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EP-4741462-A1 - PLASTICIZER COMPOSITION

EP4741462A1EP 4741462 A1EP4741462 A1EP 4741462A1EP-4741462-A1

Abstract

The present invention relates to a plasticizer composition including a plasticizer A composed of a phthalic acid diester represented by a general formula (I); and a plasticizer B containing an isosorbide diester (b1) represented by a general formula (II): in the general formula (I), R 1 and R 2 are each a linear or branched alkyl group having 8 or more and 14 or less carbon atoms, and be the same or different, in the general formula (II), R 3 and R 4 are each a linear or branched alkyl group having different carbon numbers.

Inventors

  • OSHIRO, KOJUN

Assignees

  • Kao Corporation

Dates

Publication Date
20260513
Application Date
20240702

Claims (14)

  1. A plasticizer composition comprising: a plasticizer A composed of a phthalic acid diester represented by a general formula (I); and a plasticizer B containing an isosorbide diester (b1) represented by a general formula (II): in the general formula (I), R 1 and R 2 are each a linear or branched alkyl group having 8 or more and 14 or less carbon atoms, and be the same or different, in the general formula (II), R 3 and R 4 are each a linear or branched alkyl group having different carbon numbers.
  2. The plasticizer composition according to claim 1, wherein in the isosorbide diester (b1) represented by the general formula (II), R 3 and R 4 are each a linear or branched alkyl group having 7 or more and 9 or less carbon atoms.
  3. The plasticizer composition according to claim 1 or 2, wherein the isosorbide diester (b1) represented by the general formula (II) is an isosorbide (octanoic acid/decanoic acid) diester.
  4. The plasticizer composition according to any one of claims 1 to 3, wherein the plasticizer B further contains an isosorbide diester (b2) represented by a general formula (III), and a content of the isosorbide diester (b1) in the plasticizer B is 10 mass% or more: in the general formula (III), R 5 and R 6 are each a linear or branched alkyl group having the same carbon number.
  5. The plasticizer composition according to claim 4, wherein in the isosorbide diester (b2) represented by the general formula (III), R 5 and R 6 each represent a linear or branched alkyl group having 7 or more and 9 or less carbon atoms.
  6. The plasticizer composition according to any one of claims 1 to 5, wherein a mass ratio of the plasticizer A to the plasticizer B (plasticizer A/plasticizer B) is 5/95 or more and 85/15 or less.
  7. A halogen-based resin composition comprising the plasticizer composition according to any one of claims 1 to 6.
  8. A method for producing a plasticizer composition, comprising mixing a phthalic acid diester represented by a general formula (I); and a plasticizer B containing an isosorbide diester (b1) represented by a general formula (II): in the general formula (I), R 1 and R 2 are each a linear or branched alkyl group having 8 or more and 14 or less carbon atoms, and be the same or different, in the general formula (II), R 3 and R 4 are each a linear or branched alkyl group having different carbon numbers.
  9. The method for producing a plasticizer composition according to claim 8, comprising esterifying isosorbide and a carboxylic acid raw material containing at least two linear or branched aliphatic carboxylic acids having different carbon numbers to obtain the plasticizer B.
  10. The method for producing a plasticizer composition according to claim 9, wherein the linear or branched aliphatic carboxylic acids having different carbon numbers are linear or branched aliphatic carboxylic acids having 8 or more and 10 or less carbon atoms.
  11. The method for producing a plasticizer composition according to claim 10, wherein the linear or branched aliphatic carboxylic acids having 8 or more and 10 or less carbon atoms are octanoic acid and decanoic acid.
  12. The method for producing a plasticizer composition according to claim 10 or 11, wherein a molar ratio of a linear or branched aliphatic carboxylic acid having 8 carbon atoms to a linear or branched aliphatic carboxylic acid having 10 carbon atoms in the carboxylic acid raw material (carboxylic acid having 8 carbon atoms/carboxylic acid having 10 carbon atoms) is 5/95 or more and 92/8 or less.
  13. The method for producing a plasticizer composition according to any one of claims 8 to 12, comprising esterifying a phthalic acid raw material and an alcohol raw material containing a linear or branched aliphatic alcohol having 8 or more and 14 or less carbon atoms to obtain the plasticizer A.
  14. The method for producing a plasticizer composition according to claim 13, wherein a molar ratio of a linear aliphatic alcohol to a branched aliphatic alcohol in the alcohol raw material (linear aliphatic alcohol/branched aliphatic alcohol) is 70/30 or more and 100/0 or less.

Description

TECHNICAL FIELD The present invention relates to plasticizer composition, and a halogen-based resin composition containing thereof and a method for producing a plasticizer composition. BACKGROUND ART Halogen-based resins such as vinyl chloride resin (PVC) are important resins used in various fields as general-purpose polymers. For example, PVC is used for various applications such as house interior items such as wall paper; general-purpose products such as toys; and automobile related materials such as sealing materials. When a halogen-based resin is used, for example, a plasticizer, a diluent, a viscosity-decreasing agent, a filler such as calcium carbonate, a pigment, a flame retardant, a foaming agent, a stabilizer, and the like are blended in a halogen-based resin powder to prepare a halogen-based resin composition. However, the plasticizer blended for improving the processability of the halogen-based resin composition has a problem of heat resistance in which the plasticizer volatilizes from the surface of the halogen-based resin composition when exposed to a high temperature, and cracks and the like occur due to curing of the halogen-based resin composition. JP-A-2015-516009 (Patent Document 1) discloses a composition containing: based on a total weight of (A) and (B), 0.1 wt% to 99 wt% of at least one 1,4:3,6-dianhydrohexitol ester (A) having a molar mass in a range of 255 to 345 g.mol-1, the ester (A) being selected from monoesters and diesters of isosorbide, isomannide and isoidide; and 1% to 99.9 wt% of at least one compound (B) having a molar mass of more than 345 g.mol-1, the compound (B) being selected from a 1,4:3,6-dianhydrohexitol ester selected from monoesters and diesters of isosorbide, isomannide and isoidide; a 1,4:3,6-dianhydrohexitol ester group containing 1 to 24 carbon atoms, preferably a group containing 6 to 12 carbon atoms; an ester of cyclohexane polycarboxylic acid; an ester of phthalic acid; and a glycerol ester. SUMMARY OF THE INVENTION The present invention relates to a plasticizer composition containing: a plasticizer A composed of a phthalic acid diester represented by a general formula (I); and a plasticizer B containing an isosorbide diester (b1) represented by a general formula (II). in the general formula (I), R1 and R2 are each a linear or branched alkyl group having 8 or more and 14 or less carbon atoms, and be the same or different. in the general formula (II), R3 and R4 are each a linear or branched alkyl group having different carbon numbers. The composition described in Patent Document 1 has a high plasticization rate, but still has a problem in heat resistance. The present invention relates to a plasticizer composition which is used in a halogen-based resin composition to give a halogen-based resin composition having excellent heat resistance. The present inventors have found that a plasticizer composition containing a plasticizer A composed of a phthalic acid diester having a structure derived from an alcohol having a specific chain length and a plasticizer B containing an isosorbide diester having a structure derived from a carboxylic acid having a specific chain length can solve the above problems. According to the present invention, it is possible to provide a plasticizer composition which is used in a halogen-based resin composition to give a halogen-based resin composition having excellent heat resistance. [Plasticizer composition] The plasticizer composition of the present invention is a plasticizer composition containing a plasticizer A composed of a phthalic acid diester having a structure derived from at least one alcohol selected from linear or branched aliphatic alcohols having a specific carbon number, and a plasticizer B containing an isosorbide diester having structures derived from linear or branched aliphatic carboxylic acids having different carbon numbers. The plasticizer composition of the present invention exerts an excellent effect on the heat resistance of the halogen-based resin composition. The reason why such an effect is exhibited is not clear, but it is considered as follows. The plasticizer composition of the present invention contains a plasticizer A composed of a phthalic acid diester having a structure derived from at least one alcohol selected from linear or branched aliphatic alcohols having 8 to 14 carbon atoms, and a plasticizer B containing an isosorbide diester having structures derived from linear or branched aliphatic carboxylic acids having two different carbon numbers. It is considered that when the plasticizer A is composed of a phthalic acid diester having a structure derived from at least one alcohol selected from linear or branched aliphatic alcohols having 8 to 14 carbon atoms, and the plasticizer B contains an isosorbide diester having structures derived from linear or branched aliphatic carboxylic acids having two different carbon numbers, a stronger interaction occurs between the phthalic acid diester and the is