TWI705982B - 硬化性樹脂及其製造方法 - Google Patents
硬化性樹脂及其製造方法 Download PDFInfo
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- TWI705982B TWI705982B TW105101655A TW105101655A TWI705982B TW I705982 B TWI705982 B TW I705982B TW 105101655 A TW105101655 A TW 105101655A TW 105101655 A TW105101655 A TW 105101655A TW I705982 B TWI705982 B TW I705982B
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- Prior art keywords
- curable resin
- epoxy resin
- mol
- epoxy
- phenol compound
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- -1 phenol compound Chemical class 0.000 claims abstract description 69
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1494—Polycondensates modified by chemical after-treatment followed by a further chemical treatment thereof
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
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- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1444—Monoalcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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Landscapes
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| CN108164686B (zh) * | 2018-02-01 | 2020-01-21 | 江南大学 | 一种改性环氧丙烯酸酯、含该改性环氧丙烯酸酯的阻焊剂 |
| KR102177966B1 (ko) * | 2019-03-07 | 2020-11-12 | 주식회사 케이씨씨 | 수용성 에폭시 수지 분산액 및 이의 제조방법 |
| JP7791997B2 (ja) * | 2022-07-06 | 2025-12-24 | 株式会社日本触媒 | 硬化性樹脂、並びに硬化性樹脂中間体、硬化性樹脂、硬化性樹脂組成物、及び硬化物の製造方法 |
| CN119842029A (zh) * | 2025-03-18 | 2025-04-18 | 洛阳昱胜化学有限公司 | 一种压裂用多元共聚稠化剂及其制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11288091A (ja) * | 1997-12-19 | 1999-10-19 | Taiyo Ink Mfg Ltd | アルカリ現像可能な光硬化性・熱硬化性組成物及びそれから得られる硬化皮膜 |
| US6077879A (en) * | 1997-11-11 | 2000-06-20 | Nippon Shokubai Co., Ltd. | Curable resin and resin composition |
| JP2007199246A (ja) * | 2006-01-25 | 2007-08-09 | Taiyo Ink Mfg Ltd | 硬化性組成物及びその硬化物 |
| CN102792224A (zh) * | 2010-03-08 | 2012-11-21 | 株式会社Lg化学 | 具有优良耐热性和机械性能的光敏树脂组合物及印刷电路板用保护膜 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8315230D0 (en) | 1983-06-03 | 1983-07-06 | Shell Int Research | Polyglycidyl ethers |
| EP0127915B1 (en) | 1983-06-03 | 1988-12-07 | Shell Internationale Researchmaatschappij B.V. | Novel polyglycidyl ethers, their preparation and their use as thermosetting coating compositions |
| GB8405139D0 (en) | 1984-02-28 | 1984-04-04 | Shell Int Research | Binders for thermosetting coating compositions |
| GB8329881D0 (en) | 1983-11-09 | 1983-12-14 | Shell Int Research | Preparation of binders for coatings |
| US4686248A (en) | 1984-02-28 | 1987-08-11 | Shell Oil Company | Preparation of binders for coatings, thermosetting coating compositions and their use |
| JPS61243869A (ja) | 1985-04-19 | 1986-10-30 | Taiyo Ink Seizo Kk | レジストインキ組成物 |
| JPS63258975A (ja) | 1986-12-26 | 1988-10-26 | Toshiba Corp | ソルダーレジストインキ組成物 |
| DE3704149A1 (de) | 1987-02-11 | 1988-08-25 | Ruetgerswerke Ag | Durch bestrahlung haertbare harze, verfahren zu ihrer herstellung und verwendung |
| JPH06192387A (ja) | 1992-12-24 | 1994-07-12 | Toagosei Chem Ind Co Ltd | 活性エネルギー線硬化性樹脂 |
| JP3395993B2 (ja) | 1994-03-08 | 2003-04-14 | 日本化薬株式会社 | 樹脂組成物、レジストインキ組成物及びその硬化物 |
| JP3409279B2 (ja) | 1997-11-11 | 2003-05-26 | 株式会社日本触媒 | 硬化性樹脂および樹脂組成物 |
| JP3541136B2 (ja) * | 1997-12-19 | 2004-07-07 | 太陽インキ製造株式会社 | アルカリ現像可能な光硬化性・熱硬化性組成物及びそれから得られる硬化皮膜 |
| JP3820406B2 (ja) * | 1997-12-19 | 2006-09-13 | 太陽インキ製造株式会社 | アルカリ現像可能な光硬化性・熱硬化性組成物及びそれから得られる硬化皮膜 |
| JP2000109541A (ja) | 1998-10-06 | 2000-04-18 | Nippon Poritekku Kk | 感光性熱硬化性樹脂組成物 |
| US7195857B2 (en) * | 2001-07-04 | 2007-03-27 | Showa Denko K.K. | Resist curable resin composition and cured article thereof |
| JP3953852B2 (ja) * | 2002-03-22 | 2007-08-08 | 太陽インキ製造株式会社 | 光硬化性・熱硬化性樹脂組成物 |
| JP4175837B2 (ja) * | 2002-07-02 | 2008-11-05 | 株式会社日本触媒 | 画像形成用感光性樹脂組成物 |
| JP2004061566A (ja) * | 2002-07-25 | 2004-02-26 | Taiyo Ink Mfg Ltd | 光硬化性・熱硬化性樹脂組成物及びそれを用いて得られるプリント配線板 |
| JP4186737B2 (ja) * | 2003-07-17 | 2008-11-26 | Ｊｓｒ株式会社 | 低弾性率熱硬化性樹脂組成物および該組成物を用いた熱硬化性フィルム、ならびにそれらの硬化物 |
| KR20070085911A (ko) * | 2004-11-10 | 2007-08-27 | 제이에스알 가부시끼가이샤 | 열경화성 수지 조성물, 열경화성 필름 및 이들의 경화물,및 전자 부품 |
| TW200710572A (en) * | 2005-05-31 | 2007-03-16 | Taiyo Ink Mfg Co Ltd | Photocuring/thermosetting resin composition, curing/setting product thereof and printed wiring board obtained using the same |
| WO2007119651A1 (ja) * | 2006-04-13 | 2007-10-25 | Taiyo Ink Mfg. Co., Ltd. | アルカリ現像型ソルダーレジスト及びその硬化物並びにそれを用いて得られるプリント配線板 |
| CN101105626A (zh) * | 2006-07-10 | 2008-01-16 | 太阳油墨制造株式会社 | 光固化性·热固化性树脂组合物、其固化物及印刷电路板 |
| JP4873238B2 (ja) * | 2006-08-31 | 2012-02-08 | Ｄｉｃ株式会社 | アルカリ現像型感光性樹脂組成物、レジストインキ、及びプリント配線基板 |
| WO2008059670A1 (en) * | 2006-11-15 | 2008-05-22 | Taiyo Ink Mfg. Co., Ltd. | Photocurable/thermosetting resin composition, cured object, and printed wiring board |
| JP4774070B2 (ja) * | 2007-03-05 | 2011-09-14 | 株式会社日本触媒 | 画像形成用感光性樹脂組成物及びその製造方法 |
| CN101542392B (zh) * | 2007-03-29 | 2013-08-14 | 太阳控股株式会社 | 光固化性树脂组合物、干膜、固化物以及印刷线路板 |
| JP5661293B2 (ja) | 2010-02-08 | 2015-01-28 | 太陽ホールディングス株式会社 | 光硬化性樹脂組成物、ドライフィルム、硬化物及びプリント配線板 |
| CN103492950B (zh) * | 2011-06-17 | 2016-04-13 | 太阳油墨制造株式会社 | 光固化性热固化性树脂组合物 |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6077879A (en) * | 1997-11-11 | 2000-06-20 | Nippon Shokubai Co., Ltd. | Curable resin and resin composition |
| JPH11288091A (ja) * | 1997-12-19 | 1999-10-19 | Taiyo Ink Mfg Ltd | アルカリ現像可能な光硬化性・熱硬化性組成物及びそれから得られる硬化皮膜 |
| JP2007199246A (ja) * | 2006-01-25 | 2007-08-09 | Taiyo Ink Mfg Ltd | 硬化性組成物及びその硬化物 |
| CN102792224A (zh) * | 2010-03-08 | 2012-11-21 | 株式会社Lg化学 | 具有优良耐热性和机械性能的光敏树脂组合物及印刷电路板用保护膜 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105837795A (zh) | 2016-08-10 |
| KR101952927B1 (ko) | 2019-02-27 |
| TW201629115A (zh) | 2016-08-16 |
| JP6557155B2 (ja) | 2019-08-07 |
| JP2016145334A (ja) | 2016-08-12 |
| US10508169B2 (en) | 2019-12-17 |
| US20160222154A1 (en) | 2016-08-04 |
| KR20160094862A (ko) | 2016-08-10 |
| JP2019151861A (ja) | 2019-09-12 |
| JP6691627B2 (ja) | 2020-04-28 |
| CN105837795B (zh) | 2019-06-14 |
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