Composition containing fluoroalkyl hydrosilicone

• US 7,410,704 B2
• Filed: 04/14/2006
• Issued: 08/12/2008
• Est. Priority Date: 04/14/2006
• Status: Expired due to Fees

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Qiu, Zai-Ming, Walker, Christopher B. Jr., Liu, Lan Hong
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US11/279,813
• Publication Number:
  US 20070254168A1
• Time in Patent Office: 851 Days
• Field of Search: 528/40, 428/443, 428/447
• US Class Current: 428/447
• CPC Class Codes: C08F 214/18 Monomers containing fluorine
• CPC Class Codes: C08F 222/104 of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• 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: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Described is a free-radically curable composition comprising a fluoroalkyl silicone having at least two hydride groups, a polyethylenically unsaturated component having at least two ethylenically unsaturated groups, a hydrosilylation catalyst, and a free radical initiator.

Claims

1. A curable composition comprising:

a) a polyethylenically unsaturated component having at least two ethylenically unsaturated groups,

b) a fluoroalkyl hydrosilicone having at least two Si-H groups,

c) a hydrosilylation catalyst, and

d) a free radical polymerization catalyst,

wherein the polyethylenically unsaturated component having at least two ethylenically unsaturated groups is present in an amount sufficient such that the molar equivalence of the ethylenically unsaturated groups is in excess of the molar equivalence of Si-H groups of the fluoroalkyl hydrosilicone, and the composition comprising 80 parts by weight to about 99.5 parts by weight of the polyethylenically unsaturated component based on 100 parts by weight of the polyethylenically unsaturated component and the fluoroalkyl hydrosilicone.

2. The composition of claim 1 wherein said polyethylenically unsaturated component is of the formula

R⁴(Z'"'"')_p, wherein R⁴ is an non-urethane organic moiety of valency p, p is at least 2, and Z'"'"' is an ethylenically unsaturated polymerizable group.

3. The composition of claim 2 wherein Z'"'"' is selected from alkenyl groups, alkynyl groups, vinyloxyalkylene, allyloxyalkylene, and (meth)acryloyl groups.

4. The composition of claim 2 wherein R⁴ is an aliphatic moiety of valency p.

5. The composition of claim 1 wherein said polyethylenically unsaturated component is an acrylated polyol.

6. The composition of claim 1 wherein said fluoroalkyl hydrosilicone is of the formula:

7. The composition of claim 6 wherein R_f is of the formulas C_nF_2n+1(CH₂O)_dC_mH_2m—

, or C_nF_2n+1CHXCF₂(C_mH_2mO)_dC_{p H2p}—

or C_nF_2n+OCHXCF₂(C_mH_2mO)_dC_pH_2p—

where X is H or F, n is an integer of 1 to 12, m is an integer of 1 to 12, d is 0 or 1, and p is an integer of 2 to 12.

8. The composition of claim 1 wherein said a polyethylenically unsaturated component comprises surface functionalized inorganic nanoparticles, having a plurality of ethylenically unsaturated groups.

9. The composition of claim 8, wherein said inorganic nanoparticles comprise a plurality of (meth)acryloyl surface functional groups.

10. The composition of claim 1, further comprising a mono (meth)acryloyl compound having a functional group.

11. The composition of claim 1, wherein said hydrosilylation catalyst is a photohydrosilylation catalyst.

12. The composition of claim 1 comprising the hydrosilylation reaction product of

a) a polyethylenically unsaturated component having at least two ethylenically unsaturated groups, and

b) a fluoroalkyl hydrosilicone having at least two Si-H groups.

13. The composition of claim 1 wherein said polyethylenically unsaturated component comprises surface modified zirconia nanoparticles.

14. A method of providing a coating onto a substrate comprising the steps of:

a) coating a substrate with the composition of claim 1 and curing the coating with a hydrosilylation catalyst and a free radical catalyst.

15. The method of claim 14 wherein the coating is cured by UV.

16. The method of claim 14 wherein the substrate is selected from vinyl, wood, glass, stone, metals, ceramics, masonry, paint, plastics and thermoplastic resins.

17. A coated substrate comprising the cured composition of claim 1.

18. The coated substrate of claim 17, wherein the substrate is selected from vinyl, wood, glass, stone, metals, ceramics, masonry, paint, plastics end thermoplastic resins.

19. The coated substrate of claim 17 wherein said coating has an index of refraction of at least 1.6.