DERIVATIVES OF FATTY ESTERS, FATTY ACIDS AND ROSINS
Provided is a compound of Formula (I); where R 1 , R 2 , L 1 and L 2 are as described herein. The compound of Formula I and copolymers thereof can be used as epoxy resins, curing agents, flame retardants, UV curable agents and the like. A process for preparing the compound of Formula (I) is also provided.
1 . A compound of Formula I:
wherein
R 1 is H, alkyl or
R 3 and R 4 are independently
R 2 , R 5 , R 6 and R 7 are independently CO(CH 2 ) m SH, CO(CH 2 ) m P(O)(OR 8 )(R 9 ), P(O)(OR 19 ) 2 , P(O)(OH) 2 , COC(R 10 )═CHR 19 or COC(R 10 )═CH 2 ;
R 8 is H, alkyl, or aryl;
R 9 is H, alkyl, or aryl;
R 10 is H, halo, alkyl, alkenyl, alkynyl, alkoxy, ester or CN;
R 19 is alkyl or aryl;
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 are independently C 1 -C 22 alkylene or C 2 -C 22 alkenylene;
m is 1 to 6; and
q is 1 to 6.
2 . The compound of claim 1 , wherein where R 8 and R 9 are each an aryl, and R 8 and R 9 are joined together by a single bond.
3 . The compound of claim 1 , wherein the compound is of Formula II:
wherein
R 3 and R 4 are independently
R 11 , R 12 , R 13 and R 14 are independently H, halo, alkyl, alkenyl, alkynyl, alkoxy, ester or CN; and
q is 1 to 6.
4 . The compound of claim 1 , wherein R 1 is H or
5 . (canceled)
6 . The compound of claim 3 , wherein R 11 , R 12 , R 13 and R 14 are all H or methyl.
7 . (canceled)
8 . The compound of claim 1 which is:
9 . (canceled)
10 . A compound of Formula Ia:
wherein
R 1 is H, alkyl or
R 3 and R 4 are independently
R 2 , R 5 , R 5a , R 6 , R 6a , R 7 and R 7a are independently CO(CH 2 ) m SH, CO(CH 2 ) m P(O)(OR 8 )(R 9 ), P(O)(OR 19 ) 2 , P(O)(OH) 2 , COC(R 10 )═CHR 19 , or COC(R 10 )═CH 2 ;
R 8 is H, alkyl, or aryl;
R 9 is H, alkyl, or aryl; or
R 8 and R 9 may both be aryl joined together by a single bond;
R 10 is H, halo, alkyl, alkenyl, alkynyl, alkoxy, ester or CN;
R 19 is alkyl or aryl;
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 are independently C 1 -C 22 alkylene; and
m is 1 to 6.
11 . The compound of claim 10 which is:
12 . (canceled)
13 . A co-polymer comprising a polymerization product of a polymerizable monomer with the compound of claim 1 .
14 . The co-polymer of claim 13 , wherein the polymerizable monomer comprises a polymerizable group, PG 1 .
15 . The co-polymer of claim 14 , wherein PG 1 is selected from the group consisting of isosorbide monoacrylyl, isosorbide diacrylyl, acrylyl, methacrylyl, epoxy, isocyano, styrenyl, vinyl, oxyvinyl, and a thiovinyl group.
16 . The co-polymer of claim 13 , wherein the co-polymer is of Formula III
wherein
R 1 is H, alkyl, or
R 3 and R 4 are independently
R 15 , R 16 , R 17 and R 18 are independently H, halo, alkyl, alkenyl, alkynyl, alkoxy, ester or CN;
PG 2 is the polymerized form of the polymerizable group PG 1 ;
each n and n′ is independently about 2 to about 100,000; and
q is 1 to 6.
17 - 20 . (canceled)
21 . A process for preparing a compound of Formula I, the process comprising:
mixing a compound selected from the group consisting of (HO)CO(CH 2 ) m SH, (HO)CO(CH 2 ) m P(O)(OR 8 )(R 9 ), (HO)P(O)(OR 19 ) 2 , (HO)OP(O)(OH) 2 and (HO)COC(R 10 )═CH 2 ;
a catalyst; and
a C 8 -C 30 unsaturated fatty acid or a C 8 -C 30 unsaturated fatty ester to form the compound of Formula I:
wherein
R 1 is H, alkyl or
R 3 and R 4 are independently
R 2 , R 5 , R 6 and R 7 are independently CO(CH 2 ) m SH, CO(CH 2 ) m P(O)(OR 8 )(R 9 ), P(O)(OR 19 ) 2 , P(O)(OH) 2 and)COC(R 10 )═CH 2 ;
R 8 is H, alkyl, or aryl;
R 9 is H, alkyl, or aryl;
R 10 is H, halo, alkyl, alkenyl, alkynyl, alkoxy, ester or CN;
R 19 is alkyl or aryl;
L 1 , L 2 , L 3 , L 4 , L 5 , L 6 and L 7 are independently C 1 -C 22 alkylene or C 2 -C 22 alkenylene;
m is 1 to 6; and
q is 1 to 6.
22 . The process of claim 21 , wherein where R 8 and R 9 are each an aryl, and R 8 and R 9 are joined together by a single bond.
23 . The process of claim 21 , wherein the mixing comprises heating the compound, the catalyst, and the C 8 -C 30 unsaturated fatty acid or the C 8 -C 30 unsaturated fatty ester, to a temperature of about 60° C. to about 120° C.
24 . (canceled)
25 . The process of claim 21 , wherein the catalyst is a Lewis acid catalyst.
26 . (canceled)
27 . The process of claim 21 , further comprising adding a polymerization inhibitor to the compound, the catalyst, and the C 8 -C 30 unsaturated fatty acid or the C 8 -C 30 unsaturated fatty ester.
28 . The process of claim 27 , wherein the polymerization inhibitor is selected from the group consisting of tert-butylhydroquinone, 4-methoxyphenol, p-toluhydroquinone, 1,4-benzoquinone, hydroquinone, copper(I) chloride, iron(III) chloride and any combination of two or more thereof.
29 . The process of claim 21 , wherein the process is conducted in the absence of a solvent.
30 - 35 . (canceled)
36 . A compound prepared by the process of claim 21 .
37 - 57 . (canceled)