US4711943A — Hydrophilic siloxane monomers and dimers for cont…

Claim 1

Independent Claim 106 words

A non-fibrous polymeric contact lens material having improved oxygen permeability and stability, said polymeric contact lens material comprising a monomer having the following structural formula: first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae: ##STR51## and a second portion for increasing oxygen permeability, said second portion including a siloxane; wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 2

Dependent Claim 106 words

A non-fibrous polymeric contact lens material having improved oxygen permeability and stability, said polymeric contact lens material comprising a monomer having the following structural formula: first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae: ##STR51## and a second portion for increasing oxygen permeability, said second portion including a siloxane; wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 3

Dependent Claim 17 words

The contact lens material of claim 1 wherein said first portion comprises an acrylamide or a methacrylamide.

Claim 4

Dependent Claim 15 words

The contact lens material of claim 1 wherein said second portion comprises an alkyl siloxane.

Claim 5

Dependent Claim 15 words

The contact lens material of claim 2 wherein said second portion comprises an alkyl siloxane.

Claim 6

Dependent Claim 75 words

The contact lens material of claim 1 wherein said first portion comprises the following structural formula: ##STR52## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula: ##STR53##

Claim 7

Dependent Claim 24 words

The contact lens material of claim 1 wherein said first portion comprises the following structural formula: ##STR54## wherein X is CH 3 or H.

Claim 8

Dependent Claim 82 words

The contact lens material of claim 1 wherein said second portion comprises the following structural formula: ##STR55## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR56## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

Claim 9

Dependent Claim 82 words

The contact lens material of claim 5 wherein said second portion comprises the following structural formula: ##STR57## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR58## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

Claim 10

Dependent Claim 23 words

The contact lens material of claim 7 wherein: n is 3; and Z 1 , Z 2 and Z 3 are lower alkyl.

Claim 11

Dependent Claim 23 words

The contact lens material of claim 8 wherein: n is 3; and Z 1 , Z 2 and Z 3 are lower alkyl.

Claim 12

Dependent Claim 20 words

The contact lens material of claim 9 wherein Z 1 , Z 2 and Z 3 are CH 3 .

Claim 13

Dependent Claim 20 words

The contact lens material of claim 10 wherein Z 1 , Z 2 and Z 3 are CH 3 .

Claim 14

Dependent Claim 17 words

The contact lens material of claim 6 wherein said second portion has the following structural formula: ##STR59##

Claim 15

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 1.

Claim 16

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 5.

Claim 17

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 7.

Claim 18

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 8.

Claim 19

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 13.

Claim 20

Dependent Claim 194 words

A non-fibrous polymeric material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a monomer having the following structural formula: ##STR60## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula; ##STR61## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR62## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 21

Dependent Claim 194 words

A non-fibrous polymeric material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a monomer having the following structural formula: ##STR60## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula; ##STR61## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR62## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 22

Dependent Claim 27 words

The contact lens material of claim 19 wherein: m is 0; n is 3; and Z 1 , Z 2 and Z 3 are CH 3 .

Claim 23

Dependent Claim 14 words

The contact lens material of claim 20 wherein X 1 is CH 3 .

Claim 24

Dependent Claim 12 words

The contact lens material of claim 20 wherein X 2 is H.

Claim 25

Dependent Claim 12 words

The contact lens material of claim 21 wherein X 2 is H.

Claim 26

Dependent Claim 12 words

A contact lens made from the contact lens material of claim 19.

Claim 27

Dependent Claim 77 words

A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR63## wherein: said material has a water content of about 15-60%; DK greater than or equal to about 24×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 28

Dependent Claim 77 words

A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR63## wherein: said material has a water content of about 15-60%; DK greater than or equal to about 24×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 29

Dependent Claim 77 words

A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR64## wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 30

Dependent Claim 77 words

A non-fibrous contact lens material for making a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR64## wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 31

Dependent Claim 117 words

A non-fibrous contact lens material comprising the copolymerization product of: (a) a first monomer having: a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group consisting of the following structural formulae: ##STR65## and a second portion for increasing oxygen permeability, said second portion including a siloxane; (b) a second monomer, copolymerizable with said first monomer; (c) a crosslinking agent; and (d) a polymerization initiator; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 32

Dependent Claim 117 words

A non-fibrous contact lens material comprising the copolymerization product of: (a) a first monomer having: a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group consisting of the following structural formulae: ##STR65## and a second portion for increasing oxygen permeability, said second portion including a siloxane; (b) a second monomer, copolymerizable with said first monomer; (c) a crosslinking agent; and (d) a polymerization initiator; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 33

Dependent Claim 47 words

The contact lens material of claim 27 comprising the copolymerization product of: (a) 30-100 wt/wt% of said first monomer; (b) 0-70 wt/wt% of said second monomer; (c) 0-10 wt/wt% of said crosslinking agent; (d) 0-5 wt/wt% of said polymerization initiator; and (e) 0-20 wt/wt% of a diluent.

Claim 34

Dependent Claim 47 words

The contact lens material of claim 28 comprising the copolymerization product of: (a) 35-45 wt/wt% of said first monomer; (b) 45-55 wt/wt% of said second monomer; (c) 0-10 wt/wt% of said crosslinking agent; (d) 0-5 wt/wt% of said polymerization initiator; and (e) 0-10 wt/wt% of a diluent.

Claim 35

Dependent Claim 47 words

The contact lens material of claim 28 comprising the copolymerization product of: (a) 38-44 wt/wt% of said first monomer; (b) 47-52 wt/wt% of said second monomer; (c) 3-8 wt/wt% of said crosslinking agent; (d) 0-1 wt/wt% of said polymerization initiator; and (e) 0-7 wt/wt% of a diluent.

Claim 36

Dependent Claim 47 words

The contact lens material of claim 28 comprising the copolymerization product of: (a) 41 wt/wt% of said first monomer; (b) 49 wt/wt% of said second monomer; (c) 5.5 wt/wt% of said crosslinking agent; (d) 0.5 wt/wt% of said polymerization initiator; and (e) 4.0 wt/wt% of said diluent.

Claim 37

Dependent Claim 13 words

The contact lens material of claim 28 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

Claim 38

Dependent Claim 13 words

The contact lens material of claim 29 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

Claim 39

Dependent Claim 13 words

The contact lens material of claim 32 wherein said first monomer is N-[tris(trimethylsiloxy)silylpropyl]methacrylamide.

Claim 40

Dependent Claim 13 words

The contact lens material of claim 28 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 41

Dependent Claim 13 words

The contact lens material of claim 29 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 42

Dependent Claim 13 words

The contact lens material of claim 32 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 43

Dependent Claim 13 words

The contact lens material of claim 33 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 44

Dependent Claim 13 words

The contact lens material of claim 34 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 45

Dependent Claim 13 words

The contact lens material of claim 35 wherein said crosslinking agent is 1,3-Bis(methacrylamidopropyl)-1,1,3,3-tetrakis(trimethylsiloxy)disiloxane.

Claim 46

Dependent Claim 138 words

The contact lens material of claim 28 wherein said first monomer has the following structural formula: ##STR66## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; n is an integer from 1 to 6; Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula: ##STR67## A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR68## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

Claim 47

Dependent Claim 27 words

The contact lens material of claim 41 wherein: m is 0; n is 3; and Z 1 , Z 2 and Z 3 are CH 3 .

Claim 48

Dependent Claim 14 words

The contact lens material of claim 42 wherein X 1 is CH 3 .

Claim 49

Dependent Claim 12 words

The contact lens material of claim 42 wherein X 2 is H.

Claim 50

Dependent Claim 14 words

The contact lens material of claim 44 wherein X 1 is CH 3 .

Claim 51

Dependent Claim 15 words

The contact lens material of claim 32 wherein said crosslinking agent is ethyleneglycoldimethacrylate or tetraethyleneglycoldimethacrylate.

Claim 52

Dependent Claim 31 words

The contact lens material of claim 28 wherein said second monomer is selected from the group consisting of: methyl methacrylate, hydroxyethyl methacrylate, glyceryl methacrylate, N,N-dimethylacrylamide, N-Vinyl pyrrolidone, α-Methylglucoside-6-methacrylate, and methacrylic acid.

Claim 53

Dependent Claim 102 words

The contact lens material of claim 27 wherein said crosslinking agent comprises the following structural formula: ##STR69## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; n is an integer from 1 to 6; A 1 to A 3 are the same or different and are selected from lower alkyl, phenyl, benzyl, and tri-substituted-siloxy; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to a carbon bearing an X 1 substituent in the above formula: ##STR70##

Claim 54

Dependent Claim 102 words

The contact lens material of claim 41 wherein said crosslinking agent comprises the following structural formula: ##STR71## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; n is an integer from 1 to 6; A 1 to A 3 are the same or different and are selected from lower alkyl, phenyl, benzyl, and tri-substituted-siloxy; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to a carbon bearing an X 1 substituent in the above formula: ##STR72##

Claim 55

Dependent Claim 107 words

A non-fibrous contact lens material having improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having: a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae: ##STR73## and a second portion for increasing oxygen permeability, said second portion including a siloxane; wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 56

Dependent Claim 107 words

A non-fibrous contact lens material having improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having: a first portion for increasing wettability, said first portion being hydrophilic and including a side-chain functionality selected from the group including the following structural formulae: ##STR73## and a second portion for increasing oxygen permeability, said second portion including a siloxane; wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 57

Dependent Claim 17 words

The contact lens material of claim 50 wherein said first portion comprises an acrylamide or a methacrylamide.

Claim 58

Dependent Claim 16 words

The contact lens material of claim 50 wherein said second portion comprises an alkyl silyl siloxane.

Claim 59

Dependent Claim 16 words

The contact lens material of claim 51 wherein said second portion comprises an alkyl silyl siloxane.

Claim 60

Dependent Claim 75 words

The contact lens material of claim 50 wherein said first portion comprises the following structural formula: ##STR74## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula: ##STR75##

Claim 61

Dependent Claim 24 words

The contact lens material of claim 50 wherein said first portion comprises the following structural formula: ##STR76## wherein X is CH 3 or H.

Claim 62

Dependent Claim 82 words

The contact lens material of claim 50 wherein said second portion comprises the following structural formula: ##STR77## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR78## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

Claim 63

Dependent Claim 82 words

The contact lens material of claim 54 wherein said second portion comprises the following structural formula: ##STR79## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR80## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkylsiloxy substituents.

Claim 64

Dependent Claim 23 words

The contact lens material of claim 56 wherein: n is 3; and Z 1 , Z 2 and Z 3 are lower alkyl.

Claim 65

Dependent Claim 23 words

The contact lens material of claim 57 wherein: n is 3; and Z 1 , Z 2 and Z 3 are lower alkyl.

Claim 66

Dependent Claim 20 words

The contact lens material of claim 58 wherein Z 1 , Z 2 and Z 3 are CH 3 .

Claim 67

Dependent Claim 20 words

The contact lens material of claim 59 wherein Z 1 , Z 2 and Z 3 are CH 3 .

Claim 68

Dependent Claim 17 words

The contact lens material of claim 55 wherein said second portion has the following structural formula: ##STR81##

Claim 69

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 50.

Claim 70

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 54.

Claim 71

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 56.

Claim 72

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 57.

Claim 73

Dependent Claim 12 words

A contact lens formed from the contact lens material of claim 62.

Claim 74

Dependent Claim 199 words

A non-fibrous material for working a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR82## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula, ##STR83## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR84## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 75

Dependent Claim 199 words

A non-fibrous material for working a contact lens with improved oxygen permeability and stability, said contact lens material comprising a polymer formed from at least a monomer having the following structural formula: ##STR82## wherein: X 1 is CH 3 or H; X 2 is CH 3 or H; m is 0 or 1; and Y is selected from the group consisting of the following structural formulae, the radical shown on the left of each formula being bonded to the carbon shown on the left of Y in the above formula, ##STR83## wherein: n is an integer from 1 to 6; A 1 and A 2 are the same or different and are selected from lower alkyl and B groups; and B has the following structural formula: ##STR84## wherein: Z 1 , Z 2 and Z 3 are the same or different and are selected from the group consisting of lower alkyl, phenyl, benzyl and tri-alkyl-siloxy substituents; and wherein: said material has a water content of about 15-60%; DK greater than or equal to about 25×10 -10 ; tear strength greater than or equal to about 1.0 g/mm 2 ; and percent elongation greater than or equal to about 80%.

Claim 76

Dependent Claim 27 words

The contact lens material of claim 68 wherein: m is 0; n is 3; and Z 1 , Z 2 and Z 3 are CH 3 .

Claim 77

Dependent Claim 14 words

The contact lens material of claim 69 wherein X 1 is CH 3 .

Claim 78

Dependent Claim 12 words

The contact lens material of claim 69 wherein X 2 is H.

Claim 79

Dependent Claim 12 words

The contact lens material of claim 70 wherein X 2 is H.

Claim 80

Dependent Claim 12 words

A contact lens made from the contact lens material of claim 69.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1990-12-07	1991-06-08	1991-12-08	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1994-12-07	1995-06-08	1995-12-08	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1998-12-07	1999-06-08	1999-12-08	$7700.00	Window Closed / Lapsed

Hydrophilic siloxane monomers and dimers for contact lens materials, and contact lenses fabricated therefrom

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