IP Library Granted Patent US 10,822,504
Granted Patent B2
US 10,822,504 · App. 14/915,840 · Granted Nov 3, 2020

Self-healing transparent polymer compositions containing conductive colloids

Inventor: Haipeng Zheng (Dallas, TX)
Assignee: ESSILOR INTERNATIONAL
C09D7/61C08G75/04C08G75/12C09D4/00C09D5/00C09D181/02G02B1/041G02B1/105G02B1/14G02C7/02C08G18/835C08K3/22C08K3/2279G02C2202/16
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Quick Facts
Patent No.
US 10,822,504
App. No.
14/915,840
Granted
Nov 3, 2020
Kind
B2
Abstract

Described is a thiol-ene composition that includes a resinous mixture of at least a first monomer and at least a second monomer, in which the first monomer is a polyfunctional allyl monomer and the second monomer is a polyfunctional thiol and the molar ratio of the first monomer to the second monomer is about 60:40 to about 80:20. Said composition further includes conductive colloidal particles in an amount between about 4 wt % and about 7 wt % of the total composition. When cured, a formed composition offers self-healing properties and resistance to abrasions and scratches that exceed the levels found in comparative thiol-enes that either lack the addition of the conductive colloidal particles and/or have a less effective ratio of first monomer to second monomer.

Claims (31)

1. A composition comprising:

a thiol-ene network formed by a thiol-ene reaction with at least a first monomer and at least a second monomer in a resinous mixture, wherein the first monomer is a polyfunctional allyl monomer and the second monomer is a polyfunctional thiol, wherein a molar ratio of the first monomer to the second monomer in the resinous mixture is about 65:35 to about 73:27; and

conductive colloidal particles in an amount between about 5 wt % and about 7 wt % of the thiol-ene network, wherein the conductive colloidal particles are dispersed uniformly within the thiol-ene network, forming a transparent matrix that has a glass transition temperature from about 40° C. to about 100° C.;

wherein the composition is a thin transparent film coating on an ophthalmic lens having a thickness in a range from about 2 μm to about 50 μm; and

wherein the conductive colloidal particles are selected from the group consisting of Sb 2 O 3 , P 2 O 5 , and a combination thereof.

2. The composition of claim 1 , wherein the composition is a shape memory composition.

3. The composition of claim 1 , wherein the molar ratio of the first monomer to the second monomer in the resinous mixture is about 69:31 to about 73:27.

4. The composition of claim 1 , wherein the polyfunctional allyl monomer is 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TTT) and the polyfunctional thiol is pentaerythritol tetrakis(3-mercapto propionate) (PTMP).

5. An optical article comprising:

a transparent substrate; and

at least one transparent composition on a facing surface of the transparent substrate, wherein the transparent composition is formed by curing a resinous mixture comprising at least a polyfunctional allyl monomer and a polyfunctional thiol together with conductive colloidal particles in an amount between about 5 wt % and about 7 wt % of the transparent composition in which a molar ratio of the polyfunctional allyl monomer to the polyfunctional thiol is about 65:35 to about 73:27, and

wherein the at least one transparent composition has a thickness in a range from about 2 μm to about 50 μm, is self-healing by at least partially or completely sealing its outer surface when subject to abrasion, and wherein the at least one transparent composition has a healing level of greater than 65% and a Haze hm , of <0.58%; and

wherein the conductive colloidal particles are selected from the group consisting of Sb 2 O 3 , P 2 O 5 , and a combination thereof.

6. The optical article of claim 5 , wherein the polyfunctional allyl monomer is a triallyl monomer comprising one or more of triallyl triazine, triallyl cyanurate, triallyl isocyanurate, triallyl ether, and variations thereof.

7. The optical article of claim 5 , wherein the amount of the first monomer is about 40 wt % to about 75 wt % of the resinous mixture.

8. The optical article of claim 5 , wherein the polyfunctional thiol is one or more of a modified trithiol, modified tetrathiol and variations thereof.

9. The optical article of claim 5 , wherein the polyfunctional allyl monomer is a triallyl monomer comprising one or more of triallyl, wherein the resinous mixture is at least about 70% or greater of the composition based on the weight of the total composition.

10. The optical article of claim 5 , wherein the polyfunctional allyl monomer is a triallyl monomer comprising one or more of triallyl, wherein the composition further comprises a solvent in an amount up to about 30% of the composition based on the weight of the composition.

11. The optical article of claim 5 , wherein the polyfunctional allyl monomer is a triallyl monomer comprising one or more of triallyl, wherein the composition is applied in a liquid form to a substrate.

12. The optical article of claim 5 , wherein the polyfunctional allyl monomer is a triallyl monomer comprising one or more of triallyl, wherein the composition is cured by one or more of heat and light.

13. The optical article of claim 5 , wherein the molar ratio of the first monomer to the second monomer in the resinous mixture is about 69:31 to about 73:27.

14. The optical article of claim 5 , wherein the polyfunctional allyl monomer is 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TTT) and the polyfunctional thiol is pentaerythritol tetrakis(3-mercapto propionate) (PTMP).

15. The optical article of claim 5 , wherein the at least one transparent composition has a Haze hw of <0.4%.

16. An optical article comprising:

a transparent substrate; and

at least one transparent composition on a facing surface of the transparent substrate, wherein:

the transparent composition is formed by curing a resinous mixture comprising at least a polyfunctional allyl monomer and a polyfunctional thiol together with conductive colloidal particles selected from the group consisting of Sb 2 O 3 , P 2 O 5 , and a combination thereof, in an amount between about 5 wt % and about 7 wt % of the transparent composition in which a molar ratio of the polyfunctional allyl monomer to the polyfunctional thiol is about 65:35 to about 73:27;

the at least one transparent composition has a thickness in a range from about 2 μm to about 50 μm, is self-healing by at least partially or completely sealing its outer surface when subject to abrasion, and wherein the at least one transparent composition has a healing level of greater than 65% and a Hazehw of <0.58%; and

the polyfunctional allyl monomer is 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (TTT) and the polyfunctional thiol is pentaerythritol tetrakis( 3 -mercapto propionate) (PTMP).

17. The optical article of claim 16 , wherein the molar ratio of the first monomer to the second monomer in the resinous mixture is about 69:31 to about 73:27.

18. The optical article of claim 16 , wherein the at least one transparent composition has a Haze hw of <0.4%.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2018
From: ESSILOR INTERNATIONAL (COMPAGNIE GÉNÉRALE D'OPTIQUE)
To: ESSILOR INTERNATIONAL
Reel/Frame 045853/0275 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2016
From: ZHENG, HAIPENG
To: ESSILOR INTERNATIONAL (COMPAGNIE GENERALE D'OPTIQUE)
Reel/Frame 038194/0085 →