Compounds for mass coloration of high temperature polymers

Details Compounds for mass coloration of high temperature polymers Compounds for mass coloration of high temperature polymers

2000-09-07

2002-03-12

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S733000, C540S130000, C544S075000, C544S077000, C544S251000, C544S296000, C544S340000, C544S345000, C346S034000, C346S0330WL, C346S049000, C548S453000, C548S458000, C552S212000, C552S256000

Reexamination Certificate

active

06355783

ABSTRACT:

The invention relates to novel soluble pigment precursors possessing not only higher thermal stability but also improved solubility characteristics and to a process for mass colouration of high temperature polymers that utilizes these novel soluble pigment precursors.
Soluble pigment precursors and their thermal decomposition in situ, for example in a photosensitive composition, a polymer, an aqueous dispersion, a porous material or a surface, to form pigments having superior properties are known from EP-A-0 648 770, EP-A-0 648 817, EP-A0 654 506, EP-A-0 654 711, EP-A-0 742 255, EP-A-742 556, EP-A-0 761 772, EP-A-0 764 628, EP-A-0 892 018, EP-A-0 718 697, WO-98/32802, WO-98/45756, WO-98/45757, WO-98/58027, WO-99/01511 and WO-99/01512.
However, it has been determined that these soluble pigment precursors do not adequately meet the highest requirements. For instance, many pigment precursors, some of them readily soluble, are thermally impossible to convert selectively and quantitatively into the desired pigments. Other pigment precursors conversely combine excellent thermal convertibility with undesirably low solubility.
It has been found that, surprisingly, there is a previously unrecognized possibility of combining good solubility and superior thermal properties of pigment precursors by using novel substitution pattern. The novel compounds are highly mobile below their starting decomposition temperature and provide technically significant, in certain cases even unique application advantages as detailed hereinbelow.
The invention accordingly provides a compound of the formula
A(B)
x
  (I)
where
x is an integer from 1 to 8,
A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series, this radical being linked with x B groups via one or more heteroatoms, these heteroatoms being selected from the group consisting of N, O and S and forming part of the radical A, and
B is hydrogen or a group of the formula
although at least one B group is not hydrogen and when x is from 2 to 8 the B groups may be identical or different,
E
1
is oxygen or is selected from the group consisting of methylene, methyleneoxy and ethylene, each member of the group being unsubstituted or substituted by one R
5
or by 2 radicals, R
5
and R
6
, or is two separate radicals, R
7
and R
8
, R
7
being attached to the same atom as R
1
and R
8
to the same atom as R
4
,
E
2
is selected from the group consisting of methylene, ethylene, propylene and butylene, each member of the group being unsubstituted or substituted by one R
9
or by 2 radicals, R
9
and R
10
, or is two separate radicals, R
11
, and R
12
, R
11
being attached to the same atom as R
1
and R
12
to the same atom as R
4
,
G
1
is O or N(R
13
),
R
1
is hydrogen, methyl, ethyl, methoxy or ethoxy,
R
2
and R
3
are independently hydrogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
alkoxy-C
2
-C
8
alkylene or C
1
-C
8
alkoxy-C
2
-C
8
alkyleneoxy,
R
4
is hydrogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
alkoxy-C
2
-C
8
alkylene, C
1
-C
8
alkoxy-C
2
-C
8
alkyleneoxy, C
5
-C
6
cycloalkyl, C
5
-C
6
cycloalkoxy, phenyl, phenoxy or a 5- or 6-membered, saturated or singly to triply unsaturated heterocyclic radical,
R
5
, R
6
, R
9
, R
10
and R
12
are independently C
1
-C
8
alkyl or C
1
-C
8
alkoxy, or R
6
and R
9
together are a direct bond,
R
7
and R
8
are independently hydrogen, C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
alkoxy-C
2
-C
8
alkylene or C
1
-C
8
alkoxy-C
2
-C
8
alkyleneoxy,
R
11
is hydrogen, C
1
-C
8
alkyl or C
1
-C
8
alkoxy,
R
13
is methyl or ethyl, and
R
14
is C
1
-C
8
alkyl, C
5
-C
6
cycloalkyl, phenyl or a 5- or 6-membered, saturated or singly to triply unsaturated heterocyclic radical,
it being possible for two methoxies attached to the same carbon atom to combine and form 1,2-ethylenedioxy, or for methoxy to combine with ethoxy attached to the same carbon atom to form 1,2- or 1,3-propylenedioxy, or for methoxy or ethoxy to combine with ethoxy attached to &agr;- or &bgr;-enchained carbon to form dimethylmethylene,
and where additionally
a) R
1
, R
2
, R
3
, R
7
or R
11
is hydrogen, and
b) when E
1
is two separate radicals R
7
and R
8
and E
2
is methylene or ethylene at least one of the following further conditions applies:
R
1
, R
2
, R
3
, R
4
, R
7
, R
8
, R
9
or R
10
is methoxy or ethoxy;
R
2
, R
3
, R
4
, R
7
, R
8
, R
9
or R
10
is secondary C
3
-C
8
alkyl or tertiary C
4
-C
8
alkyl or C
3
-C
8
alkoxy;
R
2
, R
3
, R
7
or R
8
is C
1
-C
8
alkoxy-C
2
-C
8
alkylene or C
1
-C
8
alkoxy-C
2
-C
8
alkyleneoxy; or
R
4
is C
5
-C
6
cycloalkyl, C
5
-C
6
cycloalkoxy, phenyl, phenoxy or a 5- or 6-membered heterocyclic radical.
As is evident from this definition, substitution is of major significance for cyclic compounds.
C
1
-C
8
Alkyl, including in C
1
-C
8
alkoxy, is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl or any isomer of pentyl, hexyl, heptyl or octyl, such as tert-amyl or tert-octyl. C
1
-C
8
Alkyl is preferably secondary C
3
-C
8
alkyl or tertiary C
4
-C
8
alkyl. C
5
-C
6
Cycloalkyl, including in C
5
-C
6
cycloalkoxy, is cyclopentyl or cyclohexyl.
C
2
-C
8
Alkylene, including in C
1
-C
8
alkoxy, may be straight-chain, branched or cyclic. Examples are 1,2-ethylene, 1,2-propylene, 1,3-propylene, an isomer of butylene, pentylene, hexylene, heptylene, octylene or cyclopentylene, cyclohexylene or cyclooctylene.
5- or 6-membered, saturated or singly to triply unsaturated heterocyclic radicals are for example 2- or 3-furyl, 2- or 3-thienyl, 1-pyrryl, 2H-2-pyrryl, 2H-2-pyranyl, 4H-4-pyridyl, 1-, 2-, 3- or 4-piperidyl, 1-, 2- or 3-pyrrolidinyl, or any isomer of imidazolidinyl imidazolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, quinuclidinyl, pyrazinyl, pyrimidinyl, pyridazinyl, morpholinyl, furyl, dihydrofuryl, tetrahydrofuryl, dihydropyranyl or tetrahydropyranyl.
Examples of bicyclic groups on the carboxyl group in the formula (II) are cyclic terpene radicals, such as thujyl, caryl, pinyl, bornyl, norcaryl, norpinyl or norbornyl.
E
1
is preferably oxygen, methylene or two separate radicals R
7
and R
8
, especially methylene or two separate radicals R
7
and R
8
.
E
2
is preferably ethylene or two separate radicals R
1
, and R
12
.
G
1
is preferably O.
R
1
is preferably hydrogen, methyl, ethyl, methoxy or ethoxy.
R
2
, R
3
and R
4
are preferably hydrogen or C
1
-C
8
alkyl.
R
5
, R
6
, R
9
, R
10
and R
12
are preferably methyl, secondary C
3
-C
8
alkyl or tertiary C
4
-C
8
alkyl.
R
7
, R
8
and R
11
are preferably hydrogen or methyl, especially hydrogen.
R
14
is preferably C
1
-C
8
alkyl.
Preference is given to B groups which exclusively of the carboxyl group contain at most 3 further oxygen atoms, especially no or 1 to 2 further oxygen atoms, particularly preferably no or 1 further oxygen atom. When a B group exclusively of the carboxyl group contains 2 or 3 further oxygen atoms, it is preferable for no carbon atom in this B group other than in the carboxyl group to be bonded to more than one oxygen atom.
Preference is given to groups of the formulae (II) or (III) which are asymmetrical. Particular preference is given to groups of the formulae
where R
15
is —CR
1
R
7
R
11
and R
16
is —CR
2
R
3
—CR
4
R
8
R
12
or —CR
2
R
3
—G
1
R
14
, and R
2
, R
3
, R
4
, R
7
, R
8
, R
9
or R
10
is secondary C
3
-C
8
alkyl or tertiary C
4
-C
8
alkyl, especially tert-butyl, tert-amyl or 2,4-dimethyl-2-pentyl.
Very particular preference is given to groups of the formulae (II) and especially (IV).
The compounds of the invention are notable for improved thermal characteristics. At temperatures of about 140° C. to about 220° C., customary during incorporation into many polymers, they will disperse therein very homogeneously, usually with complete dissolution, without decomposing into the pigment. On cooling they crystallize back out within the polymer. This provides, for example with the diketopyrrolopyrroles, excellent, particular

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