CA1064193A - Procede pour proteger les groupes reactifs de l'oxyde de polyphenylene - Google Patents

Procede pour proteger les groupes reactifs de l'oxyde de polyphenylene

Info

Publication number: CA1064193A
Authority: CA; Canada
Prior art keywords: polyphenylene oxide; agent; formula; halides; capping
Prior art date: 1974-02-11
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

CA218,298A

Other languages

English (en)

Other versions

CA218298S (en

Inventor

Dwain M. White

Allan S. Hay

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.)

1974-02-11

Filing date

1975-01-21

Publication date

1979-10-09

1975-01-21 Application filed by General Electric Co filed Critical General Electric Co

1979-10-09 Application granted granted Critical

1979-10-09 Publication of CA1064193A publication Critical patent/CA1064193A/fr

Status Expired legal-status Critical Current

Links

239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 67
229920006380 polyphenylene oxide Polymers 0.000 title claims abstract description 60
238000000034 method Methods 0.000 title claims abstract description 38
230000008569 process Effects 0.000 title claims abstract description 33
239000003795 chemical substances by application Substances 0.000 claims abstract description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
239000012071 phase Substances 0.000 claims abstract description 24
238000012546 transfer Methods 0.000 claims abstract description 22
230000003197 catalytic effect Effects 0.000 claims abstract description 19
239000003638 chemical reducing agent Substances 0.000 claims abstract description 17
239000012074 organic phase Substances 0.000 claims abstract description 15
-1 sulfonium ions Chemical class 0.000 claims description 32
239000011541 reaction mixture Substances 0.000 claims description 26
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
239000002585 base Substances 0.000 claims description 23
229920000642 polymer Polymers 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
150000004820 halides Chemical class 0.000 claims description 14
239000000203 mixture Chemical group 0.000 claims description 13
150000008064 anhydrides Chemical class 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 7
150000001350 alkyl halides Chemical class 0.000 claims description 7
150000002763 monocarboxylic acids Chemical class 0.000 claims description 7
150000008050 dialkyl sulfates Chemical class 0.000 claims description 6
150000002989 phenols Chemical class 0.000 claims description 6
239000011347 resin Substances 0.000 claims description 6
229920005989 resin Polymers 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 4
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 4
239000011737 fluorine Chemical group 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
150000002500 ions Chemical class 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
238000005691 oxidative coupling reaction Methods 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
150000003856 quaternary ammonium compounds Chemical group 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 2
150000004026 tertiary sulfonium compounds Chemical class 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
125000005496 phosphonium group Chemical group 0.000 claims 1
229920001955 polyphenylene ether Polymers 0.000 claims 1
230000001590 oxidative effect Effects 0.000 abstract description 9
230000009467 reduction Effects 0.000 abstract description 7
230000015556 catabolic process Effects 0.000 abstract description 6
238000006731 degradation reaction Methods 0.000 abstract description 6
238000004519 manufacturing process Methods 0.000 abstract description 5
238000001125 extrusion Methods 0.000 abstract description 2
238000000465 moulding Methods 0.000 abstract description 2
238000007796 conventional method Methods 0.000 abstract 1
238000007666 vacuum forming Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
238000002835 absorbance Methods 0.000 description 10
239000006227 byproduct Substances 0.000 description 9
238000000926 separation method Methods 0.000 description 7
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000013638 trimer Substances 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
RPNMGUBLKCLAEK-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-n,n-diethylethanamine;hydrochloride Chemical compound [Cl-].CC[NH+](CC)CCSC1=CC=C(Cl)C=C1 RPNMGUBLKCLAEK-UHFFFAOYSA-N 0.000 description 4
DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 4
101100243399 Caenorhabditis elegans pept-2 gene Proteins 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000000539 dimer Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920000265 Polyparaphenylene Polymers 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000470 constituent Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000011067 equilibration Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
QDRFIDSUGRGGAY-UHFFFAOYSA-N 4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C)C(=O)C(C)=CC1=C1C=C(C)C(=O)C(C)=C1 QDRFIDSUGRGGAY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
150000004703 alkoxides Chemical group 0.000 description 2
125000003118 aryl 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
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
229920002852 poly(2,6-dimethyl-1,4-phenylene oxide) polymer Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000010802 sludge Substances 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
238000001429 visible spectrum Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
AFTZDCQOKWGCAB-UHFFFAOYSA-N (1,5-dichlorocyclohexa-2,4-diene-1-carbonyl) 1,5-dichlorocyclohexa-2,4-diene-1-carboxylate Chemical compound C1C(Cl)=CC=CC1(Cl)C(=O)OC(=O)C1(Cl)C=CC=C(Cl)C1 AFTZDCQOKWGCAB-UHFFFAOYSA-N 0.000 description 1
AAMGTDBAQQMXQN-UHFFFAOYSA-N (2,3,4,5,6-pentachlorobenzoyl) 2,3,4,5,6-pentachlorobenzoate Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AAMGTDBAQQMXQN-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 1
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
INVMIQZSRPMKEB-UHFFFAOYSA-L C[N+](C)(C)C.C[N+](C)(C)C.[O-]S(=O)S([O-])=O Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.[O-]S(=O)S([O-])=O INVMIQZSRPMKEB-UHFFFAOYSA-L 0.000 description 1
241000736839 Chara Species 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
241001313099 Pieris napi Species 0.000 description 1
XMZRNPXKKMMLJZ-UHFFFAOYSA-L S(=O)(=O)([O-])S(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(CC)[N+](CCC)(CCC)CCC Chemical compound S(=O)(=O)([O-])S(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(CC)[N+](CCC)(CCC)CCC XMZRNPXKKMMLJZ-UHFFFAOYSA-L 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
FCMYSEXCLRFWBP-UHFFFAOYSA-N [NH4+].[NH4+].[O-]S(=O)S([O-])=O Chemical compound [NH4+].[NH4+].[O-]S(=O)S([O-])=O FCMYSEXCLRFWBP-UHFFFAOYSA-N 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000004054 benzoquinones Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
ZBXIMWWPOCRUNL-UHFFFAOYSA-N bis(3-methylbutyl) sulfate Chemical compound CC(C)CCOS(=O)(=O)OCCC(C)C ZBXIMWWPOCRUNL-UHFFFAOYSA-N 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
DSAJRCNSPOSHPL-UHFFFAOYSA-N didodecyl sulfate Chemical compound CCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCC DSAJRCNSPOSHPL-UHFFFAOYSA-N 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
BNMHIKTUFBWOAM-UHFFFAOYSA-N dioctadecyl sulfate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCCCCCCCC BNMHIKTUFBWOAM-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229940075933 dithionate Drugs 0.000 description 1
AOMUALOCHQKUCD-UHFFFAOYSA-N dodecyl 4-chloro-3-[[3-(4-methoxyphenyl)-3-oxopropanoyl]amino]benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=C(Cl)C(NC(=O)CC(=O)C=2C=CC(OC)=CC=2)=C1 AOMUALOCHQKUCD-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010292 electrical insulation Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IDUWTCGPAPTSFB-UHFFFAOYSA-N hexyl hydrogen sulfate Chemical compound CCCCCCOS(O)(=O)=O IDUWTCGPAPTSFB-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000009413 insulation Methods 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
230000002101 lytic effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
229940102396 methyl bromide Drugs 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
229910052757 nitrogen Inorganic materials 0.000 description 1
WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
150000004010 onium ions Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
229960003903 oxygen Drugs 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000002954 polymerization reaction product Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000011112 process operation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
239000012085 test solution Substances 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1

Classifications

- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
- C08G65/485—Polyphenylene oxides

Landscapes

Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyethers (AREA)

CA218,298A 1974-02-11 1975-01-21 Procede pour proteger les groupes reactifs de l'oxyde de polyphenylene Expired CA1064193A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US44129474A	1974-02-11	1974-02-11

Publications (1)

Publication Number	Publication Date
CA1064193A true CA1064193A (fr)	1979-10-09

Family

ID=23752326

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA218,298A Expired CA1064193A (fr)	1974-02-11	1975-01-21	Procede pour proteger les groupes reactifs de l'oxyde de polyphenylene

Country Status (3)

Country	Link
JP (1)	JPS5921896B2 (fr)
CA (1)	CA1064193A (fr)
DE (1)	DE2505329C2 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4156773A (en) *	1977-05-26	1979-05-29	General Electric Company	Process for capping quinone-coupled polyphenylene oxides
DE3035587A1 (de) *	1980-09-20	1982-05-06	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von polyphenylenaethergruppen enthaltenden polymeren
DE3444099A1 (de) *	1984-12-04	1986-06-05	Basf Ag, 6700 Ludwigshafen	Poly(phenylenether) und verfahren zu ihrer herstellung
US4808671A (en) *	1988-04-21	1989-02-28	General Electric Company	Catalytic method of preparing carboxy derivatives of polyphenylene ethers
CA2013041A1 (fr) *	1989-04-07	1990-10-07	Johannes M. Zijderveld	Procede pour la preparation d'ether modifie de polyphenylene ou de polymeres connexes, et leur utilisation dans des polymeres rigides haute temperature modifies formes de composesaromatiques substitues par des groupes vinyles
AU2003292128A1 (en) *	2002-12-18	2004-07-09	Bsh Bosch Und Siemens Hausgerate Gmbh	Water-bearing domestic appliance comprising a drainage pump and corresponding drainage pump
CN121405834B (zh) *	2025-12-26	2026-04-21	潍坊鑫洋化工有限公司	一种分子量可控的聚苯乙烯的制备方法

1975
- 1975-01-21 CA CA218,298A patent/CA1064193A/fr not_active Expired
- 1975-02-08 DE DE19752505329 patent/DE2505329C2/de not_active Expired
- 1975-02-12 JP JP1696775A patent/JPS5921896B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2505329C2 (de)	1983-08-25
JPS5921896B2 (ja)	1984-05-23
DE2505329A1 (de)	1975-08-14
JPS50110497A (fr)	1975-08-30

Publication	Publication Date	Title
US4048143A (en)	1977-09-13	Process for capping polyphenylene oxide
US3306875A (en)	1967-02-28	Oxidation of phenols and resulting products
US3642699A (en)	1972-02-15	Formation of polyphenylene ethers
US4234706A (en)	1980-11-18	Quinone-coupled polyphenylene oxides
US3838102A (en)	1974-09-24	Removal of metallic catalyst residue from polyphenylene ethers
EP1307500B1 (fr)	2006-03-22	Preparation de resines de poly(arylene ether) de viscosite intrinseque elevee
US4098846A (en)	1978-07-04	Polyphenylene oxide polystyrene product-by-process
US3956242A (en)	1976-05-11	Preparation of polyphenylene oxide using a manganese (II) ω-hydroxyoxime chelate reaction promoter
US3384619A (en)	1968-05-21	Process for manufacture of polyphenylene ethers
CA1064193A (fr)	1979-10-09	Procede pour proteger les groupes reactifs de l'oxyde de polyphenylene
US3432469A (en)	1969-03-11	Process for producing high molecular weight polymers from impure 2,6-xylenol
US3875256A (en)	1975-04-01	Bis(polyphenylene)-carbonate block copolymers
US4140675A (en)	1979-02-20	Process of forming quinone-coupled polyphenylene oxides
US4743661A (en)	1988-05-10	Poly (phenylene ethers) and their preparation
US4537948A (en)	1985-08-27	Process for the production of polyphenylene oxides
US5214128A (en)	1993-05-25	Method for purifying a polyphenylene ether with amino carboxylic acid derivative
US3234183A (en)	1966-02-08	Process for preparing poly
US4260733A (en)	1981-04-07	Method for making aromatic polyformals
US4536567A (en)	1985-08-20	Removal of the catalyst from polyphenylene ethers
US4097458A (en)	1978-06-27	Method for preparing polyphenylene ethers
US4088634A (en)	1978-05-09	Process for isolation and purification of polyphenylene ethers
US3546170A (en)	1970-12-08	Stabilized methylthio and methylthiomethylene substituted poly(phenylene oxide) copolymers
US4136087A (en)	1979-01-23	Method for making aromatic cyclic polyformals
US3962180A (en)	1976-06-08	Process for polymerizing phenols to produce polyphenylene oxides of low molecular weight
EP0153074A2 (fr)	1985-08-28	Procédé de préparation de poly(oxydes de phénylène)