GB887394A - Polymerisable mixtures and the production of copolymers on the basis of unsaturated polyester resins - Google Patents
Polymerisable mixtures and the production of copolymers on the basis of unsaturated polyester resinsInfo
- Publication number
- GB887394A GB887394A GB30052/59A GB3005259A GB887394A GB 887394 A GB887394 A GB 887394A GB 30052/59 A GB30052/59 A GB 30052/59A GB 3005259 A GB3005259 A GB 3005259A GB 887394 A GB887394 A GB 887394A
- Authority
- GB
- United Kingdom
- Prior art keywords
- unsaturated
- vinyl
- diol
- acids
- polyester resin
- 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
- 239000000203 mixture Substances 0.000 title abstract 5
- 229920006337 unsaturated polyester resin Polymers 0.000 title abstract 3
- 229920001577 copolymer Polymers 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 6
- 229920002554 vinyl polymer Polymers 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- -1 allyl ethers Chemical class 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 2
- 150000002978 peroxides Chemical class 0.000 abstract 2
- 229920001225 polyester resin Polymers 0.000 abstract 2
- 239000004645 polyester resin Substances 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- ZQHJVIHCDHJVII-OWOJBTEDSA-N (e)-2-chlorobut-2-enedioic acid Chemical compound OC(=O)\C=C(\Cl)C(O)=O ZQHJVIHCDHJVII-OWOJBTEDSA-N 0.000 abstract 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 abstract 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical class OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 abstract 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052684 Cerium Inorganic materials 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 abstract 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 abstract 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 150000002432 hydroperoxides Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 229910052745 lead Inorganic materials 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000005474 octanoate group Chemical group 0.000 abstract 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- 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
-
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
A polymerizable mixture contains (a) an unsaturated polyester resin containing the radical of an a , b unsaturated polycarboxylic acid but no b , g unsaturated ether radical and (b) an unsaturated polyester resin containing b , g unsaturated ether radicals but no a , b unsaturated polycarboxylic acid radicals. The mixture may also contain (c) at least one copolymerizable monomer containing the group CH2=C=. Preferred weight proportions are 95-20 parts of (a), 5 to 80 parts of (b), and 0 to 80 parts of (c). The polyester resin (a) may be prepared by reacting (i) an a , b unsaturated polycarboxylic acid or the half-ester or anhydride thereof with (ii) a polyhydric alcohol and, optionally, (iii) a non-polymerizable polycarboxylic acid. Starting materials specified are:-(i) maleic, fumaric, itaconic, citraconic, mesaconic, aconitic, muconic, and dimerized methacrylic acids, anhydrides and half-esters and chlormaleic acid; (ii) mono, di, and tri-ethylene glycols, propane diols 1.2 and 1.3, butane diols 1.2, 1.3 and 1.4, 2.21-dimethylpropane-diol-1.3, glycerine, trimethylol propane, pentaerythritol, cyclohexane-diol-1.4, terephthalic alcohol, and ethoxylated dihydroxydiphenylalkanes; and (iii) succinic, glutaric, adipic, pimelic, sebacic, suberic, -methyl glutaric, oxa- and sulphone-dibutyric, phthalic, iso-, tere-, di or tetrahydro-, endomethylene-tetrahydro-, hexachlorendomethylene-tetrahydro-, and tetrachlor- -phthalic, phenylenediacetic and the cyclohexane dicarboxylic acids and anhydrides. The polyester resin (b) may be derived from various combinations of non-polymerizable poly- and/or hydroxy-carboxylic acids and polyhydric alcohols, optionally with some monocarboxylic acid and/or monohydric alcohol, at least one component having a b -d unsaturated ether radical therein. Extensive lists of acids and alcohols are given wherein the unsaturated ether radical may be derived from allyl, methallyl or crotyl alcohol; butene-1-ol-3, butene-2-diol-1,4; butene-1-diol-3,4; hexene-3-diol-2,5; or cyclohexene-2-diol-1,4. Numerous optional comonomers (c) are mentioned including mono- and di-vinyl mono- and poly-nuclear aromatic hydrocarbons; vinyl pyridine; N-vinyl carbazole; vinyl ketones; vinyl sulphones; vinyl and allyl esters of saturated and unsaturated mono- and polycarboxylic acids; N-vinyl lactams; vinyl and allyl ethers; and the esters, amides and nitriles of acrylic, methacrylic and chloracrylic acids. Styrene is used in specific examples. The mixture may also contain non-polymerizable solvents. Inhibitors which may be used to stabilize the mixtures are hydroquinone, resorcinol, pyrocatechol or 2,6-di-t-butyl-p-cresol. Catalysts specified for effecting the copolymerization are the usual azo compounds and peroxides and hydroperoxides and t-butyl perbenzoate or permaleate. Redox systems of a peroxide and a tertiary amine or mercaptan may be used. "Metal driers" which may be used are Fe, Co, Ni, Mn, Cr, Pb, Zn, Ce, Al or Ca naphthenates, resinates, octoates or linoleates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE887394X | 1958-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB887394A true GB887394A (en) | 1962-01-17 |
Family
ID=6833784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30052/59A Expired GB887394A (en) | 1958-09-06 | 1959-09-03 | Polymerisable mixtures and the production of copolymers on the basis of unsaturated polyester resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB887394A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052642B1 (en) * | 1980-05-19 | 1985-09-18 | The Budd Company | Flame retardant molding composition |
| US20190153152A1 (en) * | 2017-11-20 | 2019-05-23 | Alliance For Sustainable Energy, Llc | Polymers and methods of making the same |
| US10836910B2 (en) | 2015-04-01 | 2020-11-17 | Swimc Llc | Pigment dispersion |
-
1959
- 1959-09-03 GB GB30052/59A patent/GB887394A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052642B1 (en) * | 1980-05-19 | 1985-09-18 | The Budd Company | Flame retardant molding composition |
| US10836910B2 (en) | 2015-04-01 | 2020-11-17 | Swimc Llc | Pigment dispersion |
| US11655372B2 (en) | 2015-04-01 | 2023-05-23 | Swimc Llc | Pigment dispersion |
| US12297356B2 (en) | 2015-04-01 | 2025-05-13 | Swimc Llc | Pigment dispersion |
| US20190153152A1 (en) * | 2017-11-20 | 2019-05-23 | Alliance For Sustainable Energy, Llc | Polymers and methods of making the same |
| US10988572B2 (en) * | 2017-11-20 | 2021-04-27 | Alliance For Sustainable Energy, Llc | Polymers and methods of making the same |
| US11518847B2 (en) | 2017-11-20 | 2022-12-06 | Alliance For Sustainable Energy, Llc | Polymers and methods of making the same |
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