Patent GB-1003088-A (GB)
Title: Fatty acid modified epoxy resins
IPC: C08G59/06
Filed: 1962-05-31
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.