CA1222588A - Glass-filled polyarylene sulfide compositions containing organosilanes - Google Patents
Glass-filled polyarylene sulfide compositions containing organosilanesInfo
- Publication number
- CA1222588A CA1222588A CA000409152A CA409152A CA1222588A CA 1222588 A CA1222588 A CA 1222588A CA 000409152 A CA000409152 A CA 000409152A CA 409152 A CA409152 A CA 409152A CA 1222588 A CA1222588 A CA 1222588A
- Authority
- CA
- Canada
- Prior art keywords
- organosilane
- polyarylene sulfide
- accordance
- composition
- glass
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 150000001282 organosilanes Chemical class 0.000 title claims abstract description 57
- 229920000412 polyarylene Polymers 0.000 title claims abstract description 56
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 239000011521 glass Substances 0.000 title claims abstract description 32
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 25
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 24
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 24
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- -1 Trimethylsilylpropylazide 3-Ureidopropyltrimethoxysilane Chemical compound 0.000 claims description 5
- KUYYYOVFFCXPJQ-UHFFFAOYSA-N (2-chloro-3-phenylpropyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)CC(Cl)CC1=CC=CC=C1 KUYYYOVFFCXPJQ-UHFFFAOYSA-N 0.000 claims description 4
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 claims 4
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims 4
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 claims 4
- AWPZIUSASIFKDC-UHFFFAOYSA-N 3-azidopropyl(trimethyl)silane Chemical group C[Si](C)(C)CCCN=[N+]=[N-] AWPZIUSASIFKDC-UHFFFAOYSA-N 0.000 claims 3
- LVACOMKKELLCHJ-UHFFFAOYSA-N 3-trimethoxysilylpropylurea Chemical group CO[Si](OC)(OC)CCCNC(N)=O LVACOMKKELLCHJ-UHFFFAOYSA-N 0.000 claims 3
- CMHMPWTVCLNWAX-UHFFFAOYSA-N n-ethyl-n-(3-trimethoxysilylpropyldisulfanyl)ethanamine Chemical group CCN(CC)SSCCC[Si](OC)(OC)OC CMHMPWTVCLNWAX-UHFFFAOYSA-N 0.000 claims 3
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 claims 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims 2
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 claims 2
- KCYRMQZMDFIUQE-UHFFFAOYSA-N trimethyl [phenyl-bis(trimethoxysilyloxy)silyl] silicate Chemical compound CO[Si](OC)(OC)O[Si](O[Si](OC)(OC)OC)(O[Si](OC)(OC)OC)C1=CC=CC=C1 KCYRMQZMDFIUQE-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000465 moulding Methods 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 13
- 229910000077 silane Inorganic materials 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 8
- 150000004763 sulfides Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 229920013632 Ryton Polymers 0.000 description 2
- 239000004736 Ryton® Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- MPRRJXMALKDPON-UHFFFAOYSA-N 3-[[3-(diethylamino)-3-trimethoxysilylpropyl]disulfanyl]-n,n-diethyl-1-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)C([Si](OC)(OC)OC)CCSSCCC(N(CC)CC)[Si](OC)(OC)OC MPRRJXMALKDPON-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 101001010626 Homo sapiens Interleukin-22 Proteins 0.000 description 1
- 102100030703 Interleukin-22 Human genes 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- XPDGHGYGTJOTBC-UHFFFAOYSA-N methoxy(methyl)silicon Chemical compound CO[Si]C XPDGHGYGTJOTBC-UHFFFAOYSA-N 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Glass Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30085981A | 1981-09-10 | 1981-09-10 | |
| US300,859 | 1981-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1222588A true CA1222588A (en) | 1987-06-02 |
Family
ID=23160888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409152A Expired CA1222588A (en) | 1981-09-10 | 1982-08-10 | Glass-filled polyarylene sulfide compositions containing organosilanes |
Country Status (8)
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782195A (en) * | 1982-07-16 | 1988-11-01 | Phillips Petroleum Company | Encapsulation of electronic components with poly(arylene sulfide) containing mercaptosilane |
| US4482665A (en) * | 1982-09-14 | 1984-11-13 | Phillips Petroleum Company | Encapsulation of electronic components with calcium silicate-containing poly(arylene sulfide) compositions |
| JPS6011062B2 (ja) * | 1982-10-13 | 1985-03-22 | 東レ株式会社 | ガラス繊維強化ポリフエニレンスルフイド樹脂組成物 |
| DE3339581A1 (de) * | 1983-11-02 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Polyarylensulfide mit verminderter korrosion |
| DE3426918A1 (de) * | 1984-07-21 | 1986-01-23 | Bayer Ag, 5090 Leverkusen | Faserverstaerktes polyphenylensulfid |
| CA1241482A (en) * | 1985-04-16 | 1988-08-30 | John E. Leland | Poly(arylene sulfide) compositions with improved insulation resistance and cracking resistance |
| JPH07742B2 (ja) * | 1986-04-03 | 1995-01-11 | 大日本インキ化学工業株式会社 | ポリフエニレンサルフアイド樹脂組成物 |
| JPH0621169B2 (ja) * | 1987-04-06 | 1994-03-23 | ポリプラスチックス株式会社 | 改良されたポリフエニレンサルフアイド樹脂の製造方法 |
| EP0302648A3 (en) * | 1987-08-03 | 1989-08-09 | Polyplastics Co. Ltd. | Weld-containing polyarylene sulfide resin molded article |
| JPH07107128B2 (ja) * | 1987-10-14 | 1995-11-15 | 東レ株式会社 | ポリフェニレンスルフィド組成物 |
| JPH01146955A (ja) * | 1987-12-03 | 1989-06-08 | Kureha Chem Ind Co Ltd | ポリフェニレンスルフィド樹脂組成物 |
| JPH01228815A (ja) * | 1988-03-09 | 1989-09-12 | Toray Ind Inc | ポリフェニレンサルファイド射出成形材料 |
| CA2014561A1 (en) * | 1989-06-05 | 1990-12-05 | Roy F. Wright | Glass-filled poly(arylene sulfide) compositions and methods |
| DE69724367T2 (de) * | 1996-04-02 | 2004-06-24 | Dainippon Ink & Chemicals, Inc. | Polyarylensulfid und zusammensetzung |
| US6820985B2 (en) | 2000-04-19 | 2004-11-23 | Matsushita Electric Industrial Co., Ltd. | Display panel and production method therefor |
| ATE442407T1 (de) * | 2001-06-28 | 2009-09-15 | Michelin Soc Tech | Kautschukzusammensetzung für reifen, die ein kupplungsmittel der polythiosulfenamid-gruppe enthält |
| FR2826655B1 (fr) * | 2001-06-28 | 2003-08-22 | Rhodia Chimie Sa | Composes organosiliciques utilisables notamment en tant qu'agent de couplage, compositions d'elastomere(s) les contenant et articles en elastomere(s) prepares a partir de telles compositions |
| JP4391238B2 (ja) * | 2001-12-20 | 2009-12-24 | ソシエテ ド テクノロジー ミシュラン | ポリチオスルフェンアミド官能基を有するカップリング剤を含むタイヤ用ゴム組成物 |
| FR2833958B1 (fr) * | 2001-12-20 | 2005-08-19 | Rhodia Chimie Sa | Composes organosiliciques utilisables notamment en tant qu'agent de couplage, compositions d'elastomeres(s) les contenant et articles en elastomeres(s) prepares a partir de telles compositions |
| US20150166731A1 (en) * | 2013-12-16 | 2015-06-18 | Chevron Phillips Chemical Company Lp | Reinforced Poly(Arylene Sulfide) Polymer Compositions |
| KR102492258B1 (ko) * | 2016-04-26 | 2023-01-26 | 에이치디씨폴리올 주식회사 | 내가수분해성이 우수한 폴리아릴렌 설파이드 수지 조성물 |
| WO2019054498A1 (ja) * | 2017-09-15 | 2019-03-21 | 国立研究開発法人産業技術総合研究所 | オルガノシロキサン及びオルガノシロキサンの製造方法 |
| MY195787A (en) * | 2020-02-10 | 2023-02-20 | Polyplastics Co | Method of Producing Polyarylene Sulfide Resin Composition |
| WO2021161996A1 (ja) * | 2020-02-10 | 2021-08-19 | ポリプラスチックス株式会社 | ポリアリーレンサルファイド樹脂組成物の製造方法 |
| CN112662370B (zh) * | 2020-12-16 | 2022-10-28 | 江西晨光新材料股份有限公司 | 一种单组分脱醇硅酮密封胶及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284549A (en) * | 1977-07-27 | 1981-08-18 | Hooker Chemicals & Plastics Corp. | Polymer blends with improved hydrolytic stability |
-
1982
- 1982-08-10 CA CA000409152A patent/CA1222588A/en not_active Expired
- 1982-08-27 ZA ZA826302A patent/ZA826302B/xx unknown
- 1982-09-09 DE DE8282108342T patent/DE3278138D1/de not_active Expired
- 1982-09-09 ES ES515610A patent/ES515610A0/es active Granted
- 1982-09-09 EP EP82108342A patent/EP0074632B1/en not_active Expired
- 1982-09-09 AT AT82108342T patent/ATE32604T1/de not_active IP Right Cessation
- 1982-09-09 DK DK403882A patent/DK403882A/da not_active Application Discontinuation
- 1982-09-10 JP JP57157956A patent/JPS5865750A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5865750A (ja) | 1983-04-19 |
| ES8403502A1 (es) | 1984-04-01 |
| ES515610A0 (es) | 1984-04-01 |
| EP0074632A2 (en) | 1983-03-23 |
| DK403882A (da) | 1983-03-11 |
| DE3278138D1 (en) | 1988-03-31 |
| JPH032905B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-17 |
| EP0074632B1 (en) | 1988-02-24 |
| ATE32604T1 (de) | 1988-03-15 |
| ZA826302B (en) | 1983-07-27 |
| EP0074632A3 (en) | 1983-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20040602 |