Compounds suitable for use in inks and inks having such compounds

Abstract

Disclosed herein are amide compounds suitable for use in ink compositions, and methods of making the amide compounds disclosed herein.

1 . A compound having a formula of R 1 —CONH—R 2  or R 2 —CONH—R 1 , wherein R 2  is an alkyl group having from 1 to about 18 carbon atoms and R 1  is an alkyl group having from about 3 carbon atoms to about 200 carbon atoms, and wherein R 2  and R 1  have the same number of carbon atoms or R 2  has less carbon atoms than R 1 . 
   
   
       2 . The compound according to  claim 1 , wherein R 1  is a straight chain alkyl having no substituents or heteroatoms. 
   
   
       3 . The compound according to  claim 1 , wherein R 1  is a straight chain alkyl or a branched alkyl having at least one hydroxyl group substituent. 
   
   
       4 . The compound according to  claim 1 , wherein R 2  is an alkyl group having no substituents or heteroatoms. 
   
   
       5 . A compound having a formula of R 1 —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 6 —NHCO—R 3  or R 1 —NHCO—R 6 —NHCO—R 3 , wherein R 6  is a cyclic group having from about 5 to about 8 carbon atoms and R 1  and R 3  are the same or different and comprise an alkyl group having from about 3 carbon atoms to about 200 carbon atoms. 
   
   
       6 . The compound according to  claim 5 , wherein the compound has a formula of 
     
       
         
         
             
             
         
       
     
   
   
       7 . The compound according to  claim 5 , wherein one or both of R 1  and R 3  include at least one hydroxyl substituent. 
   
   
       8 . The compound according to  claim 5 , wherein one or both of R 1  and R 3  is a straight chain alkyl having no substituents or heteroatoms. 
   
   
       9 . The compound according to  claim 5 , wherein R 1  and R 3  are different such that when one of R 1  and R 3  is a straight chain alkyl the other is a hydroxyl group containing alkyl, when one of R 1  and R 3  is a branched alkyl the other is a hydroxyl group containing alkyl or when one of R 1  and R 3  is a straight chain alkyl the other is a branched alkyl. 
   
   
       10 . A compound having a formula of R 1 —CONH—R 6 —CONH—C 36 H 64+n —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —NHCO—C 36 H 64+n —NHCO—R 6 —NHCO—R 3 , R—CONH—R 6 —NHCO—C 36 H 64+n —CONH—R 6 —NHCO—R 3 , R 1 —NHCO—R 6 —CONH—C 36 H 64+n —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 4 —CONH—C 36 H 64+n —CONH—R 5 —CONH—R 3 , R 1 —CONH—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —NHCO—R 3  or R 1 —NHCO—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —CONH—R 3 , R 1 —NHCO—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —CONH—R 3 , or R 1 —CONH—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —NHCO—R 3 , wherein R 6  is the same or different a cyclic group having from about 5 to about 8 carbon atoms, R 4  and R 3  are the same or different and comprise an alkylene having from 1 to about 200 carbon atoms, and R 1  and R 3  are the same or different and comprise a straight chain or branched alkyl group having from about 3 carbon atoms to about 200 carbon atoms. 
   
   
       11 . The compound according to  claim 10 , wherein the compound has a formula of 
     
       
         
         
             
             
         
       
     
   
   
       12 . The compound according to  claim 11 , wherein R 1  and R 3  are different such that when one of R 1  and R 3  is a straight chain alkyl the other is a hydroxyl group containing alkyl, when one of R 1  and R 3  is a branched alkyl the other is a hydroxyl group containing alkyl or when one of R 1  and R 3  is a straight chain alkyl the other is a branched alkyl. 
   
   
       13 . The compound according to  claim 10 , wherein the compound has a formula of 
     
       
         
         
             
             
         
       
     
   
   
       14 . The compound according to  claim 13 , wherein R 1  and R 3  are different such that when one of R 1  and R 3  is a straight chain alkyl the other is a hydroxyl group containing alkyl, when one of R 1  and R 3  is a branched alkyl the other is a hydroxyl group containing alkyl or when one of R 1  and R 3  is a straight chain alkyl the other is a branched alkyl. 
   
   
       15 . A method of making a compound suitable for use in an ink composition, the method comprising reacting an amine and at least one carboxylic acid to form a compound selected from the group consisting of (1) a compound having a formula of R 1 —CONH—R 2  or R 2 —CONH—R 1 , wherein R 2  is an alkyl group having from 1 to about 18 carbon atoms and R 1  is an alkyl group having from about 3 carbon atoms to about 200 carbon atoms, and wherein R 2  and R 1  have the same number of carbon atoms or R 2  has less carbon atoms than R 1 , (2) a compound having a formula of R 1 —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 6 —NHCO—R 3  or R—NHCO—R 6 —NHCO—R 3 , wherein R 6  is a cyclic group having from about 5 to about 8 carbon atoms and R 1  and R 3  are the same or different and comprise a straight chain or branched alkyl group having from about 3 carbon atoms to about 200 carbon atoms and (3) a compound having a formula of R 1 —CONH—R 6 —CONH—C 36 H 64+n —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —NHCO—C 36 H 64+n —NHCO—R 6 —NHCO—R 3 , R 1 —CONH—R 6 —NHCO—C 36 H 64+n —CONH—R 6 —NHCO—R 3 , R 1 —NHCO—R 6 —CONH—C 36 H 64+n —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 4 —CONH—C 36 H 64+n —CONH—R 5 —CONH—R 3 , R 1 —CONH—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —NHCO—R 3 or R 1 —NHCO—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —CONH—R 3 , R 1 —NHCO—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —CONH—R 3 , or R 1 —CONH—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —NHCO—R 3 , wherein R 6  is the same or different cyclic group having from about 5 to about 8 carbon atoms, R 4  and R 3  are the same or different and comprise an alkylene having from 1 to about 200 carbon atoms, and R 1  and R 3  are the same or different and comprise a straight chain or branched alkyl group having from about 3 carbon atoms to about 200 carbon atoms, 
   
   
       16 . The method according to  claim 15 , wherein the amine is an alkyl amine having from 1 to about 5 carbon atoms and the at least one carboxylic acid is a straight chain or branched carboxylic acid having from 1 to about 200 carbon atoms. 
   
   
       17 . The method according to  claim 16 , wherein the at least one carboxylic acid includes at least one hydroxyl group substituent. 
   
   
       18 . The method according to  claim 16 , wherein the compound has a formula of R 1 —CONH—R 2  or R 2 —CONH—R 1 , wherein R 2  is alkyl group having from 1 to about 18 carbon atoms and R 1  is a straight chain or branched alkyl group having from about 3 carbon atoms to about 200 carbon atoms, and wherein R 2  and R 1  have the same number of carbon atoms or R 2  has less carbon atoms than R 1 . 
   
   
       19 . The method according to  claim 15 , wherein the amine is a cyclic di-amine having from 5 to about 8 carbon atoms and the at least one carboxylic acid is a straight chain or branched carboxylic acid having from 1 to about 200 carbon atoms. 
   
   
       20 . The method according to  claim 19 , wherein the at least one carboxylic acid includes at least one hydroxyl group substituent. 
   
   
       21 . The method according to  claim 19 , wherein the compound has a formula of R 1 —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 6 —NHCO—R 3  or R 1 —NHCO—R 6 —NHCO—R 3 , wherein R 6  is a cyclic group having from 5 to about 8 carbon atoms and R 1  and R 3  are the same or different straight chain or branched alkyl group having from about 3 carbon atoms to about 200 carbon atoms. 
   
   
       22 . The method according to  claim 15 , further comprising reacting the amine and the at least one carboxylic acid with a dimer acid, wherein the amine is a cyclic di-amine having from 5 to about 8 carbon atoms or an alkylamine having from 1 to about 200 carbon atoms, and the at least one carboxylic acid is a straight chain or branched carboxylic acid having from 1 to about 200 carbon atoms. 
   
   
       23 . The method according to  claim 22 , wherein the at least one carboxylic acid includes at least one hydroxyl group substituent. 
   
   
       24 . The method according to  claim 22 , wherein the compound has a formula of R 1 —CONH—R 6 —CONH—C 36 H 64+n —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —NHCO—C 36 H 64+n —NHCO—R 6 —NHCO—R 3 , R 1 —CONH—R 6 —NHCO—C 36 H 64+n —CONH—R 6 —NHCO—R 3 , R 1 —NHCO—R 6 —CONH—C 36 H 64+n —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 4 —CONH—C 36 H 64+n —CONH—R 5 —CONH—R 3 , R 1 —CONH—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —NHCO—R 3  or R 1 —NHCO—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —CONH—R 3 , R 1 —NHCO—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —CONH—R 3 , or R 1 —CONH—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —NHCO—R 3 , wherein R 6  is the same or different cyclic group having from 5 to about 8 carbon atoms, R 4  and R 5  are the same or different alkylenes having from 1 to about 200 carbon atoms, R 1  and R 3  are the same or different straight chain or branched alkyl groups having from about 3 carbon atoms to about 200 carbon atoms, and n is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. 
   
   
       25 . An ink composition comprising an ink vehicle and a colorant, wherein the ink vehicle comprises a compound selected from the group consisting of R 1 —CONH—R 2 , R 2 —CONH—R 1 , R 1 —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 CONH—R 3 , R 1 —CONH—R 6 —NHCO—R 3 , R 1 —NHCO—R 6 —NHCO—R 3 , R 1 —CONH—R 6 —CONH—C 36 H 64+n —CONH—R 6 —CONH—R 3 , R 1 —NHCO—R 6 —NHCO—C 36 H 64+n —NHCO—R 6 —NHCO—R 3 , R 1 —CONH—R 6 —NHCO—C 36 H 64+n —CONH—R 6 —NHCO—R 3 , R 1 —NHCO—R 6 —CONH—C 36 H 64+n —NHCO—R 6 —CONH—R 3 , R 1 —CONH—R 4 —CONH—C 36 H 64+n —CONH—R 5 —CONH—R 3 , R 1 —CONH—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —NHCO—R 3  or R 1 —NHCO—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —CONH—R 3 , R 1 —NHCO—R 4 —NHCO—C 36 H 64+n —CONH—R 5 —CONH—R 3 , and R 1 —CONH—R 4 —CONH—C 36 H 64+n —NHCO—R 5 —NHCO—R 3 , wherein R 1  and R 3  are the same or different straight chain or branched alkyl groups having from about 3 carbon atoms to about 200 carbon atoms, wherein R 2  is an alkyl group having from 1 to about 18 carbon atoms and R 2  and R 1  have the same number of carbon atoms or R 2  has less carbon atoms than R 1 , R 6  is the same or different cyclic group having from 5 to about 8 carbon atoms, and R 4  and R 5  are the same or different alkylenes having from 1 to about 200 carbon atoms, n is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and wherein R 1  and R 3  optionally include at least one hydroxyl group substituent.