Reworkable thermosetting resin composition

Abstract

This invention relates to thermosetting resin compositions useful for mounting onto a circuit board semiconductor devices, such as CSPs, BGAs, LGAs and the like, each of which having a semiconductor chip, such as LSI, on a carrier substrate. The compositions of this invention are reworkable when subjected to appropriate conditions.

1 . A thermosetting resin composition, said composition comprising: 
 (a) a curable resin component, at least a portion of which is a compound having at least one linkage selected from the group consisting of oxiranes and thiiranes, substituted on at least three of the substitutable positions on the oxirane or thiirane carbons, respectively, with an alkyl, alkenyl or aryl substituent having a carbon content of 1 to about twelve carbon atoms, with or without substitution or interruption by one or more heteroatoms or halogens (I); and    (b) a curing agent component selected from the group consisting of anhydride compounds, amine compounds, amide compounds, imidazole compounds, and combinations thereof, provided that the compound I does not include as its sole component an epoxy compound within any of the following formulae [II:                          II    wherein each R is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, C 1-4  alkoxy, halogen, cyano and nitro, R 1  and R 2  are each independently selected from the group consisting of hydrogen, methyl, ethyl, and propyl, provided that both R 1  and R 2  cannot be hydrogen, and R 3  is independently selected from propyl, and isopropyl, provided at least one of R 3a  and R 3b , and at least one of R 3 c and R 3d  is independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl, and m is 0 or 1]                         wherein each R is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert butyl, C 1-4  alkoxy, halogens, cyano, nitro, and phenyl, and R 3  and R 4  together form an epoxy group, and R 1  and R 2  are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, and phenyl, except that at least one of R 1  and R 2  is not hydrogen, and n is 0 and p is 0 and m is 0 or 1, and the compounds are symmetrical;                          wherein R, R 1 , R 2 , R 3 , and R 4  are as defined above and m is 1 and p is 1 and n is 1 or p is 0 and m is 0 and n is 1, and the compounds are symmetrical;                          wherein R is defined as above, and the compounds are symmetrical; and                          wherein R, R 1  and R 2  are defined as above and c and d are both 1 or c and d are both 0, and the compounds are symmetrical, and wherein reaction products of the composition soften and lose their adhesiveness under exposure to temperature conditions in excess of those used to cure the composition.    
     
     
         2 . (canceled)  
     
     
         3 . The composition according to  claim 1 , wherein the curable resin component includes a compound having at least one oxirane linkage substituted on at least three of the substitutable positions on the oxirane carbons with an alkyl, alkenyl or aryl substituent having a carbon content of 1 to about twelve carbon atoms, with or without substitution or interuption by one or more heteroatoms or halogens.  
     
     
         4 . The composition according to  claim 3 , wherein the compound having at least one oxirane linkage is a member selected from the group consisting of oxiranes prepared from 2,10-dimethyl-6-methylene-4,8-bis(2-methyl-1-propenyl 2,4,7,9-undecatetraene, 4-[(4E or 4Z)-1,5-dimethyl-4-heptenylidene or octenylidene]-1-methyl-cyclohexene, 1,1′-[(1E or 1Z, 3E or 3Z)-5-(1,1-dimethyl-2-propenyl)-3-(3-methyl-2-butenyl)-1,3-pentadiene-1,5-diyl]bis-benzene, 4,6-dimethyl-[S or R-(E or Z, Z or E)]-2,5-octadiene, 2,6,10,14-tetramethyl-7-(3-methyl-4-pentenyl)-2,5,9,13-pentadecatetraene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z, 10Z or 10E)-1,3,6,10-tridecatetraene, 3,4,8-trimethyl-1,4,7-nonatriene, 13-ethyl-9-methyl-1,9,12-pentadecatetraene, 1-methyl-4-(2-methyl-6-heptenylidene)-cyclohexene, 2,6,11-trimethyl-(E or Z)-2,5,10-dodecatriene, 2,6-dimethyl-(E or Z, E or Z)-2,6,9-tetradecatriene, 7-(3-methyl-2-butenyl-(E or Z)-6-dodecene, 6-(3-methyl-2-butenyl)-(E or Z)-6-dodecene, 2,4,6,6,8-pentamethyl-2,4,7-nonatriene, 3,7-dimethyl-11-(methyl)-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 5-[3-methyl-1-(2-methyl-1-propenyl)-2-butenylidene]-1,3-cyclopentadiene, 4-[(4E or 4Z)-1,5-dimethyl-4-heptenylidene]-1-methyl-(4Z or 4E)-cyclohexene, 3,7,11-trimethyl-1,3,6,10-docosatetraene, 3,7,11,15-tetramethyl-1,3,6,10-hexadecatetraene, 9-ethyl-2,6-dimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2-methyl-5-propyl-(E or Z)-2,5-nonadiene, 3,7,11-trimethyl-(Z or E, E or Z, E or Z)-1,3,6,10-dodecatetraene, 4,8,12-trimethyl-(Z or E, E or Z, E)-2,4,7,11-tridecatetraene, 1-methyl-4-(2-methyl-6-heptenylidene)-(E or Z)-cyclohexene, 3-ethyl-7,11-dimethyl-(E or Z, E or Z)-1, 3, 6, 10-dodecatetraene, 2,6,6,9-tetramethyl-7-(2-methyl-1-propenyl)-2,4,8-decatriene, 2,7-dimethyl-4,5-bis(2-methyl-1-propenyl)-2,6-octadiene, 3,7-dimethyl-1,3,6-octatriene, 2-methyl-5-(1-methylethylidene)-cyclohexene, 2,6-dimethyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 2,6-dimethyl-2,5-decadiene or octadiene, 7-ethyl-3,11-dimethyl-1,3,6,10-dodecatetraene, 2-methyl-(E or Z)-2,5-octadiene, 7-ethyl-3,11-dimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 2,7,11-trimethyl-(E or Z)-2,5,10-dodecatriene, 6,10-dimethyl-(Z or E, Z or E)-2,6,9-undecatrien-4-yne, 2,6-dimethyl-(Z or E)-2,5-dodecadiene, 2,7-dimethyl-4,5-bis(2-methyl-1-propenyl)-2,4,6-octatriene, 2,3,6,7-tetramethyl-1,3,6-octatriene, 2-methyl-5-propyl-(Z or E)-2,5-dodecadiene, 2-methyl-5-(1-methylethyl)-(E or Z)-2,5-dodecadiene, 2-methyl-(Z or E)-2,5-dodecadiene, 2,4,4-trimethyl-(E or Z)-2,5-heptadiene, 2,6-dimethyl-2,5-octadiene, 3,4,7,11-tetramethyl-(E or Z, Z or E)-1,3,6,10-dodecatraene, 3,7,11-trimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 4,8-dimethyl-1,4,7-nonatriene, 3,7,11,15-tetramethyl-1,3,6,10,14-hexadecapentaene, 2-methyl-(Z or E)-2,5-pentadecadiene, 2-methyl-5-(1-methylethylidene)-2-decene, 2,6-dimethyl-2,5,7-decatriene, 4,8-dimethyl-2,4,7-nonatriene, 15,19,23-trimethyl-15,18,22-heptatriacontatriene, 8-(2-methyl-1-propenyl)-6-tetradecene, 3,7,11-trimethyl-(E or Z)-1,3,6,10-dodecatetraene, 3,4-didehydro-2-(3-methyl-2-butenyl)-carotene, 7-ethyl-3,11-dimethyl-1,3,6,10-dodecatetraene, 1,3-dimethyl-4-propylidene-cyclopentene, 2,7,11-trimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 6,10-dimethyl-1,4,6,9-undecatetraene, 2-(1-methylethyl)-5-(1-methylethylidene)-1,3-cyclohexadiene, 2-ethyl-5-ethylidene-cyclohexadiene, 2-methyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 3,7,10-trimethyl-(Z or E, E or Z)-1,3,6-undecatriene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, 1-methyl-4-(1-methylethylidene)-cyclohexene, 2,5-dimethyl-(Z or E)-2,5-heptadiene, 2-methyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 2,6,10-trimethyl-(E or Z, Z or E)-2,6,9-tetradecatriene, 6-methyl-(Z or E, E or Z)-2,5-dodecadiene, 2,3,6-trimethyl-(E or Z, E or Z)-1,3,6-octatriene, tetrahydro-3,7,11-trimethyl-1,3,6,10-dodecatetraene, 3,4,7,11-tetramethyl-1,3,6,10-dodecatetraene, 3,4,7,11-tetramethyl-(Z or E, Z or E)-1,3,6,10-dodecatetraene, 2,6-dimethyl-4-methylene-2,5-heptadiene, 5-ethyl-2-methyl-2,5-heptadiene, 2,5-dimethyl-2,5-heptadiene or octadiene, 3,7,11-trimethyl-dodecatriene, 2,4,6,6,8-pentamethyl-(E or Z)-2,4,7-nonatriene, 3,7-diethyl-11-methyl-1,3,6,10-tridecatetraene, 7-ethyl-3,11-dimethyl-1,3,6,10-tridecatetraene, 2,6-dimethyl-(E or Z)-2,5-dodecadiene, 2,6,10-trimethyl-(E or Z, E or Z)-2,6,9-tetradecatriene, 3,7,11,15-tetramethyl-(Z or E, E or Z, E or Z)-1,3,6,10,14-hexadecapentaene, 3,7,11,15-tetramethyl-(3E or 3Z, 6E or 6Z, 10E or 10Z)-1,3,6,10,14-hexadecapentaene, 1-ethenyl-4-(1-methylethylidene)-cyclohexene, 1-methyl-6-methylene-4-(1-methylethylidene)-cyclohexene, 3,7,11-trimethyl-1,3,6-dodecatriene, 4-(1,5-dimethylhexylidene)-1-methyl-cyclohexene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z)-1,3,6,10-dodecatetraene, 1,3,3′,4,4′,16-hexadehydro-1,2-dihydro-2,2′-bis-3-carotene, 7-methyl-(Z or E, Z or E)-3,6-dodecadiene, 6-ethylidene-2,3,10-trimethyl-(E or Z, E or Z)-1,3,9-undecatriene, 2,3,6,7,10,11-hexamethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 2,3,6,7-tetramethyl-(E or Z)-1,3,6-octatriene, 2,7,11-trimethyl-1,3,6,11-dodecatetraene, 3,7,11,15,19,23,27,31,35-nonamethyl-1,3,6,10,14,18,22,26,30,34-hexatriacontadecaene, 2,6-dimethyl-9-propyl-2,6,9-tridecatriene, 3,6-dimethyl-(E or Z, E or Z)-1,3,6-octatriene, 3,7-diethyl-11-methyl-(3Z or 3E, 6E or 6Z) 1,3,6,10-tridecatetraene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z)-1,3,6,10-tridecatetraene, 1-methyl-4-(5-methyl-4-hexenylidene)-(4E or 4Z)-cyclohexene, 2,6,10-trimethyl-(Z or E)-2,5,9-undecatriene, 2,6,7,7-tetramethyl-(Z or E)-2,5-octadiene, 2,6,10,11,11-pentamethyl-2,6,9-dodecatriene, 2,6,10-trimethyl-2,6,9-tetradecatriene, 2,6-dimethyl-(Z or E)-2,5-decadiene, 6,10-dimethyl-1,6,9-undecatrien-4-yne, 2,3,6-trimethyl-2,5-heptadiene, 2,4-dimethyl-(E or Z)-2,5-heptadiene, 2,7,11-trimethyl-(E or Z, E or Z)-1,3,6,11-dodecatetraene, 6-ethyl-3-methyl-2,5-decadiene, 2,6,10-trimethyl-(Z or E)-2,5-undecadiene, 3,7-dimethyl-3,6-octadien-1-yne, 2,7,10-trimethyl-1,6,9-undecatriene, 4,5-dimethyl-(E or Z, E or Z, E or Z)-3,5,8-undecatriene, 4,5-dimethyl-2,5,8-undecatriene, 1′-[4-methyl-2-(2-methyl-1-propenyl)-1,3-pentadienylidene]bis-benzene, 1,4-(1,5-dimethyl-4-hexenylidene)-1-methyl-(4E or 4Z)-cyclohexene, 2,6,11,15-tetramethyl-(Z or E)-2,6,9,14-hexadecatetraene, [3-methyl-1-(2-methyl-1-propenyl)-2-butenyl]-benzene, 2,6,11-trimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2,6-dimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2,3,6,7,10,11-hexamethyl-1,3,6,11-dodecatetraene, 19-methyl-1-(2-methyl-1-2,4,6,8,10,12,14,16,18-eicosanonaenylium, 17-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12,14,16-octadecaoctaenylium, 15-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12,14-hexadecaheptaenylium, 13-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12-tetradecahexaenylium, 11-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10-dodecapentaenylium, 9-methyl-1-(2-methyl-1-propenyl)-2,4,6,8-decatetraenylium, 7-methyl-1-(2-methyl-1-propenyl)-2,4,6-octatrienylium, 4,ethylidene-2,6-dimethyl-2,5-heptadiene, 3,7,11-trimethyl-(E or Z)-3,6,11-dodecatrien-1-yne, 3,7-dimethyl-(3E or 3Z)-3,6-octadien-1-yne, 3,7-dimethyl-(E or Z)-3,6-nonadien-1-yne, 3,6,7-trimethyl-(E or Z)-3,6-octadien-1-yne, 7-ethyl-3-methyl-(E or Z)-3,6-nonadien-1-yne, 3,7,11-trimethyl-(Z or E)-3,6,11-dodecatrien-1-yne, 2,3,6,7,10,11-hexamethyl-1,3,6,11-dodecatetraene, 2,6-dimethyl-2,5-heptadiene, 2-methyl-2,5-heptadiene, 3,6,10-trimethyl-2,5,7,10-dodecatetraene, 2,7,10-trimethyl-1,3,7,10-dodecatetraene, 3,6-dimethyl-1,3,6-octatriene, 12-(2,2-dimethyl-6-methylenecyclohexyl)-3,8,8-trimethyl-11-methylene-(E or Z)-(S)-1,3,6-dodecatriene, ocimene, 3,7,11-trimethyl-(3Z or 3E, 6Z or 6E)-1,3,6,10-dodecatetraene, 2-methyl-4-methylene-2,5-heptadiene, 3,8,8,14,18-pentamethyl-11-methylene-(E or Z)-1,3,6,13,17-nonadecapentaene, 2,7-dimethyl-2,5-octadiene, 3,8,8,14,18-pentamethyl-11-methylene-(E or Z, E or Z, E or Z)-1,3,6,13,17-nonadecapentaene, 6,10-dimethyl-2,4,6,9-undecatetraene, 2-methyl-(Z or E)-2,5-heptadiene, 2-methyl-(E or Z)-2,5-heptadiene, 3,7-dimethyl-1,3,6-octatriene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-(4Z or 4E)-cyclohexene, 2,6,10,14,19,22,27,31-octamethyl-2,6,10,14,16,18,22,26,30-dotriacontanonaene, 2,6-dimethyl-2,5-heptadiene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, 3,7-dimethyl-(3E or 3Z)-1,3,6-octatriene, 2,6,10,14,19,23,31-heptamethyl-2,5,10,14,16,18,22,26,29-dotriacontanonaene, 3,7,dimethyl-(3Z or 3E)-1,3,6-octatriene, 3-methyl-1-(2-methyl-1-propenyl-(E or Z)-2-pentenyl, 2,6-dimethyl-4-(2-methylpropenyl)-1,3,5-heptatriene, 2,6-dimethyl-4-methylene-2,5-heptadiene, 1-methyl-4-(1-methylethylidene)-cyclohexene, 3,7,11-trimethyl-(3E or 3Z, 6E or 6Z)-1,3,6,10-dodecatetraene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, isoprene, myrcene, dihydromyrene, linalool, terpinenes (α, β, and γ), limonene, terpinolene, menthadiene (p-3,8 or p-2,4), geraniol, nerol, geranylacetate, neryl acetate, nerolidol, farnesol, dehydronerolidol, α-bisabolol, valancene, nookatene, nootkatone, dimethyl-2,4,6-octratriene, β-phellandrences, piperitols (−, cis and +, trans), 1-methyl-1,4-cyclohexadiene, methyl cyclopentadiene dimer, ethylidene norbornene, dipentene, carvestrene, carvone (− or +), alloocimenes (4-trans-6-cis and 4-trans-6-trans), alloocimenols, ionomers, guaiazulene, lanosterol, squalene, lycopene, carotenes (β and γ), nopol glycidyl ether, and combinations thereof.  
     
     
         5 . The composition according to  claim 3 , wherein the compound having at least one oxirane linkage is a member selected from the group consisting of limonene diepoxide, gamma-terpinene diepoxide, methyl cyclopentadiene diepoxide dimer, ethylidene norbornene diepoxide, nopol epoxide glycidyl ether and combinations thereof.  
     
     
         6 . The composition according to  claim 1 , wherein the anhydride component of the curing agent component is selected from the group consisting of hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, 5-(2,5-dioxotetrahydrol)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, and combinations thereof.  
     
     
         7 . The composition according to  claim 1 , wherein the amine compounds of the curing agent component is selected from the group consisting of 1,5-diazabiyclo [4.3.0]non-5-ene; 1,8-diazabiylo[5.4.0]undec-7-ene; 1,5,7-triazabicyclo [4.4.0]dec-5-ene; quinuclidine; 1,4-diazabicyclo[2.2.2.]octane; and combinations thereof.  
     
     
         8 . (canceled)  
     
     
         9 . The composition according to  claim 1 , wherein the imidazole compounds of the curing agent component is selected from the group consisting of imidazole, isoimidazole, 2-methyl imidazole, 2-ethyl-4-methylimidazole, 2,4-dimethylimidazole, butylimidazole, 2-heptadecenyl-4-methylimidazole, 2-undecenylimidazole, 1-vinyl-2-methylimidazole, 2-n-heptadecylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1-benzyl-2-methylimidazole, 1-propyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-guanaminoethyl-2-methylimidazole, addition products of an imidazole and trimellitic acid, addition products of an imidazole and 2-n-heptadecyl-4-methylimidazole, phenylimidazole, benzylimidazole, 2-methyl-4,5-diphenylimidazole, 2,3,5-triphenylimidazole, 2-styrylimidazole, 1-(dodecyl benzyl)-2-methylimidazole, 2-(2-hydroxyl-4-t-butylphenyl)-4,5-diphenylimidazole, 2-(2-methoxyphenyl)-4,5-diphenylimidazole, 2-(3-hydroxyphenyl)-4,5-diphenylimidazole, 2-(p-dimethylaminophenyl)-4,5-diphenylimidazole, 2-(2-hydroxyphenyl)-4,5-diphenylimidazole, di(4,5-diphenyl-2-imidazole)-benzene-1,4,2-naphthyl-4,5-diphenylimidazole, 1-benzyl-2-methylimidazole, 2-p-methoxystyrylimidazole, and combinations thereof.  
     
     
         10 . The composition according to  claim 1 , wherein the curing agent component is used in an amount of from about 1 to about 100 weight percent, based on the weight of the curable resin component.  
     
     
         11 . The composition according to  claim 1 , further comprising an inorganic filler component.  
     
     
         12 . The composition according to  claim 11 , wherein the inorganic filler component is selected from the group consisting of materials constructed of or containing reinforcing silicas, aluminum oxide, silicon nitride, aluminum nitride, silica-coated aluminum nitride, boron nitride, and combinations thereof.  
     
     
         13 . The composition according to  claim 11 , wherein the inorganic filler component has a low ion concentration and a particle size in the range of about 2-10 microns.  
     
     
         14 - 18 . (canceled)  
     
     
         19 . The composition according to  claim 1 , further comprising a cyanate ester.  
     
     
         20 . The composition according to  claim 19 , wherein the cyanate ester is a member selected from the group consisting of dicyanatobenzenes, tricyanatobenzenes, dicyanatonaphthalenes, tricyanatonaphthalenes, dicyanato-biphenyl, bis(cyanatophenyl)methanes and alkyl derivatives thereof, bis(dihalocyanatophenyl)propanes, bis(cyanatophenyl)ethers, bis(cyanatophenyl)sulfides, bis(cyanatophenyl)propanes, tris(cyanatophenyl)phosphites, tris(cyanatophenyl)phosphates, bis(halocyanatophenyl)methanes, cyanated novolac, bis[cyanatophenyl(methylethylidene)]benzene, cyanated bisphenol-terminated thermoplastic oligomers, and combinations thereof.  
     
     
         21 . The composition according to  claim 1 , sealing underfilling between a semiconductor device including a semiconductor chip mounted on a carrier substrate and a circuit board to which the semiconductor device is electrically connected.  
     
     
         22 . The composition according to  claim 1 , sealing underfilling between a semiconductor device including a semiconductor chip mounted on a carrier substrate and a circuit board to which the semiconductor device is electrically connected, wherein the curable resin component is present in an amount within the range of about 10 to 70 weight percent, based on the total weight of the composition; the curing agent component is present in an amount within the range of 1 to about 100 weight percent, based on the weight of the curable resin component; and further comprising an inorganic filler component in an amount up to about 70 weight percent, based on the total weight of the composition; and a flowability agent in an amount up to about 2 weight percent, based on the weight of the composition.  
     
     
         23 . The composition according to  claim 1 , wherein the curable resin component includes a compound having at least one thiirane linkage substituted on at least three of the substitutable positions on the thiirane carbons with an alkyl, alkenyl or aryl substituent having a carbon content of 1 to about twelve carbon atoms, with or without substitution or interruption by one or more heteroatoms or halogens.  
     
     
         24 . The composition according to  claim 23 , wherein the compound having at least one thiirane linkage is a member selected from the group consisting of thiiranes prepared from 2,10-dimethyl-6-methylene-4,8-bis(2-methyl-1-propenyl 2,4,7,9-undecatetraene, 4-[(4E or 4Z)-1,5-dimethyl-4-heptenylidene or octenylidene]-1-methyl-cyclohexene, 1,1′-[(1E or 1Z, 3E or 3Z)-5-(1,1-dimethyl-2-propenyl)-3-(3-methyl-2-butenyl)-1,3-pentadiene-1,5-diyl]bis-benzene, 4,6-dimethyl-[S or R-(E or Z, Z or E)]-2,5-octadiene, 2,6,10,14-tetramethyl-7-(3-methyl-4-pentenyl)-2,5,9,13-pentadecatetraene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z, 10Z or 10E)-1,3,6,10-tridecatetraene, 3,4,8-trimethyl-1,4,7-nonatriene, 13-ethyl-9-methyl-1,9,12-pentadecatetraene, 1-methyl-4-(2-methyl-6-heptenylidene)-cyclohexene, 2,6,11-trimethyl-(E or Z)-2,5,10-dodecatriene, 2,6-dimethyl-(E or Z, E or Z)-2,6,9-tetradecatriene, 7-(3-methyl-2-butenyl-(E or Z)-6-dodecene, 6-(3-methyl-2-butenyl)-(E or Z)-6-dodecene, 2,4,6,6,8-pentamethyl-2,4,7-nonatriene, 3,7-dimethyl-11-(methyl)-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 5-[3-methyl-1-(2-methyl-1-propenyl)-2-butenylidene]-1,3-cyclopentadiene, 4-[(4E or 4Z)-1,5-dimethyl-4-heptenylidene]-1-methyl-(4Z or 4E)-cyclohexene, 3,7,11-trimethyl-1,3,6,10-docosatetraene, 3,7,11,15-tetramethyl-1,3,6,10-hexadecatetraene, 9-ethyl-2,6-dimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2-methyl-5-propyl-(E or Z)-2,5-nonadiene, 3,7,11-trimethyl-(Z or E, E or Z, E or Z)-1,3,6,10-dodecatetraene, 4,8,12-trimethyl-(Z or E, E or Z, E)-2,4,7,11-tridecatetraene, 1-methyl-4-(2-methyl-6-heptenylidene)-(E or Z)-cyclohexene, 3-ethyl-7,11-dimethyl-(E or Z, E or Z)-1, 3, 6, 10-dodecatetraene, 2,6,6,9-tetramethyl-7-(2-methyl-1-propenyl)-2,4,8-decatriene, 2,7-dimethyl-4,5-bis(2-methyl-1-propenyl)-2,6-octadiene, 3,7-dimethyl-1,3,6-octatriene, 2-methyl-5-(1-methylethylidene)-cyclohexene, 2,6-dimethyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 2,6-dimethyl-2,5-decadiene or octadiene, 7-ethyl-3,11-dimethyl-1,3,6,10-dodecatetraene, 2-methyl-(E or Z)-2,5-octadiene, 7-ethyl-3,11-dimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 2,7,11-trimethyl-(E or Z)-2,5,10-dodecatriene, 6,10-dimethyl-(Z or E, Z or E)-2,6,9-undecatrien-4-yne, 2,6-dimethyl-(Z or E)-2,5-dodecadiene, 2,7-dimethyl-4,5-bis(2-methyl-1-propenyl)-2,4,6-octatriene, 2,3,6,7-tetramethyl-1,3,6-octatriene, 2-methyl-5-propyl-(Z or E)-2,5-dodecadiene, 2-methyl-5-(1-methylethyl)-(E or Z)-2,5-dodecadiene, 2-methyl-(Z or E)-2,5-dodecadiene, 2,4,4-trimethyl-(E or Z)-2,5-heptadiene, 2,6-dimethyl-2,5-octadiene, 3,4,7,11-tetramethyl-(E or Z, Z or E)-1,3,6,10-dodecatraene, 3,7,11-trimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 4,8-dimethyl-1,4,7-nonatriene, 3,7,11,15-tetramethyl-1,3,6,10,14-hexadecapentaene, 2-methyl-(Z or E)-2,5-pentadecadiene, 2-methyl-5-(1-methylethylidene)-2-decene, 2,6-dimethyl-2,5,7-decatriene, 4,8-dimethyl-2,4,7-nonatriene, 15,19,23-trimethyl-15,18,22-heptatriacontatriene, 8-(2-methyl-1-propenyl)-6-tetradecene, 3,7,11-trimethyl-(E or Z)-1,3,6,10-dodecatetraene, 3,4-didehydro-2-(3-methyl-2-butenyl)-carotene, 7-ethyl-3,11-dimethyl-1,3,6,10-dodecatetraene, 1,3-dimethyl-4-propylidene-cyclopentene, 2,7,11-trimethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 6,10-dimethyl-1,4,6,9-undecatetraene, 2-(1-methylethyl)-5-(1-methylethylidene)-1,3-cyclohexadiene, 2-ethyl-5-ethylidene-cyclohexadiene, 2-methyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 3,7,10-trimethyl-(Z or E, E or Z)-1,3,6-undecatriene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, 1-methyl-4-(1-methylethylidene)-cyclohexene, 2,5-dimethyl-(Z or E)-2,5-heptadiene, 2-methyl-5-(1-methylethylidene)-1,3-cyclohexadiene, 2,6,10-trimethyl-(E or Z, Z or E)-2,6,9-tetradecatriene, 6-methyl-(Z or E, E or Z)-2,5-dodecadiene, 2,3,6-trimethyl-(E or Z, E or Z)-1,3,6-octatriene, tetrahydro-3,7,11-trimethyl-1,3,6,10-dodecatetraene, 3,4,7,11-tetramethyl-1,3,6,10-dodecatetraene, 3,4,7,11-tetramethyl-(Z or E, Z or E)-1,3,6,10-dodecatetraene, 2,6-dimethyl-4-methylene-2,5-heptadiene, 5-ethyl-2-methyl-2,5-heptadiene, 2,5-dimethyl-2,5-heptadiene or octadiene, 3,7,11-trimethyl-dodecatriene, 2,4,6,6,8-pentamethyl-(E or Z)-2,4,7-nonatriene, 3,7-diethyl-11-methyl-1,3,6,10-tridecatetraene, 7-ethyl-3,11-dimethyl-1,3,6,10-tridecatetraene, 2,6-dimethyl-(E or Z)-2,5-dodecadiene, 2,6,10-trimethyl-(E or Z, E or Z)-2,6,9-tetradecatriene, 3,7,11,15-tetramethyl-(Z or E, E or Z, E or Z)-1,3,6,10,14-hexadecapentaene, 3,7,11,15-tetramethyl-(3E or 3Z, 6E or 6Z, 10E or 10Z)-1,3,6,10,14-hexadecapentaene, 1-ethenyl-4-(1-methylethylidene)-cyclohexene, 1-methyl-6-methylene-4-(1-methylethylidene)-cyclohexene, 3,7,11-trimethyl-1,3,6-dodecatriene, 4-(1,5-dimethylhexylidene)-1-methyl-cyclohexene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z)-1,3,6,10-dodecatetraene, 1,3,3′,4,4′,16-hexadehydro-1,2-dihydro-2,2′-bis-3-carotene, 7-methyl-(Z or E, Z or E)-3,6-dodecadiene, 6-ethylidene-2,3,10-trimethyl-(E or Z, E or Z)-1,3,9-undecatriene, 2,3,6,7,10,11-hexamethyl-(E or Z, E or Z)-1,3,6,10-dodecatetraene, 2,3,6,7-tetramethyl-(E or Z)-1,3,6-octatriene, 2,7,11-trimethyl-1,3,6,11-dodecatetraene, 3,7,11,15,19,23,27,31,35-nonamethyl-1,3,6,10,14,18,22,26,30,34-hexatriacontadecaene, 2,6-dimethyl-9-propyl-2,6,9-tridecatriene, 3,6-dimethyl-(E or Z, E or Z)-1,3,6-octatriene, 3,7-diethyl-11-methyl-(3Z or 3E, 6E or 6Z) 1,3,6,10-tridecatetraene, 7-ethyl-3,11-dimethyl-(3Z or 3E, 6E or 6Z)-1,3,6,10-tridecatetraene, 1-methyl-4-(5-methyl-4-hexenylidene)-(4E or 4Z)-cyclohexene, 2,6,10-trimethyl-(Z or E)-2,5,9-undecatriene, 2,6,7,7-tetramethyl-(Z or E)-2,5-octadiene, 2,6,10,11,11-pentamethyl-2,6,9-dodecatriene, 2,6,10-trimethyl-2,6,9-tetradecatriene, 2,6-dimethyl-(Z or E)-2,5-decadiene, 6,10-dimethyl-1,6,9-undecatrien-4-yne, 2,3,6-trimethyl-2,5-heptadiene, 2,4-dimethyl-(E or Z)-2,5-heptadiene, 2,7,11-trimethyl-(E or Z, E or Z)-1,3,6,11-dodecatetraene, 6-ethyl-3-methyl-2,5-decadiene, 2,6,10-trimethyl-(Z or E)-2,5-undecadiene, 3,7-dimethyl-3,6-octadien-1-yne, 2,7,10-trimethyl-1,6,9-undecatriene, 4,5-dimethyl-(E or Z, E or Z, E or Z)-3,5,8-undecatriene, 4,5-dimethyl-2,5,8-undecatriene, 1′-[4-methyl-2-(2-methyl-1-propenyl)-1,3-pentadienylidene]bis-benzene, 1,4-(1,5-dimethyl-4-hexenylidene)-1-methyl-(4E or 4Z)-cyclohexene, 2,6,11,15-tetramethyl-(Z or E)-2,6,9,14-hexadecatetraene, [3-methyl-1-(2-methyl-1-propenyl)-2-butenyl]-benzene, 2,6,11-trimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2,6-dimethyl-(E or Z, E or Z)-2,6,9-dodecatriene, 2,3,6,7,10,11-hexamethyl-1,3,6,11-dodecatetraene, 19-methyl-1-(2-methyl-1-2,4,6,8,10,12,14,16,18-eicosanonaenylium, 17-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12,14,16-octadecaoctaenylium, 15-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12,14-hexadecaheptaenylium, 13-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10,12-tetradecahexaenylium, 11-methyl-1-(2-methyl-1-propenyl)-2,4,6,8,10-dodecapentaenylium, 9-methyl-1-(2-methyl-1-propenyl)-2,4,6,8-decatetraenylium, 7-methyl-1-(2-methyl-1-propenyl)-2,4,6-octatrienylium, 4,ethylidene-2,6-dimethyl-2,5-heptadiene, 3,7,11-trimethyl-(E or Z)-3,6,11-dodecatrien-1-yne, 3,7-dimethyl-(3E or 3Z)-3,6-octadien-1-yne, 3,7-dimethyl-(E or Z)-3,6-nonadien-1-yne, 3,6,7-trimethyl-(E or Z)-3,6-octadien-1-yne, 7-ethyl-3-methyl-(E or Z)-3,6-nonadien-1-yne, 3,7,11-trimethyl-(Z or E)-3,6,11-dodecatrien-1-yne, 2,3,6,7,10,11-hexamethyl-1,3,6,11-dodecatetraene, 2,6-dimethyl-2,5-heptadiene, 2-methyl-2,5-heptadiene, 3,6,10-trimethyl-2,5,7,10-dodecatetraene, 2,7,10-trimethyl-1,3,7,10-dodecatetraene, 3,6-dimethyl-1,3,6-octatriene, 12-(2,2-dimethyl-6-methylenecyclohexyl)-3,8,8-trimethyl-11-methylene-(E or Z)-(S)-1,3,6-dodecatriene, ocimene, 3,7,11-trimethyl-(3Z or 3E, 6Z or 6E)-1,3,6,10-dodecatetraene, 2-methyl-4-methylene-2,5-heptadiene, 3,8,8,14,18-pentamethyl-11-methylene-(E or Z)-1,3,6,13,17-nonadecapentaene, 2,7-dimethyl-2,5-octadiene, 3,8,8,14,18-pentamethyl-11-methylene-(E or Z, E or Z, E or Z)-1,3,6,13,17-nonadecapentaene, 6,10-dimethyl-2,4,6,9-undecatetraene, 2-methyl-(Z or E)-2,5-heptadiene, 2-methyl-(E or Z)-2,5-heptadiene, 3,7-dimethyl-1,3,6-octatriene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-(4Z or 4E)-cyclohexene, 2,6,10,14,19,22,27,31-octamethyl-2,6,10,14,16,18,22,26,30-dotriacontanonaene, 2,6-dimethyl-2,5-heptadiene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, 3,7-dimethyl-(3E or 3Z)-1,3,6-octatriene, 2,6,10,14,19,23,31-heptamethyl-2,5,10,14,16,18,22,26,29-dotriacontanonaene, 3,7,dimethyl-(3Z or 3E)-1,3,6-octatriene, 3-methyl-1-(2-methyl-1-propenyl-(E or Z)-2-pentenyl, 2,6-dimethyl-4-(2-methylpropenyl)-1,3,5-heptatriene, 2,6-dimethyl-4-methylene-2,5-heptadiene, 1-methyl-4-(1-methylethylidene)-cyclohexene, 3,7,11-trimethyl-(3E or 3Z, 6E or 6Z)-1,3,6,10-dodecatetraene, 4-(1,5-dimethyl-4-hexenylidene)-1-methyl-cyclohexene, isoprene, myrcene, dihydromyrene, linalool, terpinenes (α, β, and γ), limonene, terpinolene, menthadiene (p-3,8 or p-2,4), geraniol, nerol, geranylacetate, neryl acetate, nerolidol, farnesol, dehydronerolidol, α-bisabolol, valancene, nookatene, nootkatone, dimethyl-2,4,6-octratriene, β-phellandrences, piperitols (−, cis and +, trans), 1-methyl-1,4-cyclohexadiene, methyl cyclopentadiene dimer, ethylidene norbornene, dipentene, carvestrene, carvone (− or +) alloocimenes (4-trans-6-cis and 4-trans-6-trans), alloocimenols, ionomers, guaiazulene, lanosterol, squalene, lycopene, carotenes (β and γ), nopol glycidyl ether, and combinations thereof.  
     
     
         25 . The compositions according to  claim 1 , wherein the thiirane compound is a member selected from the group consisting of thiiranes prepared from limonene, terpinene, nopol, ethylidene norbornene, methyl cyclopentadiene dimer, and combinations thereof.  
     
     
         26 - 30 . (canceled)  
     
     
         31 . Reaction products formed from the compositions according to  claim 1 .  
     
     
         32 - 39 . (canceled)