Plasticizer for halogen resins

Patent metadata

Field	Value
Publication number	US-11945932-B2
Application number	US-201916978534-A
Country	US
Kind code	B2
Filing date	Feb 13, 2019
Priority date	Mar 8, 2018
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

The present invention relates to [1] a plasticizer for a halogen-based resin containing a mixture of didecyl phthalates each containing a linear or branched C10 alkyl group, in which a content of di-n-decyl phthalate in the mixture is not less than 48 mol % and not more than 70 mol %; [2] a plasticizer composition for a halogen-based resin containing the aforementioned plasticizer; and [3] a halogen-based resin composition containing a halogen-based resin and the aforementioned plasticizer. The plasticizer of the present invention has an excellent plasticizing effect on a halogen-based resin and at the same time, can exhibit excellent effects of improving all of productivity, processability, kneading properties and heat resistance without deterioration in the respective properties.

First claim

The invention claimed is:

1. A plasticizer for a halogen-based resin comprising a mixture of didecyl phthalates each comprising a linear or branched C 10 alkyl group, in which a content of di-n-decyl phthalate in the mixture is not less than 48 mol % and not more than 70 mol %, and the remainder of the mixture of didecyl phthalates contains one or more additional didecyl phthalate(s) other than di-n-decyl phthalate.

2. The plasticizer for a halogen-based resin according to claim 1 , wherein the C 10 alkyl group is derived from a combination of n-decanol and at least one alcohol selected from the group consisting of isodecanol, 2-propyl-1-heptanol and 4-methyl-2-propyl-1-hexanol.

3. The plasticizer for a halogen-based resin according to claim 1 , wherein the one or more additional didecyl phthalate(s) other than di-n-decyl phthalate is at least one compound selected from the group consisting of di-1-methylnonyl phthalate, di-1-ethyloctyl phthalate, di-1-propylheptyl phthalate, di-1-butylhexyl phthalate, di-isodecyl phthalate, di-2-propylheptyl phthalate, di-4-methyl-2-propylhexyl phthalate, n-decyl (1-methylnonyl) phthalate, n-decyl (1-ethyloctyl) phthalate, n-decyl (1-propylheptyl) phthalate, n-decyl (1-butylhexyl) phthalate, n-decyl (isodecyl) phthalate, n-decyl (2-propylheptyl) phthalate, n-decyl (4-methyl-2-propylhexyl) phthalate, isodecyl (2-propylheptyl) phthalate, isodecyl (4-methyl-2-propylhexyl) phthalate, and 2-propylheptyl (4-methyl-2-propylhexyl) phthalate.

4. The plasticizer for a halogen-based resin according to claim 1 , wherein the one or more additional didecyl phthalate(s) other than di-n-decyl phthalate is at least one compound selected from the group consisting of di-2-propylheptyl phthalate, n-decyl (2-propylheptyl) phthalate, and 2-propylheptyl (4-methyl-2-propylhexyl) phthalate.

5. The plasticizer for a halogen-based resin according to claim 1 , wherein the mixture of didecyl phthalates is represented by the following general formula (1):

wherein, R 1 and R 2 are each independently a linear or branched C 10 alkyl group, and
the mixture of didecyl phthalates that are each represented by the general formula (1) is in the form of a mixture containing the following compounds (i) to (iii),
(i) di-n-decyl phthalate in which the substituent groups R 1 and R 2 both are an n-decyl group,
(ii) a compound of the formula (1) in which one of the substituent groups R 1 and R 2 is an n-decyl group and the other thereof is a branched decyl group, and
(iii) a compound of the formula (1) in which both of the substituent groups R 1 and R 2 are branched decyl groups.

6. The plasticizer for a halogen-based resin according to claim 5 , wherein the branched decyl group includes at least one alcohol selected from the group consisting of 1-methylnonyl group, 1-ethyloctyl group, 1-propylheptyl group, 1-butylhexyl group, isodecyl group, 2-propylheptyl group, and 4-methyl-2-propylhexyl group.

7. A plasticizer composition for a halogen-based resin comprising the plasticizer according to claim 1 , wherein the plasticizer in the composition is not less than 40% by mass and not more than 100% by mass.

8. A halogen-based resin composition comprising a halogen-based resin, and the plasticizer according to claim 1 .

9. The halogen-based resin composition according to claim 8 , wherein a content of the plasticizer in the composition is not less than 0.01 part by mass and not more than 200 parts by mass on the basis of 100 parts by mass of the halogen-based resin.

10. The halogen-based resin composition according to claim 8 , wherein the halogen-based resin is at least one resin selected from the group consisting of a vinyl chloride-based resin, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, chloro-sulfonated polyethylene, and a chloroprene rubber.

11. A method for producing a plasticizer for a halogen-based resin comprising a mixture of didecyl phthalates each comprising a linear or branched C 10 alkyl group, wherein the mixture of the didecyl phthalates is obtained by an esterification reaction between a phthalic acid raw material and an alcohol raw material,
the phthalic acid raw material is at least one compound selected from the group consisting of phthalic acid and phthalic anhydride, and comprising the following methods (i) or (ii):
(i) a method of producing the plasticizer by using in the esterification reaction a mixed decanol as a raw material in which a content of n-decanol in the alcohol raw material is precisely controlled such that a content of di-n-decyl phthalate in the plasticizer is not less than 48 mol % and not more than 70 mol % after producing the plasticizer, and
(ii) a method of producing the plasticizer by mixing di-n-decyl phthalate and one or more additional didecyl phthalate(s) other than di-n-decyl phthalate such that a content of the di-n-decyl phthalate in the plasticizer is adjusted to a predetermined value of not less than 48 mol % and not more than 70 mol %.

12. The method for producing a plasticizer for a halogen-based resin according to claim 11 , wherein, in the method (i), mixed decanol is consisting of n-decanol and a branched alcohol including at least one alcohol selected from the group consisting of isodecanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol, 2-propyl-1-heptanol, and 4-methyl-2-propyl-1-hexanol.

13. The method for producing a plasticizer for a halogen-based resin according to claim 11 , wherein, in the method (i), the alcohol raw material consists of n-decanol and a branched alcohol including at least one alcohol selected from the group consisting of 2-propyl-1-heptanol and 4-methyl-2-propyl-1-hexanol .

14. The method for producing a plasticizer for a halogen-based resin according to claim 11 , wherein, in the method (ii), the one or more additional didecyl phthalate(s) other than di-n-decyl phthalate is at least one compound selected from the group consisting of di-1-methylnonyl phthalate, di-1-ethyloctyl phthalate, di-1-propylheptyl phthalate, di-1-butylhexyl phthalate, di-isodecyl phthalate, di-2-propylheptyl phthalate, di-4-methyl-2-propylhexyl phthalate, n-decyl (1-methylnonyl) phthalate, n-decyl (1-ethyloctyl) phthalate, n-decyl (1-propylheptyl) phthalate, n-decyl (1-butylhexyl) phthalate, n-decyl (isodecyl) phthalate, n-decyl (2-propylheptyl) phthalate, n-decyl (4-methyl-2-propylhexyl) phthalate, isodecyl (2-propylheptyl) phthalate, isodecyl (4-methyl-2-propylhexyl) phthalate, and 2-propylheptyl (4-methyl-2-propylhexyl) phthalate.

15. The method for producing a plasticizer for a halogen-based resin according to claim 11 , wherein, in the method (ii), the one or more additional didecyl phthalate(s) other than di-n-decyl phthalate is at least one compound selected from the group consisting of di-2-propylheptyl phthalate, n-decyl (2-propylheptyl) phthalate, and 2-propylheptyl (4-methyl-2-propylhexyl) phthalate.

Assignees

• Kao Corp

Inventors

• Oshiro Kojun
• Okutsu Munehisa

Classifications

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• C08K5/0016

  Plasticisers · CPC title

• C08L11/00

  Compositions of homopolymers or copolymers of chloroprene · CPC title

• C08L27/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• C08L27/08

  Homopolymers or copolymers of vinylidene chloride · CPC title