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WO2025216845A1 - Formulations de peinture et de revêtement contenant du 3-amino-2-butanol et leurs utilisations - Google Patents

Formulations de peinture et de revêtement contenant du 3-amino-2-butanol et leurs utilisations

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Publication number
WO2025216845A1
WO2025216845A1 PCT/US2025/020120 US2025020120W WO2025216845A1 WO 2025216845 A1 WO2025216845 A1 WO 2025216845A1 US 2025020120 W US2025020120 W US 2025020120W WO 2025216845 A1 WO2025216845 A1 WO 2025216845A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
amino
butanol
additive
pigment
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.)
Pending
Application number
PCT/US2025/020120
Other languages
English (en)
Inventor
Romain Severac
Jordan Quinn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Advancion Corp
Original Assignee
Advancion Corp
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Filing date
Publication date
Application filed by Advancion Corp filed Critical Advancion Corp
Publication of WO2025216845A1 publication Critical patent/WO2025216845A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
    • C09D131/02—Homopolymers or copolymers of esters of monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • compositions also referred to herein as “formulations” that include 3-amino-2-butanol, including formulations of coatings, paints, and the like.
  • compositions and formulations comprising 3- amino-2-butanol (“3-AB”, also known as 3-amino-butan-2-ol; CAS No.: 42551-55-3), including compositions as well as formulations for paints and coatings.
  • 3 -Amino-2 -butanol has several advantages, including its improved sustainability profile, demonstrated by its ability to be manufactured as a renewable, biobased compound (z.e., without relying on nonrenewable petroleum-based raw materials) alongside its low toxicity (providing a safer alternative with reduced environmental and health impacts) while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NEb).
  • the presently disclosed technology overcomes common adoption barriers associated with renewable chemicals, such as poor performance and high cost, instead providing a high- performance, cost-effective solution with the potential for incorporating bio-based carbon.
  • the present technology provides a composition including about 30 wt.% to about 99.99 wt.% 3-amino-2-butanol and about 0.01 wt.% to about 70 wt.% water and optionally an amino alcohol other than 3-amino-2-butanol (an “other amino alcohol”).
  • the present technology is directed to compositions for paints and coatings comprising 3-amino-2-butanol.
  • the composition may be a dispersion or emulsion, such as an aqueous dispersion or emulsion.
  • the composition may include a dispersion of a pigment and/or an additive, wherein the additive comprises 3-amino-2-butanol.
  • the composition may include an aqueous dispersion of a pigment and/or an additive, wherein the additive comprises 3-amino- 2-butanol.
  • the composition may include a dispersion of a binder and an additive, wherein the additive comprises 3-amino-2-butanol.
  • the composition may include an aqueous dispersion of a polymeric binder resin and an additive, wherein the additive comprises 3-amino-2-butanol. In some embodiments, the composition may include about 0.01 wt.% to about 10 wt.% of the additive.
  • FIGS. 1 A-1C provide changes in color for the corresponding additives (amidoamine, N,N-dimethyl-tris(hydroxymethyl)aminomethane (“DMTA V2”), 3 -amino-2 -butanol (“3AB”; of the present technology), tri s(hydroxymethyl)aminom ethane (“TA40 Crystals”), 2- dimethylamino-2-m ethylpropanol (“DMAMP80”), 2-amino-2-methyl-l -propanol (“AMP”),
  • DMTA V2 N,N-dimethyl-tris(hydroxymethyl)aminomethane
  • 3AB 3 -amino-2 -butanol
  • TA40 Crystals tri s(hydroxymethyl)aminom ethane
  • DMAMP80 2- dimethylamino-2-m ethylpropanol
  • AMP 2-amino-2-methyl-l -propanol
  • Iso-DMAMP 1,3 -propanediol
  • DEAAMP 2,2'-((2-amino-2- methylpropyl)azanediyl)bis(ethan-l-ol)
  • TA40 diethanolamine
  • DEA 2-((dimethylamino)methyl)butane-l,2-diol
  • Iso- DMAEPD 2-((3-aminopropyl)(butyl)amino)ethan-l- ol
  • APIBAE 2-amino-2-ethyl- 1,3 -propanediol
  • AEPD VOX 1000 2-amino-2-ethyl- 1,3 -propanediol
  • TAA triethylamine
  • 3 AB provides a coordinate value consistently close to 0 (Aa ⁇ l)over the time period (as compared to Aa >4 for amidoamine).
  • 3 AB provides a b coordinate consistently close to 0 (Ab ⁇ 2) over the time period (as compared to Ab >70 for amidoamine, Ab >50 for DMTA V2, Ab >8 for TA40, Ab >8 for Iso-DMAEPD, Ab >7 for VantexT).
  • FIG. 2 provides the dispersant demand curves of TiCh (KRONOS 2190, from Kronos) with 0.05 wt.% of the corresponding additives (2-amino-2-methyl-l -propanol (“AMP”), 3 -amino-2 -butanol (“3AB”; of the present technology)), diethanolamine (“DEA”), or triethylamine (“TEA”)), or 25 wt.% NaOH solution, and in the presence of a polymeric dispersant (ORO TANTM 731A ER, from Dow). As shown in FIG.
  • 2, 3 AB and AMP require the least amount of polymeric dispersing agent, namely OROTANTM 731 A ER, (0.28 wt.% of dispersant per pigment weight) to achieve the lower Krebs viscosity (compared to 0.38 wt.% for DEA, 0.56 wt.% for TEA, and 0.60 wt.% for NaOH).
  • An optimum (or minimum) concentration of polymeric dispersing agents reduces the hydrophilicity of the dry film leading to an improvement of several parameters such as: water resistance, chemical resistance, stain resistance, washability of the surface, lower microfoaming effect, and/or syneresis formation during storage.
  • alkyl refers to a group, whether alone or as part of another group e.g., in dialkylamino), encompasses straight and branched chain aliphatic groups (ie., saturated hydrocarbyl chains), and, unless otherwise indicated, has 1-10, alternatively 1-8, or alternatively 1-6 alkyl carbon atoms.
  • alkyl groups include, without limitation, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl. Unless otherwise indicated, the alkyl group is optionally substituted with 1, 2, or 3, e.g., 1 or 2, or even just 1, substituent(s) that are compatible with the compounds, monomers, and polymers described herein. In some embodiments, the alkyl group is unsubstituted.
  • alkoxy refers to a group in which an oxygen attached to a saturated straight or branched chain alkyl group. Unless otherwise indicated, the alkoxy group contains 1 to 6 carbon atoms (e.g. methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or isohexyloxy), and in any embodiments, 1 to 4 carbon atoms.
  • 1 to 6 carbon atoms e.g. methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, neopentyloxy, iso-pentyloxy, n-hexyloxy or isohexyloxy
  • the alkoxy groups include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy and tert-butoxy. In some embodiments, the alkoxy group is unsubstituted.
  • substituted refers to an alkyl group, as defined above in which one or more bonds to a hydrogen atom contained therein are replaced by a bond to non-hydrogen or non-carbon atoms.
  • Substituted groups also include groups in which one or more bonds to a carbon(s) or hydrogen(s) atom are replaced by one or more bonds, including double or triple bonds, to a heteroatom.
  • a substituted group is substituted with 1, 2, or 3 substituents. Examples of substituent groups include, but are not limited to, hydroxyl, amino, thiol, nitro, halo, ester, amido, carbonyl, or carboxylic acid.
  • binder refers to the film forming component of a coating.
  • a polymeric binder z.e., polymer
  • Coalescence refers to the process where first the solvent (e.g., water) evaporates causing the polymeric binders to be drawn together and then fused into irreversibly bound networked structures, so that the coating cannot redissolve in the original carrier solvent.
  • Polymeric binder resin is a type of “binder.”
  • water-reducible polymeric binder refers to a hydrophobic resin that has been modified to contain acidic groups such that the binder is soluble in water with at least partial neutralization.
  • water- dispersible polymeric binder z.e., water-dispersible binder
  • resins with acidic groups that could be dispersed in a continuous aqueous medium with at least partial neutralization.
  • substantially free refers to less than about 2 wrl.% of the specified component based on the total weight of the composition.
  • the composition may include less than about 1 wt.%, less than about 0.5 wt.%, or less than about 0.1 wt.% of the specified component.
  • the composition may free of detectable amounts of the component.
  • compositions Comprising 3-Amino-2-Butanol (“3-AB”)
  • the present technology provides a composition including about 30 wt.% to about 99.99 wt.% 3-amino-2-butanol, about 0.01 wt.% to about 70 wt.% water, and optionally an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”).
  • the compositions may include 3-amino-2-butanol in an amount of about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, about 50 wt.%, about 55 wt.%, about 60 wt.%, about 65 wt.%, about 70 wt.%, about 75 wt.%, about 80 wt.%, about 85 wt.%, about 90 wt.%, about 95 wt.%, about 96 wt.%, about 97 wt.%, about 98 wt.%, about 99 wt.%, about 99.5 wt.%, about 99.9 wt.%, about 99.95 wt.%, about 99.99 wt.%, or any range including and/or in-between any two of these values.
  • the composition may include 85 wt.% to 95 wt.% 3-amino-2-butanol. In any embodiments, the compositions may include at least about 90 wt.% 3 -amino-2 -butanol.
  • the compositions may include 0.01 wt.% to about 70 wt.% water. Such compositions may be solutions at room temperature, e.g., a homogenous solution. In any embodiments, the compositions may include about 0.01 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, about 11 wt.%, about 12 wt.%, about 13 wt.%, about 14 wt.%, about 15 wt.%, about 16 wt.%, about 17 wt.%, about 18 wt.%, about 19 wt.%, about 20 wt
  • the compositions may include 5 wt.% to 15 wt.% water or about 10 wt.% water.
  • the water may be tap water, deionized water, distilled water, reverse osmosis (R.O.) water, or any combination thereof, including, e.g., double distilled water.
  • R.O. reverse osmosis
  • the purity and water content may be adjusted depending on the desired physical properties and end-use application.
  • water and/or an other amino alcohol may be included in the compositions including 3 -amino-2 -butanol, e.g., to improve handling and/or modify performance characteristics.
  • addition of water to the compositions including 3- amino-2-butanol may increase the flash point, reduce the freezing point, and/or reduce the viscosity of the composition.
  • Exemplary other amino alcohols that may be included in compositions of any embodiment herein include, but are not limited to, 3-amino-3-methyl-2- butanol, 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-m ethyl- 1- propanol, 2-amino-l -butanol, 2-amino-2-ethyl- 1,3 -propanediol, 3-(ethylamino)-3- methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
  • composition of any embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-m ethyl- 1 -propanol, 2- amino-1 -butanol, 2-amino-2-ethyl-l,3-propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3- (ethylamino)-butan-2-ol, or a combination of any two or more thereof) in amount of not more than about 0.01 wt.%, not more than about 0.02 wt.%, not more than about 0.03 wt.%, not more than about 0.04 wt.%, not more than about 0.05 wt.%, not more than about 0.06 wt.%, not more than about 0.07 wt.%, not more than about 0.08 wt.%
  • the composition may include less than about 2 wt.% secondary amine (e.g., 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 2- (butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as l-(2- hydroxypropylamino)propan-2-ol), and/or dicycohexylamine).
  • secondary amine e.g., 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, 2- (butylamino)ethanol, diethanolamine, diisopropanolamine (also referred to as l-(2- hydroxypropylamino)propan-2-ol), and/or dicycohexylamine).
  • the composition may include an amount of secondary amine that is less than about 2 wt.%, less than about 1.5 wt.%, less than about 1 wt.%, less than about 0.5 wt.% secondary amine, or any range including and/or in-between any two of these values.
  • the composition may include less than about 0.5 wt.% secondary amine.
  • the composition may exhibit a biobased content of the 3- amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866- 24 of 0% to 100%.
  • biobased content of the 3-amino-2-butanol in compositions of the present technology may be provided by using purely petroleum-based 3 -amino-2 -butanol (z.e., with 0% biobased content), using 3 -amino-2 -butanol produced in part with biobased starting materials, using combinations of purely petroleum-based 3-amino- 2 -butanol and 3 -amino-2 -butanol produced in part or in whole with biobased starting materials, or — for a biobased content of the 3-amino-2-butanol of 100% — using 3-amino-2- butanol produced in whole with biobased starting materials.
  • the composition may exhibit a biobased content of the 3-amino-2-butanol (as determined using radiocarbon analysis in accordance with ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or any range including and/or in-between any two of these values.
  • a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24
  • composition of any embodiment herein may exhibit a biobased content of the 3 -amino-2 -butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%.
  • a composition of any aspect and/or embodiment herein may include a renewable, biobased compound (z.e., 3-amino-2-butanol) that exhibits low toxicity while concurrently providing comparable or superior performance as compared to petroleum based alternatives and superior performance as compared to current renewable alternatives (e.g., NEb).
  • the present technology provides methods of making any of the disclosed compositions.
  • the methods include combining 3-amino-2-butanol with a purity of at least 95 wt.% with sufficient water to provide the stated composition, e.g., as a solution.
  • the methods may further include mixing the combined 3 -amino-2 -butanol and water until a homogenous solution is obtained.
  • Racemic 3-amino-2-butanol may be separated into (R)-3 -amino-2 -butanol and CS')-3- amino-2-butanol by methods known in the art, including chiral chromatography or diastereomeric salt recrystallization.
  • Diastereomeric salt recrystallization involves neutralizing a chiral amino alcohol using an optically active acid. The resulting diastereomers are separated by crystallization and neutralized to recover the optically enriched amino alcohol. The crystallization process may be repeated to achieve optical purity of 99% or higher.
  • compositions Comprising 3-Amino-2-Butanol for Paints and Coatings
  • the present technology provides compositions (e.g., paints, coatings, etc.) comprising 3-amino-2-butanol.
  • the composition may be a coating (e.g., paint), such as an aqueous based coating.
  • the composition may include a dispersion of a pigment and/or an additive, wherein the additive comprises 3-amino-2-butanol.
  • the composition may include an aqueous dispersion of a pigment and/or an additive, wherein the additive comprises 3 -amino-2 -butanol.
  • the composition may include a dispersion of a binder and an additive, wherein the additive comprises 3-amino-2-butanol.
  • the composition may include an aqueous dispersion of a polymeric binder resin and an additive, wherein the additive comprises 3 -amino-2 -butanol.
  • compositions of the present technology may include a wide range of amounts of the additive described herein (z.e., 3 -amino-2 -butanol).
  • the compositions may include about 0.005 wt.% to about 15 wt.% of 3 -amino-2 -butanol based on the total weight of the composition, e.g., about 0.05 wt.% to about 5 wt.%, about 0.05 wt.% to about 2 wt.%, about 0.05 wt.% to about 0.5 wt.%, or about 0.05 wt.% to about 0.3 wt.%.
  • compositions may include 3-amino-2-butanol in an amount of about 0.005 wt.%, about 0.01 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.15 wt.%, about 0.2 wt.%, about 0.3 wt.%, about 0.4 wt.%, about 0.5 wt.%, about 0.75 wt.%, about 1 wt.%, about 1.5 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, about 11 wt.%, about 12 wt.%, about 13 wt.%, about 14 wt.%, about 15 wt.%, or any range including and/or in-between any two of these values
  • compositions of the present technology may or may not include water.
  • the water may be used as a solvent and/or as a thinner when preparing and/or applying the coating composition.
  • the compositions may include at least about 20 wt.% water, at least about 25 wt.% water, at least about 30 wt.% water, at least about 35 wt.% water, at least about 40 wt.% water, at least about 45 wt.% water, at least about 50 wt.% water, at least about 55 wt.% water, at least about 60 wt.% water, or any range including and/or in-between any two of these values.
  • the compositions may include about 20 wt.% to about 99 wt.% water, about 35 wt.% to about 97 wt.%, about 45 wt.% to about 95 wt.%, about 50 wt.% to about 95 wt.%, or any range including and/or inbetween any two of these values. In some embodiments, the compositions may include about 20 wt.% to about 80 wt.% water.
  • the composition may further include an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”), where exemplary other amino alcohols that may be included in a composition according to any embodiment herein include, but are not limited to, 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1- amino-2-propanol, 2-amino-2-m ethyl- 1 -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof.
  • an amino alcohol other than 3 -amino-2 -butanol an “other amino alcohol”
  • exemplary other amino alcohols that may be included in a composition according to any embodiment herein include, but are not limited to, 3-amin
  • composition of any embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, l-amino-2-propanol, 2-amino-2-methyl-l -propanol, 2-amino-l -butanol, 2- amino-2-ethyl- 1,3 -propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2- ol, or a combination of any two or more thereof) in amount of at least about 0.01 wt.%, at least about 0.02 wt.%, at least about 0.03 wt.%, at least about 0.04 wt.%, at least about 0.05 wt.%, at least about 0.06 wt.%, at least about 0.07 wt.%, at least about 0.08 wt.%, at least about 0.09 wt.%
  • composition of any embodiment herein may include an other amino alcohol (e.g., 3-amino-3-methyl-2-butanol, 2-aminoethanol, triethanolamine, 1 -amino-2 - propanol, 2-amino-2-methyl-l -propanol, 2-amino-l -butanol, 2-amino-2-ethyl-l,3- propanediol, 3-(ethylamino)-3-methylbutan-2-ol, 3-(ethylamino)-butan-2-ol, or a combination of any two or more thereof) in amount of not more than about 0.01 wt.%, not more than about 0.02 wt.%, not more than about 0.03 wt.%, not more than about 0.04 wt.%, not more than about 0.05 wt.%, not more than about 0.06 wt.%, not more than about 0.07 wt.%, not more than about 0.08 wt.%, not more
  • the composition may exhibit a biobased content of the 3 -amino-2 -butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of 0% to 100% — thus, in any embodiment herein, the composition may exhibit a biobased content of the 3 -amino-2 -butanol (as determined using radiocarbon analysis in accordance with ASTM D6866-24) of 0%, at least about 1%, at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 45%, at least about 50%, at least about 55%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, about 100%, or any range including and/or in-between any two of these values.
  • composition of any embodiment herein may exhibit a biobased content of the 3-amino-2-butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 10%, or may exhibit a biobased content of the 3 -amino-2 -butanol as determined using radiocarbon analysis in accordance with ASTM D6866-24 of at least about 25%.
  • Binders
  • a composition as described herein (e.g., a paint or a coating) comprises a binder (e.g., a polymeric binder resin and/or an inorganic binder).
  • the polymeric binder resin may be a water-reducible polymeric binder, a water-dispersible polymer, or an emulsion polymer.
  • Binders include polymers e.g., polymeric binder resins) such as a polyacrylate, polyvinyl versatate, poly ethylene-vinyl acetate, polyester e.g., polyester polyols and polyester polymers with one or more olefins), or a combination of two or more thereof as well as inorganic binders such as lithium silicate and/or potassium silicate and/or a combination of silicon dioxide with lithium silicate and/or potassium silicate.
  • the polyacrylate may be a homopolymer or a copolymer.
  • Monomers that may be used for such polymers include but are not limited to acrylic acid and methacrylic acid (i.e., (meth)acrylic acid), butyl (meth)acrylate, hydroxyethyl (meth)acrylate, isopropyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, and diethylaminoethyl (meth)acrylate. Additionally, monomers such as vinyl silane, vinyl acetate and styrene may be used in such polymers. Exemplary copolymers of polyacrylate include polyvinyl acrylate, polyvinyl versatate- acrylate, polystyrenyl acrylate, or a combination of two or more thereof.
  • the binder may be a latex binder. In some embodiments, the binder may be an alkyd binder. In some embodiments, the composition may be an invert emulsion where the composition comprises an alkyd binder.
  • the binders provided herein may be used individually in the compositions, may be used in combination as a simple blend, or may be used as a hybrid type copolymer.
  • Examples of commercially available polymeric binder resins that may be used include EVOQUETM 1133, EVOQUETM 1180, EVOQUETM 3150, RHOPLEXTM 585, RHOPLEXTM 800h, RHOPLEXTM AC-264, RHOPLEXTM 464, RHOPLEXTM 26 ILF, RHOPLEXTM AC- 337N, RHOPLEXTM AC-347, RHOPLEXTM AC-2235M, RHOPLEXTM 2438C, RHOPLEXTM 2500, RHOPLEXTM 2508, RHOPLEXTM EC-3814, RHOPLEXTM EZ CLEANTM 1500, RHOPLEXTM HG-95P, RHOPLEXTM HG-98B, RHOPLEXTM HG-706, RHOPLEXTM ML-200, RHOPLEXTM ML-400, RHOPLEXTM MV-23LO, RHOPLEXTM PR- 33, RHOPLEXTM PR-409, RHOPLEXTM SG-10AF, RHOPLEXTM
  • RO V ACETM 10 RO V ACETM 9100AF, RO V ACETM 9900, JSPJ-100, JSPJ-200, JSPJ-300, and JSPJ-400.
  • the amount of the binder in the formulations of the present technology can be those conventionally used in paint and coating formulations, which can vary widely due to the desired gloss/sheen range, and also the solids concentration, of a specific paint formulation.
  • the compositions of the present technology may include from about 10 wt.% to about 80 wt.% binder (e.g., polymeric binder resin and/or inorganic binder) based on the total weight of the composition, including from about 15 wt.% to about 65 wt.%, or from about 40 wt.% to about 60 wt.%.
  • the composition may include about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, about 50 wt.%, about 55 wt.%, about 60 wt.%, about 65 wt.%, about 70 wt.%, about 75 wt.%, or about 80 wt.%, of the binder, or any range including and/or in-between any two of these values.
  • the composition includes from about 20 wt.% to about 60 wt.% binder based on the total weight of the composition.
  • the polymeric binder resins used herein include acid functional groups such as carboxyl, sulfonyl, phosphonyl, and/or phosphoric acid groups.
  • the acid functional groups are carboxyl groups.
  • the polymeric binders may have acid values of about 2 to about 200 mg KOH/g. In some embodiments, the polymeric binders may have acid values of about 5 to about 150 mg KOH/g or about 10 to about 100 mg KOH/g.
  • the additive may neutralize at least about 20% of the acid functional groups on the polymeric binder resin (e.g., at least about 30%, at least about 40%, or at least about 50%). In some embodiments, the additive neutralizes about 20% to about 100% of the acid functional groups on the polymeric binder (e.g., about 30% to about 90% or about 40% to about 80%). In some embodiments, the molar ratio of the additive to the acid functional groups on the polymeric binder may be about 1 :5 to about 5: 1 (e.g., about 1 :4 to about 2: 1, about 1 :3 to about 2: 1, or about 1 :2 to about 1 : 1).
  • the binders of the present technology may be prepared by way of a wide range of processes.
  • the binders may be prepared in organic phase or in melt and then converted into water, the polymeric binder resin could also be prepared by emulsion polymerizations, or any other method known to those of skill in the art.
  • a composition as described herein (e.g., a paint or a coating) comprises a pigment. Pigments may be included to provide hiding power and the desired color to the final coated material and/or may be used to provide bulk to the paint or coating, and/or to provide anticorrosive properties (e.g., zinc phosphate). All color and/or special effect-giving pigments of organic or inorganic type used in paints and coatings are suitable for use.
  • a composition as described herein comprises a pigment selected from the group consisting of titanium dioxide (TiCh), calcium carbonate, silica (SiCh), kaolin, and barium sulfate.
  • a composition as described herein comprises titanium dioxide and a colorant.
  • Colorants include dyes, pigments, and pre-dispersions, among others. Colorants are pigments that provide color. Colorants include red, white, blue, black, and yellow. As used herein, “pigment” refers to finely ground, insoluble material suspended in a medium, which changes the color of reflected or transmitted light through wavelength- selective absorption. Pigments typically possess high tinting strength properties and are stable in solid form at ambient temperatures. Pigments can be natural or synthetic products. While multiple pigments may be present in end-use paints or coatings, it is also possible to use only white pigment, such as titanium oxide, perhaps in combination with extender pigments. Any other desired pigments of various colors (including more white pigment) can optionally be included in the compositions.
  • pigments may be provided in the form of raw pigments, treated pigments, pre-milled pigments, pigment powders, pigment presscakes, pigment masterbatches, recycled pigment, and solid or liquid pigment predispersions.
  • a raw pigment is a pigment particle that has had no wet treatments applied to its surface, such as to deposit various coatings on the surface. Raw pigment and treated pigment are further discussed in PCT Publication No. WO 2005/095277 and U.S.
  • a treated pigment may have undergone wet treatment, such as to provide metal oxide coatings on the particle surfaces.
  • metal oxide coatings include alumina, silica, and zirconia.
  • Recycled pigment may also be used as the starting pigment particles, where recycled pigment is pigment after wet treatment of insufficient quality to be sold as coated pigment.
  • Exemplary colorant particles include, but are not limited to, pigments such as yellow coloring agent, compounds typified by a condensed azo compound, an isoindolynone compound, an anthraquinone compound, an azometal complex methine compound, and an allylamide compound as pigments may be used.
  • magenta coloring agent a condensed azo compound, a diketopyrrolopyrrole compound, anthraquinone, a quinacridone compound, a base dye lake compound, a naphthol compound, a benzimidazolone compound, a thioindigo compound, and a perylene compound may be used.
  • a cyan coloring agent a copper phthalocyanine compound and its derivative, an anthraquinone compound, a base dye lake compound, and the like may be used.
  • pigments can include, but are not limited to, titanium dioxide, kaolin clay, calcined kaolin clay, carbon black, iron oxide black, iron oxide yellow, iron oxide red, iron oxide brown, organic red pigments, including quinacridone red and metallized and non-metallized azo reds (e.g., lithols, lithol rubine, toluidine red, naphthol red), phthalocyanine blue, phthalocyanine green, mono- or di-arylide yellow, benzimidazolone yellow, heterocyclic yellow, quinacridone magenta, quinacridone violet, and the like, and any combination thereof.
  • quinacridone red metallized and non-metallized azo reds
  • the pigment is selected from the group consisting of titanium dioxide, clay, silica, diatomaceous silica, calcium carbonate, talc, zinc oxide, mica, red oxide, hansa yellow, phthalo blue, and yellow ochre.
  • the pigment may be a special effect pigment.
  • special effect pigments are metal pigments, for example, from aluminum or copper, interference pigments, such as, for example, aluminum coated with titanium dioxide, coated mica, graphite effect pigments and iron oxide laminae.
  • Some special effect pigment may be inhibitor and/or extender pigments.
  • Inhibitors, such as rust inhibitors are pigments that have little to no corrosive action.
  • metal pigments are commonly used to protect metallic surfaces from corrosion.
  • Nonlimiting exemplary inhibitor pigments include zinc, chromate, phosphate, and borate based pigments. Extender pigments are typically added to paints and coatings to reduce the cost of formulations.
  • extender pigments appear white and possess a refractive index similar to commonly used binders.
  • Nonlimiting exemplary extender pigments include clay, silica, and mica.
  • the compositions of the present technology may include from 0 wt.% or from about 5 wt.% to about 75 wt.% pigment based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 40 wt.%, about 50 wt.%, about 60 wt.%, about 75 wt.% of pigment, or any range including and/or inbetween any two of these values.
  • the compositions may include from about 10 wt.% to about 75 wt.%, or from about 55 wt.% to about 75 wt.% pigment based on the total weight of the composition.
  • compositions described herein e.g., the paint or coating compositions
  • an additive e.g., 3-amino-2-butanol
  • a binder e.g., a polystyrene
  • a pigment e.g., polystyrene
  • water e.
  • the carrier is the solvent in which composition materials are dissolved, dispersed, and/or suspended.
  • the carrier is water, although other water-based solutions such as water-alcohol mixtures and the like may be used.
  • the aqueous carrier generally makes up the balance of the composition, after all the other ingredients have been accounted for.
  • the composition may include a cosolvent such as an organic solvent.
  • the cosolvent may be an alcohol (e.g., methanol, ethanol, or isopropyl alcohol), glycol ether such as ethylene glycol, diethylene glycol, and/or propylene glycol (e.g., propylene glycol C1-C4 alkyl ether, C1-C4 alkoxyethanol such as butoxyethanol), a heterocycle such as a lactone or a lactam (e.g., N- methyl-2-pyrrolidone), glycerin, or a combination thereof.
  • Cosolvents are sometimes present in the composition to aid in film formation, to resist freezing, and/or enhance brushing properties, such as by increasing open time.
  • Open time is the time that a coating remains workable after it has been applied to a substrate. Open time allows for rebrushing or "melting in” of the newly applied coating at the lap, without causing brush marks, loss of gloss, or lap lines in the final dried coating.
  • a lap is an area on a substrate where additional coating is applied onto a portion of a previously coated, but still wet, adjacent substrate area.
  • the compositions may include no more than about 15 wt.% cosolvent (e.g., 1- 15 wt.%), based on total composition. Alternatively, the compositions may include no more than about 10 wt.% cosolvent or no more than about 5 wt.% cosolvent (e.g., 1-10 or 1-5 wt.%).
  • a composition as described herein may comprise one or more other ingredients.
  • the composition may further include a dispersing agent.
  • the dispersing agent may be present at an effective amount, e.g., about 0.01 wt.% to about 10 wt.% of the composition.
  • the amount of dispersing agent in the composition may be about 0.01 wt.%, about 0.02 wt.%, about 0.05 wt.%, about 0.075 wt.%, about 0.1 wt.%, about 0.2 wt.%, about 0.3 wt.%, about 0.4 wt.%, about 0.5 wt.%, about 0.6 wt.%, about 0.7 wt.%, about 0.8 wt.%, about 0.9 wt.%, about 1 wt.%, about 1.5 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, or any range including and/or in-between any two of these values.
  • Dispersing agents are soluble materials whose physicochemical ad
  • Illustrative dispersing agents include, but are not limited to, salts of polyacrylic acids or modified polyacrylic acids, and polyphosphate salts such as sodium hexametaphosphate.
  • compositions including, but not limited to, coalescents, leveling agents and surfactants, thickeners (e.g., cross-linked poly carboxylic acid or polyurethanes), rheology modifiers (e.g., highly disperse silicic acid or polymeric urea compounds), corrosion inhibitors, defoamers, wetting agents, dispersants, biocides, flow control agents based on (meth)acrylic homopolymers or silicon oils, or combinations of two or more thereof.
  • Such ingredients may provide specific properties to the composition and/or the film, such as mildew resistance, defoaming, light stability, and/or good flow and leveling during application.
  • compositions may include one or more ingredients selected from the group consisting of leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional neutralizer(s), dyes, fragrances, and biocides.
  • ingredients selected from the group consisting of leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional neutralizer(s), dyes, fragrances, and biocides.
  • leveling agents such as leveling of leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional neutralizer(s), dyes, fragrances, and biocides.
  • compositions of the present technology may include from about 0 wt.% to about 75 wt.% one or more ingredients selected from the group consisting of leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional neutralizer(s), and biocides, based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 40 wt.%, about 50 wt.%, about 60 wt.%, about 75 wt.%, or any range including and/or in-between any two of these amounts of one or more ingredients selected from the group consisting of leveling agents, surfactants, thickeners, rheology modifiers, co-solvents, corrosion inhibitors, defoamers, co-dispersants, additional neutralize ⁇ s), and biocides.
  • Leveling agents may be added to change the surface tension and improve wetting.
  • Leveling agents are a subset of surfactants used to ensure that a composition flows out over and completely wets the surface being coated. Reduced contact angles between the composition and the surface lead to better flow leveling, and better surface wetting allows for better adhesion of the composition and the physically coalesced and/or chemically cured film.
  • Surfactants are also important as grinding aids for pigment grinding operations.
  • the compositions of the present technology may include from about 0 wt.% to about 7 wt.% surfactants (e.g., leveling agents) based on the total weight of the composition.
  • the compositions of the present technology may include from about 0 wt.% to about 7 wt.% surfactants (e.g., leveling agents) based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, of thickeners, or any range including and/or in-between any two of these values.
  • Rheology modifiers may be added to thicken the compositions and to increase its yield stress, thus allowing for the formation of a stable suspension of pigments in resin upon mixing. Rheology modifiers are also added to optimize the application properties of the composition.
  • the compositions of the present technology may include from about 0 wt.% to about 7 wt.% rheology modifiers based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.% of rheology modifiers, or any range including and/or in-between any two of these values.
  • Pigment dispersants are added to create a stable dispersion of the pigment. Pigment dispersants function by directly interacting with pigment particles both mechanically and electrostatically. Rheology modifiers function by increasing the yield stress of the waterresin system.
  • the compositions may include 0 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 8 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.% of corrosion inhibitors and/or flash rust inhibitors, or any range including and/or in-between any two of these values.
  • Biocides including registered biocides
  • mildewcides may be added to control microbial growth in the compositions and/or in the film. Microbes can colonize leading to filamentous growths, bad odors and the selective consumption of functional coating ingredients.
  • Some biocides can be added solely to control microbes during storage of the composition (so called in-can biocides) while other biocides are added to impart biostability to the coalesced/cured film (so called dry film biocides).
  • Some biocides can prevent both incan and dry film biological growth.
  • the compositions of the present technology may include from about 0 wt.% to about 2 wt.% biocides or mildewcides based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 0.001 wt.%, about 0.005 wt.%, about 0.01 wt.%, about 0.05 wt.%, about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 1.5 wt.%, about 2 wt.% of biocides (including registered biocides) or mildewcides, or any range including and/or in-between any two of these values.
  • Defoamers are special types of surfactants that have the effect of decreasing the foaminess of an agitated coating compositions, when it is manufactured, when it is shaken or stirred, and when it is applied to a surface. Defoamers are commercially available under a number of tradenames such as, for example, FOAMASTER®, ADVANTAGE® 1512, and BYK® 1650. In some embodiments, the compositions of the present technology may include from about 0 wt.% to about 6 wt.% defoamers based on the total weight of the composition.
  • the compositions may include 0 wt.%, about 0.001 wt.%, about 0.01 wt.%, about 0.1 wt.%, about 0.5 wt.%, about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.% of defoamers, or any range including and/or in-between any two of these values.
  • the present compositions may include fillers.
  • fillers are silicon dioxide, barium sulfate, talcum, calcium carbonate, aluminum silicate and magnesium silicate.
  • the compositions of the present technology may include from about 0 wt.% to about 15 wt.% fillers based on the total weight of the composition.
  • the compositions may include 0 wt.% or any of about 0.1, 0.25, 0.5, 0.75, 1, 2, 3, 4, 5, 10 wt.%, or 15 wt.% of fillers, or any range including and/or in-between any two of these values.
  • the composition may be substantially free of low molecular weight surfactants. In some embodiments, the composition does not contain low molecular weight surfactants.
  • a method comprising adding to a composition (the composition including an aqueous dispersion, the aqueous dispersion including a pigment and/or a binder) an effective amount of the additive described herein (z.e., 3-amino-2-butanol) to raise the pH of the composition, stabilize the dispersion of the pigment in the composition, and/or at least partially neutralize any acidic compounds in the composition.
  • a composition the composition including an aqueous dispersion, the aqueous dispersion including a pigment and/or a binder
  • an effective amount of the additive described herein z.e., 3-amino-2-butanol
  • the pH of the composition may be raised to about 7 to about 13 or about 7 to about 10.
  • the pH when a biocide is included/to be included in the composition, the pH may be raised to about 8.5 to about 9.0 when a biocide is included/to be included in the composition; for example, when an inorganic binder is included/to be included in the composition, the pH may be raised to about 10.5 to about 11.5.
  • the composition is stable for at least about 1 month, at least about 2 months, at least about 3 months, at least about 6 months, at least about 12 months, or at least about 24 months.
  • the additive neutralizes at least about 20% of the acid functional groups on the polymeric binder (e.g., at least about 30%, at least about 40%, or at least about 50%). In some embodiments, the additive neutralizes about 20% to about 100% of the acid functional groups on the polymeric binder (e.g., about 30% to about 90% or about 40% to about 80%.
  • compositions described herein may be film forming compositions.
  • the films derived from the compositions may have any thickness; for example, such films may have a thickness in the range of from 0.1 micrometer (“pm”) to 10 millimeters (“mm”); or in the alternative, from 1 pm to 1000 pm; or in the alternative, from 5 pm to 500 pm; or in the alternative, from 10 to 100 pm; or in the alternative, from 10 pm to 80 pm; or in the alternative, from 10 to 50 pm.
  • the composition described herein is a coating.
  • the composition described herein is a latex paint. Accordingly, the present technology provides a coating comprising the dried composition (e.g., a dried layer or coating on a substrate) according to any one of the embodiments described herein.
  • the paints and/or coatings provided herein can be used for example, in different coating applications such as residential and/or industrial coating applications, architectural coating applications, automotive coating applications, outdoor furniture coating applications, exteriors and interiors of houses, and other buildings.
  • compositions as described herein may be applied by means of conventional application methods, for example, by rolling, brushing, dipping, or spraying onto any desired uncoated or pre-coated substrate.
  • the surface of such structures to be coated with the compositions may comprise concrete, wood, metal, plastic, glass, drywall, or the like.
  • drying/coalescing may then proceed at ambient temperature or elevated temperatures (e.g., about 25 °C to about 300 °C including about 50 °C to about 180 °C) depending on the composition.
  • the present technology provides a coating that includes the physically coalesced composition.
  • the composition may be physically coalesced at temperatures ranging from about 0 °C to about 300 °C.
  • the composition may be physically coalesced at temperatures of at least about 5 °C. In some embodiments, the temperatures may be at least about 10 °C. In some embodiments, the temperatures may be at least about 15 °C.
  • the composition may be physically coalesced at about room temperature. In some embodiments, the composition may be physically coalesced after about 60 minutes, after about 5 hours, after about 10 hours, after about 15 hours, or after about 1 day. For example, the composition may be physically coalesced after about 60 minutes to about 1 week, about 5 hours to about 12 days, about 10 hours to about 10 days, or about 1 day to about 7 days.
  • compositions described herein may be manufactured by conventional paint and coating manufacturing techniques, which are well known to those skilled in the art.
  • the compositions are manufactured by a two-step process.
  • a dispersion phase commonly referred to as the grind phase
  • This part of the process is designed to effectively wet and dis-agglomerate the dry pigments to a finely dispersed state.
  • the second step of the paint/coating manufacturing process is commonly referred to as the letdown or thindown phase, because the viscous grind is diluted with the remaining formulation components, which are generally less viscous than the grind mix.
  • the binder, any predispersed pigments, and any other paint/coating ingredients that only require mixing and perhaps moderate shear are incorporated during the letdown phase.
  • the letdown phase may be done either by sequentially adding the letdown components into a vessel containing the grind mix, or by adding the grind mix into a vessel containing a premix of the binder and other letdown components, followed by sequential addition of the final letdown components. In either case, constant agitation is needed, although application of high shear is not required.
  • the grinding step may be excluded.
  • the additive e.g., 3 -amino-2 -butanol
  • the additive may be added to the composition at one or more of three different places in the manufacturing process: to the pigment dispersion (grinding), to the binder dispersion (letdown), and/or in a final addition to the composition.
  • the additive e.g., 3 -amino-2 -butanol
  • the present technology contemplates a process for preparing a coating layer, which includes:
  • the applied coating layer may be flashed off to remove water and organic solvent, if present.
  • numeric ranges for instance as in “from 2 to 10,” are inclusive of the numbers defining the range (e.g., 2 and 10).
  • reaction mixture was then fed into a stainless-steel reactor containing Raney Nickel (10 wt.%) and methanol with 650 psi hydrogen at 45-65 °C. Upon complete reaction, the mixture was separated from the catalyst and distilled at ambient pressure. The fraction containing the desired product was collected at 159 °C and recovered as a colorless liquid.
  • the isolated yield was 70 % and the purity was 99 % according to GC-FID analysis (capillary column: 30 m fused silica, (5%-phenyl)-methylpolysiloxane bonded-phase column with a 0.25 mm inner diameter and 1.0 pm film thickness; carrier gas flow rate: 1 mL/min helium; gas chromatograph: Agilent model 7890, Series II).
  • FIGS. 1 A-1C provide changes in color for the corresponding additives (amidoamine, N,N-dimethyl-tris(hydroxymethyl)aminomethane (“DMTA V2”), 3 -amino-2 -butanol (“3AB”; of the present technology), tri s(hydroxymethyl)aminom ethane (“TA40 Crystals”), 2- dimethylamino-2-m ethylpropanol (“DMAMP80”), 2-amino-2-methyl-l -propanol (“AMP”),
  • DMTA V2 N,N-dimethyl-tris(hydroxymethyl)aminomethane
  • 3AB 3 -amino-2 -butanol
  • TA40 Crystals tri s(hydroxymethyl)aminom ethane
  • DMAMP80 2- dimethylamino-2-m ethylpropanol
  • AMP 2-amino-2-methyl-l -propanol
  • Iso-DMAMP 1,3 -propanediol
  • DEAAMP 2,2'-((2-amino-2- methylpropyl)azanediyl)bis(ethan-l-ol)
  • TA40 2,2'-((2-amino-2- methylpropyl)azanediyl)bis(ethan-l-ol)
  • TA40 2,2'-((2-amino-2- methylpropyl)azanediyl)bis(ethan-l-ol)
  • TA40 diethanolamine
  • DEA 2-((dimethylamino)methyl)butane-l,2-diol
  • Iso-DMAEPD 2-((3-aminopropyl)(butyl)amino)ethan-l-ol
  • APIBAE 2-amino-2-ethyl- 1,3 -propanediol
  • AEPD VOX 1000 2-amino-2-
  • FIG. 1 A provides changes in L
  • FIG. IB provides changes in a coordinate
  • FIG. 1C provides changes in b coordinate over 84 days.
  • 3 AB provides a coordinate value consistently close to 0 (Aa ⁇ l)over the time period (as compared to Aa >4 for amidoamine).
  • FIG. 1 A provides changes in L
  • FIG. IB provides changes in a coordinate
  • FIG. 1C provides changes in b coordinate over 84 days.
  • 3 AB provides a coordinate value consistently close to 0 (Aa ⁇ l)over the time period (as compared to Aa >4 for amidoamine).
  • 3 AB provides a b coordinate consistently close to 0 (Ab ⁇ 2) over the time period (as compared to Ab >70 for amidoamine, Ab >50 for DMTA V2, Ab >8 for TA40, Ab >8 for Iso-DMAEPD, Ab >7 for VantexT).
  • Example 3 Dispersant Demand of 3-Amino-2-Butanol for Paint Coatings
  • FIG. 2 provides the dispersant demand curves of TiCh (KRONOS 2190, from Kronos) with 0.05 wt.% of the corresponding additives (2-amino-2-methyl-l -propanol (“AMP”), 3 -amino-2 -butanol (“3AB”; of the present technology)), diethanolamine (“DEA”), or triethylamine (“TEA”)), or 25 wt.% NaOH solution, and in the presence of a polymeric dispersant (OROTANTM 731A ER, from Dow). As shown in FIG.
  • 2, 3 AB and AMP require the least amount of polymeric dispersing agent, namely OROTANTM 731 A ER, (0.28 wt.% of dispersant per pigment weight) to achieve the lower Krebs viscosity (compared to 0.38 wt.% for DEA, 0.56 wt.% for TEA, and 0.60 wt.% for NaOH).
  • An optimum (or minimum) concentration of polymeric dispersing agents reduces the hydrophilicity of the dry film leading to an improvement of several parameters such as: water resistance, chemical resistance, stain resistance, washability of the surface, lower microfoaming effect, and/or syneresis formation during storage.
  • a composition comprising a dispersion of a pigment and an additive, a binder and the additive, or a combination of the pigment, the binder, and the additive, wherein the additive comprises 3 -amino-2 -butanol.
  • composition of Paragraph A or Paragraph B wherein the composition comprises about 0.05 wt.% to about 2 wt.% of the additive.
  • composition of Paragraph H wherein the polymeric binder resin is selected from the group consisting of a polyacrylate, polyvinyl versatate, polyethylene-vinyl acetate, polyester, or a combination of two or more thereof.
  • N The composition of any one of Paragraphs A-M, wherein the additive is purified such that one enantiomer is present at levels greater than 99%.
  • composition of any one of Paragraphs A-N further comprising about 10 wt.% to about 75 wt.% pigment.
  • composition of any one of Paragraphs A-R further comprising a dispersing agent.
  • T The composition of any one of Paragraphs A-S, wherein the composition comprises 0.01 wt.% to 10 wt.% dispersing agent.
  • composition of any one of Paragraphs A-T further comprising one or more of a cosolvent, coalescent, leveling agent, thickener, rheology modifier, corrosion inhibitor, defoamer, wetting agent, dispersant, biocide, flow control agent based on (meth)acrylic homopolymers or silicon oils, or a combination of any two or more thereof.
  • AD A coating comprising the dried composition of any one of Paragraphs A- AC.
  • a method comprising adding to a composition comprising an aqueous dispersion comprising a pigment an effective amount of an additive to raise the pH of the composition, stabilize the dispersion of the pigment in the composition, and/or at least partially neutralize any acidic compounds in the composition, wherein the additive comprises 3 -amino-2 -butanol.
  • a method comprising adding to a composition comprising an aqueous dispersion comprising a pigment and/or binder an effective amount of an additive to raise the pH of the composition, stabilize the dispersion of the pigment in the composition, and/or at least partially neutralize any acidic compounds in the composition, wherein the additive comprises 3 -amino-2 -butanol.
  • a composition comprising about 30 wt.% to about 99.99 wt.% 3-amino-2-butanol; about 0.01 wt.% to about 70 wt.% water; and optionally an amino alcohol other than 3 -amino-2 -butanol (an “other amino alcohol”).
  • composition of Paragraph AG comprising about 0.01 wt.% to about 60 wt.% of the other amino alcohol.
  • composition of Paragraph AH comprising not more than 1 wt.% of the other amino alcohol.
  • 2-butanol about 10 wt.% water, and less than 1 wt.% of the other amino alcohol.
  • composition of any one of Paragraphs AG-AP wherein the composition exhibits a biobased content of the 3 -amino-2 -butanol of at least about 10% as determined using radiocarbon analysis in accordance with ASTM D6866-24.
  • AR A method of making a composition of any one of Paragraphs AG-AQ, the method comprising combining 3 -amino-2 -butanol with a purity of at least 95 wt.% with sufficient water to provide the composition.

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Abstract

La présente technologie concerne de manière générale des compositions contenant du 3-amino-2-butanol. En particulier, la présente technologie concerne des compositions utilisées pour des peintures et des revêtements, qui contiennent du 3-amino-2-butanol. Dans certains modes de réalisation, la composition peut contenir une dispersion d'un pigment et d'un additif, et/ou une dispersion d'une résine liante polymère et d'un additif, l'additif présentant du 3-amino-2-butanol.
PCT/US2025/020120 2024-04-12 2025-03-15 Formulations de peinture et de revêtement contenant du 3-amino-2-butanol et leurs utilisations Pending WO2025216845A1 (fr)

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PCT/US2025/020120 Pending WO2025216845A1 (fr) 2024-04-12 2025-03-15 Formulations de peinture et de revêtement contenant du 3-amino-2-butanol et leurs utilisations
PCT/US2025/020121 Pending WO2025216846A1 (fr) 2024-04-12 2025-03-15 Compositions de fluide de travail des métaux constituées du 3-amino-2-butanol et leurs utilisations
PCT/US2025/020123 Pending WO2025216848A1 (fr) 2024-04-12 2025-03-15 Formulations de soins à domicile et de soins personnels comprenant du 3-amino-2-butanol et leur utilisation

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PCT/US2025/020123 Pending WO2025216848A1 (fr) 2024-04-12 2025-03-15 Formulations de soins à domicile et de soins personnels comprenant du 3-amino-2-butanol et leur utilisation

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Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3984298A (en) * 1970-12-28 1976-10-05 Haber Instruments, Incorporated Electromolecular propulsion in semiconductive media
DE19625773A1 (de) * 1996-06-27 1998-01-02 Hoechst Ag Dispersionen oder Lösungen von Polymeren und Polymermischungen in Wasser
CA2443902C (fr) * 2001-04-11 2011-05-31 The Lubrizol Corporation Lubrifiants contenant un copolymere olefinique et un copolymere d'acrylate
DE10163251A1 (de) * 2001-12-21 2003-07-03 Henkel Kgaa Neue Entwicklerkomponenten
CN101765652A (zh) * 2007-07-30 2010-06-30 出光兴产株式会社 水性金属加工油剂
US8211827B2 (en) * 2007-11-30 2012-07-03 Kao Corporation Dye receptor layer compositions
US20090149359A1 (en) * 2007-12-10 2009-06-11 Hundley Lloyd E Formulation of a metal working fluid
WO2012152639A1 (fr) * 2011-05-06 2012-11-15 Chemetall Gmbh Fluide de travail de métal sans cov sans amine
EP3533780A1 (fr) * 2011-07-28 2019-09-04 ANGUS Chemical Company Composés d'alcool aminé et leur utilisation en tant qu'additifs à teneur de cov nulle ou basse pour peintures et revêtements
JP5873180B2 (ja) * 2011-10-03 2016-03-01 ザ プロクター アンド ギャンブルカンパニー ヘアケア組成物及びその使用方法
CA2878966A1 (fr) * 2012-07-26 2014-01-30 Butamax Advanced Biofuels Llc Purification de butanol
DE202014010354U1 (de) * 2014-03-06 2015-05-15 Clariant International Ltd. Korrosionsinhibierende Zusammensetzungen
EA201890618A1 (ru) * 2015-09-01 2018-10-31 Ферст Вэйв Байо, Инк. Способы и композиции для лечения состояний, ассоциированных с аномальными воспалительными ответами
IT201800004333A1 (it) * 2018-04-09 2019-10-09 Procedimento per il trattamento dei capelli
US11525102B2 (en) * 2020-12-21 2022-12-13 Kraton Polymers Llc Metal-working fluid compositions and methods for making
US20240342067A1 (en) * 2021-08-09 2024-10-17 Wella Germany Gmbh Hair Coloring Compositions Comprising 2-Amino-1-Propanol As Alkalising Agents
US20230275230A1 (en) * 2022-02-25 2023-08-31 Enevate Corporation Aqueous based polymers for silicon anodes
KR20250020516A (ko) * 2022-05-31 2025-02-11 바스프 에스이 코발트 및 구리를 포함하는 기판의 세정을 위한 조성물, 이의 용도 및 방법
GB2619938A (en) * 2022-06-21 2023-12-27 Metalube Ltd Metalworking fluid concentrate

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