EP0998448A1 - N-alkyl-hydroxybenzylamine, verfahren zu deren herstellung, deren verwendungen und deren zusammensetzungen - Google Patents

N-alkyl-hydroxybenzylamine, verfahren zu deren herstellung, deren verwendungen und deren zusammensetzungen

Info

Publication number
EP0998448A1
EP0998448A1 EP98940319A EP98940319A EP0998448A1 EP 0998448 A1 EP0998448 A1 EP 0998448A1 EP 98940319 A EP98940319 A EP 98940319A EP 98940319 A EP98940319 A EP 98940319A EP 0998448 A1 EP0998448 A1 EP 0998448A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
hydrogen atom
composition
formula
hydroxybenzylamines
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.)
Withdrawn
Application number
EP98940319A
Other languages
English (en)
French (fr)
Inventor
Joseph Schapira
Jean-Claude Cheminaud
Patrick Droniou
Jean-Jacques Gasse
Michèle Guimon
Jo[L Bonnin
Stéphane GAGNEPAIN
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.)
Henkel AG and Co KGaA
Original Assignee
Compagnie Francaise de Produits Industriels SA
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 Compagnie Francaise de Produits Industriels SA filed Critical Compagnie Francaise de Produits Industriels SA
Publication of EP0998448A1 publication Critical patent/EP0998448A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/74Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C215/76Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
    • C07C215/80Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08Anti-corrosive paints
    • C09D5/082Anti-corrosive paints characterised by the anti-corrosive pigment
    • C09D5/086Organic or non-macromolecular compounds
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14Nitrogen-containing compounds
    • C23F11/141Amines; Quaternary ammonium compounds
    • C23F11/142Hydroxy amines

Definitions

  • the subject of the invention is new N-alkyl-hydroxybenzylamines.
  • R 1 and R 2 which are identical or different from each other, represent a hydrogen atom or a C 1 to C 8 alkyl radical mono- or polyhydroxyl, R 1 and R 2 cannot represent simultaneously each a hydrogen atom,
  • - Q represents a radical -OH or -NH 2
  • - Z represents a hydrogen atom or the group
  • R j _ and R 2 have the meanings indicated above and
  • - Y 1 and Y 2 represent a hydrogen atom or the radical -OH, Y ⁇ _ and Y cannot each simultaneously represent a hydrogen atom.
  • the molecules of formula (I) have a very strong affinity for metallic surfaces; this affinity is due to their chelating power; these molecules form a covering network on the metal surfaces, promoting both the adhesion of a coating and that of a protective paint; moreover and this is their main function, they avoid any corrosion by oxidation of the support.
  • the invention therefore also relates to the use of N-alkyl-hydroxybenzylamines of formula (I) in the treatment of metallic surfaces both against corrosion and in favor of a subsequent improvement in adhesion of paints .
  • these molecules are both reducing and chelating iron; they therefore limit the metal oxidation of the support and more particularly the oxidation of Fe (0) to Fe (II) and Fe (III). They therefore advantageously replace the known polymer structures which still have the drawback of being poorly defined. In addition, these molecules do not degrade the metal support by chemical attack; they therefore preserve the integrity of the part comprising the treated surface.
  • the above-mentioned condensation reaction can be carried out in the presence of an inert organic solvent.
  • the inert organic solvent can be advantageously chosen from aliphatic essences from the group comprising hexane, heptane, octane, nonane and dodecane, from the chlorinated derivatives of the group comprising dichloromethane, 1, 2-dichloroethane, chloroform, trichlorethylene and tetrachlorethylene, among the dialkyl ethers of the group comprising diethyl- and dipropyl ethers as well as dibutyl ethers, among polyalkoxy-alkanes, polyalkoxy -alcohols and alcohols, the preferred solvents being benzene, toluene and xylene.
  • the amount of solvent used in the reaction is not critical.
  • the reaction is carried out in the presence of a solvent forming a hetero-azeotrope with water at reflux of this azeotrope; thus, the water formed by the reaction is subtracted from the reaction medium as it is formed. This technique provides increased productivity and conversion.
  • the reaction is carried out at temperatures from 50 to 200 ° C, preferably from 50 to 150 ° C and even more preferably from 50 to 100 ° C.
  • the molar quantities of formaldehyde used relative to the amine of formula (II) can vary in the ratios from 0.1 to 5; is preferably used an amount of formaldehyde between 0.5 and 2.5 mol / mol of amino of formula (II) and, more preferably, 1 to 2 mol / mol.
  • the molar amounts of phenol of formula (III) used relative to the amine of formula (II) can vary in the ratios from 0.1 to 2; preferably a quantity of phenol of 0.4 to 1.5 mol / mol of amine is used and, more preferably still, of 0.5 to 1 mol / mol.
  • the reaction can be carried out in the absence of catalyst or in the presence of catalysts; preferably, the operation is carried out in the presence of a basic catalyst which can be chosen from aliphatic tertiary amines such as trimethylamine, methyldiethylamine or triethylamine, tertiary anilines such as dimethylaniline, diethylaniline or cyclic amines such as pyridine or imidazoles; it is also possible to use alkaline bases such as soda, potash or lime.
  • the amount of catalyst used relative to the amine of formula (II) is from 0.1% to 5% -mol of catalyst per mol of amine.
  • reaction conditions are maintained for a time necessary and sufficient to reach a conversion rate of the amine greater than 95%.
  • the N-alkyl-hydroxybenzylamines in accordance with the invention can be used in the form of corrosion protection compositions in processes which do not require chromic treatment.
  • the corrosion inhibiting composition according to the invention is characterized in that it comprises an effective amount of at least one N-alkyl-hydroxybenzylamine of formula (I) in solution or in the form of a dispersion in water or in a solvent optionally in the presence of surfactants, wetting agents and dispersants necessary for the formulation of the active material.
  • composition according to the invention contains from 0.01 to 400 g, preferably from 0.2 at 100 g per liter of active ingredient.
  • composition in accordance with the invention can be sold in the form of a concentrate.
  • the active ingredient content of the concentrate is at most that of its limit solubility in the solvent used.
  • the content in question can reach 50% by weight, that is to say 500 g / 1 of solvent or water.
  • the concentrate is diluted with the necessary amount of solvent or water.
  • Water is preferred as solvent for the composition in accordance with the invention, but it is also possible to use aliphatic essences, aromatic solvents such as benzene, toluene, xylene and alkylnaphthalene, halogenated solvents, alcohols, ethers, polyethers, ketones and mixtures of these solvents. As indicated above, exclusively aqueous formulations are preferred.
  • the pH of the composition according to the invention is from 1 to 12, preferably from 4 to 9, and even more preferably from 5 to 8.
  • an organic or mineral acid is used and, preferably, a couple of acids, one of which is organic and the other mineral; the precise adjustment of the pH of the composition is carried out by the addition of small amounts of mineral or organic bases.
  • mineral acids mention may be made of hydrochloric acid, sulfuric acid, phosphorous acid, nitric acid, sulfamic acid and phosphoric acid.
  • the components of the "organic acid - mineral acid” couple as well as the pH are chosen so as to obtain the optimum corrosion protection performance.
  • the base used to adjust the pH with precision is preferably chosen from alkylamines from the group comprising diethylamine, isopropylamine, ethylene diamine, diethylenetriamine, triethylene tetramine, hexamethylene tetramine, amines with OH function of the group comprising hydroxylamine, mono- and poly-ethanolamines, isopropanolamines, morpholine, ammonium carbonate, ammonia, soda and potash.
  • composition in accordance with the invention may contain any other compound known to a person skilled in the art from the group comprising other corrosion inhibitors, adhesion promoters, dispersants, wetting agents, emulsifiers, thickeners, anti products - foam, plasticizers, anti-freeze products, fungicidal products, bactericidal products, soluble or insoluble resins, organic polymers, pigments, dyes and mineral fillers.
  • adhesion promoters which can be used, mention may be made of silanes, organo-titanates, zircoaluminate complexes of the type sold under the brand MANCHEM®.
  • acrylic resins there may be mentioned acrylic resins, chlorinated vinyl-acrylic copolymers and phenolic resins modified by Mannich reaction.
  • fillers and pigments which can be used, mention may be made of silicas, silicates and silicoaluminates.
  • composition in accordance with the invention can be used in the context of a process successively comprising:
  • a step of rinsing the part to be treated a step of treatment using the composition according to the invention by immersing the part in the composition, by spraying the composition on the surface of the part to be treated , or by application with a brush or an ink roller, at a temperature of 15 to 60 ° C, preferably from 15 to 40 ° C, optionally a step of rinsing with possibly hot water, a step of drying at a temperature of 40 to 160 ° C.
  • a liquid or powder paint can then be applied by any paint application technique known to those skilled in the art.
  • the duration of immersion must be sufficient to lead to a uniform deposition of active material, it is generally less than 15 minutes and often between 30 and 180 seconds; the deposit thus obtained corresponds to a layer weight of the order of 0.5 to 15 g / m 2 , or in active material from 0.1 to 15 gm 2 of treated surface.
  • the temperature of the mixture is brought to 70 ° C., then 12.5 g (150 mmol) of 36% formaldehyde are introduced over 15 minutes.
  • the aqueous phase which is stripped is collected (trade term for designating the entrainment of traces of solvent by distillation) in order to remove the residual traces of solvent.
  • N-methyl-N- (1-deoxy-glucitol) 3 4-dihydroxyphenylmethylamine, N-methyl-N- (1-deoxy-glucitol) 2, 3-dihydroxyphenylmethylamine, which corresponds to a yield of 94%.
  • This active material solution is directly usable for the formulation of a corrosion inhibiting composition.
  • the mixture is heated to total reflux for 1 hour, then azeotropically distilled, in 2 hours, an amount of 10.2 g of water (ie 100% of the theoretical amount). Then introduced by the dropping funnel 100 g of distilled water, then allowed to settle for 15 minutes at 70 ° C.
  • the aqueous phase which is stripped is collected in order to eliminate the residual traces of solvent.
  • This active material solution is directly usable for the formulation of a corrosion inhibiting composition.
  • the temperature of the mixture is brought to 70 ° C., then 11.7 g (140 mmol) of 36% formaldehyde are introduced over 15 minutes.
  • the mixture is heated to total reflux for 1 hour, then azeotropically distilled, over 2 hours, an amount of 9.4 g of water (ie 98% of the theoretical amount).
  • the aqueous phase which is stripped is collected in order to eliminate the residual traces of solvent.
  • This active material solution is directly usable for the formulation of a corrosion inhibiting composition.
  • toluene 100 g of toluene, 200 g are charged into a 1 l reactor, equipped with an agitator, a thermometer, a reflux condenser, a "dean-stark” and a dropping funnel.
  • n-butanol 25.2 g (200 mmol) of pyrogallol, 46.8 g of N-methyl-glucamine (240 mmol) and 1.6 g (20 mmol) of 50% sodium hydroxide.
  • the temperature of the mixture is brought to 70 ° C., then 25.0 g (300 mmol) of 36% formaldehyde are introduced over 15 minutes.
  • 100 g of toluene 100 g are charged into a 500 ml reactor equipped with an agitator, a thermometer, a reflux condenser, a "deanstark” and a dropping funnel.
  • n-butanol 22 g (200 mmol) of pyrocatechol, 18 g of 2- (methylamino) -ethanol (240 mmol) and 1.6 g (20 mmol) of 50% sodium hydroxide.
  • the temperature of the mixture is brought to 70 ° C., then 25 g (300 mmol) of 36% formaldehyde are introduced over 15 minutes.
  • the mixture is heated to total reflux for 1 hour, then a quantity of 21.6 g of water is distilled azeotropically over 2 hours.
  • the aqueous phase which is stripped is collected in order to eliminate the residual traces of solvent.
  • This active material solution is directly usable for the formulation of a corrosion inhibiting composition.
  • the effectiveness of the N-alkyl-hydroxybenzylamines in accordance with the invention is illustrated for the inhibition of corrosion of metal surfaces.
  • the N-alkyl-hydroxybenzylamines in accordance with the invention according to examples 1 to 3 and a molecule of the prior art are used in a process the steps of which are identified in Table I by indication of the products used implementation, duration, temperature and embodiment.
  • compositions used are as indicated below: Composition A1 according to the invention: adipic acid 0.5 g / 1 phosphoric acid 0.4 g / 1 molecule of example 1 1 g / 1 sodium hydroxide 0.15 g / 1 triethylene tetramine qs pH 6, 0
  • composition A2 according to the invention:
  • composition A3 according to the invention:
  • composition Cl according to the invention:
  • the RIDOLINE 417 CF and RIDOSOL 161 CF products are degreasing compositions based on alkaline derivatives and surfactants sold by the Applicant Company.
  • the method is applied to two types of test pieces, one made of cold-rolled mild steel 0.7 mm thick and of ZES quality NFA 36.401 and the other made of zinc-coated mild steel of equal thickness. at 0.7 mm and of NFA 36.260 quality marked EZ.
  • test pieces are in the form of panels, the width and length of which are 10 and 20 cm respectively.
  • test pieces were subjected to a conventional phosphating treatment with chromic post-rinsing, the test pieces being treated according to a standard range of amorphous phosphating, the steps being: - degreasing using DURIDINE F 775 CF 1% v / v +
  • the DURIDINE F 775 CF and RIDOSOL 162 CF products which are respectively aqueous solutions based on phosphoric acid and surfactants, are marketed by the Applicant Company.
  • the corrosion resistance is determined by the salt spray test according to ISO Standard 9227. In the context of this test, the specimens are made to have an inverted V-shaped wound.
  • the adhesion of a paint is determined by the evaluation of the resistance to the grid according to Standard NFT 30.038.
  • the results are noted from 0 to 5.
  • the 0 rating corresponds to excellent adhesion without any peeling and the 5 rating to a complete peeling of the paint.
  • compositions based on the molecules in accordance with the invention give, on the one hand, better results than the molecules of the prior art comprising a phenol molecule in their structure and, on the other hand, results in all respects comparable to conventional phosphating techniques without having the drawback of requiring chromic post-rinsing.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Paints Or Removers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP98940319A 1997-07-25 1998-07-23 N-alkyl-hydroxybenzylamine, verfahren zu deren herstellung, deren verwendungen und deren zusammensetzungen Withdrawn EP0998448A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9709503 1997-07-25
FR9709503A FR2766483A1 (fr) 1997-07-25 1997-07-25 Nouvelles n-alkyl-hydroxybenzylamines, leur procede de preparation, leurs applications et compositions les contenant
PCT/FR1998/001629 WO1999005089A1 (fr) 1997-07-25 1998-07-23 Nouvelles n-alkyl-hydroxybenzylamines, leur procede de preparation, leurs applications et compositions les contenant

Publications (1)

Publication Number Publication Date
EP0998448A1 true EP0998448A1 (de) 2000-05-10

Family

ID=9509643

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98940319A Withdrawn EP0998448A1 (de) 1997-07-25 1998-07-23 N-alkyl-hydroxybenzylamine, verfahren zu deren herstellung, deren verwendungen und deren zusammensetzungen

Country Status (5)

Country Link
EP (1) EP0998448A1 (de)
JP (1) JP2001510820A (de)
CA (1) CA2297803A1 (de)
FR (1) FR2766483A1 (de)
WO (1) WO1999005089A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7345031B2 (en) * 2000-04-12 2008-03-18 International Medical Innovations, Inc. Pharmaceutical dopamine glycoconjugate compositions and methods of their preparation and use
US20060189547A1 (en) 2000-04-12 2006-08-24 Christian Samuel T Novel pharmaceutical agents containing carbohydrate moieties and methods of their preparation and use
US9302982B2 (en) 2000-04-12 2016-04-05 Glycon Llc Pharmaceutical dopamine glycoconjugate compositions and methods of their preparation and use
CN115233225A (zh) * 2022-07-25 2022-10-25 威海翔宇环保科技股份有限公司 两性环境友好型高温缓蚀剂及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2802820A (en) * 1953-02-18 1957-08-13 Atlas Powder Co Condensation products of secondary hexityl amines, formaldehyde and phenols
GB9108222D0 (en) * 1991-04-17 1991-06-05 Ici Plc Composition and method

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9905089A1 *

Also Published As

Publication number Publication date
FR2766483A1 (fr) 1999-01-29
JP2001510820A (ja) 2001-08-07
WO1999005089A1 (fr) 1999-02-04
CA2297803A1 (fr) 1999-02-04

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