Organotin copolymers as polymeric crosslinking catalysts

Patent metadata

Field	Value
Publication number	US-11976209-B2
Application number	US-201917295932-A
Country	US
Kind code	B2
Filing date	Nov 22, 2019
Priority date	Nov 22, 2018
Publication date	May 7, 2024
Grant date	May 7, 2024

Abstract

Described herein is a (meth)acrylic copolymer including a polymeric backbone and at least two kinds of side chains (S1) and (S2) attached to the polymeric backbone, which are different from each other, namely one or more side chains (S1) including at least one tin-containing moiety and one or more side chains (S2) bearing at least one ester group of formula —O—C(═O)—R 1 , where R 1 is a linear or branched, saturated or unsaturated, acyclic aliphatic residue having at least 18 carbon atoms, a method of preparing the copolymer, a method of using the copolymer as catalyst in crosslinking reactions in coating compositions and/or for lengthening the pot life of coating compositions and/or for lowering the curing temperatures of coating compositions, a coating composition including the copolymer and a method of coating a substrate including applying the coating composition to a substrate.

First claim

The invention claimed is:

1. A (meth)acrylic copolymer comprising a polymeric backbone and at least two kinds of side chains (S1) and (S2) attached to said polymeric backbone, which are different from each other, wherein
one or more side chains (S1) comprise at least one tin-containing moiety and
one or more side chains (S2) heaving bear at least one ester group of formula —O—C(═O)—R 1 , wherein R 1 is a linear or branched, saturated or unsaturated, acyclic aliphatic residue having at least 18 carbon atoms.

2. The copolymer according to claim 1 , characterized in that the relative molar ratio of at least one structural unit (SU1), which contains the one or more side chains (S1), to at least one structural unit (SU2), which contains the one or more side chains (S2), in the (meth)acrylic copolymer is in the range of from 15:1 to 1:2.5.

3. The copolymer according to claim 1 , characterized in that the amount of structural units (SU1), which contain the one or more side chains (S1), is at least 20 mole-%, based on the total amount of all structural units of the copolymer, and in that the amount of structural units (SU2), which contains the one or more side chains (S2), is at least 10 mole-% based on the total amount of all structural units of the copolymer.

4. The copolymer according to claim 1 , characterized in that the one or more side chains (S1 ) are represented by the part structure (PS1)

wherein
the symbol denotes a covalent bond of part structure (PS1) to the backbone of the copolymer,
parameter a is 0 or 1 and
R 2 , R 3 and R 4 independently of one another represent a linear, saturated, alkyl group with 1 to 30 carbon atoms, a branched, saturated, alkyl group with 3 to 30 carbon atoms, an aryl group with 6 to 30 carbon atoms, or an alkylaryl group or arylalkyl group, in each case with 7 to 30 carbon atoms.

5. The copolymer according to claim 4 , characterized in that parameter a is 1 and R 2 , R 3 and R 4 independently of one another represent a linear, saturated, alkyl group with 1 to 20 carbon atoms or a branched, saturated, alkyl group with 3 to 20 carbon atoms.

6. The copolymer according to claim 1 , characterized in that R 1 is a linear or branched, saturated or unsaturated, acyclic aliphatic residue having from 18 to 60 carbon atoms.

7. The copolymer according to claim 1 , characterized in that the one or more side chains (S2) are represented by the part structure (PS2)

wherein
the symbol denotes a covalent bond of part structure (PS2) to the backbone of the copolymer,
parameter b is 0 or 1,
parameter c is in the range of from 2 to 20,
R 1 is a linear or branched, saturated or unsaturated, acyclic aliphatic residue having at least 18 carbon atoms,
each R 5 independently represents hydrogen, hydroxyl, a linear, saturated, alkyl group with 1 to 30 carbon atoms or a branched, saturated, alkyl group with 3 to 30 carbon atoms, and
each R 6 independently represents hydrogen, a linear, saturated, alkyl group with 1 to 30 carbon atoms or a branched, saturated, alkyl group with 3 to 30 carbon atoms.

8. The copolymer according to claim 7 , characterized in that parameter b is 1, parameter c is in the range of from 2 to 10, each R 5 independently represents hydrogen or hydroxyl, and each R 6 represents hydrogen.

9. The copolymer according to claim 1 , characterized in that it has at least one further kind of side chains (S3) attached to its polymeric backbone, which are different from both side chains (S1) and (S2), wherein
one or more side chains (S3) being are represented by the part structure (PS3)

wherein R 7 denotes a linear, saturated, alkyl group with 1 to 30 carbon atoms, a branched, saturated, alkyl group with 3 to 30 carbon atoms, an aryl group with 6 to 30 carbon atoms, or an alkylaryl group or arylalkyl group, in each case with 7 to 30 carbon atoms.

10. The copolymer accordingto claim 9 , characterized in that it contains structural units (SU1), (SU2) and (SU3), wherein (SU1) contains the at least one side chain (S1), (SU2) contains the at least one side chain (S2), and (SU3) contains at least one side chain (S3)and in that, based on the total quantity of structural units (SU1), (SU2)and (SU3), it contains the following proportions in mole-%
10 to 70 mole-% of the structural units (SU1)
10 to 40 mole-% of the structural units (SU2) and
5 to 60 mole-% of the structural units (SU3),
wherein the total content of structural units (SU1) and (SU2) and (SU3) in the copolymer adds up 100 mole %.

11. A method of preparing the (meth)acrylic copolymer according to claim 1 , the method comprisingat least one step, wherein
(s1) at least one (meth)acrylic monomer comprisingat least one tin-containing moiety, and
(s2) at least one (meth)acrylic monomer bearing at least one estergroup of formula —O—C(═O)—R 1 , wherein R 1 is a linear or branched, saturated or unsaturated, acyclicaliphatic residue having at least 18 carbon atoms, and optionally (s3) at least one ethylenicallyunsaturated monomer, which is different from both monomers
(s1) and (s2),
are copolymerizedto form the copolymer,
or wherein
(s1) at least one (meth)acrylic monomer comprisingat least one tin-containing moiety, and
(s2) at least one (meth)acrylic monomer bearing at least one functional group capable of being reacted with a carboxylic acid that provides an ester group of formula —O—C(═O)—R 1 , wherein R 1 is a linear or branched, saturated or unsaturated, acyclicaliphatic residue having at least 18 carbon atoms, and
optionally (s3) at least one ethylenicallyunsaturated monomer, which is different from both monomers (s1) and (s2),
are copolymerized to form the copolymer followed by reacting the at least one functional group of the structural unit obtained from the at least one monomer (s2) with the carboxylic acid that provides an ester group of formula —O—C(═O)—R 1 , wherein R 1 is a linear or branched, saturated or unsaturated, acyclicaliphatic residue having at least 18 carbon atoms, in a polymer analogous reaction.

12. A method of using the (meth)acrylic copolymer according to claim 1 , the method comprising using the (meth)acrylic copolymer as a catalyst in crosslinking reactions, in coating compositions and/or for lengthening the pot life of coating compositions and/or for lowering the curing temperatures of coating compositions.

13. A coating composition comprising at least one polymer as binder component (a) and at least one (meth)acrylic copolymer according claim 1 as component (b), wherein the polymer of the binder component (a) is different from the (meth)acrylic copolymer of component (b).

14. The coating composition according to claim 13 , characterized in that it contains the at least one (meth)acrylic copolymer as component (b) in an amount of from 0.1 to 5 wt.-%, based on the total weight of the coating composition.

15. A method of coating a substrate comprising at least one step (1), wherein step (1) comprises applying a coating composition according to claim 13 to a substrate.

Assignees

• Basf Coatings Gmbh

Inventors

• Zhu Zhongliang

Classifications

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F8/10

  Acylation · CPC title

• C08F8/14

  Esterification · CPC title

• C08F220/20 Primary

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F220/283

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title