Phenol-modified polyorganosiloxane with reduced platinum content, method for preparing the same, and modifier for organic resin containing the same

Patent metadata

Field	Value
Publication number	US-9512276-B2
Application number	US-201314440924-A
Country	US
Kind code	B2
Filing date	Nov 7, 2013
Priority date	Nov 7, 2012
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

A phenol-modified polyorganosiloxane suitable as a modifier for an organic resin, in which a platinum metal content is reduced, and the yellowing is reduced, a method for preparing the same, and a modifier for an organic resin containing the same are provided. The phenol-modified polyorganosiloxane is a compound of formula (I), having a platinum metal content of 0.9 ppm or less. The phenol-modified polyorganosiloxane can be prepared by subjecting a phenol compound substituted with an alkenyl group of formula (IV) and a polyorganohydrogen siloxane of formula (V) to a hydrosilation reaction in the presence of a platinum-based catalyst applicable to a homogenous system, and subsequently, reducing the platinum metal content of the resulting product to 0.9 ppm or less by conducting one or more filtration procedures selected from the group consisting of filtration conducted where activated carbon is added, filtration conducted by using a filter comprising activated carbon, and filtration conducted by using a filter capable of adsorbing cations, alone or in combination.

First claim

The invention claimed is:

1. A phenol-modified polyorganosiloxane represented by the following formula (I) and having a platinum metal content of 0.9 ppm or less:

wherein each R a independently represents a substituted or unsubstituted, and linear, branched or cyclic alkylene moiety; and R a is a substituted or unsubstituted C2-C20 alkylene moiety;
R and R′ are identical or different from one another, and each R and R′ independently represents a group selected from the group consisting of C1-C20 alkyl or halogenated alkyl groups and substituted or unsubstituted C6-C20 aryl groups;
each X independently represents a substituent selected from the group consisting of substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl groups; substituted or unsubstituted C6-C20 aryl groups; substituted or unsubstituted C6-C20 aryl C1-C20 alkyl groups (aralkyl groups); substituted or unsubstituted C1-C20 alkyloxy groups; substituted or unsubstituted C6-C20 aryloxy groups; substituted or unsubstituted C6-C20 aryl C1-C20 alkyloxy groups; and halogen atoms;
each m independently represents an integer ranging from 0 to 4;
n is a number ranging from 5 to 500; and
the substitution positions of the OH groups on the phenyl groups at both terminals of the molecule are each independently ortho, meta, or para position.

2. The phenol-modified polyorganosiloxane according to claim 1 , represented by the following formula (II) and having a platinum metal content of 0.9 ppm or less:

wherein each R and R′ independently represents a group selected from the group consisting of a methyl group, a phenyl group and a naphthyl group; n is a number ranging from 5 to 500; and each phenyl group at the terminals of the molecule independently represents o-OH, m-OH, or p-OH group.

3. The phenol-modified polyorganosiloxane according to claim 2 , represented by the following formula (III) and having a platinum metal content of 0.9 ppm or less:

wherein n is a number ranging from 5 to 500.

4. The phenol-modified polyorganosiloxane according to claim 3 , having a platinum metal content of 0.9 ppm or less and having a b* value of 1.10 or less measured by the L*a*b* color system defined in JIS Z 8729.

5. The phenol-modified polyorganosiloxane according to claim 2 , having a platinum metal content of 0.9 ppm or less and having a b* value of 1.10 or less measured by the L*a*b* color system defined in JIS Z 8729.

6. The phenol-modified polyorganosiloxane according to claim 1 , having a platinum metal content of 0.9 ppm or less and having a b* value of 1.10 or less measured by the L*a*b* color system defined in JIS Z 8729.

7. A resin composition comprising an aromatic polycarbonate resin which is modified with the phenol-modified polyorganosiloxane according to claim 1 .

8. A method comprising: using the phenol-modified polyorganosiloxane according to claim 1 as a modifier in order to reduce the yellowing of an aromatic polycarbonate resin composition.

9. A modifier for an organic resin comprising the phenol-modified polyorganosiloxane according to claim 1 , wherein the modifier comprises platinum metal in an amount of 0.9 ppm or less.

10. The modifier of claim 9 for improving a water-repellent property or improving a mold-releasing property of the organic resin.

11. A method for preparing a phenol-modified polyorganosiloxane represented by the following formula (I) and having a platinum metal content of 0.9 ppm or less:

wherein each R a independently represents a substituted or unsubstituted, and linear, branched or cyclic alkylene moiety; and R a is a substituted or unsubstituted C2-C20 alkylene moiety;
R and R′ are identical or different from one another, and each R and R′ independently represents a group selected from the group consisting of C1-C20 alkyl or halogenated alkyl groups and substituted or unsubstituted C6-C20 aryl groups;
each X independently represents a substituent selected from the group consisting of substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl groups; substituted or unsubstituted C6-C20 aryl groups; substituted or unsubstituted C6-C20 aryl C1-C20 alkyl groups (aralkyl groups); substituted or unsubstituted C1-C20 alkyloxy groups; substituted or unsubstituted C6-C20 aryloxy groups; substituted or unsubstituted C6-C20 aryl C1-C20 alkyloxy groups; and halogen atoms;
each m independently represents an integer ranging from 0 to 4;
n is a number ranging from 5 to 500; and
the substitution positions of the OH groups on the phenyl groups at both terminals of the molecule are each independently ortho, meta, or para position;

wherein the method comprises the steps of:
conducting hydrosilation reaction between a phenol compound substituted with an alkenyl group, represented by the following formula (IV):

wherein X and m are as defined above; R b represents an alkenyl group capable of producing the R a moiety defined above by the addition reaction with a polyorganohydrogensiloxane represented by formula (V):

wherein R, R′, and n are as defined above,

in the presence of one or more platinum-based catalysts selected from the group consisting of chloroplatinic acid, complexes of platinum with vinylsiloxanes, and platinum-olefin complexes in an amount of more than 0.9 ppm as platinum metal; and
reducing the platinum metal content of the resulting addition reaction product to 0.9 ppm or less by conducting one or more filtration procedures selected from the group consisting of filtration conducted where activated carbon is added, filtration conducted by using a filter comprising activated carbon, and filtration conducted by using a filter capable of adsorbing cations, alone or in combination.

12. The method of claim 11 , wherein the phenol-modified polyorganosiloxane is
represented by the following formula (III) and having a platinum metal content of 0.9 ppm or less:

wherein n is a number ranging from 5 to 500.

13. The method of claim 11 , when an unreacted compound of formula (IV) remains in the reaction product after conducting one or more filtration procedures selected from the group consisting of filtration conducted where activated carbon is added, filtration conducted by using a filter comprising activated carbon, and filtration conducted by using a filter capable of adsorbing cations, alone or in combination, further comprising a step of removing the unreacted compound of formula (IV) or reducing the amount thereof.

Assignees

• Dow Corning Toray Co Ltd

Inventors

• Sugiura Tsunehito
• Chayama Yasunori
• Matsuba Masashi

Classifications

• C08G64/42

  Chemical after-treatment · CPC title

• C08G64/18

  Block or graft polymers · CPC title

• C08G64/186

  containing polysiloxane sequences · CPC title

• C07F7/0879

  Hydrosilylation reactions · CPC title

• C08L83/04

  Polysiloxanes · CPC title