PVC plasticizers and methods for making thereof

Patent metadata

Field	Value
Publication number	US-11279813-B2
Application number	US-201916515498-A
Country	US
Kind code	B2
Filing date	Jul 18, 2019
Priority date	Aug 2, 2018
Publication date	Mar 22, 2022
Grant date	Mar 22, 2022

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Kraton Polymers Llc

Inventors

• Wei Xiangyun
• Tian Jason
• Miller H Jerrold
• Lange Jos H M

Classifications

• C08K5/0016

  Plasticisers · CPC title

• C08K2201/019

  the composition being defined by the absence of a certain additive · CPC title

• C08F14/06

  Vinyl chloride · CPC title

• C08K5/20 Primary

  Carboxylic acid amides · CPC title

• C07D295/185 Primary

  from aliphatic carboxylic acids · CPC title