Fluoroalkyl silicone composition

• US 7,413,807 B2
• Filed: 04/14/2006
• Issued: 08/19/2008
• 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, Liu, Lan Hong
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US11/279,800
• Publication Number:
  US 20070254166A1
• Time in Patent Office: 858 Days
• Field of Search: 525/479, 526/279
• US Class Current: 428/447
• CPC Class Codes: C08L 2666/06 Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
• CPC Class Codes: C08L 83/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
• 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 ethylenically unsaturated groups, a crosslinking agent having at least two ethylenically unsaturated groups, and a free radical initiator.

Claims

1. A free-radically curable composition comprising:

a) a fluoroalkyl silicone having at least two ethylenically unsaturated groups,

b) greater than 80 parts by weight to 99.5 parts by weight of polyethylenically unsaturated component, based on 100 parts by weight of the fluoroalkyl silicone and the polyethylenically unsaturated component, the polyethylenically unsaturated component having at least two ethylenically unsaturated groups comprising;

(i) (meth)acrylated polyol;

(ii) surface functionalized inorganic nanoparticles, having a plurality of ethylenically unsaturated groups;

or

(iii) a combination thereof, and

c) a free radical initiator.

2. The composition of claim 1 wherein the fluoroalkyl silicone is of the formula:

3. The composition of claim 2 wherein R_f is of the formula:

C_nF_2n+1(C_mH_2mO)_dC_pH_2p—

, C_nF_2n+1CHFCF₂(C_mH_2mO)_dC_pH_2p—

or C_nF_2n+1OCHFCF₂(C_mH_2mO)_dC_pH_2p—

wherein 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.

4. The composition of claim 3 wherein n is 3 to 6.

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

6. The composition of claim 2 wherein the fluoroalkyl silicone is of the formula:

7. The composition of claim 2 wherein the fluoroalkyl silicone is of the formula:

8. The composition of claim 1 wherein said a polyethylenically unsaturated component is an organic compound of the formula R⁴(Z'"'"')_p, wherein R⁴ is an organic moiety of valency p, p is at least 2, and Z'"'"' is an ethylenically unsaturated polymerizable group, reactive with said ethylenically unsaturated group of said fluoroalkyl silicone.

9. The composition of claim 8 wherein R⁴ is a non-urethane aliphatic moiety of valency p.

10. The composition of claim 1 wherein said polyethylenically unsaturated component comprises said (meth)acrylated polyol.

11. The composition of claim 1 comprising at least 90 parts by weight of the Polyethylenically unsaturated component, based on 100 parts by weight of fluoroalkyl silicone and polyethylenically unsaturated component.

12. The composition of claim 1 wherein the free radical initiator is a UV initiator.

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

14. The composition of claim 13, wherein said inorganic nanoparticles comprise a plurality of(meth)acryloyl surface flunctional groups.

15. The composition of claim 13, wherein said inorganic nanoparticles are selected from the group of silica, zinc oxide, titania, alumina, zirconia, vanadia, chromia, iron oxide, antimony oxide, tin oxide, other colloidal metal oxides, and mixtures thereof.

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

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

18. 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 free radical initiator.

19. The method of claim 18 wherein the coating is cured by UV.

20. The method of claim 18 wherein the substrate is selected from vinyl, wood, glass, stone, metals, ceramics, masonry, paint, plastics and thermoplastic resins.

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

22. The coated substrate of claim 21, wherein the substrate is selected from vinyl, wood, glass, stone, metals, ceramics, masonry, paint, plastics and thermoplastic resins.

23. The coated substrate of claim 21 wherein the coating has an index of refraction of at least 1.6.