# US 7,407,544 B2 · Polymeric dispersants based on addition of amines to dialkylsuccinyl succinate or its derivatives > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,407,544 B2 - Document ID: US7407544B2 - Status: Granted - Kind: B2 - Application number: 11/581,481 - Filed: 2006-10-17 - Published: 2008-04-17 - Granted: 2008-08-05 - Earliest claimed: 2006-10-17 - Assignees: Sun Chemical Corporation - Inventors: Tatiana N. Romanova; Ed Sung; Russell J. Schwartz - Web page: https://patentgrep.com/patent/US7407544B2 ## CPC - C09B 67/0066: {Aqueous dispersions of pigments containing only dispersing agents} - C09B 48/00: Quinacridones - C09B 67/0069: {Non aqueous dispersions of pigments containing only a solvent and a dispersing agent} - C09K 23/16: Amines or polyamines - C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Dispersants for pigments as well as dispersions of pigments containing them, and compositions such as inks and coatings containing them are described. The dispersants are the reaction product of a dialkylsuccinyl succinate and an amine. ## Claims ### Claim 1 A pigment dispersant which is the reaction product of a dialkylsuccinyl succinate and one or more amines of which at least one is a polymeric amine having a number average molecular weight of at least about 200. ### Claim 2 (depends on 1) The pigment dispersant of claim 1 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amine-terminated poly(alkylene oxide). ### Claim 3 (depends on 1) The pigment dispersant of claim 1 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is a aminobenzamide containing amine. ### Claim 4 (depends on 1) The pigment dispersant of claim 1 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amino-N-poly(alkylene or alkyleneoxy)-benzamide containing amine. ### Claim 5 (depends on 1) The pigment dispersant of claim 1 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and an amine is and X1 through X5 are individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonates, sulfates, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric and at least one is polymeric. ### Claim 6 (depends on 1) The pigment dispersant of claim 1 in which the reaction product is of the formula or an isomer thereof, or a mixture thereof; wherein m is 1 to 10; R′″ is alkyl; R1, R2 and R3 are the same or different aliphatic, ether, ester, ketone, amide, urea, urethane group or combination thereof; provided that at least one of R1, R2 and R3 is polymeric. ### Claim 7 (depends on 6) The pigment dispersant of claim 6 in which R′″ is lower alkyl, and at least one of R1, R2 and R3 comprises a poly(alkyleneoxy) moiety or an amino-N-(alkylene or alkyleneoxy)-benzeneamido moiety. ### Claim 8 (depends on 6) The pigment dispersant of claim 6, wherein the dialkylsuccinyl succinate is a dimethylsuccinyl succinate and at least one of R1, R2 and R3 is poly(alkyleneoxy)amino in which each alkyleneoxy group contains 2 or 3 carbon atoms. ### Claim 9 (depends on 5) The pigment dispersant of claim 5, wherein the dialkylsuccinyl succinate is a dimethylsuccinyl succinate and at least one of R1, R2 and R3 is amino-N-poly(alkylene or alkyleneoxy)-benzeneamido in which each alkylene or alkyleneoxy group contains 2 or 3 carbon atoms. ### Claim 10 (depends on 1) The pigment dispersant of claim 1 in which the reaction product is of the formula or an isomer thereof, or a mixture thereof; wherein each of X1 through X9 is individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonate, sulfate, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric; provided that at least one of X1 through X9 is polymeric. ### Claim 11 (depends on 1) A method of preparing the pigment dispersant of claim 1 which comprises reacting a dialkylsuccinyl succinate with one or more mono- or di-amine, wherein at least one amine is polymeric having a number average molecular weight of at least about 200. ### Claim 12 (depends on 11) The method of claim 11 in which at least one amine is of the formula R—(NH2)n in which n is 1 or 2, and R is selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkynyl, alkynylene, aryl, arylene, oxy, amino carbonyl, carbocyclic, heterocyclic, or a combination thereof. ### Claim 13 (depends on 11) The method of claim 11 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and in which an amine is an alkyleneoxy-containing amine, a 4-aminobenzamido-containing amine or an amine containing an aminobenzamido moiety and an alkylene or alkyleneoxy moiety. ### Claim 14 (depends on 13) The method of claim 13 in which the dialkylsuccinyl succinate is a dimethyl succinyl succinate and in which each alkylene moiety in the amine contains 2 or 3 carbon atoms. ### Claim 15 (depends on 13) The method of claim 13 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and in which the amine is and X1 through X6 are individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonates, sulfates, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric and at least one is polymeric. ### Claim 16 (depends on 1) A method of dispersing a pigment in a liquid which comprises combining together a liquid, a pigment and a dispersant of claim 1. ### Claim 17 (depends on 2) A method of dispersing a pigment in a liquid which comprises combining together a liquid, a pigment and a dispersant of claim 2. ### Claim 18 (depends on 6) A method of dispersing a pigment in a liquid which comprises combining together a liquid, a pigment and a dispersant of claim 6. ### Claim 19 (depends on 10) A method of dispersing a pigment in a liquid which comprises combining together the liquid, the pigment and a dispersant of claim 10. ### Claim 20 A composition comprising the combination of a pigment with a pigment dispersant which is the reaction product of a dialkylsuccinyl succinate and one or more amines of which at least one is a polymeric amine having a number average molecular weight of at least about 200. ### Claim 21 (depends on 20) The composition of claim 20 in which the reaction product is of the formula or an isomer thereof, or a mixture thereof; wherein each of X1 through X9 is individually selected from the group consisting of R′, OR′, COR′. COOR′, OCOR′, carboxylate, halogen. CN, NR′2, SO3H, sulfonate, sulfate, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric; provided that at least one of X1 through X9 is polymeric. ### Claim 22 (depends on 20) The composition of claim 20 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and an amine is and X1 through X5 are individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonates, sulfates, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′. in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric and at least one is polymeric. ### Claim 23 (depends on 20) The composition of claim 20 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amino-N-poly(alkylene or alkyleneoxy)-benzamide containing amine. ### Claim 24 (depends on 20) The composition of claim 20 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is a aminobenzamide containing amine. ### Claim 25 (depends on 20) The composition of claim 20 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amine-terminated poly(alkylene oxide). ### Claim 26 A composition comprising a pigment, an ink or coating carrier and a pigment dispersant which is the reaction product of a dialkylsuccinyl succinate and one or more amines of which at least one is a polymeric amine having a number average molecular weight of at least about 200. ### Claim 27 (depends on 26) The composition of claim 26 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amine-terminated poly(alkylene oxide). ### Claim 28 (depends on 26) The composition of claim 26 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is a aminobenzamide containing amine. ### Claim 29 (depends on 26) The composition of claim 26 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and the polymeric amine is an amino-N-poly(alkylene or alkyleneoxy)-benzamide containing amine. ### Claim 30 (depends on 26) The composition of claim 26 in which the dialkylsuccinyl succinate is a di(lower alkyl)succinyl succinate and an amine is and X1 through X5 are individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonates, sulfates, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric and at least one is polymeric. ### Claim 31 (depends on 26) The composition of claim 26 in which the reaction product is of the formula or an isomer thereof, or a mixture thereof; wherein each of X1 through X9 is individually selected from the group consisting of R′, OR′, COR′, COOR′, OCOR′, carboxylate, halogen, CN, NR′2, SO3H, sulfonate, sulfate, NR′(COR″), CONR′, PO3H2, phosphonate, N═NR′, SOR′, NSO2R′, in which R′ and R″ are the same or different and independently hydrogen, hydrocarbon or polymeric; provided that at least one of X1 through X9 is polymeric. ### Claim 32 A substrate having on at least a portion of it's surface, a composition comprising the combination of a pigment with a pigment dispersant which is the reaction product of a di(lower alkyl)succinyl succinate and one or more amines of which at least one is a polymeric amine having a number average molecular weight of at least about 200 and is an amine-terminated poly(alkylene oxide).