Flame-retardant, high temperature resistant thermosets on the basis of naphthalene-based epoxy resins and cyanate esters

Abstract

The embodiments relate to a polymerisable thermoset composition having improved flame retardant properties, a polymerised thermoset having improved flame retardant properties, a process for manufacturing the polymerised thermoset, and use of the polymerisable thermoset composition to produce lightweight construction components, preferably carbon fibre composites (CFRP), and a lightweight construction component, preferably carbon fibre composite (CFRP), containing the polymerised thermoset.

What is claimed is: 
     
         1 . A polymerisable thermoset composition, comprising:
 a) a di- or polyfunctional organic cyanate ester resin;   b) a naphthalene based epoxy resin; and   c1) at least one phosphorus-containing phenol; and/or   c2) at least one phosphorus-containing epoxy and at least one diamine;   wherein the polymerisable thermoset composition comprises at least one high-performance thermoplast.   
     
     
         2 . The polymerisable thermoset composition according to  claim 1 , wherein the phosphorus-containing phenol is a (hydrocarbyl-)phosphonic acid ester and/or contains 9-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide as the structural unit. 
     
     
         3 . The polymerisable thermoset composition according to  claim 1 , wherein the phosphorus-containing epoxy is a (hydrocarbyl-)phosphonic acid ester and/or contains 9-dihydroz-9-oxa-10-phosphaphenanthrene-10-oxide as the structural unit. 
     
     
         4 . The polymerisable thermoset composition according to  claim 1 , wherein the phosphorus-containing phenol contains one of the following structural units: 
       
         
           
           
               
               
           
         
         wherein: 
         n is a number between 1 and 1000, 
         o is a number between 0 and 4, 
         p is a number between 0 and 4, 
         r is a number between 0 and 3, 
         R 1  is a C 1 -C 10  alkyl, 
         R 2  is a C 1 -C 10  alkyl, and 
         R 3  is a C 1 -C 10  alkyl; 
         or 
       
       
         
           
           
               
               
           
         
         wherein: 
         s is a number between 1 and 1000, 
         t is a number between 0 and 4, and 
         R 4  is a C 1 -C 10  alkyl. 
       
     
     
         5 . The polymerisable thermoset composition according to  claim 1 , wherein the phosphorus-containing epoxy contains the following structural unit (III): 
       
         
           
           
               
               
           
         
         wherein 
         a is a number between 0 and 4, 
         b is a number between 0 and 4, 
         c is a number between 0 and 3, 
         d is a number between 0 and 3, 
         e is a number between 1 and 1000, 
         f is a number between 1 and 1000, 
         R 10  is a C 1 -C 10  alkyl, 
         R 11  is a C 1 -C 10  alkyl, 
         R 12  is a C 1 -C 10  alkyl or hydrogen, 
         R 13  is a C 1 -C 10  alkyl or hydrogen, 
         R 14  is a C 1 -C 10  alkyl or hydrogen, 
         R 15  is a C 1 -C 10  alkyl or hydrogen, 
         R 16  is a C 1 -C 10  alkyl, 
         R 17  is a C 1 -C 10  alkyl, 
         R 18  is a C 1 -C 10  alkyl or hydrogen, and 
         R 19  is a C 1 -C 10  alkyl or hydrogen. 
       
     
     
         6 . The polymerisable thermoset composition according to  claim 1 , wherein the di- or polyfunctional organic cyanate ester resin is a cyanate having formula (IV): 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2  and R 3  are each independently hydrogen or C 1 -C 10  alkyl, and n represents an integer from 0 to 20. 
       
     
     
         7 . The polymerisable thermoset composition according to  claim 1 , wherein the naphthalene-based epoxy resin represents a polymeric naphthalene-based epoxy resin. 
     
     
         8 . The polymerisable thermoset composition according to  claim 1 , wherein the at least one high-performance thermoplast is selected from the group comprising polysulfones (PSU), polyetherimide (PEI), polysulfone (PSU), polycarbonate (PC), silicone rubber and mixtures thereof. 
     
     
         9 . The polymerisable thermoset composition according to  claim 1 , wherein the high-performance thermoplast is present in the form of core-shell particles. 
     
     
         10 . The polymerisable thermoset composition according to  claim 9 , wherein the shell of the core-shell particles contains an epoxy resin, a cyanate ester or mixtures thereof, and the core contains a silicone rubber. 
     
     
         11 . A polymerised thermoset constituting a reaction product of the polymerisable thermoset composition according to  claim 1 . 
     
     
         12 . A polymerised thermoset according to  claim 11 , wherein the thermoset has a glass transition temperature from 285° C. to 300° C. and/or curing temperature in a range from 100 to 180° C. 
     
     
         13 . A process for manufacturing a polymerised thermoset, comprising the steps of:
 i) providing a polymerisable thermoset composition according to  claim 1 ;   ii) polymerising the polymerisable thermoset composition at temperatures of from 100 to 180° C.   
     
     
         14 . Use of the polymerisable thermoset composition according to  claim 1  to manufacture lightweight construction components. 
     
     
         15 . A lightweight construction component containing the polymerised thermoset according to  claim 11 .