GB1042525A - Production of polyesters - Google Patents
Production of polyestersInfo
- Publication number
- GB1042525A GB1042525A GB24738/64A GB2473864A GB1042525A GB 1042525 A GB1042525 A GB 1042525A GB 24738/64 A GB24738/64 A GB 24738/64A GB 2473864 A GB2473864 A GB 2473864A GB 1042525 A GB1042525 A GB 1042525A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anhydride
- acid
- acids
- oxide
- alkylene oxide
- 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
- 229920000728 polyester Polymers 0.000 title abstract 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 5
- 150000008064 anhydrides Chemical class 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000001530 fumaric acid Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 150000002642 lithium compounds Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
- C08G63/58—Cyclic ethers; Cyclic carbonates; Cyclic sulfites ; Cyclic orthoesters
Abstract
A polyester is prepared by heating at least one a ,b -unsaturated dicarboxylic acid or anhydride, or a mixture of dicarboxylic acids or anhydrides of which at least 10 mol. per cent are a ,b -unsaturated, with ethylene oxide, propylene oxide or butylene oxide, or a mixture thereof, in the presence of a catalytic amount of a lithium compound until a product of acid number 20-130 is obtained, then heating this at 200-240 DEG C. for 30 minutes to 6 hours. The preferred anhydride or acid mixtures are phthalic anhydride/maleic anhydride and phthalic anhydride/fumaric acid Other suitable anhydrides for use with a ,b -unsaturated acids or anhydrides are those of succinic, adipic, glutaric, octadecylsuccinic, diglycollic, thiodiglycollic, tetrahydrophthalic, tetrachlorophthalic and other substituted phthalic acids, and those of Diels-Alder adducts of cyclopentadiene and maleic anhydride. The preferred alkylene oxide is propylene oxide. Suitable lithium compounds are the hydroxide, ethoxide, chloride, bromide, carbonate, acetate, nitrate, sulphate and phthalate. The preferred catalyst is lithium hydroxide, in amount 0.05-0.5% by weight of the polyester. The use of initiators, e.g. water, ethylene glycol, propylene glycol, fumaric acid or maleic acid, is desirable. In practice the acids, catalyst and initiator are mixed, and the alkylene oxide is then added at once, or in increments, or continuously during the reaction. Different acids may be added at various stages of the reaction, which may be held at 125-135 DEG C. during the addition of alkylene oxide or allowed to rise from 90 DEG to 200 DEG C. It is usually desirable to add further alkylene oxide after the heating to 200-240 DEG C., to bring the acid number to 10-40, after which the polyester may be thinned with 20-50% by weight of the composition of a polymerizable monomer containing at least one CH2 = C < group, e.g. styrene or vinyl toluene. The catalyst also may be added incrementally or continuously with the alkylene oxide. In examples, mixtures of phthalic anhydride with maleic anhydride or fumaric acid are heated, with or without water, with propylene oxide in the presence of lithium hydroxide, and the products are mixed with styrene. A comparison example, using sodium hydroxide, is supplied.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28851963A | 1963-06-17 | 1963-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1042525A true GB1042525A (en) | 1966-09-14 |
Family
ID=23107467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24738/64A Expired GB1042525A (en) | 1963-06-17 | 1964-06-15 | Production of polyesters |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT253229B (en) |
| ES (1) | ES301028A1 (en) |
| FR (1) | FR1398634A (en) |
| GB (1) | GB1042525A (en) |
| NL (1) | NL6406783A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023066269A1 (en) * | 2021-10-19 | 2023-04-27 | 山东联欣环保科技有限公司 | Method for mixed feeding of phthalic anhydride and propylene oxide, equipment, and application |
-
1964
- 1964-06-15 FR FR978339A patent/FR1398634A/en not_active Expired
- 1964-06-15 GB GB24738/64A patent/GB1042525A/en not_active Expired
- 1964-06-15 NL NL6406783A patent/NL6406783A/xx unknown
- 1964-06-15 AT AT509864A patent/AT253229B/en active
- 1964-06-15 ES ES0301028A patent/ES301028A1/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023066269A1 (en) * | 2021-10-19 | 2023-04-27 | 山东联欣环保科技有限公司 | Method for mixed feeding of phthalic anhydride and propylene oxide, equipment, and application |
Also Published As
| Publication number | Publication date |
|---|---|
| AT253229B (en) | 1967-03-28 |
| ES301028A1 (en) | 1965-01-01 |
| FR1398634A (en) | 1965-05-07 |
| NL6406783A (en) | 1964-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1061758A (en) | Production of polyesters | |
| GB996248A (en) | Preparation of polyesters | |
| GB924624A (en) | Block polyesters and process for producing same | |
| US3919063A (en) | Electron-beam radiation-curing method of unsaturated polyesters derived from endomethylene tetrahydrophthalic acid | |
| US2830966A (en) | Unsaturated polyester resin composition containing indan carboxylic acids and process of preparing the same | |
| GB1042525A (en) | Production of polyesters | |
| US2537375A (en) | Method of curing polyester resins | |
| GB1101247A (en) | Production of unsaturated polyesters | |
| GB832169A (en) | Improvements in curing ester resins | |
| GB755321A (en) | Manufacture of copolymers | |
| GB1140922A (en) | Process for continuous production of polyesters | |
| GB914426A (en) | Solvent-resistant flexible polymerisation products on the basis of unsaturated polyester resins | |
| US2757158A (en) | Polyester resin compositions | |
| GB1082227A (en) | Process for preparation of polyester | |
| ES361915A1 (en) | Catalyzed isomerization of alpha-beta unsaturated carboxylic acid esters | |
| GB1049023A (en) | Improvements in or relating to allyl dihaloalkyl esters of oxyacids of antimony, boron, silicon and titanium and their use as fire-retardant additives for synthetic polyester resins and curable resin compositions | |
| GB1478561A (en) | Process for producing terephthalic unsaturated polyester resin | |
| US3296219A (en) | Acid treatment of polyester resins containing alkylene oxide | |
| GB801529A (en) | Organosilicon resins | |
| US3074866A (en) | Irradiated polymers | |
| US3689594A (en) | Curing processes using di-(2-methylbenzoyl)peroxide | |
| JPS55155012A (en) | Photosetting type, heatresisting resin composition | |
| US3082161A (en) | Irradiated polymers | |
| GB925078A (en) | Improved unsaturated polyester resins | |
| GB966661A (en) | Process for the preparation of coatings based on unsaturated polyester resins and monomeric vinyl compounds |