Curable film-forming compositions containing encapsulated catalyst components

Patent metadata

Field	Value
Publication number	US-9650480-B2
Application number	US-201514686825-A
Country	US
Kind code	B2
Filing date	Apr 15, 2015
Priority date	Apr 15, 2015
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

Curable film-forming compositions are provided. The compositions comprise (a) a curing agent comprising reactive functional groups; (b) a film-forming compound comprising functional groups reactive with the reactive functional groups in (a); and (c) a catalyst component added to the curable film-forming composition as a dispersion of micelles in a continuous phase. The catalyst component (c) comprises a catalyst compound contained within or encapsulated by a carrier, and the catalyst compound and carrier together form the micelles in the continuous phase. The carrier comprises block copolymers that comprise at least one hydrophobic block derived from hydrophobic monomers and at least one hydrophilic block derived from (1) hydrophilic monomers and/or (2) monomers containing groups that may be rendered hydrophilic after polymerization.

First claim

What is claimed is:

1. A curable film-forming composition comprising:
(a) a curing agent comprising reactive functional groups;
(b) a film-forming compound comprising functional groups reactive with the reactive functional groups in (a); and
(c) a catalyst component added to the curable film-forming composition as a dispersion of non-crosslinked micelles in a continuous phase, wherein the catalyst component comprises a catalyst compound contained within or encapsulated by a carrier, and the catalyst compound and carrier together form the micelles in the continuous phase, and wherein the carrier comprises block copolymers that comprise at least one hydrophobic block derived from hydrophobic monomers and at least one hydrophilic block derived from (1) hydrophilic monomers and/or (2) monomers containing groups that may be rendered hydrophilic after polymerization.

2. The curable film-forming composition of claim 1 , wherein the hydrophobic blocks form a core of each micelle, the hydrophilic blocks form a shell of each micelle, and the continuous phase of the dispersion is aqueous and/or a polar solvent.

3. The curable film-forming composition of claim 2 , wherein the catalyst compound comprises one or more of dibutyltin dilaurate, calcium naphthanate, cesium naphthanate, cobalt naphthanate, dibutyl tin diacetate, dibutyl tin dioctoate, dibutyl tin naphthanate, bismuth ethylhexanoate, a zirconium carboxylate, and zinc acetylacetonate.

4. The curable film-forming composition of claim 2 , wherein the block copolymers are prepared via a RAFT or NMP polymerization process.

5. The curable film-forming composition of claim 1 , wherein the hydrophilic blocks form a core of each micelle, the hydrophobic blocks form a shell of each micelle, and the continuous phase of the dispersion is nonaqueous and/or nonpolar.

6. The curable film-forming composition of claim 5 , wherein the catalyst compound comprises one or more of dibutyltin oxide, triethylamine, 1,4-diazabicyclo[2.2.2] octane, 1,8-diazabicyclo[5.4.0] undec-7-ene, N-ethylmorpholine dodecylbenzene sulfonic acid, dimethylethanolamine, and trihydroxypropyl phosphine.

7. The curable film-forming composition of claim 1 , wherein the hydrophobic monomers include one or more of n-butyl (meth)acrylate, isobutyl (meth)acrylate, lauryl (meth)acrylate, 2-ethylhexyl (meth) acrylate, stearyl (meth) acrylate, styrene, isobornyl (meth)acrylate, and cyclohexyl (meth)acrylate.

8. The curable film-forming composition of claim 1 , wherein the hydrophilic monomers or monomers containing groups that may be rendered hydrophilic after polymerization include one or more of methoxypolyethylene glycol (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, hydroxy functional adducts of caprolactone, (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, isopropyl acrylamide, methyl acrylate, acrylonitrile, and dimethylaminoethyl(meth)acrylate.

9. The curable film-forming composition of claim 1 , wherein the catalyst compound is present in the catalyst component (c) in an amount of 0.1 to 90 percent by weight, based on the total weight of solids in the catalyst component (c).

10. The curable film-forming composition of claim 1 , wherein the composition is a two-package composition, and the catalyst component (c) is present with the curing agent (a) in a first package and/or with the film-forming compound (b) in a second package.

11. A curable film-forming composition comprising:
(a) a curing agent comprising reactive functional groups;
(b) a film-forming compound comprising functional groups reactive with the reactive functional groups in (a); and
(c) a catalyst component added to the curable film-forming composition as a dispersion of micelles in a continuous phase, wherein the catalyst component comprises a catalyst compound contained within or encapsulated by a carrier, and the catalyst compound and carrier together form the micelles in the continuous phase, and wherein the carrier comprises block copolymers that are prepared via an ATRP polymerization process and that comprise at least one hydrophobic block derived from hydrophobic monomers and at least one hydrophilic block derived from (1) hydrophilic monomers and/or (2) monomers containing groups that may be rendered hydrophilic after polymerization.

12. The curable film-forming composition of claim 11 , wherein the hydrophobic blocks form a core of each micelle, the hydrophilic blocks form a shell of each micelle, and the continuous phase of the dispersion is aqueous and/or a polar solvent.

13. The curable film-forming composition of claim 12 , wherein the block copolymers are not covalently crosslinked into a microgel.

14. The curable film-forming composition of claim 12 , wherein the catalyst compound comprises one or more of triphenyl phosphine, methyl dicocoamine, dibutyltin dilaurate, calcium naphthanate, cesium naphthanate, cobalt naphthanate, dibutyltin diacetate,dibutyl tin dioctoate, dibutyl tin naphthanate, bismuth ethylhexanoate, a zirconium carboxylate, and zinc acetylacetonate.

15. The curable film-forming composition of claim 11 , wherein the hydrophilic blocks form a core of each micelle, the hydrophobic blocks form a shell of each micelle, and the continuous phase of the dispersion is nonaqueous and/OR nonpolar.

16. The curable film-forming composition of claim 15 , wherein the catalyst compound comprises one or more of dibutyltin oxide, triethylamine, 1,4-diazabicyclo[2.2.2] octane, 1,8-diazabicyclo[5.4.0] undec-7-ene, N-ethylmorpholine dodecylbenzene sulfonic acid, dimethylethanolamine, and trihydroxypropyl phosphine.

17. The curable film-forming composition of claim 11 , wherein the hydrophobic monomers include one or more of n-butyl (meth)acrylate, isobutyl (meth)acrylate, lauryl (meth)acrylate, 2-ethylhexyl (meth) acrylate, stearyl (meth) acrylate, styrene, isobornyl (meth)acrylate, and cyclohexyl (meth)acrylate.

18. The curable film-forming composition of claim 11 , wherein the hydrophilic monomers or monomers containing groups that may be rendered hydrophilic after polymerization include one or more of methoxypolyethylene glycol (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, hydroxy functional adducts of caprolactone, (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, isopropyl acrylamide, methyl acrylate, acrylonitrile, and dimethylaminoethyl(meth)acrylate.

19. The curable film-forming composition of claim 11 , wherein the catalyst compound is present in the catalyst component (c) in an amount of 0.1 to 90 percent by weight, based on the total weight of solids in the catalyst component (c).

20. The curable film-forming composition of claim 11 , wherein the composition is a two-package composition, and the catalyst component (c) is present with the curing agent (a) in a first package and/or with the film-forming compound (b) in a second package.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Moravek Scott J
• Bowles Steven
• Schwartzmiller Davina
• Wang Wei
• Fenn David
• Powell Adam Bradley

Classifications

• C08F2438/01

  Atom Transfer Radical Polymerization [ATRP] or reverse ATRP · CPC title

• C08J2333/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C09D153/00 Primary

  Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers · CPC title

• C08F4/10

  of alkaline earth metals, zinc, cadmium, mercury, copper or silver · CPC title

• C08F4/12

  of boron, aluminium, gallium, indium, thallium or rare earths · CPC title