Method for tagging petroleum products

Claim 3

The method of claim 1, wherein the petroleum hydrocarbon is gasoline.

Claim 4

The method of claim 1, wherein the petroleum hydrocarbon is kerosene.

Claim 5

The method of claim 1, wherein the petroleum hydrocarbon is lubricant oil.

Claim 6

The method of claim 1, wherein the petroleum hydrocarbon is furnace oil.

Claim 7

The method of claim 1, wherein the near infrared fluorophoric compound is selected from the group consisting of phthalocyanines, 2,3-naphthalocyanines, squaraines and croconic acid derivatives and correspond to Formulae I, II, III, and IV, respectively: ##STR42## wherein Pc and Nc represent the phthalocyanine and naphthalocyanine moieties of Formulae Ia and IIa, ##STR43## respectively, covalently bonded to hydrogen or to halometals, organometallic groups, and oxymetals selected from the group consisting of AlCl, AlBr, AlF, AlOR 5 , AlSR 5 , SICl 2 , SiF 2 , Si(OR 6 ) 2 , Si(SR 6 ) 2 , Zn and Mg, wherein R 5 and R 6 are selected from hydrogen, alkyl, aryl, heteroaryl, alkanoyl, arylcarbonyl, arylaminocarbonyl, trifluoroacetyl, ##STR44## wherein R 7 , R 8 and R 9 are independently selected from alkyl, phenyl or phenyl substituted with alkyl, alkoxy or halogen; X is selected from oxygen, sulfur, selenium, tellurium or a group of the formula N--R 10 , wherein R 10 is hydrogen, cycloalkyl, alkyl, acyl, alkylsulfonyl, or aryl or R 10 and R taken together form an aliphatic or aromatic ring with the nitrogen atom to which they are attached; Y is selected from alkyl, aryl, heteroaryl, halogen or hydrogen; R is selected from hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, alkylene ##STR45## or alkylene ##STR46## --(X-R) m is one or more groups selected from alkylsulfonylamino, arylsulfonylamino, or a group selected from the formulae --X(C 2 H 4 O) z R, ##STR47## wherein R is as defined above; Z is an integer of from 1-4; or two --(X-R) m groups can be taken together to form divalent substituents of the formula ##STR48## wherein each X 1 is independently selected from --O--, --S--, or --N--R 10 and A is selected from ethylene; propylene; trimethylene; and such groups substituted with lower alkyl, lower alkoxy, aryl and cycloalkyl; 1,2-phenylene and 1,2-phenylene containing 1-3 substituents selected from lower aklyl, lower alkoxy or halogen; R' and R" are independently selected from lower alkyl and cycloalkyl; R 1 and R 2 are independently selected from hydrogen, alkyl, alkoxy, halogen, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkyl-sulfonylamino, arylsulfonylamino, cycloalkylsulfonylamino, unsubstituted and substituted carbamoyl and sulfamyl, alkoxycarbonyl, cycloalkoxycarbonyl, alkanoyloxy, ##STR49## R 3 and R 4 are independently selected from hydrogen, lower alkyl, alkenyl or aryl; n is an integer from 0-16; n 1 is an integer from 0-24, m is an integer from 0-16; and m 1 is an integer from 0-24; provided that the sums of n+m and n 1 +m 1 are 16 and 24, respectively.

Claim 8

The method of claim 6, wherein the near infrared fluorescing compound is a squaraine compound of Formula III, and wherein R 1 and R 2 are independently alkoxycarbonyl.

Claim 9

The method of claim 6, wherein the near infrared fluorescing compound is a 2,3-naphthalocyanine compound of Formula II, and wherein the naphthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOR 5 , SICl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg, m 1 is 0, Y is alkyl and n 1 is 24 and wherein the Y groups represent at least four alkyl or aryl groups.

Claim 10

The method of claim 6, wherein the naphthalocyanine compound of Formula II is bonded to hydrogen.

Claim 11

The method of claim 6, wherein the near infrared fluorescing compound is a phthalocyanine compound of Formula I, and wherein X is oxygen, R is aryl or alkyl, Y is hydrogen, m is 4, and n is 12; and wherein the phthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOCOCF 3 , AlOR 5 , SICl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg.

Claim 12

The method of claim 6, wherein the phthalocyanine compound of Formula I is bonded to hydrogen.

Claim 15

The method of claim 12, wherein the petroleum hydrocarbon material is gasoline.

Claim 16

The method of claim 12, wherein the petroleum hydrocarbon material is kerosene.

Claim 17

The method of claim 12, wherein the petroleum hydrocarbon material is lubricant oil.

Claim 18

The method of claim 12, wherein the petroleum hydrocarbon material is furnace oil.

Claim 19

The method of claim 12, wherein the near infrared fluorophoric compound is selected from the group consisting of phthalocyanines, 2,3-naphthalocyanines, squaraines and croconic acid derivatives and correspond to Formulae I, II, III, and IV, respectively: ##STR50## wherein Pc and Nc represent the phthalocyanine and naphthalocyanine moieties of Formulae Ia and IIa, ##STR51## respectively, covalently bonded to hydrogen or to halometals, organometallic groups, and oxymetals selected from the group consisting of AlCl, AlBr, AlF, AlOR 5 , AlSR 5 , SiCl 2 , SiF 2 , Si(OR 6 ) 2 , Si(SR 6 ) 2 , Zn and Mg, wherein R 5 and R 6 are selected from hydrogen, alkyl, aryl, heteroaryl, alkanoyl, arylcarbonyl, arylaminocarbonyl, trifluoroacetyl, ##STR52## groups of the formulae ##STR53## wherein R 7 , R 8 and R 9 are independently selected from alkyl, phenyl or phenyl substituted with alkyl, alkoxy or halogen; X is selected from oxygen, sulfur, selenium, tellurium or a group of the formula N-R 10 , wherein R 10 is hydrogen, cycloalkyl, alkyl, acyl, alkylsulfonyl, or aryl or R 10 and R taken together form an aliphatic or aromatic ring with the nitrogen atom to which they are attached; Y is selected from alkyl, aryl, heteroaryl, halogen or hydrogen; R is selected from hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, alkylene ##STR54## --(X-R) m is one or more groups selected from alkylsulfonylamino, arylsulfonylamino, or a group selected from the formulae --X(C 2 H 4 O) z R, ##STR55## wherein R is as defined above; Z is an integer of from 1-4; or two --(X-R) m groups can be taken together to form divalent substituents of the formula ##STR56## wherein each X 1 is independently selected from --O--, --S--, or --N-R 10 and A is selected from ethylene; propylene; trimethylene; and such groups substituted with lower alkyl, lower alkoxy, aryl and cycloalkyl; 1,2-phenylene and 1,2-phenylene containing 1-3 substituents selected from lower aklyl, lower alkoxy or halogen; R' and R" are independently selected from lower alkyl and cycloalkyl; R 1 and R 2 are independently selected from hydrogen, alkyl, alkoxy, halogen, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkyl-sulfonylamino, arylsulfonylamino, cycloalkylsulfonylamino, unsubstituted and substituted carbamoyl and sulfamyl, alkoxycarbonyl, cycloalkoxycarbonyl, alkanoyloxy, ##STR57## R 3 and R 4 are independently selected from hydrogen, lower alkyl, alkenyl or aryl; n is an integer from 0-16; n 1 is an integer from 0-24, m is an integer from 0-16; m 1 is an integer from 0-24; provided that the sums of n+m and n 1 +m 1 are 16 and 24, respectively.

Claim 20

The method of claim 17, wherein the near infrared fluorescing compound is a squaraine compound of Formula III, and wherein R 1 and R 2 are independently alkoxycarbonyl.

Claim 21

The method of claim 17, wherein the near infrared fluorescing compound is a 2,3-naphthalocyanine compound of Formula II, and wherein the naphthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOR 5 , SiCl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg, m 1 is 0, Y is alkyl and n 1 is 24 and wherein the Y groups represent at least four alkyl or aryl groups.

Claim 22

The method of claim 17, wherein the naphthalocyanine compound of Formula II is bonded to hydrogen.

Claim 23

The method of claim 17, wherein the near infrared fluorescing compound is a phthalocyanine compound of Formula I, and wherein X is oxygen, R is aryl or alkyl, Y is hydrogen, m is 4, and n is 12; and wherein the phthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOCOCF 3 , AlOR 5 , SiCl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg.

Claim 24

The method of claim 17, wherein the phthalocyanine compound of Formula I is bonded to hydrogen.

Claim 25

A petroleum hydrocarbon having dissolved therein at least one near infrared fluorophoric compound selected from the group consisting of squaraines, phthalocyanines and naphthalocyanines having at least one straight or branched chain C 4 to C 20 alkyl group, and croconic acid derivatives.

Claim 26

A petroleum hydrocarbon having dissolved therein at least one near infrared fluorophoric compound selected from the group consisting of squaraines, phthalocyanines and naphthalocyanines having at least one straight or branched chain C 4 to C 20 alkyl group, and croconic acid derivatives.

Claim 27

The petroleum hydrocarbon of claim 23, wherein the near infrared fluorophoric compound is selected from the group consisting of phthalocyanines, 2,3-naphthalocyanines squaraines (squaric acid derivatives) and croconic acid derivatives and correspond to Formulae I, II, III, and IV, respectively: ##STR58## wherein Pc and Nc represent the phthalocyanine and naphthalocyanine moieties of Formulae Ia and IIa, ##STR59## respectively, covalently bonded to hydrogen or to halometals, organometallic groups, and oxymetals selected from the group consisting of AlCl, AlBr, AlF, AlOR 5 , AlSR 5 , SiCl 2 , SiF 2 , Si(OR 6 ) 2 , Si(SR 6 ) 2 , Zn and Mg, wherein R 5 and R 6 are selected from hydrogen, alkyl, aryl, heteroaryl, alkanoyl, arylcarbonyl, arylaminocarbonyl, trifluoroacetyl, ##STR60## groups of the formulae ##STR61## wherein R 7 , R 8 and R 9 are independently selected from alkyl, phenyl or phenyl substituted with alkyl, alkoxy or halogen; X is selected from oxygen, sulfur, selenium, tellurium or a group of the formula N-R 10 , wherein R 10 is hydrogen, cycloalkyl, alkyl, acyl, alkylsulfonyl, or aryl or R 10 and R taken together form an aliphatic or aromatic ring with the nitrogen atom to which they are attached; Y is selected from alkyl, aryl, heteroaryl, halogen or hydrogen; R is selected from hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, alkylene ##STR62## --(X-R) m is one or more groups selected from alkylsulfonylamino, arylsulfonylamino, or a group selected from the formulae --X(C 2 H 4 O) z R, ##STR63## wherein R is as defined above; Z is an integer of from 1-4; or two --(X-R) m groups can be taken together to form divalent substituents of the formula ##STR64## wherein each X 1 is independently selected from --O--, --S--, or --N-R 10 and A is selected from ethylene; propylene; trimethylene; and such groups substituted with lower alkyl, lower alkoxy, aryl and cycloalkyl; 1,2-phenylene and 1,2-phenylene containing 1-3 substituents selected from lower aklyl, lower alkoxy or halogen; R' and R" are independently selected from lower alkyl and cycloalkyl; R 1 and R 2 are independently selected from hydrogen, alkyl, alkoxy, halogen, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkylsulfonylamino, arylsulfonylamino, cycloalkylsulfonylamino, unsubstituted and substituted carbamoyl and sulfamyl, alkoxycarbonyl, cycloalkoxycarbonyl, alkanoyloxy, ##STR65## R 3 and R 4 are independently selected from hydrogen, lower alkyl, alkenyl or aryl; n is an integer from 0-16; n 1 is an integer from 0-24, m is an integer from 0-16; m 1 is an integer from 0-24; provided that the sums of n+m and n 1 +m 1 are 16 and 24, respectively.

Claim 28

The petroleum hydrocarbon of claim 23, wherein the near infrared fluorescing compound is a squaraine compound of Formula III, and wherein R 1 and R 2 are independently alkoxycarbonyl.

Claim 29

The petroleum hydrocarbon of claim 23, wherein the near infrared fluorescing compound is a 2,3-naphthalo-cyanine compound of Formula II, and wherein the naphthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOR 5 , SiCl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg, m 1 is 0, Y is alkyl and n 1 is 24 and wherein the Y groups represent at least four alkyl or aryl groups.

Claim 30

The petroleum hydrocarbon of claim 24, wherein the naphthalocyanine compound of Formula II is bonded to hydrogen.

Claim 31

The petroleum hydrocarbon of claim 24, wherein the near infrared fluorescing compound is a phthalocyanine compound of Formula I, and wherein X is oxygen, R is aryl or alkyl, Y is hydrogen, m is 4, and n is 12; and wherein the phthalocyanine moiety is bonded to hydrogen, AlCl, AlOH, AlOCOCF 3 , AlOR 5 , SiCl 2 , Si(OH) 2 , Si(OR 6 ) 2 , Zn or Mg.

Claim 32

The petroleum hydrocarbon of claim 24, wherein the phthalocyanine compound of Formula I is bonded to hydrogen.

Claim 33

The petroleum hydrocarbon of claim 24, wherein the near infrared fluorescing compound is selected from the group consisting of 1(4) , 8(11) , 15(18) , 22(25)-tetra[4(2-ethylhexyloxycarbonyl)phenylthio]PcH 2 ; 2(3), 9(10), 16(17), 23(24)-Tetra-(4-nonylphenoxy)PcH 2 ; 2(3), 9(10), 16(17), 23(24)-Tetra-(4-isoamylphenylthio)-PcZn; 2(3), 9(10), 16(17), 23(24)-tetra(2-ethylhexylamino)PcH 2 ; 2(3), 9(10), 16(17), 23(24)-tetra(3,5-di-t-butylphenoxy)PcH 2 ; 2(3), 9(10), 16(17), 23(24)-tetra[4-(carbo-2-ethylhexyloxy)phenoxy]PcH 2 ; 2(3), 9(10), 16(17), 23(24)-tetra (3-pentadecylphenoxy)-PcH 2 ; 2(3), 11(12), 20(21), 29(30)-tetra-t-butyl-NcH 2 ; 2(3), 11(12), 20(21), 29(30)-tetraactyl-NcH 2 ; and 2(3), 11(12), 20(21), 29(30)-tetra-t-butyl-NcZn; 1, 4, 8, 11, 15, 18, 22, 25-octabutoxy-PcH 2 ; 2(3), 9(10), 16(17), 23(24)-tetra(phenylthio)pcH 2 ; 2(3), 9(10), 16(17), 23(24)-tetra(4-t-butylphenylthio)pcH 2 ; 5, 9, 14, 18, 23, 27, 32, 36-octabutoxy-NcH 2 ; 5(36), 14(9), 23(18), 32(27)-tetra(4-t-butylphenyl)-3(2), 12(11), 21(20), 30(29)-tetra-t-butyl-NcH 2 ; 5(36), 14(9), 23(18), 32(27)-tetra-[4-(2-ethylhexylamino)phenyl]-3(2), 12(11), 21(20), 30(29)-tetra-(2-ethylhexylamino)NcH 2 ; wherein Pc is a phthalocyanine moiety and Nc is a naphthalocyanine moiety.

Claim 34

The petroleum hydrocarbon of claim 24 wherein the near infrared fluorescing compound is 2(3), 11(12), 20(21), 29(30)-tetra-t-butyl-NcH 2 , wherein Nc is a naphthalocyanine moiety.

Claim 35

The petroleum hydrocarbon of claim 23, wherein the near infrared flurophoric compound is non-metallated.