U.S. patent application number 10/639823 was filed with the patent office on 2004-04-22 for molds for producing contact lenses.
Invention is credited to Abrams, Richard W., Ansell, Scott F., Copper, Lenora L., Dubey, Dharmesh K., Fougere, Richard J., Gourd, Dominic, Matiacio, Thomas A., McCabe, Kevin P., Rooney, Thomas R., Song, Xu, Tumer, David C..
Application Number | 20040075039 10/639823 |
Document ID | / |
Family ID | 31890920 |
Filed Date | 2004-04-22 |
United States Patent
Application |
20040075039 |
Kind Code |
A1 |
Dubey, Dharmesh K. ; et
al. |
April 22, 2004 |
Molds for producing contact lenses
Abstract
This invention describes molds made from alicyclic co-polymers
that are useful in the production of contact lenses and methods for
their use.
Inventors: |
Dubey, Dharmesh K.;
(Jacksonville, FL) ; Tumer, David C.;
(Jacksonville, FL) ; Copper, Lenora L.;
(Jacksonville, FL) ; Matiacio, Thomas A.;
(Jacksonville, FL) ; Abrams, Richard W.;
(Jacksonville, FL) ; McCabe, Kevin P.;
(Jacksonville, FL) ; Ansell, Scott F.;
(Jacksonville, FL) ; Fougere, Richard J.; (Ponte
Vedre Beach, FL) ; Gourd, Dominic; (Jacksonville,
FL) ; Rooney, Thomas R.; (Jacksonville, FL) ;
Song, Xu; (Jacksonville, FL) |
Correspondence
Address: |
PHILIP S. JOHNSON
JOHNSON & JOHNSON
ONE JOHNSON & JOHNSON PLAZA
NEW BRUNSWICK
NJ
08933-7003
US
|
Family ID: |
31890920 |
Appl. No.: |
10/639823 |
Filed: |
August 13, 2003 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10639823 |
Aug 13, 2003 |
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10395755 |
Mar 24, 2003 |
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10395755 |
Mar 24, 2003 |
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10222373 |
Aug 16, 2002 |
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Current U.S.
Class: |
249/134 ;
425/808 |
Current CPC
Class: |
B29D 11/00432 20130101;
C08G 61/08 20130101; B29C 33/40 20130101; B29K 2823/38 20130101;
C08L 39/06 20130101; C08L 33/26 20130101; B29D 11/00865 20130101;
C08L 2205/035 20130101; C08L 45/00 20130101; C08L 33/26 20130101;
C08L 2666/02 20130101 |
Class at
Publication: |
249/134 ;
425/808 |
International
Class: |
B29D 011/00 |
Claims
What is claimed is:
1. A mold for making a lens comprising an alicyclic co-polymer
wherein said alicyclic co-polymer comprises at least two alicyclic
monomers of different chemical structures.
2. The mold of claim 1 wherein the alicyclic monomers comprise
polymerizable cyclobutanes, cyclopentanes, cyclohexanes,
cycloheptanes, cycloctanes, biscyclobutanes, biscyclopentanes,
biscyclohexanes, biscycloheptanes, biscyclooctanes, or
norbornanes.
3. The mold of claim 1 comprising two alicyclic monomers wherein
the alicyclic monomers comprise a saturated carbocyclic ring.
4. The mold of claim 1 wherein the alicyclic monomers are selected
from the group consisting of 4wherein R.sup.1-6 are independently
selected from one or more members of the group consisting of
hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
5. The mold of claim 1 wherein the alicyclic monomers are selected
from the group consisting of 5wherein two or more of R.sup.1-6 are
taken together to form an unsaturated bond, a carbocyclic ring, a
carbocyclic ring containing one or more unsaturated bonds, or an
aromatic ring.
6. The mold of claim 1 wherein the alicyclic monomers are selected
from the group consisting of 6wherein R.sup.1-6 are independently
selected from one or more members of the group consisting of
hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from one or more members of the group consisting of
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy,
cyano, amido, imido and silyl.
7. The mold of claim 1 where R.sup.1-6 C.sub.1-10alkyl, or
substituted C.sub.1-10alkyl where the substituents are selected
from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
8. The mold of claim 1 wherein the alicyclic monomers are 7wherein
R.sup.1-4 is independently selected from C.sup.1-10alkyl.
9. The mold of claim 1 wherein the alicyclic co-polymer has a MFR
of about 11.0 grams/10 minutes to about 18.0 grams/10 minutes, a
specific gravity of 1.01 and a glass transition temperature of
105.degree. C.
10. The mold of claim 1 wherein the mold further comprises an
additive.
11. The mold of claim 10 wherein the additive is about 2.0 weight
percent zinc sterate.
12. The mold of claim 10 wherein the additive is about 2.0 percent
glycerol monostearate.
13. The mold of claim 1 wherein the front curve and the back curve
comprise an alicyclic co-polymer having a MFR of about 11.0
grams/10 minutes to about 18.0 grams/10 minutes, a specific gravity
of 1.01 and a glass transition temperature of 105.degree. C.
14. The mold of claim 1 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene.
15. The mold of claim 1 wherein the back curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the front curve
comprises polypropylene.
16. The mold of claim 1 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene and an alicyclic co-polymer having a melt
flow of 14, a share rate of MFR=12.0 g and 17.6 g, a specific
gravity of 1.01, and a glass transition temperature of 1050.
17. The mold of claim 1 wherein the back curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the front curve
comprises polypropylene and an alicyclic co-polymer having a MFR of
about 11.0 grams/10 minutes to about 18.0 grams/10 minutes, a
specific gravity of 1.01 and a glass transition temperature of
105.degree. C.
18. The mold of claim 16 wherein the ratio of alicyclic co-polymer
to polypropylene is about 5:95 to about 95:5.
19. The mold of claim 16 wherein the ratio of alicyclic co-polymer
to polypropylene is about 20:80 to about 80:20.
20. A method of making a lens comprising 1) dispensing an uncured
lens formulation onto a mold surface comprising an alicyclic
co-polymer wherein said alicyclic co-polymer comprises at least two
alicyclic monomers of different chemical structures, and 2) curing
said lens formulation under suitable conditions.
21. The method of claim 20 comprising two alicyclic monomers
wherein the alicyclic monomers comprise a saturated carbocyclic
ring.
22. The method of claim 20 wherein the alicyclic monomers are
selected from the group consisting of 8wherein
R.sup.1.sup..sub.--.sup.6 are independently selected from one or
more members of the group consisting of hydrogen, C.sub.1-10alkyl,
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl- , C.sub.1-10alkoxy,
cyano, amido, imido, silyl, and substituted C.sub.1-10alkyl where
the substituents are selected from the group consisting of halogen,
hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido,
imido and silyl.
23. The method of claim 20 wherein the alicyclic monomers are
selected from the group consisting of 9wherein two or more of
R.sup.1-6 are taken together to form an unsaturated bond, a
carbocyclic ring, a carbocyclic ring containing one or more
unsaturated bonds, or an aromatic ring.
24. The method of claim 20 wherein the alicyclic monomers are
selected from the group consisting of 10wherein R.sup.1-6 are
independently selected from one or more members of the group
consisting of hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from one or more members of the group consisting of
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy,
cyano, amido, imido and silyl.
25. The method of claim 20 where R.sup.1-6 C.sub.1-10alkyl, or
substituted C.sub.1-10alkyl where the substituents are selected
from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
26. The method of claim 20 wherein the alicyclic monomers are
selected from the group consisting of 11wherein R.sup.1-4 is
independently selected from C.sup.1-10alkyl.
27. The method of claim 20 wherein the mold surface comprises a
front curve and a back curve and the method further comprises the
step of 3) separating the front curve of the lens mold and the back
curve of the lens mold where the cured lens removably adheres to
the front curve.
28. The method of claim 20 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene.
29. The method of claim 26 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene and an alicyclic co-polymer having a MFR of
about 11.0 grams/10 minutes to about 18.0 grams/10 minutes, a
specific gravity of 1.01 and a glass transition temperature of
105.degree. C.
30. The method of claim 28 wherein the ratio of alicyclic
co-polymer to polyproylene in the back curve is about 20:80 to
about 80:20.
31. The method of claims 28 wherein the ratio of alicyclic
co-polymer to polyproylene in the back curve is about 55:45.
32. A mold comprising an alicyclic co-polymer and at least one lens
forming surface wherein said alicyclic co-polymer comprises at
least two alicyclic monomers of different chemical structures, and
wherein said at least one lens forming surface comprises a coating
effective amount of a high molecular weight coating
composition.
33. The mold of claim 32 comprising two alicyclic monomers wherein
the alicyclic monomers comprise a saturated carbocyclic ring.
34. The mold of claim 32 wherein the alicyclic monomers are
selected from the group consisting of 12wherein R.sup.1-6 are
independently selected from one or more members of the group
consisting of hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
35. The mold of claim 32 wherein the alicyclic monomers are
selected from the group consisting of 13wherein two or more of
R.sup.1-6 are be taken together to form an unsaturated bond, a
carbocyclic ring, a carbocyclic ring containing one or more
unsaturated bonds, or an aromatic ring.
36. The mold of claim 32 wherein the alicyclic monomers are
selected from the group consisting of 14wherein R.sup.1-6 are
independently selected from one or more members of the group
consisting of hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from one or more members of the group consisting of
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy,
cyano, amido, imido and silyl.
37. The mold of claim 32 where R.sup.1-6 C.sub.1-10alkyl, or
substituted C.sub.1-10alkyl where the substituents are selected
from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
38. The mold of claim 32 wherein the alicyclic monomers are
selected from the group consisting of 15wherein R.sup.1-4 is
independently selected from C.sup.1-10alkyl.
39. The mold of claim 32 wherein the mold further comprises an
additive.
40. The mold of claim 39 wherein the additive is about 2.0 weight
percent zinc stearate.
41. The mold of claim 39 wherein the additive is about 2.0 weight
percent zinc stearate.
42. The mold of claim 39 wherein the coating composition comprises
a coating additive.
43. The mold of claim 39 wherein the additive is an antimicrobial
composition.
44. A lens produced by a method comprising 1) dispensing an uncured
lens formulation onto a surface of a mold comprising an alicyclic
co-polymer wherein said alicyclic co-polymer comprises at least two
alicyclic monomers of different chemical structures and 2) curing
said lens formulation under suitable conditions.
45. The lens of claim 44 comprising two alicyclic monomers wherein
the alicyclic monomers comprise a saturated carbocyclic ring.
46. The lens of claim 44 wherein the alicyclic monomers are
selected from the group consisting of 16wherein
R.sup.1.sup..sub.--.sup.6 are independently selected from one or
more members of the group consisting of hydrogen, C.sub.1-10alkyl,
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl- , C.sub.1-10alkoxy,
cyano, amido, imido, silyl, and substituted C.sub.1-10alkyl where
the substituents are selected from the group consisting of halogen,
hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido,
imido and silyl.
47. The lens of claim 44 wherein the alicyclic monomers are
selected from the group consisting of 17wherein R.sup.1-6 are
independently selected from one or more members of the group
consisting of hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from one or more members of the group consisting of
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy,
cyano, amido, imido and silyl.
48. The lens of claim 44 where R.sup.1-6 C.sub.1-10alkyl, or
substituted C.sub.1-10alkyl where the substituents are selected
from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl.
49. The lens of claim 44 wherein the alicyclic monomers are
selected from the group consisiting of 18wherein R.sup.1-4 is
independently selected from C.sup.1-10alkyl.
50. The lens of claim 44 wherein the uncured lens formulation
comprises silicone hydrogel formulations.
51. The lens of claim 44 wherein the uncured lens formulation
comprises hydrogel formulations.
52. The lens of claim 44 wherein the uncured lens formulation
comprises the formulations of acquafilcon A, balafilcon A,
lotrafilcon A.
53. The lens of claim 44 wherein the uncured lens formulations
comprise the formulation of etafilcon A, genfilcon A, lenefilcon A,
polymacon, acquafilcon A, balafilcon A, galyfilcon A, or senofilcon
A, or lotrafilcon A.
54. The lens of claim 44 wherein the uncured lens formulation
comprises the formulations of acquafilcon A, balafilcon A,
lotrafilcon A, galyfilcon A, or senofilcon A.
55. The lens of claim 44 wherein the mold surface comprises a front
curve and a back curve.
56. The lens of claim 55 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene.
57. The lens of claim 55 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene and an alicyclic co-polymer having a MFR of
about 11.0 grams/10 minutes to about 18.0 grams/10 minutes, a
specific gravity of 1.01 and a glass transition temperature of
105.degree. C.
58. The lens of claim 55 wherein the ratio of alicyclic co-polymer
to polyproylene in the back curve is about 20:80 to about
80:20.
59. The lens of claim 55 wherein the ratio of alicyclic co-polymer
to polyproylene in the back curve is about 55:45.
60. A method for making a coated lenses comprising (1) coating at
least one lens forming surface of a lens mold with a coating
effective amount of a high molecular weight coating composition
wherein said lens mold comprises an alicyclic co-polymer and at
least one lens forming surface wherein said alicyclic co-polymer
comprises at lease two alicyclic monomers of different chemical
structures; (2) dispensing an uncured lens formulation onto said at
least one lens forming surface; and (3) curing said lens
formulation and said coating composition using a dwell time of less
than about 5 minutes and under conditions suitable to form a coated
lens.
61. The method of claim 60 comprising two alicyclic monomers
wherein the alicyclic monomers comprise a saturated carbocyclic
ring.
62. The method of claim 60 wherein the alicyclic monomers are
selected from the group consisting of 19wherein
R.sup.1.sup..sub.--.sup.6 are independently selected from one or
more members of the group consisting of hydrogen, C.sub.1-10alkyl,
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl- , C.sub.1-10alkoxy,
cyano, amido, imido, silyl, and substituted C.sub.1-10alkyl where
the substituents are selected from the group consisting of halogen,
hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido,
imido and silyl.
63. The method of claim 60 wherein the alicyclic monomers are
selected from the group consisting of 20wherein R.sup.1-6 are
independently selected from one or more members of the group
consisting of hydrogen, C.sub.1-10alkyl, halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
silyl, and substituted C.sub.1-10alkyl where the substituents are
selected from one or more members of the group consisting of
halogen, hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy,
cyano, amido, imido and silyl.
64. The method of claim 60 where R.sup.1-6 C.sub.1-10alkyl, or
substituted C.sub.1-10alkyl where the substituents are selected
from the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy group, cyano, amido,
imido and silyl.
65. The method of claim 60 wherein the alicyclic monomers are
selected from the group consisting of 21wherein R.sup.1-4 is
independently selected from C.sup.1-10alkyl.
66. The method of claim 60 wherein the high molecular weight
coating composition comprises poly(vinyl alcohol), polyethylene
oxide, poly(2-hydroxyethyl methacrylate), poly(methyl
methacrylate), poly(acrylic acid), poly(methacrylic acid),
poly(maleic acid), poly(itaconic acid), poly(acrylamide),
poly(methacrylamide), poly(dimethylacrylamide), poly(glycerol
methacrylate), polystyrene sulfonic acid, polysulfonate polymers,
poly(vinyl pyrrolidone), carboxymethylated polymers, such as
carboxymethylcellulose, polysaccharides, glucose amino glycans,
polylactic acid, polyglycolic acid, block or random copolymers of
the aforementioned, and mixtures thereof.
67. The method of claim 60 wherein the high molecular weight
coating composition comprises poly(2-hydroxyethyl methacrylate),
poly(vinyl pyrrolidone), poly(acrylic acid), poly(methacrylic
acid), poly(meth)acrylamide, or poly(acrylamide) and mixtures
thereof.
68. The method of claim 60 wherein the high molecular weight
coating composition comprises poly(2-hydroxyethyl
methacrylate).
69. The method of claim 60 wherein the high molecular weight
coating composition comprises poly(vinyl alcohol), polyethylene
oxide, poly(2-hydroxyethyl methacrylate), poly(methyl
methacrylate), poly(acrylic acid), poly(methacrylic acid),
poly(maleic acid), poly(itaconic acid), poly(acrylamide),
poly(methacrylamide), poly(dimethylacrylamide), poly(glycerol
methacrylate), polystyrene sulfonic acid, polysulfonate polymers,
poly(vinyl pyrrolidone), carboxymethylated polymers, such as
carboxymethylcellulose, polysaccharides, glucose amino glycans,
polylactic acid, polyglycolic acid, block or random copolymers of
the aforementioned, and mixtures thereof.
70. The method of claim 60 wherein the mold surface comprises a
front curve and a back curve.
71. The method of claim 70 wherein the front curve comprises an
alicyclic co-polymer and the back curve comprises
polypropylene.
72. The method of claim 70 wherein the front curve comprises an
alicyclic co-polymer and the back curve comprises an alicyclic
co-polymer and prolypropylene.
73. The method of claim 70 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene.
74. The method of claim 70 wherein the front curve comprises an
alicyclic co-polymer having a MFR of about 11.0 grams/10 minutes to
about 18.0 grams/10 minutes, a specific gravity of 1.01 and a glass
transition temperature of 105.degree. C. and the back curve
comprises polypropylene and an alicyclic co-polymer having a MFR of
about 11.0 grams/10 minutes to about 18.0 grams/10 minutes, a
specific gravity of 1.01 and a glass transition temperature of
105.degree. C.
75. The method of claim 74 wherein the ratio of alicyclic
co-polymer to polyproylene in the back curve is about 20:80 to
about 80:20.
76. The method of claims 74 wherein the ratio of alicyclic
co-polymer to polyproylene in the back curve is about 55:45.
Description
RELATED APPLICATIONS
[0001] This application is a continuation-in-part of U.S. patent
application Ser. No. 10/395,755, which is a continuation-in-part of
U.S. patent application Ser. No. 10/222,373.
[0002] This invention describes molds that are useful in the
production of contact lenses and methods for their use.
BACKGROUND
[0003] Contact lenses have been used commercially to improve vision
since the 1950s. The first contact lenses were made of hard
materials. Although these lenses are currently used, they are not
suitable for all patients due to their poor initial comfort and
their relatively low permeability to oxygen. Later developments in
the field gave rise to soft contact lenses, based upon hydrogels,
which are extremely popular today. These lenses have higher oxygen
permeability and are often more comfortable to wear than contact
lenses made of hard materials. Unlike hard lenses that are
manufactured by lathing hard pieces of plastic, malleable soft
contact lenses are often manufactured by forming the lens using a
two part mold where each half has topography consistent with the
desired final lens. Examples of such molds and their methods of
production may be found in U.S. Pat. Nos. 4,565,348, 4,640, 489,
4,495,313, JP 08025378, and JP 0726644 which are hereby
incorporated by reference in their entirety.
[0004] These two part molds contain a male member whose convex
surface corresponds to the back curve of a finished lens and a
female member whose concave surface corresponds to the front curve
of a finished lens. To prepare lenses using these molds, an uncured
lens formulation is placed between the concave and convex surfaces
of the mold halves and subsequently cured. The cured lens and the
mold are subsequently treated with a liquid medium in order to
release the cured lens from the surface of the mold. Although this
is a process is straightforward, there are a number requirements
that must be satisfied in order to produce a useable lens. First
the material from which the mold is made must have properties that
are chemically compatible with the uncured lens formulation.
Second, the mold material must be able to withstand the curing
conditions and be compatible with such conditions. For example,
lenses may be cured by either or both heat and light. If a lens is
cured by transmitting light to the uncured polymer, it is important
that the lens mold permit the transmission of light at the
appropriate wavelength. Third, the mold material must not stick to
the cured lens to a degree that prevents release of the cured lens.
Often the lenses are produced in a manufacturing environment where
it is important for the lenses to removably adhere to the same said
of the lens mold upon separation in a repeatable and predictable
fashion. Therefore, the selection of appropriate materials to make
the molds continues to be a subject of concern to those who produce
soft contact lenses.
[0005] Others have used materials such as polypropylene,
polystryene, polyethylene, polymethyl methacrylates, and modified
polyolefins containing an alicyclic moiety in the main chain to
prepare two part lens molds. Although these materials are useful,
with discovery of different lens formulations, particularly
silicone hydrogel lens formulations, other useful mold materials
are needed.
[0006] Further, new developments in the field have led to contact
lenses made from hydrogels and silicone hydrogels that are coated
with polymers to improve the comfort of the lenses. Often lenses
are coated by treating the cured lenses with a polymer. Recently
polymer coated lenses have been produced by coating the surfaces of
a two part mold with a polymer, adding an uncured formulation to
the coated lens mold, curing the lens, and subsequently releasing
the cured lens from the mold where the surface of said cured lens
is coated with the polymer that was originally adhered to the
surface of the mold. This process is described in further detail in
U.S. patent application Ser. No. 09/921,192, filed on Aug. 8, 2001
and entitled "Method for Correcting Articles by Mold Transfer,"
which is hereby incorporated by reference in its entirety. When
using this method of coating a lens, the choice of mold material is
even more critical than when one is producing an uncoated lens.
[0007] Therefore, there remains an unmet need to produce lens molds
that may be used to produce many different types of soft contact
lenses. It is this need that the following invention fills.
DETAILED DESCRIPTION OF THE INVENTION
[0008] This invention includes a mold for making a lens comprising,
consisting essentially of, or consisting of an alicyclic co-polymer
wherein said alicyclic co-polymer comprises, consists essentially
of, or consists of at least two alicyclic monomers of different
chemical structures. As used herein "lens" refers to any ophthalmic
device that resides in or on the eye. These devices can provide
optical correction or may be cosmetic. The term lens includes but
is not limited to soft contact lenses, intraocular lenses, overlay
lenses, ocular inserts, and optical inserts. The preferred lenses
of the invention are soft contact lenses are made from silicone
elastomers or hydrogels, which include but are not limited to
silicone hydrogels, and fluorohydrogels. Soft contact lens
formulations are disclosed in U.S. Pat. No. 5,710,302, WO 9421698,
EP 406161, JP 2000016905, U.S. Pat. No. 5,998,498, U.S. patent
application Ser. No. 09/957,299 filed on Sep. 20, 2001, U.S. patent
application Ser. No. 09/532,943, U.S. Pat. No. 6,087,415, U.S. Pat.
No. 5,760,100, U.S. Pat. No. 5,776,999, U.S. Pat. No. 5,789,461,
U.S. Pat. No. 5,849,811, and U.S. Pat. No. 5,965,631. Further
polymers that may be used to form soft contact lenses are disclosed
in the following U.S. Pat. Nos. 6,419,858; 6,308,314; and
6,416,690. The foregoing references are hereby incorporated by
reference in their entirety. The particularly preferred lenses of
the inventions are etafilcon A, genfilcon A, lenefilcon A,
polymacon, acquafilcon A, balafilcon A, lotrafilcon A, galyfilcon
A, senofilcon A, silicone hydrogels as prepared in U.S. Pat. No.
5,998,498, U.S. patent application Ser. No. 09/532,943, a
continuation-in-part of U.S. patent application Ser. No.
09/532,943, filed on Aug. 30, 2000, U.S. patent Ser. No. 09/957,
299 filed on Sep. 20, 2001, soft contact lenses as prepared in U.S.
Pat. App. No. 60/318,536, entitled Biomedical Devices Containing
Internal Wetting Agents," filed on Sep. 10, 2001 and its
non-provisional counterpart of the same title, filed on Sep. 6,
2002, U.S. Pat. No. 6,087,415, U.S. Pat. No. 5,760,100, U.S. Pat.
No. 5,776,999, U.S. Pat. No. 5,789,461, U.S. Pat. No. 5,849,811,
and U.S. Pat. No. 5,965,631. These patents (and applications) as
well as all other patent disclosed in this application are hereby
incorporated by reference in their entirety.
[0009] As used herein, the term "alicyclic monomers" refers to
polymerizable compounds having at least one saturated carbocyclic
ring therein. The saturated carbocyclic rings may be substituted
with one or more members of the group consisting of hydrogen,
C.sub.1-10alkyl, halogen, hydroxyl, C.sub.1-10alkoxycarbonyl,
C.sub.1-10alkoxy, cyano, amido, imido, silyl, and substituted
C.sub.1-10alkyl where the substituents are selected from one or
more members of the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido,
and silyl. Examples of alicyclic monomers include but are not
limited to polymerizable cyclobutanes, cyclopentanes, cyclohexanes,
cycloheptanes, cyclooctanes, biscyclobutanes, biscyclopentanes,
biscyclohexanes, biscycloheptanes, biscyclooctanes, and
norbornanes. It is preferred that the at least two alicyclic
monomers be polymerized by ring opening metathesis followed by
hydrogenation. Since co-polymers are costly, it is preferable that
the molds made from these co-polymers may be used several times to
prepare lenses instead of once which is typical. For the preferred
molds of the invention, they may be used more than once to produce
lenses.
[0010] More particularly, examples of alicyclic monomer containing
saturated carbocyclic rings include but are not limited to the
following structures 1
[0011] wherein R.sup.1.sup..sub.--.sup.6 are independently selected
from one or more members of the group consisting of hydrogen,
C.sub.1-10alkyl, halogen, hydroxyl, C.sub.1-10alkoxycarbonyl,
C.sub.1-10alkoxy, cyano, amido, imido, silyl, and substituted
C.sub.1-10alkyl where the substituents selected from one or more
members of the group consisting of halogen, hydroxyl,
C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido, imido and
silyl. Further two or more of R.sup.1-6 may be taken together to
form an unsaturated bond, a carbocyclic ring, a carbocyclic ring
containing one or more unsaturated bonds, or an aromatic ring. The
preferred R.sup.1-6 is selected from the group consisting of
C.sub.1-10alkyl and substituted C.sub.1-10alkyl where the
substituents are selected from the group consisting of halogen,
hydroxyl, C.sub.1-10alkoxycarbonyl, C.sub.1-10alkoxy, cyano, amido,
imido and silyl.
[0012] The alicyclic co-polymers consist of at least two different
alicyclic monomers. The preferred alicyclic co-polymers contain two
or three different alicyclic monomers, selected from the group
consisting of 2
[0013] The particularly preferred alicyclic co-polymer contains two
different alicyclic momoners where the generic structure of the
saturated carbocyclic rings of the alicyclic monomers are of the
formula 3
[0014] and R.sup.1-R.sup.4 are C.sub.1-10alkyl.
[0015] Typically the surface energy of the alicyclic co-polymer is
between 30 and 45 dynes/cm at 25.degree. C. The more particularly
preferred alicyclic co-polymer contains two different alicyclic
monomers and is sold by Zeon Chemicals L.P. under the tradename
ZEONOR. There are several different grades of ZEONOR, having of
glass transition temperatures form 105-160.degree. C. The
particularly preferred ZEONOR, is ZEONOR 1060R, which according the
to the manufacturer, ZEON Chemicals L.P. has an melt flow rate
("MFR") range of 11.0 grams/10 minutes to 18.0 grams/10 minutes (as
tested JISK 6719 (230.degree. C.)), a specific gravity (H.sub.2O=1)
of 1.01 and a glass transition temperature of 105.degree. C.
[0016] As used here, the term "mold" refers to a rigid object that
may be used to form lenses from uncured formulations. The preferred
molds are two part molds as described above, where either the front
curve or the back curve of the mold is made of the alicyclic
co-polymers of the invention and the other curve is made of
polypropylene. Examples of polypropylene include but are not
limited to metallocene catalyzed polypropylene that is nucleated
and clarified, such as but not limited to Achieve 1615 from Exxon
and ATOFINA EOD 00-11. The preferred method of making the molds of
the invention is by injection molding using known techniques, but
the molds could be made by other techniques lathing, diamond
turning, or laser cutting.
[0017] Typically lenses are formed on at least one surface of both
mold parts. However, if need be one surface of the lenses may be
formed from a mold and the other surface could be formed using a
lathing method, or other methods.
[0018] Aside from the alicyclic co-polymers, the molds of the
invention may contain additives that facilitate the separation of
the lens forming surfaces, reduce the adhesion of the cured lens to
the molding surface, or both. For example additives such as metal
or ammonium salts of stearic acid, amide waxes, polyethylene or
polypropylene waxes, organic phosphate esters, glycerol esters or
alcohol esters may be added to alicyclic co-polymers prior to
curing said polymers to form a mold. Examples of such additives
include but are not limited to Dow Siloxane MB50-321 (a silicone
dispersion), Nurcrel 535 & 932 (ethylene-methacrylic acid
co-polymer resin Registry No. 25053-53-6), Erucamide (fatty acid
amide Registry No. 112-84-5), Oleamide (fatty acid amide Registry
No. 301-02-0), Mica (Registry No. 12001-26-2), Atmer 163 (fatty
alkyl diethanolamine Registry No. 107043-84-5), Pluronic
(polyoxypropylene-polyoxyethylene block co-polymer Registry No.
106392-12-5), Tetronic (alkyoxylated amine 110617-70-4), Flura
(Registry No. 7681494), calcium stearate, zinc stearate,
Super-Floss anti block (slip/anti blocking agent, Registry No.
61790-53-2), Zeospheres anti-block (slip/anti blocking agent);
Ampacet 40604 (fatty acid amide), Kemamide (fatty acid amide),
Licowax fatty acid amide, Hypermer B246SF, XNAP, polyethylene
glycol monolaurate (anti-stat) epoxidized soy bean oil, talc
(hydrated Magnsium silicate), calcium carbonate, behenic acid,
pentaerythritol tetrastearate, succinic acid, epolene E43-Wax,
methyl cellulose, cocamide (anti-blocking agent Registry No.
61789-19-3), poly vinyl pyrrolidinone (360,000 MW) and the
additives disclosed in U.S. Pat. No. 5,690,865 which is hereby
incorporated by reference in its entirety. The preferred additives
are polyvinyl pyrrolidinone, zinc stearate and glycerol mono
stearate, where a weight percentage of additives based upon the
total weight of the polymers is about 0.05 to about 10.0 weight
percent, preferably about 0.05 to about 3.0, most preferably about
2.0 weight percent.
[0019] In addition to additives, the separation of the lens forming
surfaces may be facilitated by applying surfactants to the lens
forming surfaces. Examples of suitable surfactants include Tween
surfactants, particularly Tween 80 as described in U.S. Pat. No.
5,837,314 which is hereby incorporated by reference in its
entirety. Other examples of surfactants are disclosed in U.S. Pat.
No. 5,264,161 which is hereby incorporated by reference in its
entirety.
[0020] Still further, in addition to the alicyclic co-polymers, the
molds of the invention may contain other polymers such as
polypropylene, polyethylene, polystyrene, polymethyl methacrylate,
and modified polyolefins containing an alicyclic moiety in the main
chain. For example, a blend of the alicyclic co-polymers and
polypropylene (metallocene catalyst process with nucleation, where
ATOFINA EOD 00-11) may be used, where the ratio by weight
percentage of alicyclic co-polymer to polypropylene ranges from
about 99:1, to about 20:80 respectively. This blend can be used on
either or both mold halves, where it is preferred that this blend
is used on the back curve and the front curve consists of the
alicyclic co-polymers.
[0021] Further this invention includes a method of making a lens
comprising, consisting essentially of, or consisting of 1)
dispensing an uncured lens formulation onto a mold surface
comprising, consisting essentially of, or consisting of, an
alicyclic co-polymer wherein said alicyclic co-polymer comprises,
consists essentially of, or consists of at least two alicyclic
monomers of different chemical structures, and 2) curing said lens
formulation under suitable conditions. The terms lenses, alicyclic
monomers, and molds have their aforementioned meaning and preferred
ranges.
[0022] As used herein, the term "uncured" refers to the physical
state of a lens formulation prior to final curing to form a lens.
Some lens formulations contain mixtures of monomers which are cured
only once. Other lens formulations contain monomers, partially
cured monomers, macromers and other components. For examples of
such partially cured formulations are disclosed in U.S. Pat. Nos.
U.S. Pat. Nos. 6,419,858; 6,308,314; and 6,416,690. This invention
will be useful these formulations among others.
[0023] As used herein, the phrase "curing under suitable
conditions" refers to any of the known methods of curing lens
formulations, such as using light, heat, and the appropriate
catalysts to produce a cured lens. Examples of such curing
conditions may be found in the soft lens formulation references
listed herein.
[0024] Still further, the invention includes a lens produced by a
method comprising, consisting essentially of, or consisting of 1)
dispensing an uncured lens formulation onto a surface of a mold
comprising, consisting essentially of, or consisting of, an
alicyclic co-polymer wherein said alicyclic co-polymer comprises,
consists essentially of, or consists of at least two alicyclic
monomers of different chemical structures and 2) curing said lens
formulation under suitable conditions. The terms lens, alicyclic
monomers, uncured, and molds have their aforementioned meaning and
preferred ranges.
[0025] Yet still further, the invention includes a mold comprising,
consisting essentially of, or consisting of, an alicyclic
co-polymer and at least one lens forming surface
[0026] wherein said alicyclic co-polymer comprises, consists
essentially of, or
[0027] consists of at least two alicyclic monomers of different
chemical structures, and
[0028] wherein said at least one lens forming surface comprises,
consists essentially of, or consists of a coating effective amount
of a high molecular weight coating composition.
[0029] The terms lens, alicyclic monomers, uncured, and molds have
their aforementioned meaning and preferred ranges.
[0030] As used herein "lens forming surface" means the surface that
is used to mold the lens. Such surface has an optical quality
surface finish, meaning that it is sufficiently smooth so that a
lens surface formed by the polymerization of a lens forming
material in contact with the molding surface is optically
acceptable. Further said surface has a geometry that is necessary
to impart to the lens surface the desired optical characteristics,
including without limitation, spherical aspherical and cylinder
power, wave front aberration correction, corneal topography
correction and the like as well as combinations thereof.
[0031] The term "high molecular weight" means an average molecular
weight ("MW") sufficiently high so as to avoid dissolution of the
coating into the lens formulation or the mold material. For
purposes of the invention, preferably the molecular weight is
determined using gel permeation chromatography ("GPC") with a light
scattering detector and a high sensitivity refractive index
detector, for example model PL-RI available from Polymer Labs. The
GPC is performed using a phenogel 5 .mu.m linear column equipped
with a guard column of the same components and a solution of 0.5
weight percent lithium bromide in dimethyl formamide as the eluent.
Flow rates are 0.5 mL per minute with injection volumes from about
10 to about 20 .mu.L. The precise MW used will depend upon the
coating selected and the monomer mixture used. In a preferred
embodiment, the MW of the coating is greater than about 300 kD.
[0032] "Coating compositions" useful in this invention include a
wide variety of known monomers and polymers. Preferred are
poly(vinyl alcohol), polyethylene oxide, poly(2-hydroxyethyl
methacrylate), poly(methyl methacrylate), poly(acrylic acid),
poly(methacrylic acid), poly(maleic acid), poly(itaconic acid),
poly(acrylamide), poly(methacrylamide), poly(dimethylacrylamide),
poly(glycerol methacrylate), polystyrene sulfonic acid,
polysulfonate polymers, poly(vinyl pyrrolidone), carboxymethylated
polymers, such as carboxymethylcellulose, polysaccharides, glucose
amino glycans, polylactic acid, polyglycolic acid, block or random
copolymers of the aforementioned, and the like, and mixtures
thereof. Preferably, poly(2-hydroxyethyl methacrylate), poly(vinyl
pyrrolidone), poly(acrylic acid), poly(methacrylic acid),
poly(meth)acrylamide, or poly(acrylamide) is used. More preferably,
poly(2-hydroxyethyl methacrylate) is used.
[0033] Aside from the high molecular weight polymers, the coating
composition may include a low boiling point (less than about
100.degree. C.) solvent and a high boiling point, (greater than
about 100.degree. C.) solvent. Suitable low boiling solvents
include, without limitation, acetone, chloroform, and alcohols such
as methanol, ethanol, isopropanol, tert-butanol, and the like.
Useful high boiling solvents include, without limitation, methyl-,
ethyl-, and isopropyl lactate, ethylene and (poly)ethylene glycol,
propylene glycol, n-methylpyrrolidone, dimethyl formamide,
tetrahydrogeraniol, 1-butanol, 1-pentanol, 1-hexanol, 1-octanol,
3-methyl-3-pentanol, dimethyl-3-octanol, 3-methoxy-1-butanol, 1,2
and 1, 4-butanediol, 1,3-hexanediol, water, and the like.
Typically, the ratio of the low to high boiling solvent will be
about 10:90 to 90:10 when coating between 15 and 45 degrees C. When
the coating composition is applied using spin coating (discussed
below), the coating composition contains either or both low boiling
and high boiling solvents.
[0034] Additionally, the coating composition may include at least
one surfactant. Suitable surfactants include, without limitation,
anionic surfactants, such as carboxylic acid salts, sulfonic acid
salts, sulfuric acid salts, phosphoric and polyphosphoric acid
esters, cationic surfactants, such as long chain amines and their
salts, diamines and polyamines and their salts, quarternary
ammonium salts, amine oxides, nonionic surfactants, such as
polyoxyethylenated alkylphenols, alkyl phenol ethoxylates,
polyoxyethylenated straight chain alcohols, polyethoxylated
polyoxypropylene glycols, polyethoxylated polydimethylsiloxane
copolymers, fluorinated alkane ethoxylate copolymers, and long
chain carboxylic acid esters, zwitterionic surfactants, such as
pH-sensitive and pH insensitive surfactants, and the like, and
combinations thereof. The specific type and amount of surfactants
used will depend upon the other components of the coating
composition and the molding surface used. Typically, greater than
or equal to about 0.001 weight percent and less than or equal to
about 5 weight percent based on the total weight of the coating
composition will be used.
[0035] The coating composition may be applied to the molding
surface by any suitable method including, but not limited to,
compression, swabbing, spray coating, ink jet printing,
aerosolization, nebulization, dip coating, spin coating, and the
like and combinations thereof. Preferably, spin coating is used.
Also, preferably, the coating is dried, or rendered non-tacky,
prior to its use for forming lenses. Drying may be carried out
using any suitable method, but preferably is carried out at
temperatures up to about the glass transition temperature ("Tg") of
the mold material in air or under vacuum followed by equilibration
under a blanket of nitrogen at any temperature up to about the Tg
of the mold material. During the vacuum exposure process, cold
traps or other filters preferably are used to prevent contamination
of the mold.
[0036] In a spin coating method, the coating composition preferably
has a lower surface tension than that of the molding surface's
surface energy. More preferably, the surface tension of the coating
composition is greater than about 3 dynes/cm below that of the
surface energy of the molding surface to which it is applied when
measured at the coating application temperature. Most preferably,
the surface tension of the coating composition is more than 8
dynes/cm below that of the surface energy of the molding
surface.
[0037] In a preferred spin coating method for use in forming
contact lenses, spin coating is used to deposit a coating of a dry
thickness of about 5 to about 70 nm onto a molding surface of a
mold. If the surface tension of the coating differs from the
surface energy of the mold by greater than about 8 dynes/cm when
measured at the coating application temperature, a suitable spin
profile of at least about 6,000 and no more than about 8,000 RPM
using at least about 2 and no more than about 20 .mu.l of coating
composition and spinning for at least about 3 sec. If the surface
tension difference is less than about 8 dynes/cm, the mold is spun
up to at least about 3,000 and no more than about 5,000 RPM using
at least about 2 and no more than about 10 .mu.l of coating
composition and then the mold is spun up to at least about 7,000
and more than about 10,000 RPM for at least about 3 seconds prior
to stopping.
[0038] Any excess coating accumulating at the mold edges must be
removed and removal may be carried out by any convenient method
including, without limitation, swabbing the excess, removing the
excess using vacuum, solvent, washing or pressurized air jet.
Preferably, the excess is removed using an air jet. In using the
air-jet, it is critical that spinning is started prior to the jet
being turned on and, preferably, the air jet pressure is equal to
or greater than about 3 psi.
[0039] The term "coating effective amount" refers to the thickness
and the roughness of the coating composition on the lens forming
surface. For hydrated contact lenses, preferably a peak-to-peak
surface roughness of the hydrated lens is less than about 500 nm is
preferable. Thus, by coating effective amount is meant an amount of
the coating composition sufficient to provide a dry film thickness
of the coating composition on the lens forming surface that will
result in a hydrated article with an acceptable surface roughness
and for contact lenses preferably a hydrated lens peak-to-peak
surface roughness of less than about 500 nm. More preferably, the
amount of coating composition used is an amount sufficient to
produce a dry film thickness of at least about 5 nm and no more
than about 70 nm, preferably at least about 5 nm and no more than
about 50 nm, more preferably at least about 20 nm and no more than
about 40 nm. Still more preferably said coating effective amount
covers the entire or substantially the entire lens forming
surface.
[0040] Coating additives may be added to the high molecular weight
coating compositions of the invention. Coating additives may
include but are not limited to tints, pigments, and antimicrobial
compositions. Examples of antimicrobial compositions that may be
used in this manner are disclosed in the following U.S. patents and
applications which are hereby incorporated by reference in their
entirety, U.S. Pat. Nos. 6,218,492; 6,248,811; 6,160,056 and U.S.
patent application Ser. Nos. 10/028,400 filed on Dec. 20, 2001,
entitled Antimicrobial Contact Lenses and Methods for Their
Production; and 10/029,526, filed on Dec. 21, 2001, entitled
Antimicrobial Contact Lenses and Methods of Use.
[0041] Still, yet further, the invention includes a method for
making a coated lenses comprising, consisting essentially of, or
consisting of
[0042] (1) coating at least one lens forming surface of a lens mold
with a coating effective amount of a high molecular weight coating
composition wherein said lens mold comprises an alicyclic
co-polymer and at least one lens forming surface;
[0043] wherein said alicyclic co-polymer comprises, consists
essentially of, or
[0044] consists of at least two alicyclic monomers of different
chemical structures;
[0045] (2) dispensing an uncured lens formulation onto said at
least one lens forming surface; and
[0046] (3) curing said lens formulation and said coating
composition using a dwell time of less than about 5 minutes and
under conditions suitable to form a coated lens.
[0047] The terms lens, alicyclic monomers, uncured, molds, high
molecular weight, coating composition, and coating effective amount
all have their aforementioned meaning and preferred ranges.
[0048] In order to illustrate the invention the following examples
are included. These examples do not limit the invention. They are
meant only to suggest a method of practicing the invention. Those
knowledgeable in the production of lenses as well as other
specialties may find other methods of practicing the invention.
However, those methods are deemed to be within the scope of this
invention.
EXAMPLES
[0049] In the examples, the following abbreviations are used:
[0050] BC back curve
[0051] Blue-HEMA product of the base-promoted displacement of one
chloride of Reactive Blue # 4 dye by hydroxyethyl methacrylate.
[0052] CIP Pre-Cure
[0053] CGI 1850 1:1 (wt) blend of 1-hydroxycyclohexyl phenyl ketone
and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine
oxide
[0054] CGI 819 Bis (2,4,6-trimethylbenzolyl)phenyl phosphine
oxide
[0055] D3O 3,7-dimethyl-3-octanol
[0056] Darocur 1173 UV photo initiator Ciba Speciality
Chemicals
[0057] DMA N,N-dimethylacrylamide
[0058] FC front curve
[0059] ATOFINA EOD 00-11 A metallocene and isotactic polypropylene
having a melt flow of 14-18 g/10 minutes, ASTM Dl 238
[0060] HEMA 2-hydroxyethyl methacrylate
[0061] IPA isopropanol
[0062] Macromer 2 the reaction product of described in the examples
of U.S. patent application Ser. No. 10/028,400 filed on Dec. 20,
2001 and entitled Antimicrobial Contact Lenses and Methods for
Their Production
[0063] mPDMS monomethacryloxypropyl terminated
polydimethylsiloxane
[0064] m-PDMS-OH mono-(3-methacryloxy-2-hydroxypropyloxy)propyl
terminated, mono-butyl terminated polydimethylsiloxane (MW
1100)
[0065] Norbloc
2-(2'-hydroxy-5-methacrylyloxyethylphenyl)-2H-benzotriazole
[0066] PVP poly(N-vinyl pyrrolidone)
[0067] poly-Hema poly hydroxy ethylmethacylate having a molecular
weight of greater than 1 MM Dalton
[0068] SIGMA 2-propenoic acid,
2-methyl-,2-hydroxy-3-[3-[1,3,3,3-tetrameth-
yl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy]propyl ester
[0069] TEGDMA tetraethyleneglycol dimethacrylate
[0070] TrEGDMA triethyleneglycol dimethacrylate
[0071] TBACB tetrabutyl ammonium-m-chlorobenzoate
[0072] THF tetrahydrofuran
[0073] TMI 3-isopropenyl-.alpha.,.alpha.-dimethylbenzyl
isocyanate
[0074] TRIS 3-methacryloxypropyltris (trimethylsiloxy) silane
Example 1
Preparation of Molds with Alicyclic Co-Polymers
[0075] Pellets of the alicyclic co-polymer ZEONOR.RTM. 1060R were
placed in a de-humidifying dryer at 90.degree. C. for approximately
one to four (1-4) hours. The material was subsequently heated and
purged through an injection molding machine using the techniques
generally described in INJECTION MOLDING HANDBOOK, edited by
Dominick & Donald Rosato, Published by Nan Nostrand Reinhold
Company, 1986. Approximately three (3) pounds of material was
purged and molded within 10-15 minutes to give front curves and
back curves for lenses having a power of -1.00 D. Normal usable
lens molds were recovered and used to make lenses following the
procedure of Example 2.
Example 2
[0076] The formulation listed in Table A was used to prepare
silicone hydrogel lenses. Further details on the precise mixing
procedure is disclosed in U.S. patent application Ser. No.
09/957,299 filed on Sep. 20, 2001.
1 TABLE A Weight Percent Macromer 2 17.98 TRIS 14.00 DMA 26.00
MPDMS 28.00 TEGDMA 1.00 HEMA 5.00 PVP 5.00 NORBLOC 2.00 Blue HEMA
0.02 CGI 1850 1.00
[0077] The remainder of the formulation were additives and
diluents. The monomer to diluent ratio was 100:20, the diluent
being 3,7-dimethyl-3-octanol. Acetic acid, 1% of the final mix, was
used to stabilize the monomer.
[0078] The front and back curve molds prepared by the method of
Example 1 were coated with a high MW poly-HEMA coating.
Approximately 6 microliters of a 1.3% wt percent solution of
poly-HEMA in 70:30 ethanol:ethyl lactate was applied onto the front
curve mold surface (concave) by spin coating at 8000 rpm for 8 sec.
A jet of air was applied to the edge of the spinning part during
the last two seconds of the spin cycle to remove the excess
coating. Approximately 8.5 microliters of a 1.1% solution of
poly-HEMA in 70:30 ethanol:ethyl lactate was applied to the back
curve mold surface (convex) by spin coating at 6000 rpm for 2 sec
followed by 6 sec at 8000 rpm. A jet of air was applied to the edge
of the spinning part during the last two seconds of the spin cycle
to remove the excess coating. Lenses were made by dispensing the
above lens formulation into the lens molds, closing the parts,
precuring under visible lights for 45 sec at 45.degree. C. followed
by approximately 7 minutes of cure under visible lights at
70.degree. C. In all cases the precure was begun within 30 sec of
lens monomer dose into the mold.
[0079] The lenses were tested clinically and were found to be
equivalent in on-eye wettability, or tear break-up time, and
deposition resistance to ACUVUE.RTM. etafilcon A lenses
demonstrating that application of the coating to the lens results
in a physiological compatible lens.
Example 3
Preparation of Polypropylene Lens Molds
[0080] The FC and BC of lens molds were prepared using the method
of Example 1 and substituting polypropylene (manufactured by
Atofina EOD 00-11) for the alicyclic co-polymer of Example 1.
Example 4
Preparation of Lenses Using the Molds of Example 3
[0081] Lenses were made using the formulation and method of Example
2, but substituting the molds of Example 3, for the molds of
Example 1. The finished lenses were examined for defects in the
coating using a visual inspection apparatus. Defects were discrete
areas on the surface of the finished lens where the coating was not
applied. The percentage of defects was calculated and recorded in
Table B, below. This example demonstrates that molds made from
alicyclic co-polymers may be used to produce coated lenses with
significantly reduced coating defects.
2TABLE B Mold Material Number of for the FC Lenses Coating Defect
and BC Examined Rate Example 3 1200 39.1% Example 3 1200 45.5%
Example 3 1200 50.0% Example 1 1600 2.0% Example 1 1600 6.3%
Example 1 4800 4.4% Example 1 400 0.3%
Example 5
Lenses Prepared With Different Mold Materials for the FC and BC
[0082] FC and BC molds made by the method of Examples 1 and 3 were
used to prepare lenses by the method of Example 2. Dissimilar mold
materials were used to make some lenses as per Table C. The coating
defect rate was measured as well as the haze The haze values
indicated were measured by placing test lenses in saline in a clear
cell above a black background, illuminating from below with a fiber
optic lamp at an angle 660 normal to the lens cell, and capturing
an image of the lens from above with a video camera. The
background-subtracted scattered light image was quantitatively
analyzed, by integrating over the central 10 mm of the lens, and
then compared to a -1.00 diopter CSI Thin lens (commercial lens
made by Wesley Jessen 33 East Tower A, Des Planes, Ill.), which is
arbitrarily set at a haze value of 100, with no lens set as a haze
value of zero. This data shows that the lowest number of defects
are produced when the FC and the BC molds were made from an
alicyclic co-polymer.
3TABLE C CIP Coating Defect Haze FC Mold Material BC Mold Material
Time Rate (% CSI) ZEONOR ZEONOR 60 0.7% 24.7 ZEONOR ZEONOR 30 0%
20.5 ZEONOR PP 60 1.4% 31.2 ZEONOR PP 30 8.5% 53.8
Example 6
Preparation of Lens Molds from Alicyclic Polymer
[0083] Pellets of the alicyclic polymer Zeonex.RTM. 480R were
placed in a de-humidifying dryer at 100.degree. C. for
approximately four (4) hours. An attempt was made to form molds
using the method of Example 1. Usable lens molds could not be
formed with this material. Only tabs of cured materials were
recovered and the lens mold cavities were not formed. Increasing
the temperature of the molding machine (to the machine's maximum
safety level) and the temperature of the mold material did not
correct this problem. No usable molds were formed. This example
demonstrates the distinction between the successful production of
molds made from alicyclic co-polymers and the failure of molds made
from alicyclic polymers.
Example 7
Preparation of Blended Molds
[0084] An amount of polypropylene (ATOFINA EOD-0011, 50%) was
blended with Zeonor 1060 R (50%) in a mixing tumbler and processed
for 15 minutes. This mixture was processed in a extrusion or
palletizing process to generate a uniform material. The blended
material was placed into an injection molding machine and extruded
into male and female halves of a lens mold and subsequently cured.
The cured molds were placed into a nitrogen environment of 30
minutes before use.
Example 8
Preparation of Silicone Hydrogel Lenses B-
[0085] The reaction components and diluent (D30) listed in Table D
were mixed together with stirring or rolling for at least about 3
hours at about 23.degree. C., until all components were dissolved.
The reactive components are reported as weight percent of all
reactive components and the diluent is weight percent of final
reaction mixture. The reaction mixture was placed into the lens
molds of Example 7 and irradiated using Philips TL 20W/03T
fluorescent bulbs at 45.degree. C. under N2. The cure conditions in
a glove box are at approx 0.2 mW/c2 for about 6.5 minutes, followed
by 2.5 mWw/c2 for about 12 min. The oxygen level was <1.5% O2.
The molds were opened by hand the lenses were evaluated to
determine if the cured lenses remained with the front curve or the
back curve of the mold. Table E lists the percentage of Zeonor and
polypropylene (pp) in each lens mold half and the number of lenses
of Lens Type B which remained with either the front curve or the
back curve after they were separated.
4 TABLE D Lens Type Comp. B C D E F G H I J K SIGMA 28 30 28.6 28
31 32 29 39.4 20 68 PVP (K90) 7 10 7.1 7 7 7 6 6.7 3 7 DMA 24 17
24.5 23.5 20 20 24 16.4 37 22 mPDMS 31 32 0 31 31 34 31 29.8 15 0
TRIS 0 0 0 0 0 0 0 0 15 0 HEMA 6 6 6.1 6 6.5 3 5.5 2.9 8 0 Norbloc
2 2 0 2.0 2 2 2 1.9 0 0 CGI 1850 0.48 1 1.02 1 1 1 1 1 1 0 TEGDMA
1.5 2 1.02 1.5 1.5 1 1.5 1.9 0 2 TrEGDMA 0 0 0 0 0 0 0 0 1 0 Blue
HEMA 0.02 0 0 0 0 0 0 0 0 0 mPDMS-OH 0 0 31.6 0 0 0 0 0 0 0 Darocur
0 0 0 0 0 0 0 0 0 1 1173 D30% 23 26 17 23 23 29 32 28 17 27
[0086]
5TABLE E Back Curve Front Curve % lenses in FC Total No. Tested 5%
pp 100% Zeonor 29 24 95% Zeonor 25% pp 100% Zeonor 71 24 75% Zeonor
35% pp 100% Zeonor 88 24 65% Zeonor 35% pp 100% Zeonor 91 32 65%
Zeonor 40% pp 100% Zeonor 97 32 60% Zeonor 40% pp 100% Zeonor 100
24 60% Zeonor 45% pp 100% Zeonor 100 32 55% Zeonor 50% pp 100%
Zeonor 100 32 50% Zeonor 75% pp 100% Zeonor 100 32 25% Zeonor
[0087] This example illustrates that as the amount of polypropylene
in the blend increases, the lenses
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