Method for producing polycarbonate-polyorganosiloxane copolymer

Patent metadata

Field	Value
Publication number	US-10472518-B2
Application number	US-201615754776-A
Country	US
Kind code	B2
Filing date	Aug 29, 2016
Priority date	Aug 27, 2015
Publication date	Nov 12, 2019
Grant date	Nov 12, 2019

Abstract

Provided is a method of producing a polycarbonate-polyorganosiloxane copolymer, including a step (Q) of causing a polycarbonate oligomer and at least one of polyorganosiloxanes represented by the following general formulae (i) to (iii) to react with each other in an organic solvent, in which in the step, a solid content weight x (g/L) of the polycarbonate oligomer in 1 L of a mixed solution of the organic solvent and the polycarbonate oligomer, a concentration y (mass %) of the polyorganosiloxane in the polycarbonate-polyorganosiloxane copolymer to be obtained, and a chain length n of the polyorganosiloxane satisfy specific conditions.

First claim

The invention claimed is:

1. A method of producing a polycarbonate-polyorganosiloxane copolymer, comprising a step (Q) of causing a polycarbonate oligomer and at least one of polyorganosiloxanes represented by the following general formulae (i) to (iii) to react with each other in an organic solvent, wherein in the step, a solid content weight x (g/L) of the polycarbonate oligomer in 1 L of a mixed solution of the organic solvent and the polycarbonate oligomer, a concentration y (mass %) of the polyorganosiloxane in the polycarbonate-polyorganosiloxane copolymer to be obtained, and a chain length n of the polyorganosiloxane satisfy any one of conditions described by following formulae (I-I), (I-II), (I-III), (II-I), (II-II), (II-III), (III-I), and (IV-I):
36≤ n< 75,15≤ y< 26,80≤ x< 190,  (I-I):

36≤ n< 75,26≤ y≤ 35,80≤ x≤ 170,  (I-II):

36≤ n< 75,35< y≤ 50,80≤ x≤ 130,  (I-III):

75≤ n≤ 110,10≤ y< 20,80≤ x≤ 190,  (II-I):

75≤ n≤ 110,20≤ y≤ 30,80≤ x≤ 145,  (II-II):

75≤ n≤ 110,30< y≤ 50,80≤ x≤ 130,  (II-III):

110< n≤ 200,5≤ y≤ 15,130≤ x≤ 185,  (III-I):

200< n≤ 350,5≤ y≤ 10,130≤ x≤ 185  (IV-I):

wherein R 3 to R 6 each independently represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 carbon atoms, and a plurality of R 3 , R 4 , R 5 or R 6 may be identical to or different from each other, Y represents —R 7 O—, —R 7 COO—, —R 7 NH—, —R 7 NR 8 —, —COO—, —S—, —R 7 COO—R 9 —O—, or —R 7 O—R 10 —O—, and a plurality of Y may be identical to or different from each other, the R 7 represents a single bond, a linear, branched or cyclic alkylene group, an aryl-substituted alkylene group, a substituted or unsubstituted arylene group, or a diarylene group, R 8 represents an alkyl group, an alkenyl group, an aryl group, or an aralkyl group, R 9 represents a diarylene group, R 10 represents a linear, branched, or cyclic alkylene group, or a diarylene group, Z represents a hydrogen atom or a halogen atom, and a plurality of Z may be identical to or different from each other, β represents a divalent group derived from a diisocyanate compound, or a divalent group derived from a dicarboxylic acid or a halide of a dicarboxylic acid, n represents the chain length of the polyorganosiloxane, and n−1, and p and q each represent a number of repetitions of a polyorganosiloxane unit and each represent an integer of 1 or more, and a sum of p and q is n−2.

2. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein in the step (Q), the solid content weight x (g/L) of the polycarbonate oligomer in 1 L of the mixed solution of the organic solvent and the polycarbonate oligomer, the concentration y (mass %) of the polyorganosiloxane in the polycarbonate-polyorganosiloxane copolymer to be obtained, and the chain length n of the polyorganosiloxane satisfy the following mathematical formula (1)
−2.0×10 −5 x 3 +1.1×10 −5 nx 2 +1.5×10 −4 yx 2 −6.0×10 −7 n 2 x− 1.6×10 −4 y 2 x− 2.8×10 −5 nyx− 18.8≤0  (1).

3. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein in the step (Q), the chain length n of the polyorganosiloxane and the concentration y (mass %) of the polyorganosiloxane in the polycarbonate-polyorganosiloxane copolymer to be obtained satisfy the following mathematical formula (2)
n×y≥ 1100  (2).

4. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the polycarbonate oligomer has a weight-average molecular weight of from 1,500 to 2,900.

5. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the step (Q) comprises adding a polymerization catalyst so that a molar ratio of the polymerization catalyst to a chloroformate is 0.001 or more to 0.02 or less.

6. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the step (Q) comprises adding aqueous sodium hydroxide so that a molar ratio of sodium hydroxide to a chloroformate is 0.10 or more to 0.75 or less.

7. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the method comprises further adding a dihydric phenol after the step (Q).

8. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the method comprises performing a polymerization reaction after the step (Q) while keeping a temperature at from 20° C. to 40° C.

9. The method of producing a polycarbonate-polyorganosiloxane copolymer according to claim 1 , wherein the polycarbonate-polyorganosiloxane copolymer to be obtained has a viscosity-average molecular weight of from 9,000 to 50,000.

10. A method of producing a polycarbonate-based resin composition, comprising mixing a polycarbonate-polyorganosiloxane copolymer (A) obtained by the production method of claim 1 and a polycarbonate-based resin (B) except the polycarbonate-polyorganosiloxane copolymer (A).

11. The method of producing a polycarbonate-based resin composition according to claim 10 , wherein a weight ratio “(A)/(B)” of the polycarbonate-polyorganosiloxane copolymer (A) to the polycarbonate-based resin (B) is from 1/99 to 83/17.

12. The method of producing a polycarbonate-based resin composition according to claim 10 , wherein the polycarbonate-based resin composition to be obtained has a viscosity-average molecular weight of from 9,000 to 50,000.

13. The method of producing a polycarbonate-based resin composition according to claim 10 , wherein a polyorganosiloxane chain length (n) and a polyorganosiloxane concentration (y′) (mass %) in the resin composition satisfy the following mathematical formula (3)
n×y′≤ 1000  (3).

14. The method of producing a polycarbonate-based resin composition according to claim 10 , wherein the polycarbonate-based resin (B) comprises an aromatic homopolycarbonate.

Assignees

• Idemitsu Kosan Co

Inventors

• Abe Tomoko
• Ishikawa Yasuhiro
• Koori Yohei
• Nakagawa Masaru

Classifications

• C08G64/24

  and phenols · CPC title

• C08G64/186

  containing polysiloxane sequences · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08G81/00

  Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42}) · CPC title

• C08G77/448 Primary

  containing polycarbonate sequences · CPC title