Radiation curable compositions

Abstract

The invention relates to a radiation curable composition comprising radiation curable components wherein at least one component of the radiation curable composition contains a functional group which, when attached to an acrylate group has a calculated Boltzmann average dipole moment of higher than 3.5 Debye. The invention further relates to radiation curable optical fiber coating compositions having a high dielectric constant.

1 - 34 . (canceled)  
     
     
         35 . A process for preparing a radiation curable composition, comprising: reacting together 
 (i) an hydroxy-, thiol- or NH-functional (meth)acrylate,    (ii) a di-or more functional isocyanate, and    (iii) an hydroxy-, thiol- or NH-functional compound having a calculated Boltzmann average dipole moment of greater than 2.5 Debye    wherein one or more compounds formed are chosen from the group consisting of compounds (C1) according to the formula (1):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 ,R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or compounds (C2) according to formula (2):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=2-4,    or compounds (C3) according to the formula (3):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or a compound (C4) according to the formula (4):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3 , are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; n is 1-4;    or a compound (C5) according to the formula (5):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-5; p=0, 1; but excluding a compound wherein R 1 ═CH 2 CHCO 2 CH 2 CH 2  or R1=CH 2 CCH 3 CO 2 CH 2 CH 2  with n=2, 3 and X=Y=oxygen,    or a compound (C6) according to the formula (6):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4,    or a compound (C7) according to the formula (7):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; W, X, Y and Z are independently an oxygen or sulfur atom or an NR 7 -group with the proviso that W and X are not both an NR 7 -group at the same time; n is 1-4;    or a compound (C8) according to the formula (8):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 1-4;    or a compound (C9) according to the formula (9):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-4.    
     
     
         36 . The process of  claim 35  wherein one or more of the compounds formed as defined in claim  1  is prepared by reacting together 
 (i) an hydroxy functional (meth)acrylate,    (ii) a di-functional isocyanate, and    (iii) a hydroxy functional compound having a calculated Boltzmann average dipole moment of greater than 2.5 Debye.    
     
     
         37 . The process of  claim 35  wherein one or more of the compounds formed as defined by  claim 35  is prepared by reacting together 
 (i) one equivalent of a hydroxy functional (meth)acrylate,    (ii) two equivalents of a di-functional isocyanate,    (iii) one equivalent of a diamine, dihydroxy or dithiol functional compound with a molecular weight Mn of 1000 or less, and    (iv) one equivalent of a hydroxy functional compound having a calculated Boltzmann average dipole moment of greater than 2.5 Debye.    
     
     
         38 . The process of  claim 35  wherein one or more of the compounds formed as defined by  claim 35  is prepared by reacting together 
 (i) one equivalent of a hydroxy functional (meth)acrylate, (ii) two equivalents of a di-functional isocyanate,    (ii) one equivalent of a diamine, dihydroxy or dithiol functional compound with a molecular weight Mn of greater than 1000, and    (iii) one equivalent of a hydroxy functional compound having a calculated Boltzmann average dipole moment of greater than 2.5 Debye.    
     
     
         39 . The process of  claim 35  wherein one or more of the compounds formed as defined by  claim 35  is prepared by reacting together 
 (i) an hydroxy functional (meth)acrylate,    (ii) a tri-or more functional isocyanate,    (iii) a hydroxy functional compound having a calculated Boltzmann average dipole moment of greater than 2.5 Debye together, and    (iv) a hydroxy or amine functional oligomer with an average hydroxy or amine functionality greater than 1.5.    
     
     
         40 . The process according to  claim 35 , wherein the compound includes a functional group which when attached to an acrylate group has a calculated Boltzmann average dipole moment of greater than 3.5 Debye.  
     
     
         41 . The process according to  claim 40 , wherein the functional group when attached to an acrylate group has a calculated Boltzmann average dipole moment of greater than 4.5 Debye.  
     
     
         42 . The process of  claim 35  further comprising coating a glass fiber with one or more compounds as defined in  claim 35  and curing the composition.  
     
     
         43 . An optical fiber coating composition comprising: 
 one or more compounds chosen from the group consisting of compounds (C1) according to the formula (1):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 ,R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or compounds (C2) according to formula (2):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=2-4,    or compounds (C3) according to the formula (3):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or a compound (C4) according to the formula (4):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3 , are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; n is 1-4;    or a compound (C5) according to the formula (5):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-5; p=0, 1; but excluding a compound wherein R 1 ═CH 2 CHCO 2 CH 2 CH 2  or R 1 ═CH 2 CCH 3 CO 2 CH 2 CH 2  with n=2, 3 and X=Y=oxygen,    or a compound (C6) according to the formula (6):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4,    or a compound (C7) according to the formula (7):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; W, X, Y and Z are independently an oxygen or sulfur atom or an NR 7 -group with the proviso that W and X are not both an NR 7 -group at the same time; n is 1-4;    or a compound (C8) according to the formula (8):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 1-4;    or a compound (C9) according to the formula (9):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-4.    
     
     
         44 . The optical fiber coating composition of  claim 43 , further comprising N-vinylpyrrolidone.  
     
     
         45 . The optical fiber coating composition of  claim 43 , further comprising N-vinylcaprolactam.  
     
     
         46 . A coated optical fiber comprising a glass optical fiber, a primary coating applied thereon, a secondary coating applied on the primary coating and optionally an ink composition applied on the secondary coating, wherein at least one of the primary coating, secondary coating or ink composition comprises one or more of the following compounds: 
 compounds (C1) according to the formula (1):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 ,R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or compounds (C2) according to formula (2):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=2-4,    or compounds (C3) according to the formula (3):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;    or a compound (C4) according to the formula (4):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3 , are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; n is 1-4;    or a compound (C5) according to the formula (5):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-5; p=0, 1; but excluding a compound wherein R 1 ═CH 2 CHCO 2 CH 2 CH 2  or R1=CH 2 CCH 3 CO 2 CH 2 CH 2  with n=2, 3 and X=Y=oxygen,    or a compound (C6) according to the formula (6):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4,    or a compound (C7) according to the formula (7):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; W, X, Y and Z are independently an oxygen or sulfur atom or an NR 7 -group with the proviso that W and X are not both an NR 7 -group at the same time; n is 1-4;    or a compound (C8) according to the formula (8):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 1-4;    or a compound (C9) according to the formula (9):                          wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-4.    
     
     
         47 . An optical fiber according to  claim 46 , wherein at least one of the compounds has a calculated Boltzman average dipole moment of higher than 2.5 Debye.  
     
     
         48 . Optical fiber ribbon comprising a plurality of coated, and optionally colored optical fibers arranged in a plane and embedded in a matrix composition, wherein the coated optical fiber is a fiber according to  claim 46 .  
     
     
         49 . The process according to  claim 35  further comprising coating a surface of one or more polycarbonate substrates with one or more compounds according to  claim 35 .  
     
     
         50 . The process according to  claim 49  wherein the one or more compounds on the one or more coated polycarbonate substrates are cured with ultraviolet radiation at a dose of 0.2-1.0 J/cm 2 .  
     
     
         51 . The process according to  claim 49  wherein two coated polycarbonate substrates are superimposed on each other to form a single DVD.  
     
     
         52 . An adhesive compound comprising: 
 one or more of the following compounds: 
 compounds (C1) according to the formula (1):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 ,R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;  
 or compounds (C2) according to formula (2):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=2-4,  
 or compounds (C3) according to the formula (3):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4;  
 or a compound (C4) according to the formula (4):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3 , are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X and W are independently an oxygen or sulfur atom; n is 1-4;  
 or a compound (C5) according to the formula (5):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 , and R 3  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-5; p=0, 1; but excluding a compound wherein R 1 ═CH 2 CHCO 2 CH 2 CH 2  or R1=CH 2 CCH 3 CO 2 CH 2 CH 2  with n=2, 3 and X=Y=oxygen,  
 or a compound (C6) according to the formula (6):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 0-4; m is 0-4 and n+m=1-4,  
 or a compound (C7) according to the formula (7):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 ,R 4 ,R 5 , R 6  and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; W, X, Y and Z are independently an oxygen or sulfur atom or an NR 7 -group with the proviso that W and X are not both an NR 7 -group at the same time; n is 1-4;  
 or a compound (C8) according to the formula (8):  
                     
 wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y and Z are independently an oxygen or sulfur atom or an NR 7 -group; n is 1-4;  
 or a compound (C9) according to the formula (9):  
                     
   wherein R 1 =organic group with a molecular weight between 40 and 20000; R 2 ,R 3 , and R 7  are independently of each other H, an alkyl group having 1-20 C atoms, wherein the alkyl group can be linear, branched or cyclic and may contain heteroatoms like ═N, O, S and P or an aryl group having from 6-20 C-atoms; X is an oxygen or sulfur atom; Y is an oxygen or sulfur atom or an NR 7 -group; n is 1-4.    
     
     
         53 . A radiation curable DVD adhesive comprising the composition of  claim 52 .  
     
     
         54 . A DVD comprising two polycarbonate substrates adhered to each other using a composition of  claim 52.