WO2020229897A1 - Systèmes de solvant et procédés associés - Google Patents

Systèmes de solvant et procédés associés Download PDF

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Publication number
WO2020229897A1
WO2020229897A1 PCT/IB2020/020023 IB2020020023W WO2020229897A1 WO 2020229897 A1 WO2020229897 A1 WO 2020229897A1 IB 2020020023 W IB2020020023 W IB 2020020023W WO 2020229897 A1 WO2020229897 A1 WO 2020229897A1
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WO
WIPO (PCT)
Prior art keywords
solvent system
solvent
composition
vol
butyl ether
Prior art date
Application number
PCT/IB2020/020023
Other languages
English (en)
Inventor
Luiza Roza
Fernanda RIBASKI
Gregory JAKOCIUK
Carlos Roberto Tomassini
Original Assignee
Braskem S.A.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Braskem S.A. filed Critical Braskem S.A.
Priority to BR112021022800A priority Critical patent/BR112021022800A2/pt
Priority to EP20729176.6A priority patent/EP3969523A1/fr
Publication of WO2020229897A1 publication Critical patent/WO2020229897A1/fr

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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
    • C09D7/20—Diluents or solvents
    • 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
    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters

Definitions

  • embodiments disclosed herein relate to solvent systems that include an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • compositions that include at least one resin and a solvent system that includes an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • embodiments disclosed herein relate to methods of cleaning a surface of an article, the methods including contacting the surface of the article with a solvent system that includes an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent, where the solvent system is added in an amount effective to accomplish cleaning.
  • embodiments disclosed herein relate to a method of coating a surface of an article, the method included applying a composition onto the surface, where the composition includes at least one resin and a solvent system that includes an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • embodiments disclosed herein relate to a method of thinning a first composition, the method including adding a solvent system that includes an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent, into the first composition.
  • embodiments disclosed herein relate to a method of adhering two articles together, the method comprising applying a composition to at least one of two articles and bringing the two articles in contact with each other, thereby adhering the two articles, where the composition includes at least one resin and a solvent system that includes an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • Alkyl tert-butyl ethers such as ethyl tert-butyl ether (ETBE) are widely used as an octane booster in gasoline.
  • ETBE ethyl tert-butyl ether
  • ETBE is an attractive candidate as a solvent as it may be produced by the reaction of sugarcane-sourced ethanol with isobutylene in a catalytic reaction.
  • the use of renewably-sourced alcohol results in this process providing low carbon emissions (0.34 kg CO2 eq./kg) and yields a final product that may contain 33% biobased carbon.
  • embodiments disclosed herein relate to solvent systems that include an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • the alkyl tert-butyl ether may be ethyl tert-butyl ether.
  • embodiments disclosed herein relate to compositions that include a resin and a solvent system comprising an alkyl tert-butyl ether and at least one solvent selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • embodiments disclosed herein relate to methods for using a solvent system, which may include an alkyl tert-butyl ether and at least one selected from the group consisting of ethanol, a hydrocarbon solvent, and an oxygenated solvent.
  • said methods may include thinning a composition, adhering two articles together, or cleaning a surface.
  • solvents may be used singly, a single solvent typically does not possess ideal values for both properties, necessitating the use of a solvent mixture or system. Furthermore, the cost of a solvent is also extremely important, not only in terms of production but in storage and handling as well. Therefore, the use of a low-density solvent is often advantageous.
  • Embodiments described herein may advantageously provide solvent systems that can dissolve a wide array of solutes, may possess a suitable evaporation rate, and are economically advantageous. Additionally, components of the solvent systems may be at least partially derived from renewable carbon sources, mitigating some of the negative repercussions of solvent use.
  • Solvent systems in accordance with one or more embodiments of the present disclosure may include one or more alkyl tert-butyl ethers.
  • the alkyl group of the alkyl tert-butyl ether may be a Cl -CIO linear or branched hydrocarbon group.
  • the alkyl group may be a Cl- C4 linear or branched hydrocarbon group.
  • the alkyl tert-butyl ether of particular embodiments may be ethyl tert-butyl ether.
  • solvent systems in accordance with embodiments of the present disclosure may further include one or more additional solvents or co-solvents.
  • the one or more solvents may be selected from any suitable solvent known to one of skill in the art, but in particular embodiments the one or more solvents may be selected from the group consisting of hydrocarbon solvents and oxygenated solvents, including alcohols.
  • the hydrocarbon solvents of one or more embodiments are not particularly limited and may include any suitable solvents, including aromatic and aliphatic species.
  • the aliphatic hydrocarbon solvents of one or more embodiments may be saturated or unsaturated and linear, branched or cyclic.
  • the aliphatic hydrocarbon solvent may be a C6 to CIO hydrocarbon solvent.
  • the aliphatic hydrocarbon solvent may be a C6 to C8 hydrocarbon solvent.
  • the aromatic hydrocarbon solvents of one or more embodiments may be monocyclic and may be substituted or unsubstituted.
  • the solvent systems of some embodiments may particularly include alkylbenzenes.
  • the solvent system may include one or more of toluene, xylene, and other alkylbenzenes such as mesitylene, ethylbenzene, diethylbenzene, triethylbenzene, cumene, cymene, and the like.
  • the oxygenated solvents of one or more embodiments are not particularly limited and may include any suitable oxygen-containing solvent such as ketones, esters, glycols ethers, and alcohols, among others.
  • solvent systems of some embodiments may include ethanol.
  • Solvent systems in accordance with embodiments of the present disclosure may include any suitable amount of alkyl tert-butyl ether.
  • the amount of alkyl tert- butyl ether may range from a lower limit selected from any one of 2 vol%, 3 vol%, 5 vol%, 10 vol%, 15 vol%, and 20 vol% to an upper limit selected from any one of 15 vol%, 20 vol%, 25 vol%, 30 vol%, and 35 vol%, where any lower limit may be paired with any upper limit.
  • the alkyl tert-butyl ether is present in the solvent system in an amount ranging from 5 to 30 vol%.
  • Solvent systems in accordance with embodiments of the present disclosure may include an alkyl tert-butyl ether in an amount of 5 to 30 vol% and an oxygenated solvent in an amount of 70 to 95 vol%.
  • the amount of oxygenated solvent may range from a lower limit selected from any one of 70 vol%, 73 vol%, 75 vol%, 77 vol%, and 80 vol% to an upper limit selected from any one of 80 vol%, 83 vol%, 85 vol%, 87 vol%, and 90 vol%, where any lower limit may be paired with any upper limit.
  • the oxygenated solvent may be ethanol.
  • the solvent system may contain an alkyl tert-butyl ether in an amount of 5 to 30 vol%, and a mixture of two or more oxygenated solvents in a total amount of 70 to 95 vol%.
  • Each of the oxygenated solvents may be present in an amount of 5 to 90 vol%, relative to the total volume of the solvent system, and each oxygenated solvent may be contained in an amount either the same as or different from one another.
  • the amount of each oxygenated solvent may range from a lower limit selected from any one of 5 vol%, 10 vol%, 15 vol%, 20 vol%, 30 vol%, 40 vol%, 50 vol%, 60 vol%, 70 vol%, and 80 vol% to an upper limit selected from any one of 10 vol%, 15 vol%, 20 vol%, 30 vol%, 40 vol%, 50 vol%, 60 vol%, 70 vol%, 80 vol% and 90 vol%, where any lower limit may be paired with any upper limit.
  • Solvent systems in accordance with embodiments of the present disclosure may include an alkyl tert-butyl ether in an amount of 5 to 30 vol%, one or more oxygenated solvents in a total amount of 25 to 80 vol%, and one or more hydrocarbon solvents in a total amount of 15 to 70 vol%.
  • one of the one or more hydrocarbon solvents is an aromatic solvent, such as an alkylbenzene like xylene, toluene, or mixtures thereof.
  • the solvent system may comprise two or more hydrocarbon solvents, where at least one is an aliphatic solvent and at least one is an aromatic solvent.
  • the amount of an aromatic solvent may range from a lower limit selected from any one of 15 vol%, 20 vol%, 25 vol%, 30 vol%, 40 vol%, 50 vol%, and 60 vol% to an upper limit selected from any one of 20 vol%, 25 vol%, 30 vol%, 40 vol%, 50 vol%, 60 vol%, and 70 vol%, where any lower limit may be paired with any upper limit.
  • the amount of an aliphatic solvent may range from a lower limit selected from any one of 15 vol%, 20 vol%, 25 vol%, 30 vol%, 40 vol%, 50 vol%, and 60 vol% to an upper limit selected from any one of 20 vol%, 25 vol%, 30 vol%, 40 vol%, 50 vol%, 60 vol%, and 70 vol%, where any lower limit may be paired with any upper limit.
  • the total amount of the one or more oxygenated solvents may range from a lower limit selected from any one of 25 vol%, 30 vol%, 40 vol%, 50 vol%, 60 vol%, and 70 vol% to an upper limit selected from any one of 30 vol%, 40 vol%, 50 vol%, 60 vol%, 70 vol%, and 80 vol%, where any lower limit may be paired with any upper limit.
  • solvent systems in accordance with the present disclosure may have a bio-based carbon content, as determined by ASTM D6866-18 Method B, of at least 5%, of at least 10%, of at least 20%, or of at least 30%, and up to 33%, 50%, 75%, 90%, or 100%.
  • the alkyl tert-butyl ethers of one or more embodiments may be synthesized from an alcohol that contains renewably- sourced carbon.
  • Sources of the renewable carbon may include plant-based sources such as sugar cane and sugar beet, maple, date palm, sugar palm, sorghum, American agave, corn, wheat, barley, sorghum, rice, potato, cassava, sweet potato, algae, fruit, materials comprising cellulose, wine, materials comprising hemicelluloses, materials comprising lignin, wood, straw, sugarcane bagasse, sugarcane leaves, corn stover, wood residues, paper, and combinations thereof.
  • plant-based sources such as sugar cane and sugar beet, maple, date palm, sugar palm, sorghum, American agave, corn, wheat, barley, sorghum, rice, potato, cassava, sweet potato, algae, fruit, materials comprising cellulose, wine, materials comprising hemicelluloses, materials comprising lignin, wood, straw, sugarcan
  • the ethyl tert-butyl ether of one or more embodiments may be produced from biologically sourced ethanol obtained by the fermentation of sugars or hydrolyzed starch, derived from the renewable sources of carbon detailed above. It is also envisioned that the biobased ethanol may be obtained from hydrolysis based products from cellulose and hemi- cellulose, which can be found in many agricultural by-products, such as straw and sugar cane husks. This fermentation is carried out in the presence of varied microorganisms, the most important of such being the yeast Saccharomyces cerevisiae.
  • alkyl tert-butyl ether of one or more embodiments of the present disclosure may be synthesized by any suitable method known to one of skill in the art.
  • alkyl tert-butyl ether is prepared by the reaction of a suitable alcohol with isobutylene.
  • the isobutylene may be derived from crude oil or natural gas-sourced butane, or from a biobased process utilizing any of the above described plant sources such as from use of sucrose as a feedstock in an Escherichia coli platform (available, for example, from Global Bioenergies) or from conversion of 3-hydroxyisovalerate to isobutene as a side activity of mevalonate diphosphate decarboxylase or on isobutanol dehydration as a side activity of engineered oleate hydratase.
  • a technical parameter that can be very important for solvent selection is the evaporation rate. Evaporation rate is directly associated to drying time of coatings and adhesives and therefore to productivity.
  • alkyl tert- butyl ethers such as ethyl tert-butyl ether (ETBE) may have a high evaporation rate even relative to traditional solvents like acetone and methyl ethyl ketone.
  • EBE ethyl tert-butyl ether
  • solvent systems in accordance with the present disclosure may have an evaporation rate of 200 or more, 300 or more, 400 or more, 500 or more, 600 or more, or 800 or more, relative to butyl acetate having an evaporation rate of 100.
  • the evaporation rate may be measured by ASTM D 3539 Standard Test Methods for Evaporation Rates of Volatile Liquids by Shell Thin- Film Evaporometer.
  • the solvent system may have an evaporation rate of at least 400.
  • solvent systems in accordance with the present disclosure may have a maximum incremental reactivity of less than 10 g Cb/g VOC, less than 7 g Cb/g VOC, less than 5 g 0 3 /g VOC, less than 3 g 0 3 /g VOC, less than 2 g 03/g VOC, or less than 1 g 03/g VOC.
  • the solvent system may have a maximum incremental reactivity of less than 3 g 0 3 /g VOC. The maximum incremental reactivity may be measured in accordance with a method of William P.L. Carter; Development of Ozone Reactivity Scales for Volatile Organic Compounds, Air & Waste, 1994, 44:7, 881-899.
  • solvent systems in accordance with the present disclosure may have a density of less than 0.95 g/cm 3 , less than 0.90 g/cm 3 , less than 0.85 g/cm 3 , less than 0.80 g/cm 3 , or less than 0.75 g/cm 3 .
  • the solvent system may particularly have a density of less than 0.85 g/cm 3 .
  • the density of the solvent system of one or more embodiments may be measured at 20°C and 1 atm.
  • Wettability is the ability of a liquid to maintain contact with a solid surface, which is dependent upon the nature of the intermolecular forces that arise when the two are brought together and the surface tension of the liquid.
  • alkyl tert-butyl ethers such as ETBE, demonstrate a very low surface tension relative to other solvents.
  • solvent systems in accordance with the present disclosure may have a surface tension of less than 26 dynes/cm, less than 24 dynes/cm, less than 22 dynes/cm, or less than 20 dynes/cm.
  • Some alkyl tert-butyl ethers, such as ETBE, are considered to be a non- carcinogenic and non-mutagenic solvent. ETBE also has a low Maximum Incremental Reactivity (MIR), a value that quantifies the propensity of a chemical compound to react in the atmosphere to form ground-level ozone.
  • MIR Maximum Incremental Reactivity
  • solvent systems in accordance with the present disclosure may have an MIR value of less than 6.0, less than 4.0, less than 3.0, less than 2.5, or less than 2.2 g Cb/g product.
  • Solvent systems according to the present disclosure will generally possess physical properties suitable for the intended use of the solvent system and/or the compositions produced therefrom.
  • One of ordinary skill in the art will, with the benefit of this present disclosure, appreciate that altering the relative amounts and/or identities of the components of a solvent system will influence the properties of the system.
  • compositions that include an aforementioned solvent system and at least one solute.
  • the solute is fully dissolved in the solvent system.
  • the solute of one or more embodiments is not particularly limited.
  • the solute may be one or more of a resin or polymer.
  • the resins may be selected from acrylic resins, nitrocellulose resins, polyester resins, polyol polyester resins, epoxy resins, alkyd resins, melamine resins, maleic resins, phenolic resins, isocyanate-based resins, polyurethane-based resins, polychloroprene, polyvinyl chloride, chlorinated polyvinyl chloride, styrene butadiene styrene, styrene butadiene, styrene isoprene styrene and ethylene-vinyl acetate (EVA).
  • EVA ethylene-vinyl acetate
  • HSPs Hansen solubility parameters
  • Each of the solvent and solute may be described by 3 parameters: 5D - the energy of the dispersion forces between molecules, dr - the energy of the dipole intermolecular forces between molecules, and 5H - the energy of the hydrogen bonds between molecules.
  • HSPs the chemical affinity of the solvent can be evaluated for different resins. The closer the solvent’s HSPs are to the resin’s, the more likely it is to dissolve it.
  • Table 5 is a comparison between the HSPs of an alkyl tert-butyl ether (specifically, ETBE) and other oxygenated and aromatics solvents. It can be observed that the parameters are similar to both families of solvents.
  • compositions in accordance with the present disclosure may have a relative energy difference between a solvent system and solute of less than 1.1, less than 1.0, less than 0.9, or less than 0.8.
  • Compositions in accordance with one or more embodiments of the present invention may include one or more additives.
  • the selection of the one or more additives is not particularly limited, and will be highly dependent upon the intended application of the composition.
  • the at least one additive may be selected from the group consisting of pigments, dyes, carriers, fillers, and dullness agents.
  • the composition of one or more embodiments may be, for example, a paint composition, a varnish composition, a lacquer composition, an adhesive composition, or a finish composition.
  • solvent systems and compositions may be used in a wide array of methods.
  • the uses of solvent systems and compositions in accordance with the present disclosure are not limited to the methods described herein.
  • the solvent systems of one or more embodiments may be used in cleaning compositions, printing inks, varnishes, adhesives, lacquers, or thinners.
  • solvent systems in accordance with the present disclosure may be used in a method of cleaning a surface of an article.
  • the method may include contacting the surface of the article with the solvent system.
  • the amount of solvent system used is not particularly limited but will generally be an amount effective to accomplish cleaning.
  • the cleaning may generate a composition that includes the solvent system and the components that were removed from the surface of the article.
  • compositions may include applying any of the aforementioned compositions to a surface of an article, the composition coating the surface thereof.
  • solvent systems in accordance with the present disclosure may be used in a method of thinning a first composition, the method including adding any of the aforementioned solvent systems to the first composition.
  • the identity of the first composition is not particularly limited, but may be a one or more of an alkyl resin, a nitrocellulose resin, or a polyurethane.
  • Methods in accordance with one or more embodiments of the present disclosure may involve using the aforementioned compositions to adhere the surfaces of two articles together.
  • the methods may include applying the composition to the surface of at least one of the two articles and bringing the two articles into contact with each other.
  • the solvent system may be designed to have a lower evaporation rate, depending on the type of adhesive, for example, and the desired adhesive strength. That is, in some instances, a lower evaporation rate may be desirable to allow the polymer chains to better intermingle (and adhere together) prior to the evaporation of the solvent system.
  • Particular types of adhesive resins that are envisioned as being used with the solvent system of the present disclosure include polyurethane-based resins, polychloroprene, polyvinyl chloride, chlorinated polyvinyl chloride.
  • Examples ⁇ - ⁇ are solvent systems that are suitable for thinning applications.
  • Examples 1-4 contain ETBE and exhibit advantageous properties (such as density, MIR, RED) as compared to Comparative Example 1, which does not contain ETBE.
  • alkyl tert-butyl ethers may be used in a wide range of formulations using resins such as polychloroprene, polyurethane, PVC (polyvinyl chloride) and also cPVC (chlorinated polyvinyl chloride). See Tables 10-14. Toluene free compositions for polychloroprene-based adhesives have been developed. Polychloroprene-based resins are widely used in contact adhesives for manufacturing shoes and footwear, in wood industry and furnitures due to their versatility, as they present good results in bonding leather, textiles and other materials
  • Table 10 Solvent systems for a polychloroprene based adhesive
  • Table 11 Solvent systems for a PU based adhesive
  • Table 12 Solvent systems for a PVC based adhesive
  • Table 13 Solvent systems for a cPVC based adhesive

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Detergent Compositions (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

Un système de solvant selon l'invention peut comprendre un alkyl tert-butyl éther et au moins un élément choisi dans le groupe constitué par l'éthanol, un solvant hydrocarboné et un solvant oxygéné. Dans certains modes de réalisation, l'alkyl tert-butyl éther peut être l'éthyl tert-butyl éther. Une composition peut comprendre le système de solvant et au moins une résine.
PCT/IB2020/020023 2019-05-16 2020-05-15 Systèmes de solvant et procédés associés WO2020229897A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
BR112021022800A BR112021022800A2 (pt) 2019-05-16 2020-05-15 Sistema de solvente, composição, métodos para limpar e revestir uma superfície de um artigo, para diluir uma primeira composição e para aderir dois artigos juntos, e, uso do sistema de solvente
EP20729176.6A EP3969523A1 (fr) 2019-05-16 2020-05-15 Systèmes de solvant et procédés associés

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201962848881P 2019-05-16 2019-05-16
US62/848,881 2019-05-16

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WO2020229897A1 true WO2020229897A1 (fr) 2020-11-19

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EP (1) EP3969523A1 (fr)
BR (1) BR112021022800A2 (fr)
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5348624A (en) * 1991-11-12 1994-09-20 Institut Francais Du Petrole Process for separating ethyl tert-butyl ether and ethanol
CN103865321A (zh) * 2014-02-27 2014-06-18 安徽颍美彩印包装有限公司 一种水性柔性版油墨及其制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5348624A (en) * 1991-11-12 1994-09-20 Institut Francais Du Petrole Process for separating ethyl tert-butyl ether and ethanol
CN103865321A (zh) * 2014-02-27 2014-06-18 安徽颍美彩印包装有限公司 一种水性柔性版油墨及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 201456, Derwent World Patents Index; AN 2014-Q26603, XP002799576 *
WILLIAM P.L. CARTER: "Development of Ozone Reactivity Scales for Volatile Organic Compounds", AIR & WASTE, vol. 44, no. 7, 1994, pages 881 - 899

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BR112021022800A2 (pt) 2022-01-18

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