# US 4,393,192 A · Crystalline copolymers prepared from N,N'-terephthaloyldi-beta-alanine and a glycol

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 4,393,192 A
- Document ID: US4393192A
- Status: Granted
- Kind: A
- Application number: 06/451,998
- Filed: 1982-12-21
- Granted: 1983-07-12
- Earliest claimed: 1982-12-21
- Assignees: The Standard Oil Company
- Inventors: Benedict S. Curatolo; Gerald P. Coffey
- Web page: https://patentgrep.com/patent/US4393192A

## CPC

- C08G 69/44: Polyester-amides
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Novel water insoluble polyamide esters are prepared from dicarboxylic acid diamide derivatives of terephthalic acid and a glycol. In one embodiment, nearly perfectly alternating polyamide esters are prepared in the presence of antimony (III) acetate.

## Claims

### Claim 1

Novel water insoluble polyamide esters of the general formula: ##STR6## where each R and R' independently are a divalent aliphatic, alicyclic or aromatic radical;
x is a number of 0 to 100 and represents the percentage of the polyamide ester chain structure containing the following unit: ##STR7##

### Claim 2 (depends on 1)

The polyamide ester of claim 1 where each R is a C.sub.2 -C.sub.12 alkylene radical.

### Claim 3 (depends on 1)

The polyamide ester of claim 1 where R' is C.sub.2 -C.sub.8 aliphatic radical, a C.sub.6 -C.sub.17 alicyclic radical or a phenyl radical.

### Claim 4 (depends on 2)

The polyamide ester of claim 2 where R' is a C.sub.2 -C.sub.8 alkylene radical or a C.sub.6 -C.sub.17 one or two ring cycloparrafin radical.

### Claim 5 (depends on 1)

The polyamide ester of claim 1 each R and R' are --(CH.sub.2 CH.sub.2)--.

### Claim 6 (depends on 1)

The polyamide ester of claim 1 where x is greater than 75 and less than 100.

### Claim 7 (depends on 1)

The polyamide ester of claim 1 where x is approximately 100.

### Claim 8 (depends on 7)

A process for preparing the water insoluble polyamide ester of claim 7 from a dicarboxylic acid diamide and a glycol comprising:
(a) mixing in solvent stoichiometric amounts of the dicarboxylic acid diamide and the glycol in the presence of a catalyzing amount of a catalyst consisting of at least one of antimony (III) acetate, zinc acetate, calcium acetate and antimony trioxide;
(b) heating with agitation the mixture at between 150.degree. and 300.degree. C. for a time sufficient for polymerization to occur; and
(c) removing substantially all the water produced by the reaction of the monomers.

### Claim 9 (depends on 8)

The process of claim 8 where amount of catalyst is approximately between 0.5 and 5.0 wt percent of the total weight of the dicarboxylic acid diamide and glycol.

### Claim 10 (depends on 9)

The process of claim 9 where the amount of catalyst is approximately 2 wt percent of the total weight of the dicarboxylic acid diamide and glycol.

### Claim 11 (depends on 8)

The process of claim 8 where the catalyst is antimony (III) acetate.

### Claim 12 (depends on 8)

The process of claim 8 where the mixture is heated between 190.degree. C. and 210.degree. C. for approximately 24 hours.

### Claim 13 (depends on 8)

The process of claim 8 where the solvent is one of N-methyl pyrrolidone, dimethyl acetamide, dimethyl formamide and hexamethyl phosphoramide.

### Claim 14 (depends on 13)

The process of claim 13 where the solvent is N-methyl pyrrolidone.

### Claim 15 (depends on 8)

The process of claim 8 where the means for removing the water by-product comprises the continuous passing of an inert gas through the reactants in solution.

### Claim 16 (depends on 6)

A process for preparing water insoluble polyamide esters of claim 6 from a dicarboxylic acid diamide and a glycol comprising:
(a) mixing the diacid diamide with an excess stoichiometric amount of the glycol; and
(b) heating with agitation the mixture at approximately between 150.degree. and 300.degree. C. for a time sufficient for polymerization to occur.

### Claim 17 (depends on 16)

The process of claim 16 where the excess stoichiometric amount of the ethylene glycol is between 2 and 20 times greater than a stoichiometric amount.

### Claim 18 (depends on 16)

The process of claim 16 where the mixture is heated at between 190.degree. C. and 210.degree. C. for approximately 20 hours.