GB912898A - Unsaturated polycarbonate esters - Google Patents
Unsaturated polycarbonate estersInfo
- Publication number
- GB912898A GB912898A GB35030/61A GB3503061A GB912898A GB 912898 A GB912898 A GB 912898A GB 35030/61 A GB35030/61 A GB 35030/61A GB 3503061 A GB3503061 A GB 3503061A GB 912898 A GB912898 A GB 912898A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- phenol
- unsaturated
- dihydric
- chloroformate
- 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
- 229920000515 polycarbonate Polymers 0.000 title abstract 5
- 239000004417 polycarbonate Substances 0.000 title abstract 5
- 150000002148 esters Chemical class 0.000 title 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 4
- -1 butene diols Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 2
- 229940095064 tartrate Drugs 0.000 abstract 2
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 abstract 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 abstract 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000011 acetone peroxide Substances 0.000 abstract 1
- 235000019401 acetone peroxide Nutrition 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 abstract 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012772 electrical insulation material Substances 0.000 abstract 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 238000004382 potting Methods 0.000 abstract 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229920006305 unsaturated polyester Polymers 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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
- C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/26—General preparatory processes using halocarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/26—General preparatory processes using halocarbonates
- C08G64/263—General preparatory processes using halocarbonates and cyclic ethers
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
- Developing Agents For Electrophotography (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
New polymerizable polycarbonates contain the residues of a dihydric phenol and an unsaturated aliphatic or cycloaliphatic dihydric alcohol. The polycarbonates may be made (a) by reacting the dihydric phenol with a bis-chloroformate of the unsaturated dihydric alcohol or (b) by reacting the bis-chloroformate of the dihydric phenol with the unsaturated dihydric alcohol possibly in admixture with a saturated dihydroxy compound. Specified dihydric alcohols are butene diols, 1:3-cyclopentadiene diol, mono- or di-allyl tartrate, mono- or di-methallyl tartrate and a - or b -glycerine monoallyl ether. Specified dihydric phenols are bis-phenol A and unsaturated compounds of formula <FORM:0912898/IV(a)/1> where X is a divalent linking radical and R is an unsaturated radical, e.g. a hydrocarbon, halohydrocarbon, ether or ester radical. The polycarbonates, either by themselves or with other polymerizable compounds, may be polymerized by the action of peroxides (e.g. benzoyl peroxide, acetone peroxide, t-butyl peroxide, cumene hydroperoxide or isopropyl peroxydicarbonate), or ultra-violet, infra-red, beta-or gamma-radiation. Specified other polymerizable compounds are styrene, vinyl acetate, diallyl maleate, ethylene glycol dimethacrylate, diallyl phthalate, glycol maleates, glycol fumarates and a mixture of styrene and an unsaturated polyester. The polycarbonate may also be set hard by heating them with sulphur. In Examples (1) The bis-chloroformate of 2-butene-1:4-diol is reacted with bis-phenol A in the presence of methylene chloride and aqueous sodium hydroxide; (2) A mixture of styrene, poly(propylene maleate phthalate) and the copolycarbonate of bis-phenol A and butene diol is copolymerized by heating it with benzoyl peroxide; (3) 1-butene-1:4-diol and the bis-chloroformate of bis-phenol A are reacted in the presence of pyridine and benzene. The resins may be used in the manufacture of laminates, metal coatings, electrical insulation materials, potting compositions, films and fibres. Reference has been directed by the Comptroller to Specification 842,264.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69805557A | 1957-11-22 | 1957-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912898A true GB912898A (en) | 1962-12-12 |
Family
ID=24803741
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35033/61A Expired GB909613A (en) | 1957-11-22 | 1958-11-12 | Polycarbonate resins |
| GB3503261A Expired GB906790A (en) | 1957-11-22 | 1958-11-12 | Polycarbonates derived from diepoxy compounds |
| GB36350/58A Expired GB906012A (en) | 1957-11-22 | 1958-11-12 | Polymers containing carbonate and carbamate groups |
| GB35030/61A Expired GB912898A (en) | 1957-11-22 | 1958-11-12 | Unsaturated polycarbonate esters |
| GB35031/61A Expired GB912203A (en) | 1957-11-22 | 1958-11-12 | Mixed polycarbonate-polycarboxylic acid esters |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35033/61A Expired GB909613A (en) | 1957-11-22 | 1958-11-12 | Polycarbonate resins |
| GB3503261A Expired GB906790A (en) | 1957-11-22 | 1958-11-12 | Polycarbonates derived from diepoxy compounds |
| GB36350/58A Expired GB906012A (en) | 1957-11-22 | 1958-11-12 | Polymers containing carbonate and carbamate groups |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35031/61A Expired GB912203A (en) | 1957-11-22 | 1958-11-12 | Mixed polycarbonate-polycarboxylic acid esters |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH396413A (en) |
| DE (3) | DE1420309A1 (en) |
| GB (5) | GB909613A (en) |
| NL (1) | NL129040C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728716A (en) * | 1985-11-12 | 1988-03-01 | General Electric Company | Polycarbonate exhibiting improved impact properties containing divalent residue of polymerized alkadiene monomer |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2435508C2 (en) * | 1974-07-24 | 1985-08-22 | Bayer Ag, 5090 Leverkusen | Flame-retardant polycarbonate molding compounds |
| DE2636783C2 (en) * | 1976-08-16 | 1982-10-21 | Bayer Ag, 5090 Leverkusen | Process for the production of high molecular weight, segmented, thermoplastically processable polyester-polycarbonates |
| US4476294A (en) * | 1983-12-16 | 1984-10-09 | General Electric Company | Copolyester-carbonate resins |
| CN115003723B (en) * | 2020-01-07 | 2023-12-05 | 诠达化学股份有限公司 | Thermoplastic polyurethane with high tensile strength, preparation formula and manufacturing method thereof |
-
1958
- 1958-11-12 GB GB35033/61A patent/GB909613A/en not_active Expired
- 1958-11-12 GB GB3503261A patent/GB906790A/en not_active Expired
- 1958-11-12 GB GB36350/58A patent/GB906012A/en not_active Expired
- 1958-11-12 GB GB35030/61A patent/GB912898A/en not_active Expired
- 1958-11-12 GB GB35031/61A patent/GB912203A/en not_active Expired
- 1958-11-19 DE DE19581420309 patent/DE1420309A1/en active Pending
- 1958-11-19 DE DE19581420278 patent/DE1420278A1/en active Pending
- 1958-11-19 DE DE19581520483 patent/DE1520483A1/en active Pending
- 1958-11-21 CH CH3765A patent/CH396413A/en unknown
- 1958-11-21 CH CH6644358A patent/CH398083A/en unknown
-
1964
- 1964-08-20 NL NL6409652A patent/NL129040C/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728716A (en) * | 1985-11-12 | 1988-03-01 | General Electric Company | Polycarbonate exhibiting improved impact properties containing divalent residue of polymerized alkadiene monomer |
Also Published As
| Publication number | Publication date |
|---|---|
| CH398083A (en) | 1965-08-31 |
| NL129040C (en) | 1970-01-15 |
| GB909613A (en) | 1962-10-31 |
| CH396413A (en) | 1965-07-31 |
| GB912203A (en) | 1962-12-05 |
| DE1420309A1 (en) | 1969-02-20 |
| DE1420278A1 (en) | 1968-11-14 |
| NL6409652A (en) | 1964-10-12 |
| GB906012A (en) | 1962-09-19 |
| DE1520483A1 (en) | 1970-02-19 |
| GB906790A (en) | 1962-09-26 |
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