Method for detecting and separating thermoplastic containers with near infrared fluorosphores

Claim 1

A method for detecting and separating thermoplastic containers, said containers comprising a thermoplastic material having admixed therein or copolymerized therein a compound or residue having detectible fluorescence when exposed to near infrared radiation, which comprises the following steps: (a) exposure of a mixture of thermoplastic containers to near infrared radiation having wavelengths of about 670-2,500 nm, with the provision that at least one of said thermoplastic container compositions has admixed therein or copolymerized therein one or more near infrared tagging compounds or copolymerized residues having substantial near infrared absorbance and which is (are) present in sufficient quantity to impart fluorescence when exposed to radiation having wavelengths of about 670-2,500 nm, provided by light sources; (b) detection of the emitted (fluorescent) light via near infrared light detection means; and (c) separating the fluorescing containers from the non-fluorescing containers or containers flourescing at a detectibly different wavelength or wavelengths by mechanical means; wherein the near infrared fluorescing compound or residue thereof is selected from the classes of phathalocyanines, naphthalocyanines and squaraines and correspond to Formulae II, III and IV: ##STR42## wherein Pc and Nc represent the phthalocyanine and 2,3-naphthalocyanine moieties of Formulae IIa and IIIa, ##STR43## respectively, covalently bonded to hydrogen or to various metals, halometals, organometallic groups, and oxymetals selected from the group consisting of AlCl, AlBr, AlF, AlOH, AlOR 5 , AlSR 5 , Ca, Co, CrF, Cu, Fe, Ge, Ga, InCl, Mg, Mn, Ni, Pb, Pt, Pd, SiCl 2 , SiF 2 , SnCl 2 , Sn(OR 6 ) 2 , Si(OR 6 ) 2 , Sn(SR 6 ) 2 , Si(SR 6 ) 2 , Sn, TiO, VO and Zn, wherein R 5 and R 6 are selected from hydrogen, alkyl, aryl, lower alkanoyl, trifluoroacetyl or groups of the formulae ##STR44## R 7 , R 8 and R 9 are independently selected from alkyl, phenyl or phenyl substituted with lower alkyl, lower 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, halogen or hydrogen; R is selected from unsubstituted alkyl or substituted alkyl selected from the group consisting of alkyls containing 1-12 carbon atoms and containing as substituents 1 or 2 groups selected from hydroxy, halogen, carboxy, cyano, C 1 -C 4 alkoxy, aryl, C 1 -C 4 alkylthio, arylthio, aryloxy, C 1 -C 4 alkoxycarbonyl, or C 1 -C 4 alkanoyloxy, alkenyl, alkynyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, ##STR45## or --(X--R) m is alkylsulfonylamino, arylsulfonylamino, or a group selected from the formulae --X(C 2 H 4 O) z R 1 ##STR46## wherein R 1 is hydrogen or R 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 ##STR47## 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 C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl and cycloalkyl; 1,2-phenylene and 1,2-phenylene containing 1-3 substituents selected from C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; R 1 and R 2 are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen, aryloxy, lower alkylthio, arylthio, lower alkylsulfonyl; arylsulfonyl; lower alkylsulfonylamino, arylsulfonylamino, cycloalkylsulfonylamino, carboxy, unsubstituted carbamoyl and substituted carbamoyl selected from the group consisting of a radicals having the formula --CONR 12 R 13 , wherein R 12 and R 13 are selected from unsubstituted or substituted alkyl, alkenyl, alkynyl as defined above, cycloalkyl, aryl, or heteroaryl, and unsubstituted sulfamoyl and substituted sulfamoyl selected from the group consisting of radicals having the formula --SO 2 NR 12 R 13 , wherein R 12 and R 13 are as defined above, lower alkoxycarbonyl, hydroxy or lower alkanoyloxy, ##STR48## R 3 and R 4 are independently selected from hydrogen, lower alkyl, alkenyl or aryl; n is an integer from 0-12; n 1 is an integer from 0-24, m is an integer from 4-16; m 1 is an integer from 0-16; provided that the sums of n+m and n 1 +m 1 are 16 and 24, respectively.

Claim 2

A method for detecting and separating thermoplastic containers, said containers comprising a thermoplastic material having admixed therein or copolymerized therein a compound or residue having detectible fluorescence when exposed to near infrared radiation, which comprises the following steps: (a) exposure of a mixture of thermoplastic containers to near infrared radiation having wavelengths of about 670-2,500 nm, with the provision that at least one of said thermoplastic container compositions has admixed therein or copolymerized therein one or more near infrared tagging compounds or copolymerized residues having substantial near infrared absorbance and which is (are) present in sufficient quantity to impart fluorescence when exposed to radiation having wavelengths of about 670-2,500 nm, provided by light sources; (b) detection of the emitted (fluorescent) light via near infrared light detection means; and (c) separating the fluorescing containers from the non-fluorescing containers or containers flourescing at a detectibly different wavelength or wavelengths by mechanical means; wherein the near infrared fluorescing compound or residue thereof is selected from the classes of phathalocyanines, naphthalocyanines and squaraines and correspond to Formulae II, III and IV: ##STR42## wherein Pc and Nc represent the phthalocyanine and 2,3-naphthalocyanine moieties of Formulae IIa and IIIa, ##STR43## respectively, covalently bonded to hydrogen or to various metals, halometals, organometallic groups, and oxymetals selected from the group consisting of AlCl, AlBr, AlF, AlOH, AlOR 5 , AlSR 5 , Ca, Co, CrF, Cu, Fe, Ge, Ga, InCl, Mg, Mn, Ni, Pb, Pt, Pd, SiCl 2 , SiF 2 , SnCl 2 , Sn(OR 6 ) 2 , Si(OR 6 ) 2 , Sn(SR 6 ) 2 , Si(SR 6 ) 2 , Sn, TiO, VO and Zn, wherein R 5 and R 6 are selected from hydrogen, alkyl, aryl, lower alkanoyl, trifluoroacetyl or groups of the formulae ##STR44## R 7 , R 8 and R 9 are independently selected from alkyl, phenyl or phenyl substituted with lower alkyl, lower 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, halogen or hydrogen; R is selected from unsubstituted alkyl or substituted alkyl selected from the group consisting of alkyls containing 1-12 carbon atoms and containing as substituents 1 or 2 groups selected from hydroxy, halogen, carboxy, cyano, C 1 -C 4 alkoxy, aryl, C 1 -C 4 alkylthio, arylthio, aryloxy, C 1 -C 4 alkoxycarbonyl, or C 1 -C 4 alkanoyloxy, alkenyl, alkynyl, C 3 -C 8 cycloalkyl, aryl, heteroaryl, ##STR45## or --(X--R) m is alkylsulfonylamino, arylsulfonylamino, or a group selected from the formulae --X(C 2 H 4 O) z R 1 ##STR46## wherein R 1 is hydrogen or R 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 ##STR47## 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 C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl and cycloalkyl; 1,2-phenylene and 1,2-phenylene containing 1-3 substituents selected from C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen; R 1 and R 2 are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen, aryloxy, lower alkylthio, arylthio, lower alkylsulfonyl; arylsulfonyl; lower alkylsulfonylamino, arylsulfonylamino, cycloalkylsulfonylamino, carboxy, unsubstituted carbamoyl and substituted carbamoyl selected from the group consisting of a radicals having the formula --CONR 12 R 13 , wherein R 12 and R 13 are selected from unsubstituted or substituted alkyl, alkenyl, alkynyl as defined above, cycloalkyl, aryl, or heteroaryl, and unsubstituted sulfamoyl and substituted sulfamoyl selected from the group consisting of radicals having the formula --SO 2 NR 12 R 13 , wherein R 12 and R 13 are as defined above, lower alkoxycarbonyl, hydroxy or lower alkanoyloxy, ##STR48## R 3 and R 4 are independently selected from hydrogen, lower alkyl, alkenyl or aryl; n is an integer from 0-12; n 1 is an integer from 0-24, m is an integer from 4-16; m 1 is an integer from 0-16; provided that the sums of n+m and n 1 +m 1 are 16 and 24, respectively.