IP Library Granted Patent US 9,453,944
Granted Patent B2
US 9,453,944 · App. 14/492,530 · Granted Sep 27, 2016

Polymerizable amido-containing organosilicon compounds, silicon-containing polymers and biomedical devices therefrom

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Quick Facts
Patent No.
US 9,453,944
App. No.
14/492,530
Granted
Sep 27, 2016
Kind
B2
Abstract

There is provided a fast curing composition comprising an alpha, beta-unsaturated amido-containing organosilicon compound, useful in making water absorbing silicone-hydrogel films for biomedical devices, such as contact lens, and a process for producing these monomers. This invention also provides for hydrogels made from the alpha, beta-unsaturated amido-containing organosilicon compound described herein.

Claims (102)

1. A composition for forming a hydrogel comprising an alpha, beta-unsaturated amido-containing organosilicon compounds having the structure of Formula (I):

wherein:

R 1 , R 2 , and R 3 are independently chosen from hydrogen, an alkyl group containing from 1 to 3 carbon atoms, a phenyl group, or R 7 C(═O)OR 8 , wherein R 7 is a chemical bond or an alkylene group containing from 1 to 6 carbon atoms, and R 8 is hydrogen or an alkyl group of from 1 to 3 carbon atoms;

R 4 is hydrogen, an alkyl group containing from 1 to 6 carbon atoms, or a phenyl group;

R 5 is an alkylene, containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

A is oxygen or sulfur;

G is a hydroxyl-substituted cycloalkylene group;

R 6 is a chemical bond or an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

X 1 is a methyl, trimethylsiloxy, or —O[Si(CH 3 ) 2 O—] n , wherein n is an integer of from 1 to 9;

X 2 is methyl, trimethylsiloxy or

—[OSi(CH 3 ) 2 ] m G 1 , wherein G 1 is (CH 3 ) 3 SiO— or H(CH 3 ) 2 SiO—, or an alpha, beta-unsaturated amido-containing group with the general formula:

and m is an integer from 0 to 200, with the proviso that when X 2 is —[OSi(CH 3 ) 2 ] m G 1 , then X 1 and X 3 is methyl;

X 3 is methyl, trimethylsiloxy, (CH 3 ) 3 SiCH 2 CH 2 —, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O—, or

—OSi(CH 3 ) 2 , with the provisos that (i) when X 1 is —O[Si(CH 3 ) 2 O—] n , then X 3 is

—OSi(CH 3 ) 2 and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, (ii) when X 3 is

—OSi(CH 3 ) 2 , then X 1 is —O[Si(CH 3 ) 2 O—] n and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring.

2. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein R 1 and R 2 is hydrogen, R 3 is hydrogen or methyl, R 4 is hydrogen or methyl, A is oxygen, and R 6 is independently chosen from a chemical bond, methylene, 1,2-ethylene, 1,3-propylene, 1,2-propylene, 1,3-butylene, and 1,4-butylene.

3. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein R 1 is R 7 C(═O)OR 8 , wherein R 7 is a chemical bond, and R 8 is an alkyl group of from 1 to 3 carbon atoms.

4. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein X 1 is methyl or trimethylsiloxy; X 2 is methyl or trimethylsiloxy; and X 3 is trimethylsiloxy, dimethyl-(2-trimethylsilanyl-ethyl)-silanyl, or dimethyl-(2-trimethylsilanyl-ethyl)-silanyloxy.

5. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein X 1 is methyl or trimethylsiloxy; X 2 is methyl; and X 3 is trimethylsiloxy or dimethyl-(2-trimethylsilanyl-ethyl)-silanyloxy.

6. The composition of claim 1 , wherein the alpha, beta-unsaturated amido-containing organosilicon compound is chosen from (acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-bis-(trimethylsiloxy)methylsilanyl-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-bis-(trimethylsiloxy)methylsilanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[bis-(3-trimethylsiloxy)methylsilanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4,6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4,6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester, (2-methyl-acryloylamino)-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5, 7,2, 4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-2-hydroxy-cyclohexyl ester, acryloylamino-acetic acid 4-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[tris-(trimethylsiloxy)silanyl]-2-hydroxy-cyclohexyl ester, or a combination of two or more thereof.

7. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein G is a cycloalkylene group, and the alpha, beta-unsaturated amido-containing organosilicon compound has the stereochemistry in which the alpha, beta-unsaturated amido group

and the silyl group, —R 6 SiX 1 X 2 X 3 , are substituted in the 1,3-position on the cycloalkylene linking group.

8. The composition of claim 7 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein the alpha, beta-unsaturated amido-containing compounds is chosen from acryloylamino-acetic acid 2-hydroxy-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[tris-(2-trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[tris-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1, 3, 5, 7,2, 4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester, or a combination of two or more thereof.

9. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein the alpha, beta-unsaturated amido-containing organosilicon compound has the stereochemistry in which the alpha, beta-unsaturated amido group and the silyl group is in a trans-1,3-substitution on the cycloalkylene linking group and having the stereochemistry of Formula (II):

wherein:

R 1 , R 2 , and R 3 are independently chosen from hydrogen, an alkyl group containing from 1 to 3 carbon atoms, a phenyl group, or R 7 C(═O)OR 8 , wherein R 7 is a chemical bond or an alkylene group containing from 1 to 6 carbon atoms, and R 8 is hydrogen or an alkyl group of from 1 to 3 carbon atoms;

R 4 is hydrogen, an alkyl group containing from 1 to 6 carbon atoms, or a phenyl group;

R 5 is an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

R 6 is a chemical bond or an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

X 1 is a methyl, trimethylsiloxy, or —O[Si(CH 3 ) 2 O—] n , wherein n is an integer of from 1 to 9;

X 2 is methyl, or trimethylsiloxy;

X 3 is methyl, trimethylsiloxy, (CH 3 ) 3 SiCH 2 CH 2 —, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O—, or

—OSi(CH 3 ) 2 , with the provisos that (i) when X 1 is —O[Si(CH 3 ) 2 O—] n , then X 3 is

—OSi(CH 3 ) 2 and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, (ii) when X 3 is

—OSi(CH 3 ) 2 , then X 1 is —O[Si(CH 3 ) 2 O—] n and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring.

10. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), wherein alpha, beta-unsaturated amido-containing organosilicon compound also has the general Formula (III):

wherein:

R 1 , R 2 , or R 3 are independently chosen from hydrogen, an alkyl group containing from 1 to 3 carbon atoms, a phenyl group, or

R 7 C(═O)OR 8 , wherein R 7 is a chemical bond or an alkylene group containing from 1 to 6 carbon atoms and R 8 is hydrogen or an alkyl group of from 1 to 3 carbon atoms;

R 4 is hydrogen or an alkyl group containing from 1 to 6 carbon atoms or phenyl;

R 5 is an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

A is oxygen, nitrogen or sulfur;

G is a hydroxyl-substituted cyclohexylene group;

R 6 is a chemical bond or an alkylene group containing from 1 to 16 carbon atoms.

11. The composition of claim 9 , wherein the alpha, beta-unsaturated amido-containing organosilicon compound is chosen from acryloylamino-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[tris-(2-trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[tris-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid trans-2-hydroxy-trans-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; and (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[μmethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid trans-2-hydroxy-trans-5-[2-(2,4,4,6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; or a combination of two or more thereof.

12. The composition of claim 1 , wherein, the composition cures to self-standing film in 10 seconds or less using 365 nm light with an intensity of 105 mW/cm 2 .

13. The composition of claim 1 , wherein the alpha, beta unsaturated amido-containing organosilicon compound comprises the structure of Formula (I), comprising:

(a) a reaction of an oxa-bicyclo[4.1.0]heptene or alkenyl-oxa-bicyclo[4.1.0]heptane having the Formula (IV):

with a hydridosilyl-containing organic compound of Formula (V):

H—SiX 1 X 2 X 3   (V)

wherein:

R 7 is a chemical bond or an alkylene group containing from 1 to 14 carbon atoms an optionally a heteroatom of oxygen, sulfur or nitrogen; and

R 8 is hydrogen or an alkyl group of from 1 to 6 carbon atoms,

X 1 is a methyl, trimethylsiloxy, or —O[Si(CH 3 ) 2 O—] n , wherein n is an integer of from 1 to 9;

X 2 is methyl, trimethylsiloxy, or —[OSi(CH 3 ) 2 ] m G 2 , wherein G 2 is (CH 3 ) 3 SiOSi(CH 3 ) 2 O— or H(CH 3 ) 2 SiO—; and m is an integer from 0 to 200, with the proviso that when X 2 is —[OSi(CH 3 ) 2 ] m G 2 , then X 1 and X 3 is methyl;

X 3 is methyl, trimethylsiloxy, (CH 3 ) 3 SiCH 2 CH 2 —, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O— or

—OSi(CH 3 ) 2 , with the provisos that (i) when X 1 is —O[Si(CH 3 ) 2 O—] n , then X 3 is

—OSi(CH 3 ) 2 and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, (ii) when X 3 is

—OSi(CH 3 ) 2 , then X 1 is —O[Si(CH 3 ) 2 O—] n and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, and in the presence of a hydrosilylation catalyst; and

(b) a reaction of the product of step (a) with an alpha, beta-unsaturated amido-containing acid having the Formula (VI):

wherein:

R 1 , R 2 , or R 3 are independently chosen from hydrogen, an alkyl group containing from 1 to 3 carbon atoms, a phenyl group, or R 7 C(═O)OR 8 , wherein R 7 is a chemical bond or an alkylene group containing from 1 to 6 carbon atoms, and R 8 is hydrogen or an alkyl group of from 1 to 3 carbon atoms;

R 4 is hydrogen, or an alkyl group containing from 1 to 6 carbon atoms, or a phenyl group;

R 5 is an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen or a combination of two or more thereof; and

A is oxygen or sulfur, the reaction in (b) optionally being carried out in the presence of an addition catalyst, to open the oxirane ring and provide for polymerizable amido-containing organosilicon compounds.

14. The composition of claim 13 , wherein the alkenyl-oxa-bicyclo[4.1.0]heptane comprises greater than 85 weight percent of 3-ethenyl-7-oxa-bicyclo[4.1.0]heptane, which has the oxygen atom of the oxirane ring bonded to the 1 and 6-carbon atoms of the cyclohexyl group in the C-1 equatorial and C-6 axial positions and has a vinyl group bonded to the 3-carbon atom of the cyclohexyl ring in the equatorial position, based upon the total weight of the 3-ethenyl-oxa-bicyclo[4.1.0]heptane, or is greater than 85 weight percent 2-ethenyl-7-oxa-bicyclo[4.1.0]heptane, which has the oxygen atom of the oxirane ring bonded to the 1 and 6-carbon atoms of the cyclohexyl group in the C-1 axial and C-6 equatorial positions and has the vinyl group bonded to the 2-carbon atom of the cyclohexyl ring in the equatorial position, based upon the total weight of the ethenyl-oxa-bicyclo[4.1.0]heptane.

15. The composition of claim 13 , wherein the hydridosilyl-containing organic compounds are chosen from 1,1,1,2,3,3,3-heptamethyl-trisiloxane; tris-(trimethylsiloxy)hydridosilane; 1-dimethylsilanyl-2-trimethylsilanyl-ethane; 1,1,3,3-tetramethyl-1-(2-trimethylsilanyl-ethyl)-disiloxane; and 2,2,4,4,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinane, or a combination of two or more thereof.

16. The composition of claim 13 , wherein the hydrosilylation catalyst is chosen from platinum, palladium, ruthenium, iridium and rhodium, metal complexes of platinum, palladium, ruthenium, iridium, rhodium, or a combination of two or more thereof.

17. The composition of claim 13 , wherein the hydrosilylation catalyst described in claim 13 is chosen from chloroplatinic acid dissolved in ethanol, chloroplatinic acid dissolved in isopropanol, chloroplatinic acid dissolved in octanol, platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex dissolved in xylene and platinum(0)-1, 3-divinyl-1,1,3,3-tetramethyldisiloxane complex dissolved in polydimethylsiloxane oils, or a combination of two or more thereof.

18. The composition of claim 13 , wherein the alpha-beta unsaturated amido-containing acid is chosen from the acryloylamino-acetic acid; (2-methyl-acryloylamino)-acetic acid; 3-(2-methyl-acryloylamino)-propionic acid; 3-[methyl-(2-methyl-acryloyl)-amino]-propionic acid; 3-(carboxymethyl-carbamoyl)-acrylic acid methyl ester, 3-(thiocarboxymethyl-carbamoyl)-acrylic acid methyl ester; acryloylamino-thioacetic acid; and (2-methyl-acryloylamino)-thioacetic acid; or a combination of two or more thereof.

19. The composition of claim 13 , wherein alpha, beta unsaturated amido-containing organosilicon compound is chosen from (acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-bis-(trimethylsiloxy)methylsilanyl-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-bis-(trimethylsiloxy)methylsilanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[bis-(3-trimethylsiloxy)methylsilanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4, 6, 6-pentamethyl-[1,3,5,2,4, 6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4, 6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester, (2-methyl-acryloylamino)-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5, 7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-2-hydroxy-cyclohexyl ester, acryloylamino-acetic acid 4-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl]-2-hydroxy-cyclohexyl ester; and acryloylamino-acetic acid 4-[tris-(trimethylsiloxy)silanyl]-2-hydroxy-cyclohexyl ester, or a combination of two or more thereof.

20. The composition of claim 13 , wherein the alpha, beta-unsaturated amido-containing organosilicon compound is chosen from acryloylamino-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[tris-(2-trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[tris-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid trans-2-hydroxy-trans-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; and (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; and acryloylamino-acetic acid trans-2-hydroxy-trans-5-[2-(2,4,4,6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester or a combination of two or more thereof.

21. The composition of claim 13 , wherein the addition catalyst of step (b) is a titanium tetraalkoxide.

22. The composition of claim 1 , wherein the composition further comprises at least one co-monomer containing an activated carbon-carbon double bond chosen from methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl acrylate, cyclohexyl methacrylate, methyl acrylate, 2-hydroxyethyl methacrylate (HEMA), N-vinylpyrrolidone (NVP), methacrylic acid (MA), dimethylacrylamide (DMA), and mixtures of two or more thereof.

23. The composition of claim 1 , wherein the composition further comprises at least one co-monomer selected from N-vinyl-pyrrolidone; N-vinyl-caprolactam; N-vinyl-acetamide; N-vinyl-formamide; N-vinyl-isopropylamide; vinyl benzene; vinyl naphthalene; vinyl pyridine; vinyl alcohol; vinyl containing silicones, and combinations of two or more thereof.

24. The composition of claim 1 , wherein the composition further comprises at least one co-monomer selected from 3-[tris(trimethylsiloxy)silyl]propyl methacrylate; methyl-di(trimethylsiloxy)-silyl propyl glycerol methacrylate; 3-(trimethylsilyl)propyl vinyl carbonate; 3-(vinyloxycarbonylthio)propyl-[tris(trimethylsiloxy)silane]; 3-[tris(tri-methylsiloxy)silyl]propyl vinyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl allyl carbamate; 3-[tris(trimethylsiloxy)silyl]propyl vinyl carbonate, or a combination of two or more thereof.

25. The composition of claim 1 , wherein the composition further comprises at least one crosslinker chosen from ethylene glycol diacrylate, ethylene glycol dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, 1,4-butylene glycol dimethacrylate, ethylene glycol dicrotonate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, dipropylene glycol dimethacrylate, dipropylene glycol diacrylate, trimethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol dicrotonate, tetraethylene glycol dimethacrylate, hexaethylene glycol dimethacrylate, tripropylene glycol diacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, tributylene glycol dimethacrylate, tetrabutylene glycol dimethacrylate, hexamethylene glycol dimethacrylate, octamethylene glycol dimethacrylate, decamethylene glycol dimethacrylate, allyl methacrylate, divinylbenzene, diallyl phthalate, trimethylolpropane trimethacrylate, diallyl tartrate, diallyl maleate, triallylmelamine, N,N′-methylenebisacrylamide, divinyl citraconate, diallyl fumarate, divinyl sulfone, triallyl phosphite, diallyl benzenephosphonate, hexahydro-1,3,5-triacryltriazine, divinyl ether, triallyl citrate, polysiloxanylbis(alkylglycerol acrylate), polysiloxanylbis(alkylglycerol methacrylate), or combination of two or more thereof.

26. The composition of claim 1 , wherein the composition further comprises a thermal or a photo initiator chosen from 2,2′-azobis (2,4-dimethylpentanenitrile), 2,2′-azobis (2-methylpropanenitrile), 2,2′-azobis (2-methylbutanenitrile), peroxides such as benzoyl peroxide, benzoin methyl ether, diethoxyacetophenone, a benzoylphosphine oxide, 2-hydroxy-2-methyl propiophenone (HMPP), 1-hydroxycyclohexyl phenyl ketone and Darocur and Irgacure types, or combination of two or more thereof.

27. The composition of claim 22 , wherein the ratio of alpha, beta-unsaturated amido-containing organosilicon compound to the at least one co-monomer containing an activated carbon-carbon double bond is from 1:2 to 2:1.

28. The composition of claim 22 , wherein the composition comprises from 40 to 60 weight percent alpha, beta-unsaturated amido-containing organosilicon compound and the at least one co-monomer containing an activated carbon-carbon double bond comprises 20 to 30 weight percent dimethylacrylamide, 15 to 25 weight percent 2-hydroxyethyl (meth)acrylate, 1 to 10 weight percent N-vinyl pyrolidone and 0.1 to 3 weight percent of ethylene glycol dimethyl acrylate, based on the total weight of trisiloxane containing 3-(meth)acryloxy-substituted (hydroxycyclohexyl)ethyl group of the present invention, dimethylacrylamide, 2-hydroxyethyl (meth)acrylate, N-vinyl pyrroline and ethylene glycol dimethyl acrylate.

29. A contact lens comprising a hydrogel film formed from the composition of claim 1 .

30. The contact lens of claim 29 , wherein the hydrogel film is prepared from at least one alpha, beta-unsaturated amido-containing organosilicon compound chosen from (acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-bis-(trimethylsiloxy)methylsilanyl-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-bis-(trimethylsiloxy)methylsilanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-bis-(trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[bis-(3-trimethylsiloxy)methylsilanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 3-(acryloylamino)-propionic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 2-methyl-acrylic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(2-methyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; 9-(3-methoxycarbonyl-acryloylamino)-nonanoic acid 2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyl ester; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid; 3-{2-[2-hydroxy-5-[2-tris-(trimethylsiloxy)silanyl-ethyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; 3-{2-[2-hydroxy-5-[3-tris-(trimethylsiloxy)silanyl-propyl]-cyclohexyloxycarbonyl]-ethylcarbamoyl}-acrylic acid methyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; (2-methylacryloylamino)-acetic acid 2-hydroxy-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4, 6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino-acetic acid 2-hydroxy-5-[2-(2,4,4, 6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester, (2-methyl-acryloylamino)-acetic acid 5-[2-(2,4,4,6,6,8,8-heptamethyl-[1,3,5, 7,2,4,6,8]tetroxatetrasilocan-2-yl)-ethyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-2-hydroxy-cyclohexyl ester, acryloylamino-acetic acid 4-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-2-hydroxy-cyclohexyl ester; acryloylamino-acetic acid 4-[2,4,4,6,6,8,8-heptamethyl-[1,3,5,7,2,4,6,8]tetroxatetrasilocan-2-yl]-2-hydroxy-cyclohexyl ester; and acryloylamino-acetic acid 4-[tris-(trimethylsiloxy)silanyl]-2-hydroxy-cyclohexyl ester, or a combination of two or more thereof.

31. The contact lens of claim 29 , wherein the alpha, beta-unsaturated amido-containing organosilicon compound has the stereochemistry in which the alpha, beta-unsaturated amido group and the silyl group is in a trans-1,3-substitution on the cycloalkylene linking group and having the stereochemistry of Formula (II):

wherein:

R 1 , R 2 , and R 3 are independently chosen from hydrogen, an alkyl group containing from 1 to 3 carbon atoms, a phenyl group, or R 7 C(═O)OR 8 , wherein R 7 is a chemical bond or an alkylene group containing from 1 to 6 carbon atoms, and R 8 is hydrogen or an alkyl group of from 1 to 3 carbon atoms;

R 4 is hydrogen or an alkyl group containing from 1 to 6 carbon atoms or phenyl;

R 5 is an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur, nitrogen, or a combination of two or more thereof;

R 6 is a chemical bond or an alkylene group containing from 1 to 16 carbon atoms and optionally a heteroatom of oxygen, sulfur or nitrogen;

X 1 is a methyl, trimethylsiloxy, or —O[Si(CH 3 ) 2 O—] n , wherein n is an integer of from 1 to 9;

X 2 is methyl, trimethylsiloxy or —[OSi(CH 3 ) 2 ] m G 1 , wherein G 1 is (CH 3 ) 3 SiOSi(CH 3 ) 2 O— or H(CH 3 ) 2 SiO— or alpha, beta-unsaturated amido-containing group with the general formula:

and m is an integer from 0 to 200, with the proviso that when X 2 is —[OSi(CH 3 ) 2 ] m G 2 , then X 1 and X 3 is methyl;

X 3 is methyl, trimethylsiloxy, (CH 3 ) 3 SiCH 2 CH 2 —, (CH 3 ) 3 SiCH 2 CH 2 Si(CH 3 ) 2 O— or

—OSi(CH 3 ) 2 , with the provisos that (i) when X 1 is —O[Si(CH 3 ) 2 O—] n , then X 3 is

—OSi(CH 3 ) 2 and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring, (ii) when X 3 is

—OSi(CH 3 ) 2 , then X 1 is —O[Si(CH 3 ) 2 O—] n , and X 1 forms a chemical bond with the X 3 to form a divalent —X 1 -X 3 — group, which is bonded to the silicon atom to form a cyclic polysiloxane ring.

32. The contact lens of claim 29 , wherein the alpha, beta-unsaturated amido-containing organosilicon compound is chosen from acryloylamino-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[bis-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-[tris-(2-trimethylsiloxy)silanyl-ethyl]-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-[tris-(2-trimethylsiloxy)methylsilanyl-ethyl]-cyclohexyl ester; acryloylamino-acetic acid 2-hydroxy-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanyl-ethyl)-disiloxanyl]-ethyl}-cyclohexyl ester; acryloylamino-acetic acid trans-2-hydroxy-trans-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; and (2-methyl-acryloylamino)-acetic acid trans-2-hydroxy-trans-5-{2-[dimethyl-(2-trimethylsilanyl-ethyl)-silanyl]-ethyl}-cyclohexyl ester; and acryloylamino-acetic acid trans-2-hydroxy-trans-5-[2-(2,4,4,6,6-pentamethyl-[1,3,5,2,4,6]trioxatrisilinan-2-yl)-ethyl]-cyclohexyl ester, or a combination of two or more thereof.

33. The contact lens of claim 29 , wherein the hydrogel film contains at least one co-monomer containing an activated carbon-carbon double bond selected from the group consisting of methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl acrylate, cyclohexyl methacrylate, methyl acrylate, 2-hydroxyethyl methacrylate (HEMA), N-vinylpyrrolidone (NVP), methacrylic acid (MA), and dimethylacrylamide (DMA), or a combination of two or more thereof.

34. The contact lens of claim 29 , wherein the hydrogel film contains at least one crosslinker selected from the group consisting of ethylene glycol diacrylate, ethylene glycol dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate, 1,4-butylene glycol dimethacrylate, ethylene glycol dicrotonate, diethylene glycol dimethacrylate, diethylene glycol diacrylate, dipropylene glycol dimethacrylate, dipropylene glycol diacrylate, trimethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol dicrotonate, tetraethylene glycol dimethacrylate, hexaethylene glycol dimethacrylate, tripropylene glycol diacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, tributylene glycol dimethacrylate, tetrabutylene glycol dimethacrylate, hexamethylene glycol dimethacrylate, octamethylene glycol dimethacrylate, decamethylene glycol dimethacrylate, allyl methacrylate, divinylbenzene, diallyl phthalate, trimethylolpropane trimethacrylate, diallyl tartrate, diallyl maleate, triallylmelamine, N,N′-methylenebisacrylamide, divinyl citraconate, diallyl fumarate, divinyl sulfone, triallyl phosphite, diallyl benzenephosphonate, hexahydro-1,3,5-triacryltriazine, divinyl ether, triallyl citrate, polysiloxanylbis(alkylglycerol acrylate) and polysiloxanylbis(alkylglycerol methacrylate), or a combination of two or more thereof.

35. The contact lens claim 33 , wherein the hydrogel film is made from co-monomers having the ratio of alpha, beta-unsaturated amido-containing organosilicon compound to the at least one co-monomer containing an activated carbon-carbon double bond of from 1:2 to 2:1.

36. The contact lens of claim 33 wherein the hydrogel film is made from co-monomers where the alpha, beta-unsaturated amido-containing organosilicon compound is from 40 to 100 weight percent and the at least one co-monomer containing an activated carbon-carbon double bond comprises from 10 to 30 weight percent dimethylacrylamide, 0 to 25 weight percent 2-hydroxyethyl (meth)acrylate, 0 to 10 weight percent N-vinyl pyrroline and 0.1 to 3 weight percent of ethylene glycol dimethyl acrylate, based on the total weight of trisiloxane containing 3-(meth)acryloxy-substituted (hydroxycyclohexyl)ethyl group of the present invention, dimethylacrylamide, 2-hydroxyethyl (meth)acrylate, N-vinyl pyrroline and ethylene glycol dimethyl acrylate.

37. The composition according to claim 1 , wherein the composition is a film forming additive in textile, paper, leather, personal care, home care, coating, painting and seed treatment formulations.

Assignments (12)
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
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From: KOOKMIN BANK NEW YORK
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From: MOMENTIVE PERFORMANCE MATERIALS INC.
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FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
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To: MOMENTIVE PERFORMANCE MATERIALS INC.
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