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
  • C09D9/00—Chemical paint or ink removers
  • C09D9/005—Chemical paint or ink removers containing organic solvents

Definitions

• the present invention relates to the use in anti-graffiti treatments, preferably in graffiti removal treatments, of a diester of a particular dicarboxylic acid, which provides improved processing efficiency.
• the graffiti removal treatments are generally carried out by cleaning with a liquid composition comprising a solvent.
• fluorinated latex polymers For prior treatments, the use of fluorinated latex polymers is particularly known. A product comprising such polymers, intended to be applied to building materials, is in particular marketed under the name Protectguard®. The use of other products is also known. Solvents are sometimes used as additives in the pretreatments.
• a linear dicarboxylic acid diester solvent especially a solvent comprising a mixture of dimethyl adipate, dimethyl glutarate, and dimethyl succinate
• Rhodiasolv® RPDE a solvent comprising a mixture of dimethyl adipate, dimethyl glutarate, and dimethyl succinate
• the present invention satisfies this need by proposing the use in anti-graffiti treatments of a product comprising a diester of a dicarboxylic acid of formula (I):
• R 1 and R 2 which may be identical or different, represent a linear or branched, cyclic or non-cyclic alkyl, aryl, alkylaryl or arylalkyl group,
• group A represents a divalent alkylene group, characterized in that the product comprises at least one diester of a dicarboxylic acid in which group A is a divalent alkylene group connected to C 3 -C 10 .
• the dicarboxylic acid diester of the invention provides the treatment with improved efficiency.
• the effectiveness can be qualified by the traces of graffiti remaining after a delete operation.
• the improvement may notably be of one of the following natures:
• the invention also relates to anti-graffiti treatment methods comprising a step where a product comprising the diester of the invention is applied.
• the invention also relates to an anti-graffiti treatment composition comprising the product comprising the diester of the invention.
• the treatment uses a product comprising a diester of a particular dicarboxylic acid of the formula (I) of which the group A is connected.
• this diester of a dicarboxylic acid may be referred to as a "special diester", "diester of the invention", or "connected diester".
• the product comprises at least one connected diester. He can understand two or more.
• "a" branched diester may designate a single branched diester corresponding to formula (I) or a mixture or combination of several branched diesters having the formula (I).
• the product may comprise other compounds than the diester of the invention.
• the product preferably comprises at least 50% by weight, preferably at least 60%, preferably at least 70%, preferably at least 80%, preferably at least 90%, of the diester of the invention, relative to the total quantity of the product, preferably in relation to total amount of diester type dicarboxylic acid compounds present in the product.
• Group A is a divalent divalent alkylene group.
• the corresponding acid is the compound of formula HOOC-A-COOH.
• the group A can in particular be a C 4 , C 5 , C 6 , C 7 , C 8 or C 9 group , or a mixture. It is preferably a C 6 group .
• the group A is preferably chosen from the following groups: the group A M G of formula -CH (CH 3 ) -CH 2 -CH 2 -, (corresponding to 2-methylglutaric acid)
• the groups R 1 and R 2 which may be identical or different, may especially be chosen from methyl, ethyl, n-propyl, isopropyl, benzyl, phenyl, n-butyl, isobutyl, cyclohexyl, hexyl, n-hexyl and isooctyl groups. -éthylhexyle. They correspond to the alcohols of formulas R 1 -OH and R 2 -OH, which are identical or different.
• the product may advantageously comprise dimethyl of 2-methylglutaric acid, the following formula:
• the product is a composition comprising the dicarboxylic acid diesters of formulas (T), (I ”) and optionally (II) below:
• R 1 -OOC- (CH 2) 4 -COO-R 2 (II) diester of adipic acid
• - MG is a group of formula -CH (CH 3 ) -CH 2 -CH 2 -
• E s is a group of formula -CH (C 2 H 5 ) -CH 2 -.
• the groups R 1 and R 2 can in particular be methyl, ethyl or isobutyl groups.
• a preferred composition comprises: from 70 to 95% by weight of the dicarboxylic acid diester of formula (I 1 ), preferably methyl diester, from 5 to 30% by weight of the dicarboxylic acid diester of formula (I "), preferably methyl diester, and
• the diester of the invention can be obtained by any known process leading to diesters, in particular by reaction of an alcohol corresponding to the groups R 1 and R 2 with a dicarboxylic acid corresponding to group A or di (acyl chloride) of the formula CIOC-A-COCI or a corresponding dinitrile of formula NC-A-CN.
• the product comprises several diesters of dicarboxylic acids, for example the diesters of formula (I 1 ), (I ") and optionally (II)
• the same type of reaction can be carried out from a mixture corresponding dicarboxylic acids or acyl chlorides or dinitriles.
• compositions comprising the diester (s) can in particular be obtained from a mixture of dinitrile compounds in particular produced and recovered in the process for producing adiponitrile by double hydrocyanation of butadiene.
• This process widely used in industry to produce the vast majority of adiponitrile consumed worldwide, is described in numerous patents and publications.
• the hydrocyanation reaction of butadiene leads mainly to the formation of linear dinitriles but also to a formation of branched dinitriles, the two main ones are methylglutaronitrile and ethylsuccinonitrile.
• the branched dinitrile compounds are separated by distillation and recovered, for example, as a top fraction in a distillation column.
• the mixture of branched dinitrile compounds is converted into diesters to thereby obtain a new solvent.
• the diesters of the invention can also be obtained by a reaction between the dinitrile compounds, water and an alcohol in the gas phase and in the presence of a solid catalyst.
• the reaction temperature is advantageously greater than the condensation temperature of the diesters formed.
• an acidic solid catalyst such as, for example, a silica gel, a silica-alumina mixture or boric or phosphoric acids which are supported. Macroporous aluminas such as those described in European Patent EP0805801 can also be used.
• the temperature of the reaction is between 200 and 450 ° C., preferably between 230 and 350 ° C.
• the reaction can be carried out under any pressure, advantageously between 0.1 and 20 bar. At the outlet of the reactor, the vapors are rapidly cooled to a temperature of less than or equal to 150 ° C. From the mixture obtained, ammonia is distilled off, followed by excess water and alcohol.
• the diesters of the invention can also be obtained by reaction between the dinitrile compounds and a mineral base to obtain acid salts, then neutralization of these salts with an acid followed by esterification with an alcohol.
• diesters can be purified according to the purification methods conventionally used in the technical field of the preparation of organic compounds and in particular by distillation in one or more columns.
• the anti-graffiti treatment is preferably a graffiti removal treatment present on a substrate.
• graffiti can be removed in whole or in part.
• the graffiti may in particular be ink-based graffiti, for example made using a pen, or paint-based graffiti for example made using an aerosol can, a brush or a roll.
• the substrate may in particular be a building material.
• construction material means any large element that can be found in the public sphere (interiors of buildings accessible to a large number of people including businesses, restaurants, exterior parts of buildings accessible to third, transport, floors, street furniture, etc.), as opposed to the private sphere (parts of apartments or houses not accessible to third parties).
• the substrate, preferably a building material may for example be of one of the following materials:
• a ceramic preferably a tile, for example of the type of enamelled sandstone type, a material with a hydraulic binder, preferably made of cement, a mortar, or a concrete,
• - terracotta for example bricks, tiles, tiles, or
• - stone preferably porous. It may include external surfaces such as facades, stone, balusters, cornices, statues, joints, lintels and tables of openings, siding, basements, balconies, terraces, steps, pathways and walkways, fences , planters, parking areas, driveways, garage floors, pool surrounds, fountain surrounds, barbecues, roofs, fireplaces. It may be interior surfaces of soil type; fireplace stones, countertops, tile joints, etc.
• It can especially be a porous material such as limestone, marble, sandstone, granite, slate, terracotta (tiles, bricks, tomettes), concrete, plaster (MPC), reconstituted stones, bitumen.
• a porous material such as limestone, marble, sandstone, granite, slate, terracotta (tiles, bricks, tomettes), concrete, plaster (MPC), reconstituted stones, bitumen.
• the invention is particularly advantageous for substrates made of a porous material, such as, for example, limestone, marble, sandstone, granite, slate, terracotta (tiles, bricks, tomettes), concretes, coatings (MPC), reconstituted stones , bitumen.
• a useful method of anti-graffiti treatment may include the following steps:
• a step of removing the graffiti with the aid of a suppression composition comprising the product comprising the diester of the invention.
• a liquid treatment product comprising a pretreatment agent, for example a fluorinated latex.
• a pretreatment agent for example a fluorinated latex.
• the application of the product can be carried out by any appropriate means, for example by dipping, spraying, applying a brush or a roller.
• means used in the field of painting and / or cleaning for example paint guns, or pressurized sprayers.
• the pretreatment can be applied once, or applied several times, at a chosen time interval (for example once a year).
• the removal of graffiti may be carried out with a suppressing composition comprising the product comprising the diester of the invention, preferably in liquid form.
• the suppressing composition may be the product comprising the substantially pure diester of the invention. According to one alternative, it includes the product and other compounds.
• the product may for example be diluted in water and / or in at least one other organic solvent.
• the composition may comprise additives, for example abrasives.
• the suppressing composition may be applied to the graffiti using any suitable means, for example by spraying, applying a brush or a roller, a sponge or a piece of cloth. After or during the application you can rub the graffiti to remove it.
• the spraying force may, however, be sufficient for the at least partial disappearance of the graffiti.
• the delete operation can be repeated if it is useful. Afterwards, it may optionally rinse or wash the substrate, for example to remove the resulting solute and / or to eliminate any run-off.
• the 100% complement corresponds to the impurities present in this mixture, which are generally not dinitrile compounds.
• the dinitrile / methanol compound mixture is cooled to about 1 ° C before the addition of
• the reaction medium is heated to reflux and maintained at this temperature for
• reaction mass is heterogeneous and fluid. After cooling to 60 ° C., 63 g of water are added. The reaction medium is maintained at 65 ° C. for 2 hours.
• reaction medium becomes biphasic.
• the two phases are decanted and analyzed.
• the recovered organic phase is washed with a saturated aqueous solution of sodium chloride with addition of ammonia to obtain a pH in the region of 7.
• Example 2 Treatments Pretreatment: - Protectguard®, marketed by Guard Industrie, distributed in Point P stores
• Paint simulating graffiti - Fluorescent orange aerosol paint, "Orange Fluo TP", marketed by Soppec, distributed in Point P stores.
• the note is postponed with different prior treatments and different suppression compositions.
• Example 1 has a very significant efficiency in ammonia refinery.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 2007
  • 2007-05-07 FR FR0703282A patent/FR2915997B1/fr active Active
• 2008
  • 2008-04-25 US US12/599,256 patent/US8137475B2/en not_active Expired - Fee Related
  • 2008-04-25 EP EP08736572A patent/EP2144970A1/de not_active Withdrawn
  • 2008-04-25 WO PCT/EP2008/055050 patent/WO2008135409A1/fr active Application Filing

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