UV-curable coating compositions with self-healing capabilities, coating films, and methods of producing coating films

• US 8,975,308 B2
• Filed: 02/13/2012
• Issued: 03/10/2015
• Est. Priority Date: 02/14/2011
• Status: Active Grant

• Current Assignee: LG Chem Limited (LG Corporation)
• Original Assignee: LG Chem Limited (LG Corporation)
• Inventors: Kim, Hye-Min, Chang, Yeong-Rae, Kim, Heon
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WHITELEY, JESSICA
• Application Number:
  US13/990,698
• Publication Number:
  US 20130261209A1
• Time in Patent Office: 1,121 Days
• Field of Search: 522/33, 522/6, 522/1, 522/71, 522/189, 522/184, 520/1
• US Class Current: 522/33
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 18/6725 containing ester groups other than acrylate or alkylacrylate ester groups
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/7621 being toluene diisocyanate including isomer mixtures
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08K 2003/023 Silicon
• CPC Class Codes: C08K 9/04 Ingredients treated with organic substances treated with macromolecular compounds C08K9/08
• CPC Class Codes: C09D 175/14 Polyurethanes having carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 7/62 modified by treatment with other compounds

Abstract

The present invention is directed to a coating composition including a (meth)acrylate binder resin, a UV initiator, an organic solvent, and silica particles surface-treated with a (meth)acrylate compound, a coating film including a cured product of the coating composition, and a method of producing the coating film. The present invention makes it possible to provide a coating material having high transmittance and a low level of haze, and excellent scratch resistance and self-healing capabilities.

Claims

1. A coating composition comprising a (meth)acrylate binder resin, a UV initiator, an organic solvent, and silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage,

wherein the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage comprise a compound of Chemical Formula 2:

2. The coating composition in accordance with claim 1, wherein the (meth)acrylate binder resin comprises at least one polymer resin selected from the group consisting of a urethane (meth)acrylate resin and a hydroxyalkyl (meth)acrylate resin modified with a polylactone compound.

3. The coating composition in accordance with claim 2, wherein the hydroxyalkyl (meth)acrylate resin modified with a polylactone compound comprises a compound of Chemical Formula 1:

4. The coating composition in accordance with claim 2, wherein the urethane (meth)acrylate resin comprises a reaction product between an organic isocyanate compound having at least two isocyanate groups per molecule and a hydroxyalkyl (meth)acrylate modified with a polylactone compound.

5. The coating composition in accordance with claim 1, comprising:

20% to 80% by weight of the (meth)acrylate binder resin;

1% to 10% by weight of the UV initiator;

5% to 50% by weight of the organic solvent; and

1% to 30% by weight of the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage.

6. The coating composition in accordance with claim 1, further comprising a UV-curable monomer.

7. The coating composition in accordance with claim 6, wherein the UV-curable monomer comprises at least one multifunctional acrylate compound selected from the group consisting of pentaerythritol tri/tetraacrylate (PETA), dipentaerythritol hexa-acrylate (DPHA), trimethylol propane triacrylate (TMPTA), and hexamethylene diacrylate (HDDA).

8. The coating composition in accordance with claim 1, further comprising at least one additive selected from the group consisting of a leveling agent and a dispersion stabilizer.

9. A coating film comprising a cured product of a coating composition of claim 1.

10. The coating film in accordance with claim 9, wherein the (meth)acrylate binder resin and the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage are chemically bonded.

11. The coating film in accordance with claim 9, wherein the (meth)acrylate binder resin and the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage form a crosslinked network structure.

12. The coating film in accordance with claim 9, further comprising a UV-curable monomer.

13. A method of producing a coating film, which comprises the steps of:

mixing a (meth)acrylate binder resin, a UV initiator, an organic solvent, and a silica particle having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage;

applying the mixture on a substrate and drying it; and

subjecting the dried mixture to UV curing,

wherein the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage comprise a compound of Chemical Formula 2;

14. The method of producing a coating film in accordance with claim 13, further comprising a step of preparing the (meth)acrylate binder resin.

15. The method of producing a coating film in accordance with claim 14, wherein the step of preparing the (meth)acrylate binder resin comprises triggering a reaction between an organic isocyanate compound having at least two isocyanate groups per molecule and a polylactone-modified hydroxyalkyl (meth)acrylate resin to produce a urethane (meth)acrylate resin.

16. The method of producing a coating film in accordance with claim 13, further comprising a step of preparing the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage.

17. The method of producing a coating film in accordance with claim 16, wherein the step of preparing the silica particles having a polylactone-modified hydroxyalkyl (meth)acrylate linked to their surface through a urethane linkage comprises subjecting silica particles to a reaction with a diisocyanate compound, and subjecting a product resulting from the reaction between the silica particles and the diisocyanate compound to a reaction with a (meth)acrylate compound.

18. The method of producing a coating film in accordance with claim 13, further comprising a step of adding a UV-curable monomer to the mixture.

19. The method of producing a coating film in accordance with claim 13, further comprising a step of adding at least one additive selected from the group consisting of a leveling agent and a dispersion stabilizer to the mixture.