Radiation-curable formulations

• US 6,242,101 B1
• Filed: 04/01/1999
• Issued: 06/05/2001
• Est. Priority Date: 04/02/1998
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Menzel, Klaus, Schwalm, Reinhold, Beck, Erich, Paulus, Wolfgang, Enenkel, Peter, Königer, Rainer
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US09/283,864
• Time in Patent Office: 796 Days
• Field of Search: 522/96, 522/103, 522/107, 522/182, 522/174, 522/173, 428/423.1, 428/425.8
• US Class Current: 428/425.8
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 290/06 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/14 Polymers provided for in subclass C08G
• CPC Class Codes: C08F 290/147 Polyurethanes; Polyureas
• CPC Class Codes: C08G 18/282 Alkanols, cycloalkanols or arylalkanols including terpenealcohols
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/792 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
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
• CPC Class Codes: Y10T 428/31605 Next to free metal

Abstract

Radiation-curable formulations based on ethylenically unsaturated prepolymers and difunctional esters of ethylenically unsaturated carboxylic acids with diols having a linear alkylene chain of 7 to 14 carbon atoms, a process for coating substrates using these radiation-curable formulations, and their use as automotive topcoats.

Claims

1. A radiation-curable formulation, comprising:

(i) at least one prepolymer which comprises at least two olefinic double bonds per molecule selected from the group consisting of prepolymers with urethane and/or urea groups prepared by reacting compounds having three or more isocyanate groups with α

,β

-ethylenically unsaturated compounds having at least one isocyanate-reactive group, (component A), and

(ii) at least one diester of α

,β

-ethylenically unsaturated carboxylic acids with diols having a linear alkylene chain which has 7 to 14 carbon atoms (component B).

2. A formulation as claimed in claim 1, where component B is an ester of the formula I

where R¹ independently at each occurrence is H, CH₃ or CH₂-COOX,

R² independently at each occurrence is H, CH₃ or COOX,

x is C₁-C₁₂-alkyl, and

m is an integer from 7 to 14.

3. The formulation as claimed in claim 1, wherein component A is an at least difunctional melamine (meth)acrylate.

4. A multicoat automotive finishing formulation comprising the radiation-curable formulation as claimed in claim 1.

5. A process for coating a substrate, which comprises applying a radiation-curable formulation as claimed in claim 1 to the substrate that is to be coated and then curing the applied coating by radiation with ultraviolet or electron beams.

6. A coated substrate prepared by the process as claimed in claim 5.

7. A substrate coated with the radiation-curable formulation as claimed in claim 1.

8. The substrate as claimed in claim 7, wherein said substrate is a metal or a metal having a coating thereon.

9. A hardened coating prepared by radiation curing an applied coating of the radiation-curable formulation as claimed in claim 1 applied to a substrate.

10. A radiation-curable formulation, comprising:

(i) at least one prepolymer which comprises at least two olefinic double bonds per molecule selected from the group consisting of prepolymers with urethane and/or urea groups prepared by reacting a hydroxyalkyl (meth)acrylate with a trifunctional isocyanate, (component A), and (ii) at least one diester of α

,β

-ethylenically unsaturated carboxylic acids with diols having a linear alkylene chain which has 7 to 14 carbon atoms (component B).

11. A formulation as claimed in claim 10, where the trifunctional isocyanate is selected from isocyanurates and biurets of difunctional isocyanates.