Near infrared absorbing phthalocyanines and their use

Abstract

The instant invention relates to novel phthalocyanines and their use as IR-absorbers, in particular in transparent thermoplastic or crosslinkable polymers. A further aspect of the invention is a composition of these phthalocyanines and thermoplastic or crosslinkable polymers and an architectural or automotive glazing containing these phthalocyanines.

1 . A compound of formula (Ia) 
     
       
         
         
             
             
         
       
       wherein 
       R is hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkyl interrupted by one or more O atoms, benzyl or cyclohexyl; 
       R′ is hydrogen or C 1 -C 18 alkyl; 
       or R and R′ together with the nitrogen atom to which they are bonded form a morpholine group; and 
       M is Mn, Zn, V(O), Ti(O), Si, Al, Sn, Cu or Co; 
       with the provisos that 
       if R is methyl and R′ is hydrogen, M is not Zn, 
       if R and R′ are butyl or octyl M is not Sn and 
       if R and R′ are methyl M is not Zn, Ti(O), V(O), Cu or Co. 
     
   
   
       2 . A compound according to  claim 1  wherein M is Mn, Cu, V(O), Co or Al. 
   
   
       3 . A compound according to  claim 1  wherein
 R is C 1 -C 18 alkyl;   R′ is H and   M is Mn, Cu, V(O), Co or Al.   
   
   
       4 . A compound according to  claim 1  wherein
 R is CH 3      R′ is hydrogen and   M is Mn, V(O), Cu or Co.   
   
   
       5 . A transparent or translucent composition comprising
 a) a compound of formula (I)   
     
       
         
         
             
             
         
       
       wherein 
       R is hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkyl interrupted by one or more O atoms, benzyl or cyclohexyl; 
       R′ is hydrogen or C 1 -C 18 alkyl; 
       R and R′ together with the nitrogen atom to which they are bonded form a morpholine group; and 
       M is Mn, Zn, V(O), Ti(O), Si, Al, Sn, Cu or Co; 
       which is dispersed in 
       b) a thermoplastic or crosslinkable polymer. 
     
   
   
       6 . A composition according to  claim 5  wherein the thermoplastic or crosslinkable polymer comprises polycarbonate, a coating or coextruded layer on polycarbonate polyesters acrylics halogenated polymers, polyolefins, aromatic homopolymers, copolymers derived from vinyl aromatic monomers, polyvinylacetales or blends, alloys or co-polymers thereof. 
   
   
       7 . A composition according to  claim 5 , wherein the thermoplastic or crosslinkable polymer comprises polycarbonate, polymethylmethacrylate, polyethyleneterephthalate, polyvinylchloride, transparent ABS, polyvinylidene fluoride, styrene-acrylnitril copolymer, polypropylene, polyethylene or mixtures thereof. 
   
   
       8 . A composition according to  claim 5  wherein the compound of formula (I) is present in an amount from 0.01 to 10% by weight, based on the weight of the thermoplastic or crosslinkable polymer. 
   
   
       9 . A composition according to  claim 5 , containing as further component a conventional additive selected from antioxidants, flame retardants, clarifiers, UV absorbers and/sterically hindered amines. 
   
   
       10 . A composition according to  claim 5  containing as further component solid nano-scaled particles of a thickness of less than 200 nm, which consist of an oxide of zinc and/or a nitride of a transition metal of group III, IV, V or VI of the periodic system, each of which is doped with one or more of the elements belonging to main groups III or IV of the periodic system, or consist of undoped vanadium nitride or scandium nitride. 
   
   
       11 . A composition according to  claim 10  comprising a nitride which is selected from nitrides of scandium, yttrium, lanthanum, lanthanides, titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum and wolfram; and where the doping elements are selected from boron, aluminum gallium, indium thallium, carbon, silicon, germanium, tin and lead. 
   
   
       12 . A composition according to  claim 5  containing as further component tin oxide doped with antimony (ATO), tin oxide doped with indium (ITO), zinc oxide doped with aluminum (AZO), zinc oxide doped with indium (IZO), zinc oxide doped with gallium (GaZO), LaB 6 , doped tungsten oxides (YWO x ), silver or gold nanoparticles, nanoprisms or nanorods or carbon nanotubes. 
   
   
       13 . Architectural or automotive glazing in form of a solid plate or sheet, a monolithic sheet, a twin-wall sheet, a multi-wall sheet, a flat sheet or a corrugated sheet; or an agricultural film in form of a mono- or biaxially oriented film, a laminated film or a capstock film, comprising a composition according to  claim 5 . 
   
   
       14 . Process for the preparation of a transparent or translucent heat shielding material, which process comprises the addition of a compound of formula (I) 
     
       
         
         
             
             
         
       
       wherein 
       R is hydrogen, C 1 -C 18 alkyl, C 3 -C 18 alkyl interrupted by one or more O atoms, benzyl or cyclohexyl; 
       R′ is hydrogen or C 1 -C 18 alkyl; 
       or R and R′ together with the nitrogen atom to which they are bonded form a morpholine group; and 
       R′ is hydrogen or C 1 -C 18 alkyl and 
       M is Mn, Zn, V(O), Ti(O), Si, Al, Sn, Cu or Co; 
       to a thermoplastic or crosslinkable polymer. 
     
   
   
       15 - 17 . (canceled) 
   
   
       18 . A composition according to  claim 10  wherein the particles consist of aluminum doped zinc oxide, indium doped zinc oxide, gallium doped zinc oxide, aluminum doped titanium nitride, indium doped titanium nitride, gallium doped titanium nitride, aluminum doped vanadium nitride, indium doped vanadium nitride, gallium doped vanadium nitride, vanadium nitride, aluminum doped scandium nitride, indium doped scandium nitride, gallium doped scandium nitride or scandium nitride.