EP2691557A1 - Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication - Google Patents

Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication

Info

Publication number
EP2691557A1
EP2691557A1 EP12712951.8A EP12712951A EP2691557A1 EP 2691557 A1 EP2691557 A1 EP 2691557A1 EP 12712951 A EP12712951 A EP 12712951A EP 2691557 A1 EP2691557 A1 EP 2691557A1
Authority
EP
European Patent Office
Prior art keywords
polymeric
corrosion inhibitor
units
acids
carboxylic
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Withdrawn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
EP12712951.8A
Other languages
German (de)
English (en)
Inventor
Udo Straetmans
Marko SOLTAU
Felix Straetmans
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.)
Straetmans HighTac GmbH
Original Assignee
Straetmans HighTac GmbH
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 Straetmans HighTac GmbH filed Critical Straetmans HighTac GmbH
Priority to EP12712951.8A priority Critical patent/EP2691557A1/fr
Publication of EP2691557A1 publication Critical patent/EP2691557A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING 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
    • C23F—NON-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
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting 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
    • C23F11/173—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • 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
    • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D171/02—Polyalkylene oxides
    • 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
    • C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31678—Of metal

Definitions

  • the invention relates to a polymeric corrosion inhibitor for a metallic substrate, to the use of a polymeric corrosion inhibitor for treating metal surfaces, to a method of treating metal surfaces, and to a method of making a polymeric corrosion inhibitor.
  • the corrosion of metallic components is a significant problem and can lead to impairment of the functionality of the component.
  • Particular attention is paid to the corrosion protection of aluminum and its alloys due to the widespread use of aluminum in the aviation and in some cases in the automotive industry.
  • To inhibit or prevent corrosion it is known to coat the metal surface with a corrosion-inhibiting protective layer.
  • a particularly effective corrosion protection for many metals, especially aluminum, has long been achieved by a coating with chromate. Chromates are usually toxic, chromium (VI) is considered carcinogenic. The use of chromium (VI) as a corrosion inhibitor is therefore prohibited.
  • Substitute formulations eg chromium (III), zinc phosphate, other inorganic corrosion protection pigments, etc.
  • chromium (III) generally do not exhibit the good corrosion-inhibiting properties of chromium (VI) and / or are in part metal-specific, so that a broad multi-metal protection is not achieved can be.
  • Some corrosion inhibitors in the prior art also encounter health and / or ecological concerns. There is thus one
  • Organic corrosion inhibitors are chemicals that can strongly and partially adsorb on metal surfaces and in some cases can even bind after a chemical reaction. They can lead to a certain seal and thus build up a barrier effect or inhibit anodic or cathodic corrosion reactions. These corrosion inhibitors are usually in the form of weak acids and their derivatives, which form insoluble salts on the metal surface.
  • Organic corrosion inhibitors are to be distinguished from conventional organic dye or paint protective coatings. The latter usually have only an insufficient barrier effect against corrosion-demanding substances. For this reason, conventional dye or lacquer layers are predominantly not applied directly to the metal surface, but mostly to a primer layer which generally contains corrosion-inhibiting substances.
  • the primer layer may be a lacquer layer containing corrosion inhibitors as additives.
  • conductive polymers as corrosion inhibitors is known. A disadvantage of conductive polymers is that coatings can usually only be applied to the substrate with great difficulty (eg by means of electropolymerization).
  • the invention has recognized that a corrosion inhibitor on metal surfaces according to the invention forms a thin, long-term stable polymer layer which exhibits a good corrosion-inhibiting action.
  • the polymer layer can be a substantially monomolecular, ordered, chemisorbed layer whose thickness is determined essentially by the size of the macromolecules. This was not to be expected since the organic corrosion inhibitors of the prior art usually form thick, disorganized, physisorbed layers and polymers usually react rather sluggishly due to their low mobility.
  • Thin, chemisorbed layers offer several advantages. On the one hand, chemisorbed layers are long-term stable, ie they are more difficult to remove abradable compared to physisorbed layers. On the other hand, relatively little corrosion inhibitor is required in order to build up a corrosion-inhibiting film on the metal surface. Another advantage for many applications is that thin layers affect the surface geometry less than thick layers. For thick coatings, the surface geometry is largely determined by the coating. Geometric features of the metal surface, the dimensions of which are smaller or comparable to the layer thickness, are generally largely obscured by the coating. With a thin layer whose thickness is significantly smaller than the dimensions of the features, this is not given to the same extent. Surprisingly, the corrosion inhibitor according to the invention exhibits a largely unselective effect on metals and is thus outstandingly suitable for the multimetal protection z.
  • corrosion inhibitor refers to a substance that can slow, inhibit or prevent the corrosion of metals.
  • a polymeric corrosion inhibitor has at least one polymeric backbone having at least two interlinked monomer units. These may be the same monomer units (homopolymer), z. B. Ethoxy units, or uneven monomer units (co-polymer), z. Ethoxy and propoxy units.
  • the terms "polymer”, “monomer unit” and “monomer” are defined in the context of the invention as published in the REACH Regulation (EC) No. 1907/2006 on 30.12.2006 in the Official Journal of the European Union No. 396 p.
  • a polymeric corrosion inhibitor according to the invention can have up to six polymeric skeletons which are linked to one another via a bridge structural unit.
  • the term bridge structural unit denotes a non-polymeric organic structural element to which the at least one polymeric backbone is linked.
  • the starting point for the bridge structural unit a starter molecule for the polymerization, for example, an alcohol or polyol such. As glycerol or Dipentae- rithrol be, wherein the bridge structural unit does not necessarily have to be identifiable as a former starter molecule.
  • the bridge structural unit may also be a carbon atom to which the at least one polymeric backbone is linked.
  • a polymeric corrosion inhibitor according to the invention has the following formula:
  • A is a bridge structure unit, R 1 is identical or different and is H or an aliphatic, aromatic, olefinic, cyclic, heterocyclic, polycyclic or polyheterocyclic radical,
  • R 2 is identical or different and is a polymeric backbone
  • X is the same or different and is a functional group selected from the group consisting of carboxylic acids
  • the molar mass of the polymer is between 200 and 10,000, preferably 400 and 6,000.
  • the molecular weights given are, as usual with polymers, average molecular weights.
  • a polymeric corrosion inhibitor according to the invention may contain by-products, for example residual amounts of catalyst or unreacted monomers. The invention has recognized that these by-products do not adversely affect the action of the polymeric corrosion inhibitor.
  • the polymeric backbone R 2 may preferably be ethoxy- (EO), propoxy- (PO), butoxy- (BO), (CH 2 ) n -NH- (CH 2 ) m (with n, m from 0 to 10) units or mixtures of these units.
  • the polymeric backbone R 2 is a homopolymer of ethoxy units, a co-polymer based on a mixture of ethoxy and Propoxy units, or a homopolymer of propoxy units.
  • the backbone R 2 comprises 3 to 200, more preferably 5 to 100 monomer units.
  • the backbone may be branched, but advantageously it is a linear backbone.
  • X is a functional group selected from the group consisting of carboxylic acids; Dicarboxylic acids; Polycarboxylic acids; carboxylic; and amides and imides of the aforementioned groups.
  • the functional group X is um
  • R ' is an aliphatic, aromatic, olefinic, cyclic, heterocyclic, polycyclic or polyheterocyclic radical or a derivatized acyl radical and
  • R '' H or R '.
  • A is a bridge structural unit
  • R 1 is identical or different and is H or an aliphatic, aromatic, olefinic, cyclic, heterocyclic, polycyclic or polyhetero-cyclic radical,
  • R 2 is identical or different and is a polymeric skeleton
  • Y is identical or different and is a functional group selected from the group consisting of -OR, -NHR, -NR 2 , where R is identical or different to H or an aliphatic, aromatic, olefinic, is cyclic, heterocyclic, polycyclic or polyheterocyclic shear radical, preferably H, is the molecular weight of the polymer selected so that the 'molecular weight of the polymeric corrosion inhibitor from 200 to 10,000, preferably 400, and
  • the polymeric backbone R 2 of the polymer in step a) may preferably contain ethoxy- (EO), propoxy- (PO), butoxy- (BO),
  • the polymeric backbone R 2 is a homopolymer of ethoxy units, a co-polymer based on a mixture of ethoxy and propoxy units, or a homopolymer of propoxy units.
  • step a) The polymers mentioned in step a) are marketable (for example the polyetheramines sold by the companies Huntsman and BASF) and / or can be prepared by methods known to the person skilled in the art.
  • the reactions of step b) are known from the literature.
  • the polymeric corrosion inhibitor of this invention may not have fully reacted or not fully reacted functional groups on the polymeric backbone.
  • the invention has recognized that the effect of the polymeric corrosion inhibitor is not adversely affected thereby.
  • the invention furthermore relates to the use of a polymeric corrosion inhibitor according to the invention for the treatment of metal surfaces, preferably of surfaces.
  • a metal selected from the group consisting of iron, steel, aluminum, copper, zinc, magnesium, nickel, titanium and their alloys. More preferably, the metal is selected from the group consisting of aluminum and its alloys.
  • Another object of the invention is a method for treating a metal surface comprising contacting the metal surface with a polymeric corrosion inhibitor according to the invention.
  • the metal is selected from the group consisting of iron, steel, aluminum, copper, zinc, magnesium, nickel, titanium and their alloys, preferably from the group consisting of aluminum and its alloys.
  • the corrosion inhibitor according to the invention can be applied from a solvent but preferably from an aqueous dispersion or emulsion.
  • it may be a low-dose dispersion or emulsion.
  • a dispersion may contain about 0.01 to 4 wt.%, Preferably 0.1 to 0.4 wt.% Of polymeric corrosion inhibitor.
  • an emulsion may contain about 0.01 to 4 wt%, preferably 0.1 to 0.4 wt% polymeric corrosion inhibitor.
  • the dispersion or emulsion may contain additives. These are advantageously further corrosion inhibitors, such as inorganic pigments known from the prior art, for example zinc, calcium and aluminum pigments as phosphates, silicates or combinations thereof.
  • the dispersion preferably contains zinc phosphate as an additive.
  • Possible Additives are also other organic inhibitors such as sulfonates, phosphates, phosphonates.
  • a polymer layer with the following features is preferably applied to the metal surface: a. a thickness of ⁇ 50 nm, preferably -S 30 nm, more preferably about 10 nm; and / or b. more preferably ⁇ an occupancy of the metal surface with the polymer of ⁇ 2.5 mg / m 2, preferably ⁇ 1.5 mg / m 2 1 mg / m 2.
  • the invention has recognized that with the polymeric corrosion inhibitor according to the invention, on the one hand, thinner layers on the metal surface than in the prior art can be formed and, on the other hand, an improved corrosion-inhibiting effect is achieved.
  • a corrosion inhibitor according to the invention can also be present as an additive in a paint or color formulation. Paints containing the corrosion inhibitor according to the invention can be used, for example, as primers in the treatment of metal surfaces.
  • a metal workpiece obtainable by the above-mentioned method for treating a metal surface is the subject of the invention.
  • the term metal workpiece includes any material known in the art that has a metal surface.
  • the metal is selected from the group consisting of iron, steel, aluminum, copper, zinc, magnesium, nickel, titanium and their alloys. More preferably, the metal is selected from the group consisting of aluminum and its alloys.
  • the metal workpiece has a polymer layer with the following features: a.
  • the thickness of the polymer layer disposed on the metal surface is determined by X-ray photoelectron spectroscopy (XPS). This method also allows conclusions about the atomic composition of the layer. II. Corrosion tests
  • Standardized sample plates were used for all corrosion tests: a) Sample plates made by Q-Labs GmbH of type QD made of steel with the following material specification: ISO 3574 type CR1, CRS SAE 1008/1010, 0.5 mm thick, smooth surface b) Sample plates from Rocholl GmbH type AR made of aluminum with the following material specification: ISO 209-1, alloy 2024 T3 bare, 1.5 mm thick, uncoated surface
  • the salt spray test was carried out in a Salzsprühhunt according to ISO 9227 (manufacturer VLM GmbH) according to DIN 51.021 SS.
  • Sample plates were half-salted for a period of time at room temperature in salt water, i. 3% NaCl solution, immersed.
  • Y is an OH group
  • the polymeric backbone R 2 is an EO / PO block copolymer is catalytically esterified with an equimolar amount of a polycarboxylic acid (polymaleic acid).
  • the polymeric esters ⁇ PEC carboxylic acid is neutralized with amine, preferably triethanolamine (TEA).
  • A -CH 2 -CH-CH 2 -
  • Y is an NH 2 group
  • the polymeric backbone R 2 is a homopolymer of propoxy units is amidated with an equi-functional amount of polymaleic anhydride.
  • This polyamidocarboxylic acid PAC is neutralized with amine, preferably triethanolamine (TEA).
  • FIG. 1 shows, in a scanning electron micrograph, a freshly ground aluminum sample plate, type AR 2024 T3 bare, which is subsequently coated with corrosion inhibitor 2.
  • the sample plate was immersed for one hour in an emulsion containing 0.4 wt .-% corrosion inhibitor 2 and then dried at room temperature.
  • the scale is 10 ⁇ , while the determined by XPS measurement layer thickness of the inhibitor is one thousandth less.
  • Example 3 Figure 2 shows four aluminum sample plate type AR 2024 T3 bare.
  • Sample plates B and D were coated with corrosion inhibitor 2 as indicated in Example 2.
  • the thickness of the polymer layer is about 10 nm in each case.
  • the sample plates were ground fresh before being coated with a 400 grit abrasive.
  • Sample plates A and C were not treated with corrosion inhibitor and serve as comparative examples. These reference plates were also ground fresh.
  • Plate B (according to the invention) was de stored in salt water for 750 h.
  • Reference plate A was stored in salt water for only 250 hours.
  • Plate D (according to the invention) was subjected to a salt spray test for 250 hours.
  • Plate C (reference) was subjected to a salt spray test only for 100 hours.
  • compositions were prepared (VI: comparative formulation, Fl and F2 with corrosion inhibitor according to the invention).
  • FIG. 3 compares the sample plate treated with the comparative formulation VI with the sample plate treated with the formulation Fl be.
  • FIG. 4 compares the sample plate treated with the comparative formulation Vi with the sample plate treated with the formulation F2.
  • sample plate treated with the comparative formulation exhibits starting points from the defect a strong corrosive sub walls ⁇ tion of the paint layer, is responsible for determining the Formulie ⁇ stanchions Fl and F2 treated sample plates at most a slight infiltration of the varnish layer

Abstract

L'invention concerne un inhibiteur de corrosion polymère pour un substrat métallique, de la formule (R1)aA(R2X)b où a = 0-3, b = 1-6, A représente une unité de structure pontante, les R1, identiques ou différents, représentent chacun H ou un reste aliphatique, aromatique, oléfinique, cyclique, hétérocyclique, polycyclique ou polyhétérocyclique, les R2, identiques ou différents, représentent chacun un squelette polymère, les X, identiques ou différents, représentent chacun un groupe fonctionnel choisi dans le groupe constitué par les acides carboxyliques ; les acides dicarboxyliques ; les acides polycarboxyliques ; les anhydrides d'acides carboxyliques ; les chlorures d'acides carboxyliques ; les acides carboxyliques sulfoniques ; ainsi que les esters, amides et imides des groupes précédemment mentionnés, la masse molaire du polymère se trouvant entre 200 et 10 000, de préférence 400 et 6 000. L'invention concerne en outre l'utilisation d'un inhibiteur de corrosion polymère pour le traitement de surfaces métalliques, un procédé de traitement de surfaces métalliques ainsi qu'un procédé de fabrication d'un inhibiteur de corrosion polymère.
EP12712951.8A 2011-03-28 2012-03-28 Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication Withdrawn EP2691557A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12712951.8A EP2691557A1 (fr) 2011-03-28 2012-03-28 Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP20110159974 EP2505690A1 (fr) 2011-03-28 2011-03-28 Inhibiteurs de corrosion de type polymèrique pour des surfaces métalliques et leur méthode de fabrication
PCT/EP2012/001355 WO2012130442A1 (fr) 2011-03-28 2012-03-28 Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication
EP12712951.8A EP2691557A1 (fr) 2011-03-28 2012-03-28 Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication

Publications (1)

Publication Number Publication Date
EP2691557A1 true EP2691557A1 (fr) 2014-02-05

Family

ID=44344051

Family Applications (2)

Application Number Title Priority Date Filing Date
EP20110159974 Withdrawn EP2505690A1 (fr) 2011-03-28 2011-03-28 Inhibiteurs de corrosion de type polymèrique pour des surfaces métalliques et leur méthode de fabrication
EP12712951.8A Withdrawn EP2691557A1 (fr) 2011-03-28 2012-03-28 Inhibiteur de corrosion polymère pour des surfaces métalliques et sa fabrication

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP20110159974 Withdrawn EP2505690A1 (fr) 2011-03-28 2011-03-28 Inhibiteurs de corrosion de type polymèrique pour des surfaces métalliques et leur méthode de fabrication

Country Status (5)

Country Link
US (1) US20130330564A1 (fr)
EP (2) EP2505690A1 (fr)
JP (1) JP2014514446A (fr)
CN (1) CN103502510B (fr)
WO (1) WO2012130442A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012217693A1 (de) * 2012-09-28 2014-04-03 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung eines polymeren Korrosionsinhibitors zur Behandlung von Metalloberflächen
JP6699777B2 (ja) * 2018-03-30 2020-05-27 ダイキン工業株式会社 冷媒配管、熱交換器および冷媒配管の製造方法
CN111359021A (zh) * 2018-12-25 2020-07-03 先健科技(深圳)有限公司 含锌植入器械

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Publication number Priority date Publication date Assignee Title
US3231493A (en) * 1959-02-26 1966-01-25 Jefferson Chem Co Inc Method of inhibiting corrosion of oil well equipment
JPS4918550B1 (fr) * 1970-03-07 1974-05-10
US3948976A (en) * 1974-03-29 1976-04-06 American Cyanamid Company Partial esters of hydroxy polycarboxylic acids
US3962122A (en) * 1975-06-24 1976-06-08 Atlantic Richfield Company Polyamide corrosion inhibitor
US4392972A (en) * 1981-12-30 1983-07-12 Union Carbide Corporation Aluminum-corrosion inhibitive heat transfer fluid
US5391636A (en) * 1993-02-10 1995-02-21 Westvaco Corporation Polyamine condensates of styrene-maleic anhydride copolymers as corrosion inhibitors
EP0634460A2 (fr) * 1993-07-13 1995-01-18 ALBRIGHT & WILSON UK LIMITED Pigments anticorrosion
US5601754A (en) * 1995-04-21 1997-02-11 Betz Laboratories, Inc. Water treatment polymer containing poly[oxy-[(hydroxymethyl)-1,2-ethanediyl]] macromonomers and methods of use thereof
WO1997030103A2 (fr) * 1996-02-15 1997-08-21 The Dow Chemical Company Preparation de polyetheramines et de derives de polyetheramines
JP3382852B2 (ja) * 1998-06-08 2003-03-04 株式会社ジャパンエナジー 新規ポリオキシエチレンアルキルフェノールエーテル誘導体及びその製造方法並びにそれを用いる金属表面処理剤
US7851655B2 (en) * 2006-12-19 2010-12-14 Nalco Company Functionalized amine-based corrosion inhibitors for galvanized metal surfaces and method of using same
CA2766222A1 (fr) * 2009-07-03 2011-01-06 Akzo Nobel Chemicals International B.V. Polymeres inhibiteurs de corrosion

Non-Patent Citations (2)

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Title
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See also references of WO2012130442A1 *

Also Published As

Publication number Publication date
US20130330564A1 (en) 2013-12-12
CN103502510A (zh) 2014-01-08
EP2505690A1 (fr) 2012-10-03
CN103502510B (zh) 2016-08-03
WO2012130442A1 (fr) 2012-10-04
JP2014514446A (ja) 2014-06-19

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