Process for obtaining a photochromic latex

Details Process for obtaining a photochromic latex Process for obtaining a photochromic latex

2001-11-16

2004-08-03

Lee, Rip A. (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C524S833000, C524S853000, C524S089000, C524S110000, C524S104000, C524S095000

Reexamination Certificate

active

06770710

ABSTRACT:

This application claims priority to French Application No. 00/14903 filed 17 Nov. 2000.
The present invention relates in a general manner to a process for obtaining a photochromic latex, in particular for applications in the optical field and preferentially in ophthalmic optics.
As is well known, latexes are emulsions of polymers, in particular aqueous emulsions.
These latexes are prepared conventionally by polymerization of an emulsion of monomers.
Typically, the polymerization of an emulsion requires the use of at least one monomer or mixture of monomers, one surfactant or mixture of surfactants, and an initiator or primer of polymerization. The monomer or mixture of monomers is dispersed as droplets with the aid of the surfactant or mixture of surfactants and by means of stirring with high shearing. The droplets of monomer usually have a diameter of 1 to 10 &mgr;m.
The latex emulsions obtained by the conventional processes have the disadvantage of being unstable, lack reproducibility and show size variations of the particles.
In order to correct these disadvantages, it has been proposed to seed the monomer droplets with polymer particles of known size and concentration. The seed particles, when they are in contact with the monomer droplets, swell to an equilibrium size. Such a procedure is described in the patent U.S. Pat. No. 4,011,388.
Although this seeding technique enables the number and dimension of the particles to be precisely controlled, it depends on the rate and degree of swelling of the particles.
A process for obtaining latex has also been proposed in the patent U.S. Pat. No. 5,686,518 which consists of dissolving one or more polymers in an ethylenically unsaturated monomer or mixture of such monomers and of dispersing the polymer solution in the monomer in water and at least one surfactant to obtain a “miniemulsion”, the droplets of which have a mean diameter of 10 to 500 nm, then of polymerising the “miniemulsion” to obtain the final latex.
The use of miniemulsions for the emulsion polymerization is also described in the documents FR-2.785.904, EP-852-239, U.S. Pat. Nos. 5,569,716, 5,653,965 and WO-98/50436.
No document relates to the preparation of a photochromic latex.
The photochromic latexes are conventionally obtained by preparing a first solution containing the monomer(s) and the photochromic compound(s) and a second solution containing the dispersion medium, usually water and a surfactant, and by mixing the two solutions with vigorous stirring in order to obtain a pre-emulsion. The pre-emulsion is then transferred in one portion to a reactor and is degassed under nitrogen with stirring. At the end of the degassing the polymerization primer is introduced, usually dissolved in a solvent (typically water), and the polymerization is carried out by heating to obtain the latex.
The latex obtained is then coarsely filtered through cloth, then stored protected from light.
Such a process for obtaining a latex with photochromic properties is described in the document FR-2.790.264.
In addition to the problems of stability mentioned above, the photochromic latexes obtained by the conventional process show, during their synthesis, a considerable migration of the photochromic compound(s) into the aqueous phase, leading to a partial or complete degradation of the photochromic compounds in the final latex film. Consequently, the conventional processes require the use of considerable quantities of expensive photochromic compounds to compensate for these losses by migration.
Hence the purpose of the invention is to furnish a process for obtaining a photochromic latex which limits, even suppresses, the migration of the photochromic compounds into the aqueous phase of the latex during its synthesis.
According to the invention, the process for obtaining a photochromic latex comprises:
(1) the preparation of a mixture comprising at least one organic monomer Z with a C═C group, polymerizable by a radical process, at least one organic photochromic compound, at least one surfactant, water and optionally a polymerization primer;
(2) the treatment of the mixture obtained in step (1) in order to form a miniemulsion consisting of an organic phase dispersed in the form of droplets having a diameter of 50 to 500 nm, and preferably 50 to 300 nm, in an aqueous phase;
(3) the addition to the miniemulsion of a polymerization primer, if this latter was not introduced in step (1), or of a quantity of primer additional to that added in step (1);
(4) the polymerization of the reaction mixture obtained in step (3), and
(5) the recovery of the photochromic latex.
In a preferred embodiment of the process of the invention, a stabilization agent of the miniemulsion is added to the mixture in step (1).
Preferably, the mixture of step (1) is obtained by preparing separately a solution A containing the monomer(s), the photochromic compounds and, optionally, the stabilization agent(s) and a solution B containing water and the surfactant(s), then by combining the two solutions A and B.
The mixture of the two solutions A and B is then treated, for example by means of a microfluidiser in order to obtain a miniemulsion, the diameter of the droplets of the organic phase of which varies from 50 to 500 nm, preferably from 50 to 300 nm and typically is of the order of 200 nm.
The microfluidiser is a high pressure impact emulsifier. Such a microfluidiser is described in the patent U.S. Pat. No. 4,533,254 and is marketed by the Microfluidics Corporation company in Naston, Mass., USA. Another microfluidiser is sold by the Stansted Fluid Power company Ltd. Briefly, the apparatus consists of a high pressure pump and an interaction chamber where the emulsion is prepared. Usually, the mixture is passed once into the emulsifier at a pressure of 35 to 105 MPa.
The size of the droplets will vary as a function of the composition of the mixture, the pressure applied and the number of passes in the emulsifier.
Thus, with a pressure of 70 MPa, miniemulsions according to the invention were obtained having a droplet diameter of about 200 nm.
The miniemulsion can also be obtained with ultrasonic devices or mechanical stirrers of the Ultraturax™ type.
The miniemulsion obtained is then usually transferred directly to a reactor where it is degassed. This degassing is usually performed under nitrogen, with stirring and at a temperature that may vary from room temperature to 90° C., preferably at a temperature of 40 to 70° C.
Once the degassing is complete, one or more polymerization primers is/are added directly to this reactor and the polymerization of the monomer(s) is carried out with stirring and preferably at a temperature higher than room temperature, usually from 50 to 90° C.
Optionally, during polymerization a minor quantity, usually less than 10%, and preferably less than 5% by mass with respect to the mass of the initial Z monomer, of one or more other polymerizable monomers may be added dropwise in order, for example, to modify the mechanical properties of the latex particles.
The polymerization reaction is terminated when the dry extract content of the emulsion has stabilized.
At this stage it is possible to incorporate into the latex obtained, concomitantly with a polymerization primer, one or more other polymerizable monomers, for example acrylates or methacrylates to obtain a latex, the particles of which are of the core/shell type.
The latex obtained is recovered conventionally, for example by filtration through cloth.
Usually the polymer particles of the latex obtained have a diameter of 50 to 400 nm.
The Z monomers recommended are monomers of the alkyl (meth) acrylate type, preferably of the mono(meth) acrylate type.
The alkyl groups are preferably C
1
-C
10
alkyl groups, such as methyl, ethyl, propyl and butyl.
Of the preferred monomers the methyl, ethyl, propyl and butyl acrylates and methacrylates may be mentioned.
It is also possible to use mixtures of these monomers, in particular mixtures of C
2
-C
10
alkyl acrylate and C
1
-C
3
alkyl methacrylate monomers.
The organic photochromic compounds suit

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