# US 6,723,827 B2 · Chemically resistant polythioethers and formation thereof

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- Number: US 6,723,827 B2
- Document ID: US6723827B2
- Status: Granted
- Kind: B2
- Application number: 10/368,135
- Filed: 2003-02-20
- Published: 2003-07-10
- Granted: 2004-04-20
- Earliest claimed: 2000-03-09
- Assignees: PBT Brands, Inc.
- Inventors: Jonathan D. Zook; David W. Jordan; Dean M. Willard; George Jones; Michael Cosman
- Web page: https://patentgrep.com/patent/US6723827B2

## CPC

- C08G 75/04: from mercapto compounds or metallic derivatives thereof (C08G75/0204 takes precedence)
- C08G 75/12: Polythioether-ethers (C08G75/0245 takes precedence)
- C08L 81/02: Polythioethers; Polythioether-ethers
- 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

A polythioether comprising: wherein R1 is a C1-10 alkyl, —(R3Q)pR3— or C6-C20 aryl where Q is O or S, each R3 is independently C1-6 alkyl, and p is an integer between 0 and 6; R2 is C1-6 alkyloxy or C5-12 cycloalkyloxy, R4 is H, C1-6 alkyl, C1-6 alkyl alcohol and C0-6 alkyl substituted with where X is a halogen, m is an integer between 1 and 4, and n is an integer selected to yield a molecular weight for said polythioether of between 1000 and 10,000 Daltons.

## Claims

### Claim 1

A process for forming a polythioether comprising:
wherein R1 is a C1-10 alkyl, —(R3Q)pR3— or C6-C20 aryl where Q is O or S, each R3 is independently C1-6 alkyl, and p is an integer between 0 and 6; R2 is C1-6 alkyloxy or C5-12 cycloalkyloxy, R4 is H, C1-6 alkyl, C1-6 alkyl alcohol and C0-6 alkyl substituted with
where X is a halogen, m is an integer between 1 and 4, and n is an integer selected to yield a molecular weight for said polythioether of between 1000 and 10,000 Daltons comprising the step of: reacting a polythiol and a polyhalide in the presence of an aqueous base.

### Claim 2 (depends on 1)

The process of claim 1 wherein said polythiol is a dithiol.

### Claim 3 (depends on 2)

The process of claim 2 wherein the dithiol is selected from the group consisting of: ethanedithiol, vinylcyclohexyldithiol, dicyclopentadienedithiol, dipentene dimercaptan, hexanedithiol, dimercaptodiethyl sulfide, dimercaptodiethyl ether, and dimercaptodioxaoctane.

### Claim 4 (depends on 1)

The process of claim 1 wherein said polyhalide is a dihalide.

### Claim 5 (depends on 4)

The process of claim 4 wherein said dihalide is selected from the group consisting of: dichloroalkane and a polyglycol dihalide.

### Claim 6 (depends on 1)

The process of claim 1 wherein said polyhalide is a polychloride.

### Claim 7 (depends on 1)

The process of claim 1 wherein said polyhalide is a trihalide.

### Claim 8 (depends on 1)

The process of claim 1 wherein n+1 equivalents of thiol of said polythiol are reacted with n equivalents of halide of said polyhalide.

### Claim 9 (depends on 0, 1)

A curable composition comprising:
42 to 80 weight percent of a polythioether polymer according to claim 1,
0.3 to 15 weight percent of a lightweight filler and 0.1 to 20 weight percent of a curing agent.

### Claim 10 (depends on 9)

The curable composition of claim 9 further comprising one or more additives selected from the group consisting of: pigments, cure accelerators, surfactants, adhesion promoters, thixotropic agents and solvents.

### Claim 11 (depends on 10)

The curable composition of claim 10 wherein said lightweight filler comprises microspheres.

### Claim 12 (depends on 10)

The curable composition of claim 10 wherein said lightweight filler comprises an amorphous material.