JP4058540B2 - エポキシ樹脂用接着促進剤として有用なノボラック化合物 - Google Patents
エポキシ樹脂用接着促進剤として有用なノボラック化合物 Download PDFInfo
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- JP4058540B2 JP4058540B2 JP50323698A JP50323698A JP4058540B2 JP 4058540 B2 JP4058540 B2 JP 4058540B2 JP 50323698 A JP50323698 A JP 50323698A JP 50323698 A JP50323698 A JP 50323698A JP 4058540 B2 JP4058540 B2 JP 4058540B2
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- alkaryl
- alkyl
- alkoxy
- aryl
- Prior art date
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- 239000002318 adhesion promoter Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 30
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- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
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- 150000008064 anhydrides Chemical class 0.000 description 2
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
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- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
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- 239000010941 cobalt Substances 0.000 description 1
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
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- 230000007547 defect Effects 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HFLGBNBLMBSXEM-UHFFFAOYSA-N ethyl catechol Natural products CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
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- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
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- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
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- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical group [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/668,176 US5859153A (en) | 1996-06-21 | 1996-06-21 | Novolak compounds useful as adhesion promoters for epoxy resins |
| US08/668,176 | 1996-06-21 | ||
| PCT/US1997/010472 WO1997048746A1 (en) | 1996-06-21 | 1997-06-17 | Novolak compounds useful as adhesion promoters for epoxy resins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2000514107A JP2000514107A (ja) | 2000-10-24 |
| JP2000514107A5 JP2000514107A5 (enExample) | 2005-02-10 |
| JP4058540B2 true JP4058540B2 (ja) | 2008-03-12 |
Family
ID=24681307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50323698A Expired - Fee Related JP4058540B2 (ja) | 1996-06-21 | 1997-06-17 | エポキシ樹脂用接着促進剤として有用なノボラック化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5859153A (enExample) |
| EP (1) | EP0906352B1 (enExample) |
| JP (1) | JP4058540B2 (enExample) |
| AU (1) | AU3490697A (enExample) |
| DE (1) | DE69702910T2 (enExample) |
| WO (1) | WO1997048746A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5885172A (en) * | 1997-05-27 | 1999-03-23 | Acushnet Company | Multilayer golf ball with a thin thermoset outer layer |
| US6210294B1 (en) * | 1999-05-14 | 2001-04-03 | Acushnet Company | Polyurethane golf ball with improved resiliency |
| US7015300B2 (en) * | 1995-06-07 | 2006-03-21 | Acushnet Company | Multilayered golf ball and composition |
| US6486261B1 (en) * | 1998-12-24 | 2002-11-26 | Acushnet Company | Thin-layer-covered golf ball with improved velocity |
| US6913547B2 (en) | 1997-05-27 | 2005-07-05 | Acushnet Company | Thin-layer-covered multilayer golf ball |
| US6849006B2 (en) | 1997-05-27 | 2005-02-01 | Acushnet Company | Thin, thermoset, polyurethane-covered golf ball with a dual core |
| US6634964B2 (en) | 1997-05-27 | 2003-10-21 | Acushnet Company | Initial velocity dual core golf ball |
| US20050070377A1 (en) * | 1997-05-27 | 2005-03-31 | Christopher Cavallaro | Thin-layer-covered multilayer golf ball |
| US6998445B2 (en) * | 1998-03-26 | 2006-02-14 | Acushnet Company | Low compression, resilient golf balls with rubber core |
| EP1108734B1 (en) * | 1999-12-16 | 2011-03-09 | Sumitomo Bakelite Company Limited | Process for producing phenol resin |
| US20030165669A1 (en) * | 2002-03-04 | 2003-09-04 | Nowak David H. | Precure consolidator |
| US7094843B2 (en) * | 2002-08-19 | 2006-08-22 | 3M Innovative Properties Company | Epoxy compositions having improved shelf life and articles containing the same |
| TWI318220B (en) * | 2002-08-30 | 2009-12-11 | Asahi Organic Chem Ind | Manufacturing method of phenolic novolac |
| US6911512B2 (en) * | 2003-10-10 | 2005-06-28 | 3M Innovative Properties Company | Powder coating fluoropolymer compositions with aromatic materials |
| JP4727958B2 (ja) * | 2004-08-19 | 2011-07-20 | 旭有機材工業株式会社 | ノボラック型フェノール樹脂の製造方法 |
| US7670683B2 (en) * | 2005-12-22 | 2010-03-02 | 3M Innovative Properties Company | Damage-resistant epoxy compound |
| WO2007126970A2 (en) * | 2006-03-29 | 2007-11-08 | Borgwarner Inc. | Friction materials made with resins containing polar functional groups |
| EP2379280A1 (en) | 2008-12-31 | 2011-10-26 | 3M Innovative Properties Company | Coated carrier for lapping and methods of making and using |
| EP2398863B1 (en) * | 2009-02-19 | 2013-05-01 | 3M Innovative Properties Company | Fusion bonded epoxy coating compositions that include magnesium oxide |
| JP5774021B2 (ja) * | 2010-10-26 | 2015-09-02 | 明和化成株式会社 | フェノール系オリゴマー及びその製造方法 |
| CN104114617A (zh) * | 2011-08-19 | 2014-10-22 | 巴斯夫欧洲公司 | 线型酚醛基C-Sn材料、其制备方法及其在电化学电池中的用途 |
| EP2812390B1 (en) | 2012-02-10 | 2016-04-06 | 3M Innovative Properties Company | Anticorrosion coatings |
| JP5928703B2 (ja) * | 2012-03-30 | 2016-06-01 | 明和化成株式会社 | ノボラック型フェノール樹脂の製造方法、エポキシ樹脂組成物の製造方法 |
| WO2014186151A1 (en) | 2013-05-14 | 2014-11-20 | 3M Innovative Properties Company | Epoxy resins comprising a pyrazine-containing compound |
| US9169393B2 (en) | 2013-07-25 | 2015-10-27 | 3M Innovative Properties Company | Anticorrosion coatings |
| JP5983590B2 (ja) * | 2013-12-13 | 2016-08-31 | 株式会社デンソー | 硬化性樹脂組成物、封止材、及びこれを用いた電子デバイス製品 |
| CN109642001B (zh) | 2016-08-31 | 2022-04-01 | 3M创新有限公司 | 卤素和多卤化物介导的酚醛树脂聚合反应 |
| JP7632942B2 (ja) * | 2020-04-24 | 2025-02-19 | エルジー・ケム・リミテッド | 硬化剤、これを含む半導体接着用組成物、半導体接着用フィルムおよびこれを用いた半導体パッケージ |
| CN117255814A (zh) * | 2020-09-26 | 2023-12-19 | 米塞尔聚合物公司 | 含儿茶酚的薄膜材料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3304276A (en) * | 1964-05-13 | 1967-02-14 | Faulkner Raymond Noel | Polyhydric phenol modified fatty media and iron surfaces chelated therewith |
| US4200712A (en) * | 1978-10-23 | 1980-04-29 | The B. F. Goodrich Company | Coating polymerization reactors with oligomer coatings derived from reaction products of substituted phenols |
| JPS5710651A (en) * | 1980-06-23 | 1982-01-20 | Asahi Denka Kogyo Kk | Coating material composition |
| US4560732A (en) * | 1983-11-11 | 1985-12-24 | Asahi Denka Kogyo K.K. | Coating composition |
| US4530947A (en) * | 1984-04-24 | 1985-07-23 | Asahi Denka Kogyo K.K. | Anticorrosive coating composition |
| US5128230A (en) * | 1986-12-23 | 1992-07-07 | Shipley Company Inc. | Quinone diazide containing photoresist composition utilizing mixed solvent of ethyl lactate, anisole and amyl acetate |
| US5013791A (en) * | 1987-12-30 | 1991-05-07 | Ppg Industries, Inc. | Beta-hydroxyalkylamide cured acid polymer/polyepoxide powder coating |
| AU615744B2 (en) * | 1988-05-12 | 1991-10-10 | Minnesota Mining And Manufacturing Company | Powdered epoxy resin compositions |
| US5178986A (en) * | 1988-10-17 | 1993-01-12 | Shipley Company Inc. | Positive photoresist composition with naphthoquinonediazidesulfonate of oligomeric phenol |
| JPH0739445B2 (ja) * | 1988-12-07 | 1995-05-01 | 信越化学工業株式会社 | 重合体スケールの付着防止方法 |
| AU6140790A (en) * | 1989-09-07 | 1991-04-08 | Ocg Microelectronic Materials, Inc. | Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions |
| EP0675912A1 (en) * | 1992-12-22 | 1995-10-11 | Minnesota Mining And Manufacturing Company | Rapid cure thermosetting functional powder coatings |
| JP3428699B2 (ja) * | 1993-09-24 | 2003-07-22 | ジャパンエポキシレジン株式会社 | エポキシ樹脂組成物 |
-
1996
- 1996-06-21 US US08/668,176 patent/US5859153A/en not_active Expired - Lifetime
-
1997
- 1997-06-17 EP EP97931214A patent/EP0906352B1/en not_active Expired - Lifetime
- 1997-06-17 DE DE69702910T patent/DE69702910T2/de not_active Expired - Lifetime
- 1997-06-17 WO PCT/US1997/010472 patent/WO1997048746A1/en not_active Ceased
- 1997-06-17 JP JP50323698A patent/JP4058540B2/ja not_active Expired - Fee Related
- 1997-06-17 AU AU34906/97A patent/AU3490697A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000514107A (ja) | 2000-10-24 |
| EP0906352B1 (en) | 2000-08-23 |
| US5859153A (en) | 1999-01-12 |
| DE69702910D1 (de) | 2000-09-28 |
| WO1997048746A1 (en) | 1997-12-24 |
| DE69702910T2 (de) | 2001-03-29 |
| EP0906352A1 (en) | 1999-04-07 |
| AU3490697A (en) | 1998-01-07 |
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