Curable, dual cure, one part silicone composition
Provided is a one part, dual curable composition comprising (A) a first acrylic functional polyorganosiloxane with at least one moisture curable functional group, (B) a second acrylic functional polyorganosiloxane, which may optionally contain a moisture curable functional group, and (C) a third functional polyorganosiloxane, which optionally contains an acrylic and moisture curable functional group. The combination of (A), (B), and (C) provides a composition that is both moisture curable and radiation curable and provides a material that is fast curing via the dual cure functionality and provides a cured material exhibiting a relatively low modulus, good adhesion, and optical clarity.
1. A radiation curable and moisture curable composition comprising:
(A) a first acrylic functional polyorganosiloxane with at least one moisture curable functional group;
(B) a second acrylic functional polyorganosiloxane, which may optionally contain a moisture curable functional group; and
(C) a third functional polyorganosiloxane of the formula:
where R 13 , R 14 are independently chosen from a C1-C10 alkyl; an unsaturated C1-C10 alkyl; a C1-C10 alkyl comprising one or more halogen groups; a C6-C30 aryl; and a C6-C30 substituted aryl;
R 12 is chosen from a C1-C10 alkyl; a C1-C10 alkyl comprising one or more halogen groups; a C6-C30 aryl; or a C6-C30 substituted aryl;
R 15 and R 16 are independently chosen from a C1-C3 alkyl, a alkoxyalkyl, and a siloxyalkyl;
R 17 is independently chosen from null (i.e., a bond), a C1-C10 alkyl; and a C6-C30 cycloalkyl group where the C1-C10 alkyl or C6-C30 cycloalkyl group may comprise a hydroxy group, an alkoxy group, and may have one or more heteroatoms;
R 18 is chosen from a C2-C10 unsaturated alkyl, or a (meth)acryl group, with the proviso that when R 18 is an unsaturated alkyl group, R 15 , R 16 , or both R 15 and R 16 are chosen from an alkoxyalkyl and a siloxyalkyl; and
o is zero or positive numbers.
2. The composition of claim 1 , wherein:
the first acrylic functional polyorganosiloxane (A) is of the formula:
and
the second acrylic functional polyorganosiloxane (B) is of the formula:
where R 1 , R 2 , R 3 , R 6 , R 7 , R 8 are independently chosen from a C1-C10 alkyl; an unsaturated C1-C10 alkyl; a C1-C10 alkyl comprising one or more halogen groups; a C6-C30 aryl; and a C6-C30 substituted aryl;
R 4 and R 9 are independently chosen from a C1-C10 alkylene with or without substitution or interruption by one or more heteroatoms;
R 10 is independently chosen from null (i.e., a bond); a C1-C10 alkyl; or a C6-C30 cycloalkyl group, the C1-C10 alkyl or C6-C30 alkyl group optionally comprising an —OR 19 substituent where R 19 is hydrogen or a C1-C6 alkyl;
R 5 and R 11 are independently chosen from hydrogen or a C1-C6 alkyl; and
n and m are independent of each other and are zero or positive numbers.
3. The composition of claim 2 comprising the third functional polyorganosiloxane (C) in an amount of at least 0.01 wt. % based on the total weight of the composition.
4. The composition of claim 2 comprising the third functional polyorganosiloxane (C) in an amount of from about 0.01 wt. % to about 50 wt. % based on the total weight of the composition.
5. The composition of claim 2 wherein the ratio of the first acrylic polyorganosiloxane (A) to the second acrylic functional polyorganosiloxane (B) is from about 99.95:0.05 to about 0.05:99.95.
6. The composition of claim 2 , wherein the first acrylic functional polyorganosiloxane (A) has a viscosity of from about 500 cps to about 15,000 cps; the second acrylic functional polyorganosiloxane (B) has a viscosity of from about 500 cps to about 15,000 cps; and the third acrylic functional polyorganosiloxane has a viscosity of from about 3 cps to about 1,000 cps.
7. The composition of claim 2 comprising two or more first acrylic functional polyorganosiloxanes (A).
8. The composition of claim 7 , wherein the two or more first acrylic functional polyorganosiloxanes (A) each having a different viscosity.
9. The composition of claim 1 comprising a photoinitiator component and a moisture cure catalyst.
10. The composition of claim 9 , wherein the photoinitiator is chosen from a benzophenone, a phosphine oxide, a nitroso compound, an acryl halide, a hydrazone, a hydroxy ketone, an amino ketone, a mercapto compound, a pyrillium compound, a triacrylimidazole, a benzimidazole, a chloroalkyl triazine, a benzoin ether, a benzil ketal, a benzil ester, a thioxanthone, a camphorquinone, an acetophenone derivative, or a combination of two or more thereof.
11. The composition of claim 10 wherein the photoinitiator comprises a mixture of a hydroxyketone and a phosphine oxide.
12. The composition of claim 1 comprising an adhesion promoter.
13. The composition of claim 12 , wherein the adhesion promoter is chosen from an (aminoalkyl)trialkoxysilane, an (aminoalkyl)alkyldialkoxysilane, a bis(trialkoxysilylalkyl)amine, a tris(trialkoxysilylalkyl)amine, a tris(trialkoxysilylalkyl)cyanuarate, a tris(trialkoxysilylalkyl)isocyanurate, an (epoxyalkyl)trialkoxysilane, an (epoxyalkylether)trialkoxysilane, or a combination of two or more thereof.
14. The composition of claim 1 further comprising an acryloxy resin.
15. A cured film formed from the composition of claim 1 .
16. An article comprising the cured film of claim 15 .
17. A sealing agent for an image display device comprising the composition of claim 1 .
18. An image display device comprising an image display portion and a protective portion encapsulated by the sealing agent of claim 17 .
19. A method of forming a cured film comprising curing the composition of claim 1 by (a) UV radiation, and/or (b) condensation curing.