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
  • 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
• • 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
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
• • 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
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P20/00—Technologies relating to chemical industry
  • Y02P20/50—Improvements relating to the production of bulk chemicals
  • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

• the present invention relates to a process for the treatment of a material other than the human body, using a composition containing at least one dianhydrohexitol ether, preferably chosen from dimethylisosorbide (“DMI”) and dimethylisoidide
• DMIi dimethyl-1-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-amino
• DMI dianhydrohexitol ether
• This compound is particularly recommended in the treatment of the human body as a vectoring agent of active ingredients allowing them to reach their target more effectively inside the human body. It is especially used as a "dermo-penetrant" to improve the penetration of active ingredients in the upper layers of the epidermis, protein (keratin). Its use as a keratolytic agent vector in order to improve the percutaneous absorption of said agent is, for example, described in the patent application WO 2004/105722.
• the finding can be made so that, to date, the industrial and commercial exploitation of dianhydrohexitol ethers, including DMI, remains very limited in the field of the treatment of the human body and is non-existent in the other fields, in particular in the fields of detergency, inks and paints, building materials, metallurgy, printing, paper, textiles, plant protection products, adhesives, industrial coatings and electronics.
• the present invention relates to a method of treating a material other than the human body, comprising mixing or contacting said material to be treated with a composition
• a composition comprising: a) at least one compound A selected among the ethers of dianhydrohexitol, and b) at least one compound B chosen from alkaline agents, acidic agents, and solubilizing agents chosen from fatty alcohols at 25 ° C. other than isostearyl alcohol, non-fatty alcohols, terpene compounds, aldehydes, ketones, fluorinated compounds, sulfur compounds, ethers, esters and supercritical fluids.
• Treatment of a material other than the human body means any operation applied to any material, of an organic and / or mineral nature, with the exception of the only operations applied, directly and “in vivo", to the to be human, including on the skin or nails, for a therapeutic or cosmetic effect.
• treatment of a material other than the human body is meant in particular any operation applied to an inanimate material.
• the treated material according to the invention can have origins, natures, properties and highly variable destinations. It may be or contain at least a majority of:
• a metallic material of any kind which may be in the form of articles and structures of all shapes, sizes and functionalities such as rods, sheets, films, coatings, plates, sheets, parts for the automotive, naval or aeronautical industries, bodies, vehicles, frames, tanks, formwork, packaging boxes, molds, pipes , rolls, blankets, pumps, tools, apparatus, instruments, hardware, cutlery, cutlery, prostheses, parts for household appliances, electronic or microelectronic components, floppy disks, semiconductor components.
• a glass material, of a mineral or organic nature which may be in the form, for example, of fibers, walls, windows, verandas, aquariums, screens, windscreens, glasses, lenses, laboratory equipment, dishes, bottles,
• a mineral material in particular based on plaster, cement, mortar, grout, concrete, plaster, porcelain or ceramic, which may be, for example, in the form of panels, paving stones, coatings, slabs, plates, tiles, bricks, walls, posts, enclosures, bridges and other structures,
• - woody material in the form of wooden articles such as doors, windows, shutters, frames, poles, laths, floors, panels, tables, furniture, formwork, tools, instruments, including fiber-based articles wood and, optionally, fibers and / or mineral or plastic fillers, such as insulating panels or composite materials, - a plant material such as seeds, leaves, stems, flowers, fruits, vegetables, roots, cellulosic or hemicellulosic fibers or other plant extracts, - a material extracted from the animal body such as hides, skins, horns and wools,
• a textile material which may be in the form of yarns, filaments, fibers or textile webs, of natural or synthetic origin, woven or non-woven articles, clothing, wipes, curtains, cloths,
• a papermaking material such as paper fibers or sheets, a sheet of paper, flat or corrugated cardboard,
• polysaccharides, polylactates, polyhydroxy-alkanoates, polyolefin resins, polyesters, polyamides, polyurethanes, acrylics, epoxies, elastomers, natural rubbers, etc. which may be, for example, in the form of latices, sheets, films, coatings, plates, formwork, packaging, parts for the automobile or household appliance, tires, electronic or microelectronic components, diskettes, prostheses, a fat such as an oil or a grease, mineral or organic origin, a fuel or a "bio-fuel” such as bioethanol or esters of vegetable oils,
• material other than the human body in particular a material chosen from metal materials, glass materials, mineral substances, ligneous materials, vegetable matter, substances extracted from the animal body, textile materials, paper materials, polymeric materials of natural or synthetic origin, fats, fuels, water, fluids aqueous, air, gas, and mixtures of these materials.
• said material is not in gelled form.
• the treatment to which said material is subjected in accordance with the invention may consist of a treatment of all or only part of the surface or mass constituting the material. This treatment may have the purpose or effect of cleaning and / or ennobling all or part of this material and in particular consist of operations:
• compositions in different forms liquid, emulsified, pasty, solid, gaseous, aerosol
• a multitude of compositions in different forms including in the form of finished or semi-finished articles of structures, dimensions and forms of presentation that are very variable, and which have necessarily a wide variety of functionalities such as the following compositions, cleaning, detergent, stain remover, degreaser, degreaser, dust remover, lubricating, antifreeze, disinfectant, deodorant, impregnating, perfuming, decorative, adhesive, binder or film forming agents.
• compositions may be in particular compositions, fully formulated or not, directly usable in the state or not, perfumes and ambiencers, paints, latex, coating sauces, inks, lacquers, stains and wood varnishes, glues and adhesives, foundry binders, cutting oils, machining fluids, drilling fluids, photographic baths, fuels, paint removers, window cleaners, liquid detergents, pulverulent or in tablet form, especially for washing dishes, linen or floors, precision cleaning compositions for photolithography, deicing compositions, fountain solutions, coating compositions for boxes or metal coils ("can coating compositions" or "coil coating compositions”), impregnated wipes or phytosanitary products including fungicidal or herbicidal activity.
• any means implemented during its preparation may present all the criteria listed below: a) be sufficiently effective for any function for which it is intended for a given treatment, b) not to deteriorate, and if possible improve, the conditions of preparation and / or the conditions of use of any composition in which it is incorporated with a view to a given treatment, c) not to deteriorate, and if possible improve, the intermediate and final performance and physical characteristics of said composition or of any material treated with said composition, d) to be of high safety and minimum of inconvenience, particularly in terms of protection of man and the environment, (e) be derived from materials of natural origin and, if possible, renewable.
• a) is really effective, for example as a cleaning agent, wetting agent, dispersant, lubricant, compatibilizer, and / or coalescing agent.
• b) is advantageously usable in compositions intended to be applied (i) both cold and hot and / or (ii) both neutral pH and acidic or basic pH.
• c) does not deteriorate, if possible improves, the physical, organoleptic and more generally applicative characteristics, for example the film-forming power, the wetting power, the viscosity, the volatility, miscibility with water, chemical stability, color, transparency and / or odor, of said compositions but also the characteristics, including organoleptic characteristics, of any material, for example of any glass surface, of metal of wood, paper or plastic, treated with said compositions.
• (d) is more ecologically acceptable than adjuvants of the same classically used functionality, for example glycol ethers, fossil hydrocarbons or chlorinated solvents in general, and in particular:
• VOCs volatile organic compounds
• lactic acid esters has, for example, been described: in the preparation of paints, lacquers or varnishes in the patents US Pat. No. 3,985,691, EP 659,856 or EP 851,298,
• compositions containing lactic acid esters have a certain number of drawbacks, and in particular: a lack of solvent power for highly hydrophobic materials, a relatively pronounced odor, a relatively low flash point (46 ° C. for lactate). ethyl) and high flammability, high vapor pressure, high instability in alkaline medium, resistance to relatively weak hydrolysis and an irritating character (presence of free lactic acid).
• fatty acid esters for increasing the flash point of the following compositions (WO 01/18162) to tertiary amines for improving the odor thereof (WO 03/016449), to d-limonene in order to improve the possibilities of use in general, including the solvent power for highly hydrophobic materials (US 6,797,684).
• solvents recognized as dangerous for man and / or the environment, it has also been proposed to replace them, in whole or in part, in association or not with lactic acid esters, with compositions based on products such as vegetable oil methyl esters, dicarboxylic acid esters or dibasic esters ("Dibasic
• Esters "or” DBE ”) or terpenes such as d-limonene are examples of terpenes such as d-limonene.
• methyl esters of vegetable oils eg rapeseed, soya, sunflower or castor oils: pronounced odor, pronounced color, immiscibility in water, absence of rinsability, limited solvent power (Applicable to few materials and with often limited effectiveness), viscosity often unsuitable, cold-setting ability
• dibasic esters for example dimethyl esters of adipic, glutaric or succinic acids and mixtures thereof: limited solvent power, low miscibility with water, poor rinsability, sometimes unsuitable viscosity (either too low or too high), insufficient stability, irritating character due to the presence of free acids, - terpenes (d-limonene): immiscibility in water , not rinsing, relatively low flash point (48 ° C), irritating, low chemical stability (auto-oxidation).
• the Applicant Company has found that in the general field of processing a subject other than the human body, it is now possible to have a means which: not only, as such, verifies all the criteria a) to d) above, - but also makes it possible advantageously to formulate, in particular with respect to said criteria, new compositions based on additives of a chemical nature or of very varied functionality (s).
• a dianhydrohexitol ether (hereinafter referred to as "compound A”) as a component of said compositions in combination with a compound (hereinafter referred to as "compound B”) selected from certain solubilizing agents, alkaline agents and acidic agents.
• compound A a dianhydrohexitol ether
• compound B a compound selected from certain solubilizing agents, alkaline agents and acidic agents.
• the subject of the present invention is a process for treating a material other than the human body, comprising mixing or bringing said material into contact with a composition comprising: a) at least one compound A selected from the group consisting of dianhydrohexitol ethers, and b) at least one compound B selected from alkaline agents, acidic agents, and solubilizing agents selected from liquid alcohols at 25 ° C.
• dianhydrohexitol is particularly meant isosorbide, isomannide, isoidide, isogalactide and any mixture of at least two of these products.
• dianhydrohexitol ether is intended to mean, in particular, any compound A chosen from dianhydrohexitol monoethers, dianhydrohexitol diethers and mixtures of these ethers.
• alkyl ethers of dianhydrohexitols in particular methyl, ethyl, hexyl or 2-ethylhexyl ethers of isosorbide, isomannide and isoidide.
• Said compound A may in particular consist, in whole or in majority (i.e for at least 50% of its dry matter), dimethylisosorbide (“DMI”), diethylisosorbide (“DEI”), di-2-ethylhexylisosorbide
• DMI dimethylisosorbide
• DEI diethylisosorbide
• Said compound A may be present in all proportions within the composition used in the process of the invention. It can thus, depending on the nature and the destination of said composition: be the majority component of said composition and represent from 51 to 99.8%, especially from 55 to 99.5%, of the weight of said composition, or conversely, represent less than 50%, especially 10 to 45%, of the weight of said composition.
• the dianhydrohexitol ether (compound A) preferably represents more than 5%, preferably more than 10% and more preferably still more than 15%, of the weight of said composition.
• compound A and compound B are present in the composition used in the process of the invention in a weight ratio of compound A / compound B, expressed in dry weight / dry weight, of between 2/98. and 98/2, preferably between 5/95 and 95/5.
• solubilising agent is chosen from:
• fatty alcohols which are liquid at 25 ° C. other than isostearyl alcohol, such as butanol, isobutanol, isobutylcarbinol, hexanol, heptanol, octanol, nonanol and decanol; fatty alcohols such as isosorbide and pentitols, glycerol, methanol, ethanol, 2-butoxyethanol, isopropanol, propan-1-ol and alcohol benzyl, - terpene compounds such as d-limonene, dipentene, pinene, citrus, pine, eucalyptus or camphor essential oils, turpentine spirits, aldehydes such as benzaldehyde and its derivatives ketones such as N-methylpyrrolidone (NMP), cyclohexanone and isophorone, fluorinated compounds, in particular hydrofluoroethers (HFE), hydrofluorocarbons
• glycerol such as triacetin, tributyrin, tricapryline, trioctanine or triolein,
• non-fatty monoacids such as lactates or acetates of methyl, ethyl, butyl, isobutyl, propyl, isopropyl, amyl or benzyl,
• non-fatty polyacids such as citrates, adipates, succinates or glutarates of methyl or isobutyl,
• fatty acids especially derived from vegetable fats, for example methyl, n-propyl, isopropyl, butyl or ethylhexyl esters, supercritical fluids, in particular supercritical CO 2 .
• the solubilizing agent combined with the dianhydrohexitol ether in the composition used according to the invention has: a) a vapor pressure, at 25 ° C., of less than 13.3 Pa, preferably more than 10 Pa, and / or b) a flash point greater than 60 ° C., preferably greater than 70 ° C. and more preferably still greater than 85 ° C., and / or (c) a biodegradability such that after 28 days at least 20%, preferably at least 70%, of said solubilizing agent has been degraded.
• Biodegradability is measured here according to the method, hereinafter referred to as "OECD 302 B", recommended by the OECD under the following N ° and Title: N ° 302 B Intrinsic biodegradability: Zahn-Wellens test / EMPA ('Inherent Biodegradability: Zahn - Wellens / EMPA Test').
• said solubilising agent is chosen from the group comprising non-fatty alcohols, esters of glycerol and of dianhydrohexitols, non-fatty monoacid esters, preferably lactates and acetates, polyunsaturated fatty acid esters, fatty acid esters, terpene compounds, glycerol ethers, propylene glycol ethers, fluorinated compounds, sulfur compounds, supercritical fluids and mixtures of these products.
• Said solubilizing agent may then advantageously be chosen from the group comprising a) non-fatty alcohols, in particular isosorbide, glycerol, ethanol, propanol, isopropanol and 2-butoxyethanol, b) glycerol esters.
• esters in particular methyl, ethyl, n -butyl and iso-butyl, n-propyl and iso-propyl, hexyl and ethylhexyl, lactic, acetic, adipic, succinic, glutaric or fatty acids comprising from 3 to 24 carbon atoms, d) terpene compounds, particularly d-limonene and pinenes, e) glycerol ethers and f) mixtures of these products.
• solubilizing agent which is liquid at 25 ° C.
• dianhydrohexitol ethers have many other advantages than those hitherto actually described and exploited for more than 50 years and more particularly for DMI and ' in the field of treatment of the human body (lack of irritancy and toxicity to humans, low odor, miscibility with water in all proportions, high flash point).
• Biodegradability assessed according to the method recommended by the OECD under No. 301 A ( ⁇ DOC Die - Away Test ') higher than 20% at 28 days, in this case of the order of 25% and a intrinsic biodegradability aerobic
• hydrotrope a high power, i.e. a high ability to allow, in aqueous media, a solubilizing insoluble compounds such as for example some dyestuffs, high physicochemical stability both in neutral medium or in an acid medium alkali, and an absence of corrosive power vis-à-vis metals conventionally used in industrial environments such as steel, iron-smelting, lead, aluminum, copper, tin or brass.
• dibasic esters adjustment of the viscosity, improvement of the rinsability, improvement of the stability, reduction of the vapor tension, reduction of the irritating power, extension of the solvent power.
• NMP N-methylpyrrolidone
• the dianhydrohexitol ether (compound A) is minor to the solubilizing agent in the composition used according to the invention, which is then characterized in that:
• the solubilising agent is chosen from fatty alcohols at 25 ° C. other than isostearyl alcohol, non-fatty alcohols, terpene compounds, aldehyde compounds, ketones, fluorinated compounds, sulfur compounds, ethers, esters, and supercritical fluids, and the weight ratio (dry weight / dry weight) compound A / compound B is less than 50/50, preferably between 2/98 and 40/60.
• This ratio can in particular be between 5/95 and 25/75.
• compound B can also be chosen from alkaline agents.
• alkaline agents is intended in particular to mean compounds selected from the group consisting of ammonia, urea, hydroxides, silicates, metasilicates, aluminosilicates, borates, carbonates, bicarbonates, percarbonates, sulphates, phosphates, phosphonates and hypochlorites of metals.
• alkali or alkaline-earth metals in particular sodium, alkali or alkaline earth salts of fatty or non-fatty organic acids, in particular citric, lactic, gluconic, formic, tartaric, acetic, lauric, stearic or oleic acids, primary, secondary or tertiary amines, amino derivatives of alcohols, acids or acid polymers, in particular 2-amino-2-methyl-1-propanol ("AMP"), amino derivatives of di-, tri-, tetra or pentaacetic, mono- or disuccinic, tartaric, citric or phosphonic such as, for example, amino derivatives known to those skilled in the art under the abbreviations of NTA, EDTA, DTPA, EDTMP, MGDA, EDMS and EDDS, as well as mixtures of these products.
• AMP 2-amino-2-methyl-1-propanol
• the composition used according to the invention has a pH greater than 8, preferably greater than 8.5 and even more preferably between 9 and 13.
• a compound A such as DMI
• an alkaline agent such as disodium metasilicate or ammonia, for example in a detergent or cleaning composition, in particular with a pH greater than 8, had the effect of improving the degreasing and saponifying powers of said composition.
• compound B combined with dianhydrohexitol ether (compound A) according to the invention may also be chosen from acidic agents.
• Acidic agents means all acids, organic or inorganic, in particular those chosen from the group comprising hydrochloric, sulfuric, phosphoric, sulphamic, citric, lactic, gluconic, formic, tartaric, acetic, octanoic, oleic or benzoic acids; as well as mixtures of these acids.
• an acidic agent of organic origin is used.
• the composition used according to the invention has a pH of less than 5, preferably less than 4.5 and even more preferably between 1.5 and 4.
• the Applicant Company has in particular observed that a compound A such as DMI, combined with an acid such as lactic acid or sulphamic acid, for example in a descaling or descaling composition having a pH of less than 4.5, had the effect of to increase the solubilizing power of these.
• compositions used according to the invention may also contain one or more other constituents, these being especially chosen from the group comprising water, dyes, pigments, thickeners, gelling agents, active ingredients and surfactants.
• active ingredients especially biocides, nematicides, helicines, insecticides, raticides, fungicides, herbicides and repellents for animals.
• surfactants is meant all surfactants whether anionic, cationic, amphoteric or nonionic.
• the anionic surfactants may in particular be chosen from alkylbenzene sulfonates, paraffin sulfonates, olefin sulfonates, methyl ester sulfonates, alkyl ether sulphates, fatty alcohol sulphates, fatty acid soaps, sulphoalkyl fatty acid amides, sulphosuccinates, diglycolamide sulphates, acylated N-amino acids or polyoxyethylene carboxylates.
• the cationic surfactants may in particular be imidazolines, quaternary mono- or dialkylammonium or quaternary ammonium esters.
• amphoteric surfactants may in particular be amphoteric derivatives of betaine such as sulfonates and alkylamidopropylsulfobetaines or betaine ethoxylée.
• Nonionic surfactants which are the surfactants preferred in the context of the present invention, may especially consist of ethoxylated fatty alcohols, copolymers of alkylene oxide, in particular of ethylene oxide or propylene oxide.
• the surfactant in particular nonionic, has a biodegradability at 28 days of at least 20%, preferably at least 70% according to the method "OECD 302 B" mentioned above.
• a dianhydrohexitol ether such as DMI
• a nonionic surfactant such as an oxyethylenated alkylphenol
• compositions may consist in particular: a) in compositions intended for the treatment, in particular the surface treatment, of a woody material (wood), textile or paper, said compositions being chosen in particular from the group of paints, dyes, latex , varnishes, lacquers, stains, pickling compositions, dedusting compositions, inks, glues and coating colors, b) in compositions intended for the treatment, in particular the surface treatment, of a metallic material, said compositions consisting especially of compositions for washing, cleaning, wetting, rinsing, degreasing, dedusting, machining, cutting, stripping, abrasion, glazing, varnishing, anti-rust, anti-corrosion, lubrication, painting, gilding, brightening, coating (including "can coating compositions” and “coil coating compositions”), film-coating or film-making, c) in compositions for the treatment, in particular the surface treatment, of a glass material, said compositions being chosen especially from the group of washing compositions such as
• the material to be treated is a metal material, woody material, textile material or paper material and the method comprises contacting said composition with the material to be treated.
• the present invention also relates to the use, for the preparation of a treatment composition of a material other than the human body: a) at least one compound A chosen from dianhydrohexitol ethers, preferably dimethylisosorbide ("DMI"), and b) at least one compound B selected from alkaline agents, acidic agents, and solubilizing agents chosen from liquid fatty alcohols at 25 ° C. other than isostearyl alcohol, non-fatty alcohols, terpene compounds, aldehydes, ketones, fluorinated compounds, sulfur compounds, ethers, esters and supercritical fluids.
• DMI dimethylisosorbide
• the subject of the invention is a composition for treating a material other than the human body, characterized in that it comprises at least one dianhydrohexitol ether, preferably dimethylisosorbide ("DMI"), and at least one compound B selected from alkaline agents, acidic agents and solubilizing agents selected from fatty alcohols liquid at 25 ° C other than isostearyl alcohol, non-fatty alcohols, terpene compounds, aldehydes, ketones, fluorinated compounds, sulfur compounds, ethers, esters and supercritical fluids.
• DMI dimethylisosorbide
• compound B is a solubilizing agent chosen from fatty alcohols at 25 ° C. other than isostearyl alcohol, non-fatty alcohols, terpene compounds, aldehydes and ketones. fluorine compounds, sulfur compounds, ethers, esters, and supercritical fluids, and
• the weight ratio (dry weight / dry weight) compound A / compound B is less than 50/50, preferably between 2/98 and 40/60.
• the compositions of the present invention are preferably chosen from paints, dyes, latices, varnishes, lacquers, glues, varnishes, inks, coating colors, detergents, window washes, compositions of cleaning, washing, wetting, rinsing, degreasing, dedusting, machining, cutting, pickling, abrasion, glazing, varnishing, anti-rust, anti-corrosion, lubrication, gilding, brightening, laminating, coating, disinfecting or de-wetting, wipes, phytosanitary compositions, plant nutritive compositions and fertilizers.
• the subject of the present invention is furthermore the use of a dianhydrohexitol ether, in particular DMI, as a coalescence agent for a composition based on latex, especially chosen from aqueous paints, varnishes, lacquers, glues, stains , inks and sleeping sauces.
• a dianhydrohexitol ether in particular DMI
• DMI dianhydrohexitol ether
• EXAMPLE 1 Degreasing compositions of steel sheets.
• COMPOSITION 1 trichlorethylene (TCE) marketed by RIEDEL-DE HA ⁇ N under the reference number 24254, - COMPOSITION 2: dichloromethane (DCM) marketed by RIEDEL-DE HA ⁇ N under the reference number 34488,
• COMPOSITION 3 dipentene (DP) marketed by FLUKA under reference number 42560
• COMPOSITION 4 ethyl lactate (LE) marketed by SIGMA-ALDRICH
• COMPOSITION 5 dimethylisosorbide (DMI) produced by the Applicant in the form of a colorless, odorless, slightly viscous solution having a dimethylisosorbide purity of approximately 99.6%,
• - COMPOSITION 6 mixture in equal parts, by weight, of DMI constituting COMPOSITION 5 and DP constituting COMPOSITION 3
• - COMPOSITION 7 mixture in equal parts, by weight, of DMI constituting COMPOSITION 5 and LE constituent of COMPOSITION 4.
• compositions have as such the general properties given in the table below, said properties being designated and noted as follows:
• COMPOSITIONS 3 and 4 although they are of renewable origin while being biodegradable, have flash points too low so that a labeling RIO is necessary (flash points between 21 and 51 ° C).
• COMPOSITION 5 as such has very advantageous properties (sufficiently high flash point, excellent water rinsability, renewable origin and intrinsically biodegradable). It is possible with this composition to obtain, by simple rinsing with water, a dry surface, but a supply of energy is necessary.
• COMPOSITIONS 6 and 7, in accordance with the invention, have, compared to the COMPOSITIONS 3 and 4, the advantage of being much safer with regard to a risk of explosion and do not require the affixing of a RIO labeling. Compared to COMPOSITION 5,
• COMPOSITIONS 6 and 7 have the same advantageous properties while having a much better drying ability.
• CG 3 food mineral oil
• CG 4 molybdenum disulfide grease
• GC 5 mixture of mineral oil, paraffinic hydrocarbons and graphite
• GC 6 polydimethylsiloxane oil
• CG 7 polycoupe oily mixture
• CG 8 biostable polyvalent microemulsion
• CG 9 non-chlorinated special lubricant.
• an "overall score” is assigned according to the number of fatty substances for which the composition in question did not achieve the score of 3. This overall score, a maximum value of 10, is attributed as follows: 10/10: the composition obtained a score of 3 for all 9 fatty substances,
• composition obtained a score of 3 to 5 fat.
• COMPOSITIONS 4 and 5 appear, in this case, less effective than the other compositions tested. However, they have an undeniable degreasing effect and it is remarkable to note that
• COMPOSITION 5 based solely on DMI, makes it possible to eliminate, without visible residual traces, fatty substances of natures as different as the fatty substances CGl,
• COMPOSITION 7 presents, contrary to expectations, better degreasing performance than those of COMPOSITIONS 4 and 5, while it is based on a mixture of DMI and LE. It is the same for COMPOSITION 6 which proves to be more efficient than COMPOSITION 3 or COMPOSITION 5.
• COMPOSITIONS ⁇ and 7 according to the invention are particularly interesting products for use in degreasing because of their rinsability to water, their safety of use, their biodegradability, their renewable origin and their degreasing efficiency vis-à-vis types of fats and oils very varied and usually used in the metal processing industry. They can advantageously replace in this function the toxic chlorinated solvents and dangerous to health that are TCE or DCM, or terpene compounds such as DP and lactates such as the LE whose flash points are generally considered to be insufficiently high to avoid the risk of explosion.
• EXAMPLE 2 Film-forming compositions based on latex.
• COMPOSITION A 2,2,4-trimethyl-1-3-pentanediol monoisobutyrate, as sold by the Company PERSTORB 0X0 under the designation NEXCOAT® 795 and commonly used as a coalescing agent.
• This product is a glycol ether derivative.
• COMPOSITION B butyl ester mixture of glutaric, succinic and adipic acids as marketed by INVISTA under the designation DBE-IB®.
• COMPOSITION C dimethylisosorbide (DMI) prepared by the Applicant in the form of a colorless, odorless, low viscosity solution with a DMI purity of about 99.6%.
• DMI dimethylisosorbide
• COMPOSITION D mixture in equal parts by weight of COMPOSITION A (NEXCOAT® 795) and COMPOSITION C
• COMPOSITION E mixture in equal parts, by weight, of COMPOSITION B (DBE - IB (D) and COMPOSITION C (DMI).
• the latex used consists a dispersion in water of styrene / acrylic ester copolymer, marketed by CRAYVALLEY under the name CRAYMUL® 2423.
• the viscosity of the latex at 1 day (“VISC 1”) and at 7 days (“VISC 7”) corresponds to a Brookfield viscosity (20 ° C., 20 rpm). It is expressed here in thousands of millipascals. seconds (10 3 mPa.s).
• HOM homogeneity characteristics
• VISC 1 VISC 7 HOM HAZE TG
• COMPOSITIONS A or B have a very high viscosity and a gelled structure, thus losing all ability to be easily pumpable and dosable.
• This fluidization advantageously makes it possible to prepare more concentrated latexes and derived compositions (aqueous paints, inks, coating colors) requiring a reduced drying time.
• COMPOSITIONS D and E do not significantly alter the viscosity of the latex nor its rheological evolution over time.
• the films obtained from COMPOSITION C are of general quality improved compared to control films.
• the films obtained from COMPOSITIONS D and E, according to the invention are also of general quality even higher (homogeneous films, not cracked, values of "HAZE” relatively low), this quality can be connected, at least in part , at the "TG” values measured, which are remarkably lowered and could not be imagined with regard to the values obtained, inter alia, with the DMI alone (COMPOSITION C) on the one hand and with each of the "NEXCOAT® 755" products ( COMPOSITION A) or "DBE - IB ®” (COMPOSITION B) on the other hand.
• compositions according to the invention may be advantageously used in the preparation of aqueous paints, varnishes, lacquers, glues, stains, inks, coating colors or more generally any compositions, in particular film-forming or coating, based on latex.
• DMI dianhydrohexitol ether
• a compound B such as a glycol ether derivative or a mixture of non-fatty polyacid esters
• compositions that can be used according to the invention make it possible to prepare matt or satin aqueous paints with the possibility of total replacement of the coalescence agents normally used, such as glycol ethers.
• EXAMPLE 3 Concentrated liquid composition for machining fluid of very high biodegradability.
• An emulsion is prepared from a composition essentially containing, by weight: 25% water, 30.8% of rapeseed oil methyl esters marketed by the company NOVANCE under the tradename LUBRISORB® 926 65 (compound B ), 16.3% of a dimethylisosorbide (DMI) composition prepared by the Applicant and described in the above EXAMPLES (compound A), 15.4% of ⁇ cyclodextrin as marketed by the Applicant under the trademark KLEPTOSE®, 10% inhibitors corrosion and 1.5% surfactants, derived from sorbitan.
• DMI dimethylisosorbide
• Said emulsion is prepared by mixing, on a colloidal mill, an aqueous phase consisting of water, ⁇ -cyclodextrin and a part of the surfactants and an oily phase consisting of the other aforementioned ingredients including the esters. rapeseed oil and DMI.
• the emulsion thus obtained is weakly viscous, easily dilutable with water, stable in time, safe because it does not contain products such as diethylene glycol ethers usually used in this type of formulation to adjust the viscosity and physical stability, and non-corrosive vis-à-vis steel in particular. It also has good lubricating properties and good surface wetting properties provided by both the rapeseed oil methyl esters and the DMI. Finally, it contains essentially only highly biodegradable and renewable products, which makes it removable by simple and non-polluting processes.
• EXAMPLE 4 Cleaning compositions of a glass material.
• compositions usable according to the invention in the treatment of a glass material and more particularly as solvents in the cleaning of glass plates soiled by a bitumen composition.
• bitumen of the "70/100" type supplied by the EUROVIA Company, melted, is spread in a film about 0.5 to 1 mm thick on the glass plate.
• bitumen thus spread is at ambient temperature, cotton pieces which are impregnated with the solvent compound to be tested are deposited thereon.
• the cotton is covered with a glass bell to limit the evaporation of the solvent.
• compositions are evaluated according to two tests, namely:
• TEST 1 and TEST 2 were subjected to the following different compositions:
• COMPOSITION T2 control: mixture of 65% by weight of COMPOSITION T1 (gas oil) and 35% by weight of a dimethylisosorbide composition (DMI) prepared by the Applicant and described in the preceding Examples (compound A),
• COMPOSITION A mixture of 50% by weight of dipentene marketed by FLUKA (compound B) and 50% by weight of a dimethylisosorbide (DMI) composition prepared by the Applicant and described in EXAMPLES precedents (compound A),
• COMPOSITION B (according to the invention): mixture of 25% by weight of d-limonene sold by the company Prodasynthe (compound B) and 75% by weight of a dimethylisosorbide composition
• COMPOSITIONS A and B which can be used in accordance with the invention, can advantageously be used as solvents, including co-solvents, for the treatment of a glass material, for example for cleaning glass. 'a glass material contaminated with bitumen.
• compositions are generally more effective than a composition based on diesel (Tl) or a composition combining diesel fuel and DMI (T2).
• Tl diesel
• T2 diesel fuel
• T2 diesel fuel

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Dispersion Chemistry (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Application Of Or Painting With Fluid Materials (AREA)
• Chemical And Physical Treatments For Wood And The Like (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Chemical Treatment Of Metals (AREA)
• Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)

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• 2005
  • 2005-05-12 FR FR0504780A patent/FR2885536B1/fr not_active Expired - Fee Related
• 2006
  • 2006-05-10 US US11/914,236 patent/US20080191164A1/en not_active Abandoned
  • 2006-05-10 JP JP2008510612A patent/JP5086245B2/ja active Active
  • 2006-05-10 US US11/914,235 patent/US8080115B2/en active Active
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  • 2006-05-10 DE DE602006005641T patent/DE602006005641D1/de active Active
  • 2006-05-10 JP JP2008510611A patent/JP5373391B2/ja active Active
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