US20050183793A1 - Method of improving the performance of organic coatings for corrosion resistance - Google Patents

Method of improving the performance of organic coatings for corrosion resistance Download PDF

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Publication number
US20050183793A1
US20050183793A1 US10/786,340 US78634004A US2005183793A1 US 20050183793 A1 US20050183793 A1 US 20050183793A1 US 78634004 A US78634004 A US 78634004A US 2005183793 A1 US2005183793 A1 US 2005183793A1
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Prior art keywords
resin
organosulfur compound
group
metallic substrate
sheets
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Abandoned
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US10/786,340
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English (en)
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Hyung-Joon Kim
Jinming Zhang
Richard Gandour
Roe-Hoan Yoon
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Posco Holdings Inc
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Individual
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Priority to US10/786,340 priority Critical patent/US20050183793A1/en
Assigned to POSCO reassignment POSCO ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GANDOUR, RICHARD D., YOON, ROE-HOAN, ZHANG, JINMING, KIM, HYUNG-JOON
Priority to KR1020040079845A priority patent/KR101043079B1/ko
Priority to EP05450029A priority patent/EP1568741B1/de
Priority to DE602005001409T priority patent/DE602005001409T2/de
Priority to JP2005039015A priority patent/JP4317144B2/ja
Priority to TW094104626A priority patent/TW200602131A/zh
Priority to CNB2005100542472A priority patent/CN100408645C/zh
Publication of US20050183793A1 publication Critical patent/US20050183793A1/en
Abandoned legal-status Critical Current

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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
    • C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
    • 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
    • C09D5/086—Organic or non-macromolecular compounds
    • 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

Definitions

  • This invention applies to polymeric resins that are used to coat metallic substrates for corrosion protection, and to a method of modifying the resins with organosulfur compounds for improved corrosion resistance.
  • the invention pertains to preparing a homogeneous mixture of the resin and the organosulfur compound.
  • Van Ooij, et al. U.S. Pat. Nos. 5,455,080; 5,498,481; 5,539,031 disclosed methods of coating CRS or electrogalvanized (EG) steel with a blended powder mixture comprising a thermosetting resin, a pigment and non-hydrolyzed organosilane coupling agent.
  • the mixture contains 0.01-10% by weight of an organosilane whose melting temperature is lower than the curing temperature of the resin. It is believed that organosilanes can diffuse toward a metal surface and form a crosslinked layer during curing step.
  • SAMs self-assembled monolayers
  • Shimakura, et al. (EP 1,002,889) disclosed an anticorrosive coating composition, comprising a silane coupling agent and an aqueous resin solution (or suspension). Additionally, phosphorus-containing ions and/or sulfur-containing compounds can be added to the coating solution.
  • the sulfur-containing compounds disclosed in this invention may be selected from the groups consisting of thio-carbonyls, triazine thiols, sulfide ions, and persulfate ions.
  • Kanai and Shimakura U.S. Pat. No. 6,607,587 disclosed an anticorrosive coating for metals, which comprises a resin, water, water-dispersible silica, and a thio-carbonyl compound.
  • Organosulfur compounds have a strong affinity for metal substrates and can form close packed SAMs on the surface. There have been attempts to use this SAMs to produce a corrosion-resistant coating (Jenning, 1996; Nozawa, 1997; Aramaki, 1999; Taneichi, 2001).
  • the invention described herein uses sulfur-containing organic compounds to modify resin solutions for forming a durable coating with enhanced corrosion resistance.
  • the instant invention describes a method of improving the performance of organic conversion coatings for metals by modifying the compositions of the organic resins by adding an organosulfur compounds.
  • the improved performance of the modified resin compositions can protect metal substrates from corrosion without chromation.
  • Several possible mechanisms may operate to enhance the properties of the coating:
  • the aforesaid organic resins to be used in the instant invention may be chosen from, but not limited to, acrylic, acrylic-urethane, epoxy, polyester, epoxy-polyester or fluorovinyl polymers.
  • the resins may be a single resin or a combination of several resins that are designed to coat metal substrates for the purpose of corrosion protection.
  • the aforesaid organosulfur compounds that can be used as modifiers of the organic resins may be selected from but not limited to thiols, xanthates, alkyl sulfides, alkyl disulfides, thiocarbamates, dithiocarbamates, thioureas, thiophenols, mercaptbpyridines, mercaptoanilines, mercaptoimidazoles, thiophenes, and thiophosphates.
  • bifunctional compounds with two terminal groups, one sulfur-containing and the other a non-sulfur containing polar group can serve as modifiers, provided that both groups are compatible with the afore said organic resins.
  • a distinguishing feature of the instant invention is the simplicity in coating a metal surface with the modified-resins. There are no needs to add additional steps or equipment. A mixture of the resin and organosulfur compounds can be directly applied to a metal surface by any means that is usually employed for the original resin. Also, there are no needs to modify the procedures or equipment involved in curing the coated surface. In fact, the process as disclosed in the instant invention simplifies the process by eliminating the chromation step.
  • the aforesaid modified resin can contain 0.001-0.5 moles per liter (M) of organosulfur compounds, preferably in the range of 0.02-0.05 M. This concentration may be used for electrogalvanized steel. For other metals, the optimal concentrations may differ slightly.
  • the modified-resins can be applied to metal surfaces by a roll or a bar coater and be cured at a temperature in the range of 100-350° C.
  • the coating thickness may be controlled according to the needs. For galvanized steels, coating thickness in the range of 1-2 ⁇ m may be sufficient as conversion coatings for cold-rolled steels.
  • FIG. 1 shows the photographs of the EG steel panels after 250 hours of salt spray tests.
  • the unprotected panel showed red rust, while the EG steel coated with unmodified resin shows white rust.
  • the panel coated with a resin containing 1-octadecanthiol (ODT) shows no sign of rust.
  • FIG. 2 is a schematic illustration of a metal substrate coated with a resin that has been modified with an organosulfur compound.
  • the triangles, squares and circles represent the components of the polymer.
  • the rods represent the organosulfur modifier.
  • FIG. 3 shows the hotographs of the EG steel panels after 144 hours of salt spray tests.
  • the unprotected EG steel showed red rust, while the panel coated with unmodified resin shows signs of corrosion.
  • the EG steel coated with a resin containing 16-mercaptohexadecanoic acid (MCA) shows no sign of corrosion.
  • FIG. 4 shows the photographs of the EG steel panels after 168 hours of salt spray tests.
  • the panels were coated with i) resin alone, ii) resin mixed with ODT dissolved in ethanol, iii) resin mixed with ODT dissolved in 1-butanol, and iv) resin mixed with ODT in 1:1 blend of ethanol and 1-butanol. All ODT solutions were at 0.1 M, and the resin and ODT solutions were blended at 70:30 ratio by volume.
  • a solution of organosulfur compound is prepared with a proper solvent.
  • a separate resin solution is also prepared according to the prescribed procedure for a particular resin.
  • the solution of the organosulfur compound is mixed with the resin solution at an optimal ratio.
  • the mixed solution is then applied to a metal surface by means of a suitable coating technique, for example, rolling, dipping, brushing, and spraying.
  • the coating is cured at an appropriate temperature to solidify the film on the metal substrate.
  • the organosulfur compound may be directly dissolved into the resin solution.
  • the organosulfur compounds that can be used for modifying resins may be selected from thiols, xanthates, alkyl sulfides, alkyl disulfides, thiocarbamates, dithiocarbamates, thioureas, thiophenols, mercaptopyridines, mercaptoanilines, mercaptoimidazoles, thiophenes, and thiophosphates.
  • These reagents can be of alkyl or aryl compounds, but straight chain alkyl compounds are preferred.
  • bifunctional compounds with two terminal groups, one sulfur-containing and the other non-sulfur containing polar group can serve as modifiers, provided that both groups are compatible with the resin.
  • a proper solvent has to be chosen to make the solution of organosulfur compound compatible with the resin solution.
  • the compatibility may mean that both solutions are miscible when mixed together, and a mixture of both solutions can produce a satisfactory coating without defects.
  • a proper solvent should be chosen so that the aforesaid resin-organosulfur mixture can remain stable for a desired period of time and also have a suitable fluidity.
  • the solvents should be environmentally acceptable and have a pleasant odor.
  • the preferred solvents include, but are not necessarily limited to, alcohols, acetone, turpentine, benzene, ethyl and butyl acetate, toluene, petroleum ester, xylene, alkane, mineral spirit, and water.
  • the particularly preferred solvents of the present invention are ethanol, 1-propanol, 1-butanol, or their mixture.
  • the mixing ratio controls the concentration of modifier in the resin-organosulfur mixture.
  • the concentration of the modifier in the mixture can be in the range of 0.001-0.5 M, preferably in the range of 0.02-0.05 M.
  • modifiers can be added to a paint, which is a blended resin mixture containing one or more additional additives such as a pigment and a filler.
  • the modified resin of the invention can provide corrosion resistance in a variety of metal substrates including, but not limited to, hot rolled and pickled steel sheet, CRS sheets, stainless steel sheet, hot-dipped metallic coated steel sheets, electroplated metallic coated steel sheets, aluminum sheets and aluminum alloy sheets, zinc sheets, zinc alloy sheets, copper sheets, copper alloy sheets, gold, and silver.
  • the metallic coating may include one or more layers of lead, lead alloy, nickel, nickel alloy, zinc, zinc layer, tin, tin alloy, and the like.
  • a phosphate conversion coating may also be applied to these steel sheets prior to being coated with the resin-organosulfur mixture.
  • the metal substrates may include continuous strip and foil, sheets cut to lengths as well as bars, angles, tubes and beams.
  • the organosulfur modifier may chemically bind with metal surface and, therefore, enhance the adhesion between the coating and substrate, giving an improved resistance to chemical attack, mechanical stress and weathering.
  • the small organosulfur molecules may also fill the pores present in the matrix of resin and help reduce the diffusion rate of corrosive media such as water, oxygen and ions to metal surface.
  • Another effect of the additives is that organosulfur molecules can orient over the topmost surface of the resin coating where the terminal groups of the surfactant may protrude. The orientation of organosulfur molecules over the topmost surface may be such that the coating has a lower surface free energy and act as the first protection against attack by corrosive media.
  • the organosulfur compounds may also serve as anti-oxidants.
  • the modified resin coating can significantly improve corrosion resistance when compared with pure resin coatings because of synergistic effects between the organosulfur compounds and the cured resin.
  • the organosulfur compound used as a modifier of a resin to form a protective coating on metal surface comprise an alkanethiol having the general formula R(CH 2 ) n SH, where R is a terminal group, which can be, but not necessarily limited to. H—, NH 2 —, HOOC—, HO—.
  • the number n represents the length of hydrocarbon chain, which can range from 7 to 21, and is most preferably 10 and 18.
  • a particularly preferred embodiment of the present invention is 1-octadecanethiol (ODT, CH 3 (CH 2 ) 17 SH). Details of a blended resin-organosulfur mixture of the invention will be better understood from the following examples.
  • a 0.1-M ODT solution was prepared in ethanol.
  • the resin solution was prepared by mixing 99 parts of polymer solution and 1 part of inorganic hardener solution, both of which were provided by a chemical company.
  • the ODT solution and resin solution were subsequently mixed together in the ratio of 30:70 by volume.
  • the resultant mixture solution was applied to a test panel of 12 ⁇ 7.5 cm by means of a No. 5 bar coater.
  • the panel was an electrogalvanized (EG) CRS sheet from Pohang Iron and Steel Company (POSCO).
  • EG electrogalvanized
  • POSCO Pohang Iron and Steel Company
  • test panels coated with the resins with and without ODT were subjected to salt spray test (SST) by following the test procedures of ASMT B117. Also subjected to SST was another EG steel panel without any treatment (control).
  • FIG. 1 shows the photographs of the three test panels after 250 hours of salt spray tests.
  • White rusts appeared on the surface of the control panel after 2-4 hours, while the resin coated panel showed white rusts after 48-72 hours.
  • the EG steel panels that had been coated with ODT-modified resin remained rust free after 250 hours of SST.
  • the water beads present in the surface indicate that the surface was still hydrophobic and still remained resistant to the attack of salt fogs. This example demonstrated that the corrosion resistance of resin coating on EG steel sheets can be improved by at least three times with the addition of ODT.
  • This example illustrates the optimization of the concentration of ODT as a modifier in the resin.
  • the coatings of ODT-modified resins were prepared in the same manner as described in Example 1, but the mixing ratio between resin solution and ODT solution (0.1M in ethanol) was varied in the range of 90:10 to 40:60 by volume.
  • the EG steel panels coated with the ODT-modified resins were subjected to salt spray tests.
  • Table 2 shows the results of the Tafel studies conducted on the test panels coated with modified resins. As shown, the density of the corrosion current reaches a minimum at the optimal mixing ratios and, hence, at the maximum corrosion resistance. Thus, there was a clear correspondence between the results of the Tafel studies and the salt spray tests.
  • a 16-mercaptohexadecenoic acid (MCA, HS(CH 2 ) 15 COOH) was used instead of ODT as a resin modifier.
  • MCA 16-mercaptohexadecenoic acid
  • This reagent was different from ODT in that it was a bi-functional sulfur-containing compound.
  • a 0.025 M MCA solution was prepared with ethanol and then mixed with the resin solution at a ratio of 1:1 by volume, which was not necessarily the optimal mixing ratio. At this ratio, the resin-organosulfur mixture contained 0.0125 M MCA.
  • the modified resin was used to coat an EG steel panel with a No. 5 bar coater. The coated panel was cured at 150° C. for 5 minutes. Under this condition, the coating thickness would be approximately 1-2 ⁇ m.
  • the EG steel panel coated with the modified resin was subjected to salt spray test. For comparison, salt spray tests were also conducted on an uncoated EG steel panel and an EG steel panel that had been coated with the unmodified
  • the untreated EG steel panel showed red rusts, while the panel coated with unmodified resin showed white rusts.
  • the EG steel panel coated with the resin modified with MCA exhibited no sign of corrosion, as shown in FIG. 3 .
  • ODT was dissolved in different solvents and mixed with the resin solution.
  • the resin-ODT mixtures were used to coat EG steel panels, which were subsequently subjected to salt spray tests.
  • the photographs of FIG. 4 were taken after 168 hours of the salt spray test for the EG steel panels coated with the following:
  • ODT-modified resin greatly increased the corrosion resistance of the EG steel.
  • Both ethanol and 1-butanol served as satisfactory solvents for ODT.
  • the resin-ODT mixtures exhibited low viscosities, but they were not very stable when ethanol was used as the solvent for ODT.
  • 1-butanol was a better solvent for ODT and, hence, the resin-ODT mixture was more stable.
  • the resin-ODT mixtures prepared with 1-butanol tended to be more viscose than the case of using ethanol as solvent.
  • a blend of ethanol and 1-butanol provided stable resin-ODT mixtures with low viscosities.
  • Other solvents may be used as solvents for ODT. It should also be noted here that when shorter-chain thiols are be used as resin modifiers, solvents of higher dielectric constants, including water, may be used.

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  • Application Of Or Painting With Fluid Materials (AREA)
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US10/786,340 2004-02-25 2004-02-25 Method of improving the performance of organic coatings for corrosion resistance Abandoned US20050183793A1 (en)

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US10/786,340 US20050183793A1 (en) 2004-02-25 2004-02-25 Method of improving the performance of organic coatings for corrosion resistance
KR1020040079845A KR101043079B1 (ko) 2004-02-25 2004-10-07 부식 방지를 위한 유기 코팅의 성능 향상 방법
EP05450029A EP1568741B1 (de) 2004-02-25 2005-02-15 Verfahren zur Verbesserung der Leistung von organischen Beschichtungen für Korrosionsbeständigkeit
DE602005001409T DE602005001409T2 (de) 2004-02-25 2005-02-15 Verfahren zur Verbesserung der Leistung von organischen Beschichtungen für Korrosionsbeständigkeit
JP2005039015A JP4317144B2 (ja) 2004-02-25 2005-02-16 腐蝕防止のための有機被覆の性能向上方法
TW094104626A TW200602131A (en) 2004-02-25 2005-02-17 Method of improving the performance of organic coatings for corrosion resistance
CNB2005100542472A CN100408645C (zh) 2004-02-25 2005-02-25 耐腐蚀有机涂层的改进方法

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US (1) US20050183793A1 (de)
EP (1) EP1568741B1 (de)
JP (1) JP4317144B2 (de)
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CN (1) CN100408645C (de)
DE (1) DE602005001409T2 (de)
TW (1) TW200602131A (de)

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US20090121192A1 (en) * 2007-11-08 2009-05-14 Enthone Inc. Self assembled molecules on immersion silver coatings
US20100291303A1 (en) * 2007-11-21 2010-11-18 Enthone Inc. Anti-tarnish coatings
US20100319572A1 (en) * 2007-06-21 2010-12-23 Enthone Inc. Corrosion protection of bronzes
WO2013028309A1 (en) * 2011-08-19 2013-02-28 Macdermid Acumen, Inc. Tarnish inhibiting composition for metal leadframes
US9238588B2 (en) 2013-08-02 2016-01-19 Ecolab USA, Inc. Organic disulfide based corrosion inhibitors
CN105640285A (zh) * 2016-01-26 2016-06-08 合肥天工标识标牌有限公司 一种耐腐蚀家用信报箱
US9809899B2 (en) 2014-08-07 2017-11-07 Macdermid Acumen, Inc. Treatment for electroplating racks to avoid rack metallization
US9834509B2 (en) 2015-08-05 2017-12-05 Ecolab Usa Inc. Metal-catalyzed oxidative coupling of thiols
US10508203B2 (en) 2014-09-26 2019-12-17 The Boeing Company Compositions and coatings with non-chrome corrosion inhibitor particles
US11242480B2 (en) 2017-08-03 2022-02-08 Championx Usa Inc. Thiol adducts for corrosion inhibition
CN114870413A (zh) * 2022-04-14 2022-08-09 杭州特种纸业有限公司 一种钢纸用氯化锌溶液循环利用方法
CN116926558A (zh) * 2023-07-24 2023-10-24 湖南新文锋智能装备有限公司 一种氧醚基黄原酸酯类金属缓蚀剂及其制备方法与应用

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CN103232597B (zh) * 2013-04-28 2015-07-29 同济大学 2-巯基苯并咪唑/聚苯胺防腐蚀复合材料及其制备方法
CN103242736B (zh) * 2013-05-20 2015-05-27 河北工程大学 高抗腐电弧喷涂锌铝合金涂层封孔剂与制备工艺及其应用
CN110003784B (zh) * 2017-05-23 2020-12-25 临沂市冉得利新型材料有限公司 一种铝合金材料的防腐蚀涂料及其制备方法和防腐蚀方法
CN113047229B (zh) * 2020-12-29 2022-07-15 武汉力拓桥科防撞设施有限公司 一种具有自润滑性、耐腐蚀防船撞设施

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DE602005001409D1 (de) 2007-08-02
EP1568741B1 (de) 2007-06-20
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CN1664025A (zh) 2005-09-07
TW200602131A (en) 2006-01-16
KR101043079B1 (ko) 2011-06-22
CN100408645C (zh) 2008-08-06
DE602005001409T2 (de) 2008-02-21
KR20050086353A (ko) 2005-08-30
EP1568741A1 (de) 2005-08-31

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