Low polarity dimerate and trimerate esters as plasticizers for elastomers
View Patent ↗An elastomeric composition including a natural or synthetic rubber, and a cyclic dimerate ester and/or a cyclic trimerate ester plasticizer.
1. A plasticized elastomer composition comprising rubber selected from the group consisting of natural rubber, synthetic rubber, and a combination thereof, and a cyclic dimerate or trimerate ester plasticizer compound having formula I, II, or a mixture thereof:
wherein R 5 and R 7 , same or different, are a C 3 –C 24 hydrocarbon chain, straight chain or branched, either saturated or having 1 to 6 carbon-to-carbon double bonds;
R 6 and R 8 , same or different, are a C 3 –C 24 alkyl radical, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds; and
R 10 and R 11 , same or different, are a C 3 –C 24 , saturated hydrocarbon chain, straight chain or branched; or an unsaturated C 3 –C 24 , hydrocarbon chain, straight chain or branched, having 1 to 6 carbon-to-carbon double bonds;
wherein R 12 , R 14 and R 18 , same or different, are a C 3 –C 24 hydrocarbon chain, straight chain or branched, either saturated or having 1 to 6 carbon-to-carbon double bonds;
R 13 , R 15 and R 19 , same or different, are a C 3 –C 24 alkyl radical, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds; and
R 16 , R 17 and R 20 , same or different, are a C 3 –C 24 saturated hydrocarbon chain, straight chain or branched; or unsaturated C 3 –C 24 hydrocarbon chain, straight chain or branched, containing 1 to 6 carbon-to-carbon double bonds.
2. A composition in accordance with claim 1 , wherein the plasticizer is selected from the group consisting of formula I, II, and a combination thereof:
wherein R 5 and R 7 , are a C 6 –C 24 hydrocarbon chain, straight chain or branched; either saturated or having 1 to 3 carbon-to-carbon double bonds;
R 6 and R 8 , same or different, are a C 3 –C 18 alkyl radical, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds, and
R 10 and R 11 , same or different, are C 3 –C 18 saturated hydrocarbon chain, straight chain or branched; or an unsaturated hydrocarbon chain, straight chain or branched, containing 1 to 3 carbon-to-carbon double bonds;
wherein R 12 , R 14 and R 18 , same or different, are a C 6 –C 24 hydrocarbon chain, straight chain or branched, either saturated or containing 1 to 3 carbon-to-carbon double bonds;
R 13 , R 15 and R 19 , same or different, are a C 3 –C 18 alkyl radical, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds; and
R 16 , R 17 and R 20 , same or different, are a C 3 –C 18 saturated hydrocarbon chain, straight chain or branched; or an unsaturated C 3 –C 18 hydrocarbon-chain, straight chain or branched, containing 1 to 3 carbon-to-carbon double bonds.
3. A composition in accordance with claim 1 , wherein the plasticizer compound having formula I, II, or a mixture thereof is present in an amount from about 0.1 parts to about 50 parts by weight per 100 parts of rubber.
4. A composition in accordance with claim 1 , wherein the plasticizer compound having formula I, II, or a mixture thereof is present in an amount from about 2 parts to about 40 parts by weight per 100 parts of rubber.
5. A composition in accordance with claim 1 , wherein the plasticizer compound having formula I, II, or a mixture thereof is present in an amount from about 10 parts to about 35 parts per 100 parts of rubber.
6. A composition in accordance with claim 1 , wherein the plasticizer is an unsaturated diester formed by the reaction of a C 36 dimer acid and a C 3 –C 18 alcohol, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds.
7. A composition in accordance with claim 6 , wherein the alcohol is 2-ethylhexyl alcohol.
8. A composition in accordance with claim 6 , wherein the alcohol is tridecyl alcohol.
9. A composition in accordance with claim 6 , wherein the alcohol is oleyl alcohol.
10. A composition in accordance with claim 6 , wherein the alcohol is n-butyl alcohol.
11. A composition in accordance with claim 1 , wherein the plasticizer comprises the following dimer acid reacted with a C 3 –C 24 alcohol:
12. A composition in accordance with claim 1 , wherein the plasticizer comprises the following dimer acid reacted with a C 3 –C 24 alcohol:
13. A composition in accordance with claim 1 , wherein the plasticizer comprises the following dimer acid reacted with a C 3 –C 24 alcohol:
14. A composition in accordance with claim 1 , wherein the plasticizer is the reaction product of a C 3 –C 24 alcohol with a tricarboxylic acid, having the following formula:
15. A composition in accordance with claim 1 , wherein the plasticizer is a combination of compounds represented by formula I and II.
16. A composition in accordance with claim 15 , wherein the plasticizer is a reaction product of a C 3 –C 24 alcohol straight chain or branched, saturated, or unsaturated having 1 to 3 carbon-to-carbon double bonds, with a dimer acid having CAS #61788-89-4.
17. A composition in accordance with claim 16 , wherein the alcohol is 2-ethylhexyl alcohol.
18. A composition in accordance with claim 16 , wherein the alcohol is tridecyl alcohol.
19. A rubber composition in accordance with claim 16 , wherein the alcohol is oleyl alcohol.
20. A composition in accordance with claim 16 , wherein the alcohol is n-butyl alcohol.
21. The composition in accordance with claim 1 , wherein R 5 , R 7 , R 12 , R 14 are fatty acid residues derived from animal or vegetable fatty acids.
22. The composition of claim 21 , wherein the fatty acids are selected from the group consisting of butter; lard; tallow; grease; herring; menhaden; pilchard; sardine; babassu; castor; coconut; corn; cottonseed; jojoba; linseed; oiticia; olive; palm; palm kernel; peanut; rapeseed; safflower; soya; sunflower; tall; tung; and mixtures thereof.
23. The composition of claim 21 , wherein the fatty acid residues are selected from the group consisting of hexanoic; octanoic; decanoic; dodecanoic; 9-dodecenoic; tetradecanoic; 9-tetradecenoic; hexadecanoic; 9-hexadecenoic; octadecanoic; 9-octadecenoic; 9-octadecenoic, 12-hydroxy; 9,12-octadecadienoic; 9,12,15-octadecatrienoic; 9,11,13-octadecatrienoic; 9,11,13-octadecatrienoic; 4-oxo; octadecatetrenoic; eicosanoic; 11-eicosenoic; eicosadienoic; eicosatrienoic; 5,8,11,14-eicosatetraenoic; eicosapentaenoic; docosanoic; 13-docosenoic; docosatetraenoic; 4,8,12,15,19-docosapentaenoic; docosahexaenoic; tetracosenoic; and 4,8,12,15,18,21-tetracosahexaenoic.
24. A method of plasticizing an elastomeric composition, said elastomeric composition including one or more natural or synthetic rubbers, and a rubber vulcanizing agent, comprising adding to said rubber composition, in an amount of about 0.1 parts to about 50 parts by weight per 100 parts of rubber in the composition, a cyclic ester plasticizer of formula I, II, or mixtures thereof:
wherein R 5 and R 7 , same or different, are a C 3 –C 24 hydrocarbon chain, straight chain or branched, either saturated or having 1 to 6 carbon-to-carbon double bonds;
R 6 and R 8 , same or different, are a C 3 –C 24 alkyl radical, straight chain or branched; and
R 10 and R 11 , same or different, are a C 3 –C 24 , saturated hydrocarbon chain, straight chain or branched; or an unsaturated C 3 –C 24 , hydrocarbon chain, straight chain or branched, having 1 to 6 carbon-to-carbon double bonds;
wherein R 12 , R 14 and R 18 , same or different, are a C 3 –C 24 hydrocarbon chain, straight chain or branched, either saturated or having 1 to 6 carbon-to-carbon double bonds;
R 13 , R 14 and R 19 , same or different, are a C 3 –C 24 alkyl radical, straight chain or branched, saturated, or unsaturated containing 1 to 3 carbon-to-carbon double bonds; and
R 16 , R 17 and R 20 , same or different, are a C 3 –C 24 saturated hydrocarbon chain, straight chain or branched; or unsaturated C 3 –C 24 hydrocarbon chain, straight chain or branched, containing 1 to 6 carbon-to-carbon double bonds.
25. The method of claim 24 , wherein the cyclic ester plasticizer is added in an amount from about 2 parts to about 40 parts by weight per 100 parts of rubber.
26. The method of claim 24 , wherein the cyclic ester plasticizer is added in an amount from about 10 parts to about 35 parts per 100 parts of rubber.