Crosslinkable bioplasticizers
View Patent ↗A crosslinkable bioplasticizer is disclosed, a mixture of an epoxy-functional bio-derived plasticizer and an aromatic dianhydride. When heated, the mixture crosslinks, which can be accelerated by the addition of a Lewis Acid metal catalyst. The crosslinked bioplasticizer can be melt compounded into a thermoplastic resin or can be formed in situ in the thermoplastic resin. The crosslinking of the bioplasticizer can reduce blooming of the bioplasticizer to the surface of a plastic article made by extrusion, molding, calendering, or thermoforming techniques.
1. A crosslinkable bioplasticizer mixture, comprising:
(a) an epoxy-functional bio-derived plasticizer,
(b) an aromatic dianhydride, present in an amount from about 1 to about 50 parts per one hundred parts of the epoxy-functional bio-derived plasticizer, and
(c) butyl tin tris (2-ethyl hexanoate) catalyst,
wherein the epoxy-functional bio-derived plasticizer comprises one or more monoesters or one or more multiesters of epoxidized vegetable oils or combinations thereof,
wherein when heated, the mixture crosslinks to form a crosslinked bioplasticizer more rapidly than the mixture crosslinks without the presence of the catalyst.
2. The mixture of claim 1 , wherein the epoxy-functional bio-derived plasticizer comprises a fatty acid product derived from a vegetable oil having at least 80% by weight of unsaturated fatty acids, wherein said unsaturated fatty acids are substantially fully esterified with a monool or a polyol, and said esterified unsaturated fatty acids have been substantially fully epoxidized.
3. The mixture of claim 1 , wherein the epoxy-functional bio-derived plasticizer is an epoxy-functional fatty acid ester obtained from a vegetable oil selected from the group consisting of soybean oil, canola oil, corn oil, linseed oil, rapeseed oil, safflower oil, sunflower oil, tall oil, tung oil, and mixtures and derivatives thereof.
4. The mixture of claim 1 , wherein the epoxy-functional bio-derived plasticizer is an epoxidized fatty acid ester of an unsaturated fatty acid selected from the group consisting of oleic, linolenic, and linoleic acids, and combinations thereof.
5. The mixture of claim 1 , wherein the epoxy-functional bio-derived plasticizer is an epoxidized soyate selected from the group consisting of epoxidized pentaerythritol tetrasoyate; epoxidized propylene glycol disoyate; epoxidized ethylene glycol disoyate; epoxidized methyl soyate; epoxidized sucrose octasoyate; the epoxidized product of soybean oil interesterified with linseed oil; and combinations thereof.
6. The mixture of claim 1 , wherein the aromatic anhydride is pyromellitic dianhydride.
7. A thermoplastic compound comprising (a) a thermoplastic resin and (b) the crosslinkable bioplasticizer of claim 1 .
8. The compound of claim 7 , wherein the thermoplastic resin is selected from the group consisting of polyvinyl chloride, polylactic acid, and poly(meth)acrylate.
9. A method of making a crosslinked bioplasticizer of claim 1 , comprising the steps of:
(a) mixing the aromatic dianhydride and the epoxy-functional bio-derived plasticizer in a heated environment and
(b) introducing butyl tin tris (2-ethyl hexanoate) catalyst,
wherein the aromatic dianhydride and the epoxy-functional bioplasticizer react to form the crosslinked bioplasticizer.
10. The method of claim 9 , wherein the heated environment of step (a) is between 150° C. and 160° C.