# US 5,708,105 A · Di-(alken-1-yl)-substituted borinic acids and borinates as oxidation inhibitors for carbon composites

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- Number: US 5,708,105 A
- Document ID: US5708105A
- Status: Granted
- Kind: A
- Application number: 07/360,567
- Filed: 1989-06-02
- Granted: 1998-01-13
- Earliest claimed: 1989-06-02
- Assignees: Aerojet-General Corporation
- Inventors: Stephen John Backlund; Robert Earl Olsen
- Web page: https://patentgrep.com/patent/US5708105A

## CPC

- C08F 30/06: containing boron
- C08K 5/55: Boron-containing compounds {(C08K5/0091 takes precedence)}
- C08F 230/065: {the monomer being a polymerisable borane, e.g. dimethyl(vinyl)borane}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

Resins and carbon-carbon composites are formed from di(alken-1-yl) borinic acids and borinates, either as monomers or as nonpolymerizing additives in a monomer mixture, with the effect of sharply increasing the oxidative stability of the cured product. The compounds have the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, aryl, (C.sub.1 -C.sub.6 alkyl)-substituted aryl, (C.sub.2 -C.sub.6 alkenyl)-substituted aryl, or (C.sub.2 -C.sub.6 alkynyl)-substituted aryl, at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being other than H.

## Claims

### Claim 1

A carbon-carbon composite comprising a combination of a carbon filler and a cured resin formed by polymerization of a monomer composition containing an organic boron-containing compound that is not oxidized and does not form a separate glassy phase but is uniformly distributed throughout the cured resin and having the formula: ##STR14## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently selected from the group consisting of H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, aryl, (C.sub.2 -C.sub.6 alkyl)-substituted aryl, (C.sub.2 -C.sub.6 alkenyl)-substituted aryl, and (C.sub.2 -C.sub.6 alkynyl)-substituted aryl, with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is other than H.

### Claim 2 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which:
R.sup.1 and R.sup.2 are independently selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, aryl, (C.sub.1 -C.sub.6 alkyl)-substituted aryl, (C.sub.2 -C.sub.6 alkenyl)-substituted aryl, and (C.sub.2 -C.sub.6 alkynyl)-substituted aryl;
R.sup.3 and R.sup.4 are independently selected from the group consisting of H and C.sub.1 -C.sub.6 alkyl; and
R.sup.5 is selected from the group consisting of H and C.sub.2 -C.sub.6 alkynyl.

### Claim 3 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which R.sup.1 and R.sup.2 are independently selected from the group consisting of C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, cyclohexenyl, phenyl, (C.sub.2 -C.sub.6 alkenyl)-substituted phenyl, and (C.sub.2 -C.sub.6 alkynyl)-substituted phenyl; R.sup.3 and R.sup.4 are independently selected from the group consisting of H and CH.sub.3 ; and R.sup.5 is selected from the group consisting of H and CH.sub.2 C.tbd.CH.

### Claim 4 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which R.sup.1 and R.sup.2 are independently selected from the group consisting of vinyl-substituted phenyl and ethynyl-substituted phenyl, R.sup.3 and R.sup.4 are both H, and R.sup.5 is H.

### Claim 5 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which said monomer composition is comprised of at least one monomer selected from the group consisting of ##STR15## and R.sup.1 and R.sup.2 are independently selected from the group consisting of aryl, (C.sub.1 -C.sub.6 alkyl)-substituted aryl, and C.sub.5 -C.sub.7 cycloalkenyl.

### Claim 6 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which said monomer composition is comprised of at least one monomer selected from the group consisting of ##STR16## and R.sup.1 and R.sup.2 are independently selected from the group consisting of phenyl, (C.sub.1 -C.sub.6 alkyl)-substituted phenyl, and cyclohexenyl.

### Claim 7 (depends on 1)

A carbon-carbon composite in accordance with claim 1 in which said monomer composition is comprised of a combination of the following monomers ##STR17## and R.sup.1 and R.sup.2 are independently selected from the group consisting of phenyl and cyclohexenyl.