CA1116637A - Oxydes de polyphenylene couples a la quinone - Google Patents

Oxydes de polyphenylene couples a la quinone

Info

Publication number: CA1116637A
Authority: CA; Canada
Prior art keywords: quinone; polymer; reaction; radical; equal
Prior art date: 1978-08-18
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

Application number

CA000309632A

Other languages

English (en)

Inventor

Dwain M. White

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.)

General Electric Co

Original Assignee

General Electric Co

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.)

1978-08-18

Filing date

1978-08-18

Publication date

1982-01-19

1978-08-18 Application filed by General Electric Co filed Critical General Electric Co

1978-08-18 Priority to CA000309632A priority Critical patent/CA1116637A/fr

1982-01-19 Application granted granted Critical

1982-01-19 Publication of CA1116637A publication Critical patent/CA1116637A/fr

Status Expired legal-status Critical Current

Links

AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title claims abstract description 105
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 45
229920006380 polyphenylene oxide Polymers 0.000 title claims abstract description 40
-1 arene radical Chemical class 0.000 claims description 22
150000002989 phenols Chemical class 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
125000004151 quinonyl group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 7
229920000642 polymer Polymers 0.000 abstract description 47
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 17
239000000376 reactant Substances 0.000 abstract description 8
239000000203 mixture Substances 0.000 abstract description 6
239000011347 resin Substances 0.000 abstract description 3
229920005989 resin Polymers 0.000 abstract description 3
230000000704 physical effect Effects 0.000 abstract description 2
239000000126 substance Substances 0.000 abstract description 2
229920001169 thermoplastic Polymers 0.000 abstract description 2
239000004416 thermosoftening plastic Substances 0.000 abstract description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 29
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 26
239000003054 catalyst Substances 0.000 description 21
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
238000005859 coupling reaction Methods 0.000 description 15
230000008878 coupling Effects 0.000 description 14
238000010168 coupling process Methods 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
239000001301 oxygen Substances 0.000 description 12
229910052760 oxygen Inorganic materials 0.000 description 12
239000007795 chemical reaction product Substances 0.000 description 10
238000002835 absorbance Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
230000009849 deactivation Effects 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
238000010094 polymer processing Methods 0.000 description 6
229920002852 poly(2,6-dimethyl-1,4-phenylene oxide) polymer Polymers 0.000 description 5
230000008569 process Effects 0.000 description 5
150000004053 quinones Chemical class 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241000894007 species Species 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
238000002955 isolation Methods 0.000 description 4
238000005691 oxidative coupling reaction Methods 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000000178 monomer Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229960003280 cupric chloride Drugs 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
238000011067 equilibration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
WAKHLWOJMHVUJC-FYWRMAATSA-N (2e)-2-hydroxyimino-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(=N/O)\C(O)C1=CC=CC=C1 WAKHLWOJMHVUJC-FYWRMAATSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
101100137177 Drosophila melanogaster polyph gene Proteins 0.000 description 1
QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910021380 Manganese Chloride Inorganic materials 0.000 description 1
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
241001024304 Mino Species 0.000 description 1
239000004727 Noryl Substances 0.000 description 1
229920001207 Noryl Polymers 0.000 description 1
101000941926 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Carboxypeptidase Y inhibitor Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
WAKHLWOJMHVUJC-UHFFFAOYSA-N benzoin alpha-oxime Natural products C=1C=CC=CC=1C(=NO)C(O)C1=CC=CC=C1 WAKHLWOJMHVUJC-UHFFFAOYSA-N 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
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
229940112669 cuprous oxide Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229920005669 high impact polystyrene Polymers 0.000 description 1
239000004797 high-impact polystyrene Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000011565 manganese chloride Substances 0.000 description 1
229940099607 manganese chloride Drugs 0.000 description 1
235000002867 manganese chloride Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920013637 polyphenylene oxide polymer Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Polyethers (AREA)

CA000309632A 1978-08-18 1978-08-18 Oxydes de polyphenylene couples a la quinone Expired CA1116637A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000309632A CA1116637A (fr)	1978-08-18	1978-08-18	Oxydes de polyphenylene couples a la quinone

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000309632A CA1116637A (fr)	1978-08-18	1978-08-18	Oxydes de polyphenylene couples a la quinone

Publications (1)

Publication Number	Publication Date
CA1116637A true CA1116637A (fr)	1982-01-19

Family

ID=4112152

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000309632A Expired CA1116637A (fr)	1978-08-18	1978-08-18	Oxydes de polyphenylene couples a la quinone

Country Status (1)

Country	Link
CA (1)	CA1116637A (fr)

1978
- 1978-08-18 CA CA000309632A patent/CA1116637A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-01-19	MKEX	Expiry

Publication	Publication Date	Title
US4234706A (en)	1980-11-18	Quinone-coupled polyphenylene oxides
EP1307500B1 (fr)	2006-03-22	Preparation de resines de poly(arylene ether) de viscosite intrinseque elevee
US3838102A (en)	1974-09-24	Removal of metallic catalyst residue from polyphenylene ethers
US4048143A (en)	1977-09-13	Process for capping polyphenylene oxide
CA1278145C (fr)	1990-12-18	Ethers de type polyphenylene, stabilises par reaction a chaud des extremites, et leur methode de preparation
US4140675A (en)	1979-02-20	Process of forming quinone-coupled polyphenylene oxides
US4116939A (en)	1978-09-26	Intrinsic viscosity control of polyphenylene ether reaction mixtures
US3642699A (en)	1972-02-15	Formation of polyphenylene ethers
CA1204453A (fr)	1986-05-13	Methode de production d'ethers de polyphenylene bifonction
EP0334026A1 (fr)	1989-09-27	Procédé de coiffage de poly(éthers de phénylène)
US5693742A (en)	1997-12-02	Solventless method for making polyarylene ethers
JP2003012796A (ja)	2003-01-15	２官能性フェニレンエーテルのオリゴマー体とその製造法
US4743661A (en)	1988-05-10	Poly (phenylene ethers) and their preparation
CA1116637A (fr)	1982-01-19	Oxydes de polyphenylene couples a la quinone
EP0153074A2 (fr)	1985-08-28	Procédé de préparation de poly(oxydes de phénylène)
US4088634A (en)	1978-05-09	Process for isolation and purification of polyphenylene ethers
US4097458A (en)	1978-06-27	Method for preparing polyphenylene ethers
JPS6349705B2 (fr)	1988-10-05
US4097459A (en)	1978-06-27	Method for preparing polyphenylene ethers
US5629405A (en)	1997-05-13	Method for making polyarylene ethers with pyridine catalysts
US4169114A (en)	1979-09-25	Process for improving the color of resinous compositions
EP0594249A2 (fr)	1994-04-27	Procédé pour la préparation de polyéthers de phénylène ayant un contenu faible de particules fines
JPS61130340A (ja)	1986-06-18	ポリフェニレンエーテルの製造方法
EP0113430B1 (fr)	1987-01-28	Résines de poly(éthers de phénylènes) de poids moléculaire contrôlé et procédé de leur préparation
JPH0523291B2 (fr)	1993-04-02