GB1030487A - Polyester resins - Google Patents
Polyester resinsInfo
- Publication number
- GB1030487A GB1030487A GB21784/64A GB2178464A GB1030487A GB 1030487 A GB1030487 A GB 1030487A GB 21784/64 A GB21784/64 A GB 21784/64A GB 2178464 A GB2178464 A GB 2178464A GB 1030487 A GB1030487 A GB 1030487A
- Authority
- GB
- United Kingdom
- Prior art keywords
- per cent
- mol per
- mixture
- maleic
- anhydride
- 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
- 229920001225 polyester resin Polymers 0.000 title 1
- 239000004645 polyester resin Substances 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 10
- 239000000203 mixture Substances 0.000 abstract 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- 150000008064 anhydrides Chemical class 0.000 abstract 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- 229940043375 1,5-pentanediol Drugs 0.000 abstract 1
- QPNJQIYRAUMPGR-UHFFFAOYSA-N C(C(CCCCO)O)O.C(C=CCO)O Chemical compound C(C(CCCCO)O)O.C(C=CCO)O QPNJQIYRAUMPGR-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- 229930195725 Mannitol Natural products 0.000 abstract 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 1
- -1 ethylene, propylene Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 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
- 239000000594 mannitol Substances 0.000 abstract 1
- 235000010355 mannitol Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000151 polyglycol Chemical group 0.000 abstract 1
- 239000010695 polyglycol Chemical group 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920006337 unsaturated polyester resin 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
An unsaturated polyester resin is prepared by heating (a) an alkylene oxide, (b) a mixture of maleic anhydride and another dicarboxylic anhydride, the mixture containing at least 10 mol per cent of maleic anhydride, and (c) 10-50 mol per cent, based on (b) of water or a dihydric or polyhydric alcohol, at a temperature below 180 DEG C. until the acid number is less than 240, then at 180-250 DEG C. until the acid number of the product is less than 60. Suitable alkylene oxides are ethylene, propylene and butylene oxides. The preferred anhydride mixture contains equimolar amounts of maleic and phthalic anhydrides. Other anhydrides suitable for mixing with maleic anhydride in the present invention are those of succinic, glutaric, octenylsuccinic, diglycollic, thiodioglycollic, tetrahydrophthalic, tetrachlorophthalic and other substituted phthalic acids and Diels-Alder adducts of maleic acid with e.g. cyclopentadiene. Suitable polyhydric alcohols are ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, triethylene glycol, 1,3-butane diol, 1,5-pentane diol, 2-butene-1,4-diol 1,2,6-hexane triol, pentaerythritol, sorbitol and mannitol. The polyhydric alcohol may comprise up to 25 mol per cent of a monohydric alcohol. The molar ratio of alkylene oxide to anhydride mixture may be from 0.9-4.0 to 1, ratios greater than 1 to 1 permitting the formation of diglycol or polyglycol units in the polyester chain. In a suitable process the mixture of anhydrides and the water or alcohol is heated to 100-150 DEG C., and the alkylene oxide is added over 1 1/2 -3 hours, the temperature being held at 100-150 DEG C. until the acid number falls below 240, then at 180-250 DEG C. until the acid number falls below 60 and the viscosity is F to I on the Gardner scale. The mixture is then cooled to 160 DEG C. and a stabilizer, e.g. hydroquinone is added. 30-40 wt. per cent (based on the cut resin) of a copolymerizable monomer, e.g. styrene, may be added. In examples an equimolar mixture of maleic and phthalic anhydrides is mixed with water (13, 25.5, 37.5 and 50 mol per cent) or propylene glycol (25 and 37.5 mol per cent) and treated with propylene oxide (105-143 mol per cent), the product being mixed with 30 mol per cent of styrene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28398363A | 1963-05-29 | 1963-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1030487A true GB1030487A (en) | 1966-05-25 |
Family
ID=23088398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21784/64A Expired GB1030487A (en) | 1963-05-29 | 1964-05-26 | Polyester resins |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE648421A (en) |
| ES (1) | ES300280A1 (en) |
| FR (1) | FR1397670A (en) |
| GB (1) | GB1030487A (en) |
| NL (1) | NL6405881A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2108840B1 (en) * | 1970-10-12 | 1973-08-10 | Rhone Progil |
-
0
- BE BE648421D patent/BE648421A/xx unknown
-
1964
- 1964-05-26 ES ES300280A patent/ES300280A1/en not_active Expired
- 1964-05-26 GB GB21784/64A patent/GB1030487A/en not_active Expired
- 1964-05-26 NL NL6405881A patent/NL6405881A/xx unknown
- 1964-05-26 FR FR975894A patent/FR1397670A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1397670A (en) | 1965-04-30 |
| NL6405881A (en) | 1964-11-30 |
| ES300280A1 (en) | 1966-04-01 |
| BE648421A (en) |
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