TWI382999B - 可固化黏著劑組成物、方法、及應用 - Google Patents
可固化黏著劑組成物、方法、及應用 Download PDFInfo
- Publication number
- TWI382999B TWI382999B TW098100768A TW98100768A TWI382999B TW I382999 B TWI382999 B TW I382999B TW 098100768 A TW098100768 A TW 098100768A TW 98100768 A TW98100768 A TW 98100768A TW I382999 B TWI382999 B TW I382999B
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- Taiwan
- Prior art keywords
- composition
- cured
- benzo
- uncured
- phenolic compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 126
- 239000000853 adhesive Substances 0.000 title claims description 40
- 230000001070 adhesive effect Effects 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 25
- 230000008569 process Effects 0.000 title description 3
- 150000002989 phenols Chemical class 0.000 claims description 58
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 41
- 125000005605 benzo group Chemical group 0.000 claims description 40
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 34
- 239000003822 epoxy resin Substances 0.000 claims description 34
- 229920000647 polyepoxide Polymers 0.000 claims description 34
- -1 aryl carbonate glycidyl esters Chemical class 0.000 claims description 31
- 239000012351 deprotecting agent Substances 0.000 claims description 19
- OZCWUNHGNVXCCO-UHFFFAOYSA-N oxiran-2-ylmethyl hydrogen carbonate Chemical group OC(=O)OCC1CO1 OZCWUNHGNVXCCO-UHFFFAOYSA-N 0.000 claims description 13
- 235000013824 polyphenols Nutrition 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 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 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 8
- 239000007822 coupling agent Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
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- 229910000679 solder Inorganic materials 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
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- 239000004615 ingredient Substances 0.000 claims description 3
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- 239000005711 Benzoic acid Substances 0.000 claims description 2
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- 238000009472 formulation Methods 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims 6
- 229920003986 novolac Polymers 0.000 claims 3
- 229920000767 polyaniline Polymers 0.000 claims 3
- 239000008393 encapsulating agent Substances 0.000 claims 2
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- 150000002924 oxiranes Chemical class 0.000 claims 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 6
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 125000003636 chemical group Chemical group 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
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- IAIAQQLZYGPOKI-UHFFFAOYSA-N oxiran-2-ylmethoxycarbonyl oxiran-2-ylmethyl carbonate Chemical compound C1OC1COC(=O)OC(=O)OCC1CO1 IAIAQQLZYGPOKI-UHFFFAOYSA-N 0.000 description 3
- CUWYXAQEXAAJJI-UHFFFAOYSA-N oxiran-2-ylmethyl carbonochloridate Chemical compound ClC(=O)OCC1CO1 CUWYXAQEXAAJJI-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
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- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
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- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012722 thermally initiated polymerization Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- C08G59/20—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 characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- 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
- C08G59/20—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 characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/008,375 US8084553B2 (en) | 2008-01-10 | 2008-01-10 | Curable adhesive compositions, process, and applications |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200936629A TW200936629A (en) | 2009-09-01 |
| TWI382999B true TWI382999B (zh) | 2013-01-21 |
Family
ID=40850866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098100768A TWI382999B (zh) | 2008-01-10 | 2009-01-09 | 可固化黏著劑組成物、方法、及應用 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8084553B2 (enExample) |
| JP (1) | JP5661472B2 (enExample) |
| KR (1) | KR101288321B1 (enExample) |
| CN (1) | CN101970224B (enExample) |
| TW (1) | TWI382999B (enExample) |
| WO (1) | WO2009089314A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8802214B2 (en) * | 2005-06-13 | 2014-08-12 | Trillion Science, Inc. | Non-random array anisotropic conductive film (ACF) and manufacturing processes |
| US8067484B2 (en) * | 2010-03-12 | 2011-11-29 | Trillion Science, Inc. | Latent hardener with improved barrier properties and compatibility |
| US8044154B2 (en) * | 2009-06-12 | 2011-10-25 | Trillion Science, Inc. | Latent hardener for epoxy compositions |
| JP5698940B2 (ja) * | 2010-09-08 | 2015-04-08 | 積水化学工業株式会社 | 電子部品用接着剤及び半導体装置の製造方法 |
| JP6109144B2 (ja) * | 2011-03-28 | 2017-04-05 | スリーエム イノベイティブ プロパティズ カンパニー | 硬化性組成物、物品、硬化方法及びタックフリー反応生成物 |
| US9475963B2 (en) | 2011-09-15 | 2016-10-25 | Trillion Science, Inc. | Fixed array ACFs with multi-tier partially embedded particle morphology and their manufacturing processes |
| US9102851B2 (en) | 2011-09-15 | 2015-08-11 | Trillion Science, Inc. | Microcavity carrier belt and method of manufacture |
| JP2013253195A (ja) * | 2012-06-08 | 2013-12-19 | Namics Corp | エポキシ樹脂組成物 |
| US9352539B2 (en) | 2013-03-12 | 2016-05-31 | Trillion Science, Inc. | Microcavity carrier with image enhancement for laser ablation |
| GB201319363D0 (en) | 2013-11-01 | 2013-12-18 | Uni I Oslo | Compounds |
| US9540539B2 (en) * | 2014-05-27 | 2017-01-10 | Infineon Technologies Ag | Primer composition, method of forming a primer layer on a semiconductor device, and method of encapsulating a semiconductor device |
| KR20170033886A (ko) | 2014-07-22 | 2017-03-27 | 사빅 글로벌 테크놀러지스 비.브이. | 고온 모노머 및 이들의 용도의 방법 |
| CN104312471A (zh) * | 2014-11-10 | 2015-01-28 | 深圳市飞世尔实业有限公司 | 一种含苯并恶嗪的异方性导电膜及其制备方法 |
| BR112017018698A2 (pt) * | 2015-03-04 | 2018-04-17 | Huntsman Advanced Mat Americas Llc | ?composição livre de ácido de enxofre orgânico, artigo curado, uso de uma composição livre de ácido de enxofre orgânico, e, método para produzir um artigo compósito?. |
| CN108047647B (zh) * | 2017-12-27 | 2020-07-07 | 广东生益科技股份有限公司 | 一种无卤热固性树脂组合物及使用它的预浸料、层压板、覆金属箔层压板和印刷电路板 |
| JP7261654B2 (ja) * | 2018-05-24 | 2023-04-20 | 住友化学株式会社 | 化合物、樹脂、レジスト組成物及びレジストパターンの製造方法 |
| KR102633142B1 (ko) | 2019-08-26 | 2024-02-02 | 삼성전자주식회사 | 반도체 패키지 |
| EP4026630A4 (en) * | 2019-09-02 | 2023-08-23 | Osaka Soda Co., Ltd. | Silver particles |
| CN117534682A (zh) * | 2023-11-09 | 2024-02-09 | 江苏大学 | 一种具有多苯并二噁茂结构的单官能度生物基苯并噁嗪单体及树脂 |
| CN119552132A (zh) * | 2024-11-04 | 2025-03-04 | 北玻院(滕州)复合材料有限公司 | 一种可降解环氧树脂单体、环氧树脂、复合材料及其制备方法和降解方法 |
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| US5409764A (en) * | 1990-07-17 | 1995-04-25 | Toyo Ink Manufacturing Co., Ltd. | Curable adhesive composition and sheet thereof |
| US20020082322A1 (en) * | 2000-09-21 | 2002-06-27 | Kuen-Yuan Hwang | Flame retarded epoxy resin composition |
| US20020128354A1 (en) * | 2001-01-05 | 2002-09-12 | Garrett David William | Novel hardener for epoxy molding compounds |
| US20040006150A1 (en) * | 2002-06-24 | 2004-01-08 | Henkel Loctite Corporation | Photocurable adhesive compositions, reaction products of which have low halide ion content |
| US20040147640A1 (en) * | 2003-01-16 | 2004-07-29 | Kuen-Yuan Hwang | Halogen-free resin composition |
| US20070149726A1 (en) * | 2004-07-13 | 2007-06-28 | Yukio Isobe | Curable compositions having improved adhesion performance |
| TWI294434B (en) * | 2003-10-10 | 2008-03-11 | Asahi Kasei Chemicals Corp | Latent curing agent and composition containing the same |
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-
2008
- 2008-01-10 US US12/008,375 patent/US8084553B2/en not_active Expired - Fee Related
-
2009
- 2009-01-08 KR KR1020107015116A patent/KR101288321B1/ko not_active Expired - Fee Related
- 2009-01-08 CN CN200980102010.3A patent/CN101970224B/zh not_active Expired - Fee Related
- 2009-01-08 JP JP2010542331A patent/JP5661472B2/ja not_active Expired - Fee Related
- 2009-01-08 WO PCT/US2009/030384 patent/WO2009089314A1/en not_active Ceased
- 2009-01-09 TW TW098100768A patent/TWI382999B/zh not_active IP Right Cessation
-
2011
- 2011-10-06 US US13/267,052 patent/US20120029116A1/en not_active Abandoned
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| US5409764A (en) * | 1990-07-17 | 1995-04-25 | Toyo Ink Manufacturing Co., Ltd. | Curable adhesive composition and sheet thereof |
| US20020082322A1 (en) * | 2000-09-21 | 2002-06-27 | Kuen-Yuan Hwang | Flame retarded epoxy resin composition |
| US20020128354A1 (en) * | 2001-01-05 | 2002-09-12 | Garrett David William | Novel hardener for epoxy molding compounds |
| US20040006150A1 (en) * | 2002-06-24 | 2004-01-08 | Henkel Loctite Corporation | Photocurable adhesive compositions, reaction products of which have low halide ion content |
| US20040147640A1 (en) * | 2003-01-16 | 2004-07-29 | Kuen-Yuan Hwang | Halogen-free resin composition |
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| US20070149726A1 (en) * | 2004-07-13 | 2007-06-28 | Yukio Isobe | Curable compositions having improved adhesion performance |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20100124704A (ko) | 2010-11-29 |
| US20120029116A1 (en) | 2012-02-02 |
| CN101970224B (zh) | 2014-11-12 |
| US8084553B2 (en) | 2011-12-27 |
| TW200936629A (en) | 2009-09-01 |
| CN101970224A (zh) | 2011-02-09 |
| JP5661472B2 (ja) | 2015-01-28 |
| HK1152681A1 (en) | 2012-03-09 |
| KR101288321B1 (ko) | 2013-07-23 |
| US20090181165A1 (en) | 2009-07-16 |
| WO2009089314A1 (en) | 2009-07-16 |
| JP2011509340A (ja) | 2011-03-24 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |