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

Patent metadata

Field	Value
Publication number	US-9884969-B2
Application number	US-201314020419-A
Country	US
Kind code	B2
Filing date	Sep 6, 2013
Priority date	May 25, 2012
Publication date	Feb 6, 2018
Grant date	Feb 6, 2018

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.

First claim

What is claimed is:

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:

wherein, in Chemical Formula 1, m is an integer of from 2 to 11, and n is an integer of from 1 to 20.

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:

wherein, in Chemical Formula 2, R 1 is hydrogen or a methyl, and R 2 is a C1-12 linear or branched alkylene group, a C4-20 cycloalkylene group, or a C6-20 arylene group.

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 .

Assignees

• Lg Chemical Ltd

Inventors

• Kim Heon
• Chang Yeong Rae
• Kim Hye Min

Classifications

• C08F220/343

  in the form of urethane links · CPC title

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• C08B37/0012

  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 title

• C08G63/08

  Lactones or lactides · CPC title