CA1061925A - Heat curable poly(arylene sulfide) compositions - Google Patents
Heat curable poly(arylene sulfide) compositionsInfo
- Publication number
- CA1061925A CA1061925A CA227,667A CA227667A CA1061925A CA 1061925 A CA1061925 A CA 1061925A CA 227667 A CA227667 A CA 227667A CA 1061925 A CA1061925 A CA 1061925A
- Authority
- CA
- Canada
- Prior art keywords
- dichlorobenzene
- blend
- sulfide
- copolymer
- alkyl
- 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 91
- -1 poly(arylene sulfide Chemical compound 0.000 title claims abstract description 47
- 229920000642 polymer Polymers 0.000 claims abstract description 87
- 229920001577 copolymer Polymers 0.000 claims abstract description 76
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 24
- 229920001519 homopolymer Polymers 0.000 claims abstract description 12
- 230000001747 exhibiting effect Effects 0.000 claims abstract description 8
- 239000008199 coating composition Substances 0.000 claims abstract description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 43
- FUNUTBJJKQIVSY-UHFFFAOYSA-N 2,4-Dichlorotoluene Chemical compound CC1=CC=C(Cl)C=C1Cl FUNUTBJJKQIVSY-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims description 16
- 239000004744 fabric Substances 0.000 claims description 16
- 239000011521 glass Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 claims description 13
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 10
- UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 6
- 239000004917 carbon fiber Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229920002959 polymer blend Polymers 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 3
- YCFUHBHONRJFHI-UHFFFAOYSA-N 2,6-dichloronaphthalene Chemical compound C1=C(Cl)C=CC2=CC(Cl)=CC=C21 YCFUHBHONRJFHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 7
- 230000000704 physical effect Effects 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 abstract description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 22
- 238000001723 curing Methods 0.000 description 15
- 238000000576 coating method Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- AMCBMCWLCDERHY-UHFFFAOYSA-N 1,3-dichloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC(Cl)=C21 AMCBMCWLCDERHY-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052976 metal sulfide Inorganic materials 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- MOXLHAPKZWTHEX-UHFFFAOYSA-N 1,2-dichloronaphthalene Chemical class C1=CC=CC2=C(Cl)C(Cl)=CC=C21 MOXLHAPKZWTHEX-UHFFFAOYSA-N 0.000 description 1
- NCEGBVBIICYBGC-UHFFFAOYSA-N 1,3,5-triethyl-2,4,6-trifluorobenzene Chemical compound CCC1=C(F)C(CC)=C(F)C(CC)=C1F NCEGBVBIICYBGC-UHFFFAOYSA-N 0.000 description 1
- DNHRBCFMFYOUKM-UHFFFAOYSA-N 1,4-dibromo-2,5-diethylbenzene Chemical compound CCC1=CC(Br)=C(CC)C=C1Br DNHRBCFMFYOUKM-UHFFFAOYSA-N 0.000 description 1
- COKCBKBMKZUMME-UHFFFAOYSA-N 1,4-dibromo-2,6,8-triethylnaphthalene Chemical compound BrC1=C(CC)C=C(Br)C2=CC(CC)=CC(CC)=C21 COKCBKBMKZUMME-UHFFFAOYSA-N 0.000 description 1
- GRMLGYULZHLWRH-UHFFFAOYSA-N 1-bromo-3-(3-bromo-5-methylphenyl)-5-methylbenzene Chemical group CC1=CC(Br)=CC(C=2C=C(Br)C=C(C)C=2)=C1 GRMLGYULZHLWRH-UHFFFAOYSA-N 0.000 description 1
- GWCFTYITFDWLAY-UHFFFAOYSA-N 1-ethylazepan-2-one Chemical compound CCN1CCCCCC1=O GWCFTYITFDWLAY-UHFFFAOYSA-N 0.000 description 1
- HHIYLZLPWZTWAK-UHFFFAOYSA-N 2,5-diethyl-2,3,6-trifluoro-8-propyl-1h-quinoline Chemical compound C1=C(F)C(F)(CC)NC2=C1C(CC)=C(F)C=C2CCC HHIYLZLPWZTWAK-UHFFFAOYSA-N 0.000 description 1
- YTBRNEUEFCNVHC-UHFFFAOYSA-N 4,4'-dichlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1 YTBRNEUEFCNVHC-UHFFFAOYSA-N 0.000 description 1
- NFSYHEGDKRRKIC-UHFFFAOYSA-N 5,8-dichloro-1,2-diethylnaphthalene Chemical compound ClC1=CC=C(Cl)C2=C(CC)C(CC)=CC=C21 NFSYHEGDKRRKIC-UHFFFAOYSA-N 0.000 description 1
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YAVWDJDEOLOYQO-UHFFFAOYSA-N OOOOOOOOOO Chemical compound OOOOOOOOOO YAVWDJDEOLOYQO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
- C08G75/0209—Polyarylenethioethers derived from monomers containing one aromatic ring
- C08G75/0213—Polyarylenethioethers derived from monomers containing one aromatic ring containing elements other than carbon, hydrogen or sulfur
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
- B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
-
- 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
- C08G75/0227—Polyarylenethioethers derived from monomers containing two or more aromatic rings
-
- 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
- C08G75/0295—Modification with inorganic 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/103—Metal fibres
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/106—Carbon fibres, e.g. graphite fibres
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31533—Of polythioether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/500,181 US3988286A (en) | 1974-08-23 | 1974-08-23 | Heat curable poly(arylene sulfide) compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061925A true CA1061925A (en) | 1979-09-04 |
Family
ID=23988371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,667A Expired CA1061925A (en) | 1974-08-23 | 1975-05-23 | Heat curable poly(arylene sulfide) compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3988286A (enExample) |
| JP (1) | JPS543773B2 (enExample) |
| BE (1) | BE832441A (enExample) |
| CA (1) | CA1061925A (enExample) |
| DE (1) | DE2537166C2 (enExample) |
| FR (1) | FR2282453A1 (enExample) |
| GB (1) | GB1513296A (enExample) |
| IT (1) | IT1041978B (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212923A (en) * | 1975-03-20 | 1980-07-15 | Phillips Petroleum Company | Laminate using a poly(arylene sulfide)-polytetrafluoroethylene adhesive |
| US4108939A (en) * | 1976-06-21 | 1978-08-22 | International Business Machines Corporation | Porous polymeric bearing |
| JPS5390083A (en) * | 1977-01-19 | 1978-08-08 | Hitachi Zosen Corp | Method of positioning and centering intermediate bearing for stern pipe boring bar |
| US4212922A (en) * | 1978-10-02 | 1980-07-15 | Phillips Petroleum Company | Poly(arylene sulfide) resin coating |
| JPS55103705A (en) * | 1979-01-31 | 1980-08-08 | Kanegafuchi Chem Ind Co Ltd | Ferrite composition with high initial permeability and method of manufacturing its compact |
| US4337182A (en) * | 1981-03-26 | 1982-06-29 | Phillips Petroleum Company | Poly (arylene sulfide) composition suitable for use in semi-conductor encapsulation |
| DE3209525A1 (de) * | 1981-07-10 | 1983-01-27 | Siemens AG, 1000 Berlin und 8000 München | Stabilisierung von polyphenylensulfid gegen korrosive ausgasungen |
| US4880901A (en) * | 1982-08-03 | 1989-11-14 | Phillips Petroleum Company | Arylene sulfide terpolymers and processes for making them |
| AU544880B2 (en) * | 1982-08-03 | 1985-06-20 | Phillips Petroleum Co. | Arylene sulphide terpolymers |
| CA1238167A (en) * | 1983-04-07 | 1988-06-21 | James E. O'connor | Process for preparing shaped objects of poly(arylene sulfide) and product thereof |
| US4547313A (en) * | 1983-04-18 | 1985-10-15 | Phillips Petroleum Company | Conductive polymer composition |
| JPS59223753A (ja) * | 1983-06-03 | 1984-12-15 | Asahi Glass Co Ltd | ポリフエニレンサルフアイド樹脂成形材料 |
| JPS6123627A (ja) * | 1984-07-11 | 1986-02-01 | Kureha Chem Ind Co Ltd | ポリアリーレンスルフィドの製造法 |
| JPS61176658A (ja) * | 1985-01-31 | 1986-08-08 | Kureha Chem Ind Co Ltd | フエニレンスルフイド樹脂組成物 |
| US4711796A (en) * | 1985-01-31 | 1987-12-08 | Phillips Petroleum Company | Poly(arylene sulfide) coating compositions |
| US4689098A (en) * | 1985-10-11 | 1987-08-25 | Phillips Petroleum Company | Molding composition |
| JPS62240359A (ja) * | 1986-03-11 | 1987-10-21 | Kureha Chem Ind Co Ltd | ポリアリ−レンチオエ−テル組成物 |
| EP0257228A1 (en) * | 1986-07-25 | 1988-03-02 | Tohpren Co., Ltd. | Polyphenylene sulfide resin composition |
| US4921558A (en) * | 1987-11-16 | 1990-05-01 | Phillips Petroleum Company | Poly(arylene sulfide) composites |
| DE3921499A1 (de) * | 1989-06-30 | 1991-01-03 | Bayer Ag | Polyarylensulfidformmassen mit verbesserten mechanischen eigenschaften |
| US5189121A (en) * | 1989-09-25 | 1993-02-23 | Phillips Petroleum Company | Arylene sulfide copolymer coating compositions and processes |
| JP3027386B2 (ja) * | 1990-03-05 | 2000-04-04 | 呉羽化学工業株式会社 | ポリアリーレンチオエーテル樹脂組成物および押出成形物 |
| US5219983A (en) * | 1991-05-08 | 1993-06-15 | Phillips Petroleum Company | Preparation of poly (biphenylene/phenylene) sulfide |
| US5210128A (en) * | 1991-07-24 | 1993-05-11 | Phillips Petroleum Company | Poly(arylene sulfide) compositions, composites, and methods of production |
| JP7575974B2 (ja) * | 2021-03-15 | 2024-10-30 | 株式会社クレハ | ポリフェニレンスルフィド樹脂、及びその製造方法 |
| US20230085997A1 (en) * | 2021-09-23 | 2023-03-23 | Intel Corporation | Methods and apparatus to improve adhesion between metals and dielectrics in circuit devices |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524835A (en) * | 1963-11-27 | 1970-08-18 | Phillips Petroleum Co | Heat treatment of poly(arylene sulfide) resins |
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| US3396110A (en) * | 1964-11-30 | 1968-08-06 | Phillips Petroleum Co | Lubricant comprising sulfurcontaining polymer |
| US3622376A (en) * | 1968-08-15 | 1971-11-23 | Phillips Petroleum Co | TiO{11 {0 IN POLY(ARYLENE SULFIDE) FOR COATING COMPOSITION |
| US3607843A (en) * | 1969-05-16 | 1971-09-21 | Phillips Petroleum Co | Process for making poly (phenylene sulfide) polymers of increased molecular weight |
| US3716609A (en) * | 1970-10-05 | 1973-02-13 | United Aircraft Corp | Process for preparing molded structure from polyphenylene sulfide resin and filler |
| US3699087A (en) * | 1971-03-11 | 1972-10-17 | Phillips Petroleum Co | Heat treatment of aromatic sulfide polymers |
-
1974
- 1974-08-23 US US05/500,181 patent/US3988286A/en not_active Expired - Lifetime
-
1975
- 1975-05-23 CA CA227,667A patent/CA1061925A/en not_active Expired
- 1975-06-18 JP JP7423775A patent/JPS543773B2/ja not_active Expired
- 1975-08-14 BE BE159212A patent/BE832441A/xx not_active IP Right Cessation
- 1975-08-21 DE DE2537166A patent/DE2537166C2/de not_active Expired
- 1975-08-21 IT IT2649775A patent/IT1041978B/it active
- 1975-08-22 FR FR7526037A patent/FR2282453A1/fr active Granted
- 1975-08-22 GB GB3496075A patent/GB1513296A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2282453B1 (enExample) | 1979-02-02 |
| US3988286A (en) | 1976-10-26 |
| BE832441A (fr) | 1976-02-16 |
| JPS543773B2 (enExample) | 1979-02-27 |
| DE2537166C2 (de) | 1982-01-21 |
| FR2282453A1 (fr) | 1976-03-19 |
| DE2537166A1 (de) | 1976-03-04 |
| IT1041978B (it) | 1980-01-10 |
| GB1513296A (en) | 1978-06-07 |
| JPS5134997A (enExample) | 1976-03-25 |
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