Preparing radiation-curable, urethane-functional prepolymers

• US 6,177,535 B1
• Filed: 09/21/1998
• Issued: 01/23/2001
• Est. Priority Date: 09/22/1997
• Status: Expired due to Term

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Schwalm, Reinhold, Beck, Erich, Paulus, Wolfgang, Menzel, Klaus, Königer, Rainer, Reich, Wolfgang, Lokai, Matthias
• Primary Examiner(s): COONEY, JOHN M
• Application Number:
  US09/157,615
• Time in Patent Office: 855 Days
• Field of Search: 560/330, 560/335, 560/355, 427/385.5, 528/59, 528/75, 528/49, 528/67, 522/90, 522/174
• US Class Current: 528/49
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/7831 containing biuret groups
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds

Abstract

A process for preparing radiation-curable, urethane-functional prepolymers by reacting an isocyanate-functional component A with an OH-containing component B, wherein either component A embraces two different isocyanate compounds A1 or one isocyanate compound A1 and at least one isocyanate compound A2 or component B embraces at least two different compounds B1. Also, the prepolymers obtainable by the process and the radiation-curable formulations comprising them. Furthermore, the use of the radiation-curable formulations for coating substrates, a method of coating substrates, and the coated substrates themselves.

Claims

1. A process for preparing radiation-curable, urethane-functional prepolymers PU, the process comprising

reacting an isocyanate-functional component A with an OH-containing component B, wherein

the component A comprises at least one trifunctional isocyanate compound A1 with or without one or more difunctional isocyanate compounds A2;

the OH-containing component B comprises at least one ethylenically unsaturated compound B1 having at least one reactive OH group with or without different OH-containing compounds B2; and

either component A1 embraces at least two different isocyanate compounds A1a and A1b in a weight ratio of 1;

3 to 3;

1 or component A embraces one isocyanate compound A1 and at least one isocyanate compound A2 in a molar ratio of 10;

1 to 1;

5,

wherein the compound A1 is selected from the group consisting of cyanurate of hexamethylene diisocyanate, cyanurate of isophorone diisocyanate biuret of hexamethylene diisocyanate, and biuret of isophorone diisocvanate.

2. A process as claimed in claim 1, wherein the compound B1 is an ester of acrylic or methacrylic acid with an aliphatic di- or polyol, the ester still having at least one free OH group.

3. A process as claimed in claim 2, wherein the compound B1 is selected from 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, 1,4-butanediol (meth)acrylate, trimethylolpropane mono- and di(meth)acrylate and pentaerythritol tri(meth)acrylate.

4. A process as claimed in claim 2, wherein the component B comprises at least two different compounds B1a and B1b with a molar ratio B1a:

B1b in the range from 1;

10 to 10;

1.

5. A radiation-curable, urethane-functional prepolymer PU produced by a process as claimed in claim 1.

6. A radiation-curable formulation comprising at least one prepolymer PU as claimed in claim 5.

7. A radiation-curable formulation as claimed in claim 6, comprising

i) from 20 to 90% by weight of said at least one prepolymer PU,

ii) from 10 to 80% by weight of at least one low molecular mass compound containing at least one ethylenically unsaturated, polymerizable double bond (component S), and

iii) of up to 20% by weight, based on the overall weight of components PU and S, of auxiliaries, with the proviso that the amounts by weight of component PU and S add up to 100% by weight.

8. A method of coating a substrate, which comprises applying a prepolymer PU as claimed in claim 5 to the substrate which is to be coated, removing any solvent and then carrying out curing by irradiation with UV or electron beams.

9. A coated substrate produced by a method as claimed in claim 8.

10. A process as claimed in claim 1, wherein A1a is selected from the group consisting of cyanurate of hexamethylene diisocyanate and cyanurate of isophorone diisocyanate, and A1b is selected from the group consisting of biuret of hexamethylene diisocyanate and biuret of isophorone diisocyanate.

11. A method of coating a substrate, which comprises applying a radiation-curable formulation as claimed in claim 6 or 7 to the substrate which is to be coated, removing any solvent and then carrying out curing by irradiation with UV or electron beams.