PVC plasticizers and methods for making thereof
A plasticized PVC composition free of phthalate and having low color is disclosed. The composition comprises a morpholide plasticizer prepared from a fatty acid selected from a tall oil fatty acid, a tall oil fatty acid monomer derived therefrom, and mixtures thereof. The fatty acid has a total carbon footprint of <95% of the total carbon footprint of a fatty acid obtained from a vegetable oil. The morpholide is prepared from the reaction of a tall oil fatty acid with morpholine in the presence of a catalyst.
1. A morpholide composition, comprising a reaction product of a morpholine compound and a fatty acid selected from a tall oil fatty acid, a tall oil fatty acid monomer derived therefrom, and mixtures thereof;
wherein the fatty acid comprises 20-55 wt. % of oleic acid and 20-55 wt. % of linoleic acid;
wherein the fatty acid has a total greenhouse emission expressed as CO 2 g equivalents per kg of the fatty acid of <95% of the total CO 2 g equivalents per kg of a fatty acid obtained from a vegetable oil; and
wherein the morpholide composition has a Gardner color (neat) of less than 3.
2. The morpholide composition of claim 1 , wherein the fatty acid has an average greenhouse emission of less than 500 gram CO 2 equivalents per kg of the fatty acid.
3. The morpholide composition of claim 1 , wherein the morpholide composition has an acid number of less than 12 mg KOH/g.
4. The morpholide composition of claim 1 , wherein the morpholide composition has an amine value of less than 1 mg KOH/g.
5. The morpholide composition of claim 1 , wherein the fatty acid is a tall oil fatty acid monomer, and wherein the tall oil fatty acid monomer comprises iso-oleic acid.
6. A plasticizer composition comprising the morpholide composition of claim 1 .
7. A plasticized polyvinyl chloride (PVC) composition comprising the plasticizer composition of claim 6 .
8. The plasticized PVC composition of claim 7 , having a weight loss after 48 hours of less than 1% in an exudation test.
9. The plasticized PVC composition of claim 7 , having a yellowness index ΔE of 3 or less after aging at 70° C. for 7 days.
10. A method of preparing a plasticized PVC composition free of phthalate, comprising blending and compounding the morpholide composition of claim 1 with plasticized polyvinyl chloride and one or more polymer stabilizers and antioxidants.
11. A method of preparing a morpholide composition, comprising:
forming a mixture comprising a morpholine compound, a catalyst, and a fatty acid selected from a tall oil fatty acid, a tall oil fatty acid monomer derived therefrom, and mixtures thereof;
wherein the fatty acid comprises 20-55 wt. % of oleic acid and 20-55 wt. % of linoleic acid; and the fatty acid has a total greenhouse emission expressed as CO 2 g equivalents per kg of the fatty acid of <95% of the total CO 2 g equivalents per kg of a fatty acid obtained from a vegetable oil; and
isolating the morpholide composition;
wherein the morpholide composition has a Gardner color (neat) of less than 3.
12. The method of claim 11 , wherein the fatty acid has an average greenhouse emission of less than 500 gram CO 2 equivalents per kg of the fatty acid.
13. The method of claim 11 , wherein the catalyst is hypophosphorous acid.
14. The method of claim 11 , further comprising adding a scavenging agent to the isolated morpholide composition.
15. The method of claim 14 , wherein the scavenging agent is a substituted or an unsubstituted glycidyl ester.
16. The method of claim 10 , wherein said isolating the morpholide composition comprises wiped film evaporation or short path evaporation.
17. The method of claim 10 , further comprising a step for reducing residual unsaturation, selected from the group consisting of epoxidation, hydrogenation, bromination, chlorination, hydrochlorination, and hydrobromination.