# US 5,705,586 A · Organic fluorine compounds and curable compositions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 5,705,586 A
- Document ID: US5705586A
- Status: Granted
- Kind: A
- Application number: 08/494,566
- Filed: 1995-06-22
- Granted: 1998-01-06
- Earliest claimed: 1994-06-23
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Inventors: Shinichi Sato; Noriyuki Koike; Takashi Matsuda; Hirofumi Kishita; Masatoshi Arai
- Web page: https://patentgrep.com/patent/US5705586A

## CPC

- C07D 295/185: from aliphatic carboxylic acids
- C07C 235/08: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07F 7/21: Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
- C08G 65/007: {containing fluorine}
- C08G 65/336: containing silicon
- C08G 69/42: Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen (C08G69/12, C08G69/32 take precedence)
- C08G 77/46: containing polyether sequences
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Novel organic fluorine compounds are of formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are monovalent hydrocarbon groups, Q.sup.1 is a group of formula (2) or (3): ##STR2## wherein R.sup.3 is a divalent hydrocarbon group which may have an intervening oxygen, nitrogen or silicon atom, R.sup.4 and R.sup.5 are divalent hydrocarbon groups, Rf.sup.1 is a divalent perfluoroalkylene or perfluoropolyether group, and letter a is an integer of 0-10. A curable composition comprising (A) a fluorinated amide compound having at least two aliphatic unsaturated groups of formula (1), (B) a fluorinated organohydrogensiloxane containing at least one monovalent perfluoroalkyl ether or perfluoroalkyl group and at least two hydrosilyl groups, and (C) a platinum group compound cures into elastomers solvent and chemical resistance.

## Claims

### Claim 1

An organic fluorine compound of the following general formula: ##STR46## wherein R.sup.1 are independently selected from substituted or unsubstituted monovalent hydrocarbon groups having an aliphatic unsaturated group,
R.sup.2 are independently selected from the substituted or unsubstituted monovalent hydrocarbon groups,
Q.sup.1 is a group represented by the following general formula (2) or (3): ##STR47## wherein R.sup.3 is a substituted or unsubstituted divalent hydrocarbon group which may have at least one intervening atom selected from oxygen, nitrogen and silicon atoms, R.sup.4 and R.sup.5 are independently selectcd from substituted or unsubstituted divalent hydrocarbon groups,
Rf.sup.1 is a divalent perfluoroalkylene or perfluoropolyether group, and
letter a is an integer inclusive of 0.

### Claim 2

A curable composition comprising
(A) a fluorinated amide compound having at least two aliphatic unsaturated groups in a molecule and represented by the following general formula (1): ##STR48## wherein R.sup.1 are independently selected from substituted or unsubstituted monovalent hydrocarbon groups having an aliphatic unsaturated group,
R.sup.2 are independently selected from the substituted or unsubstituted monovalent hydrocarbon groups,
Q.sup.1 is a group represented by the following general formula (2) or (3): ##STR49## wherein R.sup.3 is a substituted or unsubstituted divalent hydrocarbon group which may have at least one intervening atom selected from oxygen, nitrogen and silicon atoms, R.sup.4 and R.sup.5 are independently selected from substituted or unsubstituted divalent hydrocarbon groups,
Rf.sup.1 is a divalent perfluoroalkylene or perfluoropolyether group, and
letter a is an integer inclusive of 0,
(B) a fluorinated organohydrogensiloxane containing at least one monovalent perfluoroalkyl ether or perfluoroalkyl group and at least two hydrosilyl groups in a molecule, and
(C) a catalytic amount of a platinum group compound, component (B) being present in an amount to give 0.5 to 5 mol of the hydrosilyl group per mol of the aliphatic unsaturated group in the composition.

### Claim 3

A curable composition comprising
(D) a fluorinated amide compound having at least two aliphatic unsaturated groups in a molecule and represented by the following general formula (4): ##STR50## wherein R.sup.1 is a substituted or unsubstituted monovalent hydrocarbon group having an aliphatic unsaturated group,
Q.sup.2 is a group represented by the following general formula (5): ##STR51## wherein R.sup.3 is a substituted or unsubstituted divalent hydrocarbon group which may have at least one intervening atom selected from oxygen, nitrogen and silicon atoms,
Rf.sup.1 is a divalent perfluoroalkylene or perfluoropolyether group, and
letter a is an integer inclusive of 0,
(E) a fluorinated organohydrogensiloxane containing in a molecule at least two hydrosilyl groups and at least one group of the following general formula (6): ##STR52## wherein Rf.sup.2 is a monovalent perfluoroalkyl or perfluoroalkyl ether group, R.sup.6 is a divalent hydrocarbon group, and R.sup.7 is a hydrogen atom or monovalent hydrocarbon group, and
(C) a catalytic amount of a platinum group compound, component (E) being present in an amount to give 0.5 to 5 mol of the hydrosilyl group per mol of the aliphatic unsaturated group in the composition.

### Claim 4 (depends on 1)

The compound of formula (1) of claim 1, wherein:
R.sup.1 and R.sup.2 are independently a monovalent hydrocarbon group of 1 to 10 carbon atoms optionally substituted with halogen atoms,
R.sup.3 is a divalent hydrocarbon group of 1 to 20 carbon atoms optionally substituted by halogen atoms and optionally having at least one intervening --O-- group, --NR'-- group where R' is hydrogen or alkyl of 1-8 carbon atoms, organosilylene group or a group containing a linear or cyclic organosiloxane,
R.sup.4 and R.sup.5 are, independently, a divalent hydrocarbon group of 1 to 10 carbon atoms optionally substituted with halogen atoms, and
a is from 0 to 10.

### Claim 5 (depends on 2)

The composition of claim 2, wherein in the formula (1):
R.sup.1 and R.sup.2 are independently a monovalent hydrocarbon group of 1 to 10 carbon atoms optionally substituted with halogen atoms,
R.sup.3 is divalent hydrocarbon group of 1 to 20 carbon atoms optionally substituted by halogen atoms and optionally having at least one intervening --O-- group, --NR'-- group where R' is hydrogen or alkyl of 1-8 carbon atoms, organosilylene group or a group containing a linear or cyclic organosiloxane,
R.sup.4 and R.sup.5 are, independently, a divalent hydrocarbon group of 1 to 10 carbon atoms optionally substituted with halogen atoms, and
a is from 0 to 10.

### Claim 6 (depends on 1)

The compound of formula (1) of claim 1, wherein Rf.sup.1 is: a divalent perfluoroalkylene group of the formula
--C.sub.m F.sub.m --
where
m=1-10, or
a divalent perfluoropolyether group of one of the following formulae: ##STR53## wherein X is F or CF.sub.3 group, p, q and r are integers in the range: p.gtoreq.1, q.gtoreq.1, and 2.ltoreq.p+q.ltoreq.200, ##STR54## wherein r, s and t are integers in the range: 0.ltoreq.r.ltoreq.6, s.gtoreq.0, t.gtoreq.0, and 2.ltoreq.s+t.ltoreq.200, ##STR55## wherein X is F or CF.sub.3 group, u and v are integers in the range: 1.ltoreq.u.ltoreq.20 and 1.ltoreq.v.ltoreq.20, and
--CF.sub.2 CF.sub.2 --(OCF.sub.2 CF.sub.2 CF.sub.2).sub.w --OCF.sub.2 CF.sub.2 --
wherein w is an integer in the range: 1.ltoreq.w.ltoreq.20.

### Claim 7 (depends on 2)

The composition of claim 2, wherein in formula (1) Rf.sup.1 is:
a divalent perfluoroalkylene group of the formula
--C.sub.m F.sub.m --
where
m=1-10, or
a divalent perfluoropolyether group of one of the following formulae: ##STR56## wherein X is F or CF.sub.3 group, p, q and r are integers in the range: p.gtoreq.1, q.gtoreq.1, and 2.ltoreq.p+q.ltoreq.200, ##STR57## wherein r, s and t are integers in the range: 0.ltoreq.r.ltoreq.6, s.gtoreq.0, t.gtoreq.0, and 2.ltoreq.s+t.ltoreq.200, ##STR58## wherein X is F or CF.sub.3 group, u and v are integers in the range: 1.ltoreq.u.ltoreq.20 and 1.ltoreq.v.ltoreq.20, and
--CF.sub.2 CF.sub.2 --(OCF.sub.2 CF.sub.2 CF.sub.2).sub.w --OCF.sub.2 CF.sub.2 --
wherein w is an integer in the range: 1.ltoreq.w.ltoreq.20.

### Claim 8 (depends on 1)

A compound of claim 1 having a viscosity of about 100 to about 100,000 at 25.degree. C.

### Claim 9 (depends on 2)

A composition of claim 2 wherein the compound of formula (1) has a viscosity of about 100 to about 100,000 at 25.degree. C.

### Claim 10 (depends on 2)

An elastomer obtained by curing of the composition of claim 2.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R.sup.1 is an alkenyl group of 2-8 carbon atoms.

### Claim 12 (depends on 1)

The composition of claim 1, wherein in the fluorinated organohydrogensiloxane, (B), at least one perfluoroalkyl ether or pedluoroalkyl is of one of the following formulae:
C.sub.m F.sub.2m+1 --
wherein m is an integer of 1 to 10, and ##STR59## wherein n is an integer of 1 to 5.

### Claim 13 (depends on 2)

The composition of claim 2, wherein component (B) is provided in an a mount of 0.1 to 50 parts by weight per 100 parts by weight of component (A).

### Claim 14 (depends on 3)

The composition of claim 3, wherein:
R.sup.1 is a monovalent aliphatic unsaturated hydrocarbon group of 2 to 10 carbon atoms optionally substituted with halogen atoms,
R.sup.3 is a divalent hydrocarbon group of 1 to 20 carbon atoms optionally substituted by halogen atoms and optionally having at least one intervening --O-- group, --NR'-- group where R' is hydrogen or alkyl of 1-8 carbon atoms, organosilylene group or a group containing a linear or cyclic organosiloxane, and
a is from 0 to 10.

### Claim 15 (depends on 3)

The composition of claim 3, wherein Rf.sup.1 is:
a divalent perfluoroalkylene group of the formula
--C.sub.m F.sub.m --
where
m=1-10, or
a divalent perfluoropolyether group of one of the following formulae: ##STR60## wherein X is F or CF.sub.3 group, p, q and r are integers in the range: p.gtoreq.1, q.gtoreq.1, and 2.ltoreq.p+q.ltoreq.200, ##STR61## wherein r, s and t are integers in the range: 0.ltoreq.r.ltoreq.6, s.gtoreq.0, t.gtoreq.0, and 2.ltoreq.s+t.ltoreq.200, ##STR62## wherein X is F or CF.sub.3 group, u and v are integers in the range: 1.ltoreq.u.ltoreq.20 and 1.ltoreq.v.ltoreq.20, and
--CF.sub.2 CF.sub.2 --(OCF.sub.2 CF.sub.2 CF.sub.2).sub.w --OCF.sub.2 --CF.sub.2 --
wherein w is an integer in the range: 1.ltoreq.w.ltoreq.20.

### Claim 16 (depends on 3)

The composition of claim 3, wherein in formula (6) Rf.sup.2 is a perfluoroalkyl ether or perfluoroalkyl of one of the following formulae:
C.sub.m F.sub.2m+1 --
wherein m is an integer of 1 to 10, ##STR63## wherein n is an integer of 1 to 5; R.sup.6 is a divalent hydrocarbon group of 1-8 carbon atoms and
R.sup.7 is hydrogen or a monovalent hydrocarbon group of 1-8 carbon atoms optionally substituted by halogen atoms.

### Claim 17 (depends on 3)

The composition of claim 3, wherein the fluorinated organohydrogensiloxane, (E), has a monovalent hydrocarbon substituent of 1-10 carbon atoms free of an aliphatic unsaturated bond attached to a silicon atom.

### Claim 18 (depends on 3)

An elastomer obtained by curing the composition of claim 3.