TWI234577B - Adhesion promoter and self-priming resin compositions and articles made therefrom - Google Patents
Adhesion promoter and self-priming resin compositions and articles made therefrom Download PDFInfo
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- TWI234577B TWI234577B TW088114471A TW88114471A TWI234577B TW I234577 B TWI234577 B TW I234577B TW 088114471 A TW088114471 A TW 088114471A TW 88114471 A TW88114471 A TW 88114471A TW I234577 B TWI234577 B TW I234577B
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- 239000002318 adhesion promoter Substances 0.000 title description 9
- 239000011342 resin composition Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229920000642 polymer Polymers 0.000 claims abstract description 40
- 239000000463 material Substances 0.000 claims abstract description 39
- 238000000576 coating method Methods 0.000 claims abstract description 32
- 239000011248 coating agent Substances 0.000 claims abstract description 28
- 229910000077 silane Inorganic materials 0.000 claims abstract description 20
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000011347 resin Substances 0.000 claims abstract description 19
- 229920005989 resin Polymers 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 229920006037 cross link polymer Polymers 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 229920000412 polyarylene Polymers 0.000 claims abstract description 9
- 239000000919 ceramic Substances 0.000 claims abstract description 7
- -1 fluorenyl oxygen Chemical compound 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 150000004756 silanes Chemical class 0.000 claims description 6
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- JEOAUTNZTUGROC-UHFFFAOYSA-N 3-[4-[4-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)phenoxy]phenyl]-2,4,5-triphenylcyclopenta-2,4-dien-1-one Chemical compound O=C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC(OC=3C=CC(=CC=3)C=3C(=C(C(=O)C=3C=3C=CC=CC=3)C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)=C1C1=CC=CC=C1 JEOAUTNZTUGROC-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- YUOGUVUAZGQYFR-UHFFFAOYSA-N 1,3,5-tris(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC1=CC(C#CC=2C=CC=CC=2)=CC(C#CC=2C=CC=CC=2)=C1 YUOGUVUAZGQYFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052778 Plutonium Inorganic materials 0.000 claims 1
- OFPZFTWBJUGNGE-UHFFFAOYSA-N cyclopenta-1,3-dien-1-ylbenzene Chemical compound C1C=CC=C1C1=CC=CC=C1 OFPZFTWBJUGNGE-UHFFFAOYSA-N 0.000 claims 1
- OQLKNTOKMBVBKV-UHFFFAOYSA-N hexamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCCOC1=CC=C(C(N)=N)C=C1 OQLKNTOKMBVBKV-UHFFFAOYSA-N 0.000 claims 1
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- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 125000003118 aryl group Chemical group 0.000 description 20
- 239000008199 coating composition Substances 0.000 description 19
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- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 14
- 238000000034 method Methods 0.000 description 13
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- 239000002585 base Substances 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
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- FQQOMPOPYZIROF-UHFFFAOYSA-N cyclopenta-2,4-dien-1-one Chemical compound O=C1C=CC=C1 FQQOMPOPYZIROF-UHFFFAOYSA-N 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- CQDFTDKTCBPRCW-UHFFFAOYSA-N 826-65-3 Chemical compound C1=CC2C3C(=O)C=CC3C1C2=O CQDFTDKTCBPRCW-UHFFFAOYSA-N 0.000 description 3
- 238000005698 Diels-Alder reaction Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000000399 optical microscopy Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical compound CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052611 pyroxene Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000005477 sputtering target Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- AKJVMGQSGCSQBU-UHFFFAOYSA-N zinc azanidylidenezinc Chemical compound [Zn++].[N-]=[Zn].[N-]=[Zn] AKJVMGQSGCSQBU-UHFFFAOYSA-N 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
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
-
- 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
- C09D165/00—Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Coating compositions based on derivatives of such polymers
- C09D165/02—Polyphenylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/126—Polyphenylene oxides modified by chemical after-treatment
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/138,510 US6184284B1 (en) | 1998-08-24 | 1998-08-24 | Adhesion promoter and self-priming resin compositions and articles made therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI234577B true TWI234577B (en) | 2005-06-21 |
Family
ID=22482345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088114471A TWI234577B (en) | 1998-08-24 | 1999-08-24 | Adhesion promoter and self-priming resin compositions and articles made therefrom |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6184284B1 (enExample) |
| EP (1) | EP1112329B2 (enExample) |
| JP (1) | JP4343443B2 (enExample) |
| KR (1) | KR100604629B1 (enExample) |
| CN (1) | CN1210362C (enExample) |
| DE (1) | DE69918316T3 (enExample) |
| TW (1) | TWI234577B (enExample) |
| WO (1) | WO2000011096A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI646145B (zh) * | 2015-04-06 | 2019-01-01 | 美商羅門哈斯電子材料有限公司 | 聚伸芳基聚合物 |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534546A (ja) | 1999-01-08 | 2002-10-15 | ザ ダウ ケミカル カンパニー | 良好な接着性および靭性を有する低誘電率ポリマーおよび該ポリマーから作製された物品 |
| US7115531B2 (en) | 2000-08-21 | 2006-10-03 | Dow Global Technologies Inc. | Organosilicate resins as hardmasks for organic polymer dielectrics in fabrication of microelectronic devices |
| US6710450B2 (en) * | 2001-02-28 | 2004-03-23 | International Business Machines Corporation | Interconnect structure with precise conductor resistance and method to form same |
| JP5320653B2 (ja) | 2001-03-26 | 2013-10-23 | Ｊｓｒ株式会社 | 膜形成用組成物および絶縁膜形成用材料 |
| AU2002305835A1 (en) * | 2001-06-08 | 2002-12-23 | The Regents Of The University Of Michigan | Low-temperature patterned wafer bonding with photosensitive benzocylobutene (bcb) and 3d microelectromechanical systems fabrication |
| CN1630744A (zh) * | 2001-09-07 | 2005-06-22 | 博登化学公司 | 使用粘合促进剂的涂覆光纤及其制备和使用方法 |
| US6806182B2 (en) * | 2002-05-01 | 2004-10-19 | International Business Machines Corporation | Method for eliminating via resistance shift in organic ILD |
| TW200426191A (en) * | 2003-03-27 | 2004-12-01 | Sumitomo Chemical Co | Coating liquid for forming insulating film and method for producing insulating film |
| TW200505966A (en) | 2003-04-02 | 2005-02-16 | Dow Global Technologies Inc | Organosilicate resin formulation for use in microelectronic devices |
| US7164197B2 (en) * | 2003-06-19 | 2007-01-16 | 3M Innovative Properties Company | Dielectric composite material |
| US20050100712A1 (en) * | 2003-11-12 | 2005-05-12 | Simmons Blake A. | Polymerization welding and application to microfluidics |
| US8790632B2 (en) * | 2004-10-07 | 2014-07-29 | Actamax Surgical Materials, Llc | Polymer-based tissue-adhesive form medical use |
| JP2006104375A (ja) * | 2004-10-07 | 2006-04-20 | Sumitomo Chemical Co Ltd | 絶縁膜形成用塗布液、絶縁膜の製造方法および絶縁膜 |
| US20060275616A1 (en) * | 2005-06-03 | 2006-12-07 | Clough Robert S | Silane-based coupling agent |
| US20070004844A1 (en) * | 2005-06-30 | 2007-01-04 | Clough Robert S | Dielectric material |
| US8679536B2 (en) * | 2005-08-24 | 2014-03-25 | Actamax Surgical Materials, Llc | Aldol-crosslinked polymeric hydrogel adhesives |
| US8679537B2 (en) * | 2005-08-24 | 2014-03-25 | Actamaz Surgical Materials, LLC | Methods for sealing an orifice in tissue using an aldol-crosslinked polymeric hydrogel adhesive |
| US7390377B1 (en) | 2005-09-22 | 2008-06-24 | Sandia Corporation | Bonding thermoplastic polymers |
| CN101616750B (zh) * | 2007-05-01 | 2012-07-25 | 贝克株式会社 | 涂装方法 |
| CA2733682C (en) * | 2008-08-12 | 2014-10-14 | Air Products And Chemicals, Inc. | Polymeric compositions comprising per(phenylethynyl) arene derivatives |
| GB2480451A (en) * | 2010-05-18 | 2011-11-23 | E2V Tech | Electron tube rf output window |
| US9006353B2 (en) | 2011-11-18 | 2015-04-14 | Delsper LP | Crosslinking compounds for high glass transition temperature polymers |
| KR20140023856A (ko) * | 2012-08-16 | 2014-02-27 | 동우 화인켐 주식회사 | 아크릴계 점착제 조성물 |
| KR102197418B1 (ko) | 2012-10-22 | 2020-12-31 | 델스퍼 엘피 | 가교된 유기 중합체 조성물 |
| US9273215B2 (en) | 2012-10-30 | 2016-03-01 | Rohm And Haas Electronic Materials Llc | Adhesion promoter |
| JP6272908B2 (ja) | 2013-01-28 | 2018-01-31 | デルスパー リミテッド パートナーシップ | シーリングおよび耐摩耗性構成部材のための抗押出性組成物 |
| CA2906858C (en) | 2013-03-15 | 2021-09-21 | Delsper LP | Cross-linked organic polymers for use as elastomers |
| CN103755964B (zh) * | 2013-12-27 | 2016-03-30 | 深圳市安品有机硅材料有限公司 | 聚硅氧烷增粘树脂及其制备方法 |
| US9153357B1 (en) * | 2014-03-27 | 2015-10-06 | Rohm And Haas Electronic Materials Llc | Adhesion promoter |
| KR101623771B1 (ko) * | 2014-10-16 | 2016-05-25 | 도레이첨단소재 주식회사 | 저유전율을 갖는 터치스크린 패널용 점착 수지 조성물 및 이를 이용한 점착필름 |
| US9481810B2 (en) | 2014-12-15 | 2016-11-01 | Rohm And Haas Electronic Materials Llc | Silylated polyarylenes |
| US10790146B2 (en) * | 2016-12-05 | 2020-09-29 | Rohm And Haas Electronic Materials Llc | Aromatic resins for underlayers |
| BR112022022724A2 (pt) | 2020-06-05 | 2023-02-14 | Dow Global Technologies Llc | Composição, método para a produção da composição, composição adesiva, método para produzir um laminado, e, laminado |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301721A (enExample) | 1962-12-21 | 1900-01-01 | ||
| US3922299A (en) | 1974-03-05 | 1975-11-25 | Univ Delaware | Vinylic substitution reactions |
| US4642329A (en) | 1984-08-27 | 1987-02-10 | The Dow Chemical Company | Prepolymer processing of arylcyclobutene monomeric compositions |
| US4826997A (en) | 1984-08-27 | 1989-05-02 | The Dow Chemical Company | N-Substituted arylcyclo butenyl-maleimides |
| US4999449A (en) | 1984-08-27 | 1991-03-12 | The Dow Chemical Company | Novel poly(arylcyclobutenes) |
| US4724260A (en) | 1984-08-27 | 1988-02-09 | The Dow Chemical Company | Unsaturated alkyl monoarylcyclobutane monomers |
| US4540763A (en) | 1984-09-14 | 1985-09-10 | The Dow Chemical Company | Polymers derived from poly(arylcyclobutenes) |
| DE3578980D1 (de) | 1984-11-07 | 1990-09-06 | Gen Electric | Silanderivate zur verbesserung der eigenschaften von polyphenylenoxid-polyamidzusammensetzungen. |
| US4783514A (en) | 1986-02-28 | 1988-11-08 | The Dow Chemical Company | Polymeric monoarylcyclobutane compositions |
| US4687823A (en) | 1986-07-01 | 1987-08-18 | The Dow Chemical Company | Alkynyl-bridged poly(arylcyclobutene) resins |
| US4730030A (en) | 1986-07-25 | 1988-03-08 | The Dow Chemical Company | Arylcyclobutane/dienophile copolymer |
| US4732858A (en) | 1986-09-17 | 1988-03-22 | Brewer Science, Inc. | Adhesion promoting product and process for treating an integrated circuit substrate |
| US4950583A (en) | 1986-09-17 | 1990-08-21 | Brewer Science Inc. | Adhesion promoting product and process for treating an integrated circuit substrate therewith |
| JPH0749516B2 (ja) | 1987-01-28 | 1995-05-31 | 東レ・ダウコーニング・シリコーン株式会社 | ポリフエニレンオキサイド樹脂組成物 |
| US4759874A (en) | 1987-08-03 | 1988-07-26 | The Dow Chemical Company | Benzocyclobutene-based die attach adhesive compositions |
| US4812588A (en) | 1987-12-14 | 1989-03-14 | The Dow Chemical Company | Polyorganosiloxane-bridged bisbenzocyclobutene monomers |
| US4831172A (en) | 1988-03-23 | 1989-05-16 | The Dow Chemical Company | Benzocyclobutene-based organosilane adhesion aids |
| US5002808A (en) | 1988-03-23 | 1991-03-26 | The Dow Chemical Company | Adhesion methods employing benzocyclobutene-based organosilane adhesion aids |
| JP2594142B2 (ja) | 1988-11-30 | 1997-03-26 | 東芝シリコーン株式会社 | 電子部品の製造方法 |
| US4973636A (en) | 1989-05-30 | 1990-11-27 | Shell Oil Company | Bisbenzocyclobutene/bisimide compositions |
| US5246782A (en) | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
| US5025080A (en) | 1990-03-30 | 1991-06-18 | Shell Oil Company | Resin composition from di(arylcyclobutenealkyl) ether of di(hydroxyphenyl) oligomer |
| EP0457351A3 (en) | 1990-05-17 | 1993-03-10 | Mitsubishi Petrochemical Co., Ltd. | Process for producing silane-modified polyphenylene ether and thermoplastic resin composition containing the same |
| US5185391A (en) | 1991-11-27 | 1993-02-09 | The Dow Chemical Company | Oxidation inhibited arylcyclobutene polymers |
| CA2125567A1 (en) | 1991-12-10 | 1993-06-24 | Frank L. Oaks | Photocurable cyclobutarene compositions |
| JP2965277B2 (ja) † | 1992-07-24 | 1999-10-18 | 松下電工株式会社 | ポリフェニレンオキサイド系樹脂組成物とこれを用いた金属箔張積層板 |
| US5416233A (en) | 1994-01-25 | 1995-05-16 | The Dow Chemical Company | Preparation of vinylsilane-benzocyclobutenes |
| US5668210A (en) | 1994-10-24 | 1997-09-16 | The Dow Chemical Company | Adhesion promoter and self-priming arylcyclobutene resin compositions |
| DE59610089D1 (de) | 1995-11-02 | 2003-03-06 | Ciba Sc Holding Ag | Härtbare Zusammensetzung enthaltend Cycloolefin, Silan und Füllstoff |
| US5965679A (en) | 1996-09-10 | 1999-10-12 | The Dow Chemical Company | Polyphenylene oligomers and polymers |
| JP3858426B2 (ja) | 1998-02-02 | 2006-12-13 | Ｊｓｒ株式会社 | ポリマー組成物 |
-
1998
- 1998-08-24 US US09/138,510 patent/US6184284B1/en not_active Expired - Lifetime
-
1999
- 1999-08-23 WO PCT/US1999/019242 patent/WO2000011096A1/en not_active Ceased
- 1999-08-23 KR KR1020017002305A patent/KR100604629B1/ko not_active Expired - Lifetime
- 1999-08-23 EP EP99943863A patent/EP1112329B2/en not_active Expired - Lifetime
- 1999-08-23 CN CNB998100188A patent/CN1210362C/zh not_active Expired - Lifetime
- 1999-08-23 DE DE69918316T patent/DE69918316T3/de not_active Expired - Lifetime
- 1999-08-23 JP JP2000566357A patent/JP4343443B2/ja not_active Expired - Lifetime
- 1999-08-24 TW TW088114471A patent/TWI234577B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI646145B (zh) * | 2015-04-06 | 2019-01-01 | 美商羅門哈斯電子材料有限公司 | 聚伸芳基聚合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6184284B1 (en) | 2001-02-06 |
| JP2002523549A (ja) | 2002-07-30 |
| DE69918316T2 (de) | 2005-07-21 |
| KR100604629B1 (ko) | 2006-07-28 |
| EP1112329A1 (en) | 2001-07-04 |
| EP1112329B1 (en) | 2004-06-23 |
| DE69918316T3 (de) | 2011-02-24 |
| WO2000011096A1 (en) | 2000-03-02 |
| JP4343443B2 (ja) | 2009-10-14 |
| EP1112329B2 (en) | 2010-07-14 |
| DE69918316D1 (de) | 2004-07-29 |
| KR20010089172A (ko) | 2001-09-29 |
| CN1210362C (zh) | 2005-07-13 |
| CN1318093A (zh) | 2001-10-17 |
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