FR2792949A1 - NON-POLLUTING REACTIVE COMPOUND FOR COATING METALS TO PROTECT THEM FROM CORROSION AND TO FACILITATE THEIR MECHANICAL DEFORMATION - Google Patents
NON-POLLUTING REACTIVE COMPOUND FOR COATING METALS TO PROTECT THEM FROM CORROSION AND TO FACILITATE THEIR MECHANICAL DEFORMATION Download PDFInfo
- Publication number
- FR2792949A1 FR2792949A1 FR9905554A FR9905554A FR2792949A1 FR 2792949 A1 FR2792949 A1 FR 2792949A1 FR 9905554 A FR9905554 A FR 9905554A FR 9905554 A FR9905554 A FR 9905554A FR 2792949 A1 FR2792949 A1 FR 2792949A1
- Authority
- FR
- France
- Prior art keywords
- composition according
- binder
- additive
- sep
- composition
- 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.)
- Granted
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- 0 *CC(C1C2CC2)[C@@]1N Chemical compound *CC(C1C2CC2)[C@@]1N 0.000 description 1
Classifications
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- 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
- C09D5/08—Anti-corrosive paints
- C09D5/12—Wash primers
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M103/00—Lubricating compositions characterised by the base-material being an inorganic material
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- C10M103/00—Lubricating compositions characterised by the base-material being an inorganic material
- C10M103/02—Carbon; Graphite
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- C10M103/00—Lubricating compositions characterised by the base-material being an inorganic material
- C10M103/06—Metal compounds
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Abstract
Description
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Composé réactif non polluant pour le revêtement de métaux, en vue de les protéger de la corrosion et de faciliter leur déformation mécanique Pour assurer une utilisation rationnelle des métaux et alliages et permettre la fabrication de pièces métalliques d'usage, il est nécessaire de procéder à des opérations de mise en forme, qui, selon la destination des pièces produites, pourront être réalisées, selon les techniques connues, essentiellement selon deux voies : # Un usinage qui consiste à retirer de la matière d'une pièce brute, venue de fonderie, de moulage ou de prélèvement sur une pièce plus volumineuse, usinage opéré par tournage, fraisage, rabotage, filetage, taraudage, etc.. Non-polluting reactive compound for the coating of metals, in order to protect them from corrosion and to facilitate their mechanical deformation To ensure the rational use of metals and alloys and to allow the manufacture of metal parts for use, it is necessary to carry out formatting operations, which, according to the destination of the parts produced, can be realized, according to known techniques, essentially in two ways: # A machining which consists in removing material from a raw part, coming from a foundry, molding or sampling on a larger part, machining performed by turning, milling, planing, threading, tapping, etc.
Toutes ces méthodes conduisent à un enlèvement de métal, parce qu'elles sont réalisées à l'aide d'outils de coupe, avec production de copeaux, c'est-à-dire de déchets. All these methods lead to metal removal, because they are made using cutting tools, with production of chips, that is to say waste.
# Un traitement mécanique, qui fait appel aux propriétés de plasticité, de déformabilité, que tous les matériaux métalliques présentent à des degrés divers, ce traitement étant réalisé par déformation d'une ébauche, qui n'exige pas d'enlèvement de métal et qui est conduite en une ou plusieurs opérations progressives de mise en forme. # A mechanical treatment, which uses the properties of plasticity, of deformability, that all metal materials have to varying degrees, this treatment being achieved by deformation of a blank, which does not require metal removal and which is conducted in one or more progressive formatting operations.
La pièce subit des pressions élevées sur les parties déformées, pressions qui provoquent simultanément une élévation locale de température qui améliore l'aptitude à la déformation du métal mis en oeuvre. On oblige ainsi la pièce à épouser les conformations désirées, au moyen d'outillages spécifiques, tels que filières, poinçons ou bien outils matriciels divers. The part undergoes high pressures on the deformed parts, pressures which simultaneously cause a local rise in temperature which improves the deformability of the metal used. This requires the piece to marry the desired conformations, by means of specific tools, such as dies, punches or various matrix tools.
La technique de mise en forme non par usinage mais par déformation concerne les plus grandes quantités de métaux et alliages, pour la confection d'un nombre incalculable de pièces métalliques. The technique of shaping not by machining but by deformation concerns the largest quantities of metals and alloys, for the making of an incalculable number of metal parts.
On peut citer, par exemple, les opérations de laminage, d'étirage, de tréfilage, d'extrusion, d'emboutissage, de forgeage, de frappe, etc. mais, quel que soit son type, il est toujours nécessaire de faciliter au mieux le travail effectué dans la zone d'interaction entre la pièce et l'outil, qu'il s'agisse de cylindres, dans le cas du laminage, de filières dans le cas de l'étirage ou du tréfilage, de poinçons dans le cas de l'emboutissage, de matrices dans le cas de la frappe. Examples include rolling, drawing, drawing, extruding, stamping, forging, coining, etc. but, whatever its type, it is always necessary to facilitate as well as possible the work done in the zone of interaction between the part and the tool, whether it is cylinders, in the case of rolling, of dies in the case of drawing or drawing, punches in the case of stamping, dies in the case of striking.
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Pour faciliter le travail, il faut disposer d'une interface pièce/outil de déformation, capable d'éliminer les risques de grippage, d'arrachement de métal ou de soudures, étant donné les valeurs très importantes de pression et de température atteintes localement. To facilitate the work, it is necessary to have an interface piece / deformation tool, able to eliminate the risks of jamming, tearing of metal or welds, given the very important values of pressure and temperature reached locally.
Il est donc nécessaire de refroidir l'outillage, bien que les températures atteintes soient fortement conditionnées par la nature et l'adéquation du lubrifiant à la déformation. It is therefore necessary to cool the tools, although the temperatures reached are strongly conditioned by the nature and the suitability of the lubricant for deformation.
Ce lubrifiant doit supporter, sans décomposition, des températures voisines de 400 C, résister à l'oxydation et posséder des qualités compatibles avec les pressions extrêmes auxquelles il est soumis, le travail s'effectuant toujours en régime de lubrification limite. This lubricant must withstand, without decomposition, temperatures close to 400 C, withstand oxidation and have qualities compatible with the extreme pressures to which it is subjected, the work is always carried out under limited lubrication regime.
Il devra aussi améliorer la "glissance " entre le métal déformé et l'outil, ce qui se traduit par de faibles valeurs des coefficients de friction statique et dynamique. It will also improve the "slip" between the deformed metal and the tool, which results in low values of static and dynamic coefficients of friction.
Si ces propriétés apparaissent comme étant le minimum exigible, il faut, en outre, que le lubrifiant soit conçu de telle manière qu'il adhère très fortement au métal à déformer, pour éviter le risque de rupture du film lubrifiant. On comprend, en effet, que si ce film lubrifiant était rompu par endroits, cela conduirait à se retrouver dans des conditions de frottement métal sur métal, se traduisant par des arrachements et par des soudures métal/outil, rendant l'opération impraticable. If these properties appear to be the minimum required, it must, in addition, that the lubricant is designed in such a way that it adheres very strongly to the metal to be deformed, to avoid the risk of rupture of the lubricant film. It is understood, indeed, that if this lubricant film was broken in places, it would lead to end up in metal-on-metal friction conditions, resulting in tearing and metal / tool welds, making the operation impractical.
Toutes ces propriétés réunies dans un lubrifiant destiné aux opérations de déformation plastique des métaux, permettraient la réalisation d'un travail dans des conditions de contraintes mécaniques, de pression, de glissement, de striction et de température, beaucoup moins pénalisantes que par les moyens actuellement connus. Cela devrait se traduire par une diminution des contraintes de remise à niveau de déformabilité acceptable des métaux à traiter, particulièrement des fréquences de traitements de recuits ou d'hypertrempes. Il s'ensuivrait un bilan économique significativement plus satisfaisant. All these properties combined in a lubricant for plastic deformation operations of metals, would allow the realization of work in conditions of mechanical stress, pressure, sliding, necking and temperature, much less penalizing than by the means currently known. This should result in a reduction in the acceptable deformability leveling constraints of the metals to be treated, particularly the frequencies of annealing or tempering treatments. This would result in a significantly more satisfactory economic balance sheet.
Or, à ce jour, pour réaliser les opérations de déformation plastique des métaux et alliages et pour obtenir une adhérence satisfaisante des lubrifiants utilisés, on doit procéder à des traitements chimiques des pièces à déformer, suivant une succession d'opérations distinctes. However, to date, to carry out plastic deformation operations of metals and alloys and to obtain a satisfactory adhesion of the lubricants used, one must carry out chemical treatments of the parts to be deformed, following a succession of separate operations.
Ces traitements conduisent à la formation d'un revêtement, dit de conversion, obtenu à partir de solutions acides telles que de phosphatation, ou d'oxalation dans le cas d'alliages inoxydables. These treatments lead to the formation of a so-called conversion coating obtained from acidic solutions such as phosphatation or oxalation in the case of stainless alloys.
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Les revêtements constitués par des phosphates, ou des oxalates métalliques, se présentent sous forme cristalline, bien adhérents, constituant un réseau cristallin à l'intérieur duquel les lubrifiants appliqués seront maintenus, par simple action physique, durant l'opération de déformation. On observe qu'en l'état, il n'y a pas de combinaison chimique entre le métal et le lubrifiant. Coatings consisting of phosphates, or metal oxalates, are in crystalline form, well adherent, constituting a crystal lattice within which the applied lubricants will be maintained, by simple physical action, during the deformation operation. It is observed that in the state, there is no chemical combination between the metal and the lubricant.
Ces traitements, quoique parfaitement maîtrisés, présentent un certain nombre d'inconvénients, principalement liés à leur impact sur l'environnement. These treatments, although perfectly controlled, have a number of disadvantages, mainly related to their impact on the environment.
En cours d'application, il y a production de quantités très importantes d'effluents contaminés par des métaux lourds, par des phosphates, de nature acide, grands consommateurs d'eau et d'énergie. During application, very large quantities of effluents contaminated by heavy metals, phosphates of acidic nature, large consumers of water and energy are produced.
Les solutions de traitement fortement acides occupent des volumes importants, de même qu'une emprise au sol non négligeable, avec de fortes contraintes de génie civil. The highly acidic treatment solutions occupy large volumes, as well as a significant footprint with strong civil engineering constraints.
A titre d'exemple, on peut citer les documents suivants qui illustrent l'Etat de la Technique : # GB 1 122 404 qui décrit des produits dont certains peuvent être considérés comme proches de ceux qui sont utilisés avec l'invention, mais qui ne prévoit pas la présence d'un liant filmogène et qui n'explicite aucune application évoquant de près ou de loin le problème de la déformation plastique des métaux. By way of example, mention may be made of the following documents which illustrate the state of the art: # GB 1 122 404 which describes products some of which may be considered to be close to those used with the invention, but which do not does not provide the presence of a film-forming binder and which does not imply any application remotely evoking the problem of the plastic deformation of metals.
# EP 0 704 465 qui décrit un produit anticorrosion ne contenant aucun composant lubrifiant et, à ce titre étranger à la présente invention qui concerne, précisément, une composition contenant des lubrifiants favorisant la déformation plastique des métaux. EP 0 704 465 which discloses an anticorrosive product containing no lubricating component and, as such foreign to the present invention which specifically relates to a composition containing lubricants promoting the plastic deformation of metals.
# EP 0 278 029 qui décrit des produits anticorrosion contenant des aldéhydes et du formol dont l'usage est unanimement condamné en raison des pollutions qu'ils entraînent lors de leur application et alors de leur élimination. Ils sont donc à exclure absolument et ne se retrouvent jamais dans une composition conforme à l'invention. # EP 0 278 029 which describes anti-corrosion products containing aldehydes and formaldehyde whose use is unanimously condemned because of the pollution they cause during their application and then their disposal. They are therefore absolutely excluded and are never found in a composition according to the invention.
# EP 0 376 591qui décrit exclusivement l'usage de phosphates, alors que l'invention les considère comme insuffisants à eux seuls pour les applications visées, à savoir la déformation plastique des métaux. En effet, les phosphates possèdent un atome d'oxygène en position intermédiaire qui leur donne une instabilité à l'hydrolyse non souhaitable. Which describes exclusively the use of phosphates, whereas the invention considers them as insufficient by themselves for the intended applications, namely the plastic deformation of metals. In fact, phosphates have an oxygen atom in the intermediate position which gives them undesirable instability to hydrolysis.
La présente invention permet la suppression de tous les moyens polluants, avec toutes leurs contraintes écologiques. Elle autorise la suppression des consommations d'eau et d'énergie nécessaires à l'application des procédés conventionnels. The present invention allows the removal of all polluting means, with all their ecological constraints. It allows the abolition of water and energy consumption necessary for the application of conventional processes.
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Les traitements nouveaux sont appliqués à un seul poste de travail, en une seule opération et, en outre, le produit ainsi appliqué a une tenue irréprochable autorisant les traitements mécaniques les plus contraignants, y compris la forge à froid. The new treatments are applied to a single workstation, in a single operation and, in addition, the product thus applied has an impeccable holding allowing the most demanding mechanical treatments, including cold forging.
A cette fin, l'invention a pour objet un procédé de préparations de produits métalliques destinés à être façonnés par au moins une opération mécanique de déformation plastique telle que tréfilage, laminage, calandrage, forgeage, matriçage et analogue, sans retrait significatif de substance, caractérisé en ce que l'on applique aux produits métalliques directement c'est-à-dire sans aucun traitement préalable, une composition formée, au moins, d'un liant filmogène, d'au moins un additif de réactivité avec le métal, d'au moins un additif de lubrification et d'au moins un additif anticorrosion. To this end, the subject of the invention is a method for preparing metal products intended to be shaped by at least one mechanical plastic deformation operation such as drawing, rolling, calendering, forging, stamping and the like, without significant withdrawal of substance, characterized in that directly to the metal products, ie without any prior treatment, a composition formed, at least, of a film-forming binder, of at least one reactivity additive with the metal, is applied to the metal products, at least one lubricating additive and at least one anti-corrosion additive.
Selon d'autres caractéristiques de ce procédé : # les produits métalliques à traiter ayant une surface excessivement oxydée sans pourtant être calaminée, on les soumet à un brossage grossier devant ramener l'oxydation de leur surface à une valeur faible, non nécessairement nulle, puis on leur applique la composition ; # les produits métalliques à traiter étant excessivement gras en surface, on les soumet à un nettoyage grossier devant ramener le gras de leur surface à une valeur faible, non nécessairement nulle, puis on leur applique la composition ; L'invention a également pour objet une composition devant être appliquée sur des produits métalliques destinés à être façonnés par au moins une opération mécanique de déformation plastique telle que tréfilage, laminage, calandrage, forgeage, matriçage et analogue, sans retrait significatif de substance, caractérisé en ce qu'elle comprend un liant filmogène, au moins un additif de réactivité avec le métal, au moins un additif de lubrification et au moins un additif anticorrosion. According to other characteristics of this process: the metal products to be treated having an excessively oxidized surface without being calaminated, they are subjected to a rough brushing to reduce the oxidation of their surface to a low value, not necessarily zero, then the composition is applied to them; the metal products to be treated being excessively greasy on the surface, they are subjected to a coarse cleaning in order to reduce the fat of their surface to a low value, not necessarily zero, then the composition is applied to them; The invention also relates to a composition to be applied to metal products to be shaped by at least one mechanical plastic deformation operation such as drawing, rolling, calendering, forging, stamping and the like, without significant withdrawal of substance, characterized in that it comprises a film-forming binder, at least one reactivity additive with the metal, at least one lubricating additive and at least one anti-corrosion additive.
Selon d'autres caractéristiques de cette composition : # l'additif de réactivité est un phosphonate ou un phosphate dont les chaînes moléculaires sont soit hydrocarbonées, soit fluorées, soit chlorofluorées ; # l'additif de réactivité est formé par au moins un composant sélectionné parmi : # les acides phosphoniques et alkyl phosphoniques, # les acides phosphoriques, # l'acide aminotriméthylène phosphonique, According to other characteristics of this composition: # the reactivity additive is a phosphonate or a phosphate whose molecular chains are either hydrocarbon-based, fluorinated or chlorofluorinated; the reactivity additive is formed by at least one component selected from: # phosphonic and alkyl phosphonic acids, # phosphoric acids, # aminotrimethylene phosphonic acid,
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l'acide 1- hydroxyéthylidène - 1 - 1 - diphosphonique, l'acide éthylène diamine tétraméthylène phosphonique, l'acide hexaméthylène diamine tétra méthylène phosphonique, l'acide di - éthylène triamine penteméthylène phosphonique ; # elle comprend en outre un ou plusieurs additifs de pigmentation ; # elle comprend en outre un ou plusieurs produits mouillants ; # le liant est de nature organique, oligomère, polymère ou copolymère ; # le liant est de nature organo-métallique ; # le liant est de nature lubrifiante ; # le liant est de type carboxylé tel qu'un copolymère anhydride maléique et vinyléther, styrène ou allyléther ; # le liant est de type phosphoné; # le liant est non réactif mais a une structure apte à recevoir au moins un additif lubrifiant ; # le liant est de type butyral vinylique ; # le liant est un copolymère styrène - butadiène ; # le liant est un copolymère acéto - chlorure de vinyle ; # le liant est un copolymère acrylonitrile - butadiène ; # le liant est un copolymère styrène - acrylique ; # le liant est une cire ; # l'additif de lubrification est formé par au moins un composant sélectionné parmi les suivants : # graphite, => polyfluorure de carbone (CFx)n, avec x # 1 # triphényl phosphoro thionate alkylé, => triphényl phosphoro thionate, => di - alkyl phosphites, => tri - aryl phosphites, # trifluorure de cérium (CeF3), # alkylxanthates de molybdène, 1-hydroxyethylidene-1-l-diphosphonic acid, ethylene diamine tetramethylene phosphonic acid, hexamethylene diamine tetra methylene phosphonic acid, diethylene triamine pentemethylene phosphonic acid; it further comprises one or more pigmentation additives; # it further comprises one or more wetting products; the binder is of organic nature, oligomer, polymer or copolymer; the binder is organo-metallic in nature; the binder is of a lubricating nature; the binder is of the carboxylated type such as a maleic anhydride copolymer and vinyl ether, styrene or allyl ether; the binder is of the phosphonated type; the binder is non-reactive but has a structure capable of receiving at least one lubricant additive; the binder is of the vinyl butyral type; the binder is a styrene-butadiene copolymer; the binder is an aceto vinyl chloride copolymer; the binder is an acrylonitrile-butadiene copolymer; the binder is a styrene-acrylic copolymer; # the binder is a wax; # the lubricating additive is formed by at least one component selected from the following: # graphite, => carbon polyfluoride (CFx) n, with x # 1 # triphenyl phosphoro thionate alkyl, => triphenyl phosphoro thionate, => di alkyl phosphites, tri-aryl phosphites, cerium trifluoride (CeF 3), molybdenum alkyl xanthates,
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sels d'ammonium alkyl substitués de l'acide tétrathiomolybdique (RNH3)2 - MoS4). substituted alkyl ammonium salts of tetrathiomolybdic acid (RNH3) 2 - MoS4).
# un additif de pigmentation au moins est de type réactif tel que phosphonate, molybdate et analogue ; # un additif de pigmentation au moins est de type non réactif opacifiant ; # un produit mouillant est formé par au moins un composant sélectionné parmi les suivants : # alkyl et aryl phosphonates éthoxylés, => dérivés fluorocarbonés, => sulfonate d'ammonium perfluoroalkylé, # sulfonate de potassium perfluoroalkylé, # sulfonate d'amino alcool perfluoroalkylé, => acrylate perfluoroalkylé. at least one pigmentation additive is of the reactive type such as phosphonate, molybdate and the like; # at least one pigmentation additive is non-reactive opacifying type; a wetting agent is formed by at least one component selected from the following: ## STR5 ## => perfluoroalkyl acrylate.
L'invention sera mieux comprise par la description détaillée ci-après et par le dessin annexé qui ne sont donnés qu'à titre d'exemple indicatif et non limitatif. The invention will be better understood from the detailed description below and the attached drawing which are given by way of indicative and non-limiting example.
La figure 1 est une courbe qui illustre Le liant est dans tous les cas, de nature organique, oligomère, polymère ou copolymère, ou de nature organométallique. Figure 1 is a curve which illustrates the binder is in all cases of organic nature, oligomer, polymer or copolymer, or organometallic nature.
Il peut être intrinsèquement lubrifiant ou bien être un support pour des lubrifiants de nature thermoplastique aptes à subir et à accompagner une opération de déformation tout le temps de l'application de celle-ci, et sans rupture du revêtement. It can be intrinsically lubricating or be a support for thermoplastic lubricants able to undergo and accompany a deformation operation all the time of the application thereof, and without breaking the coating.
Parmi les diverses familles de liants, on peut opter pour : 1 - Les liants non réactifs # Butyrals vinyliques. Among the various families of binders, one can opt for: 1 - Non-reactive binders # Vinyl butyrals.
Dans le commerce, on trouve de tels produits sous les noms déposés de " RHOVINALS
B " (provenant de la société RHONE-POULENC), " MOWITALS " (provenant de la société HOECHST), " BUTVAR " (provenant de la société MONSANTO) et qui ont pour formule générale : In the trade, one finds such products under the registered names of "RHOVINALS
B "(from the company RHONE-POULENC)," MOWITALS "(from the company HOECHST)," BUTVAR "(from the company MONSANTO) and whose general formula:
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avec x = 12 à 20% y = 1 à 3% j = 75 à 86% # Copolymères styrène-butadiène :
Un produit de ce type est connu dans le commerce sous le nom déposé de " EUROPREN
SOL 7172 " de la société ENITECH.
with x = 12 to 20% y = 1 to 3% j = 75 to 86% # Styrene-butadiene copolymers:
A product of this type is known commercially as "EUROPREN"
SOL 7172 "from ENITECH.
# Copolymères acéto-chlorures de vinyle :
De tels produits sont connus dans le commerce sous les noms déposés de " VINYLITES ", " VYHH ", " VYLF ", " VYNS ", VYNW ", " VYDR ", " VYNY de la société UNION CARBIDE. # Aceto-vinyl chloride copolymers:
Such products are known in the trade under the registered names of "VINYLITES", "VYHH", "VYLF", "VYNS", VYNW "," VYDR "," VYNY of the company UNION CARBIDE.
# Copolymères acrylonitrile-butadiène :
Produit de marque " HYCAR " de la société GOODRICH. # Acrylonitrile-butadiene copolymers:
"HYCAR" brand product from GOODRICH.
# Copolymères styrène-acrylique :
Produit du commerce connu sous le nom déposé de " NEOCRYL B880 ", ou " NEOCRYL B1000 " de la société ZENECA # Cires : d'origine naturelle (d'abeilles, de carnauba, etc. ) d'origine fossile (de MONTAN) d'origine pétrolière (paraffines, micro cristallines, etc.) de synthèse (amides de haut poids moléculaire : " ERUCAMIDE ", " OLEYLAMIDE ", " STEARYLAMIDE ") ou " CIRE AMIDE C " ou " CRODA " de la société HOECHST cires modifiées (chlorés de marque " CERECLOR " de la société IMPERIAL
CHEMICAL INDUSTRIES). # Styrene-acrylic copolymers:
Commercial product known as "NEOCRYL B880" or "NEOCRYL B1000" from ZENECA # Waxes: of natural origin (bees, carnauba, etc.) of fossil origin (de MONTAN) d petroleum origin (paraffins, microcrystals, etc.) of synthesis (high molecular weight amides: "ERUCAMIDE", "OLEYLAMIDE", "STEARYLAMIDE") or "AMIDE WAX C" or "CRODA" from the company HOECHST modified waxes ( chlorinated brand "CERECLOR" from the company IMPERIAL
CHEMICAL INDUSTRIES).
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2 - Les liants réactifs carboxylés # Copolymères vinyléther-anhydride maléïque par exemple le produit nommé " GANTREZ " de la société ISP. 2 - Carboxylic reactive binders # vinyl ether-maleic anhydride copolymers for example the product named "GANTREZ" from the company ISP.
# Copolymères styrène-anhydride maléïque
Par exemple, le produit nommé " SMA " de la société ATOCHEM. # Styrene-maleic anhydride copolymers
For example, the product named "SMA" of the company ATOCHEM.
# Copolymères allyle éther-anhydride maléïque
Tel que le produit connu dans le commerce sous le nom déposé de MALIALIM de la société NIPPON OIL and FATS CO. # Allyl ether-maleic anhydride copolymers
As the product known in the trade under the registered name MALIALIM from the company NIPPON OIL and FATS CO.
3 - Les liants réactifs phosphonés obtenus par les méthodes suivantes : a) Copolymérisation d'un monomère phosphoné avec un monomère tel que VDF, chlorure de vinylidène, etc.. 3 - Phosphonated reactive binders obtained by the following methods: a) Copolymerization of a phosphonated monomer with a monomer such as VDF, vinylidene chloride, etc.
Pour une telle copolymérisation, on utilise les monomères très réactifs par copolymérisation radicalaire, respectivement : - acryliques :
- styréniques :
- allyliques : For such a copolymerization, the very reactive monomers are used by radical copolymerization, respectively:
- styrenic:
- allylic:
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- vinyliques :
décrite dans les publications de B. HAMOUI et coll. Macromol. Chem. Phys., 1995, 176.
- vinylic:
described in the publications of B. HAMOUI et al. Macromol. Chem. Phys., 1995, 176.
1865 et B. HAMOUI et coll., J. Appl. Polym. Sci., 1994, 52, 449. 1865 and B. HAMOUI et al., J. Appl. Polym. Sci., 1994, 52, 449.
Ont également été préparés des copolymères de chlorure de vinylidène, avec des acrylates phosphonés par polymérisation radicalaire, de formule :
b) Modification chimique de polymères du commerce, par des réactifs phosphonés selon plusieurs méthodes : b-1) Ozonisation du polymère, suivie du greffage des acrylates ou styréniques phosphonés. Par exemple : greffage de polyfluorure de vinylidène par des acrylates phosphonés, selon la méthode enseignée par le brevet belge n 0940088 du 28. 09.94 au nom de
COCKERILL-SAMBRE. Copolymers of vinylidene chloride have also been prepared with phosphonated acrylates by radical polymerization, of formula:
b) Chemical modification of commercial polymers by phosphonated reagents according to several methods: b-1) Ozonization of the polymer, followed by grafting of the phosphonated acrylates or styrenics. For example: grafting of polyvinylidene fluoride with phosphonated acrylates, according to the method taught by Belgian Patent No. 0940088 of 28. 09.94 in the name of
Cockerill-SAMBRE.
La même méthode peut être appliquée à des polyoléfines (polyéthylène et polypropylène) et à diverses cires de ces polymères pour obtenir des lubrifiants réactifs. b-2)Modification de polyoléfines comptant des groupes insaturés (polyéthylène, polypropylène et PIB) et polydiènes, ou de copolymères les contenant, par des The same method can be applied to polyolefins (polyethylene and polypropylene) and to various waxes of these polymers to obtain reactive lubricants. b-2) Modification of polyolefins having unsaturated groups (polyethylene, polypropylene and PIB) and polydienes, or copolymers containing them, by
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mercaptans phosphonés ; à partir de copolymères styrène-butadiène, on réalise l'addition photochimique ou thermoamorcée mercaptan tel que :
préparés par la méthode suivante, par exemple :
- la même méthode a été appliquée à la modification des polybutadiènes hydroxy téléchéliques de la société ATOCHEM et carboxy téléchéliques de la société
GOODRICH. b-3) A partir de silicones
Les silicones fluorés ou non, peuvent être modifiés à partir des groupements SiH et Si-CH=CH2 présents dans les chaînes de silicones. phosphonated mercaptans; from styrene-butadiene copolymers, the photochemical or thermo-amorphous mercaptan addition is carried out such that:
prepared by the following method, for example:
the same method has been applied to the modification of the telechelic hydroxy polybutadienes of the company ATOCHEM and carboxy telechelic of the company
GOODRICH. b-3) From silicones
Fluorinated silicones or not, can be modified from the SiH and Si-CH = CH2 groups present in the silicone chains.
- sur les groupements Si - CH = CH2 on peut greffer, soit des thiols phosphonés, soit des hydrogénophosphonates de dialkyle (HPO(OR)2 R = alkyl). on the Si - CH = CH 2 groups, either phosphonized thiols or dialkyl hydrogen phosphonates (HPO (OR) 2 R = alkyl) can be grafted.
- sur les groupements SiH on peut greffer les allylphosphonates précédents. on the SiH groups, the preceding allylphosphonates can be grafted.
Les produits présentent les structures suivantes : The products have the following structures:
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b-4) A partir de polyéthers fluorés
Les huiles de marque " FOMBLIN Z " de la société AUSIMONT qui possèdent des fonctions alcools en extrémités de chaînes peuvent être modifiées comme suit :
b-4) From fluorinated polyethers
The oils of "Fomblin Z" brand from the company AUSIMONT which have alcohol functionalities at the chain ends can be modified as follows:
Finalement on obtient des composés du type :
Y-O (CF2O)x-(C2F4O)-Y avec Y = -CF2CH2O(CH2)3-PO(OR)2 b-5) A partir de polymères partiellement halogénés, notamment chlorés, des réactions de phosphonation peuvent s'effectuer selon la méthode d'ARBUZOV : Finally we obtain compounds of the type:
YO (CF 2 O) x- (C 2 F 4 O) -Y with Y = -CF 2 CH 2 O (CH 2) 3-PO (OR) 2 b-5) From partially halogenated polymers, in particular chlorinated polymers, phosphonation reactions can be carried out according to ARBUZOV method:
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L'application de cette réaction sur des dérivés paraffiniques chlorés permet d'accéder à des additifs lubrifiants réactifs dont les chaînes liées aux groupements réactifs, eux-mêmes représentés par deux types, phosphonates et phosphates, sont soit hydrocarbonées, soit fluorées, soit chlorofluorées. Application of this reaction to chlorinated paraffinic derivatives makes it possible to access reactive lubricating additives whose chains linked to the reactive groups, themselves represented by two types, phosphonates and phosphates, are either hydrocarbon-based, fluorinated or chlorofluorinated.
En ce qui concerne les phosphonates, on trouve :
polyéthers perfluorés modifiés par des groupements phosphoniques les paraffines chlorées phosphonées Ces produits sont obtenus : With regard to phosphonates, we find:
Phosphonically modified perfluorinated polyethers Phosphonated chlorinated paraffins These products are obtained:
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* soit par addition des thiols correspondants sur des oléfines fluorées :
* soit par action de P(OR), sur des halogénures d'alkyles :
* soit par addition sur des doubles liaisons de :
* soit par oligomérisation des oléfines fluorées :
* by adding the corresponding thiols to fluorinated olefins:
* by the action of P (OR), on alkyl halides:
* by addition on double bonds of:
* by oligomerization of fluorinated olefins:
En ce qui concerne les phosphates, la synthèse est réalisée à partir des alcools correspondants sur des dérivés phosphonés tels que POCl3, CI PO(OR)2' etc.
As regards the phosphates, the synthesis is carried out from the corresponding alcohols on phosphonated derivatives such as POCl3, CI PO (OR) 2 'etc.
Comme additifs réactifs, utilisables dans le cas de formulations à base de liants non réactifs, on retient également les acides phosphoniques, alkyl phosphoniques, acides phosphoriques, acide aminotriméthylène phosphonique, acide 1-hydroxyéthylidène-1-1- diphosphonique, acide éthylène diamine tétraméthylène phosphonique, acide hexaméthylène diamine tétra méthylène phosphonique, di-éthylène triamine pentaméthylène phosphonique. Reactive additives which may be used in the case of formulations based on nonreactive binders are also phosphonic acids, alkylphosphonic acids, phosphoric acids, aminotrimethylphosphonic acid, 1-hydroxyethylidene-1-1-diphosphonic acid and ethylene diamine tetramethylenephosphonic acid. hexamethylene diamine tetra methylene phosphonic acid, diethylene triamine pentamethylene phosphonic acid.
Conformément à la présente invention, on procède de la manière suivante à la synthèse des produits : According to the present invention, the products are synthesized as follows:
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1) L'acide phosphonique fluoré, C8F17C2H4SC3H6PO(OH)2, et ses origines sont décrits dans la publication " Synthesis of new phosphonic derivatives with fluorinated chains ", par C. 1) Fluorinated phosphonic acid, C8F17C2H4SC3H6PO (OH) 2, and its origins are described in the publication "Synthesis of new phosphonic derivatives with fluorinated chains", by C.
Brondino, B. Boutevin, Y. Hervaud, N. Pelaprat et A. Manséri, dans Journal of Fluorine Chemistry 76 (1996) 193-200. Brondino, B. Boutevin, Y. Hervaud, N. Pelaprat and A. Manséri, in Journal of Fluorine Chemistry 76 (1996) 193-200.
2) Pour le copolymère MMA/MAPHOS 5050 de formule :
Les monomères phosphonés ci-dessus sont décrits dans la thèse BACHAR HAMOUI " Synthèse de nouveaux monomères phosphonés. Télomérisation et Applications ". Diplôme de Doctorat - MONTPELIER - 24 Septembre 1991, ainsi que dans la publication : " Synthesis, Polymerisations of monomers bearing phosphonated group ". Part 1 - Applications on Acrylates and Methacrylates. B. BOUTEVIN - B. HAMOUI - J. P.PARISI. Journal of Applied Polymers Science 1994,52.449. 2) For the MMA / MAPHOS 5050 copolymer of formula:
The above phosphonated monomers are described in the BACHAR HAMOUI thesis "Synthesis of new phosphonated monomers, telomerization and applications". PhD degree - MONTPELIER - 24th September 1991, as well as in the publication: "Synthesis, Polymerizations of monomers bearing phosphonated group". Part 1 - Applications on Acrylates and Methacrylates. B. BOUTEVIN - B. HAMOUI - JPPARISI. Journal of Applied Polymers Science 1994,52,449.
L'analyse RMN du proton permet de déterminer les teneurs en MAPHOS (x (y) + qui sont (x + y) comprises entre 2 et 50 %. NMR analysis of the proton makes it possible to determine the contents of MAPHOS (x (y) + which are (x + y) between 2 and 50%.
3) Une cire de polyéthylène modifiée par greffage d'un acrylate phosphoné.de masse molaire voisine de 3000 et dont la fusion se situe à 90 C, est soumise à l'action de l'ozone dans un réacteur à lit fluidisé à température ambiante pendant 2 heures. Après réaction, on introduit 100g dans un rhéomètre de type BRABENDER, avec 10g d'un acrylate phosphoné (MAPHOS) de formule :
CH2=CH-CO2-CH2CH2-PO (OCH3)2 à la température de 90 C pendant 30 minutes. Ensuite, le mélange est lavé sur fritté par de l'acétone. On récupère 105g de polymère que l'on dissout dans du xylène à 100 C et auxquels on 3) A polyethylene wax modified by grafting a phosphonated acrylate molar mass close to 3000 and melting at 90 C, is subjected to the action of ozone in a fluidized bed reactor at room temperature during 2 hours. After reaction, 100 g are introduced into a BRABENDER rheometer, with 10 g of a phosphonated acrylate (MAPHOS) of formula:
CH2 = CH-CO2-CH2CH2-PO (OCH3) 2 at a temperature of 90 ° C for 30 minutes. Then, the mixture is washed on sintered with acetone. 105 g of polymer are recovered which are dissolved in xylene at 100 ° C. and to which
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ajoute 10g de bromotriméthylsilane. Enfin, après refroidissement, on ajoute 10g de méthanol avant de précipiter le polymère dans du THF. Le dosage acido-basique par de la soude N/10 donne une masse équivalente de 1830. add 10 g of bromotrimethylsilane. Finally, after cooling, 10 g of methanol are added before precipitating the polymer in THF. The acid-base assay with N / 10 sodium hydroxide gives an equivalent mass of 1830.
4) Une cire de polyéthylène chlorée modifiée par phosphonation. Dans du xylène porté au reflux, on dissout 100g de cire connue dans le commerce sous le nom déposé de " 55T CERECLOR" de la société Imperial Chemical Industries. On ajoute goutte à goutte 25g de phosphites de triéthyle P(OEt)3 et l'on condense le bromure d'éthyle qui se forme. Après précipitation dans le THF et séchage du polymère, l'analyse élémentaire donne CI = 44,6 % ; = 4,1 %. 4) A chlorinated polyethylene wax modified by phosphonation. In refluxed xylene, 100 g of wax known commercially under the tradename "55T CERECLOR" from Imperial Chemical Industries are dissolved. 25 g of triethyl phosphites P (OEt) 3 are added dropwise and the ethyl bromide which forms is condensed. After precipitation in THF and drying of the polymer, elemental analysis gives CI = 44.6%; = 4.1%.
5) Un copolymère styrène/butadiène modifié par un thiol phosphoné. 5) A styrene / butadiene copolymer modified with a phosphonated thiol.
Dans un ballon de 3 litres, on introduit 10g du produit connu dans le commerce sous le nom déposé de " FINAPREN 502 ", 2,76g de thiol phosphoné, O,lg de benzophénone, solubilisés dans 700 ml de THF. On dégaze la solution pendant 15 minutes à l'azote et l'on irradie le mélange réactionnel au moyen d'un rayonnement ultraviolet pendant 24 heures. In a 3-liter flask, 10 g of the product known under the trade name of "FINAPREN 502", 2.76 g of phosphonated thiol, 0.1 g of benzophenone, solubilized in 700 ml of THF are introduced. The solution is degassed for 15 minutes with nitrogen and the reaction mixture is irradiated with ultraviolet radiation for 24 hours.
On constate que la solution a formé un gel que l'on resolubilise dans un volume total de THF de 2,5 litres. En fin de réaction, on concentre la solution à 700 ml et on précipite dans 4 litres de méthanol. On filtre, on rince et on sèche sous vide le précipité blanc recueilli. On isole ainsi le copolymère greffé sous la forme d'une gomme élastique. It is found that the solution has formed a gel which is resolubilized in a total volume of THF of 2.5 liters. At the end of the reaction, the solution is concentrated to 700 ml and precipitated in 4 liters of methanol. The mixture is filtered, rinsed and the white precipitate collected is dried under vacuum. The graft copolymer is thus isolated in the form of an elastic gum.
L'analyse RMN'H (CDCl3) démontre la structure du produit :
NMR analysis (CDCl3) demonstrates the structure of the product:
Quant à l'analyse élémentaire, elle donne le pourcentage de phosphore du copolymère greffé. Dans ce cas, il est de 2 %. Le rendement de greffage est donc de 50 %. As for the elemental analysis, it gives the percentage of phosphorus of the graft copolymer. In this case, it is 2%. The grafting yield is therefore 50%.
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6) Un copolymère fluorure de vinylidène/allylphosphonate de diéthyle. 6) A vinylidene fluoride / diethyl allylphosphonate copolymer.
Dans un réacteur en Hastelloy de type PARR, on introduit 50ml d'acétonitrile, 1g de peroxyde de ditertiobutyle (6,94 10-3 mole), 12,3g d'allylphosphonate de diéthyle (6,94 10-2 mole) et 35g de fluorure de vinylidène (0,625 mole). Le mélange est chauffé sous agitation à 140 C pendant 10 heures. Après évaporation et purification du produit brut réactionnel, on obtient 21,3g de copolymère dont on vérifie par analyse élémentaire et par RMN qu'il a la composition molaire 84/16 (VF/allylphosphonate). In a Hastelloy reactor of the PARR type, 50 ml of acetonitrile, 1 g of di-tert-butyl peroxide (6.94 × 10 -3 mol), 12.3 g of diethyl allylphosphonate (6.94 × 10 -2 mol) and 35 g are introduced. of vinylidene fluoride (0.625 moles). The mixture is heated with stirring at 140 ° C. for 10 hours. After evaporation and purification of the crude reaction product, 21.3 g of copolymer are obtained, which is verified by elemental analysis and by NMR that it has the 84/16 molar composition (VF / allylphosphonate).
7) Du poly fluorure de vinylidène greffe par un acrylate phosphoné est obtenu par synthèse de type connue en soi, par exemple comme cela est décrit dans le brevet EP 0 704 465. 7) Polyvinylidene fluoride grafted with a phosphonated acrylate is obtained by synthesis of a type known per se, for example as described in patent EP 0 704 465.
8) Des silicones phosphonées
Les silicones (fluorées ou non) peuvent être modifiées à partir des groupements SiH et Si(CH=CH2) Si (V) que l'on peut introduire dans les chaînes : - sur les groupements SiH, on peut greffer des allylphosphonates de dialkyles - sur les groupements Si (V), peut greffer soit des thiols phosphonés, soit des hydrogénophosphonates de dialkyle H PO (OR)2. 8) Phosphonated silicones
The silicones (fluorinated or non-fluorinated) can be modified from the SiH and Si (CH =CH 2) Si (V) groups that can be introduced into the chains: on the SiH groups, dialkyl allylphosphonates can be grafted onto on the Si (V) groups, may be grafted either phosphonated thiols or H (PO) 2 dialkyl hydrogen phosphonates.
Les produits ont les structures suivantes :
The products have the following structures:
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Par exemple, à 100 ml de THF, on ajoute 60g de polysiloxane de masse molaire en nombre voisine de 6000 contenant 5% en mole d'unités hydrogénométhylsiloxane, 9g d'allylphosphonate de diéthyle et quelques gouttes de réactif de SPEIER (H2PtCl6 dans l'isopropanol). Le mélange est porté à reflux pendant environ quatre heures, c'est-à-dire jusqu'à ce que le mélange prenne la couleur noire. Après précipitation dans du méthanol, on recueille 67g de produit huileux dont on vérifie en IR et en RMN l'absence de liaison SiH. Dissous dans du THF, le produit est traité par du bromotriméthylsilane, puis par du méthanol. Le produit final est de l'acide phosphonique dosé par la soude et son poids équivalent est de 850. For example, to 100 ml of THF, 60 g of molar mass polysiloxane in number of about 6000 containing 5 mol% of hydrogenomethylsiloxane units, 9 g of diethylallyphosphonate and a few drops of SPEIER reagent (H2PtCl6 in isopropanol). The mixture is refluxed for about four hours, i.e., until the mixture becomes black. After precipitation in methanol, 67 g of oily product are collected, the absence of SiH bonding being verified by IR and NMR. Dissolved in THF, the product is treated with bromotrimethylsilane and then with methanol. The final product is phosphonic acid dosed with sodium hydroxide and its equivalent weight is 850.
9) Des huiles fluoro-phosphonées
A partir d'huiles fluorées telles que celles connues dans le commerce sous le nom déposé de " FOMBLIN Z " de la société Ausimont, fonctionnalisées par des groupements alcools, on peut réaliser l'allylation par le bromure d'allyle des extrémités de chaînes. Ensuite, l'addition d'hydrogénophosphonates de dialkyle HPO(OR)2 a des composés de structure suivante :
(RO)20P-(CH2)3-0-CH2CF2-0-(CF20),,-(C2F,O)Y-CF2-CH20-(CH2)3-PO(OR)2
Par exemple, à 27g de l'huile fluorée connue dans le commerce sous le nom déposé de " FOMBLIN Z ", qui est un polyéther perfluoré diol de masse molaire 2700 dissous dans 200ml de 112 trichlorotrifluoroéthane, on ajoute une solution de bromure d'allyle (5g) dans du THF (10ml). Puis, goutte à goutte, on ajoute 10ml de THF contenant 2g de soude. On porte à reflux pendant 10 heures et, après neutralisation et lavage à l'eau, on évapore les solvants pour recueillir environ 28g d'un produit soluble uniquement dans le trichlorotrifluoroéthane. 9) Fluoro-phosphonated oils
From fluorinated oils such as those known commercially under the trademark "FOMBLIN Z" from Ausimont, functionalized with alcohol groups, the allyl allyl allylation of the chain ends can be carried out. Then, the addition of dialkyl hydrogenphosphonates HPO (OR) 2 has compounds of the following structure:
(RO) 20P- (CH2) 3-0-CH2CF2-0- (CF20) ,, - (C 2 F, O) Y-CF2-CH20- (CH2) 3-PO (OR) 2
For example, at 27 g of the fluorinated oil known under the trade name "FOMBLIN Z", which is a 2700 molar mass perfluorolated polyether dissolved in 200 ml of 112 trichlorotrifluoroethane, a solution of allyl bromide is added. (5g) in THF (10ml). Then, dropwise, 10 ml of THF containing 2 g of sodium hydroxide are added. Refluxed for 10 hours and, after neutralization and washing with water, the solvents were evaporated to collect about 28 g of a soluble product only in trichlorotrifluoroethane.
A cette nouvelle solution, on ajoute 4g d'hydrogénophosphonate de diéthyle avec 150mg de percarbonate de cyclohexyle et on porte au reflux (48 C) pendant 4 heures. Le mélange est concentré et on distille l'excès d'hydrogénophosphonate de diéthyle. Après traitement par du bromotriméthyl silane, puis par du méthanol, le polyéther fluoré [alpha]# phosphoné est transformé en un [alpha]# diacide phosphonique. To this new solution is added 4 g of diethyl hydrogenphosphonate with 150 mg of cyclohexyl percarbonate and refluxed (48 C) for 4 hours. The mixture is concentrated and the excess diethyl hydrogen phosphonate is distilled off. After treatment with bromotrimethyl silane followed by methanol, the [alpha] # phosphonated fluorinated polyether is converted to a phosphonic acid [alpha] #.
Les exemples de formulations suivants illustrent l'invention. Ils sont répartis en trois classes : The following example formulations illustrate the invention. They are divided into three classes:
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A - LIANTS ET FILMOGENES NON REACTIFS
Dans ce qui suit, le butyral polyvinylique est le produit du commerce connus sous le nom déposé de " MOWITAL B 60 HH " de la société HOECHST, l'alcool polyvinylique Is = 120 est celui connus dans le commerce sous le nom de " MOWIOL 96-88 " de la société HOECHST. Les autres produits spécifiques ont été décrits précédemment. A - BINDERS AND NON-REAGENT FILMOGENES
In the following, polyvinyl butyral is the commercial product known under the registered name of "MOWITAL B 60 HH" HOECHST company, polyvinyl alcohol Is = 120 is that known commercially as "MOWIOL 96 -88 "from the company HOECHST. Other specific products have been described previously.
EXEMPLE 1 :
Butyral polyvinylique 15.0
Graphite KS 6 (LONZA) 5.0
Acide phosphorique 75% 4.0
Acide tridécylphosphorique 4. 0
Acétate de butyle 72.0
100. 0 EXEMPLE 2
Butyral polyvinylique 15.0
Polyfluorure de carbone 3.0
Acide phosphorique 75% 4.0
Acide tridécylphosphorique 4. 0
Acétate de butyle 74.0
100. 0 EXEMPLE 3
Butyral polyvinylique 15.0
Graphite KS 6 (LONZA) 5.0
Acide phosphorique 75% 4.0
Phosphonate de dodécyle 5.0
Acétate de butyle 71.0
100. 0 EXAMPLE 1
Polyvinyl butyral 15.0
Graphite KS 6 (LONZA) 5.0
Phosphoric acid 75% 4.0
Tridecylphosphoric acid 4. 0
Butyl acetate 72.0
100. 0 EXAMPLE 2
Polyvinyl butyral 15.0
Carbon Polyfluoride 3.0
Phosphoric acid 75% 4.0
Tridecylphosphoric acid 4. 0
Butyl acetate 74.0
100. 0 EXAMPLE 3
Polyvinyl butyral 15.0
Graphite KS 6 (LONZA) 5.0
Phosphoric acid 75% 4.0
Dodecyl phosphonate 5.0
Butyl acetate 71.0
100. 0
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EXEMPLE 4 :
Butyral polyvinylique 15. 0
Graphite KS 6 (LONZA) 5.0
Acide phosphorique 75% 4.0
Acide phosphonique fluoré :
C8F17- C2H4 - S - C3H6 PO(OH)2* 5. 0
Acétate de butyle 71.0
100. 0 EXEMPLE 5 (produit pulvérulent) :
Cire amide C (HOECHST) 75. 0
Copolymère MMA/MAPHOS 50/50 10.0
Graphite KS 6 (LONZA) 10.0
Stéréate de calcium 5.0
100. 0 EXEMPLE 6 :
Cire amide micronisée 15.0
Copolymère MMA/MAPHOS 50/50 10.0
Graphite KS 6 (LONZA) 5.0
Mono palmitate de sorbitan 20 OE 5.0
Alcool polyvinylique 1g : 120 5.0
Eau 60.0
100. 0 * " Synthesis of new Phosphonic derivatives with fluorinated chains ". EXAMPLE 4
Polyvinyl butyral 15. 0
Graphite KS 6 (LONZA) 5.0
Phosphoric acid 75% 4.0
Fluorinated phosphonic acid:
C8F17- C2H4 - S - C3H6 PO (OH) 2 * 5. 0
Butyl acetate 71.0
EXAMPLE 5 (powdery product)
Wax amide C (HOECHST) 75. 0
MMA / MAPHOS 50/50 10.0 Copolymer
Graphite KS 6 (LONZA) 10.0
Calcium sterate 5.0
100. 0 EXAMPLE 6
Micronized amide wax 15.0
MMA / MAPHOS 50/50 10.0 Copolymer
Graphite KS 6 (LONZA) 5.0
Mono sorbitan palmitate 20 OE 5.0
Polyvinyl alcohol 1g: 120 5.0
Water 60.0
100. 0 * "Synthesis of new Phosphonic derivatives with fluorinated chains".
C. BRONDINO, B.BOUTEVIN, Y.HERVAUD, N.DELAPRAT, A. MANSERI, Journal of
Fluorine Chemistry 1996,76. 193. C. BRONDINO, B. BOUTVIN, Y.HERVAUD, N. DELAPRAT, A. MANSERI, Journal of
Fluorine Chemistry 1996,76. 193.
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EXEMPLE 7 :
Huile de colza soufflée S100 # 18
Polymère végétal (ROBBE) 34.0
Paraffine chlorée E5G (ICI) 54.0
Graphite K6 (LONZA) 5.0
DEQUEST 2010 (MONSANTO) 8.0
Naphténate de plomb 2.0
100. 0 B - LIANTS ET FILMOGENES REACTIFS CARBOXYLES EXEMPLE 8 :
Copolymère anhydride maléique méthyl vinyl éther MM 40. 600 (ISP) 10.0
Polyfluorure de carbone 3.0
Acide phosphorique 75% 4.0
Acide stéaryl phosphonique 5.0
Méthyl éthyl cétone 78.0
100. 0
EXEMPLE 9 :
Copolymère anhydride maléique méthyl vinyl éther MM 40. 600 (ISP) 10.0
Graphite KS 6 (LONZA) 5.0
Acide phosphorique 75% 4.0
Acide tridécyl phosphorique 4.0 Nonyl phénol 80E 2. 0
Eau 75.0
100.0 EXAMPLE 7
Rapeseed rapeseed oil S100 # 18
Vegetable Polymer (ROBBE) 34.0
Chlorinated paraffin E5G (ICI) 54.0
Graphite K6 (LONZA) 5.0
DEQUEST 2010 (MONSANTO) 8.0
Lead Naphthalate 2.0
100. 0 B - CARBOXYL REACTIVE BINDERS AND FILMOGENS EXAMPLE 8
Maleic anhydride methyl vinyl ether copolymer MM 40. 600 (ISP) 10.0
Carbon Polyfluoride 3.0
Phosphoric acid 75% 4.0
Stearyl Phosphonic Acid 5.0
Methyl ethyl ketone 78.0
100. 0
EXAMPLE 9
Maleic anhydride methyl vinyl ether copolymer MM 40. 600 (ISP) 10.0
Graphite KS 6 (LONZA) 5.0
Phosphoric acid 75% 4.0
Tridecyl phosphoric acid 4.0 Nonyl phenol 80E 2. 0
Water 75.0
100.0
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EXEMPLE 10 :
Copolymère styrène acrylique
B880 (ZENECA) MM 90. 000 Tg C 52 20.0
Graphite KS 6 (LONZA) 8.0
Acide tridecyl phosphorique 8.0
Triphényl phosphoro-thionate
2. 0
White Spirit 62.0
100. 0 C - LIANTS ET FILMOGENES REACTIFS PHOSPHORES EXEMPLE 11 :
Cire de polyéthylène greffé/acrylate phosphoné 15.0
Graphite KS 6 (LONZA) 5.0
Triarylphosphite (IRGAPHOS TNPP) (CIBA) 2.0 "SOLVESSO 100" 78. 0
100. 0 EXEMPLE 12
Cire de polyéthylène chlorée modifiée par phosphonation 15.0
Graphite KS 6 (LONZA) 5.0
Triarylphosphite (IRGAPHOS TNPP) (CIBA) 2.0 "SOLVESSO 100" 78.0
100. 0 EXAMPLE 10
Acrylic styrene copolymer
B880 (ZENECA) MM 90,000 Tg C 52 20.0
Graphite KS 6 (LONZA) 8.0
Tridecyl phosphoric acid 8.0
Triphenyl phosphoro-thionate
2. 0
White Spirit 62.0
100. 0 C - PHOSPHORUS REAGENT BINDERS AND FILMOGENS EXAMPLE 11
Grafted polyethylene wax / phosphonated acrylate 15.0
Graphite KS 6 (LONZA) 5.0
Triarylphosphite (IRGAPHOS TNPP) (CIBA) 2.0 "SOLVESSO 100" 78. 0
100. 0 EXAMPLE 12
Phosphonation-modified chlorinated polyethylene wax 15.0
Graphite KS 6 (LONZA) 5.0
Triarylphosphite (IRGAPHOS TNPP) (CIBA) 2.0 "SOLVESSO 100" 78.0
100. 0
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EXEMPLE 13 :
Copolymère styrène-butadiène/modifié thiol phosphoné 15.0
Graphite KS 6 (LONZA) 5.0
Trifluorure de cérium 3.0
Acide tridécyl phosphorique 3.0
Acétate de butyle 24. 0 " SOLVESSO 100 " 50.0
100. 0 EXEMPLE 14 . EXAMPLE 13
Styrene-butadiene / phosphonated thiol-modified copolymer 15.0
Graphite KS 6 (LONZA) 5.0
Cerium trifluoride 3.0
Tridecyl phosphoric acid 3.0
Butyl acetate 24. 0 "SOLVESSO 100" 50.0
100. EXAMPLE 14
Copolymère VDF/allylphosphonate 15. 0
Graphite KS 6 (LONZA) 5.0
Acide tridécyl phosphorique 5.0
Isphorone 55.0
N-méthyl pyrrolidone 20.0
100. 0 EXEMPLE 15 :
Copolymère styrène-butadiène/modifié thiol phosphoné 15.0
Graphite KS 6 (LONZA) 5.0
Trifluorure de cérium 3.0
SOLVESSO 100 77.0
100. 0 VDF / allylphosphonate 15 copolymer
Graphite KS 6 (LONZA) 5.0
Tridecyl phosphoric acid 5.0
Isphorone 55.0
N-methyl pyrrolidone 20.0
100. EXAMPLE 15
Styrene-butadiene / phosphonated thiol-modified copolymer 15.0
Graphite KS 6 (LONZA) 5.0
Cerium trifluoride 3.0
SOLVESSO 100 77.0
100. 0
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EXEMPLE 16 (produit pulvérulent) :
Polyfluorure de vinylidène greffé acrylate phosphoné 75. 0
Graphite KS 6 (LONZA) 15.0
Cire amide C 10.0
100. 0 EXEMPLE 17 (produit pulvérulent) :
Exemple 16 90-95
Pigments (D) 5 - 10 Les pigments D peuvent être constitués de pigments réactifs du type connu dans le commerce sous le nom déposé de " HEUCOPHOS " de la société HEUBACH et qui se déclinent en : " ZCP " - orthophosphate de zinc, calcium, strontium modifié " ZPA " - orthophosphate de zinc, aluminium modifié " ZPO " - orthophosphate de zinc, basique, modifié organique " ZMP " - orthophosphate basique de zinc, molybdène, modifié " ZPZ " - orthophosphate basique de zinc, modifié organique " ZBZ " - phosphate, silicate de zinc, aluminium hydraté, modifié " Z-APP " - polyphosphate de zinc, calcium, aluminium, strontium, modifié, etc. EXAMPLE 16 (powdery product)
Vinylidene polyfluoride grafted phosphonated acrylate 75. 0
Graphite KS 6 (LONZA) 15.0
Wax amide C 10.0
EXAMPLE 17 (powdery product)
Example 16 90-95
Pigments (D) 5 - 10 The pigments D may consist of reactive pigments of the type known commercially under the registered name of "HEUCOPHOS" from the company HEUBACH and which are available in: "ZCP" - zinc orthophosphate, calcium, modified strontium "ZPA" - zinc orthophosphate, modified aluminum "ZPO" - zinc orthophosphate, basic, modified organic "ZMP" - basic zinc orthophosphate, molybdenum, modified "ZPZ" - basic zinc orthophosphate, modified organic "ZBZ" - phosphate, zinc silicate, hydrated aluminum, modified "Z-APP" - zinc polyphosphate, calcium, aluminum, strontium, modified, etc.
(D) - comporteront également des pigments opacifiants, pouvant procurer les teintes finales de revêtements recherchées L'ensemble est adapté plus particulièrement à l'obtention de revêtements réalisés par coextrusion. (D) - will also include opacifying pigments, which can provide the final shades of desired coatings The assembly is particularly suitable for obtaining coextruded coatings.
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D - ADDITIFS DE LUBRIFICATION - graphite - polyfluorure de carbone (CFx),, avec n = 1 - triphényl phosphoro thionate alkylé - triphényl phosphoro thionate - di-alkyl phosphites - tri aryl phosphites - trifluorure de cérium (CeF,) - alkylxanthates de molybdène - sels d'ammonium alkyl substitués de l'acide tétrathiomolybdique (RNH3)2 - MoS4). D - LUBRICATING ADDITIVES - graphite - carbon polyfluoride (CFx) ,, with n = 1 - triphenyl phosphoro thionate alkylated - triphenyl phosphoro thionate - di-alkyl phosphites - tri aryl phosphites - cerium trifluoride (CeF 2) - molybdenum alkylxanthates - substituted alkyl ammonium salts of tetrathiomolybdic acid (RNH3) 2 - MoS4).
E - TENSIO-ACTIFS - alkyl et aryl phosphonates éthoxylés - dérivés fluorocarbonés - sulfonate d'ammonium perfluoroalkylé - sulfonate de potassium perfluoroalkylé - sulfonate d'amino alcool perfluoroalkylé - acrylate perfluoroalkylé F - PIGMENTS - réactifs, de type phosphonates, molybdates, etc. E - TENSIO - ACTIVE - ethoxylated alkyl and aryl phosphonates - fluorocarbon derivatives - perfluoroalkyl ammonium sulfonate - perfluoroalkyl sulfonate perfluoroalkyl sulfonate perfluoroalkylated amino - perfluoroalkylated amino acid F - PIGMENTS - phosphonate, molybdate type reagents, etc.
- non réactifs, opacifiants - charges
Ces produits sont connus de l'Homme de Métier. - non-reactive, opacifying - fillers
These products are known to those skilled in the art.
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Des essais ont permis de constater qu'un composé conforme à l'invention donne des résultats particulièrement avantageux du fait de la simplicité d'application qui ne nécessite pas les nombreux traitements préalables qu'exige la technique actuellement connue. Tests have shown that a compound according to the invention gives particularly advantageous results because of the simplicity of application that does not require the many prior treatments required by the currently known technique.
Ainsi, un essai de tréfilage de fil machine de nuance 100C6 0 5.5 globulisé décalaminé par grenaillage a été effectué en déposant en continu un composé conforme à l'Exemple 1 ci-dessus pour la première passe seulement et avec huilage en continu pour chaque passe de tréfilage, jusqu'à la casse du fil qui est intervenue à la treizième passe après une réduction totale de 84,5 %, selon le tableau suivant :
Thus, a wire drawing test of 100C6.0 5.5 ball milled wire was carried out by continuous deposition of a compound according to Example 1 above for the first pass only and with continuous oiling for each pass. wire drawing, up to the breakage of the thread which occurred at the thirteenth pass after a total reduction of 84.5%, according to the following table:
<tb>
<tb> PASSE <SEP> N <SEP> # <SEP> Fil <SEP> (mm) <SEP> # <SEP> Filière <SEP> (mm) <SEP> % <SEP> de <SEP> réduction <SEP> Vitesse <SEP> linéaire <SEP> (m/mm.) <SEP> Remarques
<tb> 1 <SEP> 5.5 <SEP> 5.3 <SEP> 7 <SEP> 10
<tb> 2 <SEP> 5.3 <SEP> 4.88 <SEP> 15 <SEP> 60
<tb> 3 <SEP> 4. <SEP> 88 <SEP> 4. <SEP> 5 <SEP> 15 <SEP> 130
<tb> 4 <SEP> 4. <SEP> 5 <SEP> 4. <SEP> 15 <SEP> 15 <SEP> 159
<tb> 5 <SEP> 4.15 <SEP> 3.84 <SEP> 14 <SEP> 180
<tb> 6 <SEP> 3.84 <SEP> 3.54 <SEP> 15 <SEP> 200
<tb> 7 <SEP> 3.54 <SEP> 3. <SEP> 23 <SEP> 17 <SEP> 220
<tb> 8 <SEP> 3.23 <SEP> 3 <SEP> 14 <SEP> 240
<tb> 9 <SEP> 3 <SEP> 2.74 <SEP> 19 <SEP> 260
<tb> 10 <SEP> 2.74 <SEP> 2.56 <SEP> 13 <SEP> 276
<tb> 11 <SEP> 2. <SEP> 56 <SEP> 2. <SEP> 36 <SEP> 15 <SEP> 300
<tb> 12 <SEP> 2.36 <SEP> 2.16 <SEP> 16 <SEP> 330
<tb> 13 <SEP> 2.16 <SEP> 2 <SEP> 14 <SEP> 350 <SEP> Casse
<tb>
Taux de réduction total : 84.5% Il faut rappeler qu'avec la méthode actuelle de tréfilage d'un fil après phosphatation, outre les traitements préalables déjà rappelés plus haut, il faut prévoir un apport de savon lors de chaque passe alors que l'utilisation d'un composé selon l'invention élimine à la fois les traitements préalables et quelque apport que ce soit lors du tréfilage. <Tb>
<tb> PASS <SEP> N <SEP>#<SEP> Wire <SEP> (mm) <SEP>#<SEP> Die <SEP> (mm) <SEP>% <SEP> of <SEP> reduction <SEP > Speed <SEP> Linear <SEP> (m / mm.) <SEP> Remarks
<tb> 1 <SEP> 5.5 <SEP> 5.3 <SEP> 7 <SEP> 10
<tb> 2 <SEP> 5.3 <SEP> 4.88 <SEP> 15 <SEP> 60
<tb> 3 <SEP> 4. <SEP> 88 <SEP> 4. <SEP> 5 <SEP> 15 <SEP> 130
<tb> 4 <SEP> 4. <SEP> 5 <SEP> 4. <SEP> 15 <SEP> 15 <SEP> 159
<tb> 5 <SEP> 4.15 <SEP> 3.84 <SEP> 14 <SEP> 180
<tb> 6 <SEP> 3.84 <SEP> 3.54 <SEP> 15 <SEP> 200
<tb> 7 <SEP> 3.54 <SEP> 3. <SEP> 23 <SEP> 17 <SEP> 220
<tb> 8 <SEP> 3.23 <SEP> 3 <SEP> 14 <SEP> 240
<tb> 9 <SEP> 3 <SEP> 2.74 <SEP> 19 <SEP> 260
<tb> 10 <SEP> 2.74 <SEP> 2.56 <SEP> 13 <SEP> 276
<tb> 11 <SEP> 2. <SEP> 56 <SEP> 2. <SEP> 36 <SEP> 15 <SEP> 300
<tb> 12 <SEP> 2.36 <SEP> 2.16 <SEP> 16 <SEP> 330
<tb> 13 <SEP> 2.16 <SEP> 2 <SEP> 14 <SEP> 350 <SEP> Casse
<Tb>
Total reduction rate: 84.5% It should be remembered that with the current method of drawing a wire after phosphating, in addition to the previous treatments already mentioned above, it is necessary to provide a supply of soap during each pass while the use of a compound according to the invention eliminates both prior treatments and any contribution whatsoever during drawing.
D'autres essais ont été conduits pour le filage direct sur presse hydraulique en mesurant l'effort appliqué et le déplacement en millimètres pour obtenir un taux de réduction des lopins de 60 %. Other tests were conducted for direct spinning on hydraulic press by measuring the applied force and the displacement in millimeters to obtain a reduction rate of the plots of 60%.
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Sur la figure 1, on voit les courbes qui résultent de tels essais effectués sur des lopins phosphatés Zn avec du stéarate de sodium, la valeur de l'effort appliqué en tonnes étant portée en abscisses et le déplacement en millimètres étant porté en ordonnées. FIG. 1 shows the curves which result from such tests carried out on Zn phosphate slugs with sodium stearate, the value of the force applied in tons being plotted on the abscissa and the displacement in millimeters being plotted on the ordinate.
Les courbes différent quelque peu selon que le lopin correspondant est tourné, grenaillé, rectifié, sablé, huilé, etc. The curves differ somewhat depending on whether the corresponding piece is turned, blasted, ground, sanded, oiled, etc.
La figure 2 représente les résultats obtenus avec un composé conforme à l'invention appliqué à quatre lopins respectivement sablé, rectifié, grenaillé et tourné. On constate que ces résultats sont pratiquement identiques à ceux de la figure 1, étant rappelé que les lopins de la figure 1 ont dû subir tous les traitements préalables habituels alors que ceux de la figure 2 ont simplement été revêtus d'un composé conforme à l'invention dilué à 70 % dans de l'huile. Figure 2 shows the results obtained with a compound according to the invention applied to four plots respectively sanded, ground, blasted and rotated. It can be seen that these results are practically identical to those of FIG. 1, it being recalled that the plots of FIG. 1 had to undergo all the usual prior treatments whereas those of FIG. 2 were simply coated with a compound in accordance with FIG. The invention is diluted 70% in oil.
L'invention conduit donc à un procédé et à des produits particulièrement performants et exceptionnellement utiles à la protection de l'environnement, par la suppression totale qu'ils permettent des traitements lourdement polluants.The invention therefore leads to a process and products particularly effective and exceptionally useful for the protection of the environment, by the total elimination they allow heavily polluting treatments.
Claims (19)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9905554A FR2792949B1 (en) | 1999-04-30 | 1999-04-30 | NON-POLLUTANT REACTIVE COMPOUND FOR COATING METALS, TO PROTECT THEM FROM CORROSION AND TO FACILITATE MECHANICAL DEFORMATION |
EP00925364A EP1175461A1 (en) | 1999-04-30 | 2000-04-28 | Composition and method for preparing metal products designed to be shaped by a mechanical process of plastic deformation |
AU44113/00A AU4411300A (en) | 1999-04-30 | 2000-04-28 | Composition and method for preparing metal products designed to be shaped by a mechanical process of plastic deformation |
PCT/FR2000/001169 WO2000066667A1 (en) | 1999-04-30 | 2000-04-28 | Composition and method for preparing metal products designed to be shaped by a mechanical process of plastic deformation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9905554A FR2792949B1 (en) | 1999-04-30 | 1999-04-30 | NON-POLLUTANT REACTIVE COMPOUND FOR COATING METALS, TO PROTECT THEM FROM CORROSION AND TO FACILITATE MECHANICAL DEFORMATION |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2792949A1 true FR2792949A1 (en) | 2000-11-03 |
FR2792949B1 FR2792949B1 (en) | 2001-06-29 |
Family
ID=9545116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR9905554A Expired - Lifetime FR2792949B1 (en) | 1999-04-30 | 1999-04-30 | NON-POLLUTANT REACTIVE COMPOUND FOR COATING METALS, TO PROTECT THEM FROM CORROSION AND TO FACILITATE MECHANICAL DEFORMATION |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1175461A1 (en) |
AU (1) | AU4411300A (en) |
FR (1) | FR2792949B1 (en) |
WO (1) | WO2000066667A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1229087A1 (en) * | 2001-02-02 | 2002-08-07 | Primex-Metal Coatings Ltd. | Acidic, water-thinnable anti-rust coating |
CN115353777A (en) * | 2022-09-06 | 2022-11-18 | 安徽新大陆特种涂料有限责任公司 | Preparation method of high-permeability conversion rust-free anticorrosive primer |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6824882B2 (en) * | 2002-05-31 | 2004-11-30 | 3M Innovative Properties Company | Fluorinated phosphonic acids |
CN1323147C (en) * | 2003-03-28 | 2007-06-27 | 中国科学院长春应用化学研究所 | Anticorrosive polyaniline grease and its prepn |
DE102008016348B4 (en) * | 2008-03-29 | 2010-07-29 | Stefan Graichen | High temperature lubricants and their use in a process for hot working metals |
US10023944B2 (en) | 2014-04-01 | 2018-07-17 | Honda Motor Co., Ltd. | Compositions and integrated processes for advanced warm-forming of light metal alloys |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD223463A1 (en) * | 1984-04-05 | 1985-06-12 | Ifa Automobilwerke Veb | LUBRICATORY COVERAGE FOR PHOSPHATABLE SURFACES |
FR2557584A1 (en) * | 1984-01-04 | 1985-07-05 | Centro Speriment Metallurg | COATING FOR HEAT-RESISTANT SHEET METAL WITH HIGH PUNCHING ABILITY |
EP0291260A2 (en) * | 1987-05-11 | 1988-11-17 | Morton International, Inc. | Aqueous epoxy resin compositions and metal substrates coated therewith |
EP0421250A2 (en) * | 1989-10-02 | 1991-04-10 | Ppg Industries, Inc. | Protective coating composition |
-
1999
- 1999-04-30 FR FR9905554A patent/FR2792949B1/en not_active Expired - Lifetime
-
2000
- 2000-04-28 WO PCT/FR2000/001169 patent/WO2000066667A1/en not_active Application Discontinuation
- 2000-04-28 EP EP00925364A patent/EP1175461A1/en not_active Withdrawn
- 2000-04-28 AU AU44113/00A patent/AU4411300A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2557584A1 (en) * | 1984-01-04 | 1985-07-05 | Centro Speriment Metallurg | COATING FOR HEAT-RESISTANT SHEET METAL WITH HIGH PUNCHING ABILITY |
DD223463A1 (en) * | 1984-04-05 | 1985-06-12 | Ifa Automobilwerke Veb | LUBRICATORY COVERAGE FOR PHOSPHATABLE SURFACES |
EP0291260A2 (en) * | 1987-05-11 | 1988-11-17 | Morton International, Inc. | Aqueous epoxy resin compositions and metal substrates coated therewith |
EP0421250A2 (en) * | 1989-10-02 | 1991-04-10 | Ppg Industries, Inc. | Protective coating composition |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1229087A1 (en) * | 2001-02-02 | 2002-08-07 | Primex-Metal Coatings Ltd. | Acidic, water-thinnable anti-rust coating |
WO2002060999A1 (en) * | 2001-02-02 | 2002-08-08 | Primex Metal Coatings, Ltd. | Anti-rust coating |
CN115353777A (en) * | 2022-09-06 | 2022-11-18 | 安徽新大陆特种涂料有限责任公司 | Preparation method of high-permeability conversion rust-free anticorrosive primer |
CN115353777B (en) * | 2022-09-06 | 2023-10-13 | 安徽新大陆特种涂料有限责任公司 | Preparation method of high-permeability conversion rust-free anti-corrosion primer |
Also Published As
Publication number | Publication date |
---|---|
WO2000066667A1 (en) | 2000-11-09 |
EP1175461A1 (en) | 2002-01-30 |
AU4411300A (en) | 2000-11-17 |
FR2792949B1 (en) | 2001-06-29 |
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