IP Library Granted Patent US 11,970,615
Granted Patent B2
US 11,970,615 · App. 17/600,846 · Granted Apr 30, 2024

Siloxane-containing block copolycarbonates having a small domain size

Inventors: Alexander Meyer (Düsseldorf, DE); Ulrich Liesenfelder (Bergisch Gladbach, DE); John Huggins (Bonn, DE)
Assignee: Covestro Intellectual Property GmbH & Co. KG
C08L83/10C08G77/448C08G77/80
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Quick Facts
Patent No.
US 11,970,615
App. No.
17/600,846
Granted
Apr 30, 2024
Kind
B2
Abstract

The present invention relates to a method for preparing a polysiloxane-polycarbonate block co-condensate, wherein a siloxane component containing both aliphatic and aromatic groups is used as a mediator. The invention also relates to a polycarbonate composition and also to the use of the special siloxane component for reducing the particle size distribution of the siloxane domains in a polysiloxane-polycarbonate block co-condensate.

Claims (81)

1. A polycarbonate composition containing

(i) at least one polysiloxane-polycarbonate block co-condensate,

(ii) at least one siloxane,

(iii) optionally at least one further polymer distinct from component (i) and

(iv) optionally at least one further additive,

wherein the at least one siloxane of component (ii) is represented by general chemical formula (II), general chemical formula (IIa), general chemical formula (III) and/or general chemical formula (IV)

in which Z 1 , Z 2 and Z 3 each independently of one another represent methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

R 10 independently at each occurrence represents hydrogen, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, isooctyl, isononyl or isodecyl,

R 11 independently at each occurrence represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

r is a natural number between 0 and 3,

s and t are each independently of one another a natural number between 1 and 250, and

w and v are each independently of one another a natural number between 1 and 250, and

groups having the indices s, w, v, t and u can have a random distribution in the siloxane of component (ii).

2. The polycarbonate composition as claimed in claim 1 , wherein in general chemical formulae (II), (IIa), (III) and (IV)

Z 1 , Z 2 and Z 3 each independently of one another represent methyl, vinyl, methoxy, ethoxy, hydrogen or hydroxy,

R 10 represents hydrogen or methyl,

R 11 independently at each occurrence represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

r is a natural number between 0 and 3,

s is a natural number between 5 and 75,

t is a natural number between 1 and 75,

w is a natural number between 5 and 75,

v is a natural number between 1 and 75 and

u is a natural number between 1 and 10.

3. The polycarbonate composition as claimed in claim 1 , wherein Z 1 , Z 2 and Z 3 each independently of one another represent methyl, methoxy, ethoxy, hydrogen, or hydroxy.

4. The polycarbonate composition as claimed in claim 1 , wherein Z 1 , Z 2 and Z 3 each independently of one another represent hydroxy.

5. The polycarbonate composition as claimed in claim 1 , wherein R 10 is hydrogen.

6. The polycarbonate composition as claimed in claim 1 , wherein s is a natural number between 1 and 100, t is a natural number between 1 and 75, w is a natural number between 5 and 75, v is a natural number between 1 and 75, and u is a natural number between 1 and 10.

7. The polycarbonate composition as claimed in claim 1 , wherein Z 1 , Z 2 and Z 3 each independently of one another represent methyl, methoxy, ethoxy, hydrogen, or hydroxy, wherein R 10 is hydrogen, and wherein s is a natural number between 1 and 100, t is a natural number between 1 and 75, w is a natural number between 5 and 75, v is a natural number between 1 and 75, and u is a natural number between 1 and 10.

8. The polycarbonate composition as claimed in claim 1 , wherein Z 1 , Z 2 and Z 3 each independently of one another represent hydroxy, wherein R 10 is hydrogen, and wherein s is a natural number between 1 and 100, t is a natural number between 1 and 75, w is a natural number between 5 and 75, v is a natural number between 1 and 75, and u is a natural number between 1 and 10.

9. A process for producing polysiloxane-polycarbonate block co-condensates, wherein

A) at least one polycarbonate is reacted in the melt with

B) at least one hydroxyaryl-terminated (poly)siloxane, wherein

C) at least one siloxane,

is added to the component A), to the component B) and/or to a mixture of component A) and B),

wherein the at least one siloxane is represented by general chemical formula (II), general chemical formula (IIa), general chemical formula (III) and/or general chemical formula (IV)

in which Z 1 , Z 2 and Z 3 each independently of one another represent methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

R 10 independently at each occurrence represents hydrogen, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, isooctyl, isononyl or isodecyl,

R 11 independently at each occurrence represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

r is a natural number between 0 and 3,

s and t are each independently of one another a natural number between 1 and 250, and

w and v are each independently of one another a natural number between 1 and 250, and

groups having the indices s, w, v, t and u can have a random distribution in the at least one siloxane.

10. The process for producing polysiloxane-polycarbonate block co-condensates as claimed in claim 9 , wherein

wherein component B) is a hydroxyaryl-terminated (poly)siloxane of formula (1),

wherein

R 5 represents hydrogen or C1 to C4 alkyl,

R 6 and R 7 independently of one another represent C1 to C4 alkyl,

Y represents a single bond, —CO—, —O—, C 1 - to C 5 -alkylene, C 2 - to C 5 -alkylidene or a C 5 - to C 6 -cycloalkylidene radical which may be mono- or polysubstituted by C 1 - to C 4 -alkyl,

V represents oxygen, C2-C6 alkylene or C3- to C6-alkylidene,

when q=0, W represents a single bond,

when q=1, W represents oxygen, C2 to C6-alkylene or C3- to C6-alkylidene,

p and q are each independently 0 or 1,

o represents an average number of repeating units from 10 to 400, and

m represents an average number of repeating units from 1 to 10.

11. The process for producing polysiloxane-polycarbonate block co-condensates as claimed in claim 9 , wherein

component B) is a hydroxyaryl-terminated (poly)siloxane of formulae (2), (3), (VII), (VIII) or (IX):

wherein R1 represents hydrogen, C1-C4-alkyl,

R2 independently represents aryl or alkyl,

X represents a single bond, C1 to C5-alkylene, C2 to C5-alkylidene, C5 to C12-cycloalkylidene, —O—, —SO— —CO—, —S—, —SO2-, isopropylidene, C5 to C12 cycloalkylidene or oxygen,

n is a number between 10 and 150,

m is a number from 1 to 10,

wherein a in formulae (VII), (VIII) and (IX) represents an average number from 10 to 400.

12. The process for producing polysiloxane-polycarbonate block co-condensates as claimed in claim 9 , wherein in general chemical formulae (II), (IIa), (III) and (IV)

Z 1 , Z 2 and Z 3 each independently of one another represent methyl, vinyl, methoxy, ethoxy, hydrogen or hydroxy,

R 10 represents hydrogen or methyl,

R 11 independently at each occurrence represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

r is a natural number between 0 and 3,

s is a natural number between 5 and 75,

t is a natural number between 1 and 75,

w is a natural number between 5 and 75 and

v is a natural number between 1 and 75.

13. The process for producing polysiloxane-polycarbonate block co-condensates as claimed in claim 9 , wherein 0.01% to 20% by weight of the component C) are added to the component A), to the component B) and/or to a mixture of component A) and B), wherein the % by weight values are based on the sum of the components A), B) and C).

14. A method for reducing a particle size distribution of siloxane domains in a polysiloxane-polycarbonate block co-condensate by providing the siloxane of general chemical formula (II), general chemical formula (IIa), general chemical formula (III) and/or general chemical formula (IV)

in which Z 1 , Z 2 and Z 3 each independently of one another represent methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

R 10 independently at each occurrence represents hydrogen, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, isooctyl, isononyl or isodecyl,

R 11 independently at each occurrence represents methyl, ethyl, propyl, butyl, isopropyl, isobutyl, vinyl, propenyl, butenyl, C5 to C18 alkyl, methacryloxypropyl; mono or dicarbinol, methoxy, ethoxy, propoxy, butoxy, epoxypropoxypropyl, optionally alkyl- or alkoxy-substituted phenylethyl, phenylisopropyl, 3-phenylpropyl or phenyl, hydroxy, hydrogen, chlorine, fluorine or CN,

r is a natural number between 0 and 3,

s and t are each independently of one another a natural number between 1 and 250, and

w and v are each independently of one another a natural number between 1 and 250, and

groups having the indices s, w, v, t and u can have a random distribution in the siloxane.

15. The method as claimed in claim 14 , wherein the process for producing the polysiloxane-polycarbonate block co-condensate comprises at least one reactive extrusion or at least one melt transesterification.

Assignments (2)
MERGER Recorded Oct 29, 2024
From: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 069272/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 1, 2021
From: MEYER, ALEXANDER; LIESENFELDER, ULRICH; HUGGINS, JOHN
To: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
Reel/Frame 057670/0380 →
Priority Claims (1)
EP 19166712 · Apr 2, 2019 · regional
Continuity (1)
Related Publication 20220195123A1 · Jun 23, 2022