Use of compositions containing bisazo compounds for...

Details Use of compositions containing bisazo compounds for... Use of compositions containing bisazo compounds for...

2001-05-17

2003-09-09

Kopec, Mark (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dye or potential dye composition, additive, treatment,...

Mixed dyes, noncomplexed

C008S466000, C008S662000

Reexamination Certificate

active

06616712

ABSTRACT:

The present invention relates to the use of compositions comprising as components
A) at least one bisazo compound selected from the group consisting of the compounds of the formula Ia
 and of the general formula Ib
 where
R
1
is C
1
-C
8
-alkyl,
R
2
is C
2
-C
8
-alkyl,
R
3
and R
3′
are each C
2
-C
21
-alkyl in which up to four CH
2
groups of the carbon chain may be replaced by oxygen in ether function,
R
4
is hydrogen or is R
3
(independently of R
3
),
R
4′
is hydrogen or is R
3′
(independently of R
3′
),
B) at least one solvent in which said component A) is soluble, and optionally
C) at least one surface-active substance,
as dye penetrants for detecting surface cracks or other defects in workpieces to be tested in this respect.
The present invention further relates to compositions comprising the abovementioned components A), B) and C).
U.S. Pat. No. 4,191,048 describes a method for detecting cracks and other defects in workpieces. The cracks are detected using a composition comprising a solution of an isomer mixture of a red, daylight visible bisazo dye and a surfactant that is miscible with said solution. This isomer mixture of the red bisazo dye is derived from (randomly) methyl-substituted aminoazobenzene (as starting material for the diazo component) and a C
5
-C
12
-alkyl-&bgr;-naphthol or mixtures of such C
5
-C
12
-alkyl-&bgr;-naphthols (as coupling component).
This dye (or, to be more precise, the isomer mixture of this dye) does indeed provide clear indications of cracks in the test workpiece, but there is a disadvantage in that toxicologically suspect, isomeric bisazo compounds are present.
German Offenlegungsschrift DE-A 35 07 174 describes a process for documenting crack tests on workpieces by means of dyes or dye intermediates which transfer out of the cracks of the workpiece onto a sheetlike substrate with which the workpiece is contacted. The preferred substrate in question is said to be paper, optionally provided with a receiver layer.
Suitable dyes are said to be Solvent Yellow 56 (C.I. 11021), Solvent Yellow 14 (C.I. 12055), Disperse Red 1 (C.I 11110), Disperse Blue 3 (C.I. 61505) and Solvent Orange 3 (C.I 11270).
The aforementioned oil-soluble yellow and orange (“solvent”) dyes, being light-colored, generally provide an insufficient contrast to the color of the workpiece, while the aforementioned “disperse” dyes are in turn insufficiently soluble in the solvent of the dye penetrant, so that an insufficient contrast to the color of the workpiece results because of the insufficient dye concentration.
It is an object of the present invention to provide a dye penetrant composition which provides a high contrast indication of cracks and voids and whose dye(s) is or are not based on amines of class III A 2, as defined in TRGS (German technical regulations for hazardous materials) 614.
We have found that this object is achieved by the use of the initially described compositions as dye penetrants for detecting surface cracks or other surface defects in workpieces to be tested in this respect.
Suitable C
2
-C
8
-alkyl for R
2
includes not only unbranched alkyl chains, e.g., ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-pentyl, pent-2-yl, pent-3-yl, n-hexyl, hex-2-yl, hex-3-yl, n-heptyl, hept-2-yl, hept-3-yl, hept-4-yl, n-octyl, oct-2-yl, oct-3-yl and oct-4-yl, but also branched alkyl chains, e.g., isobutyl, tert-butyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and 2-ethylhexyl.
Suitable C
1
-C
8
-alkyl for R
1
includes methyl in addition to the aforementioned radicals.
Suitable C
2
-C
21
-alkyl for R
3
and R
4
and for R
3′
and R
4′
, in addition to the branched or unbranched C
2
-C
8
-alkyl radicals already mentioned as examples under R
2
, includes in each case independently not only unbranched C
9
-C
21
-alkyl, e.g., n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl or n-heneicosyl, and the corresponding radicals which are isomeric in respect of their point of attachment (yl position), but also the corresponding branched C
9
-C
21
-alkyl radicals.
Examples of C
2
-C
21
-alkyl in which up to four CH
2
groups of the carbon chain may be replaced by oxygen in ether function for R
3
and R
4
and for R
3′
and R
4′
are 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl.
Further suitable such radicals are oligopropylene glycol groupings which are derived through addition of one, two, three or four propylene oxide molecules per amino group of the naphthylamine, and also their methyl or ethyl ethers.
Such radicals conform for example to the formulae —(O—CH
2
—CH
2
(CH
3
)—)
n
—OR or —(O—CH
2
(CH
3
)—CH
2
—)
n
—OR, where n is 1, 2, 3 or 4 and R is hydrogen, methyl or ethyl.
Preference is given to using compositions in which R
1
and R
2
are each respectively C
1
-C
4
-alkyl and C
2
-C
4
-alkyl as included in the examples recited above.
C
2
-C
21
-Alkyl for R
4
and/or R
3
and for R
4′
and/or R
3′
is in particular 2-ethylhexyl and branched or unbranched tridecyl.
Particular preference is given to using compositions in which said component A) comprises at least one bisazo compound of the formula Ia. The hereinbefore mentioned preferences also concern the particularly preferred composition mentioned herein.
The bisazo compounds of the formulae Ia and Ib are customarily prepared in two reaction steps. Azo coupling the diazo compound obtained from meta-R
1
-aminobenzene ((K
1
)) or ortho-R
2
-aminobenzene ((K
2
)) with a further molecule of the corresponding amine gives the substituted azobenzene (“di-(K
1
)” or “di-(K
2
)”) in the first step. This substituted azobenzene is in turn diazotized and reacted in the second step with a molecule of the R
3
,R
4
- or R
3′
,R
4′
-(di)substituted naphthylamine (coupling component (K
3
) or (K
3′
)) to form the corresponding target compound of the formula Ia or Ib. The reaction scheme hereinbelow illustrates this once more by way of example for the preparation of bisazo compounds of the formula Ia.
This scheme holds very similarly, mutatis mutandis, for the preparation of the compounds of the formula Ib.
The preparation of such compounds to be used according to this invention is effected for example along the lines of the directions in German Auslegeschrift DE 24 13 369 B2 and German Offenlegungsschrift DT 23 61 758 A1 and therefore does not present a problem to one skilled in the art.
The alkyl radicals R
1
and R
2
of the aromatic amine components (K
1
) and (K
2
), respectively, are usually defined radicals, i.e., the amine components (K
1
) and (K
2
) are generally pure compounds.
However, the radicals R
3
and/or R
4
or R
3′
and/or R
4′
of the coupling component (K
3
) (or (K
3′
), respectively), are frequently mixtures of a plurality of isomeric alkyl radicals, especially in the case of higher alkyl radicals in which up to four CH
2
groups of the carbon chain may be replaced by oxygen in ether function, so that the (di)substituted naphthylamines (K
3
) and (K
3′
) are in a given case representative of isomer mixtures with regard to these radicals.
This is usually attributable to the synthesis of such (di)substituted naphthylamines, since these are customarily prepare

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