Dibasic esters and the use thereof in plasticizer compositions
View Patent ↗Dibasic esters (diesters) and their use in plasticizer compositions are generally disclosed. In some embodiments, the diesters are branched-chain esters of long-chain alkanedioic acids, such as octadecanedioic acid. In some embodiments, such plasticizer compositions are used to increase the plasticity of a polymer resin, such as a vinyl chloride resin or poly vinyl butyral. In some other embodiments, such plasticizer compositions are used to lower the glass transition temperature of a polymer resin. In some embodiments, at least a portion of the plasticizer is derived from a renewable source, such as a natural oil.
1. A compound of formula (I):
wherein:
X 1 is —(CH 2 ) 16 —;
R 1 is 2-methylpentyl, 2-ethylhexyl, 2-butyloctyl, or 3-methylbutyl;
R 2 is a branched or unbranched C 4-24 alkyl, a branched or unbranched C 4-24 alkenyl, a branched or unbranched C 4-30 oxyalkyl, or a branched or unbranched C 4-30 oxyalkenyl, each of which is optionally substituted by one or more substituents selected independently from R 3 ;
R 3 is a halogen atom, —OH, —NH 2 , C 1-6 alkyl, C 1-6 heteroalkyl, C 2-6 alkenyl, or C 2-6 heteroalkenyl.
2. The compound of claim 1 , wherein R 2 is a branched C 4-20 alkyl, a branched C 4-20 alkenyl, a branched C 4-20 oxyalkyl, or a branched C 4-20 oxyalkenyl, each of which is optionally substituted by one or more substituents selected independently from R 3 .
3. The compound of claim 2 , wherein R 2 is a branched C 4-20 alkyl, which comprises branching at the 1-position of the alkyl moiety.
4. The compound of claim 2 , wherein R 2 is a branched C 4-20 alkyl, which comprises branching at the 2-position of the alkyl moiety.
5. The compound of claim 2 , wherein R 2 is a branched C 4-20 alkyl, which comprises branching at the 3-position of the alkyl moiety.
6. The compound of claim 2 , wherein R 2 is 2-methylpentyl, 2-ethylhexyl, 2-butyloctyl, or 3-methylbutyl.
7. The compound of claim 1 , wherein R 2 is branched or unbranched C 4-30 oxyalkyl, which is optionally substituted by one or more substituents selected independently from R 3 .
8. The compound of claim 7 , wherein R 2 is —(CH 2 —CH 2 —O) 1-12 —(C 1-6 unbranched alkyl).
9. The plasticizer composition of claim 8 , wherein R 2 is —CH 2 —CH 2 —O—CH 3 , —(CH 2 —CH 2 —O) 2 —CH 3 , —(CH 2 —CH 2 —O) 3 —CH 3 , —(CH 2 —CH 2 —O) 4 —CH 3 , —(CH 2 —CH 2 —O) 5 —CH 3 , —(CH 2 —CH 2 —O) 6 —CH 3 , —(CH 2 —CH 2 —O) 7 —CH 3 , —(CH 2 —CH 2 —O) 8 —CH 3 , —(CH 2 —CH 2 —O) 9 —CH 3 , —(CH 2 —CH 2 —O) 10 —CH 3 , —(CH 2 —CH 2 —O) 11 —CH 3 , or —(CH 2 —CH 2 —O) 12 —CH 2 —CH 3 .
10. A plasticizer composition, comprising a compound of claim 1 .