RADIATION CURABLE NON-GELLED MICHAEL ADDITION REACTION PRODUCTS

• US 3,844,916 A
• Filed: 09/18/1972
• Issued: 10/29/1974
• Est. Priority Date: 09/18/1972
• Status: Expired due to Term

• Current Assignee: DSM Resins BV (DSM-Firmenich AG)
• Original Assignee: Joseph E. Gaske
• Inventors: Gaske, Joseph E.
• Primary Examiner(s): Tillman, Murray
• Assistant Examiner(s): Page, Thurman K.
• Application Number:
  US05/290,068
• Time in Patent Office: 771 Days
• Field of Search: 204/159.16,159.23,159.22 260/836,837
• US Class Current: 522/33
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: C08F 20/20 of polyhydric alcohols or polyhydric phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08G 59/1494 followed by a further chemical treatment thereof
• 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: Y10S 525/922 Polyepoxide polymer having been reacted to yield terminal ethylenic unsaturation

Abstract

Radiation curable, non-gelled Michael addition reaction products are obtained by reacting an amine containing at least one amino hydrogen atom with a stoichiometric excess of ethylenic material comprising a polyacrylate. These reaction products contain unreacted acrylate groups, and the radiation cure is not inhibited by oxygen.

Claims

1. AN ULTRAVIOLET CURABLE COMPOSITION COMPRISING:

(1) A RADIATION CURABLE LIQUID, NON-GELLED MICHAEL ADDITION REACTION PRODUCT OF AN ALIPHATICC AMINE CONTAINING A SINGLE AMINO HYDROGEN ATOM WITH A STOICHMETRIC EXCESS OF A POLYESTER OF ACRYLIC ACID WITH A POLYHYDRIC ALCOHOL, SAID AMINE CONSTITUTING AT LEAST 5 PERCENT OF SAID REACTION PRODUCT;

AND (2) A PHOTOSENSITIZER RENDERING THE PRODUCT SENSITIVE TO ULTRAVIOLET RADIATION.

2. An ultraviolet curable composition comprising:

(1) a radiation curable liquid, non-gelled Michael addition reaction product of an aliphatic amine containing a single amino hydrogen atom with a stoichiometric excess of a polyester of acrylic acid with a polyhydric alcohol, thus providing a reaction product containing unreacted acrylate groups, said amine constituting at least 0.5% of said composition; and

(2) a photosensitizer rendering the product sensitive to ultraviolet radiation.

3. A composition as recited in claim 2 in which said aliphatic amine is diethyl amine.

4. An ultraviolet curable composition comprising:

(1) a radiation curable liquid, non-gelled Michael addition reaction product of an aliphatic amine containing at least one amino hydrogen atom with a stoichiometric excess of a polyester of acrylic acid with a polyhydric alcohol, thus providing a reaction product containing unreacted acrylate groups, said amine constituting at least 0.5 percent of said composition; and

(2) a photosensitizer rendering the product sensitive to ultraviolet radiation.

5. A composition as recited in claim 4 in which said amine and said polyester are reacted at a temperature in excess of 48*C to insure complete reaction.

6. A composition as recited in claim 2 in which said amine is utilized in an amount of at least 1 percent, based on the weight of the composition.

7. A composition as recited in claim 2 in which said polyester is an hydroxy functional polyester with acrylic acid containing at least two acrylate groups per molecule.

8. An ultraviolet curable ink comprising a radiation curable liquid, non-gelled Michael addition reaction product of an aliphatic amine containing a single amino hydrogen atom with a stoichiometric excess of a polyester of acrylic acid with a polyhydric alcohol, said amine constituting at least 5 percent of said reaction product, said liquid reaction product having added thereto a photosensitizer rendering the product sensitive to ultraviolet radiation and a non-opaque pigment or dye.

9. A composition as recited in claim 2 in which said photosensitizer is selected from the group of benzophenone, acetophenone, benzoin and the methyl, butyl and isobutyl ethers of benzoin, and 10-thioxanthenone.