopropylidene, 1,1′-bis (4-cyanatophenyl) ethane, bis (4-cyanato-3,5-dimethylphenyl) Methane, 1,3-bis (4-cyanatophenyl-1- (1-methylethylidene)) benzene, dicyclopentadiene type cyanate ester, phenol novolac type cyanate ester, bis (4-cyanatophenyl) thioether, bis ( 4-cyanatophenyl) ether, 1,1,1-tris (4-cyanatophenyl) ethane, tris (4-cyanatophenyl) phosphite, bis (4-cyanatophenyl) sulfone, 2,2-bis (4-Cyanatophenyl) propane, 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphtha 1,3,6-tricyanatonaphthalene, 4,4-dicyanatobiphenyl, and phenol novolac-type and cresol novolac-type polyhydric phenols and cyanate resins obtained by reaction with cyanogen halides; naphthol aralkyl type And cyanate resins obtained by reacting polyvalent naphthols with cyanogen halides.
イソシアネート樹脂としては、例えば、フェノール類とハロゲン化シアンとの脱ハロゲン化水素反応により得られるイソシアネート樹脂がある。イソシアネート樹脂としては、例えば、4,4’−ジフェニルメタンジイソシアネートMDI、ポリメチレンポリフェニルポリイソシアネート、トリレンジイソシアネート、ヘキサメチレンジイソシアネート等が挙げられる。 Examples of the isocyanate resin include an isocyanate resin obtained by a dehydrohalogenation reaction between a phenol and a cyanogen halide. Examples of the isocyanate resin include 4,4'-diphenylmethane diisocyanate MDI, polymethylene polyphenyl polyisocyanate, tolylene diisocyanate, hexamethylene diisocyanate, and the like.
エポキシ樹脂としては、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(ビスフェノールA)、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3−ビス(4−ヒドロキシクミルベンゼン)、1,4−ビス(4−ヒドロキシクミルベンゼン)、1,1,3−トリス(4−ヒドロキシフェニル)ブタン、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物;エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール、ビスフェノールA−エチレンオキシド付加物等の多価アルコール類のポリグリシジルエーテル;マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族又は脂環族多塩基酸のグリシジルエステル類、及びグリシジルメタクリレートの単独重合体又は共重合体;N,N−ジグリシジルアニリン、ビス(4−(N−メチル−N−グリシジルアミノ)フェニル)メタン、ジグリシジルオルトトルイジン等のグリシジルアミノ基を有するエポキシ化合物;ビニルシクロヘキセンジエポキシド、ジシクロペンタンジエンジエポキサイド、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−6−メチルシクロヘキシルメチル−6−メチルシクロヘキサンカルボキシレート、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート等の環状オレフィン化合物のエポキシ化物;エポキシ化ポリブタジエン、エポキシ化スチレン−ブタジエン共重合物等のエポキシ化共役ジエン重合体、トリグリシジルイソシアヌレート等の複素環化合物が挙げられる。なかでも、ナフタレン型エポキシやビスフェノールA型エポキシが好ましい。 Examples of the epoxy resin include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcin, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F), methylene bis (orthocresol), Ethylidene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis (orthocresol), tetrabromobisphenol A, 1,3-bis (4-hydroxycumylbenzene), 1,4-bis (4-hydroxycumylbenzene) ), 1,1,3-tris (4-hydroxyphenyl) butane, 1,1,2,2-tetra (4-hydroxyphenyl) ethane, thiobisphenol, sulfobisphenol, oxy Polyglycidyl ether compounds of polynuclear polyhydric phenol compounds such as bisphenol, phenol novolak, orthocresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcin novolak, terpene phenol; ethylene glycol, propylene glycol, butylene glycol, hexanediol, poly Polyglycidyl ethers of polyhydric alcohols such as glycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-ethylene oxide adduct; maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberin Acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, Glycidyl esters of aliphatic, aromatic or alicyclic polybasic acids such as sophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid, endomethylenetetrahydrophthalic acid, And glycidyl methacrylate homopolymer or copolymer; N, N-diglycidylaniline, bis (4- (N-methyl-N-glycidylamino) phenyl) methane, epoxy having a glycidylamino group such as diglycidylorthotoluidine Compound: Vinylcyclohexene diepoxide, dicyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexane Epoxidized products of cyclic olefin compounds such as ruboxylate and bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymer, triglycidyl isocyanate And heterocyclic compounds such as nurate. Of these, naphthalene type epoxy and bisphenol A type epoxy are preferable.
フェノール樹脂としては、フェノール類とアルデヒド類より合成されるフェノール樹脂がある。フェノール類としては、例えば、フェノール、クレゾール、エチルフェノール、n−プロピルフェノール、イソプロピルフェノール、ブチルフェノール、第三ブチルフェノール、オクチルフェノール、ノニルフェノール、ドデシルフェノール、シクロヘキシルフェノール、クロロフェノール、ブロモフェノール、レゾルシン、カテコール、ハイドロキノン、2,2−ビス(4−ヒドロキシフェニル)プロパン、4,4’−チオジフェノール、ジヒドロキシジフェニルメタン、ナフトール、テルペンフェノール、フェノール化ジシクロペンタジエン等が挙げられる。また、アルデヒド類としては、ホルムアルデヒドが挙げられる。 As a phenol resin, there is a phenol resin synthesized from phenols and aldehydes. Examples of phenols include phenol, cresol, ethylphenol, n-propylphenol, isopropylphenol, butylphenol, tert-butylphenol, octylphenol, nonylphenol, dodecylphenol, cyclohexylphenol, chlorophenol, bromophenol, resorcin, catechol, hydroquinone, Examples include 2,2-bis (4-hydroxyphenyl) propane, 4,4′-thiodiphenol, dihydroxydiphenylmethane, naphthol, terpenephenol, and phenolized dicyclopentadiene. Moreover, formaldehyde is mentioned as aldehydes.
本発明の樹脂組成物には、必要に応じて種々の添加物を添加することができる。添加物としては、例えば、エポキシ樹脂に使用される硬化剤;天然ワックス類、合成ワックス類、長鎖脂肪族酸の金属塩類等の可塑剤;酸アミド類、エステル類、パラフィン類などの離型剤;ニトリルゴム、ブタジエンゴム等の応力緩和剤;三酸化アンチモン、五酸化アンチモン、酸化錫、水酸化錫、酸化モリブデン、硼酸亜鉛、メタ硼酸バリウム、赤燐、水酸化アルミニウム、水酸化マグネシウム、アルミン酸カルシウム等の無機難燃剤;テトラブロモビスフェノールA、テトラブロモ無水フタル酸、ヘキサブロモベンゼン、ブロム化フェノールノボラック等の臭素系難燃剤;リン系難燃剤;染料や顔料等の着色剤;酸化安定剤、光安定剤、耐湿性向上剤、チキソトロピー付与剤、希釈剤、消泡剤、他の各種の樹脂、粘着付与剤、帯電防止剤、滑剤、紫外線吸収剤等があげられる。さらには、アルコール類、エーテル類、アセタール類、ケトン類、エステル類、アルコールエステル類、ケトンアルコール類、エーテルアルコール類、ケトンエーテル類、ケトンエステル類、エステルエーテル類、芳香族系溶剤などの有機溶剤等を配合することもできる。 Various additives can be added to the resin composition of the present invention as necessary. Examples of additives include curing agents used for epoxy resins; plasticizers such as natural waxes, synthetic waxes, and metal salts of long-chain aliphatic acids; mold release such as acid amides, esters, and paraffins. Agents: Stress relaxation agents such as nitrile rubber and butadiene rubber; antimony trioxide, antimony pentoxide, tin oxide, tin hydroxide, molybdenum oxide, zinc borate, barium metaborate, red phosphorus, aluminum hydroxide, magnesium hydroxide, aluminum Inorganic flame retardants such as calcium acid; brominated flame retardants such as tetrabromobisphenol A, tetrabromophthalic anhydride, hexabromobenzene, brominated phenol novolak; phosphorus flame retardants; colorants such as dyes and pigments; oxidation stabilizers; Light stabilizer, moisture resistance improver, thixotropy imparting agent, diluent, antifoaming agent, other various resins, tackifier, antistatic , Lubricants, ultraviolet absorbers, and the like. Furthermore, organic solvents such as alcohols, ethers, acetals, ketones, esters, alcohol esters, ketone alcohols, ether alcohols, ketone ethers, ketone esters, ester ethers, aromatic solvents, etc. Etc. can also be blended.
エポキシ樹脂に使用される硬化剤としては、潜在性硬化剤、酸無水物、ポリアミン化合物、ポリフェノール化合物、及びカチオン系光開始剤などが挙げられる。 Examples of the curing agent used in the epoxy resin include a latent curing agent, an acid anhydride, a polyamine compound, a polyphenol compound, and a cationic photoinitiator.
潜在性硬化剤としては、ジシアンジアミド、ヒドラジド、イミダゾール化合物、アミンアダクト、スルホニウム塩、オニウム塩、ケチミン、酸無水物、三級アミンなどが挙げられる。これらの潜在性硬化剤を使用した場合には、本発明の樹脂組成物を、取り扱いが容易な一液型の硬化性組成物とすることができるので好ましい。 Examples of the latent curing agent include dicyandiamide, hydrazide, imidazole compound, amine adduct, sulfonium salt, onium salt, ketimine, acid anhydride, and tertiary amine. When these latent hardeners are used, the resin composition of the present invention is preferable because it can be a one-component curable composition that is easy to handle.
酸無水物としては、フタル酸無水物、トリメリット酸無水物、ピロメリット酸無水物、テトラヒドロフタル酸無水物、ヘキサヒドロフタル酸無水物、マレイン酸無水物、コハク酸無水物、2,2−ビス(3,4−ジカルボキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン二無水物などが挙げられる。 Examples of acid anhydrides include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, succinic anhydride, 2,2- And bis (3,4-dicarboxyphenyl) -1,1,1,3,3,3-hexafluoropropane dianhydride.
ポリアミン化合物としては、エチレンジアミン、ジエチレントリアミン、トリエチレンテトラミンなどの脂肪族ポリアミン;メンセンジアミン、イソホロンジアミン、ビス(4−アミノ−3−メチルシクロヘキシル)メタン、ビス(アミノメチル)シクロヘキサン、3,9−ビス(3−アミノプロピル)2,4,8,10−テトラオキサスピロ[5,5]ウンデカンなどの脂環族ポリアミン;m−キシレンジアミンなどの芳香環を有する脂肪族アミン;m−フェニレンジアミン、2,2−ビス(4−アミノフェニル)プロパン、ジアミノジフェニルメタン、ジアミノジフェニルスルホン、α,α−ビス(4−アミノフェニル)−p−ジイソプロピルベンゼン、2,2−ビス(4−アミノフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパンなどの芳香族ポリアミンが挙げられる。 Examples of polyamine compounds include aliphatic polyamines such as ethylenediamine, diethylenetriamine, and triethylenetetramine; mensendiamine, isophoronediamine, bis (4-amino-3-methylcyclohexyl) methane, bis (aminomethyl) cyclohexane, and 3,9-bis. (3-aminopropyl) 2,4,8,10-tetraoxaspiro [5,5] undecane and other alicyclic polyamines; m-xylenediamine and other aliphatic amines; m-phenylenediamine, 2 , 2-bis (4-aminophenyl) propane, diaminodiphenylmethane, diaminodiphenylsulfone, α, α-bis (4-aminophenyl) -p-diisopropylbenzene, 2,2-bis (4-aminophenyl) -1, 1,1,3,3,3-hexafluoropropyl Aromatic polyamines such as lopan are mentioned.
ポリフェノール化合物としては、フェノールノボラック、o−クレゾールノボラック、t−ブチルフェノールノボラック、ジシクロペンタジエンクレゾール、テルペンジフェノール、テルペンジカテコール、1,1,3−トリス(3−第三ブチル−4−ヒドロキシ−6−メチルフェニル)ブタン、ブチリデンビス(3−第三ブチル−4−ヒドロキシ−6−メチルフェニル)、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパンなどが挙げられる。 Examples of the polyphenol compound include phenol novolak, o-cresol novolak, t-butylphenol novolak, dicyclopentadiene cresol, terpene diphenol, terpene dicatechol, 1,1,3-tris (3-tert-butyl-4-hydroxy-6 -Methylphenyl) butane, butylidenebis (3-tert-butyl-4-hydroxy-6-methylphenyl), 2,2-bis (4-hydroxyphenyl) -1,1,1,3,3,3-hexafluoro Examples include propane.
イミダゾール化合物としては、2−メチルイミダゾール、2−フェニルイミダゾール、2−ウンデシルイミダゾール、2−ヘプタデシルイミダゾール、2−フェニル−4−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−メチルイミダゾール、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−ウンデシルイミダゾール、2,4−ジアミノ−6(2’−メチルイミダゾール(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ール(1’))エチル−s−トリアジン、2,4−ジアミノ−6(2’−エチル,4−メチルイミダゾール(1’))エチル−s−トリアジン、2,4−ジアミノ−6(2’−メチルイミダゾール(1’))エチル−s−トリアジン・イソシアヌル酸付加物、2−メチルイミダゾールイソシアヌル酸の2:3付加物、2−フェニルイミダゾールイソシアヌル酸付加物、2−フェニル−3,5−ジヒドロキシメチルイミダゾール、2−フェニル−4−ヒドロキシメチル−5−メチルイミダゾール、1−シアノエチル−2−フェニル−3,5−ジシアノエトキシメチルイミダゾールの各種イミダゾール類;これらイミダゾール類と、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、ピロメリット酸、ナフタレンジカルボン酸、マレイン酸、蓚酸等の多価カルボン酸との塩類が挙げられる。 Examples of imidazole compounds include 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2. -Methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 2,4-diamino-6 (2'-methylimidazole (1 ')) Ethyl-s-triazine, 2,4-diamino-6 (2′-undecylimidazole (1 ′)) ethyl-s-triazine, 2,4-diamino-6 (2′-ethyl, 4-methylimidazole (1 ')) Ethyl-s-triazine, 2,4-diamino-6 (2' Methylimidazole (1 ′)) ethyl-s-triazine isocyanuric acid adduct, 2-methylimidazole isocyanuric acid 2: 3 adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-3,5-dihydroxymethyl Various imidazoles such as imidazole, 2-phenyl-4-hydroxymethyl-5-methylimidazole, 1-cyanoethyl-2-phenyl-3,5-dicyanoethoxymethylimidazole; these imidazoles and phthalic acid, isophthalic acid, terephthalic acid And salts with polyvalent carboxylic acids such as trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, maleic acid, and succinic acid.
本発明の樹脂組成物を硬化させることで、良好な熱伝導性を示す硬化物を得ることができる。また、適宜組成を選定することによって、塗布性、低タック性、硬化前の塗膜の可撓性、硬化後の硬化物の可撓性、基材への密着性などを付与することができる。したがって、本発明の樹脂組成物を硬化させて得られる熱伝導性硬化物は、プリント配線基板、半導体封止絶縁材、パワー半導体、LED照明、LEDバックライト、パワーLED、太陽電池等の電気・電子分野の種々の部材の樹脂基材として広く応用することができる。より具体的には、プリプレグ、封止剤、積層基板、塗布性の接着剤、接着シート等、これらの硬化性成分、及び各種塗料の硬化性成分として有用である。 By curing the resin composition of the present invention, a cured product exhibiting good thermal conductivity can be obtained. In addition, by appropriately selecting the composition, it is possible to impart applicability, low tackiness, flexibility of the coating film before curing, flexibility of the cured product after curing, adhesion to the substrate, and the like. . Therefore, the thermally conductive cured product obtained by curing the resin composition of the present invention is a printed circuit board, a semiconductor sealing insulating material, a power semiconductor, LED lighting, an LED backlight, a power LED, a solar cell, etc. It can be widely applied as a resin base material for various members in the electronic field. More specifically, it is useful as a prepreg, a sealant, a laminated substrate, a coating adhesive, an adhesive sheet, and the like, and these curable components and curable components of various paints.
本発明の熱伝導性硬化物は、上記の本発明の樹脂組成物を硬化させて得られる硬化物である。熱伝導性硬化物の形状は特に限定されないが、例えば、シート状、フィルム状、板状などが挙げられる。シート状の硬化物は、上記の本発明の樹脂組成物をキャリアフィルム、金属箔等の支持体上に膜状に塗布した後、硬化させることによって製造することができる。本発明の熱伝導性硬化物は、原料となる樹脂組成物が有機溶剤を含有する場合、溶剤が残留している状態の硬化物と、溶剤を揮発させて溶剤を実質的に含まない状態の硬化物の両方を含む。 The thermally conductive cured product of the present invention is a cured product obtained by curing the above resin composition of the present invention. The shape of the thermally conductive cured product is not particularly limited, and examples thereof include a sheet shape, a film shape, and a plate shape. The sheet-like cured product can be produced by coating the resin composition of the present invention on a support such as a carrier film or a metal foil, and then curing it. When the resin composition as a raw material contains an organic solvent, the thermally conductive cured product of the present invention is a cured product in a state in which the solvent remains, and a state in which the solvent is volatilized to substantially contain no solvent. Includes both cured products.
本発明の熱伝導性硬化物は、周知の方法を適用することで製造することができる。例えば、熱伝導性硬化物の形状がシート状である場合には、樹脂組成物を支持体上に塗工して形成した塗工膜を硬化させればよい。支持体上への樹脂組成物の塗工は、塗工装置やスプレー装置を使用することができる。塗工装置としては、ロールコーター、バーコーター、ナイフコーター、グラビアコーター、ダイコーター、コンマコーター、カーテンコーター、スクリーン印刷装置、及び刷毛などが挙げられる。 The thermally conductive cured product of the present invention can be produced by applying a known method. For example, when the shape of the thermally conductive cured product is a sheet, a coating film formed by coating the resin composition on the support may be cured. For coating the resin composition on the support, a coating device or a spray device can be used. Examples of the coating apparatus include a roll coater, a bar coater, a knife coater, a gravure coater, a die coater, a comma coater, a curtain coater, a screen printing apparatus, and a brush.
シート状の熱伝導性硬化物を製造する場合、取扱いが容易な支持体を選択して用いることが好ましい。また、シート状の熱伝導性硬化物を支持体から剥離して使用する場合には、熱伝導性硬化物の剥離が容易な支持体を選択して用いることが好ましい。支持体としては、キャリアフィルムが好適である。キャリアフィルムとしては、例えば、ポリエチレンテレフタレート、ポリブチレンテレフタレートなどのポリエステル樹脂;フッ素系樹脂、ポリイミド樹脂などの耐熱性を有する熱可塑性樹脂からなるフィルムが好適に選択される。 When producing a sheet-like thermally conductive cured product, it is preferable to select and use a support that is easy to handle. When the sheet-like thermally conductive cured product is peeled from the support and used, it is preferable to select and use a support from which the thermally conductive cured product can be easily peeled. As the support, a carrier film is suitable. As the carrier film, for example, a polyester resin such as polyethylene terephthalate or polybutylene terephthalate; a film made of a heat-resistant thermoplastic resin such as a fluorine resin or a polyimide resin is preferably selected.
また、支持体として金属箔を用いた場合には、形成した熱伝導性硬化物を金属箔から剥離して用いてもよいし、剥離させることなく金属箔をエッチングして用いてもよい。金属箔としては、例えば、銅、銅系合金、アルミ、アルミ系合金、鉄、鉄系合金、銀、銀系合金、金、金系合金、亜鉛、亜鉛系合金、ニッケル、ニッケル系合金、錫、錫系合金等からなる金属箔が好適に用いられる。また、金属箔として、キャリア箔付き極薄金属箔を用いてもよい。 When a metal foil is used as the support, the formed thermally conductive cured product may be peeled off from the metal foil, or may be used after being etched without being peeled off. Examples of metal foils include copper, copper alloys, aluminum, aluminum alloys, iron, iron alloys, silver, silver alloys, gold, gold alloys, zinc, zinc alloys, nickel, nickel alloys, tin A metal foil made of tin alloy or the like is preferably used. Moreover, you may use ultrathin metal foil with carrier foil as metal foil.
本発明の熱伝導性硬化物の形状がシート状である場合において、シート状の熱伝導性硬化物の厚さは用途により適宜設定すればよいが、通常、20〜150μmの範囲である。 When the shape of the thermally conductive cured product of the present invention is a sheet shape, the thickness of the sheet-like thermally conductive cured product may be appropriately set depending on the application, but is usually in the range of 20 to 150 μm.
本発明の熱伝導性硬化物は良好な熱伝導性を示すため、プリント配線基板、半導体封止絶縁材、パワー半導体、LED照明、LEDバックライト、パワーLED、太陽電池等の電気・電子分野の種々の部材の樹脂基材として広く応用が可能である。より具体的には、プリプレグ、封止剤、積層基板、塗布性の接着剤、放熱シート、接着シート等に用いることができる。 Since the thermally conductive cured product of the present invention exhibits good thermal conductivity, it is used in the electrical and electronic fields such as printed wiring boards, semiconductor sealing insulating materials, power semiconductors, LED lighting, LED backlights, power LEDs, and solar cells. It can be widely applied as a resin base material for various members. More specifically, it can be used for prepregs, sealants, laminated substrates, coatable adhesives, heat dissipation sheets, adhesive sheets and the like.
本発明のケイ素化合物は、下記一般式(2)で表される。本発明のケイ素化合物は、熱伝導性硬化物の製造原料として用いられる樹脂組成物に配合される熱伝導性フィラーに担持されるシランカップリング剤として特に好適である。 The silicon compound of the present invention is represented by the following general formula (2). The silicon compound of the present invention is particularly suitable as a silane coupling agent supported on a heat conductive filler blended in a resin composition used as a raw material for producing a heat conductive cured product.
(前記一般式(2)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A2は炭素原子数1〜4のアルカンジイル基を表し、Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す) (In the general formula (2), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, A 2 represents an alkanediyl group having 1 to 4 carbon atoms, X represents a group represented by any of the following formulas (X-1) to (X-6), Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or the number of carbon atoms. 1 to 12 linear or branched oxyalkyl group, dimethylamino group, diethylamino group, or ethylmethylamino group)
一般式(2)中のR1、Y及びXは、前述の一般式(1)中のR1、Y及びXとそれぞれ同義である。また、一般式(2)において、A2は炭素原子数1〜4のアルカンジイル基を表す。炭素原子数1〜4のアルカンジイル基としては、メチレン基、エチレン基、プロピレン基、ブチレン基が挙げられる。 R 1, Y and X in the general formula (2) in is each and R 1, Y and X in the above general formula (1) synonymous. In the general formula (2), A 2 represents an alkanediyl group having 1 to 4 carbon atoms. Examples of the alkanediyl group having 1 to 4 carbon atoms include a methylene group, an ethylene group, a propylene group, and a butylene group.
一般式(2)中のXは、式(X−1)、式(X−3)、式(X−4)又は式(X−6)で表される基であることが好ましい。一般式(2)中のXが式(X−1)、式(X−3)、式(X−4)又は式(X−6)で表される基であるケイ素化合物を用いると、得られる熱伝導性硬化物の熱伝導度を大きく向上させることができる。また、一般式(2)中のA2がプロピレン基である場合は、経済面から好ましい。 X in General Formula (2) is preferably a group represented by Formula (X-1), Formula (X-3), Formula (X-4), or Formula (X-6). When a silicon compound in which X in the general formula (2) is a group represented by the formula (X-1), the formula (X-3), the formula (X-4), or the formula (X-6) is obtained, The thermal conductivity of the thermally conductive cured product obtained can be greatly improved. Further, when A 2 in the general formula (2) is a propylene group is preferable from the economic.
一般式(2)で表されるケイ素化合物の好ましい具体例としては、前記化学式No.1〜No.54で表される化合物No.1〜No.54が挙げられる。なお、前記一般式(2)で表されるケイ素化合物には、アゾ基による2つの幾何異性体が存在する場合がある。本発明においてはこれらを区別するものではなく、1つの幾何異性体でもよいし、2つの幾何異性体の混合物であってもよい。 Preferable specific examples of the silicon compound represented by the general formula (2) include the chemical formula No. 1 described above. 1-No. Compound No. 54. 1-No. 54. The silicon compound represented by the general formula (2) may have two geometric isomers due to an azo group. In the present invention, these are not distinguished, and may be one geometric isomer or a mixture of two geometric isomers.
一般式(2)で表されるケイ素化合物は周知の反応を応用して製造することができ、その製造方法によって何ら限定されるものではない。一般式(2)で表されるケイ素化合物は、例えば、目的化合物に対応する構造のカルボン酸と3−アミノプロピルトリアルコキシシランに代表されるアミノ基を有するトリアルコキシシランを、塩基性下においてO−(ベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスファートに代表される縮合剤とともに反応させることによって製造することができる。 The silicon compound represented by the general formula (2) can be produced by applying a known reaction, and is not limited at all by the production method. The silicon compound represented by the general formula (2) is, for example, a carboxylic acid having a structure corresponding to the target compound and a trialkoxysilane having an amino group typified by 3-aminopropyltrialkoxysilane. It can be produced by reacting with a condensing agent typified by-(benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate.
本発明のケイ素化合物は、熱伝導性フィラー用のシランカップリング剤として好適に用いられる。本発明のケイ素化合物は、熱伝導性フィラー用のシランカップリング剤の他に、光学記録材料、医薬品、農薬、香料、染料等の合成中間体;各種機能性材料、各種ポリマー原料;光電気化学電池、非線形光学装置、エレクトロクロミックディスプレイ、ホログラム、有機半導体、有機EL;ハロゲン化銀写真感光材料、光増感剤;印刷インキ、インクジェット、電子写真カラートナー、化粧料、プラスチック等に用いられる着色剤;タンパク質用染色剤、物質検出のための発光染料;合成石英原料、塗料、合成触媒、触媒担体、表面コート薄膜材料、シリコーンゴム架橋剤、粘結剤等としても好適に用いられる。 The silicon compound of the present invention is suitably used as a silane coupling agent for a thermally conductive filler. In addition to the silane coupling agent for the thermally conductive filler, the silicon compound of the present invention includes synthetic intermediates such as optical recording materials, pharmaceuticals, agricultural chemicals, fragrances, and dyes; various functional materials, various polymer raw materials; photoelectrochemistry Batteries, nonlinear optical devices, electrochromic displays, holograms, organic semiconductors, organic ELs; silver halide photographic light-sensitive materials, photosensitizers; colorants used in printing inks, ink jets, electrophotographic color toners, cosmetics, plastics, etc. Protein dyes, luminescent dyes for substance detection; synthetic quartz raw materials, paints, synthetic catalysts, catalyst carriers, surface coat thin film materials, silicone rubber cross-linking agents, binders, and the like.
本発明のシランカップリング剤組成物は、一般式(2)で表される本発明のケイ素化合物を含有するものであり、例えば、被担持体に担持させることができる。本発明のシランカップリング剤組成物は、一般式(2)で表されるケイ素化合物以外の成分として有機溶剤をさらに含有してもよい。 The silane coupling agent composition of the present invention contains the silicon compound of the present invention represented by the general formula (2), and can be supported on a supported body, for example. The silane coupling agent composition of the present invention may further contain an organic solvent as a component other than the silicon compound represented by the general formula (2).
被担持体にシランカップリング剤を担持させる方法としては、公知な方法を用いることができる。例えば、気層吸着、液層吸着等の方法を用いることができる。なお、液層吸着の例として、本発明のケイ素化合物を溶媒に溶解して得た溶液に被担持体を浸漬することで、被担持体にケイ素化合物を吸着させる方法が挙げられる。 As a method for supporting the silane coupling agent on the support, a known method can be used. For example, methods such as gas layer adsorption and liquid layer adsorption can be used. An example of liquid layer adsorption includes a method in which a silicon compound is adsorbed on a supported body by immersing the supported body in a solution obtained by dissolving the silicon compound of the present invention in a solvent.
例えば、窒化アルミニウム等の熱伝導性フィラーをエポキシ樹脂中に分散させた樹脂組成物を製造する場合、この熱伝導性フィラーに本発明のシランカップリング剤組成物を担持させると、熱伝導性フィラーの分散性が向上する。また、本発明のシランカップリング剤組成物を担持させた窒化アルミニウムフィラーをエポキシ樹脂中に分散させた樹脂組成物を製造し、この樹脂組成物を硬化させて得た熱伝導性硬化物については、熱伝導性が大きく向上している。さらに、熱伝導性硬化物の形状がシート状である場合には、ボイドの発生や、絶縁破壊電圧の低下、破断伸度の低下によるシートの強靱性の低下等を防止することもできる。 For example, when producing a resin composition in which a thermally conductive filler such as aluminum nitride is dispersed in an epoxy resin, the thermal conductive filler is supported by supporting the silane coupling agent composition of the present invention on the thermally conductive filler. The dispersibility of is improved. Moreover, about the heat conductive hardened | cured material obtained by manufacturing the resin composition which disperse | distributed the aluminum nitride filler which carry | supported the silane coupling agent composition of this invention in the epoxy resin, and hardening this resin composition. The thermal conductivity is greatly improved. Furthermore, when the thermally conductive cured product is in the form of a sheet, it is possible to prevent voids from being generated, a decrease in dielectric breakdown voltage, a decrease in sheet toughness due to a decrease in elongation at break, and the like.
本発明のシランカップリング剤組成物に含有させることができる有機溶剤としては、アルコール系溶剤、ジオール系溶剤、ケトン系溶剤、エステル系溶剤、エーテル系溶剤、脂肪族又は脂環族炭化水素系溶剤、芳香族炭化水素系溶剤、シアノ基を有する炭化水素溶剤、ハロゲン化芳香族炭化水素系剤、その他の溶剤等が挙げられる。 Examples of the organic solvent that can be contained in the silane coupling agent composition of the present invention include alcohol solvents, diol solvents, ketone solvents, ester solvents, ether solvents, aliphatic or alicyclic hydrocarbon solvents. , Aromatic hydrocarbon solvents, hydrocarbon solvents having a cyano group, halogenated aromatic hydrocarbon agents, and other solvents.
アルコール系溶剤としては、メタノール、エタノール、プロパノール、2−プロパノール、1−ブタノール、イソブタノール、2−ブタノール、第三ブタノール、ペンタノール、イソペンタノール、2−ペンタノール、ネオペンタノール、第三ペンタノール、ヘキサノール、2−ヘキサノール、ヘプタノール、2−ヘプタノール、オクタノール、2―エチルヘキサノール、2−オクタノール、シクロペンタノール、シクロヘキサノール、シクロヘプタノール、メチルシクロペンタノール、メチルシクロヘキサノール、メチルシクロヘプタノール、ベンジルアルコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングルコールモノエチルエーテル、ジエチレングルコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、2−(N,N−ジメチルアミノ)エタノール、3(N,N−ジメチルアミノ)プロパノール等が挙げられる。 Examples of alcohol solvents include methanol, ethanol, propanol, 2-propanol, 1-butanol, isobutanol, 2-butanol, tert-butanol, pentanol, isopentanol, 2-pentanol, neopentanol, and third pen. Tanol, hexanol, 2-hexanol, heptanol, 2-heptanol, octanol, 2-ethylhexanol, 2-octanol, cyclopentanol, cyclohexanol, cycloheptanol, methylcyclopentanol, methylcyclohexanol, methylcycloheptanol, Benzyl alcohol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, Examples include ethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, 2- (N, N-dimethylamino) ethanol, and 3 (N, N-dimethylamino) propanol. .
ジオール系溶剤としては、エチレングリコール、プロピレングリコール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、ネオペンチルグリコール、イソプレングリコール(3−メチル−1,3−ブタンジオール)、1,2−ヘキサンジオール、1,6−ヘキサンジオール、3−メチル−1,5−ペンタンジオール、1,2−オクタンジオール、オクタンジオール(2−エチル−1,3−ヘキサンジオール)、2−ブチル−2−エチル−1,3−プロパンジオール、2,5−ジメチル−2,5−ヘキサンジオール、1,2−シクロヘキサンジオール、1,4−シクロヘキサンジオール、1,4−シクロヘキサンジメタノール等が挙げられる。 Examples of the diol solvent include ethylene glycol, propylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, isoprene glycol (3-methyl -1,3-butanediol), 1,2-hexanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,2-octanediol, octanediol (2-ethyl-1, 3-hexanediol), 2-butyl-2-ethyl-1,3-propanediol, 2,5-dimethyl-2,5-hexanediol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1, 4-cyclohexanedimethanol etc. are mentioned.
ケトン系溶剤としては、アセトン、エチルメチルケトン、メチルイソプロピルケトン、メチルブチルケトン、メチルイソブチルケトン、メチルアミルケトン、メチルヘキシルケトン、エチルブチルケトン、ジエチルケトン、ジプロピルケトン、ジイソブチルケトン、メチルアミルケトン、シクロヘキサノン、メチルシクロヘキサノン等が挙げられる。 Examples of ketone solvents include acetone, ethyl methyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl hexyl ketone, ethyl butyl ketone, diethyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, Examples include cyclohexanone and methylcyclohexanone.
エステル系溶剤としては、ギ酸メチル、ギ酸エチル、酢酸メチル、酢酸エチル、酢酸イソプロピル、酢酸ブチル、酢酸イソブチル、酢酸第二ブチル、酢酸第三ブチル、酢酸アミル、酢酸イソアミル、酢酸第三アミル、酢酸フェニル、プロピオン酸メチル、プロピオン酸エチル、プロピオン酸イソプロピル、プロピオン酸ブチル、プロピオン酸イソブチル、プロピオン酸第二ブチル、プロピオン酸第三ブチル、プロピオン酸アミル、プロピオン酸イソアミル、プロピオン酸第三アミル、プロピオン酸フェニル、2−エチルヘキサン酸メチル、2−エチルヘキサン酸エチル、2−エチルヘキサン酸プロピル、2−エチルヘキサン酸イソプロピル、2−エチルヘキサン酸ブチル、乳酸メチル、乳酸エチル、メトキシプロピオン酸メチル、エトキシプロピオン酸メチル、メトキシプロピオン酸エチル、エトキシプロピオン酸エチル、エチレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノプロピルエーテルアセテート、エチレングリコールモノイソプロピルエーテルアセテート、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノ第二ブチルエーテルアセテート、エチレングリコールモノイソブチルエーテルアセテート、エチレングリコールモノ第三ブチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノプロピルエーテルアセテート、プロピレングリコールモノイソプロピルエーテルアセテート、プロピレングリコールモノブチルエーテルアセテート、プロピレングリコールモノ第二ブチルエーテルアセテート、プロピレングリコールモノイソブチルエーテルアセテート、プロピレングリコールモノ第三ブチルエーテルアセテート、ブチレングリコールモノメチルエーテルアセテート、ブチレングリコールモノエチルエーテルアセテート、ブチレングリコールモノプロピルエーテルアセテート、ブチレングリコールモノイソプロピルエーテルアセテート、ブチレングリコールモノブチルエーテルアセテート、ブチレングリコールモノ第二ブチルエーテルアセテート、ブチレングリコールモノイソブチルエーテルアセテート、ブチレングリコールモノ第三ブチルエーテルアセテート、アセト酢酸メチル、アセト酢酸エチル、オキソブタン酸メチル、オキソブタン酸エチル、γ−ラクトン、マロン酸ジメチル、コハク酸ジメチル、プロピレングリコールジアセテート、δ−ラクトン等が挙げられる。 Ester solvents include methyl formate, ethyl formate, methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, sec-butyl acetate, tributyl acetate, amyl acetate, isoamyl acetate, triamyl acetate, phenyl acetate , Methyl propionate, ethyl propionate, isopropyl propionate, butyl propionate, isobutyl propionate, sec-butyl propionate, tert-butyl propionate, amyl propionate, isoamyl propionate, tertiary amyl propionate, phenyl propionate , Methyl 2-ethylhexanoate, ethyl 2-ethylhexanoate, propyl 2-ethylhexanoate, isopropyl 2-ethylhexanoate, butyl 2-ethylhexanoate, methyl lactate, ethyl lactate, methyl methoxypropionate, ethoxypropyl Methyl pionate, ethyl methoxypropionate, ethyl ethoxypropionate, ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monopropyl ether acetate, ethylene glycol monoisopropyl ether acetate, ethylene glycol monobutyl ether Acetate, ethylene glycol mono sec-butyl ether acetate, ethylene glycol mono isobutyl ether acetate, ethylene glycol mono tert-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether Acetate, propylene glycol monoisopropyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol mono sec-butyl ether acetate, propylene glycol monoisobutyl ether acetate, propylene glycol mono-tert-butyl ether acetate, butylene glycol monomethyl ether acetate, butylene glycol monoethyl ether acetate Butylene glycol monopropyl ether acetate, Butylene glycol monoisopropyl ether acetate, Butylene glycol monobutyl ether acetate, Butylene glycol mono sec-butyl ether acetate, Butylene glycol monoisobutyl ether acetate, Butylene glycol mono-tert-butyl ether Examples include ether acetate, methyl acetoacetate, ethyl acetoacetate, methyl oxobutanoate, ethyl oxobutanoate, γ-lactone, dimethyl malonate, dimethyl succinate, propylene glycol diacetate, and δ-lactone.
エーテル系溶剤としては、テトラヒドロフラン、テトラヒドロピラン、モルホリン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、ジプロピレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、ジブチルエーテル、ジエチルエーテル、ジオキサン等が挙げられる。 Examples of the ether solvent include tetrahydrofuran, tetrahydropyran, morpholine, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, triethylene glycol dimethyl ether, dibutyl ether, diethyl ether, dioxane and the like.
脂肪族又は脂環族炭化水素系溶剤としては、ペンタン、ヘキサン、シクロヘキサン、メチルシクロヘキサン、ジメチルシクロヘキサン、エチルシクロヘキサン、ヘプタン、オクタン、デカリン、ソルベントナフサ、テレピン油、D−リモネン、ピネン、ミネラルスピリット、商品名「スワゾール#310」(コスモ松山石油社製)、商品名「ソルベッソ#100」(エクソン化学社製)等が挙げられる。 Aliphatic or alicyclic hydrocarbon solvents include pentane, hexane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane, heptane, octane, decalin, solvent naphtha, turpentine oil, D-limonene, pinene, mineral spirit, commodity The name “Swazol # 310” (manufactured by Cosmo Matsuyama Oil Co., Ltd.), the trade name “Sorvesso # 100” (manufactured by Exxon Chemical Co., Ltd.), and the like.
芳香族炭化水素系溶剤としては、ベンゼン、トルエン、エチルベンゼン、キシレン、メシチレン、ジエチルベンゼン、クメン、イソブチルベンゼン、シメン、テトラリンが挙げられる。 Examples of the aromatic hydrocarbon solvent include benzene, toluene, ethylbenzene, xylene, mesitylene, diethylbenzene, cumene, isobutylbenzene, cymene, and tetralin.
シアノ基を有する炭化水素溶剤としては、アセトニトリル、1−シアノプロパン、1−シアノブタン、1−シアノヘキサン、シアノシクロヘキサン、シアノベンゼン、1,3−ジシアノプロパン、1,4−ジシアノブタン、1,6−ジシアノヘキサン、1,4−ジシアノシクロヘキサン、1,4−ジシアノベンゼン等が挙げられる。 Examples of the hydrocarbon solvent having a cyano group include acetonitrile, 1-cyanopropane, 1-cyanobutane, 1-cyanohexane, cyanocyclohexane, cyanobenzene, 1,3-dicyanopropane, 1,4-dicyanobutane, 1,6- Examples include dicyanohexane, 1,4-dicyanocyclohexane, 1,4-dicyanobenzene and the like.
ハロゲン化芳香族炭化水素系溶媒としては、四塩化炭素、クロロホルム、トリクロロエチレン、塩化メチレン等が挙げられる。 Examples of the halogenated aromatic hydrocarbon solvent include carbon tetrachloride, chloroform, trichloroethylene, and methylene chloride.
その他の有機溶剤としては、N−メチル−2−ピロリドン、ジメチルスルホキシド、ジメチルホルムアミド、アニリン、トリエチルアミン、ピリジンが挙げられる。 Examples of other organic solvents include N-methyl-2-pyrrolidone, dimethyl sulfoxide, dimethylformamide, aniline, triethylamine, and pyridine.
本発明の担持体は、前述の本発明のシランカップリング剤組成物を担持したものである。シランカップリング剤組成物は、例えば、被担持体等に担持される。被担持体としては、例えば、アクリル樹脂、フッ素樹脂等の有機樹脂、炭化ケイ素、酸化チタン、酸化アルミニウム、酸化マグネシウム、酸化ジルコニウム、窒化アルミニウム等の金属酸化物、窒化ボロン、窒化ケイ素、酸化ケイ素、ゼオライト、活性炭等が挙げられる。シランカップリング剤組成物を被担持体に担持させる方法としては、公知の気層吸着、液層吸着等の方法を用いることができる。なお、液層吸着の例として、シランカップリング剤組成物を溶媒に溶解して得た溶液に被担持体を浸漬することで、被担持体にシランカップリング剤組成物を吸着させる方法が挙げられる。 The carrier of the present invention carries the above-described silane coupling agent composition of the present invention. The silane coupling agent composition is supported on, for example, a support. Examples of supported members include organic resins such as acrylic resins and fluororesins, metal oxides such as silicon carbide, titanium oxide, aluminum oxide, magnesium oxide, zirconium oxide, and aluminum nitride, boron nitride, silicon nitride, silicon oxide, Examples include zeolite and activated carbon. As a method for supporting the silane coupling agent composition on the support, a known method such as gas layer adsorption or liquid layer adsorption can be used. In addition, as an example of liquid layer adsorption, a method of adsorbing the silane coupling agent composition on the supported body by immersing the supported body in a solution obtained by dissolving the silane coupling agent composition in a solvent is given. It is done.
例えば、被担持体としての窒化アルミニウムフィラーにシランカップリング剤組成物を担持させて得た担持体をエポキシ樹脂中に分散させて樹脂組成物を得る。得られた樹脂組成物を硬化させれば、高い熱伝導性を有する熱伝導性硬化物を製造することができる。 For example, a support obtained by supporting a silane coupling agent composition on an aluminum nitride filler as a support is dispersed in an epoxy resin to obtain a resin composition. If the obtained resin composition is cured, a thermally conductive cured product having high thermal conductivity can be produced.
被担持体の形状は特に制限されず、例えば、膜状、粉状、粒状等の形状から、担持体の用途によって適宜選択すればよい。また、被担持体の大きさや、担持体に含有されるシランカップリング剤組成物の量についても特に制限されず、担持体の用途によって適宜選択すればよい。例えば、シート状の熱伝導性硬化物を得るために用いる樹脂組成物を製造する場合、被担持体の平均粒子径が1〜100μmであると、熱伝導性向上効果が高いために好ましい。なお、本明細書における「平均粒子径」とは、レーザー回折・散乱法によって求めた粒度分布における積算値50%での粒径を意味する。 The shape of the support is not particularly limited, and may be appropriately selected depending on the use of the support from, for example, a film shape, a powder shape, a granular shape, and the like. Further, the size of the support and the amount of the silane coupling agent composition contained in the support are not particularly limited, and may be appropriately selected depending on the use of the support. For example, in the case of producing a resin composition used for obtaining a sheet-like thermally conductive cured product, it is preferable that the average particle diameter of the supported body is 1 to 100 μm because the effect of improving thermal conductivity is high. The “average particle size” in the present specification means the particle size at an integrated value of 50% in the particle size distribution obtained by the laser diffraction / scattering method.
本発明の担持体は、熱伝導性硬化物を製造するための材料として用いられる樹脂組成物に配合されるほか、光電変換素子、触媒、及びトナー等にも用いることができる。 The carrier of the present invention can be used for a photoelectric conversion element, a catalyst, a toner, and the like in addition to being blended with a resin composition used as a material for producing a thermally conductive cured product.
以下、実施例及び比較例により本発明をさらに詳細に説明するが、本発明はこれらの実施例等によって何ら限定されるものではない。 Hereinafter, although an example and a comparative example explain the present invention still in detail, the present invention is not limited at all by these examples.
<ケイ素化合物の合成>
[実施例1]化合物No.19の合成
ビフェニル−4−カルボン酸(5.0mmol、1.0g、東京化成工業社製)、O−(ベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスファート(5.0mmol、1.9g)、及びジメチルホルムアミド(10.0ml)をフラスコに仕込み、40℃で0.5時間撹拌した。その後、N,N−ジイソプロピルエチルアミン(10.0mmol、1.3g)及び3−アミノプロピルトリエトキシシラン(5.0mmol、1.12g)を加えて、さらに2時間撹拌した。反応液に水(5ml)及びクロロホルム(5ml)を加え、油水分液を行った。得られた有機層をカラムクロマトグラフィー(移動相:ヘキサン/酢酸エチル=3/1(質量比))により精製することで、白色の固体1.49g(収率74%)を得た。得られた固体が化合物No.19であることを、UV−VIS(λmax)及び1H−NMR(重溶媒:CDCl3)を用いて確認した。収率及び外観観察結果を表1に示した。また、1H−NMRの結果を表2に示した。
<Synthesis of silicon compounds>
Example 1 Compound No. 1 Synthesis of 19 Biphenyl-4-carboxylic acid (5.0 mmol, 1.0 g, manufactured by Tokyo Chemical Industry Co., Ltd.), O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium Hexafluorophosphate (5.0 mmol, 1.9 g) and dimethylformamide (10.0 ml) were charged into a flask and stirred at 40 ° C. for 0.5 hour. Thereafter, N, N-diisopropylethylamine (10.0 mmol, 1.3 g) and 3-aminopropyltriethoxysilane (5.0 mmol, 1.12 g) were added, and the mixture was further stirred for 2 hours. Water (5 ml) and chloroform (5 ml) were added to the reaction solution, and an oil-water solution was performed. The obtained organic layer was purified by column chromatography (mobile phase: hexane / ethyl acetate = 3/1 (mass ratio)) to obtain 1.49 g (yield 74%) of a white solid. The resulting solid was identified as Compound No. 19 was confirmed using UV-VIS (λmax) and 1 H-NMR (deuterated solvent: CDCl 3 ). The yields and appearance observation results are shown in Table 1. The results of 1 H-NMR are shown in Table 2.
[実施例2〜9]化合物No.1、10、20、24、28、37、43及び46の合成
実施例1で用いたビフェニル−4−カルボン酸を、目的とする化合物に対応した構造を有するカルボン酸に変更したこと以外は、実施例1と同様の方法により化合物No.1、10、20、24、28、37、43及び46を合成した。合成した化合物が目的化合物であることをUV−VIS(λmax)及び1H−NMR(重溶媒:CDCl3)を用いて確認した。収率及び外観観察結果を表1に示した。また、1H−NMRの結果を表2に示した。
[Examples 2 to 9] Compound No. Synthesis of 1, 10, 20, 24, 28, 37, 43 and 46 Except that the biphenyl-4-carboxylic acid used in Example 1 was changed to a carboxylic acid having a structure corresponding to the target compound, Compound No. 1 was prepared in the same manner as in Example 1. 1, 10, 20, 24, 28, 37, 43 and 46 were synthesized. It was confirmed by UV-VIS (λmax) and 1 H-NMR (deuterated solvent: CDCl 3 ) that the synthesized compound was the target compound. The yields and appearance observation results are shown in Table 1. The results of 1 H-NMR are shown in Table 2.
[製造例1]化合物No.88の合成
目的化合物に対応した構造を有するカルボン酸化合物及びアミン化合物を用いたこと以外は、実施例1と同様の方法により化合物No.88を合成した。合成した化合物が目的化合物であることをUV−VIS(λmax)及び1H−NMR(重溶媒:CDCl3)を用いて確認した。収率及び外観観察結果を表1に示した。また、1H−NMRの結果を表2に示した。
[Production Example 1] Compound No. 1 Synthesis of Compound No. 88 Compound No. 88 was prepared in the same manner as in Example 1 except that a carboxylic acid compound and an amine compound having a structure corresponding to the target compound were used. 88 was synthesized. It was confirmed by UV-VIS (λmax) and 1 H-NMR (deuterated solvent: CDCl 3 ) that the synthesized compound was the target compound. The yields and appearance observation results are shown in Table 1. The results of 1 H-NMR are shown in Table 2.
<担持体の製造>
[実施例10]担持体No.1の製造
100mlのナスフラスコに窒化アルミニウムフィラー(トクヤマ社製、Hグレード、球状、粒径:1μm)10.0gを秤量し、ここに化合物No.19を50.0mg及びトルエン50mlを加え、超音波処理を30分行った。その後、50℃の真空加熱処理により溶媒を蒸発させた。さらに100℃の真空加熱処理を2時間行い、窒化アルミニウムフィラーの表面に化合物No.19を固定化させることで担持体No.1を得た。
<Manufacture of carrier>
[Example 10] Carrier No. Production of Compound No. 1 A 100 ml eggplant flask was weighed with 10.0 g of an aluminum nitride filler (T grade, H grade, spherical, particle size: 1 μm). 50.0 mg of 19 and 50 ml of toluene were added, and sonication was performed for 30 minutes. Thereafter, the solvent was evaporated by a vacuum heat treatment at 50 ° C. Further, a vacuum heat treatment at 100 ° C. was performed for 2 hours, and a compound no. The carrier No. 19 was fixed by immobilizing 19. 1 was obtained.
[実施例11〜18]担持体No.2〜9の製造
実施例10で用いた化合物No.19を、化合物No.1、10、20、24、28、37、43及び46にそれぞれ変更したこと以外は、実施例10と同様の方法により担持体No.2〜9を得た。
[Examples 11 to 18] Carrier No. Preparation of Nos. 2 to 9 Compound Nos. Used in Example 10 19 with compound no. The carrier No. 1 was changed in the same manner as in Example 10 except that the values were changed to 1, 10, 20, 24, 28, 37, 43 and 46, respectively. 2-9 were obtained.
[実施例19〜21]担持体No.10〜12の製造
実施例10で用いた窒化アルミニウムフィラーを、混合フィラー(窒化アルミニウムフィラー(トクヤマ社製、Hグレード、球状、粒径:1μm)0.83g、酸化アルミニウムフィラー(電気化学工業社製、DAW−20、球状、粒径:20μm)5.50g、酸化アルミニウムフィラー(電気化学工業社製、DAW−03、球状、粒径:3μm)1.38g、及び酸化アルミニウムフィラー(昭和電工社製、AL−47−1、破砕状、粒径:1μm)2.29g)に変更したこと、及び化合物No.19を化合物No.20、24及び43にそれぞれ変更したこと以外は、実施例10と同様の方法により担持体No.10〜12を得た。
[Examples 19 to 21] Carrier No. Production of Nos. 10 to 12 The aluminum nitride filler used in Example 10 was mixed with 0.83 g of a mixed filler (aluminum nitride filler (manufactured by Tokuyama, H grade, spherical, particle size: 1 μm), aluminum oxide filler (manufactured by Denki Kagaku Kogyo). DAW-20, spherical, particle size: 20 μm, 5.50 g, aluminum oxide filler (manufactured by Denki Kagaku Kogyo, DAW-03, spherical, particle size: 3 μm), 1.38 g, and aluminum oxide filler (manufactured by Showa Denko KK) , AL-47-1, crushed, particle size: 1 μm), changed to 2.29 g), and compound no. 19 is compound no. The carrier No. was changed in the same manner as in Example 10 except that the values were changed to 20, 24 and 43, respectively. 10-12 were obtained.
[製造例2]担持体No.13の製造
実施例10で用いた化合物No.19を化合物No.88に変更したこと以外は、実施例10と同様の方法により担持体No.13を得た。
[Production Example 2] Carrier No. Preparation of Compound No. 13 used in Example 10 19 is compound no. Except that the carrier No. 88 was changed, the carrier No. was obtained in the same manner as in Example 10. 13 was obtained.
[製造例3〜5]比較担持体1〜3の製造
実施例10で用いた化合物No.19を、以下に示す式(C−1)〜(C−3)で表される比較化合物1〜3にそれぞれ変更したこと以外は、実施例10と同様の方法により比
較担持体1〜3を得た。
[Production Examples 3 to 5] Production of Comparative Carriers 1 to 3 Compound No. 1 used in Example 10 was prepared. Comparative carriers 1 to 3 were prepared in the same manner as in Example 10 except that 19 was changed to Comparative compounds 1 to 3 represented by formulas (C-1) to (C-3) shown below. Obtained.
担持体No.1〜13及び比較担持体1〜3について、使用したフィラー及びケイ素化合物との対応表を表3に示す。 Carrier No. Table 3 shows the correspondence table between the fillers and silicon compounds used for 1 to 13 and comparative carriers 1 to 3.
<評価>
[評価例1]固定化量の確認
担持体No.1にトルエン50mlを加えて30分間撹拌した後、30分間静置し、固体を完全に沈降させることで分析用サンプル1を得た。分析用サンプル1の上澄み液を1ml分取し、トルエンで25倍に希釈することで分析用サンプル2を得た。分析用サンプル2をUV−VIS測定することで、分析用サンプル2中の化合物No.19のモル濃度を算出した。そして、下記計算式1より、担持体No.1に固定化されている化合物No.19の固定化量を算出した。その結果、担持体No.1は、窒化アルミニウムフィラー10gの表面に、化合物No.19が31.6mg(6.7×10-5mol)固定化されたものであることが分かった。
<Evaluation>
[Evaluation Example 1] Confirmation of immobilized amount 50 ml of toluene was added to 1 and stirred for 30 minutes, then allowed to stand for 30 minutes to completely settle the solid, thereby obtaining Sample 1 for analysis. An analytical sample 2 was obtained by taking 1 ml of the supernatant of the analytical sample 1 and diluting it 25 times with toluene. The sample No. 2 in the analytical sample 2 was measured by UV-VIS measurement of the analytical sample 2. A molar concentration of 19 was calculated. From the following calculation formula 1, the carrier No. Compound No. 1 immobilized to No. 1 19 immobilization amounts were calculated. As a result, the carrier No. 1 is compound No. 1 on the surface of 10 g of aluminum nitride filler. It was found that 19 was fixed to 31.6 mg (6.7 × 10 −5 mol).
計算式1:
S1=S2−(C×25×化合物No.19の分子量×L)
S1:担持体No.1に固定化されている化合物No.19の固定化量(g)
S2:担持体No.1を製造する際に使用した化合物No.19の量(g)
L:上澄み液の全容積(l)
C:分析用サンプル2中の化合物No.19のモル濃度(mol/l)
Formula 1:
S 1 = S 2 − (C × 25 × molecular weight of compound No. 19 × L)
S 1 : Carrier No. Compound No. 1 immobilized to No. 1 19 immobilized amount (g)
S 2 : Carrier No. Compound No. 1 used in producing No. 1 19 quantity (g)
L: Total volume of supernatant (l)
C: Compound No. in Sample 2 for analysis 19 molar concentration (mol / l)
<樹脂組成物の製造>
[実施例22〜34]樹脂組成物No.1〜13の製造
担持体No.1〜13(50g)に、ビフェニルアラルキル型エポキシ樹脂(商品名「NC−3000H」、日本化薬社製)7g及びビフェニルアラルキル型フェノール樹脂(商品名「MEH−7851H」、明和化成社製)3.5gをメチルエチルケトン10.5gに溶解した溶液、並びにイミダゾール系硬化剤(商品名「2PHZ−PW」、四国化成工業社製)0.1gを加え、3本ロールミルを使用して分散させることで、樹脂組成物No.1〜13を得た。
<Manufacture of resin composition>
[Examples 22 to 34] Resin composition No. Production of Nos. 1 to 13 1 to 13 (50 g), 7 g of biphenyl aralkyl type epoxy resin (trade name “NC-3000H”, manufactured by Nippon Kayaku Co., Ltd.) and biphenyl aralkyl type phenol resin (trade name “MEH-7851H”, manufactured by Meiwa Kasei Co., Ltd.) 3 By adding 0.1 g of a solution obtained by dissolving 0.5 g in 10.5 g of methyl ethyl ketone, and 0.1 g of an imidazole curing agent (trade name “2PHZ-PW”, manufactured by Shikoku Kasei Kogyo Co., Ltd.), using a three-roll mill, Resin composition No. 1-13 were obtained.
[製造例6〜10]比較樹脂組成物1〜5の製造
50gの(i)窒化アルミニウムフィラー(トクヤマ社製、Hグレード、球状、粒径:1μm)、(ii)混合フィラー(窒化アルミニウムフィラー(トクヤマ社製、Hグレード、球状、粒径:1μm)0.83g、酸化アルミニウムフィラー(電気化学工業社製、DAW−20、球状、粒径:20μm)5.50g、酸化アルミニウムフィラー(電気化学工業社製、DAW−03、球状、粒径:3μm)1.38g、及び酸化アルミニウムフィラー(昭和電工社製、AL−47−1、破砕状、粒径:1μm)2.29g)、又は(iii)比較担持体1〜3に、ビフェニルアラルキル型エポキシ樹脂(商品名「NC−3000H」、日本化薬社製)7g及びビフェニルアラルキル型フェノール樹脂(商品名「MEH−7851H」、明和化成社製)3.5gをメチルエチルケトン10.5gに溶解した溶液、並びにイミダゾール系硬化剤(商品名「2PHZ−PW」、四国化成工業社製)0.1gを加えた。そして、3本ロールミルを使用して分散させることで、比較樹脂組成物1〜5を得た。
[Production Examples 6 to 10] Production of Comparative Resin Compositions 1 to 50 50 g of (i) aluminum nitride filler (manufactured by Tokuyama, H grade, spherical, particle size: 1 μm), (ii) mixed filler (aluminum nitride filler ( Tokuyama, H grade, spherical, particle size: 1 μm 0.83 g, aluminum oxide filler (Denki Kagaku Kogyo, DAW-20, spherical, particle size: 20 μm) 5.50 g, aluminum oxide filler (electrochemical industry) DAW-03, spherical, particle size: 3 μm) 1.38 g, and aluminum oxide filler (Showa Denko, AL-47-1, crushed, particle size: 1 μm) 2.29 g), or (iii) ) 7 g of biphenyl aralkyl type epoxy resin (trade name “NC-3000H”, manufactured by Nippon Kayaku Co., Ltd.) and biphenyl aralkyl type phenol A solution prepared by dissolving 3.5 g of fat (trade name “MEH-7851H”, manufactured by Meiwa Kasei Co., Ltd.) in 10.5 g of methyl ethyl ketone, and an imidazole curing agent (trade name “2PHZ-PW”, manufactured by Shikoku Kasei Kogyo Co., Ltd.) 1 g was added. And comparative resin compositions 1-5 were obtained by making it disperse | distribute using a 3 roll mill.
樹脂組成物No.1〜13及び比較樹脂組成物1〜5について、使用した担持体との対応表を表4に示す。 Resin composition No. Table 4 shows a correspondence table with the used carriers for 1 to 13 and comparative resin compositions 1 to 5.
<熱伝導性シートの製造>
[実施例35〜47]硬化物No.1〜13の製造
樹脂組成物No.1〜13をバーコーター法によりPETフィルムに100μmの厚さで塗布し、100℃で10分間加熱することで乾燥させた。さらに、190℃で90分間加熱して硬化させた後、PETフィルムを剥離して、シート状の熱伝導性硬化物である硬化物No.1〜13を製造した。
<Manufacture of heat conductive sheet>
[Examples 35 to 47] Cured product No. Production of resin compositions No. 1-13 1 to 13 were applied to a PET film with a thickness of 100 μm by a bar coater method, and dried by heating at 100 ° C. for 10 minutes. Further, after being cured by heating at 190 ° C. for 90 minutes, the PET film was peeled off to obtain a cured product No. which is a sheet-like thermally conductive cured product. 1-13 were produced.
[製造例11〜15]比較硬化物1〜5の製造
比較樹脂組成物1〜5をバーコーター法によりPETフィルムに100μmの厚さで塗布し、100℃で10分間加熱することで乾燥させた。さらに、190℃で90分間加熱して硬化させた後、PETフィルムを剥離して、シート状の熱伝導性硬化物である比較硬化物1〜5を製造した。
[Production Examples 11 to 15] Production of Comparative Cured Products 1 to 5 Comparative resin compositions 1 to 5 were applied to a PET film with a thickness of 100 μm by the bar coater method and dried by heating at 100 ° C. for 10 minutes. . Further, after curing by heating at 190 ° C. for 90 minutes, the PET film was peeled off to produce comparative cured products 1 to 5 which are sheet-like thermally conductive cured products.
硬化物No.1〜13及び比較硬化物1〜5について、使用した樹脂組成物との対応表を表5に示す。 Hardened product No. Table 5 shows the correspondence table with the resin compositions used for 1 to 13 and comparative cured products 1 to 5.
<評価>
[評価例2]熱伝導性の評価
硬化物No.1〜13及び比較硬化物1〜5について、熱拡散率・熱伝導率測定装置(商品名「ai−Phase Mobile」、アイフェイズ社製)を使用、周期加熱法によって熱拡散率を測定した。結果を表6に示す。
<Evaluation>
[Evaluation Example 2] Evaluation of thermal conductivity About 1-13 and comparative hardened | cured material 1-5, the thermal diffusivity was measured by the period heating method using the thermal diffusivity and thermal conductivity measuring apparatus (Brand name "ai-Phase Mobile", the product made by an eye phase company). The results are shown in Table 6.
表6に示すように、硬化物No.1〜13の熱拡散率は、比較硬化物1〜5の熱拡散率と比較して、10〜38%程度向上していることが分かった。なかでも、硬化物No.1、4及び8は特に高い熱伝導性を示すことが分かった。以上より、本発明の樹脂組成物を用いて製造した硬化物は、高い熱伝導性を有する熱伝導性硬化物であることが分かった。 As shown in Table 6, the cured product No. It turned out that the thermal diffusivity of 1-13 is improving about 10-38% compared with the thermal diffusivity of the comparative hardened | cured materials 1-5. Among these, cured product No. 1, 4 and 8 were found to exhibit particularly high thermal conductivity. As mentioned above, it turned out that the hardened | cured material manufactured using the resin composition of this invention is a heat conductive hardened | cured material which has high heat conductivity.
Claims (5)
前記シランカップリング剤組成物が、下記一般式(1)で表されるケイ素化合物を含有する樹脂組成物。
(前記一般式(1)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A1は単結合又は炭素原子数1〜4のアルカンジイル基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す。Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Xが下記式(X−1)で表される基である場合のZは−NHCO−であり、Xが下記式(X−2)〜(X−6)のいずれかで表される基である場合のZは単結合又は−NHCO−である)
Containing a carrier carrying a silane coupling agent composition;
The resin composition in which the said silane coupling agent composition contains the silicon compound represented by following General formula (1).
(In the general formula (1), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, and A 1 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched oxyalkyl group having 1 to 12 carbon atoms, a dimethylamino group, a diethylamino group, or ethyl Represents a methylamino group, X represents a group represented by any one of the following formulas (X-1) to (X-6), and X represents a group represented by the following formula (X-1). Z is -NHCO-, and Z is a single bond or -NHCO- when X is a group represented by any one of the following formulas (X-2) to (X-6))
(前記一般式(2)中、R1は、それぞれ独立に炭素原子数1〜3の直鎖又は分岐状のアルキル基を表し、A2は炭素原子数1〜4のアルカンジイル基を表し、Xは下記式(X−1)〜(X−6)のいずれかで表される基を表し、Yは水素原子、炭素原子数1〜12の直鎖若しくは分岐状のアルキル基、炭素原子数1〜12の直鎖若しくは分岐状のオキシアルキル基、ジメチルアミノ基、ジエチルアミノ基、又はエチルメチルアミノ基を表す)
A silicon compound represented by the following general formula (2).
(In the general formula (2), each R 1 independently represents a linear or branched alkyl group having 1 to 3 carbon atoms, A 2 represents an alkanediyl group having 1 to 4 carbon atoms, X represents a group represented by any of the following formulas (X-1) to (X-6), Y represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or the number of carbon atoms. 1 to 12 linear or branched oxyalkyl group, dimethylamino group, diethylamino group, or ethylmethylamino group)
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CN201480066236.3A CN105793361A (en) | 2013-12-03 | 2014-11-27 | Resin composition, thermally-conductive cured product, silicon compound, silane coupling agent composition and carrier |
KR1020167017617A KR20160094407A (en) | 2013-12-03 | 2014-11-27 | Resin composition, thermally-conductive cured product, silicon compound, silane coupling agent composition and carrier |
PCT/JP2014/081436 WO2015083620A1 (en) | 2013-12-03 | 2014-11-27 | Resin composition, thermally-conductive cured product, silicon compound, silane coupling agent composition and carrier |
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WO2018037913A1 (en) * | 2016-08-22 | 2018-03-01 | 富士フイルム株式会社 | Light-shielding composition, light-shielding film, solid imaging element, color filter, and liquid-crystal display device |
US20220145125A1 (en) * | 2020-11-06 | 2022-05-12 | Tokyo Ohka Kogyo Co., Ltd. | Energy-sensitive composition, cured product, forming method of cured product, thermal base generator and compound |
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KR102052198B1 (en) * | 2016-12-22 | 2019-12-04 | 삼성에스디아이 주식회사 | Compound comprising amide bonding connected with cycle and alkoxysilan group, epoxy resin composition comprising the same and apparatus prepared using the same |
WO2019244531A1 (en) * | 2018-06-21 | 2019-12-26 | 株式会社Adeka | Method for producing surface-treated aluminum nitride, surface-treated aluminum nitride, resin composition and cured product |
EP3904481A4 (en) * | 2018-12-26 | 2022-09-28 | ENEOS Corporation | Silane compound and composition thereof |
CN114149616B (en) * | 2022-01-04 | 2023-11-28 | 全球能源互联网研究院有限公司 | Heat conducting filler, preparation method, resin composite material containing heat conducting filler and application of resin composite material |
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JP2007535532A (en) * | 2004-04-30 | 2007-12-06 | サイムダン コスメティック カンパニー リミテッド | Spherical particles of polysilsesquioxane having ultraviolet absorbing groups and method for producing the same |
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WO2018037913A1 (en) * | 2016-08-22 | 2018-03-01 | 富士フイルム株式会社 | Light-shielding composition, light-shielding film, solid imaging element, color filter, and liquid-crystal display device |
JPWO2018037913A1 (en) * | 2016-08-22 | 2019-06-20 | 富士フイルム株式会社 | Light-shielding composition, light-shielding film, solid-state imaging device, color filter, and liquid crystal display device |
US20220145125A1 (en) * | 2020-11-06 | 2022-05-12 | Tokyo Ohka Kogyo Co., Ltd. | Energy-sensitive composition, cured product, forming method of cured product, thermal base generator and compound |
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WO2015083620A1 (en) | 2015-06-11 |
CN105793361A (en) | 2016-07-20 |
JP6224444B2 (en) | 2017-11-01 |
KR20160094407A (en) | 2016-08-09 |
TW201529664A (en) | 2015-08-01 |
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