CA1297607C - Melanges miscibles de poly (aryloxysulfones) - Google Patents

Melanges miscibles de poly (aryloxysulfones)

Info

Publication number: CA1297607C
Authority: CA; Canada
Prior art keywords: polymers; aryl ether; poly; pae; polymer
Prior art date: 1985-08-19
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 - Lifetime

Application number

CA000515860A

Other languages

English (en)

Inventor

Lloyd Mahlon Robeson

James Elmer Harris

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BP Corp North America Inc

Original Assignee

BP Corp North America Inc

Priority date (The priority date 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 date listed.)

1985-08-19

Filing date

1986-08-13

Publication date

1992-03-17

1986-08-13 Application filed by BP Corp North America Inc filed Critical BP Corp North America Inc

1992-03-17 Application granted granted Critical

1992-03-17 Publication of CA1297607C publication Critical patent/CA1297607C/fr

2009-03-17 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 116
-1 poly(aryl ether sulfones Chemical class 0.000 title claims abstract description 28
229920000642 polymer Polymers 0.000 claims description 86
229920000110 poly(aryl ether sulfone) Polymers 0.000 claims description 27
230000003301 hydrolyzing effect Effects 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 3
239000000758 substrate Substances 0.000 abstract description 3
230000009477 glass transition Effects 0.000 description 30
239000002904 solvent Substances 0.000 description 16
238000000034 method Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
150000008378 aryl ethers Chemical class 0.000 description 9
230000007704 transition Effects 0.000 description 9
229920002959 polymer blend Polymers 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000011521 glass Substances 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000002156 mixing Methods 0.000 description 6
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 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 4
230000002596 correlated effect Effects 0.000 description 4
230000003993 interaction Effects 0.000 description 4
229920000090 poly(aryl ether) Polymers 0.000 description 4
239000000243 solution Substances 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000006835 compression Effects 0.000 description 3
238000007906 compression Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
229920002521 macromolecule Polymers 0.000 description 3
239000003880 polar aprotic solvent Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
229920003232 aliphatic polyester Polymers 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000000463 material Substances 0.000 description 2
229920005623 miscible polymer blend Polymers 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
LFASIQLVFCSCCU-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 LFASIQLVFCSCCU-UHFFFAOYSA-N 0.000 description 1
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001442654 Percnon planissimum Species 0.000 description 1
206010035148 Plague Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
229920005622 compatible polymer blend Polymers 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000011557 critical solution Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
238000009863 impact test Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000012764 mineral filler Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012783 reinforcing fiber Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical class O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
239000010456 wollastonite Substances 0.000 description 1
229910052882 wollastonite Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

CA000515860A 1985-08-19 1986-08-13 Melanges miscibles de poly (aryloxysulfones) Expired - Lifetime CA1297607C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US76669285A	1985-08-19	1985-08-19
JP766,692		1985-08-19
US88789486A	1986-07-28	1986-07-28
JP887,894		1986-07-28

Publications (1)

Publication Number	Publication Date
CA1297607C true CA1297607C (fr)	1992-03-17

Family

ID=27117785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000515860A Expired - Lifetime CA1297607C (fr)	1985-08-19	1986-08-13	Melanges miscibles de poly (aryloxysulfones)

Country Status (1)

Country	Link
CA (1)	CA1297607C (fr)

1986
- 1986-08-13 CA CA000515860A patent/CA1297607C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1994-09-17	MKLA	Lapsed

Publication	Publication Date	Title
EP0176988B1 (fr)	1992-12-02	Corps moulé à partir d'un mélange d'une poly(aryléther-cétone) et d'une poly(aryléther-sulfone)
AU571592B2 (en)	1988-04-21	Blends of poly(aryl ketones)
US4849503A (en)	1989-07-18	Novel poly(aryl ethers)
KR920000175B1 (ko)	1992-01-09	중합체 조성물
EP0176989B1 (fr)	1989-04-19	Articles moulés préparés à partir de mélanges d'une poly(aryléther-sulfone) contenant des groupes biphényle et d'une poly(aryléther-cétone)
CA1218782A (fr)	1987-03-03	Melanges au polyarylethersufone
EP0062830B1 (fr)	1985-12-27	Alliages d'un poly(sulfure d'arylène) et d'un poly(arylcétone)
EP0376349A2 (fr)	1990-07-04	Compositions miscibles de polymères contenant des groupements imides et des polyarylènesulfones
EP0215580A2 (fr)	1987-03-25	Mélanges miscibles de poly(aryléthersulfones)
US4957978A (en)	1990-09-18	Poly(aryl ether sulfone) compositions having improved flow properties
US4550140A (en)	1985-10-29	Circuit board substrates prepared from poly(aryl ethers)s
US4804723A (en)	1989-02-14	Miscible blends of poly(aryl ether sulfones)
CA1297607C (fr)	1992-03-17	Melanges miscibles de poly (aryloxysulfones)
JPS6134068A (ja)	1986-02-18	成形電気装置
JP3173006B2 (ja)	2001-06-04	樹脂組成物
EP0257150B1 (fr)	1992-03-25	Mélanges miscibles d'une poly(aryléther)cétone et d'un polyimide
US5134202A (en)	1992-07-28	Process for miscible blends of imide containing polymers with poly(aryl sulfones)
US4963627A (en)	1990-10-16	Injection moldable blends of poly(etherketones) and polyamide-imides
JPH0611863B2 (ja)	1994-02-16	ポリフェニレンスルフィド系樹脂組成物
US4814419A (en)	1989-03-21	Polyarylether sulfones useful for molding into a circuit board substrate
JPH04130158A (ja)	1992-05-01	樹脂組成物
US4816505A (en)	1989-03-28	New polyarylethersulfone circuit board substrates
US5001200A (en)	1991-03-19	Poly(phenylene oxide)-poly(aryl ether ketone) blends
JPH02155951A (ja)	1990-06-15	ポリフェニレンスルフィド樹脂組成物
JPS62121762A (ja)	1987-06-03	ポリ（アリ−ルエ−テルスルホン）の混和性ブレンド