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WO2022132491A1 - Composition de dispersion de pigment stable - Google Patents

Composition de dispersion de pigment stable Download PDF

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Publication number
WO2022132491A1
WO2022132491A1 PCT/US2021/062128 US2021062128W WO2022132491A1 WO 2022132491 A1 WO2022132491 A1 WO 2022132491A1 US 2021062128 W US2021062128 W US 2021062128W WO 2022132491 A1 WO2022132491 A1 WO 2022132491A1
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WIPO (PCT)
Prior art keywords
acid
nucleophile
polyether
amine
dispersant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/US2021/062128
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English (en)
Inventor
Elliot COULBECK
Jonathan Burt
Le-yang ZHANG
Andrew J. Shooter
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Lubrizol Advanced Materials Inc
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Lubrizol Advanced Materials Inc
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Priority to CN202180084668.7A priority Critical patent/CN116670257A/zh
Publication of WO2022132491A1 publication Critical patent/WO2022132491A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black
    • C09C1/56—Treatment of carbon black ; Purification
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/52—Natural or synthetic resins or their salts

Definitions

  • the disclosed technology relates to a pigment dispersion which is stable at elevated temperatures and can be used in the preparation of pigmented polymers.
  • the present invention relates to a method of forming a pigment dispersion that is stable at elevated temperatures, comprising the steps of (1) preparing a dispersion containing (a) a solvent, having a boiling temperature (T), wherein the solvent comprises or consists of ethylene glycol or oligomers of ethylene glycol, (b) a pigment, for example, carbon black, and (c) a dispersant, (2) adding a material having a boiling point higher than temperature (T), and (3) heating the dispersion to at least the boiling temperature (T) of the solvent.
  • the dispersant used in the present invention comprises a salt of P and X.
  • P is a polyether functionalized polyacid intermediate formed via the reaction of (i) a polyacid Z, (ii) optionally polyether mono-nucleophile C, and (iii) optionally a non-polymeric mono-nucleophile D.
  • X is an alkali metal, an alkaline earth metal, ammonia, an amine or mixtures thereof.
  • polyacid Z has the formula (A)n-(B)m-(E)t-(G)q.
  • A is a carboxylic acid repeat unit having the structure
  • R is selected from H, CH3, or CH2COOH and R' is selected from H or COOH, with the proviso that R' can only be COOH when R is H.
  • B is an alkyl or aryl repeat unit having 2 to 30 carbon atoms, optionally substituted with halides, ethers, or nitro groups, with the proviso that B is substantially free of or is free of acid functionality.
  • G is a repeat unit having the structure where R'' is H or CH3
  • W is a direct link between a backbone carbon atom and the P or S atom of Y or hydrocarbylene linking group of 1-7 carbon atoms, which optionally includes ether, ester or amide linking groups
  • k is 1 or 2.
  • G is a repeat unit having the structure
  • R "' is H or CH3
  • J is ethylene oxide or propylene oxide with at least
  • n 10 - 200 or 20 to 100
  • m is 0 to 40 or 0 to 20
  • t is 0 to 20
  • q is 0 to 70, with the proviso that n is at least 30% of all repeat units (n + m + t + q).
  • Polyether mono-nucleophile C contains 6 to 70 ethylene glycol repeat units, and, optionally, contains propylene glycol and/or butylene glycol repeat units, with the proviso that at least 50%, or at least 70% of all repeat units are ethylene glycol.
  • the polyether mono-nucleophile C also contains a single alcohol, primary amine, or secondary amine group.
  • the non-polymeric mono-nucleophile D is a linear or branched, saturated or unsaturated alkyl or aryl chain having 1 to 22 carbon atoms and contains a single alcohol, primary amine, or secondary amine group and optionally one or more tertiary amine, halide, or nitro groups with the proviso that D is substantially free of or free of acid groups.
  • polyether functionalized polyacid P if q is 1 or greater, 0% to 50% of the total moles of repeat unit A are reacted with C or if q is 0, then 10% to 50% of the total moles of A are reacted with C. Also, in polyether functionalized polyacid P, 0% to 30% of the total moles of A is reacted with D.
  • one or more of the carboxylic acid repeat units of A react with polyether nucleophile C and/or non-polymeric nucleophile D to form one or more bonds, where the bonds are selected from (i) an ester bond formed from the reaction product of an alcohol group of polyether nucleophile C and/or non-polymeric nucleophile D with a carboxylic acid repeat unit of A; (ii) salt bonds and/or amide bonds formed from the reaction product of a primary or secondary amine of polyether nucleophile C and/or non-polymeric nucleophile D with a carboxylic acid repeat unit of A; or (iii) imide bonds formed from the reaction product of a primary amine group of polyether nucleophile C and/or non-polymeric nucleophile D with two adjacent carboxylic acids from the same repeat unit A or adjacent repeat unit A.
  • the present invention also includes the use of the dispersant described above to provide a stable pigment dispersion at elevated temperatures.
  • hydrocarbyl in this specification will mean hydrocarbon like and can include up to one oxygen or nitrogen for every four carbon atoms in the group, but preferably is just carbon and hydrogen atoms.
  • Hydro- carbylene will mean hydrocarbon with two hydrogen atoms removed. Hydro- carbylene will also optionally include up to one oxygen or nitrogen atom for every two carbon atoms in the group, but preferably is just carbon and hydrogen.
  • the present invention relates to a method of forming a pigment dispersion that is stable at elevated temperatures.
  • the method comprises the steps of (1) preparing a dispersion containing (a) a solvent, having a boiling temperature (T), wherein the solvent comprises or consists of ethylene glycol or oligomers of ethylene glycol, (b) a pigment, and (c) a dispersant, (2) adding a material having a boiling point higher than temperature (T), and (3) heating the dispersion to a temperature that is at least the boiling temperature (T) of the solvent.
  • T boiling temperature
  • the invention also includes the use of a dispersant to provide a stable pigment dispersion at elevated temperatures.
  • the solvent used in the present invention comprises ethylene glycol or oligomers of ethylene glycol or mixtures thereof.
  • the solvent comprises or consists of ethylene glycol.
  • the solvent comprises or consists of oligomers of ethylene glycol.
  • the oligomers may comprise 2 to 5 repeat units of ethylene glycol. If the dispersion used in the present invention contains one or more other co-solvents, these solvents may be selected from water, alkanols, alkane carboxylic acids and esters of alkane carboxylic acids among other solvents known to those skilled in the art.
  • the solvent will have a boiling temperature of at least 180°C, or at least 190°C, or at least 195°C, or at least 200°C.
  • ethylene glycol has a boiling temperature of 197°C.
  • the boiling temperature refers to the initial boiling temperature, or the temperature at which any of the components of a mixture boil.
  • the dispersant used in the present invention comprises a salt of P and X.
  • P is a polyether functionalized polyacid intermediate formed via the reaction of (i) a polyacid Z, (ii) optionally polyether mono-nucleophile C, and (iii) optionally a non-polymeric mono-nucleophile D.
  • X is an alkali metal, an alkaline earth metal, ammonia, an amine or mixtures thereof.
  • the polyacid Z has the formula (A)n-(B)m-(E)t-(G)q.
  • A is a carboxylic acid repeat unit having the structure R is selected from H, CH3, or CH2COOH and R' is selected from H or COOH, with the proviso that R' can only be COOH when R is H.
  • A may be derived from free radically polymerizable unsaturated monomers with one or more carboxylic acid group (such as acrylic, methacrylic, maleic, fumaric, itaconic, mesaconic, or citraconic acids or mixtures thereof).
  • B is an alkyl or aryl repeat unit having 2 to 30 carbon atoms, optionally substituted with halides, ethers, or nitro groups, with the proviso that B is substantially free of or is free of acid functionality.
  • B may be derived from a free radically polymerizable monomer containing a carbon-to-carbon double bond without a carboxylic group or acids from sulfur or phosphorus.
  • Such repeat units of B will be from styrene, ethylene, propene, butenes, (meth)acrylate esters of (meth)acrylic acid and Ci-Cis alcohols, and (meth)acrylate hydroxyl ester such as hydroxyl ethyl (meth)acrylate, hydroxyl butyl (meth)acrylate, vinyl acetate, (meth)acrylamides, vinyl substituted heterocyclics such as vinyl pyrrolidinone, vinyl imidazole, vinyl carbazole, 2-vinylpyridine, and 4-vinylpyridine.
  • E is derived from anionic monoethyleni- cally unsaturated monomers containing sulphonic acid groups and/or phosphoric acid groups and/or phosphonic acid groups which may be in the free acid form or salt.
  • the term "phosphoric acid group” and "phosphonic acid group” of a phosphorus containing repeat unit refers to a phosphorus oxo acid having a POH moiety in which the hydrogen atom is ionizable. Also included in the term “phosphoric acid group” and “phosphonic acid group” are salts of the phosphorus oxo acid. In its salt or basic form, the phosphorus acid group has a cation such as an alkali earth or alkaline earth metal, an ammonium, substituted ammonium, quaternary ammonium or pyridinium ion replacing at least one acid proton.
  • the sul- phonic acid group has a cation such as an alkali earth or alkaline earth metal, an ammonium, substituted ammonium, quaternary ammonium or pyridinium ion replacing at least one acid proton.
  • anionic monoethylenically unsaturated monomers containing sulphonic acid groups which may be in the free acid form or salt include allylsulfonic acid, methallyl sulfonic acid, styrenesulfonic acid, vinylsulfonic acid, vinyl benzylsulphonic acid, allyloxybenzenesulfonic acid, 2-acrylamido-2-meth- ylethanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, 2-acrylamido-2- methylbutanesulfonic acid, 2-methacrylamido-2-methylethanesulfonic acid, 2-meth- acrylamido-2-methylpropanesulfonic acid, 2-methacrylamido-2-methylbutanesul- fonic acid, acryloyloxymethylsulfonic acid, 2-(acryloyl)oxyethylsulfonic acid, 3-(ac- ryloyl)
  • anionic monoethylenically unsaturated monomers containing phosphoric or phosphonic acid groups which may be in the free acid form or salt include monovinyl phosphate, monoallyl phosphate, 3-butenylphosphonic acid, mono-3 -butenyl phosphate, mono(4-vinyloxybutyl) phosphate, the phosphate esters of [hydroxyalkyl(meth)acrylates, hydroxy alkyl(meth)acrylamides or their polyalkox- ylate derivatives of molecular weight Mn 150-700 such as 2-hydroxy- ethyl(meth)acrylate, hydroxypropyl(meth)acrylate and 4-hydroxybutyl(meth)acry- late, N-hydroxyethylacrylamide, N-hydroxyethylmethacrylamide hydroxypoly(eth- yleneoxide)(meth)acrylate, and polypropyleneglycol (meth)acrylate], mono(2-hy--
  • Suitable phosphonic acid monomers include vinyl phosphonic acid, allyl phosphonic acid, 2-acrylamido-2-methylpropanephosphonic acid, a-phosphonostyrene, 2- methylacrylamido-2-methylpropanephosphonic acid.
  • Further suitable phosphorus functional monomers are 1,2-ethylenically unsaturated (hydroxy)phosphinylalkyl (meth)acrylate monomers, disclosed in US 4,733,005, and include (hydroxy)phos- phinylmethyl methacrylate.
  • One preferred monomer is vinylphosphonic acid, or hydrolyzable esters thereof.
  • G is a repeat unit having the structure where R'" is H or CH3, J is ethylene oxide or propylene oxide with at least 50% or at least 70% of J being ethylene oxide, L is H or a linear or branched, saturated or unsaturated chain having 1 to 20 carbon atoms, optionally containing a carbonyl group to form an ester with an oxygen atom between J and L, and r is 1 to 100 or 10 to 50.
  • n 10 - 200 or 20 to 100
  • m is 0 to 40 or 0 to 20
  • t is 0 to 20
  • q is 0 to 70, with the proviso that n is at least 30% of all repeat units (n + m + t + q).
  • the polyacid Z will be primarily poly(meth)acrylic acid (e.g. > 50% of the repeating units will be conventional repeat unit from polymerizing acrylic acid).
  • the polyacid will include from 5 to 50 number percent of repeating units from maleic acid or a maleic anhydride.
  • the polyacid Z may include a variety of copolymers such as poly(meth)acrylic-co-maleic acid; polyacrylic-co-itaconic acid; polyacrylic-co- AMPS acid, polyitaconic-co-acrylate acid; polyitaconic-co-acrylamide acid; etc. in place of poly(meth)acrylic acid
  • Polyether mono-nucleophile C contains 6 to 70 ethylene glycol repeat units, and, optionally, contains propylene glycol and/or butylene glycol repeat units, with the proviso that at least 50%, or at least 70% of all repeat units are ethylene glycol. In one embodiment, C contains from 1 to 15 or even 1 to 10 propylene glycol repeat units.
  • the polyether mono-nucleophile C also contains a single alcohol, primary, amine, or secondary amine group.
  • Polyether mono-nucleophile may be derived from a poly(alkyleneox- ide) monoalkyl ether monoamine.
  • Exemplary monoamine compounds of this type are commercially available as the Surfonamine® or JeffamineTM amines from Huntsman Corporation. Specific examples of Surfonamine® amines are L-100 (propylene oxide to ethylene oxide mole ratio of 3: 19), L-207 (propylene oxide to ethylene oxide mole ratio of 10:32), L-200 (propylene oxide to ethylene oxide mole ratio of 3:41), L-300 (propylene oxide to ethylene oxide mole ratio of 8:58).
  • C may be derived from a poly(alkyleneoxide) monoalkyl ether.
  • These mono-alkyl ethers are available from a variety of sources such as Sigma-Aldrich, Croda, BASF, Dow, and Ineos.
  • the non-polymeric mono-nucleophile D is a linear or branched, saturated or unsaturated alkyl or aryl chain having 1 to 22 carbon atoms and contains a single alcohol, primary amine, or secondary amine group and optionally one or more tertiary amine, halide, or nitro groups with the proviso that D is substantially free of or free of acid groups.
  • the primary amine may include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, 2- ethylhexyl amine, nonylamine, decylamine, undecylamine, dodecylamine, tridecyl amine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, nonadecylamine, eicosylamine, or mixtures thereof.
  • the amine may include benzyl amine, 2-phenylethanamine (often referred to as phenylethyl amine), 3- phenylpropanamine, 4-phenylbutanamine, or mixtures thereof.
  • the primary amine may include benzyl amine or 2- phe- nylethanamine.
  • the primary amine may include 2-phenylethanamine.
  • the secondary amine may be, for example, dimethyl amine, diethyl amine, dipropyl amine, dibutyl amine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, N,N-diisopropylamine, N,N- diisobutylamine, diisoamylamine, piperidine, N,N-dimethylpiperidin-4-amine, N,N- dibenzylamine, N-benzylmethylamine, N-phenyl-N-propylamine, N-methyl-phene- thylamine, N-methyl-N-(l-phenylethyl)amine, 4-Bromo-N-methylbenzylamine, or 4-Fluoro-N-methylbenzylamine.
  • Suitable mono-functional nucleophiles D containing a hydroxyl functionality include alcohols with optionally substituted Cl-22 hy- drocarbylene groups such as methanol, ethanol, propan- l-ol, propan-2-ol, butanol, isobutanol, neopentyl alcohol, hexanol, octan-l-ol, 2-ethylhexanol, decanol, dodecanol, oleyl alcohol, stearyl alcohol, behenyl alcohol, cyclohexanol, benzyl alcohol, phenol, octylphenol, nonylphenol, phenylethanol, fluorinated alcohols such as lH,lH,2H,2H-perfluoro-l -decanol, C8-22 branched alcohols available under the trademark IsofolTM (ex Sasol).
  • the polyacid Z may be prepared by processes known to a skilled person and functionalized with the polyether mono-nucleophile C and, optionally, non-pol- ymeric nucleophile D, by any method known in the art.
  • the polyacid may be prepared by esterification or amidation of poly(meth)acrylic acid or poly(meth)acrylic acid/maleic acid copolymer, or polymerization of (meth)acrylic acid with (meth)acrylic esters and/or amides or polymerization of (meth)acrylic acid with maleic acid (or maleic anhydride), (meth)acrylic esters and/or amides and maleic acid esters and/or amides by any known polymerization technique or a combination of polymerization techniques using a bulk, solution, suspension or emulsion process.
  • the polymerization may comprise of a radical, anionic, cationic, atom transfer or group transfer polymerization process or combinations thereof.
  • one or more of the carboxylic acid repeat units of A react with, polyether nucleophile C and/or non-polymeric nucleophile D to form one or more bonds, where the bonds are selected from (i) an ester bond formed from the reaction product of an alcohol group of polyether nucleophile C and/or non-polymeric nucleophile D with a carboxylic acid repeat unit of A; (ii) salt bonds and/or amide bonds formed from the reaction product of a primary or secondary amine of polyether nucleophile C and/or non-polymeric nucleophile D with a carboxylic acid repeat unit of A; or (iii) imide bonds formed from the reaction product of a primary amine group of polyether nucleophile C and/or non-polymeric nucleophile D with two adjacent carboxylic acids from the same repeat unit A or adjacent repeat unit A.
  • the polymer intermediate P may be obtained or obtainable by reacting polyacid Z (typically with a number average molecular weight between 700 to 50,000, or 700 to 28,000), either as an aqueous solution or a solid with polyether mono-nucleophile C and, optionally, non-polymeric nucleophile D, optionally in the presence of a catalyst, such as an acid or base catalyst.
  • polyacid Z typically with a number average molecular weight between 700 to 50,000, or 700 to 28,000
  • a catalyst such as an acid or base catalyst.
  • polyether intermediate P if q is 1 or greater, 0% to 50% of the total moles of repeat unit A are reacted with C.
  • polyether intermediate P if q is 0, then 10% to 50% of the total moles of A are reacted with C.
  • 0% to 30% of the total moles of A is reacted with D.
  • Polymer intermediate P is subsequently reacted with X weight ratio of the P to X of 30: 1 to 1 : 1 or 15: 1 to 1 : 1 to form a salt.
  • the reactions described herein are performed under conditions that would be known and understood to be useful by those skilled in the art.
  • the dispersant used in the present invention comprises a salt of P and X.
  • X is an alkali metal, an alkaline earth metal, ammonia, an amine or mixtures thereof.
  • the salt may be formed by using ammonia, an amine, quaternary ammonium or pyridinium cation as X.
  • amines are methylamine, diethylamine, ethanolamine, diethanolamine, hexylamine, 2-ethylhex- ylamine and octadecylamine.
  • the quaternary ammonium cation may be a quaternary ammonium cation or a benzalkonium cation.
  • the quaternary ammonium cation may contain one or two alkyl groups containing from 6 to 20 carbon atoms.
  • Examples of quaternary ammonium cations are tetraethyl ammonium, N-octadecyl-N,N,N-trime- thyl ammonium; N,N-didodecyl-N,N-dimethyl ammonium, N-benzyl-N,N,N-trime- thyl ammonium and N-benzyl-N-octadecyl-N,N-dimethyl ammonium cation.
  • the salt may be formed by using an alkali metal or alkaline earth metal as X.
  • an alkali metal or alkaline earth metal for example, monovalent alkali metals (Li, Na, K, Rb, Cs, and Fr) or divalent alkaline earth metals (Be, Mg, Ca, Sr, Ba, and Ra) may be used.
  • lithium, sodium and potassium may be used.
  • X can be a polyamine such as poly(vinyla- mine), alkylenepolyamine, or polyallylamine or poly(C2-6-alkyleneimine), for example, in one embodiment, polyethyleneimine.
  • the polyamine or polyalkyleneimine may be linear or branched.
  • the polyamine or polyalkyleneimine may have a number average molecular weight of from 140-100, OOOg/mole; more desirably from 140 to 75,000; or preferably from 200 to 10,000 or 20,000.
  • X may have a total of at least four primary and/or secondary amine groups per molecule and more desirably at least six primary and/or secondary amine groups.
  • Linear polyethyleneimine may be prepared by the hydrolysis of poly(N- acyl) alkyleneimines as described, for example, by Takeo Saegusa et al in Macromolecules, 1972, Vol 5, page 4470.
  • Polypropyleneimine dendrimers are commercially available from DSM Fine Chemicals and poly(amidoamine) dendrimers are available as “Starburst” dendrimers from Aldrich Chemical Company.
  • Alkylenepolyamines may be characterized as having less than two, usually less than 1% (by weight) material boiling below about 200°C and include still bottoms such as ethylene polyamine still bottoms obtained from the Dow Chemical Company of Freeport, Texas [0034]
  • X is a polyimine, in one exemplary embodiment, it is poly (C2-6- alkyleneimine) or polyethyleneimine (PEI).
  • the polyimine may be linear or especially branched.
  • both P and X may have multiple co-reactive groups, in some cases, there may be more than one bond (as defined above) between them. It is also acknowledged that more than one P can be bonded to a single X. Similarly, there can be more than one X chemically bonded to a single P.
  • polymer intermediate P and species X are reacted together such that -CO2H or -CCL" of P reacts with the amine, metal, or other basic groups of X to give ionic salt bonds and/or covalent bonds or a mixture of ionic salt bonds and covalent bonds.
  • the weight ratio of P to X 30: l to 1 : 1, or 15: 1 to 1 : 1, or 14: 1, 13 : 1, 12: 1, 11 : 1, 10: 1, 9: 1, 8: 1, 7: 1, 6: 1, 5: 1, 4: 1, 3 : 1, or 2: 1.
  • the reaction product or co-polymer product of P and X may be presented as a neat polymer or a polymer in an organic solvent. This can be achieved by dissolving the neat reaction product or co-polymer product into the solvent, or by carrying out the synthesis of the reaction product or co-polymer product in the solvent.
  • the solvent comprises or consists of ethylene glycol, oligomers of ethylene glycol, or mixtures thereof.
  • the reaction product of P and X can be further functionalized to adapt their properties and application performance to specific requirements.
  • the modification reactions below may be combined where necessary, to give multiply modified polyacid polybasic addition compounds. Where two or more modifying reactions are to be carried out in succession, it should be ensured that enough groups are available that are reactive for one or more subsequent reactions in the molecule.
  • the stated modifications are advantageous embodiments of the present invention and can be realized by: a) reaction of one or more of the remaining free amino groups of the aminic polybasic species with isocyanates, lactones, anhydrides, epoxides, cyclic carbonates, or (meth)acrylates; b) salification and/or reaction of one or more of the remaining free amino groups of the aminic polybasic species with mono or polycarboxylic acids, mineral acids, phosphorus and polyoxometallate containing acids or strong acids; c) oxidation of one or more of the of the remaining free amino groups of the aminic polybasic species to nitrogen oxides; d) quaternization of one or more of the remaining free amino groups of the aminic polybasic species; or e) reaction of one or more of the remaining free amino groups of the aminic polybasic species with one or more mono amino-reactive group terminated polymer(s) of MW 150 - 3000.
  • any remaining amino groups may take place in a way which is known to the skilled person.
  • salification and quaterniza- tion of the amino nitrogen atom can be achieved using mineral acids, strong acids, alkyl sulfates, alkyl or aralkyl halides, halocarboxylic esters, alkyl oxalates or epoxides.
  • Such quaternization is preferred when, for example, amino groups will react with a binder system into which the pigment paste is incorporated and cause flocculation.
  • Suitable reagents for this purpose include hydrochloric acid, acetic acid, sulphuric acid, alkyl sulphonic acids, alkyl hydrogen sulphates or aryl sulphonic acids.
  • Quaternizating agents include dimethyl sulphate, benzyl chloride, methyl halides such as chlorine, bromine and iodine, dimethyl oxalate, ethylene oxide, propylene oxide and styrene oxide in the presence of acids, and propane (or butane) sultone.
  • Salification and/or reaction of one or more of the remaining free amino groups of the aminic polybasic species with mono or polycarboxylic acids or phosphorus containing acids are disclosed in JP9,157,374, US2010/0017973 and US2013/0126804.
  • suitable mono carboxylic acids include optionally substituted C1-50 aliphatic monocarboxylic acids such as acetic acid, propionic acid, caproic acid, caprylic acid, 2-ethylhexanoic acid, nonanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, stearic acid, arachidic acid, erucic acid, behenic acid, methoxyacetic acid, mixtures of fatty acids derived from oils from naturally occurring sources such as sunflower oil, rape seed oil, castor oil and olive oil, branched alkyl carboxylic acids available under the trademark IsocarbTM (ex Sasol), UnicidTM acids which are linear C25-50 synthetic primary acids commercially available from Baker Hughes and aromatic carboxylic acids such as benzoic acid, salicylic acid and naphthoic acid.
  • C1-50 aliphatic monocarboxylic acids such as acetic acid, propionic
  • suitable polycarboxylic acids include succinic acid, malonic acid, adipic acid, sebacic acid, malic acid, fumaric acid, citric acid and tartaric acid.
  • suitable phosphorus containing acids include phosphoric acid and phosphorous acid.
  • suitable poly oxometallate containing acids include phosphomolybdic acid, phosphotungstic acid and silicomolybdic acid.
  • Reaction of one or more of the remaining free amino groups of the aminic polybasic species with anhydrides are disclosed in US6,878,799 and US7,767, 750.
  • suitable anhydrides include maleic anhydride, succinic anhydride, phthalic anhdride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, trimellitic anhydride, Ci -20 alkenyl and alkyl succinic anhydrides.
  • the reaction products can be in the form of an amide and/or the corresponding salt when a carboxylic acid terminated polymer is used, a salt when sulfonic acid, sulfuric acid, phosphonic acid and phosphoric acid terminated polymers are used and a covalent bond is formed between the NH functionality of the amino group and i) an isocyanate terminated polymer to give a urea, ii) an epoxide terminated polymer to ring open the epoxy group giving an amino alcohol, and iii) a (meth)acrylate terminated polymer via a Michael addition across the double bond.
  • mono-reactive terminated polymers can be based on polyesters, polyethers, polyether/polyester, polyamide, polyesteramide, poly(meth)acrylates, polyurethanes and mixtures thereof. Particularly useful mono-reactive polymers have been disclosed in various patents.
  • polyesters are derived from the polymerisation of:- one or more of a hydroxycarboxylic acid and/or a lactone optionally in the presence of initiator molecules containing a carboxylic acid or ester functionality; or one or more of a diol with one or more of a dibasic acid/ anhydride optionally in the presence of initiator molecules containing a carboxylic acid or ester functionality; b) the polyesteramides are derived from the polymerisation of:- one or more of a hydroxycarboxylic acid and/or a lactone with one or more of an
  • Suitable hydroxy carboxylic acids and lactones include ricinoleic acid, 12-hydroxystearic acid, 6-hydroxy caproic acid, 5-hydroxy valeric acid, 12-hydroxy dodecanoic acid, 5-hydroxy dodecanoic acid, 5-hydroxy decanoic acid, 4-hydroxy decanoic acid, 10-hydroxy undecanoic acid, lactic acid, glycolic acid, P-propiolactone, P-butyrolactone, optionally Ci-6-alkyl substituted s-ca- prolactone and optionally Ci-6-alkyl substituted 6-valerolactone such as s-caprolac- tone and the 7-methyl-, 3-methyl-, 5-methyl-, 6-methyl-, 4-methyl-, 5 -tetra-butyl-, 4,4,6-trimethyl- and 4,6,6-trimethyl- s-caprolactone, 6-valerolactone, P-methyl-6- valerolactone or mixtures thereof.
  • suitable diols include alkylene glycols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-hexanediol, diols with ether linkages such as diethylene glycol, dipropylene glycol, tripropylene glycol and tri ethylene glycol.
  • suitable polyalkylene glycols include polyethylene glycols, polypropylene glycols, polybutylene glycols, mixed block and random copolymers of polyethylene glycol and polypropylene glycol (Pluronic and reverse pluronic ex BASF) with MW less than 1000.
  • Suitable dibasic acids and anhydrides include maleic anhydride, succinic anhydride, glutaric anhydride, fumaric acid, malonic acid, adipic acid, sebacic acid, phthalic anhydride, and cyclohexane dicarboxylic anhydride.
  • suitable aminocarboxylic acids include sarcosine, beta-alanine, 4-aminobutyric acid, 6-aminocaproic acid and 11-aminoundecanoic acid.
  • suitable lactams include laurolactam and caprolactam.
  • suitable diamines include alkylene diamines such as ethylenediamine, 1,2-propylenediamine, 1,3-propylene diamine, the isomeric butylenediamines, pentanediamines, hexanediamines, heptanediamines, 1,12-diamino- dodecane, diaminocyclohexanes, and diamines with ether linkages such as 1 ,2-bis(2- aminoethoxy)ethane.
  • suitable polyetherdiamines include Jeffamine diamines commercially available from Huntsman such as D230, D400, ED600.
  • Suitable initiator molecules containing a carboxylic acid or ester group include optionally substituted C1-50 aliphatic monocarboxylic acids as described above and their methyl or ethyl esters.
  • Suitable examples of phosphate, sulphate and sulphonate terminated polyester polymers are disclosed in US4,861,380 and US6, 197,877 in which the polyesters are derived from the polymerisation of hydroxycarboxylic acids and/or lactones as disclosed above using initiator molecules containing a hydroxyl or amino functionality.
  • Suitable initiator molecules containing a hydroxyl functionality include alcohols with optionally substituted Cl-50 hydrocarbylene groups such as methanol, ethanol, propan- l-ol, propan-2-ol, butanol, isobutanol, neopentyl alcohol, hexanol, octan-l-ol, 2-ethylhexanol, decanol, dodecanol, oleyl al- chol, stearyl alcohol, behenyl alcohol, cyclohexanol, benzyl alcohol, phenol, octylphenol, nonylphenol, phenylethanol, fluorinated alcohols such as 1H,1H,2H,2H- perfluoro-1 -decanol, C8-36 branched alcohols available under the trademark IsofolTM (ex Sasol), UnilinTM alcohols which are linear C25-50 synthetic primary alcohols commercially available from Baker Hughes. Specific examples
  • Suitable examples of (meth)acrylate terminated polyester, polyesteramide and polyamide polymers are disclosed in EP713894, JP3,488,001, JP2010222522 and US8,202,935 in which the polyesters are derived from the polymerisation of hydroxy carboxylic acids and/or lactones as disclosed above using:- i. initiator molecules such as 2-hydroxyethylacrylate directly; ii. initiator molecules containing a hydroxyl functionality then subsequent transesterification reaction with a (meth)acrylate ester; iii.
  • initiator molecules containing a carboxylic acid or ester functionality as described above and then subsequent reaction with a (meth)acrylate ester containing a hydroxyl functionality such as 2-hydroxyethylacrylate or an epoxy functionality such as glycidyl methacrylate.
  • Suitable examples of phosphate, sulphate and sulphonate terminated polyether, polyether/polyester, polyether/polyurethane and polyether/polyester/poly- urethane polymers are disclosed in US5, 130,463, US5,151,218, US6,l l l,054, US6,310,123, US7,595,416 and US8,202,935 in which the polyethers are derived from the polymerisation of alkylene and alkarylene oxides such as ethylene oxide, propylene oxide, butylene oxide and styrene oxide using initiator molecules containing a hydroxyl or amino functionality as disclosed above.
  • polyether mono alcohols can be further reacted with one or more hydroxy carboxylic acids or lactones as disclosed above or with diols and diacids as described above to give the polyether polyester polymers containing an alcohol group which can then be phosphated as disclosed in US5, 130,463.
  • the polyether mono alcohols and polyether polyester monoalcohols can be reacted further with diols as disclosed above in combination with diisocyanates to give polyether polyurethane and poly ether polyester polyurethane polymers respectively containing an alcohol group which can then be phosphated as disclosed in US5, 130,463.
  • diisocyanates include hexamethylenediisocyanate (HDI), 2,4- and 2,6-toluenediisocyanate (TDI) , isophoronediisocyanate (IPDI), a,a-tetramethylxylene diisocyanate (TMXDI), di- phenylmethane-4, 4 -diisocyanate (4,4’ -MDI), diphenylmethane-2, 4 -diisocyanate (2,4’ -MDI) and di cyclohexylmethane-4, 4 -diisocyanate (HMDI)
  • Suitable examples of carboxylic acid terminated polyether polymers are disclosed in JP4,248,207, US7,767,750, US7,671,119, US7, 872,070, US8,076,409 and US8, 168,713 in which polymers are derived from i) the reaction of polyalkyleneglycol mono substituted ethers with halocarb oxy late salts such as sodium monochloroacetate and then acidified using hydrochloric acid; ii) the reaction of polyalkyleneglycol mono substituted ethers with acrylonitrile and then hydrolysed in the presence of acids such as hydrochloric acid; and iii) the reaction of polyetheramines with anhydrides.
  • Suitable examples of isocyanate terminated polyester and polyether polymers are disclosed in JP4,031,471, JP7, 149,855 and W02007/039605.
  • Suitable examples of epoxide or acetoacetoxy or cyclocarbonate terminated polyacrylate polymers are disclosed in US5,100,969.
  • the dispersion used in the present invention also includes one or more pigments or other particulate solid material.
  • the solid is an organic pigment from any of the recognised classes of pigments described, for example, in the Third Edition of the Colour Index (1971) and subsequent revisions of, and supplements thereto, under the chapter headed “Pigments”.
  • organic pigments are those from the azo, disazo, trisazo, condensed azo, azo lakes, naphthol pigments, anthanthrone, anthrapyrimidine, anthraquinone, benzimidazolone, carbazole, diketopyrrolopyrrole, flavanthrone, indigoid pigments, indanthrone, isodibenzanthrone, isoindanthrone, isoindolinone, isoindoline, isoviolanthrone, metal complex pigments, oxazine, perylene, perinone, pyranthrone, pyrazoloquinazolone, quin- acridone, quinophthalone, thioindigo, triarylcarbonium pigments, triphendioxazine, xanthene and phthalocyanine series, especially copper phthalocyanine and its nuclear halogenated derivatives, and also lakes of acid, basic and mor
  • the organic pigments are phthalocyanines, especially copper phthalocyanines, monoazos, disazos, indanthrones, anthranthrones, quinacridones, diketopyrrolopyrroles, perylenes and carbon blacks.
  • inorganic pigments include metallic oxides such as titanium dioxide, rutile titanium dioxide and surface coated titanium dioxide, titanium oxides of different colours such as yellow and black, iron oxides of different colours such as yellow, red, brown and black, zinc oxide, zirconium oxides, aluminium oxide, oxy-metallic compounds such as bismuth vanadate, cobalt aluminate, cobalt stannate, cobalt zincate, zinc chromate and mixed metal oxides of two or more of manganese, nickel, titanium, chromium, antimony, magnesium, cobalt, iron or aluminium, Prussian blue, vermillion, ultramarine, zinc phosphate, zinc sulphide, molybdates and chromates of calcium and zinc, metal effect pigments such as aluminium flake, copper, and copper/zinc alloy, pearlescent flake such as lead carbonate and bismuth oxychloride.
  • metallic oxides such as titanium dioxide, rutile titanium dioxide and surface coated titanium dioxide, titanium oxides of different colours such as yellow and
  • Inorganic solids include extenders and fillers such as ground and precipitated calcium carbonate, calcium sulphate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulphate, barium carbonate, magnesium oxide, magnesium hydroxide, natural magnesium hydroxide or brucite, precipitated magnesium hydroxide, magnesium carbonate, dolomite, aluminium trihydroxide, aluminium hydroperoxide or boehmite, calcium and magnesium silicates, aluminosilicates including nanoclays, kaolin, montmorillonites including bentonites, hectorites and saponites, mica, talc including muscovites, phlogopites, lepidolites and chlorites, chalk, synthetic and precipitated silica, fumed silica, metal fibres and powders, zinc, aluminium, glass fibres, refractory fibres, carbon black including single- and multi-walled carbon nanotubes, reinforcing and non-reinforcing carbon black,
  • Other useful solid materials include flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, hexabromocyclododecane, ammonium polyphosphate, melamine, melamine cyanu- rate, antimony oxide and borates.
  • flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, hexabromocyclododecane, ammonium polyphosphate, melamine, melamine cyanu- rate, antimony oxide and borates.
  • the pigment comprises or consists of carbon black.
  • the dispersion of the present invention may be prepared by methods known and understood by those skilled in the art.
  • the dispersion used in the methods of the present invention comprises 0.5% to 40% by weight pigment, 0.5% to 40% by weight of the dispersant described herein, and 20% to 99% by weight solvent. Small amounts of other additives may be included in the dispersion as described herein and understood to those skilled in the art.
  • the solvent is primarily or solely ethylene glycol.
  • the solvent is primarily or solely oligomers of ethylene glycol having 2 to 5 repeat units of ethylene glycol.
  • the dispersant used in the methods of the present invention has a pH of greater than or equal to 5, or even greater than or equal to 7, when measured in a 50% solution of the dispersant in ethylene glycol.
  • the method of the present invention further includes the steps of adding to the dispersion a material having a boiling point higher than temperature (T), which is the boiling point of the solvent.
  • T temperature
  • the solvent comprises or consists of ethylene glycol or oligomers of ethylene glycol having 2 to 5 repeat units.
  • temperature T may be at least 180°C, or 190°C, or 195°C, or even at least 200°C.
  • Materials which have a boiling point higher than temperature T may include other solvents but may also include reactive monomeric components.
  • the materials having a boiling point higher than temperature (T) include monomers formed by the reaction product of a lower-aliphatic glycol with dimethyl terephthalate or the reaction product of a lower-aliphatic diol with terephthalic acid.
  • the materials having a boiling point higher than temperature (T) may also include bis(2-hydroxyethyl)terephthalate, 2- hydroxyethyl terephthalic acid, or mixtures thereof.
  • the mixture After mixing or while mixing the material having a boiling temperature higher than (T) with the dispersion described herein the mixture is heated to a temperature that is at least T or higher. In some embodiments, the mixture is heated to temperatures above 180°C, or 190°C, or 195°C, or 200°C, or even at least 250°C, for example, 200°C to 300°C, or even 250°C to 295°C.
  • the dispersant of the present invention unexpectedly provides a stable pigment dispersion at elevated temperatures.
  • the pigmented polymer prepared by the method of the present invention is polyethylene terephthalate (PET).
  • PET polyethylene terephthalate
  • monomers for preparation of PET polymer are formed by transesterification or esterification reactions.
  • the monomers are prepared by the transesterification or esterification reaction of dimethyl terephthalate and a lower-aliphatic diol (such as ethylene glycol or mono-ethylene glycol) or terephthalic acid and a lower aliphatic diol (such as ethylene glycol or mono-ethylene glycol).
  • the products of the transesterification or esterification reactions include bis-(2-hydroxy ethyl) terephthalate or 2-hy- droxyethyl terephthalic acid.
  • the dispersion described herein and the product of the transesterification or esterification reaction are mixed and then heated to temperatures of at least 180°C, or at least 190°C, or at least 195°C, or at least 200°C, or even at least 250°C, for example, 200°C to 300°C, or even 250°C to 295°C.
  • the polymer produced by the method of the present invention comprises from 0.01 to 20% based on the weight of the polymer, further for example 0.1 to 2% by weight, or even 0.4% to 1.6% by weight of the pigment.
  • the pigment comprises carbon black.
  • Intermediate 8 Aqueous polyacrylic acid (49.5% active) (Carbos- perseTM K-732) (250.00 parts) and polyethylene glycol monomethyl ether MW 1000 (230.20 parts are heated at 160 °C and water removed over 24.0 hours, yielding a clear amber viscous liquid.
  • Comparative example 2 Example 7 of patent WO2012125609A1
  • Comparative example 3 Morwet D-809 (Nouryon) Naphthalene sulfonic acid-formaldehyde condensate
  • Comparative example 4 Orotan SN (Dow) - Naphthalene sulfonic acid-formaldehyde condensate
  • the mill base (1.00 g) was then removed from the vial and charged to a 32 mL vial.
  • Ethylene glycol (6.75 g) was charged to the vial and the contents were then stirred until homogeneous to produce a dilute mill base.
  • the vial was heated to 200 °C. Once the dilute mill base had reached 200 °C it was examined to determine if it was homogeneous or not. With non-homogeneous materials having a much greater proportion of pigment at the bottom of the vial and with homogeneous being a pass.
  • Table 1 The results are summarized in Table 1.
  • Test 2 Addition of Material Having a Boiling Point Higher than Ethylene Glycol solvent (Bis-(2-hydroxyethyl) terephthalate (“BHET”)) at 200 °C: The material resulting from Test 1 was carried forward into Test 2. BHET (7.75 g) was charged to the vial at 200 °C. Once the BHET had melted the sample was stirred and heated for a further hour. This process was repeated a further two times, so that in total 23.25 g of BHET had been added in total and the sample had been heated for a total of 3 hours. The sample is allowed to cool to room temperature.
  • BHET Bis-(2-hydroxyethyl) terephthalate
  • the transitional term “comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open- ended and does not exclude additional, un-recited elements or method steps.
  • the term also encompass, as alternative narrower embodiments, the phrases “consisting essentially of’ and “consisting of,” where “consisting of’ excludes any element or step not specified and “consisting essentially of’ permits the inclusion of additional un-recited elements or steps that do not materially affect the basic and novel characteristics of the composition or method under consideration.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

L'invention concerne un procédé de formation d'une dispersion de pigment qui est stable à des températures élevées, la dispersion contenant un pigment, un solvant et un dispersant qui est un sel d'un polyacide à fonction polyéther.
PCT/US2021/062128 2020-12-18 2021-12-07 Composition de dispersion de pigment stable Ceased WO2022132491A1 (fr)

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CN116745386A (zh) 2023-09-12
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