# US 5,705,591 A · Room temperature curable fluoropolymer composition; and fluorine-containing organosilicon compounds, a method of producing the same, and room temperature curable silicone composition containing the same

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- Number: US 5,705,591 A
- Document ID: US5705591A
- Status: Granted
- Kind: A
- Application number: 08/654,637
- Filed: 1996-05-29
- Granted: 1998-01-06
- Earliest claimed: 1995-05-29
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Inventors: Takashi Matsuda; Takafumi Sakamoto; Shinichi Sato; Noriyuki Koike; Yasuo Tarumi; Tsuneo Kimura; Yasushi Yamamoto; Masatoshi Arai
- Web page: https://patentgrep.com/patent/US5705591A

## CPC

- C08G 65/007: {containing fluorine}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07F 7/1896: {Compounds having one or more Si-O-acyl linkages}
- C07F 7/21: Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
- C08G 65/336: containing silicon
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

A room temperature curable fluoropolymer composition is provided which comprises (A) a straight chain fluoropolymer compound containing, in its backbone chain, at least one structure selected from a perfluoroalkylene structure and a perfluoropolyether structure and having a hydrolyzable silyl group at both ends of its molecular chain, (B) an organic compound having at least one carbonyl group per molecule, and (C) one compound selected from (C-1) an organic compound having at least one primary amino group per molecule and (C-2) a compound having at least one proton per molecule and having an acid dissociation constant (pKa) in water of 2 or less. Another room temperature curable composition is also provided which comprises said (A) component, (B') an organosilicon compound having at least two silanol groups per molecule, and (C') a condensation accelerator. These compositions are not only excellent in heat resistance, weatherability, electrical properties, processability, chemical resistance, solvent resistance and oil repellant properties, but also excellent in fast curability and deep-portion curability. A novel compound which is suitable as said fluoropolymer compound (A) is further provided.

## Claims

### Claim 1

A fluorine-containing organosilicon compound having the formula (8): ##STR71## wherein R.sup.8 and R.sup.9 are independently a monovalent group selected from the group consisting of alkyl, cycloalkyl, aryl, aralkyl, alkenyl, acryloyloxypropyl, methacryloxypropyl and a substituted group obtained by substituting at least part of hydrogen atoms contained in these groups with a halogen atom;
R.sup.10 is independently a hydrogen atom or a monovalent group as defined for R.sup.8 and R.sup.9 ;
R.sup.11 is independently a divalent group selected from the group consisting of alkylene, arylene, a substituted group obtained by substituting at least part of hydrogen atoms contained in these groups with a halogen atom, and a combination thereof;
Rf is independently a divalent perfluoroalkylene group or a divalent perfluoropolyether group;
X is independent a hydrolyzable group;
Q is a group of the formula (9): ##STR72## wherein R.sup.10 is as defined in formula (8), and R.sup.12 is a divalent group as defined for R.sup.11 in formula (8), a group represented by the formulae: ##STR73## wherein in said formulae Me is methyl, or a group represented by the formula (10): ##STR74## wherein R.sup.13 and R.sup.14 are independently a divalent group as defined by R.sup.11 in formula (8);
a is an integer of 0 or more; and
b is 1, 2 or 3.

### Claim 2 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.8, R.sup.9 or R.sup.10 is C.sub.1 -C.sub.10 alkyl.

### Claim 3 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.8, R.sup.9 or R.sup.10 is C.sub.3 -C.sub.8 cycloalkyl.

### Claim 4 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.8, R.sup.9 or R.sup.10 is C.sub.6 -C.sub.15 aryl.

### Claim 5 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.8, R.sup.9 or R.sup.10 is C.sub.7 -C.sub.10 aralkyl.

### Claim 6 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.8, R.sup.9 or R.sup.10 is C.sub.7 -C.sub.10 alkenyl.

### Claim 7 (depends on 1)

The fluorine-containing organosilicon compound of claim 1, wherein R.sup.11 is C.sub.1 -C.sub.20 alkylene.

### Claim 8 (depends on 1)

A process of producing the fluorine-containing organosilicon compound of claim 1, which comprises reacting an organosilicon compound having the following formula (11): ##STR75## wherein R.sup.9 a monovalent group selected from the group consisting of alkyl, cycloalkyl aryl, aralkyl, alkenyl, acryloyloxypropyl, methacroyloxypropyl and a substituted group obtained by substituting at least part of hydrogen atoms contained in these groups with a halogen atom;
R.sup.10 is independently a hydrogen atom or a monovalent group as defined for R.sup.9 ;
R.sup.15 is independently an alkenyl group having 2 to 8 carbon atoms;
Rf is independently a divalent perfluoroalkylene group or a divalent perfluoropolyether group;
Q is a group of the formula (9): ##STR76## wherein R.sup.12 is a divalent group selected form the group consisting of alkylene, arylene, a substituted group obtained by substituting at least part of hydrogen atoms contained in these groups with a halogen atom;
wherein R.sup.10 is as defined above or having the formula: ##STR77## wherein R.sup.13 and R.sup.14 are independently a divalent group selected from the group consisting of alkylene, arylene, an unsubstituted group obtained by substituting at least part of hydrogen atom contained in these groups with a halogen atoms, and a combination thereof;
a is an integer of 0 or more;
with an organohydrogen silane having the formula (12): ##STR78## wherein R.sup.8 is as defined for R.sup.9 above; X is a hydrolyzable group, and b is 1, 2 or 3, in the presence of a hydrosilylation catalyst.

### Claim 9 (depends on 8)

The process of claim 8, wherein the amount of the organohydrogen silane having the formula (12) is in the range of 2 to 10 mols per mol of the organosilicon compound having the formula (11), and the reaction temperature is in the range of about 50.degree. C. to 150.degree. C.

### Claim 10 (depends on 1)

A room temperature curable silicone composition comprising the fluorine-containing organosilicon compound of claim 1 and a curing reaction accelerating catalyst.