Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From silicon reactant having at least one...
Reexamination Certificate
1998-11-18
2001-04-17
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From silicon reactant having at least one...
C528S018000, C528S034000, C428S447000, C427S387000, C427S164000, C106S287190, C106S287140
Reexamination Certificate
active
06218494
ABSTRACT:
BACKGROUND OF THE INVENTION
(1) Field of the Invention
The present invention relates in general to an abrasion-resistant coating composition, as well as to a process for making such a composition and articles, in particular optical articles such as ophtalmic lenses, comprising an abrasion-resistant coating including a cured layer of said abrasion-resistant coating composition.
(2) Description of the Prior Art
Numerous articles must be provided with abrasion-resistant or scratch resistant coatings since their sensitivity towards scratching does not allows them to be used in practice or allows only short periods of use.
This is in particular the case of optical articles such as ophtalmic lenses for which an abrasion-resistant or scratch-resistant surface is essential for maintaining a lens transparency over a period of time as long as possible.
The use of transparent plastic materials for making optical articles such as ophthalmic lenses is nowadays common pratice due to their unique lightness advantage compared to mineral glasses. Additionally, the use of such transparent plastic materials for making optical articles, in particular ophthalmic lenses, has allowed manufacturing articles having high refractive indices of 1.6 or more.
As a result of this achievement, it has been possible to manufacture lenses of lower thickness for an equivalent corrective power (optical power).
However, plastic materials in general, and more especially those employed in the manufacture of ophthalmic lenses, usually have poor mechanical surface characteristics with in particular low resistance to abrasion or scratching.
It is therefore a common practice to protect them with an abrasion-resistant or scratch-resistant coating.
Aqueous composition of organoalkoxisilanes and metal alkoxides have been proposed for making such abrasion and scratch-resistant coatings, as for example in U.S. Pat. Nos. 4,084,021; 4,746,366; 4,754,012; 4,814,017 and 5,357,024.
Although these prior art compositions impart abrasion and scratch resistance to plastic substrates coated therewith there is still a need, in particular in the field of ophthalmic lenses, to formulate abrasion and scratch-resistant coating compositions exhibiting higher abrasion and scratch-resistance properties.
Furthermore, with the present possibility of obtaining transparent plastic material substrates having a wide range of refractive indices, for example, from 1.45 to 1.65 and more, it would be of major interest to formulate abrasion and scratch-resistant coating compositions which would exhibit refractive indices matching such a wide range of refractive indices and in particular high refractive indices.
Increasing the amount of metal alkoxides, such as titanium and zirconium alkoxide in the aqueous compositions of organoalkoxysilanes of prior art would increase the refractive indices of resulting cured coatings. However, high contents of metal alkoxides in such coating compositions lead to stability problems of the formulated compositions. In particular, the metal alkoxides, when used in relatively high amounts in the coating compositions, have a pronounced tendency to precipitate and agglomerate, resulting in an non-homogeneous coating.
SUMMARY OF THE INVENTION
Thus, the aim of the present invention is to formulate an abrasion or scratch-resistant coating composition which, while remedying to the drawbacks of the prior art compositions, also exhibits improved abrasion and scratch-resistant properties.
The present invention also concerns a process for making such abrasion or scratch-resistant coating compositions.
The present invention further concerns optical articles, in particular optical lenses, coated with an abrasion or scratch-resistant coating including a cured layer of the abrasion or scratch-resistant coating composition.
According to the invention, there is provided an abrasion or scratch-resistant coating composition which comprises:
(A) a component which is the reaction product with oxalic acid of at least one organometallic compound of formula:
R
1
y
—M(OR)
x-y
(I)
wherein, M is a metal, R is H or an alkyl radical, R
1
is a chelating ligand, x is the valency of the metal, y is an integer at least equal to 1 and x-y is at least equal to 1; and
(B) at least one organoalkoxysilane of formula:
R
3
n
Si (OR
2
)
4-n
(II)
wherein, R
2
is an alkyl radical, R
3
is an epoxidized monovalent organic radical and n is an integer from 1 to 3;
or a mixture of the organoalkoxysilane of formula (II) with an alkoxysilane of formula (II′)
R′
n′
Si(OR″)
4-n′
(II′)
wherein
n′ is an integer from 0 to 3, preferably from 0 to 2 (included), and
R″ is H or an alkyl radical or alkoxyalkyl radical, preferably a C
1
-C
4
alkyl radical and R′ is a vinyl, (meth)acryl, aromatic, cyclic or aliphatic alkyl radical (preferably a C
1
-C
4
alkyl radical).
Preferred alkoxysilanes of formula (II′) are tetra(methoxy)silane, tetra(ethoxy)silane, methyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, vinyldimethoxysilane, vinyltriethoxysilane, (meth)acryloxypropyltrimethoxysilane, (meth ) acryloxypropyltriethoxysilane.
Preferably, component (B) comprises a major amount of the organoalkoxysilane of formula (II).
Optionally, the inventive coating composition may be a partial or total hydrolyzate of components (A) and (B).
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
In component (A) of the coating composition the metal is in general selected from the group consisting of Ti, Zr, Sc, Nb, V, Hf, Cr, Y, Al, Ge, Sn, Ta and W. Preferably the metal is Ti, Zr or Al and more preferably Ti or Zr.
R is preferably a C
1
-C
4
alkyl radical such as ethyl, propyl and butyl.
R
1
is preferably a ligand produced from a compound of formula L
1
COCH
2
COL
2
or L
3
COCH
2
COOL
4
, wherein L
1
, L
2
, L
3
and L
4
, are C
1
-C
10
alkyl groups, preferably C
1
-C
4
alkyl groups, and more preferably methyl and ethyl groups.
Among the preferred ligands represented by R
1
there may be cited acetylacetonate, aliphatic aceto acetate, acetoacetones, acetylacetones methylacetoacetate, and ethylacetoacetate, being the most preferred.
Preferably also, in formula (I), y is equal to 2.
Among the most preferred component (A) there may be cited the reaction products of oxalic acid with titanium bis(acetyl acetonato)diisopropoxide, zirconium bis(acetylacetonato) diisopropoxide, titanium (acetylacetonato)triisopropoxide and zirconium (acetylacetonato)triisopropoxide.
Component (A) of the compositions of the invention may be prepared by (1) mixing an organometallic compound of formula M(OR
2
)
4
(III), wherein M and R
2
are as defined above, with a ligand producing compound such as those defined above, at a temperature ranging from ambient temperature to 100° C. or more, and then (2) mixing to the reaction product of step (1) oxalic acid at ambient temperature.
Usually, a solvent is also used in step (2).
Among the appropriate solvents there may be cited methanol, ethanol, isopropanol, other aliphatic alcohols of low molecular weight, ethylacetate, methylethylketone and tetrahydropyrane.
Step (1) may last from 1 to 24 hours, depending upon the reacted compounds and the reaction temperature.
In step (1) the amount of ligand producing compound is determined in order to obtain a compound of formula (II) in which n is 1, 2 or 3, preferably 2.
Usually, there may be used 100 to 200 parts by weight of the ligand producing compound per 100 parts by weight of the starting tetraalkoxyde compound of formula (III).
Step (2) will typically last for 5 to 15 minutes.
The amount of oxalic acid used in step (2) usually ranges from 10 to 70, preferably 15 to 65 parts by weight based on 100 parts by weight of the starting tetraalkoxide compound of formula (III).
Nevertheless, an essential feature of the invention is that, in step (2), there is used at least an effective amount of oxalic acid, for example a molar ratio of 2 or more of oxalic acid based on compound of formula (I) and in
Dang Hoa Thien
Tatman Sheila
White, Jr. Sidney Shaw
Dawson Robert
Essilor International (Compagnie Generale d'Optique)
O'Keefe, Egan & Peterman
Zimmer Marc S.
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