Donor-substituted oxindigo derivatives and their use as colorant

Details Donor-substituted oxindigo derivatives and their use as colorant Donor-substituted oxindigo derivatives and their use as colorant

1998-10-05

2000-12-05

Owens, Amelia

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30702

Patent

active

061569143

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to oxindigo derivatives of the general formulae 1 and 2 ##STR1## in which
four to seven of the radicals R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are hydrogen and one to four of these radicals is or are a radical chosen from the group consisting of an unsubstituted or substituted carbocyclic aromatic radical, an unsubstituted or substituted heterocyclic aromatic radical, halogen, unsubstituted or substituted C.sub.1 -C.sub.18 alkyl, --OR.sup.12, --CN, --NR.sup.10 R.sup.11, --COR.sup.9, --NR.sup.13 COR.sup.9, --NR.sup.12 COOR.sup.9, --NR.sup.12 CONR.sup.10 R.sup.11, --NHSO.sub.2 R.sup.9, --SO.sub.2 R.sup.9, --SOR.sup.9, --SO.sub.2 OR.sup.9, --CONR.sup.10 R.sup.11, --SO.sub.2 NR.sup.10 R.sup.11, --N.dbd.NR.sup.14, --OCOR.sup.9 and --OCONHR.sup.9, wherein two corresponding adjacent radicals can be combined to build up fused-on aromatic rings,
in which R.sup.9 is C.sub.1 -C.sub.18 alkyl, C.sub.6 -C.sub.10 aryl or benzyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or a five- to seven-membered heterocyclic radical,
R.sup.10 and R.sup.11 independently of one another are hydrogen, C.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by cyano or hydroxy groups, C.sub.3 - to C.sub.24 cycloalkyl, C.sub.6 -C.sub.10 aryl or 5- to 7-membered heteroaryl, or in which R.sup.10 and R.sup.11, together with in each case one of the other radicals R.sub.2 to R.sub.4, form a 5- or 6-membered carbocyclic or heterocyclic ring,
R.sup.12 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.3 - to C.sub.24 cycloalkyl, C.sub.6 -C.sub.10 aryl or 5- to 7-membered heteroaryl,
R.sup.13 is hydrogen, C.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by cyano, hydroxy or C.sub.1 -C.sub.4 alkyoxycarbonyl groups, C.sub.3 - to C.sub.24 cycloalkyl, C.sub.1 -C.sub.4 alkylaryl, C.sub.6 -C.sub.10 aryl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl- or C.sub.1 -C.sub.4 alkoxy groups, or a 5 to-7-membered heterocyclic radical, and
R.sup.14 is the radical of a coupling component or is
C.sub.6 -C.sub.10 aryl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups,
and mixtures of the oxindigo derivatives 1 and 2, with the proviso that in the oxindigo derivatives 1 (transform) R.sub.1 and R.sub.2 are not simultaneously methyl or methoxy, or
R.sub.5 and R.sub.6 are not simultaneously chlorine, or
R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are not simultaneously methyl, or
R.sub.1, R.sub.2, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are not simultaneously methyl,
if in each case all the other radicals from the list of R.sub.1 to R.sub.8 are hydrogen, and with the further proviso that if R.sub.1 in the cis-oxindigo derivative 2 is a dimethylamino group, R.sub.2 is not simultaneously a hydroxy group.
The invention furthermore relates to a process for the preparation of the compounds according to the invention, their use as colorants and intermediates. ##STR2## (cf. for example Ber.Dtsch.Chem.Ges. 44 (1911) 124-128), as a chromophoric system, has not acquired any industrial importance at all as a colorant, in contrast to its nitrogen analog indigo or the sulfur analog thioindigo. The reason for this is, inter alia, that oxindigo absorbs at a very short wavelength (413 nm in cyclohexane, cf. J.Chem.Soc. D 1969, 133-134), has a relatively low extinction coefficient (13800, ibid.), is not fluorescent, has a relatively low stability and, furthermore, is also difficult to prepare.
Methyl- and methoxy-substituted compounds, which can be non-brominated or brominated, dichlorinated compounds, dibenzo-substituted compounds and derivatives with a C(O)O(CH.sub.2).sub.2)OMe radical and two --C.sub.18 H.sub.37 -- radicals are known from Justus Liebigs Ann. Chem. 405 (1914) 365, 372; Justus Liebigs Ann.Chem. 442 (1925) 263, 278, 284-300; J. Amer. Chem. Soc. 73 (1951) 4294, 4297; Chem.Ber. 54 (1921) 2933; Org.Mass.Spectrom. 24(6) (1989) 429-430; JP-A 61180237; JP-A 61179791 and

REFERENCES:
patent: 4212823 (1980-07-01), Muller
Smith et al., J. of the Amer. Chem. Soc., vol. 73, pp. 4294-4297 (1951).
Chem. Abstracts, vol. 23, pp. 1278-1279 (1929) of German patent 469,178 filed Oct. 22, 1926.
Fries et al., Berichte Der Deutschen Chemischen Gesellschaft, vol. 54, No. 2, pp. 293-296 (1921).
Fries et al., Justus Liebigs Annalen Der Chemie, vol. 442, pp. 284-300 (1925).
Fries et al., Justus Liebigs Annalen Der Chemie, vol. 405, pp. 365-372 (1914).
Ruhemann, Journal of the Chem. Soc., vol. 83, pp. 1130-1135 (1903).
Artico et al., Biochemical Pharmcology, vol. 17, pp. 873-882 (1968).
Skinner et al., Journal of Organic Chemistry, vol. 26, pp 152-155 (1961).
Kimachi et al., Journal of the Heterocyclic Chemistry, vol. 26, pp. 1255-1259 (1989).
Valenta et al., Journal of the American Chemical Society, vol. 86, pp. 2533-2534 (1964).
Crossley et al., Journal of the American Chemical Society, vol. 74, No. 3, pp. 573-578 (1952).
Umemoto et al., Chemical Abstracts, vol. 73, No. 26, p. 47, col. 1 (1970).
Langhal et al., Angew. Chem., vol. 108, pp 1090-1093 (1996).
Fries et al., Chem Ber., vol. 54, pp 2931-34 (1921).
Garcia et al., Org. Mass Spectrometry, vol. 24(6), pp. 429-430 (1989).
Fries et al., Ber. Dtsch. Chem. Ges., vol. 44, pp. 124-128 (1911).
Gusten, Chemical Communications, pp. 133-134 (1969).

Affiliated with

Also associated with

Rating

Donor-substituted oxindigo derivatives and their use as colorant does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Donor-substituted oxindigo derivatives and their use as colorant, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Donor-substituted oxindigo derivatives and their use as colorant will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-962940