GB1117327A - Poly-(phenylene oxides) - Google Patents
Poly-(phenylene oxides)Info
- Publication number
- GB1117327A GB1117327A GB3424465A GB3424465A GB1117327A GB 1117327 A GB1117327 A GB 1117327A GB 3424465 A GB3424465 A GB 3424465A GB 3424465 A GB3424465 A GB 3424465A GB 1117327 A GB1117327 A GB 1117327A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polymer
- oxide units
- chlorophenol
- pyridine
- percent
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 8
- 229920000642 polymer Polymers 0.000 abstract 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 abstract 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical class OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 2
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 2
- STKABCXUOJGYOX-UHFFFAOYSA-N (2-chloro-6-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 STKABCXUOJGYOX-UHFFFAOYSA-N 0.000 abstract 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract 1
- GPSJRNOWAMVPDT-UHFFFAOYSA-N 2-(benzenesulfonyl)-4-chlorophenol Chemical class ClC1=CC(=C(C=C1)O)S(=O)(=O)C1=CC=CC=C1 GPSJRNOWAMVPDT-UHFFFAOYSA-N 0.000 abstract 1
- BZWMYDJJDBFAPE-UHFFFAOYSA-N 2-chloro-4-phenylphenol Chemical class C1=C(Cl)C(O)=CC=C1C1=CC=CC=C1 BZWMYDJJDBFAPE-UHFFFAOYSA-N 0.000 abstract 1
- XBILVINOJVKEHG-UHFFFAOYSA-N 2-chloro-6-phenylphenol Chemical class OC1=C(Cl)C=CC=C1C1=CC=CC=C1 XBILVINOJVKEHG-UHFFFAOYSA-N 0.000 abstract 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical class OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 239000000919 ceramic Substances 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 229920013637 polyphenylene oxide polymer Polymers 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- -1 potassium ferricyanide Chemical compound 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 238000002411 thermogravimetry Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 230000004580 weight loss Effects 0.000 abstract 1
- 239000008096 xylene Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
The invention comprises amorphous poly-(phenylene oxides) containing from 0 to 75 mole per cent para-phenylene oxide units with the remainder being ortho-phenylene oxide units, in which up to 30% of the units may carry the side groups phenyl, carbonylaryl or sulphonylaryl, the polymer having a softening range below 150 DEG C., an inherent viscosity measured as a 1% solution of polymer in sulphuric acid of at least 0.3, complete solubility in benzene at 25 DEG C., and a temperature of at least 500 DEG C. for a 10% weight loss in air, as determined by Thermogravimetric Analysis at a rate of temperature rise of 5 DEG C. per minute. The polymers are prepared from very pure potassium o- and p-chlorophenolates containing not more than 0.05% of water, in the presence of 0.01 to 0.5 mole per cent of a cuprous or cupric salt and of 2 to 100 weight per cent of pyridine or quinoline, in the absence of oxygen and air, by heating to 160 DEG to 175 DEG C. for 2 to 24 hours and then at 200 DEG to 275 DEG C. for one or more hours. The molecular weight of the polymer may be increased by dissolving it in a solvent and oxidizing with sodium hypochlorite or lead tetraacetate, or with oxygen and cuprous chloride or potassium ferricyanide, or with lead dioxide and caustic alkali. The polymer may be cured by heating with dicumyl peroxide, di-t-butyl peroxide, benzoyl peroxide, lauroyl peroxide or azobisiso-butyronitrile. In examples, the purified potassium salts of p-chlorophenol, o-chlorophenol, 2 - chloro - 4 - phenyl phenol, 2 - chloro - 6-phenyl phenol, 2 - benzenesulphonyl - 4 - chlorophenol and 2 - benzoyl - chlorophenol, are heated in the presence of cuprous chloride and pyridine (in some instances pyridine is present in some of the monomers as pyridine of crystallization); the molecular weight of two polymers is increased by reacting them in solution with sodium hypochlorite and with cuprous chloride and oxygen.ALSO:Polyphenylene oxide polymers containing 0 to 75 mole percent paraphenylene oxide units with the remainder being ortho-phenylene oxide units, in which up to 30 percent of the units may carry the side groups phenyl, carboxyl aryl or sulphonyl aryl, may be coated on metal, ceramic, glass, plastics and laminate surfaces. In an Example a polymer containing 60 percent para- and 40 percent ortho-phenylene oxide units is dissolved in methylene chloride and xylene, t-butyl peroxide is added and the composition is coated on aluminium sheet and heated.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39293764A | 1964-08-28 | 1964-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1117327A true GB1117327A (en) | 1968-06-19 |
Family
ID=23552628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3424465A Expired GB1117327A (en) | 1964-08-28 | 1965-08-10 | Poly-(phenylene oxides) |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1570992A1 (en) |
| GB (1) | GB1117327A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028905A1 (en) * | 1996-02-12 | 1997-08-14 | Akzo Nobel N.V. | Heat treatment of polyphenylene oxide-coated metal |
| CN114729277A (en) * | 2019-06-27 | 2022-07-08 | 道格拉斯·约翰·弗雷德里克·哈雷特 | Method for reducing organic material to produce methane and/or hydrogen |
-
1965
- 1965-08-10 GB GB3424465A patent/GB1117327A/en not_active Expired
- 1965-08-27 DE DE19651570992 patent/DE1570992A1/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997028905A1 (en) * | 1996-02-12 | 1997-08-14 | Akzo Nobel N.V. | Heat treatment of polyphenylene oxide-coated metal |
| CN114729277A (en) * | 2019-06-27 | 2022-07-08 | 道格拉斯·约翰·弗雷德里克·哈雷特 | Method for reducing organic material to produce methane and/or hydrogen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1570992A1 (en) | 1970-03-19 |
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