Thermally Resistant Anaerobically Curable Compositions

Abstract

The present invention relates to anaerobically curable compositions demonstrating resistance to elevated temperature conditions.

1 . An anaerobic curable composition, comprising:
 (a) a (meth)acrylate component;   (b) an anaerobic cure system; and   (c) a component comprising the structural unit, MO—X(Y)—OM′, wherein M and M′ are independently selected from the group consisting of hydrogen, sodium, potassium, and lithium, X is silicon or boron, and Y is ═O, when X is silicon and v is OH, when X is boron, provided that when Y is OH, when X is boron, the component is present in an amount within the range of about 25 weight percent to 75 weight percent.   
   
   
       2 . The composition according to  claim 1 , wherein X in the component is boron, and is present in an amount within the range of about 35 weight percent to 60 weight percent. 
   
   
       3 . The composition according to  claim 1 , wherein X in the component is boron, and is present in an amount within the range of about 40 weight percent to 50 weight percent. 
   
   
       4 . The composition according to  claim 1 , wherein the (meth)acrylate component is represented by H 2 C═CGCO 2 R 1 , wherein G is a member selected from the group consisting of H, halogen and alkyl having from 1 to about four carbon atoms, and R 1  is a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, and aryl groups having from 1 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulfonate and sulfone. 
   
   
       5 . The composition according to  claim 1 , wherein the (meth)acrylate component selected from the group consisting of silicone (meth)acrylates, polyethylene glycol di(meth)acrylates, bisphenol-A-(methacrylates, ethoxylated bisphenol-A-(meth)acrylates, bisphenol-F-(meth)acrylates, ethoxylated bisphenol-F-(meth)acrylates, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl(meth)acrylate, hexanediol di(meth)acrylate, and trimethylol propane tri(meth)acrylate. 
   
   
       6 . The composition according to  claim 1 , wherein the anaerobic cure system comprises one or more of the following:
 A. the combination of saccharin, toluidines, acetyl phenylhydrazine, maleic acid, and quinones;   B.   
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2  and R 3  are each independently selected from the group consisting of hydrogen or C 1-4 ; Z is a carbon-carbon single bond or carbon-carbon double bond; m is 0 or 1; and n is an integer between 1 and 5;
 C. 
 
     
       
         
         
             
             
         
       
       wherein Y is selected from the group consisting of an aromatic ring, optionally substituted at up to five positions by C 1-6  alkyl or alkoxy, or halo groups; A is C═O, S═O or O═S═O; X is NH, O or S and Z is an aromatic ring, optionally substituted at up to five positions by C 1-6  alkyl or alkoxy, or halo groups, or Y and Z taken together may join to the same aromatic ring or aromatic ring system, provided that when X is NH, o-benzoic sulfimide is excluded therefrom; 
       D. 
     
     
       
         
         
             
             
         
       
     
     wherein R is selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, carboxyl, or sulfonato, and R 1  is as defined above and alkenyl, hydroxyalkyl, hydroxyalkenyl, or aralkyl;
 E. trithiadiaza pentalenes embraced by the following structure: 
 
     
       
         
         
             
             
         
       
     
     wherein A and A′ are each independently selected from the group consisting of O and N; and
 R, R 1 , R 2  and R 3  are the same or different, are as defined above and cycloalkyl, cycloalkenyl, and aryl, having from 1 to about 30 carbon atoms, and may be substituted or interrupted with a heteroatom, and heterocyclic structures, or 
 R 1  and R 3  taken together may join to form a cyclic structure having from about 20 to about 28 ring atoms, and together represent dialkyl substituted polyether structures that may be substituted or interrupted with the trithiadiaza pentalene structure, which itself may or may not be substituted by A 1 , R 2  or R 3 , as defined above; and 
 F. the combination of a triazine and a thiol. 
 
   
   
       7 . The composition according to  claim 1 , further comprising a coreactant. 
   
   
       8 . The composition according to  claim 7 , wherein the coreactant is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     wherein in structure I, X is present at least once and is chosen from H or D n A, wherein n can range between 0 and 1, with at least one X being D n A, wherein D can be attached to the ring and can be chosen from O, S, or NH and A is attached to D (if present) or directly to the ring, wherein A is represented by structure III below: 
     
       
         
         
             
             
         
       
       wherein E is a member selected from the group consisting of H, linear, branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or aryl groups, having from 1 to 20 carbon atoms with or without substitution by halogen, silicon, hydroxy, nitrile, ester, amide or sulfate, wherein R is selected from the group consisting of H, linear, branched or cyclic alkyl, alkenyl, alkynyl, alkoxy or aryl groups, having from 1 to about 20 carbon atoms, with or without substitution by halogen, silicon, hydroxy, nitrile, ester, amide or sulfate; 
     
     wherein in structure II, X 1  is present at least once and is chosen from H or O═CD n A, with at least; one X 1  being O═CD n A, wherein D, and A are as defined above; and 
     wherein in structure III, D and A are as described above and are present at least once and can also be present together attached to rind atoms which are in alpha-beta relation to one another. 
   
   
       9 . The composition according to  claim 8 , wherein the coreactant is 
     
       
         
         
             
             
         
       
     
   
   
       10 . Reaction products of the composition according to  claim 1 . 
   
   
       11 . A process for preparing a reaction product from an anaerobic curable composition, comprising the steps of:
 apply an anaerobic curable composition according to  claim 1 , to a desired substrate surface and   exposing the composition to an anaerobic environment for a time sufficient to cure the composition.   
   
   
       12 . A composition comprising a bond formed between two mated substrates with the composition of  claim 1 .