UV-active chromophore functionalized polysiloxanes and copolymers made therefrom

Patent metadata

Field	Value
Publication number	US-9562159-B2
Application number	US-201514790464-A
Country	US
Kind code	B2
Filing date	Jul 2, 2015
Priority date	Jul 3, 2014
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

Disclosed herein is a polyorganosiloxane having the structure of Formula I:

wherein, R 1 and R 2 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical. R 3 is an organic UV absorbing group, R 4 independently is a direct bond, hydrocarbon radical optionally substituted with oxygen and nitrogen, or a group of Formula II(a) or Formula II(b)

wherein A and B are a hydrocarbon radical, R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group, R 6 is independently a hydroxyl group, an amine group, an acid chloride group, or a sulfonyl halide group, x is from 1 to 300, y is from 0 to 50 and z is from 1 to 50. The polyorganosiloxane is used to make various copolymers or polymer blends. A variety of articles can be made using the polysiloxane described as a polymer blend or copolymer.

First claim

What is claimed is:

1. A polysiloxane comprising a structure of Formula I:

wherein; R 1 and R 2 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; R 3 is an organic UV absorbing group derived from an allyl substituted 2-hydroxybenzophenone, allyl substituted 2-hydroxy-4-methoxybenzophenone, allyl substituted 2-hydroxy-4-methoxy-2′-carboxybenzophenone, allyl substituted 2,4-dihydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxybenzophenone, allyl substituted 2,2′-dihydroxybenzophenone, allyl substituted 2,2′,4,4′-tetrahydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-diethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dipropoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dibutoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-ethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-propoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-butoxybenzophenone or allyl substituted dibenzoylresorcinol; R 4 is independently a hydrocarbon radical optionally substituted with oxygen and nitrogen, or a group of Formula II(a) or Formula II(b)

wherein A and B are a hydrocarbon radical; R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; R 6 is a hydroxyl group; x is from 1 to 300; y is from 0 to 50 and z is from 1 to 50.

2. A method of preparing the polysiloxane of claim 1 comprising:
reacting a hydride terminated siloxane represented by Formula III;

wherein R 1 and R 2 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; wherein x is from 1 to 300 and y is from 0 to 50; with an allyl unsaturated chain containing substituted or unsubstituted hydroxyphenyl compound followed by equilibration of hydroxyphenyl compound terminated siloxane in presence of hydride substituted cyclic siloxane to obtain a hydroxyphenyl compound terminated siloxane having the formula:

wherein R 1 and R 2 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; R 4 is independently a hydrocarbon radical optionally substituted with oxygen and nitrogen, or a group of Formula II(a) or Formula II(b)

wherein A and B are a hydrocarbon radical; R 5 is independently a hydrogen, a halogen, an aliphatic group having from 1 to 6 carbon atoms, an aromatic group having 6 to 8 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms, or an aryloxy group; R 6 is independently a hydroxyl group; wherein x is from 1 to 300; y is from 0 to 50; and z is from 0 to 50;
reacting the hydroxyphenyl compound terminated siloxane with an allyl substituted 2-hydroxy-4-methoxybenzophenone, allyl substituted 2-hydroxy-4-methoxy-2′-carboxybenzophenone, allyl substituted 2,4-dihydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxybenzophenone, allyl substituted 2,2′-dihydroxybenzophenone, allyl substituted 2,2′,4,4′-tetrahydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-diethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dipropoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dibutoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-ethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-propoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-butoxybenzophenone or allyl substituted dibenzoylresorcinol in the presence of a catalyst at a temperature of about 50 to 80° C., to yield the UV absorbing polysiloxane; and
purifying the UV absorbing polysiloxane.

3. The polysiloxane of claim 1 , wherein R 3 the organic UV absorbing group derived from an allyl substituted 2-hydroxy-4-methoxybenzophenone, allyl substituted 2-hydroxy-4-methoxy-2′-carboxybenzophenone, allyl substituted 2,4-dihydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxybenzophenone, allyl substituted 2,2′-dihydroxybenzophenone, allyl substituted 2,2′,4,4′-tetrahydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-diethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dipropoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dibutoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-ethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-propoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-butoxybenzophenone.

4. The polysiloxane of claim 1 , wherein R 3 is the organic UV absorbing group derived from an allyl substituted compound of Formula IV:

5. The polysiloxane of claim 1 , wherein R 3 is the organic UV absorbing group derived from an allyl substituted compound of Formula V:

6. A composition comprising the polysiloxane of claim 1 and a polymer selected from the group consisting of: polycarbonate homopolymers, polycarbonate copolymers, polycarbonate-polyesters, polyesters, polysulfones, polyethersulfones, polyetheretherketones, polyimides and polyetherimides.

7. An article comprising the polyosiloxane of claim 6 .

8. A copolymer comprising at least one polysiloxane having units of Formula VI represented by:

wherein; R 1 and R 2 are independently a hydrocarbon radical, an unsaturated radical, an alkoxy radical, an aryl radical or an alkenyloxy radical; R 3 is an organic UV absorbing group derived from an allyl substituted 2-hydroxybenzophenone, allyl substituted 2-hydroxy-4-methoxybenzophenone, allyl substituted 2-hydroxy-4-methoxy-2′-carboxybenzophenone, allyl substituted 2,4-dihydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxybenzophenone, allyl substituted 2,2′-dihydroxybenzophenone, allyl substituted 2,2′,4,4′-tetrahydroxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dimethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-diethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dipropoxybenzophenone, allyl substituted 2,2′-dihydroxy-4,4′-dibutoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-ethoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-propoxybenzophenone, allyl substituted 2,2′-dihydroxy-4-methoxy-4′-butoxybenzophenone, allyl substituted 2-(2′-hydroxy-5′-methylphenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydroxy-5′-tert.-butylphenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydroxy-3′-methyl-5′-tert.-butyl-phenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydroxy-5′-cyclohexyl-phenyl)-2H-benzotriazole, allyl substituted 2′-(2′-hydroxy-3′,5′-dimethyl-phenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydroxy-5′-isooctylphenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydroxy-3′-tert.-butyl-5′-sec.-butylphenyl)-2H-benzotriazole, allyl substituted 2-(2′-hydr

Assignees

• Momentive Performance Mat Inc
• Momentive Performance Mat Inc

Inventors

• Iyer Narayana Padmanabha
• Ramakrishnan Indumathi
• Rojas-Wahl Roy
• Alam Samim

Classifications

• C08G77/14 Primary

  containing silicon bound to oxygen-containing groups · CPC title

• C08G77/12

  containing silicon bound to hydrogen · CPC title

• C08G77/80

  Siloxanes having aromatic substituents, e.g. phenyl side groups · CPC title

• C08G77/448

  containing polycarbonate sequences · CPC title

• C08L83/10 Primary

  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