Irradiation detection and identification method and compositions useful therein

Claim 3

The method of claim 1 wherein each said luminophore moiety is selected from; 1, 2-diarylethenes; 2-arylbenzazoles; 2(H)-1-benozypyran-2-ones (coumarins); 2(H)-1-benzoypyrane-2-imines (iminocoumarins); carbostyrils; 3(H)-1-naphtho[2,1-b]pyran -3-ones; 3(H)-naphthos[2,1-b]pyran-3-imines; aminophthalimides; 1, 8-naphthalenedicarboximides; 1, 4, 5, 8-naphthalenetetracarboxylic acid diimides; 2, 5-diarylthiophenes; 2, 5-diarylfurans; 2,5 diaryl-1,3,4-thiadiazoles; 2-arylbenzofurans; 2, 6-diphenylbenzodifurans; 2, 2-bis(5-phenyl-1,3,4-oxadiazoles); quinolines; quinoxalines; 3, 4diarylfuranones; distyrylarenes; 7(H)-benzanthracene-7-ones(benzanthrones); or polyarenes; and wherein Y is a poly(oxyalkylene) moiety comprised of at least 50 mole percent of monomeric units or mixtures thereof of the formula (-RO-) wherein R is selected from substituted or unsubstituted straight chain alkylenes of two to four carbons; wherein X linking moiety is selected from a convalent bond, --O--, --S--, --SO 2 --, --CON(R 1 )--, --SO 2 N(R 1 )--, --COO--, --N(R 2 )--, or 1, 3, 5-triazin-2, 4-diylamino; wherein R 1 is selected from hydrogen, Y, unsubstituted or substituted alkyl; unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; wherein R 2 is R 1 or --SO 2 R 3 ; wherein R 3 is selected from unsubstituted or substituted alkyl, cycloalkyl or phenyl.

Claim 4

The method of claim 2 wherein the luminescent compound is selected from compounds of the formulae; ##STR523## wherein R 4 and R 4' are independently selected from phenyl or phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, halogen, cyano, -X-Y, unsubstituted or substituted sulfamoyl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, benzofuran-2-yl, isoxazol-2-yl, 1,2-benzisoxazol-3-yl, pyrazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 1,3,5-triazin-5-yl, 2(H)-tetrazol-5-yl, pyrimidin-2-yl, benzotriazol-2-yl, naphthotriazol-2-yl, or trifluoromethyl; benzoxazol-02-yl; benzothiazol-2-yl, benzimidazol-2-yl; benzotriazol-2-yl; 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazol-2-yl and these azole moieties substituted with lower alkyl, lower alkoxy, phenyl, arylene-X-Y, -O-arylene-X-Y, -X-Y, lower alkylthio, cyano, carboxylate ester, unsubstituted or substituted carbamoyl, benzoxazol-2-yl, benzothiazol-2-yl or 1,3,4-oxadiazol-2-yl; wherein R 5 is selected from groups listed above for R 4 or an optionally substituted electron rich aryl moiety derived from anilines, 1,2,3,4-tetrahydroquinolines, 3,4,-dihydro-2(H)-1,4-benzoxazines, 2,3-dihydroindoles, naphthylamines, 2-aminthiazoles, carbazoles, indoles, phenoxazines, phenothiazines, thiophenes, furans, julolidines, 2,3,3-trimethylinodolenines, diphenylamines, 3-cyano-2,6-diamino-4-methylpyridines, pyrazoles, pyrroles, oxybenzenes, thiobenzenes or oxynaphthalenes; wherein R 6 is selected from hydrogen, -X-Y, alkylene-X-Y, alkylene-X-Y, arylene-X-Y, -O-arylene-X-Y, lower alkyl, lower alkoxy, halogen, phenyl, cyano, carboxylate ester, unsubstituted or substituted carbamoyl, unsubstituted or substituted sulfamoyl, trifluoromethyl, alkylthio, alkylsulfonyl, benzoxazol-2-yl, benzothiazol-2-yl, 1,3,4-oxadiazol-2-yl; wherein Z is selected from --O--, --S--, --SO 2 --, --N(R 1 )--; wherein R 7 is selected from --X--Y; hydrogen; hydroxy; hyroxyalkoxy; lower alkyl; lower alkoxy; amino; amino substituted optionally with alkyl, cycloalkyl, phenyl or 1,3,5-triazin-2-yl; 1,2,3,-triazol-2-yl; benzoxazol-2-yl; benzotriazol-2-yl; pyrazol-1-yl; naphtho[1,2,-d]triazol-2-yl; alkylene-X-Y; arylene-X-Y; -O-alkylene-X-Y or -O-arylene-X-Y; wherein R 8 is selected from hydrogen; -X-Y; lower alkyl; cyano; unsubstituted or substituted carbamoyl; unsubstituted or substituted sulfamoyl; alkylsulfonyl; arylsulfonyl; carboxylate ester; aryl moiety selected from phenyl; naphthyl, thienyl, furanyl, benzofuran-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, and these aryl moieties substituted with -X-Y, lower alkyl, lower alkoxy, carboxylate ester, carbamoyl, phenyl, or halogen; wherein A is selected from ═O or ═N--R 1 ; wherein R 9 is hydrogen or one or more groups selected from -X-Y, lower alkyl, alkoxy, hydroxy, halogen or hydroxyalkoxy; wherein R 10 is selected from -Y, alkylene-X-Y, arylene-X-Y, alkylenearylene-X-Y, or R 1 ; wherein R 11 is hydrogen or 1-2substituents selected from lower alkyl, lower alkoxy or halogen; wherein R 12 and R 13 are independently selected from hydrogen, acyl, 1,3,5-triazin-2-yl, alkylene-X-Y, arylene-X-Y, or substituents represented by R 1 ; wherein R 14 and R 15 are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen, acylamino, aryloxy, alkylthio, arylthio, carbalkoxy, cyano, -O-alkylene-X-Y; -O-arylene-X-Y, -S-arylene-X-Y, -O-alkylenearylene-X-Y, -O-alkylene-O-arylene-X-Y, or 1,3,5-triazin-2-ylamino; wherein R 16 and R 17 are hydrogen or one or more groups selected from lower alkyl, lower alkoxy, carbalkoxy, halogen, cyano, unsubstituted or substituted sulfamoyl, alkylsulfonyl or -X-Y; wherein R 18 is selected from hydrogen, lower alkyl, aralkyl, aryl, alkoxy, cyano or substituted or substituted sulfamoyl; wherein R 19 is selected from hydrogen, lower alkyl, lower alkoxy, carbalkoxy, halogen, 1,3,5-triazin-2-ylamino, naphtho[1,2-d]triazol-2-yl, pyrazalo[3,4-d]1,2,3,-triazol-2-yl, benzotriazol-2-yl or halogen; wherein R 20 is selected from hydrogen or lower alkyl; wherein R 21 is selected from hydrogen, alkyl, alkoxy, halogen or -X-Y; wherein R 22 is selected from hydrogen, cyano, carboxylate ester, alkylsulfonyl, acyl, unsubstituted or substituted sulfamoyl, unsubstituted or substituted carbamoyl, --SO 2 (R 1 )Y, or --CON(R 1 )Y; wherein R 23 is selected from -X-Y; wherein R 24 is selected from hydrogen, lower alkyl, lower alkoxy or halogen; wherein R 25 is selected from 1,4-phenylene; 1,4-phenylene substituted with lower alkyl, lower alkoxy, halogen, cyano, carboxylate ester, unsubstituted or substituted carbamoyl or alkylsulfonyl; biphenylene; terphenylene; dibenzofuran-3,8-diyl; 1,3,4-oxadiazol-2,5-diyl; 1,3,4-thiadiazol-2,5,-diyl; naphthalene-1,4,-diyl; wherein R 26 and R 27 are independently selected from phenyl or phenyl substituted with one or more groups selected from hydrogen, lower alkyl, lower alkoxy, halogen, cyano, hydroxy, amino, amino substituted optionally substituted with alkyl, cycloalkyl or phenyl; 1,3,5,-triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl; unsubstituted or substituted carbamoyl; or -X-Y; wherein; Ar is one or more fused aromatic moieties selected from naphthalenes, acenaphthenes, anthracenes, phenanthrenes, perylenes, fluorenes, triphenylenes, pyrenes, chrysenes, naphthacenes, 1,2-benzanthrenes, 2,3-benzanthracenes, 1,12-benzoperylenes, 3,4-benzopyrenes, 4,5-benzopyrenes, decacylenes, carbazoles, indoles, 2,3-benzofurans, dibenzofurans, 2,3-benzothiophenes, dibenzothiophenes, dibenzothiophene dioxides, phenothiazines, phenoxazines or non-fused polyaromatic moieties selected from biphenyls, terphenyls, quaterphenyls, or binaphthyls; wherein R 28 and R 29 are independently selected from hydrogen; lower alkyl; lower alkoxy; acyl; halogen; cyano; hydroxy; amino; amino substituted optionally substituted with alkyl, cycloalkyl, or phenyl; 1,3,5triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl; unsubstituted or substituted carbamoyl or -X-Y; with the proviso that at least one -X-Y group be present in the structure.

Claim 5

The method of claim 3 wherein the 2-arylbenzazole has the following structure: ##STR524## wherein: R 5 is an electron rich aromatic moiety selected from the following structures: ##STR525## wherein: R 30 and R 31 are selected from hydrogen; Y (as defined above); straight or branched lower alkenyl; cycloalkyl; cycloalkyl substituted with hydroxy, alkoxy, halogen or alkanoyloxy; phenyl; phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano, alkylanoyloxy or -X-Y (as defined above); straight or branched chain alkyl of 1-12 carbons and such alkyl substituted with one or more of the following: -X-Y; groups of the following formula: ##STR526## wherein X and Y are as defined above; wherein R 44 is selected from hydrogen; lower alkyl; lower alkoxy; halogen; lower alkanoylamino; cycloalkyl; cycloalkyl substituted with hydroxy, alkoxy, halogen, or alkanoyloxy; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, alkanoylamino, carboalkoxy, carboxy, hydroxy, cyano, or alkanoyloxy; groups of the formulae: --OR 45 , --SO 2 R 46 , --CON(R 45 ) (R 47 ), --SO 2 N(R 45 ) (R 47 ), --N(R 45 )SO 2 R 46 , --O--X'--R 46 , --SR 48 , and --SO 2 C 2 H 4 SR 46 ; R 45 and R 47 are selected from hydrogen; lower alkyl; lower alkyl substituted with hydroxy, acyloxy, halogen, cycloalkyl, alkoxy, or phenyl; cycloalkyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano, or alkanoyloxy, wherein R 46 represents the same substituents listed for R 45 and R 47 excepting hydrogen; wherein X' is selected from --CO--, or --CON(R 45 )--; wherein R 48 is selected from the groups listed above for R 45 and R 47 plus benzothiazolyl, benzimidazolyl, pyridyl, pyrimidinyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, naphthyl, or triazolyl; cyano, halogen, 2-pyrrolidino, phthalimidino, vinylsulfonyl, acryamido, -o-benzoylsulfonimido, groups of the formula: ##STR527## wherein Q is lower alkylene of 1-3 carbons; lower alkylene substituted with hydroxy, halogen, alkoxy or acyloxy; vinyl; 1,2-phenylene; 1,2-phenylene substituted with lower alkyl; lower alkoxy, halogen, carboxy or carbalkoxy; 1,2-cyclohexylene; --O--CH 2 --; --CH 2 OCH 2 --; --S--CH 2 --; --N(R 45 )CH 2 --; --N(R 45 )CH 2 CH 2 -- or --CH 2 N(R 45 )CH 2 --; wherein R 30 and R 31 can be a single combined group such as pentamethylene, tetramethylene, ethyleneoxyethylene, ethylenesulfonylethylene, ethylenethioethylene, ethylene-N(R 45 )ethylene, ethylene-N(-X'-R 46 )ethylene, or ethylene(SO 2 R 47 )ethylene which, with the nitrogen to which it is attached, forms a ring; R 32 , R 38 , and R 39 are selected from hydrogen, chlorine, bromine, fluorine, iodine, lower alkyl, trifluoromethyl, lower alkoxy, alkoxy substituted with hydroxy, aryl, aryloxy, arylthio, alkylene-X-Y or -O-alkylene-X-Y; m and m' are 1 or 2; R 33 is selected from hydrogen, or one or two groups selected from R 30 or Y; R 34 , R 35 , and R 36 are each independently selected from hydrogen and lower alkyl; R 37 is hydrogen, lower alkyl, halogen, aryl, or -O-arylene-X-Y; R 40 and R 41 are selected from hydrogen, lower alkyl, lower alkoxy, halogen, hydroxy, or acyloxy; R 42 is selected from hydrogen, cyano, --COOR 45 , --CON(R 45 ) (R 47 ), --SO 2 R 46 , --COR 46 , or --CON(R 2 )--Y; R 43 is alkylene; arylene; aralkylene; alkyleneoxy; alkyleneoxyalkylene; alkylene; alkylene substituted with hydroxy, acyloxy, alkoxy, halogen, aryloxy, -X-Y, or -X-arylene-X-Y; L is a divalent single covalvent bond, --O(C═O)O--, --(C═O)--O--, --(C═O)--, --O--, --S--, --SO 2 --, --N(SO 2 R 46 )--, --S--S--, --O--(C═O)-alkylene-(C═O)--O--, --O(C═O)-arylene-(C═O)--O--, --O--(C═O)NH-alkylene-NH(C═O)--O--, --O(C═O)NH-arylene-NH(C═O)--O--, -O-alkylene-O-, -O-arylene-O-, cycloalkylene or arylene.

Claim 6

The method of claim 4 wherein said tagging compound is selected from those of the formulae: ##STR528## wherein each R is divalent ethylene, propylene, or butylene; each R 6 and R 54 is selected from alkyl of 1-8 carbons, alkoxy of 1-8 carbons, or halogen; each R 55 is selected from hydrogen, acyl of 1-8 carbons or alkyl of 1-8 carbons; and n+n' is an integer of from about 20 to 200.

Claim 7

The method of claim 4 wherein said tagging compound is selected from those of the formulae: ##STR529##

Claim 8

The method of claim 4 wherein said tagging compound is selected from those of the formulae: ##STR530##

Claim 9

The method of claim 3 wherein the 1,2-diarylethane has the following structure: R.sub.4 --CH═CH--R.sub.5 wherein: R 4 is selected from phenyl or phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, halogen, cyano, -X-Y, unsubstituted or substituted sulfamoyl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, benzofuran-2-yl, isoxazol-2-yl, 1,2-benzisoxazol-3-yl, pyrazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 1,3,5-triazin-5-yl, 2(H)-tetrazol-5-yl, pyrimidin-2-yl, benzotriazol-2-yl, naphtho[1,2-d]triazol-2-yl, or trifluoromethyl; benzoxazol-2-yl; benzothiazol-2-yl; benzimidazol-2-yl; benzotriazol-2-yl; 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazol-2-yl and these azole moieties substituted with lower alkyl, lower alkoxy, phenyl, phenylene-X-Y, -O-phenylene-X-Y, -X-Y, lower alkylthio, cyano, carboxylate ester, unsubstituted or substituted carbamoyl, benzoxazol-2-yl, benzothiazol-2-yl or 1,3,4-oxadiazol-2-yl; wherein R 5 is selected from the groups listed above in claim 4

Claim 10

The method of claim 3 wherein the coumarin has the following structure: ##STR531## wherein: R 7 is selected from -X-Y; hydrogen; hydroxy; hydroxyalkoxy; lower alkyl; lower alkoxy; amino; amino substituted optionally with alkyl, cycloalkyl, phenyl or 1,3,5-triazin-2-yl; 1,2,3-triazol-2-yl; pyrazol-1-yl; benzoxazol-2-yl; benzotriazol-2-yl; naphtho[1,2-d]triazol-2-yl; alkylene-X-Y; arylene-X-Y; -O-alkylene-X-Y; or -O-arylene-X-Y; wherein R 8 is selected from hydrogen; -X-Y; lower alkyl; cyano; unsubstituted or substituted carbamoyl; unsubstituted or substituted sulfamoyl; alkylsulfonyl;arylsulfonyl; carboxylate ester; aryl moiety selected from phenyl, naphthyl, thienyl, furanyl, benzofuran-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, and these aryl moieties substituted with -X-Y, lower alkyl, lower alkoxy, carboxylate ester, carbamoyl, phenyl, or halogen.

Claim 11

The method of claim 3 wherein the iminocoumarin has the following structure: ##STR532## wherein R 7 and R 8 are selected from the groups of claim 8 above.

Claim 12

The method of claim 3 wherein the aminophthalimide has the following structure: ##STR533## wherein: R 10 is selected from -Y, alkylene-X-Y, arylene-X-Y, alkylenearylene-X-Y, or R 1 (as defined in claim 1); wherein R 11 is selected from hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy or halogen; wherein R 12 and R 13 are independently selected from hydrogen, acyl, 1,3,5-triazin-2-yl, alkylene-X-Y, arylene-X-Y, or substituents represented by R 1 (as defined in claim 1).

Claim 13

The method of claim 3 wherein the 1,8naphthalenedicarboximide has the following structure: ##STR534## wherein: R 14 and R 15 are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen, acylamino, aryloxy, alkylthio, arylthio, carbalkoxy, cyano, -O-alkylene-X-Y, -O-arylene-X-Y, -S-arylene-X-Y, -O-alkylenearylene-X-Y, -O-alkylene-O-arylene-X-Y, or 1,3,5-triazin-2-ylamino; wherein wherein R 10 is selected from the groups of claim 10 above.

Claim 14

The method of claim 3 wherein the 1,4,5,8-naphthalenetetracarboxylic acid diimide has the following structure: ##STR535## wherein R 10 and R 11 are selected from the groups listed above.

Claim 15

The method of claim 3 wherein the 1,3-diphenyl-2-pyrazoline has the following structure: ##STR536## wherein: R 16 and R 17 are hydrogen or one or more groups selected from lower alkyl, lower alkoxy, carbalkoxy, halogen, cyano, unsubstituted or substituted sulfamoyl, alkylsulfonyl or -X-Y; wherein R 18 is selected from hydrogen, lower alkyl, aralkyl, aryl, alkoxy, cyano or unsubstituted or substituted sulfamoyl.

Claim 16

The method of claim 3 wherein the quinoline has the following structure: ##STR537## wherein R 7 , R 8 , and R 11 are selected from the groups listed above.

Claim 17

The method of claim 3 wherein the quinoxaline has the following structure: ##STR538## wherein R 6 , R 7 , and R 8 are selected from the groups listed above.

Claim 18

The method of claim 3 wherein the 7(H)-benz[d,e]anthracene-7-ones has the following structure: ##STR539## R 26 and R 27 are independently selected from phenyl or phenyl substituted with one or more groups selected from hydrogen, lower alkyl, lower alkoxy, halogen, cyano, hydroxy, amino, amino substituted optionally substituted with alkyl, cycloalkyl or phenyl; 1,3,5-triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl, unsubstituted or substituted carbamoyl, -Y or -X-Y.

Claim 19

The method of claim 3 wherein the polyarene has the following structure: R.sub.28 --Ar--R.sub.29 Ar is one or more fused aromatic moieties selected from naphthalenes, acenaphthenes, anthracenes, phenanthrenes, perylenes, fluorenes, triphenylenes, pyrenes, chrysenes, naphthacenes, 1,2-benzanthrenes, 2,3-benzanthracenes, 1,12-benzoperylenes, 3,4-benzopyrenes, 4,5-benzopyrenes, decacylenes, carbazoles, indoles, 2,3-benzofurans, dibenzofurans, 2,3-benzothiophenes, dibenzothiophenes, dibenzothiophene dioxides, phenothiazines, phenoxazines or non-fused polyaromatic moieties selected from biphenyls, terphenyls, quaterphenyls, or binaphthyls; wherein R 28 and R 29 are independently selected from hydrogen; lower alkyl; lower alkoxy; acyl; halogen; cyano; hydroxy; amino; amino; substituted optionally substituted with alkyl, cycloalkyl or phenyl; phenyl; 1,3,5-triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl; unsubstituted or substituted carbamoyl or -X-Y.

Claim 23

The method of claim 21 wherein said material, is a natural or synthetic fiber or yarn.

Claim 24

The method of claim 22 wherein said polymeric material is selected from polyvinyl alcohol, polyacrylic acid,acrylic polymers, carboxymethylcellulose, styrene-maleic anhydride copolymers, sulfopolyesters and starch.

Claim 26

The method of claim 1 wherein said material is solid, particulate, polymeric material.

Claim 27

The method of claim 1 wherein said material is thermoplastic.

Claim 28

The method of claim 1 wherein said material is thermosetting.

Claim 29

A material having markedly enhanced visibility under irradiation within the range of from about 300 to about 400 nm and comprising natural or synthetic material associated with one or more tagging compounds containing one or more non-ionic luminophore moieties linked to at least one poly(oxyalkylene) moiety, wherein said tagging compound has substantial absorbance within the range of from about 300 to about 400 nm and reemits substantial visible light.

Claim 30

A material having markedly enhanced visibility under irradiation within the range of from about 300 to about 400 nm and comprising natural or synthetic material associated with one or more tagging compounds containing one or more non-ionic luminophore moieties linked to at least one poly(oxyalkylene) moiety, wherein said tagging compound has substantial absorbance within the range of from about 300 to about 400 nm and reemits substantial visible light.

Claim 31

The material of claim 28 wherein said compound is affixed thereto by one or more binding agents selected from polyvinyl alcohol, polyacrylic acid, acrylic polymers, carboxymethylcellulose, styrene maleic anhydride copolymers, sulfopolyesters and starch.

Claim 32

The material of claim 29 wherein said luminescent moiety is selected from 1,2,-diarylethanes; 2-arylbenzazoles; 2(H)-1-benozpyran-2-ones (coumarins); 2(H)-1-benzopyrane-2-imines (iminocoumarins); carbostyrils; 3(H)-1-naphtho[2,1-b]pyran-3-ones; 3(H)-naphtho[2,1-b]pyran-3-imines; aminophthalimides; 1,8-naphthalenedicarboximides; 1,4,5,8-naphthalenetetracarboxylic acid diimides; 2,5-diarylthiophenes; 2,5-diarylfurans; 2,5-diaryl-1,3,4-thiadiazoles; 2,5-diaryl-1,3,4-oxadiazoles; 1,3-diphenyl-2-pyrazolines; 2-arylbenzofurans; 2,6-diphenylbenzodifurans; 2,2'-bis (5-phenyl-1,3,4-oxadiazoles); quinolines; quinoxalines; 3,4-diarylfuranones; distyrylarenes; 7(H)-benz[de]anthracene-7-ones(benzanthrones); or polyarenes.

Claim 33

The material of claim 30 comprising fiber or yarn.

Claim 34

A composition of matter having the empirical formula (L-X-Y) and comprised of one or more luminophore moieties (L) selected from: 1,2-diarylethanes; 2-arylbenzazoles; 2(H)-1-benzopyran-2-ones(coumarins); 2(H)-1-benzopyrane-2-imines (iminocoumarins); carbostyrils; 3(H)-1-naphtho[2,1-b]pyran-3-ones; 3(H)-naphtho[2,1-b]pyran-3 -imines; aminophthalimides; 1,8-naphthalenedicarboximides; 1,4,5,8-naphthalienetetracarboxylic acid diimides; 2,5-diarylthiophenes; 2,5-diarylfurans; 2,5-diaryl-1,3,4-thiadiazoles; 2,5-diaryl-1,3,4-oxadiazoles; 1,3-diphenyl-2-pyranzolines; 2-arylbenzofurans; 2,6-diphenylbenzodifurans; 2,2',bis(5-phenyl-1,3,4-oxadiazoles); quinolines; quinoxalines; 3,4-diarylfuranones; distyrylarenes; 7(H)-benzanthracene-7-ones(benzanthrones); or polyarenes; wherein each said (L) moiety is linked to at least one poly(oxyalkylene) moiety (Y) comprised of at least 50 mole percent of monomeric units or mixtures thereof the formula (--RO--), wherein R is selected from substituted or unsubstituted straight or branched chain alkylenes of two to four carbons; and wherein (L) is linked to (Y) through a linking moiety (X) selected from a covalent bond, --O--, --SO--, --SO 2 --, --CON(R 1 )--, --SO 2 N(R 1 )--, --COO--, --N(R 2 )--, or 1,3,5-triazin-2,4 diylamino; wherein R 1 is selected from hydrogen, Y, unsubstituted or substituted alkyl; unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; R 2 is selected from R 1 or --SO 2 R 3 ; and R 3 is selected from unsubstituted or substituted alkyl, cycloalkyl or phenyl.

Claim 35

A composition of matter having the empirical formula (L-X-Y) and comprised of one or more luminophore moieties (L) selected from: 1,2-diarylethanes; 2-arylbenzazoles; 2(H)-1-benzopyran-2-ones(coumarins); 2(H)-1-benzopyrane-2-imines (iminocoumarins); carbostyrils; 3(H)-1-naphtho[2,1-b]pyran-3-ones; 3(H)-naphtho[2,1-b]pyran-3 -imines; aminophthalimides; 1,8-naphthalenedicarboximides; 1,4,5,8-naphthalienetetracarboxylic acid diimides; 2,5-diarylthiophenes; 2,5-diarylfurans; 2,5-diaryl-1,3,4-thiadiazoles; 2,5-diaryl-1,3,4-oxadiazoles; 1,3-diphenyl-2-pyranzolines; 2-arylbenzofurans; 2,6-diphenylbenzodifurans; 2,2',bis(5-phenyl-1,3,4-oxadiazoles); quinolines; quinoxalines; 3,4-diarylfuranones; distyrylarenes; 7(H)-benzanthracene-7-ones(benzanthrones); or polyarenes; wherein each said (L) moiety is linked to at least one poly(oxyalkylene) moiety (Y) comprised of at least 50 mole percent of monomeric units or mixtures thereof the formula (--RO--), wherein R is selected from substituted or unsubstituted straight or branched chain alkylenes of two to four carbons; and wherein (L) is linked to (Y) through a linking moiety (X) selected from a covalent bond, --O--, --SO--, --SO 2 --, --CON(R 1 )--, --SO 2 N(R 1 )--, --COO--, --N(R 2 )--, or 1,3,5-triazin-2,4 diylamino; wherein R 1 is selected from hydrogen, Y, unsubstituted or substituted alkyl; unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; R 2 is selected from R 1 or --SO 2 R 3 ; and R 3 is selected from unsubstituted or substituted alkyl, cycloalkyl or phenyl.

Claim 36

A composition of matter of claim 32 comprising one or more luminescent moieties selected from the following general formulae: ##STR540## wherein R 4 and R 4' are independently selected from phenyl or phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, halogen, cyano, -X-Y, unsubstituted or substituted sulfamoyl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, benzofuran-2-yl, isoxazol-2-yl, 1,2-benzisoxazol-3-yl, pyrazol-1-yl, 1,2,3-triazol-2-yl, 1,2,4-oxadiazol-5yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,4-thiadiazol-5-yl, 1,3,5-triazin-5-yl, 2(H)-tetrazol-5-yl, pyrimidin-2-yl, benzotriazol-2-yl, naphtho[1,2-d]triazol-2-yl, or trifluoromethyl; benzoxazol-2-yl; benzothiazol-2-yl; benzimidazol-2-yl; benzotriazol-2-yl; 1,3,4-oxadiazol-2-yl; 1,3,4-thiadiazol-2-yl and these azole moieties substituted with lower alkyl, lower alkoxy, phenyl, arylene-X-Y, -O-arylene-X-Y, -X-Y, lower alkylthio, cyano, carboxylate ester, unsubstituted or substituted carbamoyl, benzoxazol-2-yl, benzothiazol-2-yl or 1,3,4-oxadiazol-2-yl; wherein R 5 is selected from the groups listed above for R 4 or an optionally substituted electron rich aryl moiety derived from anilines, 1,2,3,4-tetrahydroquinolines, 3,4-dihydro-2(H)-1,4-benzoxazines, 2,3,-dihydroindoles, naphthylamines, 2-aminthiazoles, carbazoles, indoles, phenoxazines, phenothiazines, thiophenes, furans, julolidines, 2,3,3,-trimethylindolenines, diphenylamines, 3-cyano-2,6-diamino-4-methylpyridines, pyrazoles, pyrroles, oxybenzenes, thiobenzenes or oxynaphthalenes; wherein R 6 is selected from hydrogen, -X-Y, alkylene-X-Y, alkylene-X-Y, arylene-X-Y, -O-arylene-X-Y, lower alkyl, lower alkoxy, halogen, phenyl, cyano, carboxylate ester, unsubstituted or substituted carbamoyl, unsubstituted or substituted sulfamoyl, trifluoromethyl, alkylthio, alkylsulfonyl, benzoxazol-2-yl, benzothiazol-2-yl, 1,3,4-oxadiazol-2-yl; wherein Z is selected from --O--, --S--, --SO 2 --, --N(R 1 )--; wherein R 7 is selected from -X-Y; hydrogen; hydroxy; hyroxyalkoxy; lower alkyl; lower alkoxy; amino; amino substituted optionally with alkyl, cycloalkyl, phenyl or 1,3,5-triazin-2-yl, 1,2,3-triazol-2-yl; benzoxazol-2-yl; benzotriazol-2-yl; pyrazol-1-yl; naphtho[1,2-d]triazol-2-yl; alkylene-X-Y; arylene-X-Y; -O-alkylene-X-Y or -O-arylene-X-Y; wherein R 8 is selected from hydrogen; -X-Y; lower alkyl; cyano; unsubstituted or substituted carbamoyl; unsubstituted or substituted sulfamoyl; alkylsulfonyl; arylsulfonyl; carboxylate ester; aryl moiety selected from phenyl, naphthyl, thienyl, furanyl, benzofuran-2-yl, benzoxazol-2-yl, benzothiazol-2-yl, benzimidazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, and these aryl moieties substituted with -X-Y, lower alkyl, lower alkoxy, carboxylate ester, carbamoyl, phenyl, or halogen; wherein A is selected from ═O or ═N--R 1 ; wherein R 9 is hydrogen or one or more groups selected from -X-Y, lower alkyl, alkoxy, hydroxy, halogen or hydroxyalkoxy; wherein R 10 is selected from -Y, alkylene-X-Y, arylene-X-Y, alkylenearylene-X-Y, or R 1 ; wherein R 11 is hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy or halogen; wherein R 12 and R 13 are independently selected from hydrogen, acyl, 1,3,5-triazin-2-yl, alkylene-X-Y, arylene-X-Y, or substituents represented by R 1 ; wherein R 14 and R 15 are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen, acylamino, aryloxy, alkylthio, arylthio, carbalkoxy, cyano, -O-alkylene-X-Y, -O-arylene-X-Y, -S-arylene-X-Y, -O-alkylenearylene-X-Y, -O-alkylene-O-arylene-X-Y, or 1,3,5-triazin-2-ylamino; wherein R 16 and R 17 are hydrogen or one or more groups selected from lower alkyl, lower alkoxy, carbalkoxy, halogen, cyano, unsubstituted or substituted sulfamoyl, alkylsulfonyl or -X-Y; wherein R 18 is selected from hydrogen, lower alkyl, aralkyl, aryl, alkoxy, cyano or unsubstituted or substituted sulfamoyl; wherein R 19 is selected from hydrogen, lower alkyl, lower alkoxy, carbalkoxy, halogen, 1,3,5-triazin-2-ylamino, naphtho[1,2-d]triazol-2-yl, pyrazalo[3,4-d]1,2,3-triazol-2-yl, benzotriazol-2-yl or halogen; wherein R 20 is selected from hydrogen or lower alkyl; wherein R 21 is selected from hydrogen, alkyl, alkoxy, halogen or -X-Y; wherein R 22 is selected from hydrogen, cyano, carboxylate ester, alkylsulfonyl, acyl, unsubstituted or substituted sulfamoyl, unsubstituted or substituted carbamoyl, --SO 2 (R 1 )Y, or --CON(R 1 )Y; wherein R 23 is selected from -X-Y; wherein R 24 is selected from hydrogen, lower alkyl, lower alkoxy or halogen; wherein R 25 is selected from 1,4-phenylene; 1,4-phenylene substituted with lower alkyl, lower alkoxy, halogen, cyano, carboxylate ester, unsubstituted or substituted carbamoyl or alkylsulfonyl; biphenylene; terphenylene; dibenzofuran-3,8-diyl; 1,3,4-oxadiazol-2,5-diyl; 1,3,4-thiadiazol-2,5-diyl; naphthalene-1,4-diyl; wherein R 26 and R 27 are independently selected from phenyl or phenyl substituted with one or more groups selected from hydrogen, lower alkyl, lower alkoxy, halogen, cyano, hydroxy, amino, amino substituted optionally substituted with alkyl, cycloalkyl or phenyl; 1,3,5-triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl; unsubstituted or substituted carbamoyl; or -X-Y; wherein; Ar is one or more fused aromatic moieties selected from naphthalenes, acenaphthenes, anthracenes, phenanthrenes, perylenes, fluorenes, triphenylenes, pyrenes, chrysenes, naphthacenes, 1,2-benzanthrenes, 2,3-benzanthracenes, 1,12-benzoperylenes, 3,4-benzopyrenes, 4,5-benzopyrenes, decacylenes, carbazoles, indoles, 2,3-benzofurans, dibenzofurans, 2,3-benzothiophenes, dibenzothiophenes, dibenzothiophene dioxides, phenothiazines, phenoxazines or non-fused polyaromatic moieties selected from biphenyls, terphenyls, quaterphenyls, or binaphthyls; wherein R 28 and R 29 are independently selected from hydrogen; lower alkyl; lower alkoxy; acyl; halogen; cyano; hydroxy; amino; amino substituted optionally substituted with alkyl, cycloalkyl, or phenyl; 1,3,5-triazin-2-yl; -O-alkylene-X-Y; -O-arylene-X-Y; -S-alkylene-X-Y; -O-alkylenearylen-X-Y; unsubstituted or substituted sulfamoyl; unsubstituted or substituted carbamoyl or -X-Y; with the proviso that at least one -X-Y group be present in the structure.

Claim 37

A composition of matter of claim 33 wherein said tagging compound is selected from 2-arylbenzazoles of the following structure: ##STR541## wherein: R 5 is an electron rich aromatic moiety selected from the following structures: ##STR542## wherein: R 30 and R 31 are selected from hydrogen, Y, straight or branched lower alkenyl; cycloalkyl; cycloalkyl substituted with hydroxy, alkoxy, halogen or alkanoyloxy; phenyl; phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano, alkylanoyloxy or -X-Y; straight or branched chain alkyl of 1-12 carbons and such alkyl substituted with one or more of the following: -X-Y, groups of the following formula: ##STR543## wherein R 44 is selected from hydrogen, lower alkyl, lower alkoxy, halogen, or lower alkanoylamino; cycloalkyl; cycloalkyl substituted with hydroxy, alkoxy, halogen, or alkanoyloxy; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, alkanoylamino, carboalkoxy, carboxy, hydroxy, carboalkoxy, cyano, or alkanoyloxy; groups of the formula: --OR 45 , --SO 2 R 46 , --CON(R 45 ) (R 47 ), --SO 2 N(R 45 ) (R 47 ), --N(R 45 )SO 2 R 46 , --O--X'--R 46 , --SR 48 , and --SO 2 C 2 H 4 SR 46 ; R 45 and R 47 are selected from hydrogen; lower alkyl; lower alkyl substituted with hydroxy, acyloxy, halogen, cycloalkyl, alkoxy, or phenyl; cycloalkyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano, or alkanoyloxy, wherein R 46 represents the same substituents listed for R 45 and R 47 excepting hydrogen, X' is selected from --CO--,--COO--, or --CON(R 45 )--; wherein R 48 is selected from the groups listed above for R 45 and R 47 plus benzothiazolyl, benzimidazolyl, pyridyl, pyrimidinyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, naphthyl, or triazolyl; cyano, halogen, 2-pyrrolidino, phthalimidino, vinylsulfonyl, acryamido, -o-benzoylsulfonimido, groups of the formula: ##STR544## wherein Q is lower alkylene of 1-3 carbons; lower alkylene substituted with hydroxy, halogen, alkoxy, or acyloxy; vinyl; 1,2-phenylene; 1,2-phenylene substituted with lower alkyl, lower alkoxy, halogen, carboxy or carbalkoxy; 1,2-cyclohexylene; --O--CH 2 --; --CH 2 OCH 2 --; --S--CH 2 --; --N(R 45 )CH 2 --; --N(R 45 )CH 2 CH 2 -- or --CH 2 N(R 45 )CH 2 --; wherein R 30 and R 31 can be a single combined group such as pentamethylene, tetramethylene, ethyleneoxyethylene, ethylenesulfonylethylene, ethylenethioethylene, ethylene-N(R 45 )ethylene, ethylene-N(--X'--R 46 )ethylene, or ethylene(SO 2 R 47 )ethylene which, with the nitrogen to which it is attached, forms a ring: R 32 , R 38 , and R 39 are selected from hydrogen, chlorine, bromine, fluorine, iodine, lower alkyl, trifluoromethyl, lower alkoxy, alkoxy substituted with hydroxy, aryl, aryloxy, arylthio, alkylene-Z-Y or -O-alkylene-X-Y; m and m' are 1 or 2; R 33 is selected from hydrogen, or one or two groups selected selected from R 30 or Y; R 34 , R 35 , and R 36 are each independently selected from hydrogen and lower alkyl; R 37 is hydrogen, lower alkyl, halogen, aryl, or -O-arylene-X-Y; R 40 and R 41 are selected from hydrogen, lower alkyl, lower alkoxy, halogen, hydroxy, or acyloxy; R 42 is selected from hydrogen, cyano, --COOR 45 , --CON(R 45 ) (R 47 ), --SO 2 R 46 , --COR 46 , or --CON(R 2 )-Y; R 43 is alkylene; arylene; aralkylene; alkyleneoxy; alkyleneoxyalkylene; alkylene; alkylene substituted with hydroxy, acyloxy, alkoxy, halogen, aryloxy, -X-Y, or -X-arylene-X-Y; L is a divalent single covalvent bond, --O(C═O)O--, --(C═O)--O-- --(C═O)--, --O--, --S--, --SO 2 --, --N(SO 2 R 46 )--, --S--S--, --O--(C═O)-alkylene-(C═O)--O--, --O(C═O)-arylene-(C═O)--O--, --O--(C═O)NH-alkylene-NH(C═O)--O--, --O(C═O)NH-arylene-NH(C═O)--O--, --O--alkylene-O-, -O-arylene-O-, cycloalkylene or arylene.

Claim 38

A composition of matter of claim 33 wherein said tagging compounds is selected from those of the formulae: ##STR545## wherein each R is divalent ethylene, propylene, or butylene; each R 6 and R 54 is selected from alkyl of 1-8 carbons, alkoxy of 1-8 carbons, or halogen; each R 55 is selected from hydrogen, acyl of 1-8 carbons or alkyl of 1-8 carbons; and n+n' is an integer of from about 20 to 200.