GB1003088A - Fatty acid modified epoxy resins - Google Patents
Fatty acid modified epoxy resinsInfo
- Publication number
- GB1003088A GB1003088A GB2099462A GB2099462A GB1003088A GB 1003088 A GB1003088 A GB 1003088A GB 2099462 A GB2099462 A GB 2099462A GB 2099462 A GB2099462 A GB 2099462A GB 1003088 A GB1003088 A GB 1003088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- ester
- hydroxyphenyl
- mixed
- ch2chohch2
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract 7
- 229930195729 fatty acid Natural products 0.000 title abstract 7
- 239000000194 fatty acid Substances 0.000 title abstract 7
- -1 Fatty acid modified epoxy resins Chemical class 0.000 title abstract 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 7
- 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 6
- 150000002148 esters Chemical class 0.000 abstract 6
- 150000004665 fatty acids Chemical class 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 abstract 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000000944 linseed oil Substances 0.000 abstract 4
- 235000021388 linseed oil Nutrition 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 3
- 229910000831 Steel Inorganic materials 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000010959 steel Substances 0.000 abstract 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 239000011294 coal tar pitch Substances 0.000 abstract 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 abstract 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 2
- 239000001294 propane Substances 0.000 abstract 2
- 235000015096 spirit Nutrition 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- 229910052726 zirconium Inorganic materials 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 229940093475 2-ethoxyethanol Drugs 0.000 abstract 1
- OEUZHYQGRHNTHD-UHFFFAOYSA-N 4,4-bis(2-hydroxyphenyl)pentanoic acid Chemical class C=1C=CC=C(O)C=1C(CCC(O)=O)(C)C1=CC=CC=C1O OEUZHYQGRHNTHD-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000010665 pine oil Substances 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000002383 tung oil Substances 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000008096 xylene Substances 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1472—Fatty acids
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/066—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with chain extension or advancing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F7/00—Chemical modification of drying oils
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Resins (AREA)
Abstract
Esters of formula <FORM:1003088/C3/1> in which X is <FORM:1003088/C3/2> or -CH2CHOHCH2- or <FORM:1003088/C3/3> ; Z is <FORM:1003088/C3/4> in which R is an unsaturated hydrocarbon radical of 10-36 carbon atoms; p is 0, 1 or 2 at least one half of them being greater than 0; terminal X groups are <FORM:1003088/C3/5> when p=0, -CH2CHOHCH2-when p=1, and <FORM:1003088/C3/6> when p=2, and internal X groups are -CH2CHOHCH2- when p=0, and -CH2-CH-CH2- when p=1; n is an integer from 1 to 5; <FORM:1003088/C3/7> wherein R is lower alkyl, chloro, or bromo, and y is 0, 1 or 2, the ether linkages in the benzene rings being attached in the 4-positions when y=0; and <FORM:1003088/C3/8> or <FORM:1003088/C3/9> wherein R1 and R11 are hydrogen or lower alkyl, are produced by reacting 1 to 10 equivalent weights of a polyglycidyl ether ester of formula <FORM:1003088/C3/100> with 1 equivalent weight of a polyhydric phenol of formula <FORM:1003088/C3/111> and reacting the product with sufficient unsaturated fatty acid, having 10-36 atoms in its hydrocarbon chain, to constitute 10-75% by weight of the total reactants. In Examples (6)-(9) the product of reaction of a glycidyl ether-ester prepared from 4,4-bis-(4-hydroxy-phenyl) pentanoic acid and epichlorhydrin, and 2,2 - bis - (4 - hydroxyphenyl) propane was reacted with linseed oil fatty acids, soya bean oil fatty acids, tung oil fatty acids to produce resins soluble in benzene, toluene, xylene, diacetone alcohol, pine oil, 2-ethoxy ethanol, hot butanol or propanol, methyl ethyl ketone, methyl isobutyl ketone and 1,2-dichloroethane. In Example (10) the same polyglycidyl ether ester was reacted with 2,2-bis-(4-[b -hydroxyethoxy] phenyl) propane and linseed oil fatty acids. In Example (11) a solution of the resin of Example (6) in methyl ethyl ketone was mixed with ethylene diamine and formed to a film on a steel panel. In Example (12) the ester of Example (7) was mixed with diethylene triamine and coal tar pitch to give a brushable coating composition. In Example (13) the product of Example (10) was dissolved in mineral spirits and mixed with cobalt naphthenate and zirconium octoate, and used to form a film on a wooden panel. The resins may be used to modify urea-formaldehyde, phenolformaldehyde and alkyd resins, especially for coating the interiors of cans. They are also compatible with vinyl resins. Specification 768,206 is referred to.ALSO:Esters of formula <FORM:1003088/C2/1> in which X is <FORM:1003088/C2/2> or -CH2CHOHCH2- or -CH2CHCH2-; Z is <FORM:1003088/C2/3> in which R is an unsaturated hydrocarbon radical of 10-36 atoms; p is 0, 1 or 2, at least one half of them being greater than 0; terminal X groups are <FORM:1003088/C2/4> when p = 0, -CH2CHOHCH2- when p = 1, and <FORM:1003088/C2/5> when p = 2, and internal X groups are -CH2CHOHCH2- when p = 0, and -CH2-1CH-CH2- when p = 1; n is an integer, from 1 to 5; <FORM:1003088/C2/6> wherein R is lower alkyl, chloro, or bromo and y is 0, 1, or 2, the ether linkages in the benzene rings being attached in the 4-positions when y = 0; and <FORM:1003088/C2/7> or <FORM:1003088/C2/8> wherein R1 and R11 are hydrogen or lower alkyl, are produced by reacting 1 to 10 equivalent weights of a polyglycidyl ether ester of formula <FORM:1003088/C2/9> with 1 equivalent weight of a polyhydric phenol of formula <FORM:1003088/C2/100> In Examples 6-9 a glycidyl ether-ester is prepared from 4,4-bis-(4-hydroxyphenyl)pentanoic acid and epichlorhydrin; and 2,2-bis-(4-hydroxyphenyl)propane. In the examples glyglycidyl ether esters are prepared from 4,4-bis-(hydroxyphenyl)pentanoic acids, some of which carry chlorine, bromine and/or alkyl substituents on the benzene rings and epichlohydrin and these are reacted with a 2,2-bis-(4-hydroxyphenyl)propane which may have alkyl substituents on the benzene rings. Specification 768,206 is referred to.ALSO:In Example 11, a synthetic ester prepared from a glycidyl ether ester from 4,4-bis(4-hydroxyphenyl)pentanoic acid and epichlorhydrin reacted first with 2,2,-bis(4-hydroxyphenyl)propane and then with linseed oil fatty acids, was dissolved in methyl ethyl ketone and mixed with ethylene diamine. A film of the composition was spread on a steel panel and baked. In Example 12 a similar ester was mixed with diethylene triamine and coal tar pitch and brushed on to a steel pipe line joint at 100 DEG C. In Example 13 an ester from the polyglycidyl ether-ester of 4,4-bis(4-hydroxyphenyl)pentanoic acid; 2,2-bis(4-[b -hydroxyethoxyl]phenyl)propane and linseed oil fatty acids was dissolved in mixed spirits, mixed with cobalt naphthenate and zirconium octoate and applied to a wooden panel. Specification 768,206 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14875361A | 1961-10-30 | 1961-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003088A true GB1003088A (en) | 1965-09-02 |
Family
ID=22527201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2099462A Expired GB1003088A (en) | 1961-10-30 | 1962-05-31 | Fatty acid modified epoxy resins |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE656492A (en) |
| CH (1) | CH407075A (en) |
| GB (1) | GB1003088A (en) |
-
1962
- 1962-05-31 GB GB2099462A patent/GB1003088A/en not_active Expired
- 1962-06-18 CH CH729462A patent/CH407075A/en unknown
-
1964
- 1964-12-01 BE BE656492A patent/BE656492A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE656492A (en) | 1965-04-01 |
| CH407075A (en) | 1966-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2765288A (en) | Coating compositions containing coal tar pitch and an epoxy ether resin | |
| US4132706A (en) | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids | |
| US4171420A (en) | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids | |
| US4177216A (en) | Novel tributyl (2,5-dihydroxyphenyl)phosphonium hydroxide inner salts | |
| US3634542A (en) | Unsaturated polyesters esterified with polycarboxylic acid anhydride and containing polyepoxide | |
| GB881498A (en) | Improvements in coating compositions | |
| US4431782A (en) | Process for the preparation of radiation-curable, water-thinnable vinyl ester resins | |
| US2934516A (en) | Carboxy-copolymer epoxide compositions and their preparation | |
| US4020030A (en) | Reaction products of epoxy resins, organic sulfides and protic acids | |
| GB1115271A (en) | Thermosetting compositions comprising addition products of epoxide resins | |
| US4089826A (en) | New curing agents for epoxide resins | |
| US3971834A (en) | Modified acrylate resin | |
| US2947712A (en) | Epoxide resin compositions | |
| GB1311317A (en) | Bituminous polypoxide compositions | |
| GB1003088A (en) | Fatty acid modified epoxy resins | |
| GB768748A (en) | Process for the preparation of fusible or liquid hydroxy-substituted allylic ethers and derivatives thereof | |
| US4180487A (en) | Epoxy curable resin composition | |
| US3968181A (en) | Modified acrylate resin | |
| GB1091552A (en) | Curable mixtures of epoxy resins and tertiary amines | |
| US2889305A (en) | Corrosion-resistant coatings containing coal tar oil and an epoxy resin | |
| US3856725A (en) | Water-soluble resins and methods for their preparation | |
| US2626939A (en) | Alkyds and varnishes comprising same | |
| US2965602A (en) | Carboxy-copolymer epoxide compositions and their preparation | |
| US4116901A (en) | Low temperature curing ester copolymers-phenolic condensates | |
| GB576089A (en) | Rust-preventive hydrocarbon compositions |