CA1106540A - Procede d'obtention d'ethers de polyphenylene - Google Patents

Procede d'obtention d'ethers de polyphenylene

Info

Publication number: CA1106540A
Authority: CA; Canada
Prior art keywords: amine; catalyst; polyphenylene ether; resin; carbon atoms
Prior art date: 1977-09-08
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

CA286,285A

Other languages

English (en)

Inventor

Glenn D. Cooper

James G. Bennett, Jr.

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.)

1977-09-08

Filing date

1977-09-08

Publication date

1981-08-04

1977-09-08 Application filed by General Electric Co filed Critical General Electric Co

1977-09-08 Priority to CA286,285A priority Critical patent/CA1106540A/fr

1981-08-04 Application granted granted Critical

1981-08-04 Publication of CA1106540A publication Critical patent/CA1106540A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 27
239000003054 catalyst Substances 0.000 claims abstract description 39
-1 cycloalkylene diamine Chemical class 0.000 claims abstract description 24
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 14
201000006747 infectious mononucleosis Diseases 0.000 claims abstract description 13
150000002989 phenols Chemical class 0.000 claims abstract description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
239000005749 Copper compound Substances 0.000 claims abstract description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
150000001880 copper compounds Chemical class 0.000 claims abstract description 10
150000003512 tertiary amines Chemical class 0.000 claims abstract description 9
238000005691 oxidative coupling reaction Methods 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
229920005989 resin Polymers 0.000 claims description 35
239000011347 resin Substances 0.000 claims description 35
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 28
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 18
238000006116 polymerization reaction Methods 0.000 claims description 18
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical group CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
150000003335 secondary amines Chemical class 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 10
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical group CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 5
150000004985 diamines Chemical class 0.000 claims description 5
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical group CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 4
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical class OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
230000006872 improvement Effects 0.000 claims description 4
KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
WRDBAMRVJWQPMU-UHFFFAOYSA-N BrC1=CC(C(C=C1)(C)O)C Chemical compound BrC1=CC(C(C=C1)(C)O)C WRDBAMRVJWQPMU-UHFFFAOYSA-N 0.000 claims description 3
229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 3
229910001513 alkali metal bromide Inorganic materials 0.000 claims description 3
229910001616 alkaline earth metal bromide Inorganic materials 0.000 claims description 3
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 3
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
HJTDPDQRTRMIGM-UHFFFAOYSA-N 5-bromo-1,6-dimethylcyclohexa-2,4-dien-1-ol Chemical compound BrC=1C(C(C=CC1)(C)O)C HJTDPDQRTRMIGM-UHFFFAOYSA-N 0.000 claims 1
125000002993 cycloalkylene group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
125000001424 substituent group Chemical group 0.000 abstract description 4
150000004699 copper complex Chemical class 0.000 abstract description 2
230000008878 coupling Effects 0.000 abstract description 2
238000010168 coupling process Methods 0.000 abstract description 2
238000005859 coupling reaction Methods 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
229920000642 polymer Polymers 0.000 description 17
239000000243 solution Substances 0.000 description 15
229920001971 elastomer Polymers 0.000 description 11
239000005060 rubber Substances 0.000 description 11
150000001412 amines Chemical class 0.000 description 9
229910052802 copper Inorganic materials 0.000 description 9
239000010949 copper Substances 0.000 description 9
150000003739 xylenols Chemical class 0.000 description 9
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000004793 Polystyrene Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
229920002223 polystyrene Polymers 0.000 description 6
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 5
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 5
229940112669 cuprous oxide Drugs 0.000 description 5
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
229920000265 Polyparaphenylene Polymers 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000005083 Zinc sulfide Substances 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
229940040544 bromides Drugs 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000002738 chelating agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229940116318 copper carbonate Drugs 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
229910000009 copper(II) carbonate Inorganic materials 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
239000011646 cupric carbonate Substances 0.000 description 2
235000019854 cupric carbonate Nutrition 0.000 description 2
229960003280 cupric chloride Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001183 hydrocarbyl group Chemical group 0.000 description 2
238000000465 moulding Methods 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000008188 pellet Substances 0.000 description 2
229920006380 polyphenylene oxide Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
229910052984 zinc sulfide Inorganic materials 0.000 description 2
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 2
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
UYWLQEPMPVDASH-UHFFFAOYSA-N 2,2,5,5-tetramethylhex-3-ene Chemical group CC(C)(C)C=CC(C)(C)C UYWLQEPMPVDASH-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-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
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
JHPYSMMFWIRBGX-UHFFFAOYSA-L BrC1=CC(C(C=C1)(C)O)C.[Cu](Br)Br Chemical compound BrC1=CC(C(C=C1)(C)O)C.[Cu](Br)Br JHPYSMMFWIRBGX-UHFFFAOYSA-L 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000002174 Styrene-butadiene Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012296 anti-solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-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
229920005549 butyl rubber Polymers 0.000 description 1
229910001622 calcium bromide Inorganic materials 0.000 description 1
WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000009833 condensation Methods 0.000 description 1
239000013068 control sample Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
229940076286 cupric acetate Drugs 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
ZMMDPCMYTCRWFF-UHFFFAOYSA-J dicopper;carbonate;dihydroxide Chemical compound [OH-].[OH-].[Cu+2].[Cu+2].[O-]C([O-])=O ZMMDPCMYTCRWFF-UHFFFAOYSA-J 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
229920005558 epichlorohydrin rubber Polymers 0.000 description 1
229940012017 ethylenediamine Drugs 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920005669 high impact polystyrene Polymers 0.000 description 1
239000004797 high-impact polystyrene Substances 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 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
MFIGJRRHGZYPDD-UHFFFAOYSA-N n,n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)NCCNC(C)C MFIGJRRHGZYPDD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
229920003225 polyurethane elastomer Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011115 styrene butadiene Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229960005196 titanium dioxide Drugs 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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Polyethers (AREA)

CA286,285A 1977-09-08 1977-09-08 Procede d'obtention d'ethers de polyphenylene Expired CA1106540A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA286,285A CA1106540A (fr)	1977-09-08	1977-09-08	Procede d'obtention d'ethers de polyphenylene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA286,285A CA1106540A (fr)	1977-09-08	1977-09-08	Procede d'obtention d'ethers de polyphenylene

Publications (1)

Publication Number	Publication Date
CA1106540A true CA1106540A (fr)	1981-08-04

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ID=4109480

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Application Number	Title	Priority Date	Filing Date
CA286,285A Expired CA1106540A (fr)	1977-09-08	1977-09-08	Procede d'obtention d'ethers de polyphenylene

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CA (1)	CA1106540A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119192558A (zh) *	2024-10-08	2024-12-27	万华化学集团股份有限公司	一种聚亚苯基醚树脂、组合物及其制备方法和用途

1977
- 1977-09-08 CA CA286,285A patent/CA1106540A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN119192558A (zh) *	2024-10-08	2024-12-27	万华化学集团股份有限公司	一种聚亚苯基醚树脂、组合物及其制备方法和用途

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Date	Code	Title	Description
1998-08-04	MKEX	Expiry

Publication	Publication Date	Title
US4092294A (en)	1978-05-30	Method for preparing polyphenylene ethers
US3639656A (en)	1972-02-01	Formation of polyphenylene ethers
US4098846A (en)	1978-07-04	Polyphenylene oxide polystyrene product-by-process
US4028341A (en)	1977-06-07	Process for the preparation of polyphenylene oxides with hydrolytically stable copper catalysts
US6472499B1 (en)	2002-10-29	Preparation of high intrinsic viscosity poly(arylene ether) resins
DE2738889A1 (de)	1978-03-02	Verfahren zur herstellung von polyphenylenaetherharz
GB1559713A (en)	1980-01-23	Molecular weight control of polyphenylene ethers
US4083828A (en)	1978-04-11	Preparation of polyphenylene oxides by the oxidative coupling of a phenolic monomer in the presence of a manganese salt, base and a secondary amine
KR910005346B1 (ko)	1991-07-25	폴리페닐렌에테르의 제조방법
US5068310A (en)	1991-11-26	Polyphenylene ether process, catalyst and resin composition
US4207406A (en)	1980-06-10	Process for preparing polyphenylene oxide copolymers
US4059568A (en)	1977-11-22	Method for the control of diamine catalyzed polyphenylene ether polymerization
US4039510A (en)	1977-08-02	Removal of catalyst from polyphenylene oxide reaction mixtures with nitrogenous salts of nitrilotriacetic acid
US3749693A (en)	1973-07-31	Process for the preparation of polyphenylene ethers and compositions containing the same
US3900445A (en)	1975-08-19	Process for the preparation of polyphenylene ethers with cuprous and cupric amine catalyst
CA1106540A (fr)	1981-08-04	Procede d'obtention d'ethers de polyphenylene
EP0107655B1 (fr)	1986-12-17	Copolymeres sequences de poly(oxyphenylenes) et de polyformals de diphenols non encombres steriquement
US4196278A (en)	1980-04-01	Method for the controlled polymerization of polyphenylene oxide polymers
EP0059958B1 (fr)	1986-06-04	Procédé de préparation d'oxydes de polyphénylène
US4184034A (en)	1980-01-15	Manganese benzoin-imine catalysts and process of preparing polyphenylene ethers using said compounds as catalysts
US4156699A (en)	1979-05-29	Phosphorus containing block polymers of polyphenylene oxide
US3796689A (en)	1974-03-12	Preparation of polyphenylene ethers with dialkyl sulfoxide promoted copper-amine catalysts
EP0183567B1 (fr)	1989-03-29	Procédé de préparation de poly(éther de phénylène)
US4093597A (en)	1978-06-06	Polymerization of 2,6-di-substituted phenols
US3787362A (en)	1974-01-22	Preparation of polyphenylene ethers with dialkylformamide promoted copper-amine catalysts

CA1106540A - Procede d'obtention d'ethers de polyphenylene - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4109480

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Country Status (1)

Cited By (1)

Cited By (1)

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