Plasticizer and method of preparing the same

Patent metadata

Field	Value
Publication number	US-9051262-B2
Application number	US-201113695736-A
Country	US
Kind code	B2
Filing date	Feb 28, 2011
Priority date	May 4, 2010
Publication date	Jun 9, 2015
Grant date	Jun 9, 2015

Abstract

The present invention provides an ester plasticizer for polyvinyl chloride (PVC) resin, epoxy resin or urethane resin and a method of preparing the same. More particularly, the present invention provides an ester plasticizer using triacetin and coconut oil-based biodiesel as raw materials, which can prepare a resin composition having excellent plasticizing efficiency and improved physical properties such as tensile strength and the like.
When a polyvinyl chloride resin or the like is manufactured using the ester plasticizer, there are advantages in that an environment-friendly product having an excellent plasticizing efficiency and in that the physical properties such as hardness, tensile strength, etc. of the product are improved.

First claim

The invention claimed is:

1. A method of preparing a plasticizer composition, comprising:
fractionating coconut oil methyl ester to obtain a fatty acid methyl ester of C6 to C12;
mixing the fatty acid methyl ester with triacetin and methyl benzoate; and
transesterifying the mixture using a basic catalyst,
wherein the produced plasticizer composition includes glycerin triester having, based on the total amount of the plasticizer composition,
40-80 wt % mono-functional triester,
20-60 wt % di-functional triester, and
0-20 wt % tri-functional trimester;

wherein the plasticizer composition comprises 15-40 wt % aromatic components;
and
wherein
the mono-functional triester is a structure in which one benzoyl group or one acyl group of 6 to 21 carbon atoms is disposed at the ester end thereof, the other ester end groups are acetyl groups,
the di-functional triester is a structure in which two benzoyl groups or two acyl groups of 6 to 21 carbon atoms is disposed at the ester end thereof, the other ester end groups are acetyl groups, and
the tri-functional triester is a structure in which three benzoyl groups or three acyl groups of 6 to 21 carbon atoms is disposed at the ester end thereof.

2. The method according to claim 1 , wherein the fatty acid methyl ester has a carbon number of 6 to 12.

3. The method according to claim 1 , wherein, in the mixing the fatty acid methyl ester with triacetin and methyl benzoate, a mixing molar ratio of fatty acid methyl ester: triacetin: methyl benzoate is 1:1 to 5:0.1 to 0.5.

4. The method according to claim 3 , wherein the mixing molar ratio of fatty acid methyl ester: triacetin: methyl benzoate is 1:1 to 3:0.1 to 0.3.

5. The method according to claim 1 , further comprising: removing moisture from the mixture at a pressure of 1 to 100 torr and a temperature of 30 to 120° C. before transesterifying the mixture.

6. The method according to claim 1 , wherein the basic catalyst is sodium methoxide or sodium ethoxide.

7. The method according to claim 1 , wherein the basic catalyst is added in an amount of 0.1 to 10 mol % based on the total amount of triacetin.

8. The method according to claim 1 , wherein transesterifying the mixture is conducted at a temperature of 70 to 120° C.

9. The method according to 1, wherein transesterifying the mixture is conducted at a temperature of 150 to 290° C. under a heterogeneous catalyst in which an alumina carrier is supported with alkali metal oxide.

10. The method according to claim 9 , wherein the alkali metal oxide is K 2 O, Li 2 O or Na 2 O.

11. A plasticizer composition comprising:
glycerin triester having, based on the total amount of the plasticizer composition,
40-80 wt % mono-functional triester,
20-60 wt % di-functional triester and
5-20 wt % tri-functional triester;

wherein
the plasticizer composition comprise 15-40 wt % aromatic components;
the mono-functional triester is a structure in which one benzoyl group or one acyl group of 6 to 21 carbon atoms is disposed at one ester end thereof and the other ester end groups are acetyl groups,
the di-functional triester is a structure in which two benzoyl groups or two acyl groups of 6 to 21 carbon atoms is disposed at two ester ends thereof and the other ester end group is an acetyl group, and
the tri-functional triester is a structure in which three benzoyl groups or three acyl groups of 6 to 21 carbon atoms is disposed at the three ester ends thereof.

12. A resin composition, comprising the plasticizer composition of claim 11 in an amount of 10-100 phr based on a polyvinyl chloride resin, an epoxy resin, or a urethane resin.

Assignees

• Kwon Tae Wook
• Lee Sung Gi
• Chung Ki Nam
• Hong Seung Gweon
• Sk Innovation Co Ltd
• Sk Global Chemical Co Ltd

Inventors

• Kwon Tae Wook
• Lee Sung Gi
• Chung Ki Nam
• Hong Seung Gweon

Classifications

• C08K5/103

  with polyalcohols · CPC title

• C07C69/00

  Esters of carboxylic acids; Esters of carbonic or haloformic acids (ortho esters, see the relevant groups, e.g. C07C43/32) · CPC title

• C07C69/78 Primary

  Benzoic acid esters · CPC title

• C08K5/101

  of monocarboxylic acids · CPC title

• C08G63/78

  Preparation processes · CPC title