# US 5,705,603 A · Polyetheramines with polymers of .alpha., .beta.-unsaturated dicarboxylic acids

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- Number: US 5,705,603 A
- Document ID: US5705603A
- Status: Granted
- Kind: A
- Application number: 08/493,623
- Filed: 1995-06-22
- Granted: 1998-01-06
- Earliest claimed: 1994-06-24
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Matthias Krull; Michael Feustel; Erdmann Mielcke
- Web page: https://patentgrep.com/patent/US5705603A

## CPC

- C10L 1/1966: {poly-carboxylic}
- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- C10L 1/143: {mixtures of organic macromolecular compounds with organic non-macromolecular compounds}
- C10L 1/2364: {homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups (C10L1/221 takes precedence)}
- C10L 1/238: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)}
- C10L 1/1973: {mono-carboxylic}
- C10L 1/2222: {(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates (C10L1/221 takes precedence)}
- C10L 1/2225: {hydroxy containing (C10L1/221 takes precedence)}
- C10L 1/2437: {Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters}
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

The invention relates to reaction products of polyetheramines with polymers containing dicarboxylic anhydride groups, which contain 20-80, preferably 40-60, mol % of bivalent structural units A and/or C and, if required, B ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen or methyl, a and b are equal to zero or one and a+b is equal to one, Y is X or NRR.sup.3, X is --OH, --O--C.sub.1-30 -alkyl, NR.sup.3 R.sup.4 or --O.sup..crclbar. N.sup..sym. R.sup.3 R.sup.4, R.sup.3 and R.sup.4, independently of one another, are hydrogen, C.sub.6 -C.sub.40 -alkyl or R, R is ##STR2## with the proviso that at least 1 mol % of the anhydride groups bonded to the polymer have reacted with a polyetheramine, Z is C.sub.2 -C.sub.4 -alkyl, n is a number from 1 to 1000, R.sup.5 is hydrogen, C.sub.1 -C.sub.30 -alkyl, C.sub.5 -C.sub.12 -cycloalkyl or C.sub.6 -C.sub.30 -aryl and R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl, preferably methyl, and 80-20 mol %, preferably 60-40 mol % of bivalent structural units D ##STR3## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.8 is C.sub.1 -C.sub.60 -alkyl or C.sub.6 -C.sub.18 -aryl.

## Claims

### Claim 1

A reaction product of a polyetheramine with a polymer comprising dicarboxylic acid anhydride groups, which contains 20-80 mol % of bivalent structural units A or C or a mixture of A and C and, optionally, structural units B ##STR10## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen or methyl,
a and b are equal to zero or one and a+b is equal to one,
Y is X or NRR.sup.3
X is --OH, --O--(C.sub.1 -C.sub.30 -alkyl), NR.sup.3 R.sup.4 or --O.sup..crclbar. N.sup..sym. R.sup.3 R.sup.4,
R.sup.3 and R.sup.4, independently of one another, are hydrogen, C.sub.6 -C.sub.40 -alkyl or R,
R is ##STR11## with the proviso that at at least 1 mol % of the anhydride groups bonded to the polymer have react with a polyetheramine of the formula (H) ##STR12## in which R.sup.3 is hydrogen, C.sub.6 -C.sub.40 -alkyl or R,
R is a group of the formula
--Z--(O--CH--CH.sub.2).sub.n O--R.sup.5
R.sup.6
Z is C.sub.2 -C.sub.4 -alkyl,
n is a number from 1 to 1000,
R.sup.5 is C.sub.1 -C.sub.30 -alkyl, C.sub.5 -C.sub.12 -cycloalkyl or C.sub.8 -C.sub.30 -aryl and
R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl,
Z is C.sub.2 -C.sub.4 -alkyl,
n is a number from 1 to 1000,
R.sup.5 is C.sub.1 -C.sub.30 -alkyl, C.sub.5 -C.sub.12 -cycloalkyl or C.sub.6 -C.sub.30 -aryl and
R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and
8- 20mol % of bivalent structural units D ##STR13## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl and
R.sup.8 is C.sub.1 -C.sub.60 -alkyl or C.sub.6 -C.sub.18 -aryl.

### Claim 2 (depends on 1)

A process for the preparation of the reaction products as claimed in claim 1, which comprises polymerizing monomers of the formulae E or F or a mixture of formulae E or F with the monomers of the formula G, ##STR14## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen or methyl, ##STR15## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.8 is C.sub.1 -C.sub.60 -alkyl or C.sub.6 -C.sub.18 -aryl, and then reacting the product formed with polyetheramines of the formula H or a mixture of formula H with an alkanolamine of the formula I, ##STR16## in which R.sup.3 is hydrogen, C.sub.6 -C.sub.40 -alkyl or R, R is a group of the formula ##STR17## Z is C.sub.2 -C.sub.4 -alkyl, n is a number from 1 to 1000,
R.sup.5 is C.sub.1 -C.sub.30 -alkyl, C.sub.5 -C.sub.12 -cycloalkyl or C.sub.8 -C.sub.30 -aryl and
R.sup.6 is hydrogen or C.sub.1 -C.sub.4 -alkyl, ##STR18## in which R.sup.9 and R.sup.10, independently of one another, are hydrogen, C.sub.2 -C.sub.22 -alkenyl, C.sub.1 -C.sub.22 -alkyl or Z--OH, with the proviso that at least one radical R.sup.9 or R.sup.10 is Z--OH and with the proviso that at least 1 mol % of the anhydride groups bonded to the polymer are reacted with a polyetheramine.

### Claim 3 (depends on 2)

The process as claimed in claim 2, wherein the reaction of the polymer with the polyetheramines of the formula (H) or with the alkanolamines of the formula (I) or a mixture of formulae (H) and (I) is carried out at temperatures of from 50.degree. to 250.degree. C.

### Claim 4 (depends on 1, 2)

The process as claimed in claim 2, wherein the polymerization is carried out in a solvent in which the monomers of the formulae E, F, G, H or I or a mixture thereof, and the reaction products as claimed in claim 1 are soluble.

### Claim 5 (depends on 1)

The reaction product as claimed in claim 1, wherein said dicarboxylic anhydride groups contain 40 to 60 mol % of bivalent structural units A or C or a mixture of A and C, and optionally, structural units B and 60 to 40 mol % of bivalent structural units D.

### Claim 6 (depends on 5)

The reaction product as claimed in claim 5, wherein R.sup.6 is methyl.