IE33622B1 - Improvements in or relating to unsaturated polyester-based coating compositions - Google Patents
Improvements in or relating to unsaturated polyester-based coating compositionsInfo
- Publication number
- IE33622B1 IE33622B1 IE152969A IE152969A IE33622B1 IE 33622 B1 IE33622 B1 IE 33622B1 IE 152969 A IE152969 A IE 152969A IE 152969 A IE152969 A IE 152969A IE 33622 B1 IE33622 B1 IE 33622B1
- Authority
- IE
- Ireland
- Prior art keywords
- maleic anhydride
- benzoic acid
- ethylene glycol
- polyester
- styrene
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title abstract 2
- 229920006305 unsaturated polyester Polymers 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 8
- 239000005711 Benzoic acid Substances 0.000 abstract 7
- 235000010233 benzoic acid Nutrition 0.000 abstract 7
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 abstract 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 4
- 229920000728 polyester Polymers 0.000 abstract 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical group C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 3
- 239000003973 paint Substances 0.000 abstract 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- 239000001530 fumaric acid Substances 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- 229920001225 polyester resin Polymers 0.000 abstract 2
- 239000004645 polyester resin Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- HKYMBBNHOYJXHW-UHFFFAOYSA-N 3-phenyl-1h-indene-1,2-dicarboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)C(C(O)=O)=C1C1=CC=CC=C1 HKYMBBNHOYJXHW-UHFFFAOYSA-N 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004146 Propane-1,2-diol Substances 0.000 abstract 1
- 229910010413 TiO 2 Inorganic materials 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 229920001727 cellulose butyrate Polymers 0.000 abstract 1
- PFURGBBHAOXLIO-WDSKDSINSA-N cyclohexane-1,2-diol Chemical compound O[C@H]1CCCC[C@@H]1O PFURGBBHAOXLIO-WDSKDSINSA-N 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- C08G63/66—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to 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
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
-
- 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)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Developing Agents For Electrophotography (AREA)
- Polymerisation Methods In General (AREA)
Abstract
1295043 Curing unsaturated polyesters by electron irradiation SISSONS BROS & CO Ltd 13 Nov 1969 [15 Nov 1968] 54360/68 Heading C3P Coating compositions comprising at least one unsaturated polyester resin of number average molecular weight between 800 and 1500 and with a level of aliphatic unsaturation of at least 3. preferably at least 3À5 double bonds per 1000 gms. (defined as meaning that it contains a total of at least 3À5 gram moles of the unsaturated component per 1000 gms. of resin), mixed with or dissolved in at least one olefinically unsaturated comonomer, are cured by irradiation with electrons which preferably have an average potential in the range 100 to 250 keV. The "feed ratio", the ratio of unsaturation in the comonomer(s), to unsaturation in the polyester, is preferably in the range 1À0 to 1À5. Examples describe the preparation and curing with styrene by the above process, of polyesters derived from (1) maleic anhydride, ethylene glycol and benzoic acid, modified with dicyclopentadiene; (2) maleic anhydride or fumaric acid, and diethylene glycol and isophthalic acid; (3) maleic anhydride, tetrahydrophthalic anhydride, ethylene glycol and benzoic acid; (4) maleic anhydride, tetrahydrophthalic anhydride, neopentyl glycol and benzoic acid; (6) maleic anhydride, tetrahydrophthalic anhydride, phenyl indene dicarboxylic acid, ethylene glycol, and benzoic acid; (7) maleic anhydride, tetrahydrophthalic anhydride, ethylene glycol, cyclohexane-1,2-diol and benzoic acid; (8) maleic anhydride or fumaric acid, and propane- 1,2-diol and benzoic acid, both modified with dicyclopentadiene; (9) maleic anhydride, ethylene glycol and benzoic acid, modified with dicyclopentadiene, and cured in trichloroethylene solution. Examples (10) and (11) describe paint compositions using the polyester of Example (1), cured with styrene and methylmethacrylate respectively. In all the examples, before the dissolution in styrene an inhibitor, hydroquinone, is added. The polyester resin in Example (1) is made into a paint by mixing with a melamine formaldehyde resin, a cellulose acetate/butyrate, a silicone oil, and curing with methylmethacrylate. The polyester in Example 6 is also dissolved in styrene and mixed with TiO 2 and a melamine formaldehyde resin, to give a curable paint. The polyester resin of Example 9 is similarly treated.
[GB1295043A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5436068 | 1968-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33622L IE33622L (en) | 1970-05-15 |
| IE33622B1 true IE33622B1 (en) | 1974-09-04 |
Family
ID=10470749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE152969A IE33622B1 (en) | 1968-11-15 | 1969-11-11 | Improvements in or relating to unsaturated polyester-based coating compositions |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4910817B1 (en) |
| AT (1) | AT313441B (en) |
| BE (1) | BE741723A (en) |
| CA (1) | CA924263A (en) |
| CH (1) | CH518320A (en) |
| DE (1) | DE1957424A1 (en) |
| FI (1) | FI49625C (en) |
| FR (1) | FR2023438A1 (en) |
| GB (1) | GB1295043A (en) |
| IE (1) | IE33622B1 (en) |
| LU (1) | LU59819A1 (en) |
| NL (1) | NL6917117A (en) |
| NO (1) | NO134382C (en) |
| SE (1) | SE376923B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2302842C3 (en) * | 1973-01-20 | 1980-08-28 | Bayer Ag, 5090 Leverkusen | Molding compounds based on unsaturated polyester, polymerizable vinyl monomers and cellulose esters |
| FR2426345A1 (en) * | 1978-05-18 | 1979-12-14 | Carpano & Pons | CONNECTION BODY, FOR TELEPHONE SYSTEMS |
| BE888519A (en) * | 1981-04-22 | 1981-10-22 | Gni I P Institutlakokrasochnoi | COMPOSITION FOR PAINTS AND VARNISHES |
| NL1005809C2 (en) | 1997-04-14 | 1998-10-19 | Dsm Nv | Powder paint binder composition. |
| US9221973B2 (en) | 2009-03-25 | 2015-12-29 | Dsm Ip Assets B.V. | Resin composition |
| WO2021148588A1 (en) * | 2020-01-24 | 2021-07-29 | Mercene Coatings Ab | Coating including primer |
-
1968
- 1968-11-15 GB GB1295043D patent/GB1295043A/en not_active Expired
-
1969
- 1969-11-11 IE IE152969A patent/IE33622B1/en unknown
- 1969-11-13 NL NL6917117A patent/NL6917117A/xx unknown
- 1969-11-14 JP JP9132869A patent/JPS4910817B1/ja active Pending
- 1969-11-14 CH CH1701769A patent/CH518320A/en not_active IP Right Cessation
- 1969-11-14 BE BE741723D patent/BE741723A/xx unknown
- 1969-11-14 SE SE1566669A patent/SE376923B/xx unknown
- 1969-11-14 NO NO452869A patent/NO134382C/no unknown
- 1969-11-14 FI FI329969A patent/FI49625C/en active
- 1969-11-14 DE DE19691957424 patent/DE1957424A1/en active Pending
- 1969-11-14 FR FR6939295A patent/FR2023438A1/fr not_active Withdrawn
- 1969-11-14 AT AT1069969A patent/AT313441B/en not_active IP Right Cessation
- 1969-11-14 LU LU59819D patent/LU59819A1/xx unknown
- 1969-11-14 CA CA067466A patent/CA924263A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT313441B (en) | 1974-02-25 |
| BE741723A (en) | 1970-04-16 |
| CH518320A (en) | 1972-01-31 |
| NO134382B (en) | 1976-06-21 |
| NO134382C (en) | 1976-09-29 |
| FR2023438A1 (en) | 1970-08-21 |
| SE376923B (en) | 1975-06-16 |
| JPS4910817B1 (en) | 1974-03-13 |
| GB1295043A (en) | 1972-11-01 |
| DE1957424A1 (en) | 1970-07-23 |
| IE33622L (en) | 1970-05-15 |
| NL6917117A (en) | 1970-05-20 |
| FI49625B (en) | 1975-04-30 |
| FI49625C (en) | 1975-08-11 |
| LU59819A1 (en) | 1970-01-14 |
| CA924263A (en) | 1973-04-10 |
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