Use of aminotriarylmethanes for marking hydrocarbons and novel a

Details Use of aminotriarylmethanes for marking hydrocarbons and novel a Use of aminotriarylmethanes for marking hydrocarbons and novel a

1995-11-30

1999-11-23

Clardy, S. Mark

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

Organic compounds

Acyclic carbon bonded directly to three benzene rings and to...

585 2, 585 3, 585 4, C09B 1100, C07C 720

Patent

active

059903279

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to the use of aminotriarylmethanes of the formula I ##STR2## where the ring A may be benzofused, the other C.sub.1 -C.sub.13 -alkyl with or without interruption by from 1 to 3 oxygen atoms in ether function and with or without amino or hydroxyl substitution, or substituted or unsubstituted phenyl, or R.sup.1 and R.sup.2 are together with the nitrogen atom joining them together a 5- or 6-membered saturated heterocyclic radical with or without a further heteroatom, or else R.sup.1 is hydrogen, the other C.sub.1 -C.sub.20 -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function and with or without amino, hydroxyl or phenyl substitution, or else R.sup.3 is hydrogen, and the other C.sub.1 -C.sub.13 -alkyl with or without interruption by from 1 to 3 oxygen atoms in ether function and with or without amino or hydroxyl substitution, or a radical of the formula NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are each as defined above, or else one of X.sup.1 and X.sup.2 is hydrogen, of the formula I, a method for detecting the aminotriarylmethanes of the formula I in hydrocarbons, and novel aminotriarylmethanes.
U.S. Pat. No. 5,145,573 discloses the use of triarylmethane dyes or triarylmethanecarbinols for marking mineral oils.
It is an object of the present invention to provide novel markers for hydrocarbons. The novel markers shall be readily obtainable and soluble in hydrocarbons. They shall also be simple to detect; specifically, even very small amounts of marker shall be visibilizable through a strong color reaction.
We have found that this object is achieved by the above-defined aminotriarylmethanes of the formula I.
Any alkyl appearing in the abovementioned formula I may be straight-chain or branched.
Any substituted alkyl appearing in the abovementioned formula I generally has 1 or 2 substituents.
Any substituted phenyl appearing in the abovementioned formula I may have as substituents for example C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy. The substituents generally number from 1 to 3.
R.sup.1 and R.sup.2 combined with the nitrogen atom joining them together into a 5- or 6-membered saturated heterocyclic radical with one further hetero atom can be for example pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N-(C.sub.1 -C.sub.4 -alkyl)piperazinyl.
R.sup.1, R.sup.2, R.sup.3, R.sup.4, X.sup.1 and X.sup.2 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above designations isooctyl, isononyl, isodecyl and isotridecyl are trivial names derived from the oxo process alcohols--cf. Ullmann's Encyklopadie der technischen Chemie, 4th edition, Volume 7, pages 215 to 217, and Volume 11, pages 435 and 436), 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 5-hydroxy-3-oxapentyl, 2-aminoethyl, 2- or 3-aminopropyl, 2- or 4-aminobutyl, 5-aminopentyl, 6-aminohexyl, 7-aminoheptyl, 8-aminooctyl, 5-amino-3-oxapentyl, 6-amino-3-oxahexyl, 6-amino-4-oxahexyl, 7-amino-4-oxaheptyl, 8-amino-3,6-dioxaoctyl, 3-aminoprop-2-yl, 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, 3,6-dioxaheptyl, 3,6-dioxyoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 2- or 4-butoxybutyl, 4,8-dioxadecyl, 3,6,9-trioxadecyl or 3,6,9-trioxaundecyl.
R.sup.3 and R.sup.4 may each also be for example tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, benzyl, 1- or 2-phenylethyl, 3,6,9-trioxadodecyl, 3,6,9,12-tetraoxatridecyl or 3,6,9,12-tetraoxatetradecyl.
Preference for marking hydrocarbons is given to the use of aminotriarylmethanes of the formula I where R.sup.1 and

REFERENCES:
patent: 5145573 (1992-09-01), Riedel et al.
patent: 5233048 (1993-08-01), Eckstein et al.

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