# US 5,710,235 A · Olefinic and urethane-terminated ester polyalkadiene

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- Number: US 5,710,235 A
- Document ID: US5710235A
- Status: Granted
- Kind: A
- Application number: 08/570,055
- Filed: 1995-12-11
- Granted: 1998-01-20
- Earliest claimed: 1995-12-11
- Assignees: Lord Corporation
- Inventors: Kirk Joseph Abbey; Ian Christopher Quarmby
- Web page: https://patentgrep.com/patent/US5710235A

## CPC

- C08F 290/048: {Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00}
- C08C 19/38: with hydroxy radicals
- C09J 151/06: grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

An olefinic-terminated polyalkadiene that includes carboxy ester linking groups and at least one nascent secondary hydroxyl group that is capped with a monoisocyanate. This polyalkadiene can be made by reacting a hydroxyl-terminated polyalkadiene with a saturated cyclic acid anhydride to form a carboxylic acid-terminated polyalkadiene, reacting the carboxylic acid-terminated polyalkadiene with an olefinic monoepoxide to form an olefinic-terminated polyalkadiene, then reacting the olefinic-terminated polyalkadiene with a monoisocyanate.

## Claims

### Claim 1

A polymer having a representative structure comprising ##STR8## wherein X is a polyalkadiene residue,
a averages from 1.2 to 2.6 per polymer molecule, provided a is.ltoreq.b,
b is at least 1.2 per polymer molecule,
R.sup.1 is a divalent radical that includes at least two carbon atoms and is selected from the group consisting of saturated alkylene, substituted saturated alkylene, arylene, and saturated heterocyclic,
R.sup.6 is phenyl, napthyl, an alkyl group having from 1 to 24 carbon atoms, substituted phenyl, substituted napthyl, phenylalkyl or napthylalkyl,
R.sup.7 has the structure ##STR9## wherein R.sup.4 is a divalent radical selected from the group consisting of alkylene, alkylene ester, arylene and alkylene ether, and
R.sup.3 is hydrogen, an alkyl group of 1 to 4 carbon atoms, --CH.dbd.CH.sub.2, or --R.sup.5 --CH.dbd.CH.sub.2 wherein R.sup.5 is an alkylene radical having 1 to 4 carbon atoms.

### Claim 2 (depends on 1)

A polymer according to claim 1 wherein X comprises a polyalkadiene residue that is derived from at least one of polybutadiene, poly(butadiene-acrylonitrile), poly(butadiene-methacrylonitrile-acrylic acid), partially-hydrogenated polybutadiene or fully-hydrogenated polybutadiene.

### Claim 3 (depends on 1)

A polymer according to claim 1 wherein X includes at least a 1,4-polybutadiene repeating unit.

### Claim 4 (depends on 1)

A polymer according to claim 1 wherein R.sup.1 is a divalent saturated alkylene having 2 to 4 carbon atoms.

### Claim 5 (depends on 1)

A polymer according to claim 1 wherein R.sup.1 is a divalent substituted saturated alkylene having 2 to 4 carbon atoms in the alkylene portion and including at least one alkyl, alkenyl, aryl or alkylaryl substituent bonded to at least one of the carbon atoms of the alkylene portion.

### Claim 6 (depends on 1)

A polymer according to claim 1 wherein R.sup.1 is a divalent unsubstituted or substituted arylene wherein the divalent bond sites are located on the aromatic ring.

### Claim 7 (depends on 1)

A polymer according to claim 1 herein R.sup.4 is --CH.sub.2 --O--C(O)--.

### Claim 8 (depends on 1)

A polymer according to claim 1 wherein R.sup.3 is an alkyl group having 1 to 4 carbon atoms.

### Claim 9 (depends on 1)

A polymer according to claim 1 wherein R.sup.6 is phenyl or phenylalkyl.

### Claim 10 (depends on 1)

A polymer according to claim 1 wherein R.sup.6 is phenyl or substituted phenyl, R.sup.3 is an alkyl group having 1 to 4 carbon atoms, R.sup.1 is selected from the group consisting of a divalent saturated alkylene having 2 to 4 carbon atoms, a divalent substituted saturated alkylene having 2 to 4 carbon atoms in the alkylene portion and including at least one alkyl, alkenyl, aryl or alkylaryl substituent bonded to at least one of the carbon atoms of the alkylene portion, and a divalent unsubstituted or substituted arylene wherein the divalent bond sites are located on the aromatic ring, and X comprises a polyalkadiene residue that is derived from at least one of polybutadiene, poly(butadiene-acrylonitrile), or poly(butadiene-methacrylonitrile-acrylic acid).

### Claim 11 (depends on 1)

A polymer according to claim 1 wherein the polymer is a liquid.