CA1228445A - Stabilized sulfur-containing resins, such as polyphenylene sulfide and method of producing the same - Google Patents
Stabilized sulfur-containing resins, such as polyphenylene sulfide and method of producing the sameInfo
- Publication number
- CA1228445A CA1228445A CA000407039A CA407039A CA1228445A CA 1228445 A CA1228445 A CA 1228445A CA 000407039 A CA000407039 A CA 000407039A CA 407039 A CA407039 A CA 407039A CA 1228445 A CA1228445 A CA 1228445A
- Authority
- CA
- Canada
- Prior art keywords
- polyphenylene sulfide
- sulfur
- weight
- polymer
- exhaust gases
- 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
- 239000004734 Polyphenylene sulfide Substances 0.000 title claims abstract description 40
- 229920000069 polyphenylene sulfide Polymers 0.000 title claims abstract description 39
- 229910052717 sulfur Inorganic materials 0.000 title claims description 44
- 239000011593 sulfur Substances 0.000 title claims description 44
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 43
- 238000000034 method Methods 0.000 title claims description 24
- 229920005989 resin Polymers 0.000 title description 16
- 239000011347 resin Substances 0.000 title description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 61
- 239000000654 additive Substances 0.000 claims abstract description 37
- 230000000996 additive effect Effects 0.000 claims abstract description 34
- 239000007789 gas Substances 0.000 claims abstract description 31
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 229930194542 Keto Natural products 0.000 claims abstract 2
- 239000000463 material Substances 0.000 claims description 23
- GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- -1 aromatic imides Chemical class 0.000 claims description 11
- 239000004952 Polyamide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 150000004982 aromatic amines Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229920002530 polyetherether ketone Polymers 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 3
- 239000002250 absorbent Substances 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000008365 aromatic ketones Chemical group 0.000 claims 5
- 150000008430 aromatic amides Chemical class 0.000 claims 2
- 239000004642 Polyimide Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 229920001721 polyimide Polymers 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 abstract description 3
- 238000011105 stabilization Methods 0.000 abstract description 3
- 230000000087 stabilizing effect Effects 0.000 abstract description 3
- 150000003384 small molecules Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000000875 corresponding effect Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 229920002492 poly(sulfone) Polymers 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 229920000265 Polyparaphenylene Polymers 0.000 description 4
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 4
- 229910052808 lithium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229920002972 Acrylic fiber Polymers 0.000 description 2
- 241000282320 Panthera leo Species 0.000 description 2
- 239000004963 Torlon Substances 0.000 description 2
- 229920003997 Torlon® Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000006253 efflorescence Methods 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical class COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HBQUOLGAXBYZGR-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 HBQUOLGAXBYZGR-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101710200331 Cytochrome b-245 chaperone 1 Proteins 0.000 description 1
- 102100037186 Cytochrome b-245 chaperone 1 Human genes 0.000 description 1
- 101710119396 Cytochrome b-245 chaperone 1 homolog Proteins 0.000 description 1
- 241001505295 Eros Species 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- 208000037062 Polyps Diseases 0.000 description 1
- 229920013632 Ryton Polymers 0.000 description 1
- 239000004736 Ryton® Substances 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002831 nitrogen free-radicals Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 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
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0286—Chemical after-treatment
- C08G75/029—Modification with organic compounds
-
- 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
- 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
- C08L81/06—Polysulfones; Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3127355.6 | 1981-07-10 | ||
| DE3127355 | 1981-07-10 | ||
| DE19823209525 DE3209525A1 (de) | 1981-07-10 | 1982-03-16 | Stabilisierung von polyphenylensulfid gegen korrosive ausgasungen |
| DEP3209525.2 | 1982-03-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1228445A true CA1228445A (en) | 1987-10-20 |
Family
ID=25794493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000407039A Expired CA1228445A (en) | 1981-07-10 | 1982-07-09 | Stabilized sulfur-containing resins, such as polyphenylene sulfide and method of producing the same |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US4447581A (enExample) |
| EP (1) | EP0070010B1 (enExample) |
| CA (1) | CA1228445A (enExample) |
| DE (1) | DE3209525A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5516876A (en) | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5780583A (en) * | 1991-01-09 | 1998-07-14 | The Boeing Company | Reactive polyarylene sulfide oligomers |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US4703088A (en) * | 1981-12-18 | 1987-10-27 | Phillips Petroleum Company | Mold corrosion inhibitors |
| DE3339581A1 (de) * | 1983-11-02 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Polyarylensulfide mit verminderter korrosion |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5610317A (en) | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| JPS6297821A (ja) * | 1985-10-25 | 1987-05-07 | Kureha Chem Ind Co Ltd | 透明で着色の少ないポリアリーレンチオエーテル溶融成形物およびその製造法 |
| US4690972A (en) * | 1986-04-04 | 1987-09-01 | Phillips Petroleum Company | Method of producing poly(arylene sulfide) compositions and articles made therefrom |
| US4757120A (en) * | 1986-10-03 | 1988-07-12 | Ici Americas Inc. | Polyimide/aromatic sulfone resin blends and prepegs coated therewith |
| DE3637813A1 (de) * | 1986-11-06 | 1988-05-19 | Bayer Ag | Verfahren zur herstellung von polyarylensulfiden mit erniedrigter kristallisationstemperatur |
| CA1304534C (en) * | 1987-05-15 | 1992-06-30 | Yutaka Kobayashi | Melt-stable poly(arylene thioether-ketone) and production process thereof |
| US4826906A (en) * | 1987-06-22 | 1989-05-02 | Kureha Kagaku Kogyo K.K. | Poly(arylene thioether-ketone) compositions improved in both melt stability and crystallinity |
| DE3738142A1 (de) * | 1987-11-10 | 1989-05-18 | Bayer Ag | Verfahren zur herstellung von polyarylensulfiden mit definiert einstellbaren schmelzviskositaeten |
| EP0317820B1 (de) * | 1987-11-27 | 1992-07-15 | Siemens Aktiengesellschaft | Verfahren zur Stabilisierung von Polyphenylensulfid gegen thermischen Abbau und Ausgasungen organischer Substanzen |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5149749A (en) * | 1990-05-31 | 1992-09-22 | Phillips Petroleum Company | Poly(phenylene sulfide) composition and articles having improved thermal stability at high temperatures |
| US5210128A (en) * | 1991-07-24 | 1993-05-11 | Phillips Petroleum Company | Poly(arylene sulfide) compositions, composites, and methods of production |
| DE4325287A1 (de) * | 1993-07-28 | 1995-02-02 | Leybold Ag | Kunststoff für die Verwendung im Vacuum |
| US6280323B1 (en) | 1996-11-21 | 2001-08-28 | Konami Co., Ltd. | Device, method and storage medium for displaying penalty kick match cursors in a video soccer game |
| US7128806B2 (en) * | 2003-10-21 | 2006-10-31 | Applied Materials, Inc. | Mask etch processing apparatus |
| CN101885843B (zh) * | 2010-07-26 | 2012-05-30 | 四川大学 | 水溶性聚苯硫醚及其制备方法 |
| CN102634210B (zh) * | 2012-04-20 | 2013-06-12 | 陈逊 | 一种纤维级聚苯硫醚树脂切片的制造工艺 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE332078B (enExample) * | 1963-03-25 | 1971-01-25 | Thiokol Chemical Corp | |
| GB1334857A (en) * | 1970-05-07 | 1973-10-24 | Ici Ltd | Thermoplastic polymer blends |
| FR2102796A5 (enExample) * | 1970-08-21 | 1972-04-07 | Rhone Poulenc Sa | |
| US3988286A (en) * | 1974-08-23 | 1976-10-26 | Phillips Petroleum Company | Heat curable poly(arylene sulfide) compositions |
| US4017555A (en) * | 1976-06-21 | 1977-04-12 | Alvarez Robert T | Polyalloy of polyphenylene sulfide and polyimide |
| US4071509A (en) * | 1976-08-13 | 1978-01-31 | Phillips Petroleum Company | Arylene sulfide polymer purification |
| US4115344A (en) * | 1977-07-05 | 1978-09-19 | Phillips Petroleum Company | Mold corrosion inhibition in poly(arylene) sulfide processing |
| WO1980000349A1 (fr) * | 1978-08-04 | 1980-03-06 | Toray Industries | Composition de resine de moulage a resistance thermique |
| DE2836045A1 (de) * | 1978-08-17 | 1980-02-28 | Bosch Gmbh Robert | Kontaktkoerper fuer elektrischen stromkreis |
| DE2911269C2 (de) * | 1979-03-22 | 1982-12-09 | Dr. Beck & Co Ag, 2000 Hamburg | Verwendung von Thermoplasten zur Herstellung von isolierten Wickeldrähten im Extrusionsverfahren |
| US4238585A (en) * | 1979-08-10 | 1980-12-09 | Thiokol Corporation | Aryl amine terminated polysulfide polymers, related compounds and processes for their preparation |
| US4282347A (en) * | 1979-08-14 | 1981-08-04 | Phillips Petroleum Company | Preparation of branched polymers of arylene sulfide |
| JPS5790018A (en) * | 1980-11-27 | 1982-06-04 | Toray Ind Inc | Stabilized polyphenylene sulfide and its production |
| CA1191989A (en) * | 1981-03-30 | 1985-08-13 | Union Carbide Corporation | Alloys of a poly(arylene sulfide) and a poly(aryl ketone) |
-
1982
- 1982-03-16 DE DE19823209525 patent/DE3209525A1/de active Granted
- 1982-06-14 US US06/388,179 patent/US4447581A/en not_active Expired - Fee Related
- 1982-07-09 EP EP82106168A patent/EP0070010B1/de not_active Expired
- 1982-07-09 CA CA000407039A patent/CA1228445A/en not_active Expired
-
1983
- 1983-12-01 US US06/556,984 patent/US4482683A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0070010A2 (de) | 1983-01-19 |
| US4482683A (en) | 1984-11-13 |
| EP0070010B1 (de) | 1987-07-22 |
| DE3209525A1 (de) | 1983-01-27 |
| US4447581A (en) | 1984-05-08 |
| EP0070010A3 (en) | 1983-04-27 |
| DE3209525C2 (enExample) | 1988-06-09 |
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