Curing for polyallophanate compositions through undercoat acid neutralization

Patent metadata

Field	Value
Publication number	US-10696775-B2
Application number	US-201815933500-A
Country	US
Kind code	B2
Filing date	Mar 23, 2018
Priority date	Mar 23, 2018
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

The present invention provides a system comprising an allophanate composition comprising a neutralized polyol, a polyuretdione resin, a tertiary amine catalyst, an additive package, and a reducer and a neutralized basecoat comprising an acid scavenger and a pigment. The resulting allophanate system may be used to make coatings, adhesives, castings, composites, and sealants in which clear-coating on neutralized pigmented basecoats is much improved in comparison to non-neutralized basecoats.

First claim

What is claimed is:

1. A system comprising:
an allophanate composition comprising a neutralized polyol, a polyuretdione resin, a tertiary amine catalyst, an additive package, and a reducer; and
a neutralized basecoat comprising an acid scavenger and a pigment.

2. The system according to claim 1 , wherein the tertiary amine is an amidine.

3. The system according to claim 1 , wherein the tertiary amine is selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,4,5,6-tetrahydro-1,2-dimethylpyrimidine, sodium-1,2,4-triazolide, 2-tert-butyl-1,1,3,3-tetramethylguanidine, and combinations thereof.

4. The system according to claim 1 , wherein the neutralized polyol comprises the reaction product of a polyol and an acid scavenger selected from the group consisting of carbodiimides and epoxies.

5. The system according to claim 4 , wherein the polyol is selected from the group consisting of polyalkylene ether polyols, polyester polyols, hydroxyl containing polycaprolactones, hydroxyl-containing (meth)acrylic polymers, polycarbonate polyols, polyurethane polyols, and combinations thereof.

6. The system according to claim 1 , wherein the neutralized basecoat comprises the reaction product of the basecoat with an acid scavenger selected from the group consisting of carbodiimides and epoxies.

7. The system according to claim 1 , wherein the pigment is selected from the group consisting of inorganic white pigments, inorganic chromatic pigments, iron oxide pigments, oxidic mixed-phase pigments, organic pigments, and inorganic black pigments.

8. The system according to claim 1 , wherein the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue pigments, ferric oxide yellow, diiron trioxide, N-[4-[[4-(dimethylamino)phenyl][4-(ethylamino)-1-naphthalenyl]methylene]-2,5-cyclohexadien-1-ylidene]-N-methylmethanaminium tungstatephosphate, iron oxide brown, transparent iron oxide pigments, chromium(III) oxide, chromium hydroxide green, nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, chromium iron brown, iron manganese black, spinel black, carbon black, and black iron oxide.

9. The system according to claim 1 , wherein the additive package includes one or more selected from the group consisting of flow control additives, wetting agents, pigments (colorants), and solvents.

10. The system according to claim 1 , wherein the polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.

11. The system according to claim 10 , wherein the isocyanate is selected from the group consisting of 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, 1-isocyanato-2-isocyanato-methyl cyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyanatocyclohexyl)methane, 1,3- and 1,4-bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)-methane, α,α,α′,α′-tetramethyl-1,3- and 1,4-xylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) bio-based, and, isomers of any of these.

12. The system according to claim 1 , wherein the reducer is selected from the group consisting of n-butyl acetate, ethyl acetate, 2-methoxy-1-methylethyl acetate, 1-methoxy-2-propyl acetate, 2-methoxy-1-propyl acetate, 2-ethoxyethyl acetate, n-heptane, methylcyclohexane, toluene, acetone, VM&P naphtha, naphtha, light aliphatic solvent naphtha, acetate, isobutyl acetate, mixed xylenes, ethylbenzene, methyl ethyl ketone, dimethyl ketone, methyl n-amyl ketone, methyl isobutyl ketone, 1,2,4 trimethyl benzene, isopropylbenzene, ethyl benzene, 1-chloro-4 (triflouromethyl) benzene, propylene glycol methyl ether, and ethyl-3-ethoxy propionate and combinations thereof.

13. One of a coating, an adhesive, a casting, a composite, and a sealant comprising the system made according to claim 1 .

14. A method of applying the system according to claim 1 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

15. A method of making an allophanate system comprising:
combining a neutralized polyol with a polyuretdione resin in the presence of a reducer, a tertiary amine catalyst, and an additive package, to produce an allophanate composition; and
contacting the allophanate composition with a neutralized basecoat comprising an acid scavenger and a pigment.

16. The method according to claim 15 wherein the tertiary amine catalyst comprises an amidine.

17. The method according to claim 15 , wherein the tertiary amine is selected from the group consisting of 1,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,4,5,6-tetrahydro-1,2-dimethylpyrimidine, sodium-1,2,4-triazolide, and 2-tert-butyl-1,1,3,3-tetramethylguanidine, and combinations thereof.

18. The method according to claim 15 , wherein the neutralized polyol comprises the reaction product of a polyol and an acid scavenger selected from the group consisting of carbodiimides and epoxies.

19. The method according to claim 18 , wherein the polyol is selected from the group consisting of polyalkylene ether polyols, polyester polyols, hydroxyl containing polycaprolactones, hydroxyl-containing (meth)acrylic polymers, polycarbonate polyols, polyurethane polyols, and combinations thereof.

20. The method according to claim 15 , wherein neutralized basecoat comprises the reaction product of a basecoat and an acid scavenger selected from the group consisting of carbodiimides and epoxies.

21. The method according to claim 15 , wherein the pigment is selected from the group consisting of inorganic white pigments, inorganic chromatic pigments, iron oxide pigments, oxidic mixed-phase pigments, organic pigments, and inorganic black pigments.

22. The method according to claim 15 , wherein the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue pigments, ferric oxide yellow, diiron trioxide, N-[4-[[4-(dimethylamino)phenyl][4-(ethylamino)-1-naphthalenyl]methylene]-2,5-cyclohexadien-1-ylidene]-N-methylmethanaminium tungstatephosphate, iron oxide brown, transparent iron oxide pigments, chromium(III) oxide, chromium hydroxide green, nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, chromium iron brown, iron manganese black, spinel black, carbon black, and black iron oxide.

23. The method according to claim 15 , wherein the additive package includes one or more selected from the group consisting of flow control additives, wetting agents, pigments (colorants), and solvents.

24. The method according to claim 15 , wherein the polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.

25. The method according to claim 24 ,

Assignees

• Covestro Llc
• Covestro Deutschland Ag

Inventors

• Ekin Alan
• Stempfle Florian Johannes

Classifications

• C08G18/027 Primary

  the polymeric products containing urethodione groups · CPC title

• C08G18/2063

  having two nitrogen atoms in the condensed ring system · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C08G18/1858

  having carbon-to-nitrogen double bonds · CPC title

• C09D7/63

  organic · CPC title