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US 5,998,211 AGranted
Use of compounds which absorb and/or fluoresce in the IR region as markers for liquids
AssigneeBASF SE
InventorsBernhard Albert, Juergen Kipper, Christos Vamvakaris, Karin Heidrun Beck, Gerhard Wagenblast
Life of this patent
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Abstract
Use of compounds from the class of the phthalocyanines, naphthalocyanines, nickel dithiolene complexes, aminium compounds of aromatic amines, methine dyes or azulenesquaric acid dyes which have their absorption maximum in the range from 600 to 1,200 nm and/or a fluorescence maximum in the range from 620 to 1,200 nm, as markers for liquids, a process for detecting markers in liquids, and a detector suitable for this purpose.
Claims1
A method of identifying a liquid comprising the sequential steps of:
- (i) detecting a marker compound in a liquid;
- and
- (ii) identifying said liquid based on the identity of said marker compound,
- wherein said marker compound exhibits an absorption maximum in the range of 600-1,200 nm and/or a fluorescence maximum in the range of 620-1,200 nm, and
- wherein said marker compound is a compound of Formula Ia, Ib, III, IV, V or VI, ##STR51## where Me.sup.1 is two hydrogen atoms, two lithium atoms or magnesium, zinc, copper, nickel, VO, TiO, AlCl or Si(OH).sub.2, at least 4 of the radicals R.sup.1 to R.sup.16, independently of one another, have the formula W-X.sup.1 in which W is a chemical bond, sulfur, imino, C.sub.1 -C.sub.4 -alkylimino or phonylimino, and X.sup.1 is C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function or substituted by phenyl, or are adamantyl or substituted or unsubstituted phenyl, and
- any remaining radicals R.sup.1 to R.sup.16 are hydrogen, halogen, hydroxysulfonyl or C.sub.1 -C.sub.4 -dialkylsulfamoyl), ##STR52## where R.sup.17 and R.sup.18 or R.sup.18 and R.sup.19 or R.sup.19 and R.sup.20 together in each case have the formula X.sup.2 -C.sub.2 H.sub.4 -X.sup.3, in which one of the two radicals X.sup.2 and X.sup.3 is oxygen and the other is imino or C.sub.1 -C.sub.4 -alkylimino, and
- R.sup.19 and R.sup.20 or R.sup.17 and R.sup.20 or R.sup.17 and R.sup.18, independently of one another, are in each case hydrogen or halogen, and
- Me.sup.1 is as defined above, ##STR53## where Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5, Y.sup.6, Y.sup.7 and Y.sup.8, independently of one another, are each hydrogen, hydroxyl, C.sub.1 -C.sub.20 -alkyl or C.sub.1 -C.sub.20 -alkoxy, where the alkyl groups may each be interrupted by from 1 to 4 oxygen atoms in ether function and may be substituted by phenyl,
- Y.sup.9, Y.sup.10, Y.sup.11 and Y.sup.12, independently of one another, are each hydrogen, C.sub.1 -C.sub.20 -alkyl or C.sub.1 -C.sub.20 -alkoxy, where the alkyl groups may each be interrupted by from 1 to 4 oxygen atoms in ether function, or are halogen, hydroxysulfonyl or C.sub.1 -C.sub.4 -dialkylsulfamoyl, and
- Me.sup.2 is two hydrogen atoms, two lithium atoms, magnesium, zinc, copper, nickel, VO, TiO, AlCl or ##STR54## where Y.sup.17 and Y.sup.18, independently of one another, are each hydroxyl, C.sub.1 -C.sub.20 -alkoxy, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.3 -C.sub.20 -alkenyloxy or ##STR55## in which Y.sup.19 is C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl or C.sub.4 -C.sub.20 -alkadienyl and Y.sup.20 and Y.sup.21, independently of one another, are each C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl or as defined for OY.sup.19 above, ##STR56## where L.sub.1, L.sup.2, L.sup.3 and L.sup.4, independently of one another, are each C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function, phenyl, C.sub.1 -C.sub.20 -alkylphenyl, C.sub.1 -C.sub.20 -alkoxyphenyl, where the alkyl groups may each be interrupted by from 1 to 4 oxygen atoms in ether function, or L.sup.1 and L.sup.2 and/or L.sup.3 and L.sup.4 in each case together are ##STR57## where Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4, independently of one another, are each C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function, C.sub.1 -C.sub.20 -alkanoyl or ##STR58## where Z.sup.4 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function, or C.sub.1 -C.sub.20 -alkanoyl, Z.sup.7 is hydrogen or C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function, and Z.sup.8 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be interrupted by from 1 to 4 oxygen atoms in ether function, or halogen, and
- An.sup..crclbar. is the equivalent of an anion, ##STR59## in which the rings A and B, independently of one another, may each be benzo-fused and/or substituted,
- E.sup.1 and E.sup.2, independently of one another, are each oxygen, sulfur, imino, --C(CH.sub.3).sub.2 -- or --CH.dbd.CH--,
- D is ##STR60## where E.sup.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl, chlorine or bromine and E.sup.4 is hydrogen or C.sub.1 -C.sub.6 -alkyl,
- Q.sup.1 and Q.sup.2, independently of one another, are each phenyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.12 -alkyl, which may be interrupted by from 1 to 3 oxygen atoms in ether function and may be substituted by hydroxyl, chlorine, bromine, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, acryloyloxy, methacryloyloxy, hydroxysulfonyl, C.sub.1 -C.sub.7 -alkanoylamino, C.sub.1 -C.sub.6 -alkylcarbamoyl, C.sub.1 -C.sub.6 -alkylcarbamoyloxy or G.sup.e (K).sub.3, where G is nitrogen or phosphorus and K is phenyl, C.sub.5 -C.sub.7 -cycloalkyl or C.sub.1 -C.sub.12 -alkyl,
- An.sup..crclbar. is the equivalent of an anion, and
- n is 1, 2 or 3, ##STR61## where J is C.sub.1 -C.sub.12 -alkylene,
- T.sup.1 is hydrogen, halogen, amino, hydroxyl, C.sub.1 -C.sub.12 -alkoxy, phenyl, substituted phenyl, carboxyl, C.sub.1 -C.sub.12 -alkoxycarbonyl, cyano, -NT.sup.7 -CO-T.sup.6, -CO-NT.sup.6 T.sup.7 or -O-CO-NT.sup.6 T.sup.7, where T.sup.6 and T.sup.7, independently of one another, are each hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, 2,2,6,6-tetramethylpiperidin-4-yl or cyclohexylaminocarbonyl, and
- T.sup.2, T.sup.3, T.sup.4 and T.sup.5, independently of one another, are each hydrogen or C.sub.1 -C.sub.12 -alkyl, which may be substituted by halogen, amino, C.sub.1 -C.sub.12 -alkoxy, phenyl, substituted phenyl, carboxyl, C.sub.1 -C.sub.12 -alkoxycarbonyl or cyano,
- with the proviso that, if T.sup.5 is hydrogen, the ring positions of the substituents J-T.sup.1 and T.sup.4 within an azulene ring may also be exchanged for one another on one or both azulene rings.
16 more elements
Dependencies are inferred from the claim text.