Dispersants

Abstract

A dispersant of general Formula I T—(A) n (B) p —Z  (1) wherein T is hydrogen or a polymerisation terminating group; Z is an acidic or basic group or a moiety containing either an acidic or basic group; A and B are each, independently, oxyalkylene carbonyl groups derivable from δ-valerolactone, ε-caprolactone or alkyl substituted ε-caprolactone provided that both are not ε-caprolactone or δ-valerolactone; n and p are integers; and n+p is from 2 to 100; including salts thereof. Specific examples of dispersants are the reaction product of lauric acid, δ-caprolactone, 7-methyl-ε-caprolactone with PEI, the reaction product of lauric acid, ε-caprolactone, δ-valerolactone with PEI and the phosphate of the reaction product of dodecanol, ε-caprolactone and δ-valerolactone.

What is claimed is: 
     
       1. A dispersant of general Formula 1
   T—(A) n (B) p —Z  (1)
 
 
       wherein
 T is hydrogen or a polymerisation terminating group; 
 Z is an acidic or basic group or a moiety containing either an acidic or basic group where the basic group or moiety containing the basic group represented by Z is attached to T—(A) n (B) p — by an amide and/or salt link and where the acidic group is selected from sulphate, sulphonate, phosphate and phosphonate; 
 A and B are each, independently, oxyalkylene carbonyl groups derived from δ-valerolactone, or ε-caprolactone or alkyl substituted ε-caprolactone provided that both are not ε-caprolactone or δ-valerolactone, the group —(A) n (B) p — being derived from the copolymerisation of δ-valerolactone and ε-caprolactone; 
 n and p are integers; and 
 n+p is from 2 to 100; 
 
       including salts thereof. 
     
     
       2. A dispersant as claimed in  claim 1  wherein n+p is not greater than 20. 
     
     
       3. A dispersant as claimed in either  claim 1  or  claim 2  wherein A is derived from ε-caprolactone and B is derived from alkyl substituted ε-caprolactone. 
     
     
       4. A dispersant as claimed in either  claim 1  or  claim 2  wherein A is derived from ε-caprolactone and B is derived from either δ-valerolactone or alkyl substituted ε-caprolactone and the ratio of n:p is between 8:1 and 1:2. 
     
     
       5. A dispersant as claimed in  claim 1  wherein the alkyl substituent of ε-caprolactone is C 1-4 -alkyl. 
     
     
       6. A dispersant as claimed in  claim 5  wherein the alkyl substituent is methyl. 
     
     
       7. A dispersant as claimed in  claim 1  which comprises a poly (C 2-4 -alkyleneimine) (PAI) carrying at least two polyoxyalkylene carbonyl (POAC) chains of Formula 2 
       
         
           
           
               
               
           
         
       
       
        
           T—(O—V—CO)—  (2)
 
       
       wherein:
 V is a polyoxyakylenecarbonyl (POAC) chain moiety —(A) n (B) p —; and 
 T, n and p are as defined in  claim 1 . 
 
     
     
       8. A dispersant as claimed in  claim 7  wherein V is the group —(A) n (B) p — wherein A is an oxyalkylenecarbonyl group derived from ε-caprolactone and B is an oxyalkylenecarbonyl group derived from alkyl substituted ε-caprolactone or δ-valerolactone and the ratio of n:p is from 8:1 to 1:1. 
     
     
       9. A dispersant as claimed in  claim 7  of general Formula 3 
       
         
           
           
               
               
           
         
       
       wherein
 X—*—*—X represents poly(C 2-4 -alkyleneimine) (PAI); 
 Y is a polyoxyalkylenecarbonyl (POAC) chain linked to poly(C 2-4 -alkyleneimine) (PAI) via an amide or salt linkage; and 
 q is from 2 to 2000. 
 
     
     
       10. A dispersant as claimed in  claim 9  wherein the weight ratio off (Y) q  to poly(C 2-4 -alkyleneimine) (PAI) is between 30:1 and 1:1. 
     
     
       11. A dispersant as claimed in  claim 9  wherein the weight ratio of (Y) q  to poly(C 2-4 -alkyleneimine) (PAI) is between 15:1 and 10:1. 
     
     
       12. A dispersant as claimed in claim  1  7 wherein the MW of the poly(C 2-4 -alkyleneimine) (PAI) is from 1,000 to 100,000. 
     
     
       13. A dispersant as claimed in claim  1  7 wherein the poly(C 2-4 -alkyleneimine) (PAI) is polyethyleneimine. 
     
     
       14. A dispersant as claimed in  claim 1  wherein T is derived from a C 1-25 -aliphatic carboxylic acid optionally substituted by hydroxy, C 1-4 -alkoxy or halogen. 
     
     
       15. A dispersant as claimed in  claim 14  wherein the carboxylic acid is selected from glycolic, lactic, caproic, lauric, stearic, methoxyacetic, ricinoleic, 12-hydroxystearic, 12-hydroxydodecanoic, 5-hydroxydodecanoic, 5-hydroxydecanoic and 4-hydroxydecanoic acids. 
     
     
       16. A dispersant as claimed in  claim 15  wherein the carboxylic acid is lauric acid. 
     
     
       17. A dispersant as claimed in  claim 1  which having formula 1 wherein Z of formula 1 is an acidic group or contains an acidic group wherein said dispersant has Formula 5 
       
         
           
           
               
               
           
         
       
       
        
           A 0 —(—O—V—CO—)—D  (5)
 
       
       wherein
 A 1 A 0  and D are groups, one of which is or carries an acidic group and the other is a polymerisation terminating group which does not render the end-capped polyoxyalkylenecarbonyl (TPOAC) chain hydrophilic; 
 V is a polyoxyalkylenecarbonyl (POAC) chain moeity —(A) n (B) p —; 
 n and p are integers; and 
 n+p is from 2 to 100; 
 
       including salts thereof. 
     
     
       18. A dispersant as claimed in  claim 17  wherein when A 1  A 0  carries the acidic group, D is the residue of an alcohol, thiol or primary or secondary amine D 1 —K—H in which D 1  is an aliphatic or alicyclic group, K is O, S or NR in which R is H, alkyl, alkenyl, cycloalkyl or phenyl. 
     
     
       19. A dispersant as claimed in either  claim 17  or  claim 18  which has Formula 8
   [D 1 —J—(CO—V—O) n+p ] w -L 1 M  (8)
 
 
       wherein
 D 1  is unsubstituted C 1-50 -hydrocarbyl or C 1-50 -hydrocarbyl substituted by halogen, tertiary amino or C 1-6 -alkoxy; 
 J is O, NR or a direct link; 
 V is a polyoxyalkylenecarbonyl (POAC) chain moiety —(A) n (B) p   − ; 
 R is H, alkyl, alkenyl, cycloalkyl or phenyl; 
 L 1  is sulphate or phosphate, 
 M is a cation; 
 w is 1 or 2 and 
 n and p are integers; and 
 n+p is from 2 to 100. 
 
     
     
       20. A dispersant as claimed in claim  19  wherein J is O 17 or 18 which has Formula 8
   (D 1 —J—(CO—V—O)) w —L 1 M  (8)
 
 
       wherein 
       D 1  is unsubstituted C 1-50 -hydrocarbyl selected from aliphatic or alicyclic groups; 
       J is O, or NR; 
       V is a polyoxyalkylenecarbonyl (POAC) chain moiety —(A) n (B) p —; R is H, alkyl, alkenyl, cycloalkyl or phenyl; L 1  is sulphate or phosphate; M is a cation; w is 1 or 2 and n and p are integers; and n+p is from 2 to 100. 
     
     
       21. A dispersant as claimed in  claim 20  wherein J is 0 and D 1  is alkyl. 
     
     
       22. A dispersant as claimed in  claim 21  wherein D 1  is diodecanyl dodecanyl. 
     
     
       23. A dispersant as claimed in claim  19  20 wherein V is a polyoxyalkylenecarbonyl (POAC) chain moiety —(A) n (B) p — wherein A is an oxyalkylenecarbonyl group derived from ε-caprolactone, B is an oxyalkylenecarbonyl chain derived from alkyl-substituted ε-caprolactone or δ-valerolactone and the ratio of n:p is from 8:1 to 1:1. 
     
     
       24. A dispersant as claimed in claim  19  20 wherein M is an amine, alkanolamine or quaternary ammonium salt. 
     
     
       25. A dispersant as claimed in  claim 24  wherein the amine is n-butylamine, diethanolamine or diaminopropylamine. 
     
     
       26. A dispersant as claimed in claim  19  20 wherein L 1  is phosphate. 
     
     
       27. A dispersant as claimed in  claim 26  wherein the ratio of end-capped polyoxyalkylenecarbonyl (TPOAC) alcohol to phosphorus atom is between 3:1 and 1:1. 
     
     
       28. A process for making a dispersant as claimed in  claim 7  which comprises reacting a end-capped polyoxyalkylenecarbonyl (TPOAC) acid with a poly(C 2-4 -alkyeneimine) (PAI) at a temperature between 80 and 150° C. 
     
     
       29. A process for making a dispersant as claimed in  claim 28  wherein the end-capped polyoxyalkyienecarbonyl (TPOAC) polyoxyalkylenecarbonyl TPOAC acid is prepared by reacting a lactone(s) with an aliphatic carboxylic acid in an inert atmosphere at from 150 to 180° C. in the presence of an esterification catalyst. 
     
     
       30. A process Process for making a dispersant as claimed in claim  19  20 which comprises polymerising a lactone(s) in the presence of a monohydric alcohol or a primary or secondary monoamine to form a end-capped polyoxyalkyienecarbonyl polyoxyalkylenecarbonyl (TPOAC) alcohol and reacting the TPOAC alcohol with a phosphating agent. 
     
     
       31. A composition comprising a particulate solid and a dispersant as claimed in  claim 1 . 
     
     
       32. A dispersion comprising a dispersant as claimed in  claim 1 , a particulate solid and an organic medium. 
     
     
       33. A dispersion as claimed in  claim 32  wherein the organic medium is a polar organic liquid. 
     
     
       34. A mill-base comprising a dispersant as claimed in  claim 1 , a particulate solid and a film-forming resin. 
     
     
       35. A paint or ink comprising a dispersant as claimed in  claim 1 . 
     
     
       36. An end-capped polyoxyalkylenecarbonyl (TPOAC) acid of Formula 12
   T—(O—V—CO) n+p —OH T—(O—V—CO)—OH  (12)
 
 
       wherein
 T is a polymerisation terminating group; 
 V is a polyoxyalkylenecarbonyl (POAC) chain moiety —(A) n (B) p —; 
 A and B are each, independently, oxyalkylenecarbonyl groups derived from δ-valerolactone, or ε-caprolactone or alkyl-substituted ε-caprolactone provided that both are not ε-caprolactone or δ-valerolactone, the moiety —(A) n (B) p — being derived from the copolymerisation of δ-valerolactone and ε-caprolactone; 
 n and p are integers; and 
 n+p is from 2 to 100. 
 
     
     
       37. An end-capped polyoxyalkylenecarbonyl (TPOAC) alcohol of Formula 13
   D 1 —J—(CO—V—O) n+p H D 1 —J—(CO—V—O)—H  (13)
 
 
       wherein
 D 1  is an unsubstituted aliphatic or alicyclic group, 
 J is O, NR or a direct link; 
 R is H, alkyl, alkenyl, cycloalkyl or phenyl; 
 V is a polyoxyalkylenecarbonyl (POAC) chain moiety —(A) n (B) p —; 
 A and B are each, independently, oxyalkylenecarbonyl groups derived from δ-valerolactone, or ε-caprolactone or alkyl-substituted ε-caprolactone provided that both are not ε-caprolactone or δ-valerolactone, the moiety —(A) n (B) p — being derived from the copolymerisation of δ-valerolactone and ε-caprolactone; 
 n and p are integers; and 
 n+p is from 2 to 100. 
 
     
     
       38. A paint or ink comprising a composition as claimed in  claim 31 . 
     
     
       39. A paint or ink comprising a millbase as claimed in  claim 34 .