# US 5,349,111 A · Benzocyclobutene novolac resin compositions

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- Number: US 5,349,111 A
- Document ID: US5349111A
- Status: Granted
- Kind: A
- Application number: 08/052,794
- Filed: 1993-04-23
- Granted: 1994-09-20
- Earliest claimed: 1993-04-23
- Assignees: The Dow Chemical Company
- Inventors: Daniel M. Scheck
- Web page: https://patentgrep.com/patent/US5349111A

## CPC

- C07C 43/295: containing hydroxy or O-metal groups
- C07C 2602/04: One of the condensed rings being a six-membered aromatic ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A novolac resin is prepared by reacting a phenolic compound, an aldehyde or a ketone, and a hydroxyl-substituted benzocyclobutene compound wherein the hydroxyl group is attached to an aromatic ring. The benzocyclobutenes are connected to the phenolic rings through an oxygen or oxyaryl bridge, or the cyclobutene is fused directly to a phenol ring. The novolac resin cures without evolution of volatiles and, when cured, provides a polymer which has a high glass transition temperature and which is essentially insoluble in organic solvents.

## Claims

### Claim 1

A compound represented by the formula ##STR4## wherein: R is independently at each occurrence hydrogen, aliphatic hydrocarbyl, aryl, aralkyl, or cycloaliphatic hydrocarbyl;
R' is independently at each occurrence hydrogen, aliphatic hydrocarbyl, aryl, aralkyl, or cycloaliphatic hydrocarbyl;
m is 0, 1, 2 or 3;
p is 0, 1, or 2;
x is 0.02 to 1.0;
n is 2 to 100;
X is a divalent organic or inorganic moiety;
Z is alkyl, aryl or halogeno; and
Ar is independently at each occurrence a C.sub.6 -C.sub.10 aromatic moiety.

### Claim 2 (depends on 1)

The compound of claim 1, wherein:
R is independently at each occurrence hydrogen, aliphatic hydrocarbyl, aryl, aralkyl, or cycloaliphatic hydrocarbyl;
R' is hydrogen;
m is 0, 1, or 2;
p is 0 or 1;
x is 0.05 to 0.70;
n is 2 to 30;
X is oxygen, sulfur, or an aliphatic
hydrocarbyl group;
Z is alkyl, aryl, or halogeno; and
Ar is a C.sub.6 -C.sub.10 aromatic moiety.

### Claim 3 (depends on 1)

The compound of claim 1, wherein:
R and R' are hydrogen;
m is 0, 1, or 2;
p is 0;
x is 0.10 to 0.40;
n is 3 to 15;
Z is an aliphatic hydrocarbyl moiety of 1 to 10 carbon atoms, halogeno, or phenyl; and
Ar is a benzene ring.

### Claim 4 (depends on 3)

The compound of claim 3 wherein m is 0.

### Claim 5 (depends on 3)

The compound of claim 3 wherein Z is a methyl group and m is 1.

### Claim 6 (depends on 3)

The compound of claim 3 wherein Z is chloro and m is 1.

### Claim 7 (depends on 1)

The compound of claim 1 wherein Ar is independently at each occurrence a C.sub.6 -C.sub.10 aromatic moiety substituted with a C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, alkaryl, alkanol, aroyl, alkoxy, or aryloxy.

### Claim 8 (depends on 3)

The compound of claim 3 wherein X is an aliphatic hydrocarbyl group substituted with fluorine atoms.

### Claim 9 (depends on 3)

The compound of claim 3 wherein Ar is a C.sub.6 -C.sub.10 aromatic moiety substituted with a C.sub.1 -C.sub.10 alkyl group.

### Claim 10

A compound represented by the formula: ##STR5## wherein: R is independently at each occurrence hydrogen, aliphatic hydrocarbyl, aryl, aralkyl, or cycloaliphatic hydrocarbyl;
R' is independently at each occurrence hydrogen, aliphatic hydrocarbyl, aryl, aralkyl, or cycloaliphatic hydrocarbyl;
m is 0, 1, 2 or 3;
x is 0.02 to 1.0;
n is 2 to 100; and
Z is alkyl, aryl, or halogeno.

### Claim 11 (depends on 10)

The compound of claim 10 wherein R and R' are hydrogen.

### Claim 12 (depends on 2)

A process for preparing the compound of claim 2 which comprises reacting a phenolic compound, an aldehyde or a ketone, and a hydroxyl-substituted benzocyclobutene compound, in the presence of an acid catalyst selected from the group consisting of oxalic acid, sulfuric acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.