Printing ink composition

Details Printing ink composition Printing ink composition

1999-08-02

2001-12-18

McPherson, John A. (Department: 1756)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031500, C106S031440, C523S160000

Reexamination Certificate

active

06331204

ABSTRACT:

This invention relates to processes for printing substrates, to a mixture of polymer precursor and dye, to a process for making optical filters, to optical filters and to navel dyes.
Published European Application No 546,856 proposes a process for making colour filters (for use e.g. in liquid crystal displays) which uses a photosensitive resin resist composition containing a dye which either has a photopolymerisable substituent or has a molecular weight in the range from 500 to 4000. The dye is said to be immobilised in the resin matrix either by its high molecular weight, or by self-polymerisation or by co-polymerisation of the dye with the photosensitive resist resin.
Published European Patent Application No. 531,106 proposes colour filters in which the light-filtering substance comprises the result of the reaction of a binder polymer with a reactive dye. The reactive groups in the binder polymer are hydroxy or amino groups, while the reactive dye is of cellulose-reactive type, containing either a vinylsulphone group (or a precursor thereof), or an electrophilic reactive group (e.g. a chlorine atom attached to a triazine ring), or a mixture of these types.
Published European Patent Application No. 564,237 proposes a process of making a colour filter using a photosetting resin precursor and a dyestuff which can uniformly colour the photocured resin.
U.S. Pat. No. 5,176,971 proposes a method of making a colour filter in which the filter picture elements (red, green and blue) are made of polyimide resin containing a dye.
U.S. Pat. No. 4,781,444 proposes a method of making a colour filter by electrodeposition of a coloured layer on a substrate. The coloured layer comprises a polymer having a dye chemically bonded to it. The dye used is a cellulose-reactive dye containing for example a vinyl sulphone group or an electrophilic reactive group (e.g. a chlorine atom attached to a triazine ring), as described above for European Patent Application 531,106.
U.S. Pat. No. 5,231,135 proposes a method of making a coloured polymer coating on a substrate, in which the coloured polymer is prepared by reaction of a colourant of formula R-[polymeric constituent-X]
n
wherein R is an organic dyestuff radical and X is a reactive moiety (e.g. —OH, —NH
2
, or —SH) with a linking agent (e.g. a polyisocyanate or a melamine-formaldehyde resin), which in turn reacts with a polymer having reactive groups and links the colourant with the polymer. In an alternative embodiment, the colourant is reacted directly with the polymer, without a linking agent. The coloured polymers are said to be useful as coatings for automobiles.
According to a first aspect of the present invention, there is provided a process for preparing an optical filter comprising a coloured cross-linked polymeric coating on a transparent substrate, which comprises applying to the substrate, by a printing process, a mixture comprising one or more polymer precursor(s), and one or more dye(s) capable of forming a covalent bond with the polymeric precursor via a heterocyclic NH group in a heterocyclic part of the dye or via substituent groups selected from —OH; —NHR; —SR; —COOR; epoxy; —NHCOalkenyl; or —COalkenyl, in which R is —H or alkyl, and thereafter curing the mixture.
The term heterocyclic NH group means an NH group in which the nitrogen atom forms part of a heterocyclic ring. In many dyes the heterocyclic NH group will itself be capable of forming a covalent bond with the polymer precursor.
The polymer precursor may be any organic monomer, comonomer, polymer or copolymer and mixtures thereof having groups which are capable of reacting directly with the dye(s). Where mixtures of different polymer precursors are used at least one of the polymer precursors is required to be capable of reacting with the dye(s). Examples of polymer precursors include acrylates, methacrylates, acrylamides, methacrylamides, epoxides, esters, urethanes, isocyanates, alcohols, vinylalcohols, imides, amides, phenols, acetates, carbonates and their derivatives, amines, carboxylic acids and orthoformaldehyde condensates, polyacrylic resins, polyvinylalcohol resins, melamine formaldehyde resin condensates, alkyd resins, epoxy resins, polyimides, polyamide resins, phenolic resins, polyester resins, polyvinylacetate, polycarbonate resins, urethane resins and their derivatives and copolymers.
The polymer precursor is preferably selected from acrylamides, epoxides, epoxy resins, acrylamide/epoxy resin systems, melamine formaldehyde resin condensates, polyesters, alkyd resins, hydroxylated or carboxylated acrylics, hydroxylated acrylic-melamine formaldehyde systems and especially from acrylamide/epoxy resin systems and hydroxylated acrylic-melamine formaldehyde systems.
For the purposes of the present specification dye means a compound which absorbs radiation from part of the electromagnetic spectrum and includes compounds which are infra red (IR) or ultraviolet (UV) absorbers which may or may not be coloured and coloured compounds which absorb radiation in the visible part of the electromagnetic spectrum. The dye may be referred to below as a polymer-reactive dye. It is preferably a dye with inherently high light-fastness. The dye may be selected from the monoazo, disazo, azomethine, quinophthalone, cyanine, pyrroline, maleimide, thiophenedioxide, anthraquinone, phthalocyanine, benzofuranone, benzodifuranone, triphendioxazine, triphenazonaphthylamie, styryl, dithiene and pyrrole dye classes. Dyes are preferably those which may form covalent bonds with the polymers via a heterocyclic NH group in a heterocyclic part of the dye or via substituent groups selected from a —OH; —NHR, —SH or —COOR in which R is —H or alkyl; epoxy; —COalkenyl such as —CO-vinyl and —NHCOalkenyl such as —NHCOvinyl each of which may be attached directly to the dye or via optionally substituted alkyl or aryl groups. The —OH, —NHR and —SH groups are preferably attached to aliphatic carbon atoms (e.g. —CH
2
—) to make them more reactive towards polymer precursors. Generally preferred dyes are those which have substituent groups which aid the solubility of the dye(s) in liquid media used in the process or which aid the solubility of the dye(s) in the polymer precursor(s).
A preferred azo dye is a dye of Formula (1):
A—N═N—D  Formula (1)
in which:
A is an optionally substituted heterocyclic or carbocyclic group; and
D is an optionally substituted heterocyclic or carbocyclic group or a group of Formula (2):
—E—N═N—G  Formula (2)
 in which:
E and G each independently is an optionally substituted heterocyclic or carbocyclic group.
The heterocyclic group represented by A, D, E and G may be selected from thienyl, thiazolyl, isothiazolyl, pyrazolyl, benzopyrazolyl, imidazolyl, pyridyl, pyridonyl, thiadiazolyl, furanyl, pyrrolyl, pyridazyl, pyrimidyl, pyrazinyl, benzothiazolyl, benzoisothiazolyl, quinolinyl, isoquinolinyl, indolyl, pyridothiazolyl, pyridoisothiazolyl, triazolyl, pyrrolyl, dioxazolyl, oxazolyl, isooxazolyl, imidazolyl and carbazolyl.
The cabocyclic group represented by A, D, E and G may be phenyl or naphthyl.
A is preferably phenyl, pyrazolyl, triazolyl, pyrrolyl, indolyl or carbazolyl, more preferably phenyl or pyrazolyl.
Where A is phenyl it is preferably of Formula (3):
A preferred sub group of dyes are those of Formula (1) in which A is of Formula (3),
in which:
R
1
, R
2
and R
3
each independently is alkyl, alkoxy each of which may be optionally substituted, —H, —F, —NO
2
, —Cl, —Br, —I, —CN, —CF
3
, SO
2
F, —COOR
18
, —SO
2
R
18
, —COR
18
, —SO
2
NR
18
R
19
or —CONR
18
R
19
in which R
18
and R
19
each independently is alkyl or aryl, each of which may be optionally substituted, or —H.
Where A is pyrazolyl it is preferably of Formula (4):
in which:
R
4
is —H, —CN, —NO
2
, —F, —Cl, —Br, —COR
18
, —CONR
18
R
19
, —SO
2
R
18
, —SO
2
NR
18
R
19
or —COOR
18
;
R
5
is —H, aryl, —CN, —SO
2
R
18
, alkyl or alkyl substituted by —CN, —CSNR
18
R
19
, —SR
18
or —COOR
8
; and
R
6
is —H, alkyl, aryl, alkenyl, —SO
2
R
18
, —COR
18
or alkyl subst

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