Acid functional compound

Patent metadata

Field	Value
Publication number	US-12570797-B2
Application number	US-201816635846-A
Country	US
Kind code	B2
Filing date	Aug 7, 2018
Priority date	Aug 8, 2017
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

The invention relates to an acid functional compound comprising i. at least one segment consisting of at least one ether unit E and at least one ester unit, wherein the ether units and ester units are connected by an ether link or by an ester link, and wherein the sum of the number of ether units and ester units is at least three, and wherein the ether units and ester units are arranged in random order, and ii. at least one acidic group which is selected from the group consisting of a phosphoric acid group, an acidic phosphoric acid ester group, a sulfonic acid group, an acidic sulfonic acid ester group and a carboxylic acid group, wherein the at least one acidic group is covalently linked to the at least one segment.

First claim

The invention claimed is:

1 . An acid functional compound comprising
i. at least one segment comprising at least one ether unit and at least one ester unit, wherein the at least one ether unit and the at least one ester unit are connected by an ether link or by an ester link, and wherein the sum of the number of the at least one ether unit and the at least one ester unit is at least three, and wherein the at least one ether unit and the at least one ester unit are arranged in random order, and ii. at least one acidic group selected from a phosphoric acid group, an acidic phosphoric acid ester group, a sulfonic acid group, an acidic sulfonic acid ester group and a carboxylic acid group, wherein the at least one acidic group is covalently linked to the at least one segment, wherein the acid functional compound functions as a wetting agent.

2 . The acid functional compound according to claim 1 , wherein the at least one segment is defined by the largest portion between two ester links, and wherein the at least one segment comprises an average number of ether links L between two adjacent ether units and an average number of ether units E, wherein a ratio R is defined according to formula (A): L/(E-1) and wherein, when E is larger than 1.0, R is smaller than 1.0.

3 . The acid functional compound according to claim 2 , wherein the ratio R is smaller than 0.9.

4 . The acid functional compound according to claim 1 , wherein the at least one segment is linked to a polymerization starter moiety comprising an amine group selected from a tertiary amine group, a salt of a tertiary amine group and a quaternary ammonium group.

5 . The acid functional compound according to claim 4 , wherein the polymerization starter moiety is directly linked to said at least one segment via a group selected from an ether group, an ester group, a secondary amide group, a tertiary amide group, a secondary amine group and a tertiary amine group.

6 . The acid functional compound according to claim 4 , wherein the polymerization starter moiety is a polyethylenimine.

7 . The acid functional compound according to claim 1 , wherein the at least one ether unit includes a unit of formula (III) —[CR 30 2 ] n —O—, wherein n is an integer of 2 or 3, and R 30 independent of each other represent organic groups having 1 to 25 carbon atoms or hydrogen.

8 . The acid functional compound according to claim 7 , wherein, in case n is equal to 2, at least one of the R 30 represents an ether group having the formula —R 31 —O—R 32 , wherein R 31 and R 32 independent of each other represent organic groups having 1 to 30 carbon atoms.

9 . The acid functional compound according to claim 1 , wherein the acid functional compound has the general formula:
Y(—X—W—Z) q (Ia),
wherein Y is represented by an organic group containing 1-500 carbon atoms, X is represented by O, NH and/or NR 1 , R 1 is independently selected and is represented by a chemical bond to a carbon atom of Y and/or an independently selected organic group containing 1-20 carbon atoms, W is one segment of the at least one segment i., q=1-100, and each Z is independently selected from hydrogen and moiety Z-a, each other each moiety Z-a is independently selected from an organic group containing 0-600 carbon atoms and at least one acidic group ii., wherein at least one Z is represented by moiety Z-a.

10 . The acid functional compound according to claim 9 , characterized in that each moiety Z-a is independently represented by general formula (II)
˜PO(V) n (OH) 2-n   (II)

with
each V independently represented by a chemical bond to an oxygen atom of the same molecule and/or a group OR 33 ,
each R 33 independently represented by an organic group containing 1 to 500 carbon atoms, and n is 0 or 1.

11 . The acid functional compound according to claim 10 , characterized in that n=0.

12 . The acid functional compound according to claim 1 that is present in salinized or partially salinized form.

13 . A composition comprising particles and an acid functional compound according to claim 1 .

14 . A method for producing an acid functional compound, the method comprising:
preparing a segment by reacting a cyclic ester and a cyclic ether together in a ring-opening polymerization reaction, wherein the ring-opening polymerization reaction is started by a polymerization starter compound comprising at least one functional group selected from a hydroxyl group, a secondary amine group and a primary amine group, and converting the segment of with an agent to covalently link the segment to at least one acidic group selected from a phosphoric acid group, an acidic phosphoric acid ester group, a sulfonic acid group, an acidic sulfonic acid ester group, and a carboxylic acid group, the method yielding an acid functional compound comprising i. at least one segment comprising at least one ether unit and at least one ester unit, wherein the at least one ether unit and the at least one ester unit are connected by an ether link or by an ester link, and wherein the sum of the number of the at least one ether unit and the at least one ester unit is at least three, and wherein the at least one ether unit and the at least one ester unit-are arranged in random order, and ii. at least one acidic group selected from a phosphoric acid group, an acidic phosphoric acid ester group, a sulfonic acid group, an acidic sulfonic acid ester group and a carboxylic acid group, wherein the at least one acidic group is covalently linked to the at least one segment.

15 . The method according to claim 14 , wherein the cyclic ester and the cyclic ether are added substantially simultaneously into a reaction mixture, which is maintained in reaction conditions.

16 . The method according to claim 14 , wherein the polymerization starter compound is added to a reaction mixture containing the cyclic ester and the cyclic ether, which reaction mixture is maintained in reaction conditions.

17 . The acid functional compound according to claim 2 , wherein the ratio R is smaller than 0.8.

18 . The acid functional compound according to claim 2 , wherein the ratio R is smaller than 0.7.

19 . The acid functional compound according to claim 10 , wherein each R 33 independently represents an organic group containing 1 to 35 carbon atoms.

Assignees

• Byk Chemie Gmbh

Inventors

• Okkel Andreas
• Giebelhaus Irina
• Jaunky Guillaume Wojciech
• Lorenz Markus

Classifications

• C09D167/00

  Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers · CPC title

• C09D167/08

  Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids · CPC title

• C08G65/3322

  acyclic · CPC title

• C08G65/327

  containing phosphorus · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title