CA2153328A1 - Toughened polyphenylene sulfide compositions and method of making the same - Google Patents
Toughened polyphenylene sulfide compositions and method of making the sameInfo
- Publication number
- CA2153328A1 CA2153328A1 CA 2153328 CA2153328A CA2153328A1 CA 2153328 A1 CA2153328 A1 CA 2153328A1 CA 2153328 CA2153328 CA 2153328 CA 2153328 A CA2153328 A CA 2153328A CA 2153328 A1 CA2153328 A1 CA 2153328A1
- Authority
- CA
- Canada
- Prior art keywords
- polyphenylene sulfide
- composition according
- composition
- terpolymer
- group
- 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.)
- Abandoned
Links
- 239000004734 Polyphenylene sulfide Substances 0.000 title claims abstract description 81
- 229920000069 polyphenylene sulfide Polymers 0.000 title claims abstract description 81
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229920001897 terpolymer Polymers 0.000 claims abstract description 44
- 150000001336 alkenes Chemical class 0.000 claims abstract description 31
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 31
- -1 acrylic ester Chemical group 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 17
- 239000003365 glass fiber Substances 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 8
- 239000004917 carbon fiber Substances 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 239000012744 reinforcing agent Substances 0.000 claims abstract description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical group CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims description 2
- 229920006231 aramid fiber Polymers 0.000 claims description 2
- 239000011324 bead Substances 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 claims description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012763 reinforcing filler Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- CGPRUXZTHGTMKW-UHFFFAOYSA-N ethene;ethyl prop-2-enoate Chemical compound C=C.CCOC(=O)C=C CGPRUXZTHGTMKW-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920013683 Celanese Polymers 0.000 description 2
- 229920013633 Fortron Polymers 0.000 description 2
- 239000004738 Fortron® Substances 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 229920013632 Ryton Polymers 0.000 description 2
- 239000004736 Ryton® Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical class [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite 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
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US228793A | 1993-01-08 | 1993-01-08 | |
| US08/002,287 | 1993-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2153328A1 true CA2153328A1 (en) | 1994-07-21 |
Family
ID=21700082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2153328 Abandoned CA2153328A1 (en) | 1993-01-08 | 1994-01-04 | Toughened polyphenylene sulfide compositions and method of making the same |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0678114A1 (enrdf_load_stackoverflow) |
| JP (1) | JPH08506128A (enrdf_load_stackoverflow) |
| AU (1) | AU5991094A (enrdf_load_stackoverflow) |
| BR (1) | BR9405652A (enrdf_load_stackoverflow) |
| CA (1) | CA2153328A1 (enrdf_load_stackoverflow) |
| WO (1) | WO1994016018A1 (enrdf_load_stackoverflow) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011012139A (ja) * | 2009-06-30 | 2011-01-20 | Tosoh Corp | ポリアリーレンスルフィド組成物 |
| KR101355472B1 (ko) * | 2010-12-31 | 2014-01-28 | 제일모직주식회사 | 고열전도성 수지 조성물 |
| KR101368315B1 (ko) * | 2010-12-31 | 2014-02-27 | 제일모직주식회사 | 밀드 피치계 탄소섬유를 포함하는 고열전도성 수지 조성물 |
| US9494262B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Automotive fuel lines including a polyarylene sulfide |
| US9494260B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Dynamically vulcanized polyarylene sulfide composition |
| US9765219B2 (en) | 2012-04-13 | 2017-09-19 | Ticona Llc | Polyarylene sulfide components for heavy duty trucks |
| US9493646B2 (en) | 2012-04-13 | 2016-11-15 | Ticona Llc | Blow molded thermoplastic composition |
| US9758674B2 (en) | 2012-04-13 | 2017-09-12 | Ticona Llc | Polyarylene sulfide for oil and gas flowlines |
| JP6626444B2 (ja) | 2013-08-27 | 2019-12-25 | ティコナ・エルエルシー | 射出成形用の耐熱性強化熱可塑性組成物 |
| JP6714510B2 (ja) | 2013-08-27 | 2020-06-24 | ティコナ・エルエルシー | 炭化水素取り込みの低い熱可塑性組成物 |
| WO2015146718A1 (ja) * | 2014-03-27 | 2015-10-01 | 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系樹脂組成物及びインサート成形体 |
| WO2016094381A1 (en) | 2014-12-11 | 2016-06-16 | Ticona Llc | Stabilized flexible thermoplastic composition and products formed therefrom |
| CN104817831A (zh) * | 2015-05-21 | 2015-08-05 | 国网智能电网研究院 | 一种电气绝缘热塑性树脂组合物及其制备方法 |
| KR102695731B1 (ko) | 2015-12-11 | 2024-08-14 | 티코나 엘엘씨 | 가교결합성 폴리아릴렌 설파이드 조성물 |
| CN108368339A (zh) | 2015-12-11 | 2018-08-03 | 提克纳有限责任公司 | 聚芳硫醚组合物 |
| WO2017161534A1 (en) | 2016-03-24 | 2017-09-28 | Ticona Llc | Composite structure |
| JP6987183B1 (ja) * | 2020-06-29 | 2021-12-22 | ポリプラスチックス株式会社 | 押出成形又はブロー成形用ポリアリーレンサルファイド樹脂組成物 |
| CN112724675A (zh) * | 2020-12-29 | 2021-04-30 | 富海(东营)新材料科技有限公司 | 一种聚苯硫醚复合材料及其制备方法 |
| CN112778762B (zh) * | 2020-12-31 | 2023-01-10 | 上海聚威新材料股份有限公司 | 一种导电pps复合材料及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3671458D1 (de) * | 1985-12-27 | 1990-06-28 | Toray Industries | Polyphenylensulfidharzzusammensetzung und verfahren zu ihrer herstellung. |
| JPH0662849B2 (ja) * | 1988-02-03 | 1994-08-17 | 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 |
| JPH01306467A (ja) * | 1988-06-02 | 1989-12-11 | Toray Ind Inc | ポリフェニレンスルフィド組成物 |
| US5204405A (en) * | 1988-11-09 | 1993-04-20 | Nippon Petrochemicals Co., Ltd. | Thermoplastic resin composition and method for preparing the same |
| EP0484273A1 (de) * | 1990-10-08 | 1992-05-06 | Ciba-Geigy Ag | Polyarylensulfidzusammensetzungen |
| JP3042008B2 (ja) * | 1991-05-08 | 2000-05-15 | 東レ株式会社 | ブロー中空成形品 |
| BE1006353A3 (fr) * | 1991-12-13 | 1994-08-02 | Solvay | Compositions a base de polysulfure de phenylene de resistance au choc amelioree et procede pour les preparer. |
-
1994
- 1994-01-04 WO PCT/US1994/000103 patent/WO1994016018A1/en not_active Application Discontinuation
- 1994-01-04 JP JP6516159A patent/JPH08506128A/ja active Pending
- 1994-01-04 BR BR9405652A patent/BR9405652A/pt not_active Application Discontinuation
- 1994-01-04 AU AU59910/94A patent/AU5991094A/en not_active Withdrawn
- 1994-01-04 EP EP94906024A patent/EP0678114A1/en not_active Withdrawn
- 1994-01-04 CA CA 2153328 patent/CA2153328A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08506128A (ja) | 1996-07-02 |
| WO1994016018A1 (en) | 1994-07-21 |
| BR9405652A (pt) | 1995-11-14 |
| EP0678114A4 (enrdf_load_stackoverflow) | 1995-12-06 |
| AU5991094A (en) | 1994-08-15 |
| EP0678114A1 (en) | 1995-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |