# US 4,377,707 A · Halogenated (meth) acrylate compounds

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- Number: US 4,377,707 A
- Document ID: US4377707A
- Status: Granted
- Kind: A
- Application number: 06/331,748
- Filed: 1981-12-17
- Granted: 1983-03-22
- Earliest claimed: 1981-12-17
- Assignees: The Dow Chemical Company
- Inventors: Clinton J. Boriack; Hans R. Friedli
- Web page: https://patentgrep.com/patent/US4377707A

## CPC

- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07C 69/653: Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Halogenated dicyclopentyl ethers or thioethers of alkylene glycol mono(meth) acrylate or mono (meth) propionates are prepared. The dihalo compounds having (meth) acrylic functionality are useful to prepare thermosetting or thermoplastic resins with built in fire retardency. The tetrahalo compounds are useful fire retardant additives in the manufacture of polymeric foams.

## Claims

### Claim 1

A compound having the formula
CH.sub.2 .dbd.C(R)--C--(O)--Z--M--[Z--M.sup.1 --].sub.n --Z--Q
where
Q is the 2,3-dihalodicyclopentyl group ##STR4## X is chlorine or bromine, R is hydrogen or methyl,
M is an alkylene group having 2-10 carbon atoms,
M.sup.1 is an alkylene group having 2-10 carbon atoms and can be the same as or different from M,
Z is oxygen or sulfur,
n is zero to three.

### Claim 2

A compound having a formula
CH.sub.2 (X)--C(R)(X)--C(O)--Z--M--[Z--M.sup.1 --].sub.n --Z--Q
where
Q is the 2,3-dihalodicyclopentyl group ##STR5## X is chlorine or bromine, R is hydrogen or methyl,
M is an alkylene group having 2-10 carbon atoms,
M.sup.1 is an alkylene group having 2-10 carbon atoms and can be the same as or different from M,
Z is oxygen or sulfur,
n is zero or three.

### Claim 3

A compound having the formula
CH.sub.2 .dbd.C(R)--C(O)--O--M--O--Q
where
Q is the 2,3-dihalodicyclopentyl group ##STR6## X is chlorine or bromine, R is hydrogen or methyl,
M is an alkylene group having 2-10 carbon atoms.

### Claim 4 (depends on 3)

A compound as defined in claim 3 wherein X is bromine, R is hydrogen and M is an ethylene group.

### Claim 5 (depends on 3)

A compound as defined in claim 3 wherein X is chlorine, R is hydrogen and M is an ethylene group.

### Claim 6 (depends on 3)

A compound as defined in claim 3 wherein X is bromine, R is methyl, and M is an ethylene group.

### Claim 7 (depends on 3)

A compound as defined in claim 3 wherein X is chlorine, R is methyl and M is an ethylene group.

### Claim 8

A compound having the formula
CH.sub.2 (X)--C(R)(X)--C(O)--O--M--O--Q
where
Q is the 2,3-dihalodicyclopentyl group ##STR7## X is chlorine or bromine, R is hydrogen or methyl,
M is an alkylene group having 2-10 carbon atoms.

### Claim 9 (depends on 8)

A compound as defined in claim 8 wherein X is bromine, R is hydrogen, and M is an ethylene group.

### Claim 10 (depends on 8)

A compound as defined in claim 8 wherein X is chlorine, R is hydrogen, and M is an ethylene group.

### Claim 11 (depends on 8)

A compound as defined in claim 8 wherein X is bromine, R is methyl, and M is an ethylene group.

### Claim 12 (depends on 8)

A compound as defined in claim 8 wherein X is chlorine, R is methyl, and M is an ethylene group.