CA1128686A - Polymeres phosphores sequences d'oxyde de polyphenylene - Google Patents

Polymeres phosphores sequences d'oxyde de polyphenylene

Info

Publication number: CA1128686A
Authority: CA; Canada
Prior art keywords: radicals; phosphoryl; radical; polymer; coupled
Prior art date: 1978-07-20
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

CA307,820A

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.)

1978-07-20

Filing date

1978-07-20

Publication date

1982-07-27

1978-07-20 Application filed by General Electric Co filed Critical General Electric Co

1978-07-20 Priority to CA307,820A priority Critical patent/CA1128686A/fr

1982-07-27 Application granted granted Critical

1982-07-27 Publication of CA1128686A publication Critical patent/CA1128686A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 74
239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 34
229920006380 polyphenylene oxide Polymers 0.000 title claims abstract description 30
229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 28
239000011574 phosphorus Substances 0.000 title claims abstract description 28
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 27
-1 polyphenylene Polymers 0.000 claims abstract description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 10
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 36
238000005859 coupling reaction Methods 0.000 claims description 13
150000004820 halides Chemical class 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000004151 quinonyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
150000003254 radicals Chemical class 0.000 claims 2
150000002430 hydrocarbons Chemical class 0.000 claims 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 3
239000003063 flame retardant Substances 0.000 abstract description 3
229920000265 Polyparaphenylene Polymers 0.000 abstract description 2
238000004519 manufacturing process 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 24
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000002955 isolation Methods 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
238000002835 absorbance Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
238000000034 method Methods 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
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 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 4
229920005669 high impact polystyrene Polymers 0.000 description 4
239000004797 high-impact polystyrene Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
101001120868 Homo sapiens Meckel syndrome type 1 protein Proteins 0.000 description 3
102100026048 Meckel syndrome type 1 protein Human genes 0.000 description 3
229920001207 Noryl Polymers 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000002243 precursor Substances 0.000 description 3
JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 2
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
239000004727 Noryl Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000010949 copper Substances 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920013637 polyphenylene oxide polymer Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 description 1
102100027446 Acetylserotonin O-methyltransferase Human genes 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
101000936718 Homo sapiens Acetylserotonin O-methyltransferase Proteins 0.000 description 1
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 1
238000007696 Kjeldahl method Methods 0.000 description 1
WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
229910019213 POCl3 Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
QVMHUALAQYRRBM-UHFFFAOYSA-N [P].[P] Chemical compound [P].[P] QVMHUALAQYRRBM-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
239000008346 aqueous phase Substances 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
230000009286 beneficial effect Effects 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
229920001400 block copolymer Polymers 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
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
239000012612 commercial material Substances 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
229940112669 cuprous oxide Drugs 0.000 description 1
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000003106 haloaryl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 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
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
238000009864 tensile test Methods 0.000 description 1
150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1

Landscapes

Polyethers (AREA)

CA307,820A 1978-07-20 1978-07-20 Polymeres phosphores sequences d'oxyde de polyphenylene Expired CA1128686A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA307,820A CA1128686A (fr)	1978-07-20	1978-07-20	Polymeres phosphores sequences d'oxyde de polyphenylene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA307,820A CA1128686A (fr)	1978-07-20	1978-07-20	Polymeres phosphores sequences d'oxyde de polyphenylene

Publications (1)

Publication Number	Publication Date
CA1128686A true CA1128686A (fr)	1982-07-27

Family

ID=4111936

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,820A Expired CA1128686A (fr)	1978-07-20	1978-07-20	Polymeres phosphores sequences d'oxyde de polyphenylene

Country Status (1)

Country	Link
CA (1)	CA1128686A (fr)

1978
- 1978-07-20 CA CA307,820A patent/CA1128686A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-07-27	MKEX	Expiry

Publication	Publication Date	Title
US3642699A (en)	1972-02-15	Formation of polyphenylene ethers
US5204438A (en)	1993-04-20	Silicone macromers and thermoplastic flame retardant silicone-polyphenylene ether graft copolymers obtained therefrom
US3883451A (en)	1975-05-13	Flame-retardant poly (aryloxyphosphazene) copolymers
US3318959A (en)	1967-05-09	Symmetrically terminated polyphenylene ether
US3639656A (en)	1972-02-01	Formation of polyphenylene ethers
GB1599474A (en)	1981-10-07	Quinone-coupled polyphenylene oxides
EP0405139B1 (fr)	1993-12-29	Procédé de préparation de poly(éthers de phénylène)coiffés par un groupement aryloxytriazine
US4840982A (en)	1989-06-20	Polymer blends containing ionomeric elastomers
US4588806A (en)	1986-05-13	Polyphenylene ether resins having bimodal molecular weight distributions and method of their formation
US4156699A (en)	1979-05-29	Phosphorus containing block polymers of polyphenylene oxide
GB1599472A (en)	1981-10-07	Process of forming quinone-coupled polyphenylene oxides
EP0433746B1 (fr)	1995-03-22	Copolymères greffés thermoplastiques, retardateur de flamme et ayant des segments polysiloxanes et polyphénylène éther
CA1128686A (fr)	1982-07-27	Polymeres phosphores sequences d'oxyde de polyphenylene
CA1279419C (fr)	1991-01-22	Copolymeres de type ether polyphenylenique-polycarbonate et methode pour leur preparation
CA1285091C (fr)	1991-06-18	Melanges comprenant des ethers et des lactames polyphenyleniques et compositions resineuses preparees a partir de ceux-ci
US4154771A (en)	1979-05-15	Process of forming phosphorus containing block polymers of polyphenylene oxide
US5068286A (en)	1991-11-26	Copolymers from nucleophilic olefin polymers and epoxytriazine-capped polyphenylene ethers
US4156770A (en)	1979-05-29	Acyl coupled polymers of quinone-coupled polyphenylene oxides
EP0304621B1 (fr)	1993-01-13	Procédé pour la préparation de copolymères greffés phénylène-éther-amide
US5115043A (en)	1992-05-19	Process for functionalizing polyphenylene ether with substituted chlorotriazine
EP0386544B1 (fr)	1995-01-18	Polyphénylèneéthers modifiés par des groupements terminaux aryloxytriazine et procédé pour leur préparation
EP0147724A2 (fr)	1985-07-10	Composés alcényl-aromatiques résistant à la flamme et polymères contenant du phosphore lié chimiquement et compositions avec des polyphènyléne ethers
US4334050A (en)	1982-06-08	Arene polysulfonyl halide coupled block polymers of polyphenylene oxide and aromatic polyformals
US3787362A (en)	1974-01-22	Preparation of polyphenylene ethers with dialkylformamide promoted copper-amine catalysts
US4158728A (en)	1979-06-19	Heterocyclic-coupled polymers of polyphenylene oxides