GB1105948A - Poly-dihalophenylene ethers - Google Patents
Poly-dihalophenylene ethersInfo
- Publication number
- GB1105948A GB1105948A GB4083665A GB4083665A GB1105948A GB 1105948 A GB1105948 A GB 1105948A GB 4083665 A GB4083665 A GB 4083665A GB 4083665 A GB4083665 A GB 4083665A GB 1105948 A GB1105948 A GB 1105948A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- bromine
- iodine
- chlorine
- tetramethyl
- Prior art date
- 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
Links
- 150000002170 ethers Chemical class 0.000 title abstract 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- -1 aromatic heterocyclic amine Chemical class 0.000 abstract 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 3
- 229940045803 cuprous chloride Drugs 0.000 abstract 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 abstract 2
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 abstract 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 abstract 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- KGURSDWHGSLAPP-UHFFFAOYSA-N 4-bromo-2,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(Br)C=C1Cl KGURSDWHGSLAPP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940043279 diisopropylamine Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 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
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/44—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols by oxidation of phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Poly-(2,6-dihalophenylene) ethers containing <FORM:1105948/C3/1> and <FORM:1105948/C3/2> where each X1 is iodine, bromine or chlorine, R1 and R11 are iodine, bromine, chlorine or a branching 2,6-disubstituted-1-phenoxy radical, at least one of R1 and R11 being said phenoxy radical, and n1 and n2 are integers, the ratio of n2 to the sum of n1 + n2 being greater than 0 and less than 0.25. The polymers are prepared by polymerizing in solution a halophenol of formula <FORM:1105948/C3/3> where each X1 is iodine, bromine or chlorine and X is the same as X1 or is hydrogen, in the presence of oxygen and a catalytically active complex of a secondary or tertiary amine and a basic cupric salt, at a temperature not greater than 120 DEG C. or not greater than 80 DEG C. when X is halogen and the amine is an aromatic heterocyclic amine. The polymerization may include from 0 to 99 mole per cent of a second phenol of formula <FORM:1105948/C3/4> where Q is a hydrocarbon radical, a halohydrocarbon radical, a hydrocarbonoxy radical or a halohydrocarbonoxy radical, Q1 and Q11 are each the same as Q or are hydrogen, and X is hydrogen, iodine, bromine or chlorine. In Examples polymers are obtained from 2,6-dichlorophenol, 2,4,6 - trichlorophenol, 2,6 - dichloro - 4 - bromophenol, a mixture of 2,6 - dichlorophenol and 2,6 - dimethylphenol, and mixtures of 2,4,6-trichlorophenol and 2,6-dimethylphenol; the catalysts are obtained from cuprous chloride and N,N,N1,N1-tetramethyl - 1,3 - butanediamine, from cuprous chloride and N,N,N1,N1 - tetramethyl - 1,3 - propanediamine, from cuprous bromide and N,N,N1,N1 - tetramethyl - 1,3 - propanediamine, from cuprous chloride and N-methylmorpholine and from cuprous bromide and diisopropylamine. Other suitable materials for use in the process are mentioned.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39932564A | 1964-09-25 | 1964-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1105948A true GB1105948A (en) | 1968-03-13 |
Family
ID=23579116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4083665A Expired GB1105948A (en) | 1964-09-25 | 1965-09-24 | Poly-dihalophenylene ethers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1570699B2 (en) |
| GB (1) | GB1105948A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0071081A1 (en) * | 1981-07-23 | 1983-02-09 | BASF Aktiengesellschaft | Process for the preparation of polyphenylene ethers |
| EP0084896A3 (en) * | 1982-01-20 | 1983-08-10 | General Electric Company | Catalyst for the oxidative coupling of organic compounds and method |
-
1965
- 1965-09-23 DE DE19651570699 patent/DE1570699B2/en not_active Withdrawn
- 1965-09-24 GB GB4083665A patent/GB1105948A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0071081A1 (en) * | 1981-07-23 | 1983-02-09 | BASF Aktiengesellschaft | Process for the preparation of polyphenylene ethers |
| EP0084896A3 (en) * | 1982-01-20 | 1983-08-10 | General Electric Company | Catalyst for the oxidative coupling of organic compounds and method |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1570699A1 (en) | 1970-04-02 |
| DE1570699B2 (en) | 1972-01-27 |
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