Poly-rotaxane compound, photocurable coating composition, and coating film

• US 9,884,969 B2
• Filed: 09/06/2013
• Issued: 02/06/2018
• Est. Priority Date: 05/25/2012
• Status: Active Grant

• Current Assignee: LG Chem Limited (LG Corporation)
• Original Assignee: LG Chem Limited (LG Corporation)
• Inventors: Kim, Heon, Chang, Yeong-Rae, Kim, Hye-Min
• Primary Examiner(s): Pepitone, Michael
• Assistant Examiner(s): ROSWELL, JESSICA MARIE
• Application Number:
  US14/020,419
• Publication Number:
  US 20140080936A1
• Time in Patent Office: 1,614 Days
• Field of Search: 522 8, 522 88, 524 48
• CPC Class Codes: C08B 37/0012 Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
• CPC Class Codes: C08B 37/0015 Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
• CPC Class Codes: C08F 220/343 in the form of urethane links
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 83/007 Polyrotaxanes; Polycatenanes
• CPC Class Codes: C08J 2367/02 Polyesters derived from dicarboxylic acids and dihydroxy compounds; C08J2367/06 takes precedence
• CPC Class Codes: C08J 2400/21 Polyrotaxanes; Polycatenanes
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08L 101/005 Dendritic macromolecules
• CPC Class Codes: C08L 5/16 Cyclodextrin; Derivatives thereof
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C09D 105/16 Cyclodextrin; Derivatives thereof
• 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: C09D 7/63 organic
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence
• CPC Class Codes: G03F 7/031 Organic compounds not covered by group G03F7/029
• CPC Class Codes: G03F 7/032 with binders
• CPC Class Codes: G03F 7/033 the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
• CPC Class Codes: G03F 7/035 the binders being polyurethanes
• CPC Class Codes: G03F 7/0757 : Macromolecular compounds containing Si-O, Si-C or Si-N bonds G03F7/0752 takes precedence

Abstract

The present invention relates to a novel polyrotaxane compound having a specific chemical structure, a photocurable coating composition that may provide a coating material having excellent mechanical properties such as scratch resistance, chemical resistance, abrasion resistance, and the like, and excellent self-healing capability, and a coating film obtained from the photocurable coating composition.

Claims

1. A polyrotaxane compound comprising:

a macrocycle to which a lactone-based compound is bonded;

a linear molecule penetrating the macrocycle; and

blocking groups arranged at both ends of the linear molecule and preventing the macrocycle from escaping,

wherein a final substitution rate at the end of the lactone-based compound bonded to the macrocycle of the polyrotaxane compound is 40 mol % to 70 mol %.

2. The polyrotaxane compound according to claim 1,

wherein the final substitution rate at the end of the lactone-based compound bonded to the macrocycle of the polyrotaxane compound is 45 mol % to 65 mol %.

3. The polyrotaxane compound according to claim 1, wherein the macrocycle includes at least one selected from the group consisting of α

-cyclodextrin, β

-cyclodextrin, and γ

-cyclodextrin.

4. The polyrotaxane compound according to claim 1, wherein the lactone-based compound is bonded to the macrocycle by a direct bond or a C1-10 linear or branched oxyalkylene group.

5. The polyrotaxane compound according to claim 1, wherein a residue of the lactone-based compound includes a functional group of the following Chemical Formula 1:

6. The polyrotaxane compound according to claim 1,

wherein a (meth)acrylate-based compound is substituted to the end of the lactone-based compound through a direct bond, a urethane bond, an ether bond, a thioester bond, or an ester bond.

7. The polyrotaxane compound according to claim 6,

wherein the (meth)acrylate-based compound includes a functional group of the following Chemical Formula 2:

8. The polyrotaxane compound according to claim 1, wherein the linear molecule is a polyoxyalkylene-based compound or a polylactone-based compound.

9. The polyrotaxane compound according to claim 1, wherein the linear molecule has a weight average molecular weight of 1000 to 50,000.

10. The polyrotaxane compound according to claim 1, wherein the blocking group includes at least one functional group selected from the group consisting of dinitrophenyl, cyclodextrin, adamantane, trityl, fluorescein, and pyrene groups.

11. The polyrotaxane compound according to claim 1, wherein the polyrotaxane compound has a weight average molecular weight of 100,000 to 800,000.

12. A photocurable coating composition comprising:

the polyrotaxane compound of claim 1;

a polymer resin or a precursor thereof; and

a photoinitiator.

13. The photocurable coating composition according to claim 12,

wherein the final substitution rate at the end of the lactone-based compound bonded to the macrocycle of the polyrotaxane compound is 45 mol % to 65 mol %.

14. The photocurable coating composition according to claim 12, wherein the polymer resin is selected from the group consisting of a polysiloxane-based resin, a (meth)acrylate-based resin, and a urethane(meth)acrylate-based resin, a mixture thereof, and a copolymer thereof.

15. The photocurable coating composition according to claim 12, wherein the precursor of the polymer resin includes monomers or oligomers including at least one functional group selected from the group consisting of (meth)acrylate, vinyl, siloxane, epoxy, and urethane groups.

16. The photocurable coating composition according to claim 12, wherein the photoinitiator includes at least one compound selected from the group consisting of an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound.

17. The photocurable coating composition according to claim 12, comprising:

1 to 95 wt % of the polyrotaxane compound;

1 to 95 wt % of the polymer resin or a precursor thereof; and

0.01 to 10 wt % of the photoinitiator.

18. The photocurable coating composition according to claim 12, further comprising an organic solvent.

19. A coating film comprising a photocured product of the photocurable coating composition of claim 12.