Radiation-curable coating compositions containing amide acrylate compounds

• US 4,227,979 A
• Filed: 10/05/1977
• Issued: 10/14/1980
• Est. Priority Date: 10/05/1977
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Gruber, Gerald W., Friedlander, Charles B., Dowbenko, Rostyslaw, Humke, Byron M.
• Primary Examiner(s): Danison, Walter C.
• Application Number:
  US05/839,686
• Time in Patent Office: 1,105 Days
• Field of Search: 526/304, 260/836, 260/837 R, 260/858, 560/222, 204/159.23, 204/159.18, 204/159.15, 204/156.16
• US Class Current: 522/14
• CPC Class Codes: C08F 120/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C09D 11/101 Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31935 Ester, halide or nitrile of addition polymer

Abstract

Radiation-curable coating compositions are disclosed which contain one or more amide acrylate compounds of the general formula: ##STR1## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester or acrylyloxy aliphatic ether, provided that X, Y and Z together have two, three or four acrylyloxy groups. The compositions are highly radiation-sensitive and very fast curing and form mar-resistant protective and decorative film coatings which are particularly useful as UV-cured overprint varnishes.

Claims

1. Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of one or more amide acrylate compounds having one nitrogen atom and being of the formula:

##STR6## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester formed by reaction of acrylating material with hydroxyl terminated aliphatic ester-containing intermediate resulting from the reaction of inner ester of hydroxy carboxylic acid and amino alcohol, or acrylyloxy aliphatic ether, provided that X, Y and Z together have two, three of four acrylyloxy groups.

2. The composition of claim 1 wherein

X is hydrogen,

Y and Z are each ##STR7##

3. The composition of claim 1 wherein

X is ##STR8## Y and Z are each ##STR9##

4. The composition of claim 1 wherein

X is ##STR10## Y and Z are each ##STR11##

5. The composition of claim 1 wherein

X is ##STR12## Y and Z are each ##STR13##

6. The composition of claim 1 wherein

X is ##STR14## Y and Z are each ##STR15##

7. The composition of claim 1 wherein

X is ##STR16## Y and Z are each ##STR17##

8. The composition of claim 1 wherein

X is ##STR18## Y and Z are each ##STR19##

9. The composition of claim 1 wherein

X is ##STR20## Y is --CH₃ Z is ##STR21##

10. The composition of claim 1 wherein

X is ##STR22## Y and Z are each ##STR23##

11. The composition of claim 1 comprising esterified or partially esterified reaction product of a lower alkyl polyhydric alcohol or an alkyl or aryl polyfunctional epoxide and acrylic acid or methacrylic acid.

12. The composition of claim 11 wherein said lower alkyl polyhydric alcohol is selected from the group consisting of diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexane diol, glycerol, neopentyl glycol, pentaerythritol, trimethylolethane, trimethylolpropane and 2,2-dimethyl-3-hydroxypropyl 2,2-dimethyl-3-hydroxypropionate.

13. The composition of claim 11 wherein said alkyl or aryl polyfunctional epoxide is selected from the group consisting of butane diol diglycidyl ether, neopentyl glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether and bisphenol A diglycidyl ether.

14. The composition of claim 1 comprising a reactive compound copolymerizable with said amide acrylate compound selected from the group consisting of styrenes, vinyl amides, esters of vinyl alcohols, acrylate esters, maleate esters and fumarate esters.

15. The composition of claim 1 comprising a substantially non-reactive solvent selected from the group consisting of xylene, toluene, 2-methoxyethanol, methyl isobutyl ketone and isopropyl alcohol.

16. The composition of claim 1 comprising a viscosity modifying agent selected from the group consisting of cellulose acetate butyrate, carboxymethyl cellulose, microcrystalline cellulose, fumed silica, castor oil based compositions, 12-hydroxystearic acid, alkyd polymers, acrylic polymers, and modified clays.

17. The composition of claim 1 comprising a surface tension reducing agent selected from the group consisting of branched lower alkyl acrylate polymers, fluorocarbon polymers and non-ionic alkyl ester surfactants, ethoxylated alkyl ester surfactants and ethoxylated phenol surfactants.

18. The composition of claim 17 wherein said branched lower alkyl acrylate polymer is poly(2-ethylhexylacrylate).

19. The composition of claim 1 comprising a slip-aid agent selected from the group consisting of polysiloxanes, fatty acids, fatty acid esters and waxes comprised of esters of long chain monohydric alcohols and long chain fatty acids.

20. The composition of claim 19 wherein said wax comprises a mixture of cetyl palmitate and related fatty acid esters.

21. The composition of claim 20 wherein said wax is spermaceti wax.

22. The composition of claim 1 comprising a photocatalyst system comprising one or more of a photosensitizer, a photopromoter or a photoinitiator, said photocatalyst system being present in an amount in the range of about 0.01 to about 20 percent by weight of polymerizable compound in said composition.

23. The composition of claim 22 wherein said photosensitizer is selected from the group consisting of benzil, anthraquinone, benzophenone, 3-methoxybenzophenone, anthrone, thioxanthone and chlorothioxanthone.

24. The composition of claim 22 wherein said photopromoter is selected from the group consisting of tertiary alkyl amines, tertiary alkanol amines and diamines.

25. The composition of claim 22 wherein said photoinitiator is selected from the group consisting of benzoin, methyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α

,α

-diethoxyacetophenone, α

,α

-dimethoxy-α

-phenyl-acetophenone, α

-chloroacetophenone and methyl phenylglyoxylate.

26. The composition of claim 3 wherein

(a) said prepolymer moiety is selected from the group consisting of a polyester polyol, a polyether polyol and a poly(hydrocarbyl siloxane) containing hydroxy functional groups pendent to the siloxane backbone;

(b) said isocyanato-containing compound is selected from the group consisting of aliphatic polyisocyanates and aromatic polyisocyanates; and

(c) said polyfunctional compound is acrylic acid or a hydroxyl-containing acrylic ester.

27. The composition of claim 1 comprising extender or hiding pigment.

28. Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula:

##STR24##

29. Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula:

##STR25##

30. Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising (A) from about one to 99 percent by weight of one or more amide acrylate compounds having one nitrogen atom and being of the formula:

##STR26## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester formed by reaction of acrylating material with hydroxyl terminated aliphatic ester-containing intermediate resulting from the reaction of inner ester of hydroxy carboxylic acid and amino alcohol, or acrylyloxy aliphatic ether, provided that X, Y and X together have two, three or four acrylyloxy groups; and

(B) a urethane acrylate co-curing agent derived from the stepwise reaction of;

(a) a prepolymer moiety of molecular weight 300 to 3,000 having a plurality of hydroxyl functional groups,

(b) a compound having a plurality of isocyanato groups, a portion of said isocyanato groups reactive with said prepolymer moiety hydroxyl functional groups, and

(c) a polyfunctional compound containing at least one functional group which is reactive with an isocyanato group and which polyfunctional compound after reaction with said isocyanato group provides at least one ethylenic functional group in said reaction product.