Tinting optical substrates

Optical substrate dyeing The present invention relates to methods for coating optical substrates with a dyed or colored coating. The invention also relates to compositions which may be used to coat optical substrates such as tinted or tinted ophthalmic lenses, and to optical substrates that have been coated using the methods and / or compositions of the invention.

BACKGROUND OF THE INVENTION

Optically transparent resins are currently in widespread use for the manufacture of optical substrates such as spectacle lenses. These resins are advantageous in that they are lightweight, robust and easily processed.

For the manufacture of optical substrates both thermoplastic and thermosetting resins are used. Particular thermosetting resins that have been used include diethylene glycol bis (allyl carbonate) polymers such as CR-39 ™ (a trademark of PPG Industries) which provide optical substrates that have good transparency and thermal resistance and minimal chromatic aberration. Another advantage of these particular resins is that they are relatively easy to dye by introducing a dyeing agent into the resin. In the manufacture of eyeglass lenses it is fashionable to dye or pigment the lenses to give the lenses a colored tint.

A popular thermoplastic resin that is used in the manufacture of optical substrates is bisphenol A polycarbonate. This polycarbonate resin has good transparency, impact resistance and heat resistance, and has a relatively high refractive index. However, polycarbonates are more difficult to pigment than some of the aforementioned thermosetting resins such as CR-39.

A problem associated with both thermosetting and thermoplastic optical substrates, and especially with

5 1 599 554 / ΡΤ polycarbonate substrates, is its poor abrasion resistance. In order to overcome this poor abrasion resistance, abrasion resistant coatings (hard coatings) have been developed. Unfortunately, hard coatings are often non-dyeable.

One class of hard coatings is organosiloxane hard coatings. Organosiloxane coatings are often applied to thermosetting lens materials. However, it is found that the more abrasion resistant the organosiloxane coating is, the less dyeable it is. In general, organosiloxane resins cannot themselves be dyed. Instead, they act as a medium through which pigment molecules can pass. Therefore, regardless of whether the organosiloxane coating is tintable or not, it still requires the underlying substrate to be tintable.

Another class of hard coatings are acrylate based coatings. These coatings are often used to coat thermoplastics such as polycarbonate. Abrasion resistant acrylate coatings are also generally non-dyeable. So far, dyeable acrylate coatings have very poor abrasion resistance.

One method that can be used to apply a coating to thermosetting substrates is by coating within the mold. This involves applying a coating to a mold surface, partially curing the coating, assembling the mold parts, filling the mold with a substrate monomer and then curing the substrate as normal. A coated substrate is then removed from the assembly. In-mold coating is a very cost-effective way to coat an optical substrate. For optical substrates such as finished lenses, a coating must be applied to both the front and back of the lens. In order to tint a finished lens it is necessary to have a tintable coating applied to one or both surfaces. Unfortunately, until now there are no suitable known systems as a tintable coating within the mold.

ΕΡ 1,599,554 / ΡΤ

The present invention is intended to provide a method and / or composition for dyeing optical plastic substrates, including thermosetting polycarbonate optical substrates, which mitigates some of the problems with prior art methods and compositions.

Throughout this specification reference may be made to documents for the purpose of describing the background of the invention or for describing aspects of the invention. However, it is by no means accepted that any reference, including any patent or patent document, cited in this specification constitutes prior art. In particular, unless otherwise stated, it will be understood that reference herein to any document does not constitute an admission that any such document forms part of the common general knowledge of the art in Australia or in any other country. The discussion of references states what their authors claim, and the applicant reserves the right to challenge the accuracy and relevance of any of the documents cited herein.

US-A-5827923 discloses a composition that can be used to form a dyeable hard coating on a substrate. The composition contains: (A) colloidal silica; (B) an acrylate or methacrylate monomer which is capable of reacting with colloidal silica; (C) a monomer containing two or more acryloxy or methacryloxy groups; (D) a radical initiator; and (E) a dyeing additive.

SUMMARY OF THE INVENTION The present invention provides a method for dyeing an optical substrate according to claim 1.

The present invention also provides a coating composition which is suitable for forming an abrasion resistant dyeable coating layer on an optical substrate according to claim 23.

The present invention also provides a dyed optical substrate that is dyed according to the method of the invention.

ΕΡ 1,599,554 / ΡΤ

In a preferred aspect, the relative amounts of the abrasion resistant agent (y) as a w / w percentage of solids and the high crosslinking monomer (x) as a w / w percentage of monomers are between y = -0.75x + 60 ° C. y = -0.60x + 30, and more preferably between y = -0.67x + 50 and y = -0.60x + 30.

The optical substrate may be any substrate that functions to transmit or reflect light. Accordingly, the term includes optical articles such as ophthalmic lenses, and any other optical article that may require a tintable coating.

The method and composition of the present invention may be particularly suitable for dyeing optical substrates that are formed from an aromatic polycarbonate such as bisphenol A polycarbonate, although it is noted that the invention is not necessarily limited to that particular application.

The optical substrate coating step may involve applying the coating composition to a preformed optical substrate or may involve applying the coating during optical substrate formation, such as in an in-mold coating process.

The pretending compound may be one or more of the fixed pigments that are known in the art. Alternatively, the pretending compound may be one or more photochromic pigments.

Oxyalkylene units of the monomer having at least four contiguous oxyalkylene units may be oxyethylene units. The monomer may be a di (meth) acrylate monomer with a long chain polyoxyethylene backbone. As used herein the term (meth) acrylate refers to either an acrylate group or a methacrylate group. Also as used herein the term oxyalkylene refers to groups of formula - (CH 2)_no-O- where n is greater than or equal to two. Non-limiting examples of oxyalkylene groups include oxyethylene, oxypropylene and oxybutylene.

ΕΡ 1,599,554 / ΡΤ

In one form of the invention the abrasion resistant agent is an acrylated colloidal species such as colloidal silica, titanium dioxide, zirconium dioxide or other inorganic oxide. Most preferably, the abrasion resistant agent is acrylic colloidal silica which promotes adhesion durability and abrasion resistance of the coating.

BRIEF DESCRIPTION OF THE FIGURE The present invention will now be described with respect to various embodiments illustrated in the attached figure. However, it should be noted that the following description is not limited to the generality of the above description.

Figure 1 shows a graph of colloidal silica concentration vs. high cross-linking monomer concentration (tris [(2-acryloyloxy) ethyl] isocyanurate) and shows the effect of each concentration on the dyeing ability of the composition of the invention. Data for Figure 1 was obtained using a system in which the coating was cured under a nitrogen blanket.

DETAILED DESCRIPTION OF THE INVENTION

In a preferred form of the present invention the optical substrate is an ophthalmic lens. However, it will be appreciated that, to a broader extent, the invention is not limited thereto and the composition and methods may be used to coat any transparent optical substrate.

The coating composition of the invention includes a monomer having a polyoxyalkylene backbone containing at least four oxyalkylene units, an abrasion resistant agent and a high crosslinking monomer. The composition may be coated onto a preformed lens or onto a mold surface prior to casting a lens in a coating process within the mold. 0 Basic coating process within the mold is similar to that described in International Patent Application WOOl / 21375, which is incorporated herein solely for the purpose of exemplifying coating processes within the mold.

ΕΡ 1,599,554 / ΡΤ

The in-mold coating process typically involves coating the pouring face of a mold section with the composition of the invention, optionally in a suitable solvent. The composition can be applied by a variety of techniques including spraying, dipping, brushing, flow coating, spin coating and others.

partially or completely partial UV-initiated polymerization. The degree of polymerization may be controlled as described in WO1 / 21375.

The composition may then be cured, for example by

After coating the mold section with composition and partial curing and / or solvent removal, the mold parts are assembled together to form a coated mold cavity. The lens monomer is then poured into the mold and the plastic is cured in the usual manner.

A monomer having a polyoxyalkylene backbone containing at least four oxyalkylene units may be present in the coating composition in an amount of from about 10 to about 100 wt% of the total monomer (ie polyoxyalkylene monomer and high crosslinker monomer). The monomer having a polyoxyalkylene backbone containing at least four oxyalkylene units may be a long chain polyoxyethylene backbone monomer and is preferably a di (meth) acrylate monomer having a long chain polyoxyethylene backbone. Suitable polyoxyethylene di (meth) acrylates include polyethylene glycol di (meth) acrylate (200), polyethylene glycol di (meth) acrylate (400) and polyethylene glycol di (meth) acrylate (600).

The abrasion resistant agent is acrylic colloidal silica although other acrylic colloidal species such as titanium dioxide, zirconium dioxide or other inorganic oxides may also be used. Abrasion resistant agent promotes adhesion durability and abrasion resistance of the coating. Preferably, the acrylic colloidal silica does not contain any significant amounts of hexanediol diacrylate. Hexanediol diacrylate (HDDA) is commonly used as a dispersant in commercial preparations of acrylic colloidal silica. The amount of colloidal silica

Acrylate which is present in the composition may range up to about 70% (w / w solids) however, as described in more detail below, the amount used will depend on the amount of monomer composition.

high cross-linking that is present in the

As used herein, the term high crosslinked monomer refers to a monomer having a rigid main chain or a flexible main chain attached to a rigid core (such as an aromatic ring) where polymerization of the high crosslinked monomer provides a polymer. having a high level of abrasion resistance. The abrasion resistance level of the polymerized coating can be determined using standard tests, the details of which are provided in the examples provided herein.

The high cross-linking monomer may be tris [2 (meth) acryloyloxy] ethyl] isocyanurate, tris (2-hydroxyethyl) isocyanurate di (meth) acrylate, N, N ', N-tris (meth) acrylhexahydro- triazine, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tetra (meth) acrylate, tris (2hydroxyethyl) isocyanurate tri (meth) acrylate, trimethylolpropyl tri (meth) acrylate, hexa (meth) dipentaerythritol acrylate, 2,2,4,4,6,6hexahydro-2,2,4,4,6,6-hexachis (2 - ((2-methyl-1-oxo-2propenyl) oxy) ethoxy) -1,3 5,2,4,6-triazatriphosphorine, tetra-, penta- and hexa-functional urethane (meth) acrylates and tricyclodecanedimethanol di (meth) acrylate. High crosslinked monomers with polar central chains such as tris [2- (meth) acryloyloxy] ethyl] isocyanurate, and tris (2-hydroxyethyl) isocyanurate di (meth) acrylate and N, N ', N-tris (meth) acrylhex Hydro-s-triazine are most preferable as their polarity enhances the inherent pretending ability of the coating composition. The use of tris [2 (meth) acryloyloxy] ethyl] isocyanurate, and tris (2-hydroxyethyl) isocyanurate di (meth) acrylate and N, N ', N-tris (meth) acrylhexahydro-s-triazine in the composition Coating also enables the coated optical substrate to be finished with hard coatings.

The high crosslinked monomer may be present in the coating composition in an amount up to about 80%.

ΕΡ 1 599 554 / ΡΤ ρ / ρ of the total monomer (ie high cross-linking monomer and long chain polyoxyalkylene monomer). Again, the amount used will depend on the amount of abrasion resistant agent that is present in the composition.

The formulation regime for the coating composition is best represented by the diagram shown in Figure 1 and Equation (I). The filled regions of the chart represent the tintable region. The darker dashed region (^) represents the most preferable region in terms of pretending rate and property performance. The lighter dashed regions (® and ®) indicate similar property performance but lower pretense rates. The black region represents unacceptable abrasion resistance. The white region is the non-tintable region. From the diagram it can be seen that the preferred monomer ratio is dependent on the silica level. If the silica level is low, higher levels of tris [2acryloyloxy) ethyl] isocyanurate will be required. If the silica level is high, higher levels of polyethylene glycol di (meth) acrylate (400) are required.

When the data in Figure 1 are represented algebraically, the relative amounts of the abrasion resistant agent (y) as a w / w percent solids and the high crosslinking monomer (x) as the w / w percent monomers are between:

• y = -0.76x + 68 and y = -0.60x + 30 (ie the shaded area ^) • preferably between y = -0.75x + 60 and y = -0.60x + 30 (ie the shaded area);

And more preferably between y = -0.67x + 50 and y = -0.60x + 30 (ie the shaded area ^).

From the diagram shown in Figure 1, for an axial end, when no acrylic silica is present (although an abrasion resistant agent is required in the coating composition of the present invention), the weight percent tris [2- (acryloyloxy) ) ethyl] isocyanurate is preferably from about 50 to about 90%. Most preferably, when

99 1,599,554 / ΡΤ no acrylic silica is present (although an abrasion resistant agent is required in the coating composition of the present invention), the weight percentage of tris [2- (acryloyloxy) ethyl] isocyanurate is between about 50 and about 75%. For the other axial end, when tris [2- (acryloyloxy) ethyl] isocyanurate is not present (although a high cross-linking monomer is required in the coating composition of the present invention), the percent by weight of acrylic colloidal silica is preferably between about 30 and about 68%. Most preferably, when no tris [2- (acryloyloxy) ethyl] isocyanurate is present (although a high cross-linking monomer is required in the coating composition of the present invention), the weight percentage of acrylic colloidal silica is between about 30 and about 50%.

The coating layer that is formed provides good abrasion resistance. For example, using tris (2 (acryloyloxy) ethyl] isocyanurate and polyethylene glycol di (meth) acrylate (400) can achieve abrasion resistance that is up to 3 times more abrasion resistant in the standard Bayer test than uncoated CR-39. , and up to 20 times more abrasion resistant in the standard steel wool test than uncoated CR-39.

A key difference between a coating used as a coating within the mold compared to a coating used such as a polycarbonate coating is the solvent that is used with the coating composition. For in-mold coating, the choice of solvent is not critical. In the case of a polycarbonate coating, the choice of solvent is critical. When the method is used for pretending polycarbonate optical lenses the coating composition preferably includes a solvent to promote adhesion of the coating to the polycarbonate. If the solvent is not aggressive enough for the polycarbonate then the adhesion level of the coating to the polycarbonate lens substrate will not be sufficient. Alternatively, if the selected solvent is too aggressive then the coating will become cloudy. Suitable solvents include ketones such as methyl isobutyl ketone and esters such as

99 1,599,554 / de ethyl acetate. However, it may be necessary to moderate the aggressiveness of these solvents by the addition of an alcohol such as isopropanol or n-butanol.

Surprisingly, it was found that the selected solvent combination may have an influence on the pretense rate of the cured coating. Without being bound by theory one can speculate that solvent cage effects may affect the curing mechanism and thus affect the structure of the formed polymer matrix. In this regard, the use of esters has been found to be advantageous over ketones in terms of increasing the rate of incorporation of the pretense.

After a substrate lens has been coated with the composition of the invention preferably the composition is fully or partially cured. Preferably high intensity UV and / or high efficiency photoinitiators are used to overcome oxygen inhibition during polymerization of the coating composition. The optimal photoinitiator depends on the spectrum and intensity of the radiating light source. High intensity UV lamps available from Fusion Corporation and Xenon Corporation are suitable.

acyldithiocarbamates, dimethyldithiocarbamate; tribromacetophenone, phenylacetophenone,

Suitable photopolymerization initiators are acryloin and its derivatives, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and -methylbenzoin; diketones such as benzyl and diacetyl, etc .; organic sulphides such as diphenyl monosulphide, diphenyldisulphide, decylphenyl sulphide and tetramethylthiuron monosulphide; Stals such as S-benzoyl-N, Nphenones such as acetophenone,, -diethoxyacetophenone, -dimethoxy-nitro-, -tribromacetophenone benzophenone ep, p'-bis (dimethylamino) benzophenone; aromatic iodonium and aromatic sulfonium salts, sulfonyl halides such as p-toluenesulfonyl chloride, 1-naphthalenesulfonyl chloride, 2-naphthalenesulfonyl chloride, 1,3-benzenedisulfonyl chloride, 2,4dinitrobenzenesulfonyl bromide and pacetamidobenz chloride.

chloride of

ΕΡ 1,599,554 / ΡΤ

Although the choice of photoinitiator is not limited to any specific class, it must be taken into consideration that no residual color is given to the cured coating. Examples of commercially available photoinitiators include: Lucirin TPO, Irgacure 651, Irgacure 819, Irgacure 1800, Irgacure 500, Irgacure 907, Darocure 4043, Darocure 1664, Darocure 1116 and Vicure 55

Depending on the choice of photoinitiator and irradiation source, curing may or may not be necessary in an oxygen-free environment. However, if optimal sources of irradiation and photoinitiators are selected, the difference in performance between air-cured versus cured resins in a fully oxygen-free environment is marginal. Curing in an oxygen-free environment also broadens the choice of irradiation sources and photoinitiators.

If curing is performed in air, it may be necessary to increase the amount of abrasion resistant agent and / or high crosslinker monomer in order to obtain satisfactory abrasion resistance. For this reason the range of viable coatings that can be obtained with an oxygen-free curing system (eg a nitrogen blanket system) is larger than for an air curing system.

The composition may also be cured polymerized using thermal initiators. Such a primer may also need to be considered in an oxygen-free environment. The primer may be any suitable thermal primer known in the art. The nature of the initiator used in the composition depends on the ethylenically unsaturated material used. For example, for those ethylenically unsaturated materials undergoing free radical polymerization, suitable initiators are compounds which release or generate a free radical other than energy. These initiators include peroxide, azo and redox systems each of which is well known and described in the polymerization art.

EP 1 599 554

Included among the free radical initiators are conventional heat activated catalysts such as organic peroxides and organic hydroperoxides. Examples of such catalysts are benzoyl peroxide, tert-butyl perbenzoate, cumene hydroperoxide, azobis (isobutyronitrile) and others.

Suitable dyeing compounds include pigments that are typically used by optical laboratories, such as Brain Power Incorporated's BPI pigments, Inland's Perma Dyes, Cerium Optical Shades Lens Dyes typically involve dipping a lens into a heated solution (usually aqueous base) of dissolved pigments. However, there is an alternative dyeing procedure whereby the lenses may be immersed in a pigment solution which is subsequently heated in a microwave.

When photochromic, the coatings by the invention contain lens pigments, pigment molecules photochromic application together pigment are pigments can be incorporated into a second coating which upon the coating of the two with the two coatings is then heated to an elevated temperature to allow diffusion of photochromic pigments from the coating containing the photochromic pigment to the interior of the coating of this photochromic invention is original coating containing the pigment then removed leaving the coating of this invention now containing photochromic pigment. This process is commonly known as an imbibition process and is described in United States Patent 5,130,353.

The chemical nature of a coating resin required to accept pigment molecules is similar to that required to accept photochromic pigment molecules. However, in the case of photochromic pigments their incorporation within a coating is more problematic than with pigment molecules. Photochromic pigment molecules are larger and also require higher concentrations per unit volume of coating resin to be effective.

EP 1 599 554

Suitable photochromic pigments may be selected from one or more of the group consisting of anthraguinones, phthalocyanines, spiro-oxazins, chromos, pyranes and fulgidas.

Examples of preferred photochromic pigments may be selected from the group consisting of:

1,3-dihydrospiro [2H-anthra [2,3-d] imidazole-2,1'-cyclohexane] -5,10-dione,

1,3-dihydrospiro [2H-anthra [2,3-d] imidazole-2,1'-cyclohexane] -6,11-dione,

1,3-dihydro-4- (phenylthio) spiro [2H-anthra-1 ', 2-diimidazole2,1'-cyclohexane-6,11-dione,

1,3-dihydrospiro [2-H-anthra [1,2-d] imidazole-2,1'-cycloheptane] -6,11-dione,

1.3.3-trimethylpiroindole-2,3 '- [3H] naphtho [2,1-b] -1,4-oxazine, 2-methyl-3,3'-spiro-bi- [3H-naphtho [2,1 -bipiran] (2-Me),

2-phenyl-3-methyl-7-methoxy-8'-nitrospiro [4H-1-benzopyran-4,3 '[3H] -naphtho] 2,1-b] pyran, spiro [2H-1-benzopyran-2 9'-xanthene],

8-methoxy-1 ', 3'-dimethyl spiro (2H-1-benzopyran-2,2' - (1'H) guinoline,

2,2'-spiro-bi- [2H-1-benzopyran],

5'-amino-1 ', 3', 3'-trimethyl spiro [2H-1-benzopyran-2,2'indoline,

ethyl-methyl- (3 ', 3'-dimethyl-6-nitrospiro (2H-1-benzopyran-2,2'-indolin-1'-yl) propenoate, (1,3-propanediyl) bis [ 3 ', 3'-dimethyl-6-nitrospiro [2H-1-benzopyran-2,2'-indoline],

3,3'-dimethyl-6-nitrospiro [2H-1-benzopyran-2,2'benzoxazoline],

6'-methylthio-3,3'-dimethyl-8-methoxy-6-nitrospiro [2H-1benzopyran-2,2'-benzothiozoline], (1,2-ethanediyl) bis [8-methoxy-3-methyl -6-nitrospiro [2H-1benzopyran-2,2'-benzothiozoline],

N-N'-bis (3,3'-dimethyl-6-nitrospiro [2H-1-benzopyran-2,2 '(3'H) -benzothioazol-6'-yl) decanediamine], anhydride - (2,5-dimethyl Succinic -3-furyl) ethylidene (Z) ethylidene,

- (2,5-dimethyl-3-furyl) -1'-dimethylfluidide,

2,5-diphenyl-4- (2'-chlorophenyl) imidazole, (2 ', 4'-dinitrophenyl) methyl-1H-benzimidazole,

N, N-diethyl-2-phenyl-2H-phenanthro [9,10-d] imidazole-2-amine and

EP 1 599 554

2-nitro-3-aminofluoren-2-amino-4- (2'-furanyl) -6H-1,3-thiazine6-thione.

A method of imbibing photochromic pigments into a lens that is particularly suitable for the coating of this invention is as described in US Patent No. 5,130,353.

In order to provide a photochromic system of desired intensity, a sufficient amount of photochromic pigment must be present. If you want to soak a hard coated optical element with photochromic pigment or an easily unbeatable thin coating is applied over an easily unbeatable element or the easily unbeatable coating needs to be thick enough to accommodate a sufficient level of photochromic pigment. A coating depth of about 30 microns is generally required to be soaked. This easily unbeatable coating can be applied either through an in-mold coating process or through a conventional coating process.

DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION

Reference will now be made to examples embodying the above general principles of the present invention. However, it should be understood that the examples are preferred embodiments of the invention and that the following description is not intended to limit the generality of the above description.

Example 1

The following composition was used in a rotary coating process for a polycarbonate lens as described herein.

Acrylic colloidal silica is supplied as a concentrate in polyethylene glycol diacrylate (400). In the analysis the chemical constitution of the concentrate is as follows:

99 1 599 554 / ΡΤ (Silica content (Solid content of silica iIsopropanol (Methylisobutyl ketone (Water

56,6%

80,6%

10, 0% 7,1%

2,3%

Desired Final Resin Formulation:

[tris [2- (acryloyloxy) ethyl] isocyanurate (20% (w / w monomer))

<td>(di (meth) acrylate</td><td>of polyethylene glycol (400) (80%</td><td>(w / w monomer) (</td>

<td>(Colloidal Silica</td><td>acrylic (20%</td><td>(w / w solids) (</td>

<td>ilrgacure 651</td><td> [5%</td><td>(w / w solids) (1</td>

<td>ÍBYK 300</td><td> [0,8</td><td>% (w / w solids) (1</td>

<td>(Solids</td><td> [50%</td><td>(w / w) i</td>

<td>(Ethyl acetate</td><td>(plus residual solvent) * [50%</td><td>(w / w) [</td>

[* Solvent consists mainly of added ethyl acetate. (However, there is methyl isobutyl ketone, isopropanol and water] (residues present in the acrylic colloidal silica that will contribute) (to the final formulation. (I

Procedure

To a 200 ml beaker is added 22.0 g of polyethylene glycol (400) diacrylate, 7.4 g of tris [2 (acryloyloxy) ethyl] isocyanurate, 21.9 g of acrylic colloidal silica, 45.8 g of acetate ethyl, 0.4 g Byk 300 and 2.5 g benzophenone. Cover the beaker with aluminum foil to prevent UV dispersion from starting polymerization. This mixture will produce the following exact formulation:

<td>(tris [2- (acryloyloxy) ethyl] isocyanurate</td><td> [ 2 0 %</td><td>(p / p</td><td>in</td><td>monomer) (1</td>

<td>(polyethylene glycol diacrylate (400)</td><td> [ 8 0 %</td><td>(p / p</td><td>in</td><td>monomer) (1</td>

<td>((Acrylic Colloidal Silica</td><td>(i 20%</td><td>(p / p</td><td>in</td><td>solids) 1</td>

hrgacure 651 (5% (w / w solids)

ΕΡ 1,599,554 / ΡΤ (ΒΥΚ 300

0.8% (ρ / ρ solids)

<td>(Ethyl acetate</td><td>) 45.8% (w / w))</td>

<td>(Isopropanol</td><td>(2.2% (w / w))</td>

<td>Methylisobutyl ketone</td><td>(1.6% (w / w))</td>

<td>Water</td><td>(0.5% (w / w))</td>

<td>(Solids</td><td>(50% (w / w) (</td>

<td>The composition was applied a standard coating polycarbonate lens.</td><td>by rotating coating over using procedures of</td>

<td>Healing Mode</td><td></td>

<td colspan="2">The composition was cured by a 15 second exposure to a Fusion Corporation D lamp with a coating of nitrogen.</td>

<td>Dyeing Method</td><td></td>

<td colspan="2">100 ml BPI Black (from Brain Power Incorporated) is added to 1 liter of water, mixed and heated to 96 ° C. The lenses are immersed in the solution for a specified period of time and the transmission measured. This procedure is repeated periodically until the desired transmission is achieved. The total time the lens is in the dyeing solution is recorded.</td>

<td>properties</td><td></td>

<td>(Steel wool</td><td> (★★★★★</td>

<td>Bayer</td><td> (★★★★</td>

<td>(Time to reach 20% T</td><td>(10 minutes (</td>

Bayer and steel wool abrasion resistance scores are based on the abrasion resistance of a selected material relative to CR-39. Abrasion resistance is

ΕΡ 1 599 554 / ΡΤ quantified in terms of the amount of cloudiness developed when the lens is abraded. The higher the cloudiness level, the less abrasion resistant the lens is. Star rating is based on the relationship between the cloudiness level for a sample lens and the cloudiness level for an uncoated CR-39 lens. Star ratings are based on the following cloud ratios.

Steel wool abrasion resistance

<td colspan="3"> \&lt;0,5</td><td>none</td><td colspan="2">star</td>

<td> 0,5</td><td> 1,0</td><td></td><td> ★</td><td></td><td></td>

<td>of</td><td> 1,5</td><td></td><td> ★★</td><td></td><td></td>

<td> 1,5</td><td> 2,5</td><td></td><td> ★★★</td><td></td><td></td>

<td> 2,5</td><td> 10</td><td></td><td> ★★★★</td><td></td><td></td>

<td> &gt;10</td><td></td><td></td><td> ★★★★★</td><td></td><td></td>

<td colspan="2">Resistance</td><td colspan="2">to abrasion Bayer</td><td></td><td></td>

<td> &lt;0,5</td><td> —</td><td> —</td><td>none</td><td>star</td><td></td>

<td> 0,5</td><td> 1,0</td><td></td><td> ★</td><td></td><td></td>

<td> 1,0</td><td> 1,5</td><td></td><td> ★ ★</td><td></td><td></td>

<td>| l, 5</td><td> 2,5</td><td></td><td> ★ ★★</td><td></td><td></td>

<td> 2,5</td><td> 5</td><td></td><td> ★ ★★★</td><td></td><td></td>

<td> &gt;5</td><td></td><td></td><td> ★ ★★★★</td><td></td><td></td>

Example 2

The following composition was used in a rotary coating process for a polycarbonate lens as described herein.

<td>tris [2- (acryloyloxy) ethyl] isocyanurate</td><td>30% (w / w monomer)</td>

<td>polyethylene glycol diacrylate (400)</td><td>70% (w / w monomer)</td>

<td></td><td></td>

ΕΡ 1,599,554 / ΡΤ

<td>Acrylic colloidal silica Benzophenone</td><td>25% (w / w solids) 5% (w / w solids)</td>

<td>BYK 300</td><td>0.8% (w / w solids)</td>

<td></td><td></td>

<td>Solid Ethyl acetate (plus residual solvent)</td><td>50% (w / w) 50% (w / w)</td>

Healing mode

The composition was cured by a 15 second exposure to a Fusion Corporation D lamp.

properties

<td>(Steel wool</td><td> (★★★★ - ★★★★★</td>

<td>(Bayer</td><td> (★★★</td>

<td>(Time to reach 20% T</td><td>(40 min (</td>

<td>Example 3</td><td></td>

<td>The following composition was</td><td>used in a process of</td>

<td>rotary coating for a</td><td>polycarbonate lens as</td>

<td>described herein.</td><td></td>

<td colspan="2">(tris [2- (acryloyloxy) ethyl] isocyanurate (40% (w / w monomer))</td>

<td colspan="2">polyethylene glycol idiacrylate (400) (60% (w / w monomer) 3</td>

<td>(Acrylic Colloidal Silica</td><td>(20% (w / w solids))</td>

<td>(Benzophenone</td><td>(5% (w / w solids))</td>

<td>(BYK 300</td><td>(0.8% (w / w solids) (</td>

<td>(Solids</td><td>(50% (w / w) (</td>

(Ethyl acetate plus residual solvent (50% (w / w))

ΕΡ 1,599,554 / ΡΤ

Healing mode

15-second exposure to a Fusion Corporation D lamp in air.

properties

¡5 min steel wool ÍBayer jTime to reach 50% T

Example 4

The following composition was used in an in-mold coating process for a CR-39 lens as described above.

<td colspan="2">itris [2- (acryloyloxy) ethyl] isocyanurate</td><td rowspan="2">ho% ^ 80%</td><td colspan="2">(w / w monomer) i</td>

<td>polyethylene glycol idiacrylate</td><td> (400)</td><td>(w / w of</td><td>monomer) i</td>

<td>Acrylic colloidal silica</td><td></td><td> 12 0%</td><td>(w / w of</td><td>solid) i</td>

<td>Irgacure 651</td><td></td><td>B%</td><td>(w / w of</td><td>solid) i</td>

<td>: BYK 300</td><td> ...................................</td><td>H. 8th</td><td colspan="2">% (w / w solids) i</td>

<td>ISOLID</td><td> —</td><td>h4%</td><td>(w / w)</td><td></td>

<td>Methyl acetate plus solvent</td><td>residual</td><td> ^86%</td><td>(w / w)</td><td></td>

Healing mode

The composition was applied to the rear surface of a front mold and partially cured with a ~ 5 second exposure to a Fusion Corporation D lamp in air. The front and rear parts of the mold were assembled and the mold was filled with CR-39 monomer and thermally cured using standard procedures.

ΕΡ 1,599,554 / ΡΤ

properties

<td>Steel wool</td><td> ★★★★</td>

<td>Bayer</td><td> ★★★★</td>

<td>Time to reach 50% T</td><td>7 min</td>

<td>(Back surface covered)</td><td></td>

Example 5

The following composition was used in a spin coating process for a polycarbonate lens as described herein.

<td>polyethylene glycol diacrylate</td><td> (400)</td><td>[100% (w / w monomer)</td>

<td>Acrylic colloidal silica</td><td> —</td><td>[40% (w / w solids)</td>

<td>Irgacure 651</td><td></td><td>[5% (w / w solids)</td>

<td>[byk 300</td><td></td><td>[0.8% (w / w solids)</td>

<td>[Solids</td><td> —</td><td>[50% (w / w)</td>

<td>Ethyl acetate plus solvent</td><td>residual</td><td>[50% (w / w)</td>

Healing mode

15-second exposure to a Fusion Corporation D lamp in air.

properties

<td>Steel wool</td><td> [★★★★★</td>

<td>Bayer</td><td> [★★★</td>

<td>Time to reach 50% T</td><td>[10 min</td>

ΕΡ 1,599,554 / ΡΤ

Example 6

The following composition was used in a rotary coating process for a polycarbonate lens as described herein.

itris [2- (acryloyloxy) ethyl] isocyanurate | 70% (w / w monomer)

<td>polyethylene glycol diacrylate (400)</td><td>| 30% (w / w monomer) i</td>

<td></td><td>1 i</td>

<td>Acrylic colloidal silica</td><td>10% (w / w solids)</td>

<td>Irgacure 651</td><td>15% (w / w solids)</td>

<td>ÍBYK 300</td><td>10.8% (w / w solids)</td>

<td>Solid</td><td>150% (w / w)</td>

Ethyl acetate plus residual solvent

50% (w / w)

Healing mode

15-second exposure to a Fusion Corporation D lamp in air.

Steelblade Properties

ÍBayer

Time to reach 50% T ★★★★ ★★ min

Finally, there may be other variations and modifications made to the preparations and methods described herein that are also within the scope of the present invention.