Dye compounds

Details Dye compounds Dye compounds

2001-07-13

2003-05-06

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C546S029000, C546S037000, C546S038000, C546S047000, C546S098000, C546S100000, C106S031470

Reexamination Certificate

active

06559306

ABSTRACT:

This invention relates to new fluorescent or non-fluorescent dye molecules having a terminal hydroxy, carboxylic acid/ester or amino group.
BACKGROUND
Articles containing colorants are known to loose their colour when exposed to solar radiation for extended times. In particular, fluorescent colorants degrade more quickly than conventional colorants, often turning colourless on exposure to daily solar radiation within days or months.
Colorants not covalently bond in a polymer matrix tend to agglomerate and to crystalize leading to inhomogeneous distribution of colorants within the matrix. Fluorescent colorants in particular often loose their fluorescent properties by agglomeration of fluorescent sites (quenching). Furthermore with non covalently bond colorants, fading or bleeding of the colorant occurs.
U.S. Pat. No. 6,103,006 (DiPietro) discloses fluorescent polymeric pigments with increased lightfastness obtained by the polycondensation of dye monomers with at least two functional groups like diamine, dialcohol or dicarboxylic acid. The functional groups for the polycondensation are directly located at the dye moiety as in the anhydride or diacid form of the BXDA fluorescent dye.
Besides the above mentioned polycondensation process the polyreaction of chain growth polymers can be utilised to react dye monomers into a polymer backbone. WO 99/21937 (3M) discloses a two phase interpenetrating polymer network system with a dye functionalized polymer in the second phase. The optionally fluorescent dye is covalently bond to the polymer to slow migration and to enhance compatibility, e.g. a hydroxy functional dye (YGOH) is reacted into a polyurethane or an acrylate functional dye (YGOAcr) is reacted into a respective chain growth polymer.
Other structures known to have dye properties are disclosed in WO 00/31039 in a completely different context: as pharmaceutically active compounds for the control of thrombotic disorders and for use as anti-adhesive substances for implants, catheters or heart pacemakers. The substituents are selected in view of pharmaceutical activity and applicability and the substituted benzo[de]isoquinoline-1,3-diones are not supposed to have any connective function.
SUMMARY OF THE INVENTION
One objective of the present invention is to provide new dye compounds that have a connective functionality attached to the dye moiety by a spacer of a chain length of C
3
or longer. The dye compounds are useful useful as colorants for preparing colored synthetic polymer resins with pigmentary properties, for dyeing or printing homo- or mixed synthetic, semi-synthetic or natural polymers or substrates or for preparing inks.
DETAILED DESCRIPTION OF THE INVENTION
The dye compound is of the general formula (I)
in which R
1
is C
3-12
alkylen, C
2
alkoxy alkylene, C
6-10
arylen, (C
6-10
) aryl-(C
1-6
) alkylen or (C
1-6
) alkyl-(C
6-10
) arylen, the alkylen and/or arylen radicals optionally being substituted by hydroxyl, C
1-6
alkoxyl, C
6-10
aryloxy or halogen,
X is hydroxy, COOR′ or NHR′ with R′ being hydrogen, C
1-6
alkyl, C
6-10
aryl, (C
6-10
) aryl-(C
1-6
) alkyl or (C
1-6
) alkyl-(C
6-10
) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, C
1-6
alkoxyl, C
6-10
aryloxy or halogen,
A is a substituted or unsubstituted fused aromatic or heterocyclic ring system, preferably of the general formula (III), (IV), (V), (VI), (VII) or (VIII)
wherein R
3
is hydrogen, halogen, NR
4
R
5
, R
4
O or R
4
S, with R
4
being hydrogen, C
1-6
alkyl, C
6-10
aryl, (C
6-10
) aryl-(C
1-6
) alkyl or (C
1-6
) alkyl-(C
6-10
) aryl, the alkyl and/or aryl radicals optionally being substituted by hydroxyl, C
1-6
alkoxyl, C
6-10
aryloxy or halogen, subsequently R
5
being hydrogen, C
2-6
alkyl, C
6-10
aryl, (C
6-10
) aryl-(C
1-6
) alkyl or (C
3-6
) alkyl-(C
6-10
) aryl, the alkyl radicals optionally being substituted by C
1-6
alkoxyl, C
6-10
aryloxy or halogen, the aryl radicals optionally being substituted by hydroxyl, C
1-6
alkoxyl, C
6-10
aryloxy or halogen, with the provisio that R
4
is to be chosen first and if R
4
is hydrogen, R
5
can only be hydrogen; Y being sulphur, oxygen or NR
4
, with R
4
having the meaning given above,
R
6
and R
7
are identical or different and are hydrogen, C
1-6
alkyl, C
6-10
aryl, (C
6-10
)aryl-(C
1-6
)alkyl or (C
1-6
)alkyl-(C
6-10
)aryl, it being possible for the alkyl and/or aryl radicals to be substituted by hydroxyl, C
1-6
alkoxy, C
6-10
aryloxy or halogen and
p and q are 0-12
Another dye compound is of the general formula (II)
wherein R
1
and X have the meaning given above,
with the proviso that for X being NH
2
, R
1
being C
6
alkylen is excluded and with the proviso that for X being OH, R
1
being C
3
alkylen is excluded.
Especially preferred dye compounds are those of the general formula (I) where A is of the general formula (IV), with Y being sulphur and R
3
being hydrogen, where A is of the general formula (VI) with R
3
being hydrogen, where A is of the general formula (VII) with R
3
being hydrogen and where A is of the general formula (VIII) with R
6
and R
7
being methyl and p and q being 1.
The preferred spacer R
1
is a C
3-6
alkylen, most preferably C
6
alkylen. Another preferred spacer R
1
is a ethoxy-ethoxy-ethylene.
Preferred terminal groups X are hydroxy or NHR′ with R′ being preferably hydrogen, methyl or ethyl.
The dye compounds of formulae (I) are obtained by the condensation of the dicarboxylic anhydride of the respective dye moiety with an aminoalcohol, an aminoacid/ester or a diamine comprising the respective spacer in a polar aprotic solvent.
The hydroxy, carboxylic acid/ester or amino group on the free end of the spacer can be reacted into a polymer network, e.g. polyurethane, polyester or aminoformaldehyde resin.
To obtain such colored polymer resins, the dye compound is mixed into a respective reactive mixture comprising isocyanates or formaldehyde and optionally other carboxy, hydroxy or amine functionalized compounds before the reaction is carried out. The polyreactions to obtain polyurethane, polyester or aminoformaldehyde resins are well known in the art.
The dye compounds according to the invention may be used for dyeing dyeable materials such as homo- or mixed synthetic, semi-synthetic or natural polymers e.g. acrylonitrile, polyester, polyurethane, polyamide, wool, leather, cotton, bast fibers such as hemp, flax, sisal, jute, coir and straw; regenerated cellulose fibers, glass or glass products comprising glass fibers; and substrates comprising cellulose for example paper and cotton. They may also be used for printing fibers, filaments and textiles comprising any of the above mentioned materials in accordance with known methods. The compounds of the present invention may be further used in the preparation of inks, e.g. ink jet inks in accordance with conventional methods.
The colored polymer resins are suitable for the mass pigmentation of synthetic resins, e.g. polyurethane masses, polyester or aminoformaldehyde resins.
The obtained resins are suitable, as colorants in powders and powder coating materials, especially in triboelectrically or electrokinetically sprayable powder coating materials which are used for the surface coating of articles made, for example, from metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
Powder coating resins that are typically employed are epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane resins and acrylic resins, together with customary hardeners. Combinations of resins are also used. For example, epoxy resins are frequently employed in combination with carboxyl- and hydroxyl-containing polyester resins. Typical hardener components (as a function of the resin system) are, for example, acid anhydrides, imidazoles and also dicyanodiamide and its derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.


REFERENCES:
patent: 4007192 (1977-02-01), F

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