Thermosetting coating composition

Patent metadata

Field	Value
Publication number	US-8969489-B2
Application number	US-201113205152-A
Country	US
Kind code	B2
Filing date	Aug 8, 2011
Priority date	Aug 10, 2010
Publication date	Mar 3, 2015
Grant date	Mar 3, 2015

Abstract

The invention is a thermosetting coating composition comprised of an aliphatic polycarbonate resin and a cross linker. The aliphatic polycarbonate resins are derived from hydroxyl containing compounds including 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) and 1,4-cyclohexane dimethanol (CHDM). The coatings made of these polycarbonates exhibit exceptional toughness; they possess a high degree of hardness while maintaining a high level of flexibility/impact resistance. These polycarbonate resins also exhibited better hydrolytic stability as compared to their polyester counterparts.

First claim

We claim:

1. A liquid thermosetting coating composition comprising an aliphatic polycarbonate resin and a cross linking compound, said aliphatic polycarbonate resin derived from aliphatic hydroxyl containing compounds in the presence of a catalyst, said aliphatic hydroxyl compounds comprising:
A. 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD); and
B. 1,4-cyclohexane dimethanol (CHDM); and

wherein the catalyst used to obtain the aliphatic polycarbonate is present in an amount ranging from 0.0001 wt % to 0.03 wt % based on the total weight of the aliphatic hydroxyl compounds; and wherein molar ratio of TMCD to CHDM residues present in the polycarbonate resin is:
(i) in the range of 8:2 to 3:7 if the only aliphatic hydroxyl compounds used are TMCD and CHDM or
(ii) otherwise is in the range of 9:1 to 1:9.

2. The liquid composition of claim 1 , wherein the polyhydroxyl compounds further comprise a third aliphatic polyhydroxyl compound different from TMCD and CHDM.

3. The liquid composition of claim 2 , wherein the amount of third polyhydroxyl compound residue present in the polycarbonate resin is up to 50 mole % based on total residues of hydroxyl containing compounds.

4. The liquid composition of claim 3 , wherein the third polyhydroxyl compound comprises neopentyl glycol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, heptaethylene glycol, octaethylene glycol, nonaethylene glycol, decaethylene glycol, 1,3-propanediol, 2,4-dimethyl-2-ethyl-hexane-1,3-diol, 2,2-dimethyl-1,2-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 2-ethyl-1,3-hexanediol, 2,2,4,4-tetramethyl-1,6-hexanediol, thiodiethanol, 2,2,4-trimethyl 1,3-pentanediol, 2,4-diethyl-1,5-pentanediol, norbornene dimethanol, hydroxypivalyl hydroxypivalate, 1,10-decanediol, or hydrogenated bisphenol A.

5. The liquid composition of claim 4 , wherein the third polyhydroxyl compound comprises 2-butyl-2-ethyl-1,3-propanediol (BEPD).

6. The liquid composition of claim 3 , wherein the third polyhydroxyl compound comprises trimethylolethane, trimethylolpropane, hexanetriol, pentaerythritol, 1,2,4-cyclohexanetrimethanol, 1,3,5-cyclohexanetrimethynol or1,2,4,5-cyclohexanetetramethanol.

7. The liquid composition of claim 6 , wherein the amount of the residues of said third aliphatic polyhydroxyl compound is up to 20 mole %, based on the total residues of polyhydroxyl compounds.

8. The liquid composition of claim 1 , wherein the aliphatic polycarbonate is an amorphous solid or viscous liquid at about 25° C.

9. The liquid composition of claim 1 , wherein the aliphatic polycarbonate is prepared by performing an ester exchange between a dialkyl carbonate, or alkylene carbonate, and units (A) and (B).

10. The liquid composition of claim 9 , wherein the dialkyl carbonate comprises dimethylcarbonate or diethylcarbonate.

11. The liquid composition of claim 9 , wherein the ester exchange reaction is performed by melt polymerization in the presense of said catalyst, said catalyst comprising an ester exchange catalyst.

12. The composition of claim 11 , wherein the ester exchange catalyst comprises an alkali metal, alkali metal hydroxide, alkali metal alkoxide, alkali metal carbonate, alkaline earth metal carbonate, zinc borate, zinc oxide, lead silicate, lead carbonate, antimony trioxide, germanium dioxide, cerium trioxide, or aluminum isopropoxide.

13. The composition of any one of claims 1 and 2 - 12 , wherein the amount of catalyst is from 0.001 wt. % to 0.03 wt %, based on the total weight of the aliphatic hydroxyl compounds employed.

14. The composition of claim 13 , wherein the amount of catalyst is from 0.001 wt. % to 0.025 wt. %, based on the total weight of the aliphatic hydroxyl compounds employed.

15. The liquid composition of claim 1 , wherein the crosslinker comprises a melamine compound or an isocyanate or isocyanurate compound.

16. The liquid composition of claim 1 , wherein the crosslinker comprises hexamethoxymethylmelamine, tetramethoxymethylbenzoguanamine, tetramethoxymethylurea, mixed butoxy/methoxy substituted melamines, toluene diisocyanate, isocyanurates of toluene diisocyanate, diphenylmethane 4,4′-diisocyanate, isocyanurates of 4,4′-diisocyanate, methylenebis-4,4′-isocyanatocyclohexane, isophorone diisocyanate, isocyanurates of isophorone diisocyanate, 1,6-hexamethylene diisocyanate, isocyanurates of 1,6-hexamethylene diisocyanate, 1,4-cyclohexane diisocyanate, p-phenylene diisocyanate, and triphenylmethane 4,4′,4″-triisocyanate, tetramethyl xylene diisocyanate, metaxylene diisocyanate, polyisocyanates, or isocyanate terminated adducts of diols and polyols.

17. The liquid composition of claim 1 , wherein said composition comprises an un-pigmented transparent clear coat, a pigmented primer, a basecoat, or a topcoat.

Assignees

• Zhou Jianhui
• Johnson Angela Jones
• Eastman Chem Co

Inventors

• Zhou Jianhui
• Johnson Angela Jones

Classifications

• C08G64/305

  and alcohols · CPC title

• C09D169/00 Primary

  Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates · CPC title

• C08K5/34922

  Melamine; Derivatives thereof · CPC title

• C08G64/0208 Primary

  saturated · CPC title

• H01S3/097 Primary

  by gas discharge of a gas laser · CPC title