Polysiloxane-polycarbonate copolymer using hydroxy-terminated polysiloxane mixture, and method for producing same

Patent metadata

Field	Value
Publication number	US-12378364-B2
Application number	US-202117917278-A
Country	US
Kind code	B2
Filing date	Apr 22, 2021
Priority date	Apr 24, 2020
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

The present invention relates to a polysiloxane-polycarbonate copolymer using a hydroxyl terminated polysiloxane mixture, and a method for producing same, and more specifically, to: a polysiloxane-polycarbonate copolymer which includes hydroxy-terminated polysiloxanes of chemical formulae 1 and 2 in a specific weight ratio as repeating units, and thus exhibits excellent transmittance and low-temperature impact strength compared to the case of using either of the hydroxy-terminated polysiloxanes by itself, and in which the overall production yield of the raw material polysiloxane is improved, such that the polysiloxane-polycarbonate copolymer is excellent in terms of economics; and a method for producing same.

First claim

The invention claimed is:

1. A polysiloxane-polycarbonate copolymer comprising:
as repeating units, a hydroxyl-terminated polysiloxane of the following chemical formula 1; a hydroxyl-terminated polysiloxane of the following chemical formula 2; and a polycarbonate block;
wherein total 100 parts by weight of the hydroxyl-terminated polysiloxanes of chemical formulas 1 and 2 consists of 1 to 39 parts by weight of the hydroxyl-terminated polysiloxane of chemical formula 1 and 61 to 99 parts by weight of the hydroxyl-terminated polysiloxane of chemical formula 2:

wherein: in the above chemical formulas 1 and 2,
each R 1 independently represents hydrogen atom, halogen atom, hydroxy group, an alkyl group, an alkoxy group, or an aryl group;
each R 2 independently represents a hydrocarbon group having 1 to 13 carbon atoms, or hydroxy group;
each R 3 independently represents an alkylene group having 2 to 8 carbon atoms;
A represents a substituted or unsubstituted divalent hydrocarbon group comprising one or more groups selected from ester group, ether group, thioether group, ketone group or urethane group;
l represents an integer of 0 to 4; and
each of m and n independently represents an integer of 2 to 1,000.

2. The polysiloxane-polycarbonate copolymer of claim 1 , wherein: in chemical formulas 1 and 2,
each R 1 independently represents hydrogen atom, halogen atom, hydroxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms;
each R 2 independently represents a hydrocarbon group having 1 to 13 carbon atoms, or hydroxy group;
each R 3 independently represents an alkylene group having 2 to 8 carbon atoms;
A represents

where Y is X or NH—X—NH, wherein X is a linear or branched aliphatic group having 1 to 20 carbon atoms; a cycloalkylene group having 3 to 20 carbon atoms; or a mononucleus or polynucleus arylene group having 6 to 30 carbon atoms which is unsubstituted or substituted with halogen atom, alkyl group, alkoxy group, aryl group or carboxyl group;
l represents an integer of 0 to 4; and
each of m and n independently represents an integer of 2 to 1,000.

3. The polysiloxane-polycarbonate copolymer of claim 1 , wherein n in chemical formula 1 is an integer of 11 to 40, and m in chemical formula 2 is an integer of 20 to 80.

4. The polysiloxane-polycarbonate copolymer of claim 1 , wherein the polycarbonate block has a structure represented by the following chemical formula 3:

wherein: in the above chemical formula 3,
R 4 represents an aromatic hydrocarbon group having 6 to 30 carbon atoms which is unsubstituted or substituted with alkyl group, cycloalkyl group, alkenyl group, alkoxy group, halogen atom or nitro group.

5. The polysiloxane-polycarbonate copolymer of claim 4 , wherein the aromatic hydrocarbon group of R 4 in chemical formula 3 is derived from a compound of the following chemical formula 4:

wherein: in the above chemical formula 4,
L represents a linear, branched or cyclic alkylene group having no functional group; or a linear, branched or cyclic alkylene group comprising at least one functional group selected from the group consisting of sulfide group, ether group, sulfoxide group, sulfone group, ketone group, naphthyl group or isobutylphenyl group,
each of R 5 and R 6 independently represents halogen atom; or a linear, branched or cyclic alkyl group, and
each of p and q independently represents an integer of 0 to 4.

6. The polysiloxane-polycarbonate copolymer of claim 1 , wherein the sum of amounts of the hydroxyl-terminated polysiloxane of chemical formula 1 and the hydroxyl-terminated polysiloxane of chemical formula 2 is 3 to 39% by weight, based on the total weight of the polysiloxane-polycarbonate copolymer.

7. The polysiloxane-polycarbonate copolymer of claim 1 , which has a viscosity average molecular weight of 13,000 to 69,000 g/mol.

8. A method for preparing a polysiloxane-polycarbonate copolymer, comprising the steps of:
(1) reacting a hydroxyl-terminated polysiloxane of the following chemical formula 1, a hydroxyl-terminated polysiloxane of the following chemical formula 2 and an oligomeric polycarbonate under an interfacial reaction condition to form a polysiloxane-polycarbonate intermediate; and
(2) polymerizing the polysiloxane-polycarbonate intermediate by using a first polymerization catalyst;
wherein total 100 parts by weight of the hydroxyl-terminated polysiloxanes of chemical formulas 1 and 2 consists of 1 to 39 parts by weight of the hydroxyl-terminated polysiloxane of chemical formula 1 and 61 to 99 parts by weight of the hydroxyl-terminated polysiloxane of chemical formula 2:

wherein: in the above chemical formulas 1 and 2,
each R 1 independently represents hydrogen atom, halogen atom, hydroxy group, an alkyl group, an alkoxy group, or an aryl group;
each R 2 independently represents a hydrocarbon group having 1 to 13 carbon atoms, or hydroxy group;
each R 3 independently represents an alkylene group having 2 to 8 carbon atoms;
A represents a substituted or unsubstituted divalent hydrocarbon group comprising one or more groups selected from ester group, ether group, thioether group, ketone group or urethane group;
l represents an integer of 0 to 4; and
each of m and n independently represents an integer of 2 to 1,000.

9. The method for preparing a polysiloxane-polycarbonate copolymer of claim 8 , wherein the step (1) of forming a polysiloxane-polycarbonate intermediate comprises a step of mixing a mixture of the hydroxyl-terminated polysiloxane of chemical formula 1 and the hydroxyl-terminated polysiloxane of chemical formula 2, and the oligomeric polycarbonate with a weight ratio of 3:97 to 39:61.

10. The method for preparing a polysiloxane-polycarbonate copolymer of claim 8 , wherein the step (1) of forming a polysiloxane-polycarbonate intermediate comprises a step of forming a mixture comprising the hydroxyl-terminated polysiloxane of chemical formula 1, the hydroxyl-terminated polysiloxane of chemical formula 2 and the oligomeric polycarbonate; and the mixture further comprises a phase transfer catalyst, a molecular weight-controlling agent and a second polymerization catalyst.

11. The method for preparing a polysiloxane-polycarbonate copolymer of claim 8 , wherein:
the step (1) of forming a polysiloxane-polycarbonate intermediate comprises a step of forming a mixture comprising the hydroxyl-terminated polysiloxane of chemical formula 1, the hydroxyl-terminated polysiloxane of chemical formula 2 and the oligomeric polycarbonate; and after completion of the reaction of the hydroxyl-terminated polysiloxanes of formulas 1 and 2 and the oligomeric polycarbonate, a step of extracting an organic phase from the resulting mixture, and
the step (2) of polymerizin

Assignees

• Samyang Corp

Inventors

• Chang Yun Ju
• Shin Kyung Moo
• Kang Ki Tae
• Kim Mi Ran
• Jung Seung Pil
• Choi Jin Sik
• Heo Seong Hyen

Classifications

• C08L83/10

  Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00) · CPC title

• C08G64/186 Primary

  containing polysiloxane sequences · CPC title

• C08G77/458

  containing polyurethane sequences · CPC title

• C08L69/00

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

• C08G77/50

  by carbon linkages · CPC title