Radiation imagery chemistry: process – composition – or product th – Imaging affecting physical property of radiation sensitive... – Making named article
Reexamination Certificate
2002-10-04
2003-06-17
McPherson, John A. (Department: 1756)
Radiation imagery chemistry: process, composition, or product th
Imaging affecting physical property of radiation sensitive...
Making named article
Reexamination Certificate
active
06579667
ABSTRACT:
FIELD OF INVENTION
The present invention relates to useful fluorinated compounds. More specifically, this invention relates to a family of fluorinated vinyl ether compounds, their uses, and the products resulting from their use.
BACKGROUND OF THE INVENTION
Vinyl ethers containing fluorine are of particular interest in coatings applications because they form polymers and copolymers that exhibit beneficial properties, including high chemical and thermal resistance, high electrical resistivity, low surface energy and low refractive index. These properties can be imparted to a coating surface and, consequently, fluorinated vinyl ethers are particularly useful in making protective release coatings, as well as, surfactants, anticorrosion agents, antioxidizing agents and the like.
Moreover, vinyl ether monomers or copolymers that can be cured via ultraviolet (UV) radiation offer even more advantages in coatings and other applications. Photocuring technology has grown rapidly within the last decade. The photocuring process involves the radiation induced polymerization or cross linking of monomers into a three dimensional network and has a number of advantages including the environmentally safe, solvent-free 100% conversion to a desired product, as well as short cycle times and limited space and capital equipment requirements.
In the telecommunications industry, for example, there is a need to develop photocurable compositions for optical wave guide and interconnect applications. In order to be useful in these applications, the photocurable compositions must polymerize to form polymers that are highly transparent at the working wavelength and possess low intrinsic absorption and scattering loss.
Unfortunately, in the near-infrared region, between 1330 and 1550 nm, many polymers formed from photocurable materials possess neither the required transparency nor low intrinsic absorption loss. There remains a need for new monomers that polymerize to form infrared-transparent polymers with low intrinsic absorption loss.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a family of fluorinated vinyl ether compounds which are useful for making other compounds, including polymeric compounds, having a wide variety of uses. The vinyl ether compounds of the present invention exhibit the beneficial properties of fluorinated monomers and can be utilized to realize the benefits of photocuring processes.
According to the present invention, fluorinated vinyl ether compounds are provided having the structure of Formula I:
R—O—X—O—CH═CH
2
(I)
wherein R is a radical having the formula: R
1
—CFH—CF
2
— or R
1
—CF═CF—, wherein R
1
is an unsubstituted or substituted aliphatic radical, an unsubstituted or substituted cyclic aliphatic radical, an unsubstituted or substituted aromatic radical, an unsubstituted or substituted araliphatic radical, or an unsubstituted or substituted heterocyclic radical; and X is an unsubstituted or substituted aliphatic radical, an unsubstituted or substituted cyclic aliphatic radical, an unsubstituted or substituted aromatic radical, an unsubstituted or substituted araliphatic radical, or a unsubstituted or substituted heterocyclic radical.
According to one aspect of the present invention, monomer compounds are provided having the structure of Formula I, provided, however, that when X is a substituted biphenyl radical, R
1
is not a trifluoromethyl group.
Another aspect of the present invention provides curable compositions that contain a curable component that includes at least one compound having the structure of Formula I, in which R and X are as described above for Formula I, and an initiator compound or a catalyst compound for the curable component. Preferred curable compositions include photocurable compositions combining at least one compound having the structure of Formula I and a photoinitiator compound. The curable component of the curable compositions of the present invention includes compounds of Formula I in which R
1
of R is a trifluoromethyl group when X is a substituted biphenyl radical.
The curable compositions of the present invention are useful in the manufacture of optical devices having light transmissive regions. Therefore, another aspect of the present invention provides a process for producing an optical device employing the steps of: (a) applying a layer of the photocurable composition of the invention onto a substrate; (b) imagewise exposing the photocurable composition of the invention to actinic radiation to form exposed and non-exposed areas on the substrate; and (c) removing the imagewise nonexposed areas while leaving the imagewise exposed areas on the substrate.
Yet another aspect of the invention comprises the light transmissive component of a waveguide produced in the above-identified process.
In the process of the present invention in which an optical device is produced, the fluorinated vinyl ether compounds of the present invention are cured by polymerization to form a polymeric coating on a substrate. The present invention therefore also includes the polymers produced by curing the fluorinated vinyl ether compounds of the present invention. Therefore, a further aspect of the invention provides a polymer with one or more vinyl ether repeating units having the structure of Formula II:
wherein R and X are as described above with respect to Formula I. The polymers of the present invention include polymers having vinyl ether repeating units in which R
1
of R is a trifluoromethyl group when X is a substituted biphenyl radical.
In Formulae I and II, X is preferably an unsubstituted or substituted C
1
-C
20
aliphatic radical, an unsubstituted or substituted C
3
-C
20
cyclic aliphatic radical, an unsubstituted or substituted C
6
-C
15
aromatic radical, an unsubstituted or substituted C
7
-C
13
araliphatic radical, or an unsubstituted or substituted 3-10 member heterocyclic radical. More preferably, X is an unsubstituted or substituted C
1
-C
20
alkyl radical, an unsubstituted or substituted C
3
-C
10
cycloalkyl radical, an unsubstituted or substituted 3-6 member heterocyclic radical, an unsubstituted or substituted C
6
-C
15
aryl radical, or an unsubstituted or substituted C
7
-C
13
aralkyl radical. The radicals may be substituted with essentially any conventional organic moiety. Examples of substitution groups include C
1
-C
6
aliphatics such as alkyls, halogenated alkyls, alkoxys, and alkenyls, C
6
-C
15
aryls, halogens, particularly fluorine, C
3
-C
8
cyclic aliphatics, nitros, aminos (primary and secondary), amidos, cyanos and hydroxyls.
X as a C
1
-C
20
alkyl radical may be straight chain or branched, for example, a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, or 2-ethylhexyl radical. Any of these groups may be substituted with typical organic moieties, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, methanesulphonyl, cyano, bromine, chlorine or fluorine to form, for example, methoxymethyl, 2-methoxyethyl, 2-ethoxy-methyl, 2-n-butoxyethyl, 3-methoxypropyl, 1-methoxybutyl, 2-methoxybutyl, methanesulphonylmethyl, 2-methanesulphonyl-ethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl, trichloromethyl, 2-chloroethyl, 2-(chloromethyl)ethyl, 2,2,2-trichloroethyl, 2-chloro-n-propyl or 3-chloro-n-butyl. In a preferred class of alkyl radicals, X is a straight chain C
2
-C
6
alkyl radical, especially an ethyl or butyl radical.
X as a C
3
-C
10
cycloalkyl radical may be, for example, a cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl dimethylcyclohexyl, cycloheptyl, or cyclooctyl radical. Any of these groups may be substituted with essentially any conventional organic radical, including, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, cyano, chlorine or fluorine. In a preferred class of cycloalkyl radical, X is a C
6
-C
10
cycloalkyl radical. In a preferred class of cycloalkyl radical, X is a C
6
-C
8
cycloalkyl radical, even more preferably, a cyclohexyldimethy
Bradley David E.
Nair Haridasan K.
Nalewajek David
Allied-Signal Inc.
Chess Deborah M.
McPherson John A.
Szuch Colleen
LandOfFree
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