Thermolatent catalyst and its use in curable compositions

Patent metadata

Field	Value
Publication number	US-10773243-B2
Application number	US-201715698037-A
Country	US
Kind code	B2
Filing date	Sep 7, 2017
Priority date	Sep 7, 2017
Publication date	Sep 15, 2020
Grant date	Sep 15, 2020

Abstract

Tin-containing catalysts are provided comprising a compound of formula I.
I:

L1, L2, L3, and L4 are each independently selected from —O—, —S—, —OC(═O)—, —OC(═S)—, —SC(═O)—, —SC(═S)—, —OS(═O) 2 O—, —OS(═O) 2 — —N(R6)-, and —OP(═O)(R6)-, wherein R6 represents hydrogen or a monovalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms. R1, R2, R3, R1′, R2′, and R3′ each independently represent a divalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms; and R4, R5, R4′, and R5′ each independently represent hydrogen or a monovalent residue derived from reaction of a respective N—H group with an isocyanate, an ethylenically unsaturated compound, a lactone, a dilactone, a thiolactone, a lactam, a thiolactam, a carboxylic acid or derivative thereof, or an epoxide. Also provided are curable compositions containing these catalysts and methods of controlling the rate of cure of curable compositions.

First claim

What is claimed is:

1. A compound of formula I:

wherein
L1, L2, L3, and L4 are each independently selected from —O—, —S—, —OC(═O)—, —OC(═S)—, —SC(═O)—, —SC(═S)—, —OS(═O) 2 O—, —OS(═O) 2 — —N(R6)-, and —OP(═O)(R6)-, wherein R6 represents hydrogen or a monovalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms, which can optionally contain one or more heteroatom selected from the group consisting of oxygen, sulfur and nitrogen;
R1, R2, R3, R1′, R2′, and R3′ each independently represent a divalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms, which can optionally contain one or more heteroatom selected from the group consisting of oxygen, sulfur and nitrogen; and
R4, R5, R4′, and R5′ each independently represent hydrogen or a monovalent residue derived from reaction of a respective N—H group with an isocyanate, an ethylenically unsaturated compound, a lactone, a dilactone, a thiolactone, a lactam, a thiolactam, a carboxylic acid or derivative thereof, or an epoxide.

2. The compound of claim 1 comprising a reaction product of:
(i) a tin(IV) compound; and
(ii) an adduct of:
(a) a compound having two secondary amine groups and two additional active hydrogen-containing functional groups that may be the same as or different from the amine groups and from each other; and
(b) a reactant comprising at least one of an isocyanate, an ethylenically unsaturated compound, a lactone, a dilactone, a thiolactone, a lactam, a thiolactam, a carboxylic acid or derivative thereof, and an epoxide.

3. The compound of claim 2 , wherein the tin(IV) compound (i) comprises at least one of tin(IV) chloride, tin(IV) isopropoxide and tin(IV) tertbutoxide.

4. The compound of claim 2 , wherein the compound (a) having two secondary amine groups and two additional active hydrogen-containing functional groups comprises N, N′-bis(hydroxyethyl) ethylenediamine.

5. The compound of claim 2 , wherein the reactant (b) comprises at least one of 2-ethylhexyl acrylate and butyl acrylate.

6. A curable composition comprising:
(A) a first reactive compound comprising at least one of a polyisocyanate, polyepoxide, polyol, and polyacid;
(B) a second reactive compound comprising at least one of hydroxyl, acid, and thiol reactive functional groups; and
(C) a catalyst component comprising at least one compound of claim 1 .

7. The curable composition of claim 6 , wherein the second reactive compound (B) comprises at least one of an acrylic polymer, a polyether polymer, polyurethane and a polyester polymer.

8. The curable composition of claim 6 , wherein the first reactive compound (A) comprises a curing agent comprising reactive isocyanate functional groups, and the second reactive compound (B) comprises a film-forming compound comprising functional groups reactive with the reactive isocyanate functional groups in (A), and wherein the curable composition is a film-forming composition.

9. The curable composition of claim 8 , wherein the curing agent comprises at least one of a diisocyanate and a triisocyanate.

10. The curable composition of claim 8 , wherein the film-forming compound comprises at least one of an acrylic polyol, a polyether polyol, a polyurethane polyol, and a polyester polyol.

11. A method of controlling the rate of cure of a curable composition comprising adding to the curable composition a catalyst component comprising at least one compound of formula I:

wherein
L1, L2, L3, and L4 are each independently selected from —O—, —S—, —OC(═O)—, —OC(═S)—, —SC(═O)—, —SC(═S)—, —OS(═O) 2 O—, —OS(═O) 2 — —N(R6)-, and —OP(═O)(R6)-, wherein R6 represents hydrogen or a monovalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms, which can optionally contain one or more heteroatom selected from the group consisting of oxygen, sulfur and nitrogen;
R1, R2, R3, R1′, R2′, and R3′ each independently represent a divalent aliphatic, araliphatic, cycloaliphatic or aromatic group having up to 20 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen; and
R4, R5, R4′, and R5′ each independently represent hydrogen or a monovalent residue derived from reaction of a respective N—H group with an isocyanate, an ethylenically unsaturated compound, a lactone, a dilactone, a thiolactone, a lactam, a thiolactam, a carboxylic acid or derivative thereof, or an epoxide; and wherein the curable composition comprises:
(A) a first reactive compound comprising at least one of a polyisocyanate, polyepoxide, polyol, and polyacid;
(B) a second reactive compound comprising at least one of hydroxyl, acid, and thiol reactive functional groups.

12. The method of claim 11 , wherein after adding the catalyst component to the curable composition the method further comprises applying the curable composition to a substrate as a coating to form a coated substrate; and exposing the coated substrate to conditions for a time sufficient to at least partially cure the curable composition.

13. The method of claim 11 , wherein the curable composition is a film-forming composition, the first reactive compound (A) comprises a curing agent comprising reactive isocyanate functional groups, and the second reactive compound (B) comprises a film-forming compound comprising functional groups reactive with the reactive isocyanate functional groups in (A).

14. The method of claim 13 , wherein the curing agent comprises at least one of a diisocyanate and a triisocyanate.

15. The method of claim 13 , wherein the film-forming compound comprises at least one of an acrylic polyol, a polyether polyol, a polyurethane polyol, and a polyester polyol.

16. A coated substrate comprising an at least partially cured coating layer formed from the curable composition of claim 6 .

Assignees

• Ppg Ind Ohio Inc

Inventors

• Zhou Hongying
• Moravek Scott J
• Schwartzmiller Davina J
• Deng Jun
• Martz Jonathan Thomas

Classifications

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title

• C08G18/58

  Epoxy resins {(C08G18/42, C08G18/48 take precedence; reaction products of epoxy resins with at least equivalent amounts of compounds containing active hydrogen C08G18/6407, with at least equivalent amounts of amines C08G18/6415; polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen C08G18/003)} · CPC title

• C08G18/24 Primary

  of tin · CPC title

• C07F7/22 Primary

  Tin compounds · CPC title

• B01J2540/40

  Non-coordinating groups comprising nitrogen · CPC title