Sulfide extended epoxy resins and barrier coating applications thereof

Patent metadata

Field	Value
Publication number	US-9624380-B2
Application number	US-201214364820-A
Country	US
Kind code	B2
Filing date	Dec 14, 2012
Priority date	Dec 15, 2011
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

Provided is an oxygen barrier coating composition includes a resin including a compound of the following formula: where R1 is an alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group, where the alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group is substituted with one or more glycidyl groups, the alkyl group of R1 is further substituted with one or more OH, cycloalkyl, aryl, heteroaryl or glycidyl ethers or combinations thereof, and the cycloalkyl, aryl, alkyl aryl, glycol or polyol group of R1 optionally is substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ethers or combinations thereof, and R2 is an alkyl, cycloalkyl, aryl or heteroaryl group, where the alkyl, cycloalkyl, aryl or heteroaryl group is substituted with one or more mercapto groups, and the aryl, alkyl aryl, alkyl, cycloalkyl or heteroaryl group optionally is substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ethers or combinations thereof. Also provided are methods of reducing the transmission rate of a gas through a substrate, the method including applying the gas barrier coating composition provided herein on the substrate and drying the gas barrier coating composition.

First claim

What is claimed is:

1. An oxygen barrier coating composition comprising:
a) a polymer including a β-hydroxythioether linkage of the following formula:

wherein:
R1 is an alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group, wherein the alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group is substituted with one or more glycidyl groups, wherein the alkyl group of R1 is optionally further substituted with one or more OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof, and the cycloalkyl, aryl, alkyl aryl, glycol or polyol group of R1 optionally further is substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof; and
R2 is an alkyl, cycloalkyl, aryl, alkyl aryl or heteroaryl group, wherein the alkyl, cycloalkyl, aryl, alkyl aryl or heteroaryl group of R2 is substituted with one or more mercapto groups, wherein the aryl, alkyl aryl, alkyl, cycloalkyl or heteroaryl group optionally further is substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof, wherein the polymer including the β-hydroxythioether linkage is a reaction product of a multifunctional glycidyl ether and a multifunctional mercapto compound; and
b) water, or a solvent selected from the group consisting of aliphatic hydrocarbons, organic alcohols, organic ethers, organic carbonates, organic esters, halogenated aliphatic hydrocarbons, and combinations thereof.

2. The oxygen barrier coating composition of claim 1 , wherein R1 is an aryl group substituted with 1 to 14 glycidyl groups.

3. The oxygen barrier coating composition of claim 1 , wherein R2 is an aryl group or a heteroaryl group, the aryl and heteroaryl groups being substituted with 1 to 15 mercapto groups.

4. The oxygen barrier coating composition of claim 1 , wherein the oxygen barrier coating composition dried on a substrate at a coating weight of less than about 2 grams per square meter has an oxygen transmission rate of from about 0.05 cc/m 2 -day to about 50 cc/m 2 -day at a relative humidity of 50% or more.

5. The oxygen barrier coating composition of claim 4 , wherein the oxygen transmission rate is from about 0.5 cc/m 2 -day to about 25 cc/m 2 -day at a relative humidity of 50% or more.

6. The oxygen barrier coating composition of claim 4 , wherein the oxygen transmission rate is from about 1 cc/m 2 -day to about 15 cc/m 2 -day at a relative humidity of 50% or more.

7. The oxygen barrier coating composition of claim 4 , wherein the oxygen barrier coating composition has a coating weight of less than about 1.5 grams per square meter.

8. The oxygen barrier coating composition of claim 1 , wherein the oxygen barrier coating composition dried on a substrate at a coating weight of less than about 2 grams per square meter has an oxygen transmission rate of less than about 35 cc/m 2 -day at a relative humidity of 75%.

9. The oxygen barrier coating composition of claim 8 , wherein the oxygen transmission rate is less than about 10 cc/m 2 -day at a relative humidity of 75%.

10. The oxygen barrier coating composition of claim 1 , wherein the multifunctional glycidyl ether is selected from the group consisting of 1-phenyl-1,2-ethanediol diglycidyl ether, 1,2-benzenediol diglycidyl ether (pyrocatechol diglycidyl ether), 1,3-benzenediol diglycidyl ether (resorcinol diglycidyl ether), 1,4-benzenediol diglycidyl ether, methyl catechol diglycidyl ether, triglycidyl-p-aminophenol, diglycidyl 1,2-cyclohexanedicarboxylate, methyl resorcinol diglycidyl ether, 1,2,4-benzenetriol triglycidyl ether, 2-hydroxybenzylalcohol diglycidyl ether, 3-hydroxybenzylalcohol diglycidyl ether, diglycidyl phthaloyl diester, diglycidyl terephthaloyl diester, diglycidyl isophthaloyl diester, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, tetraphenylolethane glycidyl ether, meta-xylylenetetraglycidyl amine, 4-hydroxybenzyl-alcohol diglycidyl ether, 1,4-cyclohexanedimethanol-diglycidyl ether, mix of cis/trans, 3,5-dihydroxybenzylalcohol diglycidyl ether, Novolac Epoxy Resins, 1,2-benzene-dimethanol diglycidyl ether, 1,3-benzene-dimethanol diglycidyl ether, 1,4-benzene-dimethanol diglycidyl ether, tris(4-hydroxyphenyl)methane triglycidyl ether, 2-(2-hydroxyphenyl)ethanol diglycidyl ether, 2-(3-hydroxy-phenyl)-ethanol diglycidyl ether, 2-(4-hydroxy-phenyl)ethanol diglycidyl ether, 2-phenyl-1,2-propanediol diglycidyl ether, propylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether and biphenyl-4,4′-diglycidyl ether.

11. The oxygen barrier coating composition of claim 1 , wherein the multifunctional mercapto compound is selected from the group consisting of 2,5-dimercapto-1,3,4-thiadiazole, alkyl 2,5-dimercapto-1,3,4-thiadiazole, 5,5-dithiobis(1,3,4-thiadiazole-2(3H)-thione, 2-amino-5-mercapto-1,3,4-thiadiazole, 2-mercapto-5-methyl-thio-1,3,4-thiadiazole, 5-methyl-1,3,4-thiadiazole-2-thiol, dimercaptothiadiazole dimer, 1-methyl, 2,3-dimercaptobenzene, 1,2-dimercaptoethane, trimethylolpropane trithio-glycolate, pentaerythritol tetrathioglycolate, dipentaerythritol hexathioglycolate, 1,2-ethanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 1,10-decanedithiol, dipentene dimercaptan, ethylcyclohexyl dimercaptan, 1,4-benzenedithiol, 1,3-benzenedithiol, and 1,2-benzenedithiol.

12. A package for food, pharmaceuticals or cosmetics comprising the oxygen barrier coating composition of claim 1 .

13. A method of reducing the oxygen transmission rate of a substrate, comprising:
applying the oxygen barrier coating composition of claim 1 on the substrate, and
drying the oxygen barrier coating composition.

14. The method of claim 13 further comprising measuring the oxygen transmission rate of the oxygen barrier coating composition.

15. A method of coating a substrate with an oxygen barrier coating composition comprising:
a) providing an oxygen barrier coating composition comprising:
i) a polymer that includes a β-hydroxythioether linkage of the following formula:

 wherein:
R1 is an alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group, wherein the alkyl, cycloalkyl, aryl, alkyl aryl, glycol or polyol group is substituted with one or more glycidyl groups, wherein the alkyl group of R1 is optionally further substituted with one or more OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof, and the cycloalkyl, aryl, alkyl aryl, glycol or polyol group of R1 optionally further can be substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof, wherein the polymer including the β-hydroxythioether linkage is a reaction product of a multifunctional glycidyl ether and a multifunctional mercapto compound; and
R2 is an alkyl, cycloalkyl, aryl group or a heteroaryl group, wherein the alkyl, cycloalkyl, aryl group or heteroaryl group of R2 is substituted with one or more mercapto groups, wherein the aryl, alkyl aryl, alkyl, cycloalkyl or heteroaryl group optionally can be further substituted with one or more alkyl, OH, cycloalkyl, aryl, heteroaryl or glycidyl ether groups or combinations thereof; and
ii) water, or a solvent selected from the group consisting of aliphatic hydrocarbons, organic alcohols, organic ethers, organic carbonates, organic esters, halogenated aliphatic hydrocarbons, and combinations thereof;

b) applying the oxygen barrier coating compositio

Assignees

• Sun Chemical Corp

Inventors

• White Michael
• Rosen Josie
• Schottland Philippe
• Arcurio Ralph

Classifications

• C08G59/302 Primary

  containing sulfur · CPC title

• C08G59/3263

  containing sulfur · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C09D5/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes · CPC title

• B05D3/007

  After-treatment · CPC title