Polyester

Patent metadata

Field	Value
Publication number	US-11597799-B2
Application number	US-201816609233-A
Country	US
Kind code	B2
Filing date	May 2, 2018
Priority date	May 10, 2017
Publication date	Mar 7, 2023
Grant date	Mar 7, 2023

Abstract

The present invention relates to a polyester consisting of (A) repeat units derived from an acid component, which consists of (a1) 2,5-furandicarboxylic acid, (a2) an aliphatic C 4 -C 36 dicarboxylic acid or a mixture of a plurality of aliphatic C 4 -C 36 dicarboxylic acids, and (a3) a sulfonate group-containing dicarboxylic acid, and of (B) repeat units derived from a di-ol/amine component, and optionally of further repeat units (C) and/or branching components (E), and of (D) repeat units derived from at least one di- or oligofunctional compound selected from the group consisting of a di- or oligoisocyanate and a di- or oligoisocyanurate. In addition, the present invention relates to the production of these polyesters and their use.

First claim

The invention claimed is:

1. A polyester consisting of:
A) repeat units derived from an acid component, which consists of
a1) 30 to 90 mol %, based on the sum of components a1, a2, and a3, of 2,5-furandicarboxylic acid,
a2) 0 to 60 mol %, based on the sum of components a1, a2, and a3, of an aliphatic C 4 -C 36 dicarboxylic acid or a mixture of a plurality of aliphatic C 4 -C 36 dicarboxylic acids, and
a3) 10 to 60 mol %, based on the sum of components a1, a2, and a3, of a sulfonate group-containing dicarboxylic acid,
wherein a3 is an aromatic sulfonate group-containing dicarboxylic acid in which the sulfonate group is present either as the free acid or as a salt, and a3 is selected from the group consisting of 1,4-benzenedicarboxylic acid-2-sulfonic acid, 1,3-benzenedicarboxylic acid-5-sulfonic acid, 1,2-benzenedicarboxylic acid-3-sulfonic acid, and 1,2-benzenedicarboxylic acid-4-sulfonic acid, in each case in the form of the free acid or of a salt, and
wherein the molar percentages of components a1) to a3) together add up to 100 mol %,

B) repeat units derived from a di-ol/amine component consisting of
b1) a C 2 to C 12 alkanediol or a mixture of a plurality of C 2 to C 12 alkanediols, and/or
b2) a dihydroxy compound of formula I,
HO—[(CH 2 ) n —O] m —H  (I)

where n is 2, 3 or 4 and m is an integer from 2 to 250,
or a mixture of a plurality of such dihydroxy compounds,
b3) optionally one or more amino C 2 to C 12 alkanols or one or more amino C 5 to C 10 cycloalkanols or mixtures thereof, and
b4) optionally one or more diamino C 1 to C 8 alkanes,
wherein the amount of B is chosen so that for every 100 mol of A there is 100 mol of B present, minus the number of moles of D and E,
and wherein a sum of b1 and b2 in B is at least 50 mol %,

C) optionally repeat units derived from
c1) one or more hydroxycarboxylic acids of formula IIa,
HO—C(O)-G-OH  (IIa)

where G represents a radical selected from the group consisting of phenylene, —(CH 2 ) q —, in which q is an integer from 1 to 5, —C(R)H—, and —C(R)HCH 2 , in which R is methyl or ethyl, and/or
c2) one or more aminocarboxylic acids or cyclic amides thereof selected from the group consisting of caprolactam, 1,6-aminocaproic acid, laurolactam, 1,12-aminolauric acid, and 1,11-aminoundecanoic acid,
wherein the proportion of C in the total mass of the polyester is not more than 20% by weight,

D) 0.1 to 4% by weight, based on the sum of components A, B, and C, of repeat units derived from at least one di- or oligofunctional compound selected from the group consisting of a di- or oligoisocyanate and a di- or oligoisocyanurate, and
E) 0.1 to 4% by weight, based on the sum of components A, B, and C, of repeat units derived from a branching component that contains at least three functional groups, wherein the functional groups are selected from the group consisting of COOH, OH, NH 2 , and mixtures thereof.

2. The polyester as claimed in claim 1 , wherein a sum of a2, b3, b4, c1, and c2, based on the total mass of the polyester, is not more than 10% by weight.

3. The polyester as claimed in claim 1 , wherein b1 is selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, 1,5-pentanediol, 2,4-dimethyl-2-ethylhexane-1,3-diol, 2,2-dimethyl-1,3-propanediol, 2-ethyl-2-butyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,6-hexanediol, 1,8-octanediol, and 2,2,4-trimethyl-1,6-hexanediol.

4. The polyester as claimed in claim 1 , wherein b2 is selected from the group consisting of diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, and polytetrahydrofuran.

5. The polyester as claimed in claim 1 , wherein D is repeat units derived from an aliphatic diisocyanate, wherein the diisocyanate is a straight-chain or branched alkylene diisocyanate or cycloalkylene diisocyanate having in both cases 2 to 20 carbon atoms.

6. The polyester as claimed in claim 1 , wherein E is repeat units derived from a branching component selected from the group consisting of tartaric acid, citric acid, malic acid, trimethylolpropane, trimethylolethane, pentaerythritol, a polyether triol, glycerol, trimesic acid, trimellitic acid, and pyromellitic acid.

7. An aqueous solution comprising the polyester as claimed in claim 1 and water.

8. A personal care formulation comprising the polyester as claimed in claim 1 and water.

9. A laminating adhesive comprising the polyester as claimed in claim 1 and water.

10. A method of setting hair comprising contacting the hair with a personal care formulation comprising the polyester as claimed in claim 1 and water.

11. A process for production of the polyester as claimed in claim 1 comprising
the reaction of a mixture comprising the acid component as defined under A, the di-ol/amine component as defined under B, optionally the hydroxycarboxylic acids as defined under c1, optionally the aminocarboxylic acids and/or cyclic amides thereof as defined under c2, and the branching component as defined under E, wherein an intermediate is obtained,
the removal from the intermediate of any excess of the di-ol/amine component as defined under B, and
the reaction of the intermediate with the compound as defined under D,
wherein a1, a2, and a3 are independently each used as the free dicarboxylic acid or as the dialkyl ester,
and wherein b1, b2, b3, and b4 are used underivatized as defined under b1, b2, b3, and b4,
and wherein c1 is used as the free hydroxycarboxylic acid or in the form shown in formulas IIa or IIb,

in which p is an integer from 1 to 1500 and r is an integer from 1 to 4, and G represents a radical selected from the group consisting of phenylene, —(CH 2 ) q —, in which q is an integer from 1 to 5, —C(R)H—, and —C(R)HCH 2 , in which R is methyl or ethyl,
and wherein c2 is used as the free aminocarboxylic acids or in the form of the cyclic amide thereof,
and wherein D is used underivatized as the di- or oligoisocyanate or di- or oligoisocyanurate,
and wherein E is used underivatized.

12. The polyester of claim 1 wherein the proportion of a1 is 55 to 85 mol % and the proportion of a2 is at the same time 0 to 30 mol % and the proportion of a3 is at the same time 15 to 45 mol %.

13. The polyester of claim 1 wherein the sum of b1 and b2 is at least 50 mol %.

14. The polyester of claim 1 wherein the proportion of C in the total mass of the polyester is not more than 10% by weight.

15. The polyester of claim 2 wherein the sum of a2, b3, b4, c1, and c2, based on the total mass of the polyester, is not more than 5% by weight.

16. The polyester of claim 3 wherein b1 is selected from the group consisting of ethylene glycol, 1,4-butanediol, 1,6-hexanediol, and 1,8-octanediol.

17. The polyester of claim 4 wherein b2 is selected from the group consisting of diethylene glycol, triethylene glycol, and tetraethylene glycol.

18. The polyester of claim 5 wherein the repeat units of D have 3 to 15 carbon atoms.

19. The polyester of claim 6 wherein E are repeat units derived from the group consisting of tartaric acid, citric acid, malic acid, trimethylolpropane, pentaerythritol, and glycerol.

Assignees

• Basf Se

Inventors

• Schick Michael Bernhard
• Yamamoto Motonori

Classifications

• C08G63/78

  Preparation processes · CPC title

• C08G18/4615

  containing nitrogen · CPC title

• C09J167/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09J167/06 takes precedence) · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/4676

  containing sulfur · CPC title