Organopolysiloxanes and methods for preparing same

Patent metadata

Field	Value
Publication number	US-10358541-B2
Application number	US-201515537132-A
Country	US
Kind code	B2
Filing date	Dec 21, 2015
Priority date	Dec 22, 2014
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

The present invention concerns an organopolysiloxane (A) able to be obtained by the reaction, at a temperature of between 10° C. and 75° C., between—at least one compound (C) chosen from the organic compounds comprising at least one alkene or alkyne functional group, at least one of the substituents of which is an acid functional group and the organic compounds comprising at least one acid functional group and at least one alkene or alkyne functional group, at least one of the substituents of which is an electron-withdrawing group; and—at least one organopolysiloxane (B) chosen from the organopolysiloxanes comprising siloxyl units (I.1) and (I.2) of the following formulae: (I) The present invention also concerns compositions comprising said organopolysiloxanes (A) and the uses thereof.

(
I
)

Y
a

⁢

Z
b
1

⁢

SiO

4
-

(

a
+
b

)

2

;

(

I
⁢
.1

)

Z
c
2

⁢

SiO

4
-
c

2

(

I
⁢
.2

)

First claim

The invention claimed is:

1. An organopolysiloxane (A), comprising a filler, which may be obtained by reaction, at a temperature comprised between 10 and 75° C., between:
at least one compound (C) selected from the group consisting of the organic compounds comprising at least one alkene or alkyne function for which at least one of the substituents is an acid function and the organic compounds comprising at least one acid function and at least one alkene or alkyne function for which at least one of the substituents is an electroattractor group; and
at least one organopolysiloxane (B) selected from the group consisting of the organopolysiloxanes comprising siloxyl units (I.1) and (I.2) of the following formulae:

Y
a

⁢

Z
b
1

⁢

SiO

4
-

(

a
+
b

)

2

;
and

(

I
⁢
.1

)

Z
c
2

⁢

SiO

4
-
c

2

(

I
⁢
.2

)

wherein:
a=1 or 2, b=0, 1 or 2 and a+b=1, 2 or 3
c=1, 2, 3 or 4
the symbols Y, either identical or different, represent a functional group of formula (I.3):
-E-(NH-G) h -(NH 2 ) i   (I.3)

wherein:
h=0 or 1;
i=0 or 1;
h+i=1 or 2;
E represents an aliphatic, cycloaliphatic or aromatic divalent hydrocarbon comprising from 1 to 30 carbon atoms;
when it is present, G represents an aliphatic hydrocarbon radical comprising from 1 to 10 carbon atoms, monovalent when i=0 or divalent when i=1;
the symbols Z 1 and Z 2 , either identical or different, represent a monovalent hydrocarbon radical having from 1 to 30 carbon atoms and optionally comprising one or several unsaturations and/or one or several fluorine atoms, a hydroxyl group, or a radical-OR 1 with R 1 which represents a linear, cyclic or branched C 1 -C 10 hydrocarbon radical;

said polyorganosiloxane (B) comprising, per molecule, at least one siloxyl unit (I.1) bearing at least one functional group of formula (I.3),
the reaction being made in the presence of a filler.

2. The organopolysiloxane (A) according to claim 1 wherein the temperature is comprised between 10 and 70° C.

3. The organopolysiloxane (A) according to claim 1 , wherein the compound (C) is selected from among the organic compounds comprising at least a double carbon-carbon bond for which at least one of the substituents is a carboxylic acid function.

4. The organopolysiloxane (A) according to claim 1 , wherein the compound (C) is selected from among the compounds of formula (II)

wherein:
R 2 , R 3 and R 4 , either identical or different, represent a hydrogen atom, a COOH group or a C 1 -C 6 ;
R 5 represents a hydrogen atom, an alkyl group or an aryl group, wherein the alkyl and the aryl comprise at least one COOH group.

5. The organopolysiloxane (A) according to claim 1 , wherein the compound (C) is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, crotonic acid, 2-carboxyethylacrylate, 3-carboxypropylacrylate, maleic acid, fumaric acid, 2-(acryloyloxy)acetic acid, 2-(acryloyloxy)propanoic acid, 3-(acrylolyloxy)propanoic acid, 2-(acryloyloxy)-2-phenylacetic acid, 4-(acryloyloxy)butanoic acid, 2-(acryloyloxy)-2-methylpropanoic acid, 5-(acryloyloxy)pentanoic acid, (E)-but-2-enoic acid, (Z)-prop-1-ene-1,2,3-tricarboxylic acid, cinnamic acid, sorbic acid, 2-hexenoic acid, 2-pentenoic acid, 2,4-pentadienoic acid, ethenesulfonic acid, vinylphosphonic acid, (1-phenylvinyl)phosphonic acid, 3-(vinylsulfonyl)propanoic acid, 2-(vinylsulfonyl)acetic acid, 2-(vinylsulfonyl)succinic acid, acetylene dicarboxylic acid and propiolic acid.

6. The organopolysiloxane (A) according to claim 1 , wherein the organopolysiloxane (B) is selected from the group consisting of the organopolysiloxanes comprising siloxyl units (I.1) and (I.2) of the following formulae:

Y
a

⁢

Z
b
1

⁢

SiO

4
-

(

a
+
b

)

2

;
and

(

I
⁢
.1

)

Z
c
2

⁢

SiO

4
-
c

2

Assignees

• Elkem Silicones France Sas
• Institut Nat Des Sciences Appliquees Lyon
• Univ Claude Bernard Lyon
• Centre Nat Rech Scient
• Univ Jean Monnet Saint Etienne

Inventors

• Ganachaud François
• Fleury Etienne
• Portinha De Almeida Daniel
• Genest Aymeric
• Pouget Emmanuel

Classifications

• C08K3/36 Primary

  Silica · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08K5/09 Primary

  Carboxylic acids; Metal salts thereof; Anhydrides thereof · CPC title

• C08G77/26 Primary

  nitrogen-containing groups · CPC title