CN102206326B - 多元羟基树脂、环氧树脂、它们的制造法、使用了它们的环氧树脂组合物和固化物 - Google Patents
多元羟基树脂、环氧树脂、它们的制造法、使用了它们的环氧树脂组合物和固化物 Download PDFInfo
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- CN102206326B CN102206326B CN201110076251.4A CN201110076251A CN102206326B CN 102206326 B CN102206326 B CN 102206326B CN 201110076251 A CN201110076251 A CN 201110076251A CN 102206326 B CN102206326 B CN 102206326B
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- Prior art keywords
- resin
- epoxy resin
- hydroxy
- hydroxyl
- multielement
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- 229920005989 resin Polymers 0.000 title claims abstract description 112
- 239000011347 resin Substances 0.000 title claims abstract description 112
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 93
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 93
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 29
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 28
- 239000000155 melt Substances 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 238000000465 moulding Methods 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 238000005266 casting Methods 0.000 abstract description 4
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- 238000003475 lamination Methods 0.000 abstract 1
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- 239000011159 matrix material Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
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- 230000000052 comparative effect Effects 0.000 description 10
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- 239000003063 flame retardant Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
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- 239000000243 solution Substances 0.000 description 8
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
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- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 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
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- 239000000049 pigment Substances 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 239000003377 acid catalyst Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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- Engineering & Computer Science (AREA)
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JP5672947B2 (ja) * | 2010-10-25 | 2015-02-18 | 住友ベークライト株式会社 | 封止用樹脂組成物及び電子部品装置 |
MY169844A (en) * | 2012-02-23 | 2019-05-17 | Nippon Steel Chemical & Mat Co Ltd | Polyvalent hydroxy resin, epoxy resin, method for producing same, epoxy resin composition and cured product thereof |
CN103724998A (zh) * | 2013-05-30 | 2014-04-16 | 广东生益科技股份有限公司 | 一种氰酸酯树脂组合物及其用途 |
CN103724999A (zh) * | 2013-05-30 | 2014-04-16 | 广东生益科技股份有限公司 | 一种氰酸酯树脂组合物及其用途 |
KR101738291B1 (ko) * | 2013-05-30 | 2017-05-19 | 셍기 테크놀로지 코. 엘티디. | 시아네이트 수지 조성물 및 그 용도 |
JP6406847B2 (ja) * | 2014-03-26 | 2018-10-17 | 新日鉄住金化学株式会社 | 変性多価ヒドロキシ樹脂、エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
JP7277136B2 (ja) * | 2018-12-28 | 2023-05-18 | 日鉄ケミカル&マテリアル株式会社 | エポキシ樹脂、エポキシ樹脂組成物、及びその硬化物 |
CN113614140B (zh) * | 2019-03-27 | 2024-07-09 | 日铁化学材料株式会社 | 萘酚树脂、环氧树脂、环氧树脂组合物及其固化物 |
CN112920378B (zh) * | 2021-01-28 | 2023-06-13 | 深圳市宝安区新材料研究院 | 一种羟基树脂及其制备方法和应用 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07206984A (ja) * | 1994-01-11 | 1995-08-08 | Mitsui Toatsu Chem Inc | エポキシ樹脂組成物、その硬化物および半導体装置 |
JP2004059792A (ja) * | 2002-07-30 | 2004-02-26 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
JP2004123859A (ja) * | 2002-10-01 | 2004-04-22 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
CN1737055A (zh) * | 2004-08-19 | 2006-02-22 | 新日铁化学株式会社 | 环氧树脂组合物及其固化物 |
CN101027336A (zh) * | 2004-09-01 | 2007-08-29 | 大日本油墨化学工业株式会社 | 环氧树脂组合物、其固化物、半导体封装材料、新型酚醛树脂、新型环氧树脂、新型酚醛树脂的制造方法及新型环氧树脂的制造方法 |
JP2009001812A (ja) * | 2008-08-04 | 2009-01-08 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
CN101370870A (zh) * | 2006-01-23 | 2009-02-18 | 日立化成工业株式会社 | 封固用环氧树脂成形材料以及电子零件装置 |
CN101522792A (zh) * | 2006-10-02 | 2009-09-02 | 日立化成工业株式会社 | 密封用环氧树脂成形材料以及电子零件装置 |
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Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07206984A (ja) * | 1994-01-11 | 1995-08-08 | Mitsui Toatsu Chem Inc | エポキシ樹脂組成物、その硬化物および半導体装置 |
JP2004059792A (ja) * | 2002-07-30 | 2004-02-26 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
JP2004123859A (ja) * | 2002-10-01 | 2004-04-22 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
CN1737055A (zh) * | 2004-08-19 | 2006-02-22 | 新日铁化学株式会社 | 环氧树脂组合物及其固化物 |
CN101027336A (zh) * | 2004-09-01 | 2007-08-29 | 大日本油墨化学工业株式会社 | 环氧树脂组合物、其固化物、半导体封装材料、新型酚醛树脂、新型环氧树脂、新型酚醛树脂的制造方法及新型环氧树脂的制造方法 |
CN101370870A (zh) * | 2006-01-23 | 2009-02-18 | 日立化成工业株式会社 | 封固用环氧树脂成形材料以及电子零件装置 |
CN101522792A (zh) * | 2006-10-02 | 2009-09-02 | 日立化成工业株式会社 | 密封用环氧树脂成形材料以及电子零件装置 |
JP2009001812A (ja) * | 2008-08-04 | 2009-01-08 | Nippon Steel Chem Co Ltd | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造法、それらを用いたエポキシ樹脂組成物及び硬化物 |
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TWI561550B (ja) | 2016-12-11 |
JP2011207966A (ja) | 2011-10-20 |
TW201211097A (en) | 2012-03-16 |
JP5209660B2 (ja) | 2013-06-12 |
KR20110109939A (ko) | 2011-10-06 |
CN102206326A (zh) | 2011-10-05 |
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