EP1204706A1 - Procede de protection des metaux contre la corrosion et composition reactive non polluante pour sa mise en oeuvre - Google Patents
Procede de protection des metaux contre la corrosion et composition reactive non polluante pour sa mise en oeuvreInfo
- Publication number
- EP1204706A1 EP1204706A1 EP00951583A EP00951583A EP1204706A1 EP 1204706 A1 EP1204706 A1 EP 1204706A1 EP 00951583 A EP00951583 A EP 00951583A EP 00951583 A EP00951583 A EP 00951583A EP 1204706 A1 EP1204706 A1 EP 1204706A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- binder
- additive
- composition
- phosphonic
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/10—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/24—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials for applying particular liquids or other fluent materials
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C22/00—Chemical surface treatment of metallic material by reaction of the surface with a reactive liquid, leaving reaction products of surface material in the coating, e.g. conversion coatings, passivation of metals
Definitions
- the present invention relates to new macromolecular compounds, their synthesis and their use in admixture with a binder, in particular for paints, which can be used for the protection of metal surfaces against corrosion.
- a first disadvantage of the products described in the prior art is that it is necessary, for their synthesis, to start from a basic product, such as a halogenated polymer and / or copolymer of the polyvinylidene fluoride (PVDF) type, which is commercially available.
- PVDF polyvinylidene fluoride
- Another drawback is that the polymer and / or copolymer is thermoplastic and therefore sensitive to heat.
- a third drawback is that activation by electron beams or by ozone are expensive processes.
- CF 2 CF- (CF 2 ) x -PO (OH) 2
- Conventional paints are composed of a film-forming product which forms a film on the metal, one or more solvents, pigments and / or dyes, and which hardens at room temperature or at higher temperatures. These paints are applied to the metal directly when it is free of oxidation, impurities and / or dirt, or after an anticorrosion treatment thereof, for example phosphating followed by chromating.
- the products used for this anticorrosion treatment contain derivatives of heavy metals which are toxic and very volatile solvents. Thus, these treatments are harmful, both for human health and for the environment.
- the present invention relates to a treatment process and a composition which has the property of ensuring anticorrosion protection and adhesion to metal, while eliminating all the preliminary treatments and, in particular, the anticorrosive phosphating treatments and of chromating.
- the subject of the invention is a process for protecting metallic products against corrosion, characterized in that a formed composition is applied directly to the metallic products, that is to say without any prior treatment, at least one film-forming binder, at least one corrosion-inhibiting additive reactive with the metal and at least one oligomeric additive carrying phosphonic acids.
- the metal products to be treated having an excessively oxidized surface without, however, being scalded, they are subjected to a coarse brushing in order to reduce the oxidation of their surface to a low value, not necessarily zero, then applies the composition to them;
- the metal products to be treated being excessively greasy on the surface, they are subjected to a coarse cleaning which must bring back the fat of their surface at a low value, not necessarily zero, then the composition is applied to them.
- a subject of the invention is also a composition for the protection of metallic products against corrosion, comprising a binder and at least one additive, characterized in that it comprises a film-forming binder, at least one corrosion-inhibiting additive reactive with the metal and at least one oligomeric additive carrying phosphonic acids.
- composition • it also comprises one or more pigmentation additives;
- the wetting product is formed by at least one component selected from the following:
- the additives are random block or graft copolymers carrying sequences or grafts compatible with the binder;
- the additives are copolymers of at least one monomer compatible with the binder and at least one phosphonated monomer, - • the monomer compatible with the binder is polymerizable in chain, selected from methacrylic acrylics, styrenics, chloride of vinyl, vinyl fluoride or vinyl ester, -
- the monomer compatible with the binder is selected from polycondensable monomers, diols or epoxy diacids, -
- the reactivity additive is a phosphonate or a phosphate, the molecular chains of which are either hydrocarbon-based, fluorinated or chlorofluorinated; • the reactivity additive is formed by at least one component selected from:
- the reactivity is provided by carboxylic acid groups (the most frequent case) but also by phosphone groups which makes them more compatible with the additives of the present invention.
- the phosphonic groups are provided by monomers described below with regard to the reactive additives.
- Reactive additives These are molecular or macromolecular compounds with low molecular weights (less than a few thousand and preferably close to a thousand).
- R H, or alkyl • diphosphonic and telechelic compounds
- Z alkylene or arylene derived from non-conjugated dienes (divinylbenzene or hexadiene 1-5 for example) • polyphosphonic compounds:
- Structures can contain several phosphonic groups (> 2).
- phosphonic groups > 2
- PBHT phosphonic groups
- R H or alkyl
- the phosphonic groups are provided either by vinyl, allyl, acrylic or styrenic monomers or by telogen (R-X) agents of phosphonate type (alkyl or haloalkyl).
- the comonomers M 2 are all those generally used in copolymerization, well known to those skilled in the art, and of which here are some examples:
- R H, alkyl from vinyl acetate
- R H, alkyl from allyl acetate
- MMA methyl methacrylate
- MAHOS phosphonated methyl methacrylate
- Anti-corrosion additives zinc orthophosphate, calcium, modified strontium, - zinc orthophosphate, modified aluminum, zinc orthophosphate, organic modified, zinc orthophosphate, modified molybdenum, phosphate, zinc silicate, modified hydrated aluminum, zinc polyphosphate, calcium, aluminum, strontium, modified, etc.
- the invention will be better understood from the detailed description below, which is given only by way of an indicative and non-limiting example.
- the invention makes it possible to simplify the use of coatings and paints and to use the synergies of properties between the binders and the additives used.
- the binder has good barrier properties and if the additive has very good qualities of adhesion to the metal, the products obtained have excellent corrosion resistance properties.
- the phosphone monomers carry a polymerizable double bond and a phosphonic group, linked by a C-P bond to the side chain of this monomer.
- the polycondensable monomers have a phosphonate group linked by a C-P bond to the side chain of the monomer.
- reaction additives can also result from the chemical modification of commercial oligomers such as PBHT, from the company ATOCHEM,
- CH 2 C-C0 2 (CH 2 ) -PO (OCH 3 ) 2 product prepared according to the method described by C. BRONDINO (Montpellier thesis, 1996).
- the reaction mixture is degassed for 15 min, and brought to 70 ° C. Then 30 ml of the initiator solution are added dropwise. Two hours later, 30 ml of the initiator solution are again poured in dropwise. And finally, after 4 hours, the remainder of the initiator solution is poured dropwise.
- MMA be methyl methacrylate, the formula for phosphonated styrene being:
- the solution has formed a gel which is resolubilized in a total volume of THF of 2.5 liters.
- the solution is concentrated to 700 ml, and precipitated in
- Example 10 The reaction is then carried out under the same conditions as in Example 5.
- the final product has a fluorine content close to 31%, determined by elemental analysis.
- This copolymer can be treated using the same technique as that of Examples 6 to 8.
- Example 10 Example 10:
- Example 12 About 180 g of the copolymer according to Example 10 and containing 0.5 mole of equivalent -PO (OCH 3 ) 2 are introduced into a reactor. One mole of chlorotrimethylsilane is added and the mixture is left to react for two hours at room temperature. As in Examples 2 or 3, we then demonstrate by 1 H NMR, the appearance of a signal corresponding to the presence of groups OSi (CH 3 ) 3 .
- Example 12
- Example 13 Using the same operating conditions as for Example 5, a mixture composed of one mole of allyl alcohol and one mole of allyl diethylphosphonate is introduced into the reactor. After cooling, a gas mixture is introduced in the proportions 6.5 / 1.5 of fluoride vinylidene and chlorotrifluoroethylene. Under the same pressure conditions as for Example 5, after 6 hours of reaction and degassing, a fluorinated copolymer is obtained, the fluorine content of which, measured by elementary analysis, is close to 40%.
- Example 13 Example 13:
- Example 14 According to the operating conditions of Example 5, first of all 1 mole of diethyl allyl phosphonate, 1 mole of allyl alcohol and 1 mole of vinyl acetate are introduced.
- Hastelloy autoclave reactor with a capacity of 1000 ml, the following are introduced:
- Example 17 Under the same conditions described in Example 15, the reaction is carried out with chlorotrifluoroethylene (CTFE). 197 g (1.69 mole) are introduced. The mixture of telomeres obtained H- (CFCl-CF 2 ) n -PO (OEt) 2 has a DPn close to 2 and the conversion rate of CTFE is 78%.
- CTFE chlorotrifluoroethylene
- the phosphonate is 1 dimethyl hydrogen phosphonate HPO (OCH 3 ).
- Example 18 is 1 dimethyl hydrogen phosphonate HPO (OCH 3 ).
- Example 16 the phosphonate is 1 dimethyl hydrogen phosphonate: HPO (OCH 3 ) 2 .
- Example 16 The products of Example 16 are hydrolyzed as described in Example 19.
- Step 1 The synthesis of the MMA and MAPHOS block copolymer is carried out. Step 1 :
- a mixture of styrene, di-cumyl peroxide and "Tempo" (piperidine nitroxyl) is introduced in a molar ratio of 1000/1/2.
- GPG Gel Permeation Chromatography
- crosslinkable phosphates having the following formula is carried out:
- the alcohol C 12 H 2 sOH on P0C1 3 in chloroform is added mole to mole in chloroform, in the presence of triethylamine to capture the hydrochloric acid formed.
- the unsaturated alcohol C ⁇ 8 H 35 OH is added and after two hours of reflux in CHC1 3 , the mixture is hydrolyzed. After extraction, a monoacid whose acid number corresponds to the above formula is isolated.
- an aqueous solution is prepared having the following composition: 10 parts of the compound according to Example 24 1 part of nonyl phenoxy acetic aminoethanol acid in an amount sufficient to obtain 8.5 ⁇ pH ⁇ 9.5 6 parts of propylene glycol monomethyl ether water to make 100 parts.
- the compound according to Example 24 provides temporary protection for 168 hours because it is not crosslinked. It can be removed from the steel and then subjected to a subsequent treatment, for example it can be laminated, profiled, transformed by cutting, stamping, welding, etc.
- grade 10 On galvanized steel, grade 10 is obtained after 6 weeks of exposure. Without treatment, the same surface has a grade 1 corrosion, after a week of exposure.
- Example 25 The salt of the acid obtained according to Example 13 is epoxidized.
- Example 26 To one mole of acid of Example 13, one mole of ammonia is added and then 1.2 moles of p-chloroperbenzoic acid and the mixture is brought to reflux for one hour. The mixture is concentrated to 50% of dry extract.
- Example 26 To one mole of acid of Example 13, one mole of ammonia is added and then 1.2 moles of p-chloroperbenzoic acid and the mixture is brought to reflux for one hour. The mixture is concentrated to 50% of dry extract.
- Example 26 To one mole of acid of Example 13, one mole of ammonia is added and then 1.2 moles of p-chloroperbenzoic acid and the mixture is brought to reflux for one hour. The mixture is concentrated to 50% of dry extract.
- Diethyl hydrogen phosphonate HPO (OEt) 2 is added to 1-dodecene according to the method described by Pelaprat et al.
- Compound C 12 H 25 PO (OEt) 2 is obtained with a yield of 90%.
- This compound is hydrolyzed with bromotrimethyl ⁇ ilane, according to the method described by Hamoui et Coll (Macromol. Chem. Phys., 1985, 1995).
- esterification of this diacid is carried out in toluene, when hot, with a "dean stark" system to remove the water, esterification which is carried out with an alcohol of formula C ⁇ 8 H 35 OH to give the compound of the following formula:
- Example 28 This compound is epoxidized, as in Example 14, and then the acrylation is carried out as in Example 15.
- diethyl hydrogen phosphonate HPO (OEt) 2 is added to one mole of allylglycidylether.
- the following compound is obtained quantitatively: CH 2 -CH-CH 2 -0-C 3 H s -PO (OEt) 2
- the application is carried out by spraying or after dilution.
- the coating is baked for 10 minutes at 180 ° C or 15 minutes at 150 ° C. A coating is obtained, the protection duration of which is 500 hours (resistance to salt spray measured according to the AFNOR standard x 41.002). The hardness in pencil is F.2H. The NFR 30038 adhesion is 100%.
- Example 28 6 parts of the compound obtained in Example 28 5 parts of the maleic vinyl copolymer 4 parts of polyvinyl alcohol at 98% ammonia in an amount sufficient to obtain 8.5 ⁇ pH ⁇ 9.0 1 part of hydroxyethyl cellulose
- a non-ionic wetting agent HLB 12 8 parts of Zn 3 (P0 4 ) 2 , 2H 2 0 water to make 100 parts
- the density of the composition is 1.08 to 1.10.
- the FORD n ° 4 viscosity is 20 to 22 seconds.
- Example 29 From the alcohol obtained in Example 17,
- Cinnamic acid is added from the epoxide prepared in Example 14, according to the method of Example 15.
- composition in accordance with the invention can also be in the form of an aqueous emulsion:
- Example 31
- aqueous polyethylene emulsion was prepared from the following constituents:
- Dodecylphosphonic acid was prepared in two stages as follows:
- bromododecane 49.8 g of bromododecane are introduced into a three-necked flask fitted with a bromine bulb, an argon inlet and a distillation apparatus. The assembly is placed under an inert atmosphere and heated to 130 ° C. 36.5 g of triethyl phosphite are then added dropwise using the ampoule. After 24 hours of reaction, the remaining reagents are removed by vacuum distillation and 55.1 g of diethyl dodecylphosponate 1 are thus collected, ie a yield of 90%.
- the aqueous polyethylene emulsion is placed in a mechanical stirrer. With gentle stirring, Xanthan gum is added, then dodecylphosphonic acid. The stirring speed is gradually increased so as to obtain perfect dissolution of the additives in the emulsion.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9907440 | 1999-06-11 | ||
FR9907440 | 1999-06-11 | ||
PCT/FR2000/001636 WO2000077101A1 (fr) | 1999-06-11 | 2000-06-13 | Procede de protection des metaux contre la corrosion et composition reactive non polluante pour sa mise en oeuvre |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1204706A1 true EP1204706A1 (fr) | 2002-05-15 |
Family
ID=9546696
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00951583A Withdrawn EP1204706A1 (fr) | 1999-06-11 | 2000-06-13 | Procede de protection des metaux contre la corrosion et composition reactive non polluante pour sa mise en oeuvre |
Country Status (7)
Country | Link |
---|---|
US (1) | US6740173B1 (fr) |
EP (1) | EP1204706A1 (fr) |
JP (1) | JP2003527456A (fr) |
KR (1) | KR20020074059A (fr) |
CN (1) | CN1355829A (fr) |
AU (1) | AU6447700A (fr) |
WO (1) | WO2000077101A1 (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7179531B2 (en) * | 2002-09-12 | 2007-02-20 | Rohm And Haas Company | Polymer particles having select pendant groups and composition prepared therefrom |
JP4224561B2 (ja) * | 2003-09-22 | 2009-02-18 | 村▲瀬▼ 清隆 | クーラント補助液及びその使用方法 |
JP5078353B2 (ja) * | 2003-09-23 | 2012-11-21 | ソルヴェイ(ソシエテ アノニム) | ポリマー組成物 |
GB0507887D0 (en) * | 2005-04-20 | 2005-05-25 | Rohm & Haas Elect Mat | Immersion method |
CA2614399A1 (fr) * | 2005-07-08 | 2007-01-18 | Liliana Craciun | Composition de monomeres (meth)acrylamides contenant du phosphore |
FR2891548B1 (fr) * | 2005-10-05 | 2010-08-27 | Solvay | Dispersion aqueuse comprenant au moins un polymere du chlorure de vinylidene et au moins un copolymere |
JP2008222677A (ja) * | 2007-03-15 | 2008-09-25 | Chisso Corp | 難燃剤、それを用いた重合体組成物 |
WO2009072905A2 (fr) * | 2007-12-04 | 2009-06-11 | Katja Products Limited | Revêtement de surface |
MX2011003670A (es) * | 2008-10-31 | 2011-04-28 | Basf Se | Esteres fosfonicos de (met) acrilato como promotores de la adhesion. |
GB2466281A (en) * | 2008-12-19 | 2010-06-23 | 3M Innovative Properties Co | Composition comprising a fluorinated compound and a phosphate ester for treating surfaces |
CN103097038B (zh) * | 2010-07-21 | 2014-06-11 | 索尔维投资有限公司 | 用稳定的有机层涂覆无机基体的方法 |
KR20120010129A (ko) | 2010-07-21 | 2012-02-02 | 이와오 히시다 | 금속제품 표면의 가공방법 |
JP5827862B2 (ja) * | 2011-10-11 | 2015-12-02 | 住友化学株式会社 | メタクリル樹脂組成物からなる難燃板の製造方法 |
EP3070133B1 (fr) * | 2015-03-18 | 2019-02-20 | The Swatch Group Research and Development Ltd. | Pièce d'horlogerie ou de bijouterie comprenant une surface recouverte d'un agent épilame et procédé d'épilamage d'un tel substrat |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE7926T1 (de) * | 1980-02-01 | 1984-06-15 | Imperial Chemical Industries Plc | Waessrige anstrichmittel und ihre verwendung. |
CA1199786A (fr) * | 1982-11-10 | 1986-01-28 | Kenneth F. Baxter | Peinture anticorrosion |
GB8701705D0 (en) * | 1987-01-27 | 1987-03-04 | Ici Plc | Corrosion inhibition |
GB9111704D0 (en) * | 1991-05-31 | 1991-07-24 | Ciba Geigy | Telomers |
BE1008706A3 (fr) * | 1994-09-28 | 1996-07-02 | Cockerill Rech & Dev | Produit pour la formation d'un revetement sur un support et procede de preparation de ce produit. |
JPH0959562A (ja) * | 1995-08-29 | 1997-03-04 | Dainippon Toryo Co Ltd | 塗料組成物 |
DK12497A (da) * | 1996-02-12 | 1997-08-13 | Ciba Geigy Ag | Korrisionsinhiberende overtrækssammensætninger til metaller |
KR100498948B1 (ko) * | 1997-07-30 | 2005-07-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 포스폰산 반응 생성물 및 코팅 조성물에 있어 이들의 용도 |
-
2000
- 2000-06-13 KR KR1020017015930A patent/KR20020074059A/ko not_active Application Discontinuation
- 2000-06-13 WO PCT/FR2000/001636 patent/WO2000077101A1/fr not_active Application Discontinuation
- 2000-06-13 AU AU64477/00A patent/AU6447700A/en not_active Abandoned
- 2000-06-13 CN CN00808795A patent/CN1355829A/zh active Pending
- 2000-06-13 JP JP2001503947A patent/JP2003527456A/ja active Pending
- 2000-06-13 US US10/018,175 patent/US6740173B1/en not_active Expired - Fee Related
- 2000-06-13 EP EP00951583A patent/EP1204706A1/fr not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO0077101A1 * |
Also Published As
Publication number | Publication date |
---|---|
JP2003527456A (ja) | 2003-09-16 |
US6740173B1 (en) | 2004-05-25 |
WO2000077101A1 (fr) | 2000-12-21 |
KR20020074059A (ko) | 2002-09-28 |
AU6447700A (en) | 2001-01-02 |
CN1355829A (zh) | 2002-06-26 |
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