Anticorrosion Additive for Metalworking Fluids

1 INTRODUCTIONA variety of metal working fluids are used for the

machining operations of cutting, grinding, turning, milling,drilling, and tapping mainly for iron and aluminum metals.Many technical books 1, 2) and reviews 3, 4) on lubrication inmetal working and cutting for irons are known. However,the review of those for aluminum alloy materials is quitefew. Aluminum materials are apt to be blackish by mechan-ical processing, owing to corrosion of aluminum. Variousattempts to prepare high performance additives for alu-minum materials have recently been made. Many patentson corrosion inhibitors in metal working and cutting of alu-minum materials are known. Usually water-soluble cuttingfluids consist of many components. However, the detailedcompositions of the commercial products have not beenknown. The most important additive is a surface activeagent having anti-corrosion and other useful properties.The surface active agent is called a metal working fluidadditive. This short review article describes preparationsand properties of new types of metal working fluids addi-tives which have been developed in our laboratory andreported in literatures.

2 METAL WORKING FLUIDS ADDITIVES FOR ALU-MINUM ALLOY MATERIALSThis chapter describes our evaluation of various addi-

tives derived from a variety of organic compounds forwater-soluble metal working fluids of aluminum alloy mate-rials. Alkanolamines such as triethanolamine ordiethanolamine are used to dissolve acidic ingredients intowater, to increse anti-microbial activity of the fluids, andfor other purposes. Aluminium alloy materials are apt to beblackish in alkaline media (pH=9.0). Various corrosioninhibitors are added to cutting fluids. The use of tri-ethanolamine or diethanolamine salts gave the best resultsin our experiments for anti-corrosion and lubricity charac-teristics of cutting fluid additives.

2.1 Silicone compoundsIt is well known that sodium metasilicate is effective for

corrosion inhibitor of aluminum alloy materials5). However,solubility of sodium metasilicate in water is poor. The long-term safe keeping of the fluids containing sodium metasili-cate is difficult because of the precipitation of inorganiccompounds. Recently, it has been reported that compound(II) in Fig. 1, which is prepared from water-soluble silicate

1

Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 onlinehttp://jos.jstage.jst.go.jp/en/

Correspondence to: Shoji Watanabe, Akitsu 1-3-5-502, Narashino, Chiba 275-0025, JAPANE-mail: [email protected] September 26, 2007 (received for review August 13, 2007)

Journal of Oleo ScienceCopyright 2008 by Japan Oil Chemists SocietyJ. Oleo Sci. 57, (1) 1-10 (2008)

Shoji WatanabeAkitsu 1-3-5-502, Narashino, Chiba 275-0025 (Professor Emeritus of Chiba University; Former: Department of Applied Chemistry, Faculty ofEngineering, Chiba University, Yayoicho, Inage-ku, Chiba, 263-0085 JAPAN)

Abstract: This short review describes various types of anti-corrosion additives of water-soluble metalworking fluids for aluminum alloy materials. It is concerned with synthetic additives classified accordingto their functional groups; silicone compounds, carboxylic acids and dibasic acids, esters, Diels-Alderadducts, various polymers, nitrogen compounds, phosphoric esters, phosphonic acids, and others. Testingmethods for water-soluble metal working fluids for aluminum alloy materials are described for a practicalapplication in a laboratory.

Key words: water-soluble metal working fluids, additives, aluminum alloy materials, anti-corrosion property, testingmethods

REVIEW

Preparations and Properties of Anti-corrosion Additives of Water-soluble Metal Working Fluids for Aluminum Alloy Materials

S. Watanabe

(I) and alkali, is very effective as an anti-corrosion additivefor aluminum metal 6). A mixture of compound (II), tri-ethanolamine and water showed good anti-corrosion prop-erty for aluminum alloy materials. As other patents,polyalkyl {(N-aminoalkyl) iminoalkyl} siloxane 7) and othersare known. In the near future, new silicone surface activeagents may be put on the market. A better additive may beprepared.

2.2 Carboxylic acids and dibasic acidsp-t-Butylbenzoic acid 8) and dodecanedioic acid 4) have

excellent anti-corrosion properties for iron materials. It isreported that the metal working fluid composed of t-butyl-benzoic acid, dodecenylsuccinic ester, morpholine and ben-zotriazole shows excellent anti-corrosion properties foraluminum, copper and iron materials9).

The dibasic acids higher than dodecanedioic acid havenot been examined regarding their properties as the corro-sion inhibitor against aluminum alloy materials. Interest-ingly, the author and coworkers have found that the saltsof dibasic acid (C16 , C18 and C20) with an amine showgood anti-corrosion property against aluminum alloy. Forexample, the aqueous solution of 1,18-octadecanedioic acidwith 2-amino-2-methyl-1-propanol showed good anti-corro-sion property for aluminum alloy materials. Similarly, thesalts of 1,16-hexadecanedioic acid and 1, 20-eicosanedioicacid with 2-amino-2-methyl-1-propanol showed anti-corro-sion property for aluminum alloys. The results are shownin Table 1 10, 11).

2.3 EstersIt is known that esters of higher hydroxy fatty acids

have anti-corrosion properties for iron materials12). In thissection the author describes the evaluations of some estersas an aluminum corrosion inhibitor. Dodecanedioic acidanhydride (IV) was prepared by the dehydration reaction ofdodecanedioic acid (III) with acetic anhydride as shown inFig. 2. A variety of half esters of (III) were prepared fromthe reaction of (IV) and various hydroxyl compounds. For

2J. Oleo Sci. 57, (1) 1-10 (2008)

Testing method is described in the Section 3.

Table 1 Anti-corrosion Property of Higher Dibasic Acids for Aluminum AlloyMaterials 10-11).

Dibasic acid Structure Test of discoloring

Sebacic acid HOOC(CH2)8COOH

Dodecanedioic acid HOOC(CH2)10COOH

Tetradecanedioic acid HOOC(CH2)12COOH

Hexadecanedioic acid HOOC(CH2)14COOH

Octadecanedioic acid HOOC(CH2)16COOH

Eicosanedioic acid HOOC(CH2)18COOH

Fig. 1 Preparation of Compound (II)6).

Fig. 2 Preparation of Compound (VI)13).

Water-soluble Metal Working Fluids Additives

example, compound (VI) was obtained from (IV) andtrimethylolpropane (V). Triethanolamine salt of the halfester (VI) showed good anti-corrosion properties for alu-minum as shown in Table 2. Monoesters (e.g., glycerol,trimethylolpropane, phytanetriol, 1,4-cyclohexanediol andricinoleic acid tetramer) of (III) exhibited good anti-corro-sion behavior for aluminum13, 14).

The long use of water-soluble metal working fluids is aptto produce precipitates owing to Ca2+ and Mg2+ in hardwater. The additives which possess both the anti-corrosion

property for aluminum and a good hard water tolerancehave not been reported. The author and co-workers devel-oped the additives having both of them. A variety of halfesters and diesters were prepared from the reactions ofvarious hydroxyl compounds with some acid anhydrides.For example, a mixture of tetrahydrofuran oligomer(PTMG) (VII) and maleic anhydride was heated to givediester (VIII) in high yields (Fig. 3). The diester of PTMGand polybutylene oxide (PBO) with maleic anhydrideshowed both anti-corrosion properties for aluminum alloymaterial and hard water tolerance (Table 3) 15). New estershaving anti-corrosion and other useful properties willappear in near future.

2.4 Diels-Alder adductsIt is known that oleic acid, ricinoleic acid and dehydrat-

ed castor oil fatty acids have a considerable anti-corrosionproperty for aluminum material. In this section the authordescribes the evaluations of some thermal products ofunsaturated fatty acids with acrylic acid and maleic anhy-dride as an aluminum corrosion inhibitor. A mixture ofdehydrated ricinoleic acid (IX) with acrylic acid in thepresence of anhydrous aluminum chloride was heated at140 to give a Diels-Alder adduct (X) with various by-products (Fig. 4). The main product was assumed to be thecorresponding Diels-Alder adduct. Similarly, other Diels-Alder products were prepared from the reaction of (IX)with some dienophiles. Triethanolamine salt of compound(X) showed good anti-corrosion properties for aluminum asshown in Table 4. The thermal adduct of (IX) with maleicanhydride and that of linoleic acid with acrylic acid ormaleic anhydride exhibited good anti-corrosion behaviorfor aluminum, respectively. Interestingly, the anti-corro-sion properties of these thermal adducts were better thanthose of (IX) and linoleic acid. These results suggest thatthe presence of the bulky alkyl group in higher unsaturatedfatty acid molecule enhances their anti-corrosion propertyfor aluminum material 16).

3J. Oleo Sci. 57, (1) 1-10 (2008)

Table 2 Anti-corrosion Tests of Half Esters forAluminum Alloy Materials 13).

Half esters

Acid anhydride

Alcohols (molar ratio)

pH

Anti-corrosion tests

For aluminum after

24 hr

Dodecanedioic acid anhydride

Trimethylolpropane (2:1)8.7


Glycerin (2:1)8.74


Ricinoleic acid tetramer (1:1)8.61


Phytanetriol (2 :1)8.87


1,4-Cyclohexanediol (1.5 :1)8.53

Adipic acid anhydride

Phytanetriol (2:1)8.72

Glutaric acid anhydride

Trimethylolpropane (2:1)8.2


Monostearin (1.5:1)8.69


Phytantriol (2:1)8.72

Succinic acid anhydride

Monostearin (1.5 :1)8.75

Succinic acid anhydride

Phytanetriol (2 :1)8.43

Dodecanedioic acid 8.02

Sebacic acid 7.89

Adipic acid 7.7

Triethanol amine 10.4

Water

Fig. 3 Reaction of PTMG 650 (VII) with MaleicAnhydride15).

S. Watanabe

2.5 Various polymersRecently, homopolymers and copolymers are used for

metal working fluids additives. For example, water solublemetal working fluids containing compounds (XI) or (XII) inFig. 5 are used as cutting and grinding fluids for aluminummaterials17).

The following compounds for corrosion inhibitors andprocessing fluids have been reported; maleic acid homo-

polymers or copolymers 18), graft copolymers of polyetherand monoethylenic unsaturated carboxylic acids 19), alky-lene oxide adducts to fatty alcohols (weight average molec-ular weight = 1000 10,000)20), and oil-soluble copolymers(molecular weight > 3000) having a special structure 21) andmany others.

4J. Oleo Sci. 57, (1) 1-10 (2008)

Table 3 Reaction Products of Various Alcohols with Maleic Anhydride and Their Anti-corrosion Tests forAluminum and Hard Water Tolerance15).

Numbers of 650 and 1000 are average molecular weights of PTMG and PBO.

Hard water tolerance tests were performed according to the references method35).

MA is maleic anhydride.

Entry

No.Alcohols

Acid

anhydride

Molar

ratio

Anti-corrosion test of

aluminum After 24 h

Hard water tolerance

After 24 h

1 PTMG 650 MA 1 1

2 PTMG 650 MA 1 2

3 PTMG 1000 MA 1 1

4 PTMG 1000 MA 1 2

5 PBO 650 MA 1 2

6 PBO 1000 MA 1 2

Ricinoleic acid

NPG

Tall oil fatty acids

Undecylenic acid

Dodecanoic acid

Table 4 Anti-corrosion Test of Thermal Reaction Products for Aluminum Alloy Materials 16).

Unsaturated fatty acids Dienophiles Anti-corrosion test for aluminum after 24 h

Dehydrated castor oil fatty acid Maleic anhydride

Dehydrated castor oil fatty acid Acrylic acid

Dehydrated castor oil fatty acid Methyl acrylate

Dehydrated castor oil fatty acid Methacrylic acid

Linoleic acid Maleic anhydride

Linoleic acid Acrylic acid

Linoleic acid Methylacrylate

Linoleic acid Methacrylic acid

Dehydrated castor oil fatty acid ---

Linoleic acid ---

Dodecanedioic acid ---


2.6 Nitrogen compoundsOrganonitrogen compounds, such as alkanolamines, ben-

zotriazoles, pyrazoles and tetrazols are now employed asthe additives of water-soluble metal working fluids. Vari-ous attempts to prepare high performance additives fromthese nitrogen compounds have recently been made, andmany patents are known. Some of them are briefly men-tioned as follows.

Diamines with such a structure as (XIII) in Fig. 6 aregood in the anti-corrosion effect for aluminum, copper andother metals 22). Additives containing pyrazole compounds

(XIV) show excellent anti-rust and anti-corrosion proper-ties for aluminum, magnesium and an alloy of Al and Mg23).An additive containing compounds (XV) can inhibit corro-sions of tanks composed of aluminum and aluminumalloys24). Tetrazole compounds such as compound (XVI) canbe used as an anti-corrosion inhibitor for an article of castaluminum 25). 2-Mercaptobenzothiazoles (compound XVII)are suitable for water-soluble metal working fluids for alu-minum and other metals26). It is reported that water-solu-ble fluids containing a Schiff's base (XVIII) are good forhigh speed grinding of aluminum, copper, tungsten and

5J. Oleo Sci. 57, (1) 1-10 (2008)

Fig. 4 Preparation of Diels-Alder Product (X)16). Fig. 5 Structures of Polymers (XI) and (XII)17).

Fig. 6 Structures of Various Nitrogen Compounds 22-27).

S. Watanabe

titanium. For example, N, N-bis(1-methyl-3-oxo-butyli-dene)-ethylenediamine and (N-1-methyl-3-oxo-butylidene)amine are reported in the patent 27). Many other patents arepublished.

2.7 Phosphoric estersVarious phosphoric esters are widely used as antistatic

agents of plastics and others 5). It is presumed that phos-phoric esters may be used in commercial water-based cut-ting fluids for the sake of the prevention against corrosionof aluminum materials. For example, ricinoleic acid phos-phoric ester has excellent anti-corrosion property andlubricity 28). We prepared some phosphoric esters by thereaction of phosphorous oxychloride with hydroxyl fattycompounds. Compound (XIX) was prepared from ricinoleic

acid and POCl3 as shown in Fig. 7. Corrosion inhibitor per-formance against an aluminum material was examined foraqueous solutions containing the salts of these phosphoricesters and alkanolamines. The results are summarized inTable 5. The amine salts of compound (XIX) and phospho-ric esters of ricinoleic acid dimer, tetradecylalcohol andhexadecylalcohol showed good anti-corrosion property foraluminum alloy materials 29,30). Recently, a convenientpreparative method of phosphate esters using P2O5 hasbeen reported31).

2.8 Phosphonic acidAmmonium salts of alkylphosphonic acids have been

used as surface active agents 5). Recently, alkylphosphonicacids have been employed for a water-soluble metal work-ing fluid additive 32). In this section the author describesthe evaluations of some alkylphosphonic acids as an alu-minum corrosion inhibitor. Octylphosphonic acid was pre-pared according to the method described in literature 33).Then, diethyl octylphosphonate (XX) was prepared by thethermal reaction of octylbromide with triethylphosphite asshown in Fig. 8. The hydrolysis of (XX) with hydrochloricacid gave octylphosphonic acid (XXI). Hexyl- anddecylphosphonic acids were prepared in a similar fashion.Triethanolamine salts of octylphosphonic acid (XXI) anddecylphosphonic acid showed good anti-corrosion propertyfor aluminum as shown in Table 6 34). These results indicatethat alkylphosphonic acids have anti-corrosion propertyfor aluminum alloy materials.

Alkyldiphosphonic acids were prepared by the reaction

6J. Oleo Sci. 57, (1) 1-10 (2008)

Table 5 Anti-corrosion Characterization of Various Phosphoric Esters of Hydroxy Fatty Compoundsagainst Aluminum Pieces29).

Phosphoric esters Alkanol aminesSolubility for

water

Anti-corrosion property for

aluminum piece

n-Tetradecyl alcohol Triethanolamine Soluble

n-Hexadecyl alcohol Triethanolamine Soluble

Ricinoleic acid

Triethanolamine

Diethanolamine

Monoethanolamine

Soluble

Soluble

Soluble

Ricinoleic acid dimer

Triethanolamine

Diethanolamine

Monoethanolamine

Slightly

Soluble

Slightly

12-Hydroxy stearic acid

Triethanolamine

Diethanolamine

Monoethanolamine

Slightly

Soluble

Slightly

9,10-Dihydroxy-stearic acid

Triethanolamine

Diethanolamine

Monoethanolamine

Soluble

Soluble

Soluble

Fig. 7 Preparation of Phosphoric Ester (XIX) ofRicinoleic Acid 29).


of alkyldibromide with excess triethylphosphite followedby hydrolysis with hydrochloric acid. Diethanolamine saltsof these diphosphonic acids showed good anti-corrosionproperty for aluminum alloy materials as shown in Table 6.However, when the amine salts of these phosphonic acidswere diluted with hard water containing Ca2+, much pre-cipitate was recognized. That is, they have no hard water

tolerance.Some monoesters of octylphosphonic acid (XXI) were

prepared by the reactions of some lower alcohols withoctylphosphonic acid dichloride (XXII) as shown in Fig. 9.Aqueous solutions of diethanolamine salts of monoester(XXIII) with diethyleneglycol monomethyl ether showedboth the good anti-corrosion property for aluminum and a

7J. Oleo Sci. 57, (1) 1-10 (2008)

Table 6 Anti-corrosion Tests and Hard Water Tolerance of Alkylphosphonic Acids and Their Estersfor Aluminum Alloy Materials 34,35).

Sample Concentration %Anti-corrosion tests for

aluminum pH 9.0

Hard water

tolerance

pH 9.0

Hexylphosphonic acid

0.50

0.15

0.05

Octylphosphonic acid (XXI)

0.50

0.15

0.05

Decylphosphonic acid

0.50

0.15

0.05

Octane-1,8-diphosphonic acid

0.50

0.15

0.05

Decane-1,10-diphosphonic acid

0.50

0.15

0.05

Dodecane-1, 12-diphosphonic acid

0.50

0.15

0.05

Ester of octylphosphonic acid (XXI) with

ethylene glycol monomethyl ether

0.50

0.15

0.05

Ester (XXIII) of (XXI) with

diethyleneglycol monomethyl ether

0.50

0.15

0.05

Ester of (XXI) with triethylene glycol

monomethyl ether

0.50

0.15

0.05

Ester of (XXI) with polyethylene glycol

monomethyl ether

0.50

0.15

0.05

Ester of (XXI) with octanol

0.50

0.15

0.05

S. Watanabe

good hard water tolerance (Table 6) 35). In the near future,new aromatic phosphonic acids may be put on the market.A better additive may appear.

2.9 OthersAnti-corrosion additives having water-repellent, anti-

pollution and other properties are now being developed.For example, it is reported that a diluted solution of a mix-ture of 1H, 1H, 2H, 2H-perfluorodecanethiol (0.1%) and afluorinated polymers (0.1%) in a fluorinated solvent (99.8%)has multifunctional effects36). Many other patents are pub-lished.

3 TESTING METHODThe properties of water-soluble cutting fluids to be ana-

lyzed are: surface tension, emulsion stability, pH, chlorine,total sulfur, foamability, corrosion resistance, friction coef-ficient, welding load, microbial resistance, hard water tol-erance and others. Perfect measurements of these perfor-mances are hard. Corrosion tests for aluminum alloy mate-rials are the most important. Practical tests should be per-formed on good samples. As the measurement of weightloss before and after the test requires ten days (240 h),spray (Fog) corrosion test 37,38) is not common for a conve-

nient method. The measurement of pitting potentials issuperior method according to the theoretical considera-tion3941). Discoloration of aluminum surface is discussed inthis review. Then, a convenient test method is described asfollows.Preparation of sample solution: A solution (100 g) was pre-pared by dissolving 0.50 g of test material and 0.5 g of tri-ethanolamine or diethanolamine in deionized water (99.0 g).This solution corresponds to 0.50% solution. The pHs ofthese test solutions were adjusted at 9.0 0.2 by addingacetic acid or sodium hydroxide solution. Similarly, samplesolutions were prepared with city water (Shiga, Japan;hardness 30).Anti-corrosion test of aluminum pieces: Size of test piece ofaluminum alloy (ADC-12)42) is 6 cm 3 cm 0.5 cm. ADC12 is composed of Cu (1.5 ~ 3.5%), Si (9.6 ~ 12.0), Mg (under0.3), Zn (under 1.0), Fe (under 1.3), Mn (under 0.5), Ni (under0.5), Sn (under 0.3) and Al (the rest). The test piece waswashed with acetone, polished with emery paper (#240)and washed with acetone again, and they were immersed 3cm depth in each sample solution (50 ml). After keeping for24 h at 30, the change in color of the surface of the alu-minum piece was checked by visual observation. The cor-rosion-inhibiting effect was evaluated according to the fol-lowing indexing. No appearance of discoloration of aluminum surface A little discoloration of aluminum surface Gray Dark gray

The photographs corresponding to the indexing areshown in Fig. 10. This test is a convenient method for thepractical application in a factory.

Hard water tolerance tests were performed according tothe method reported in literature35).

A number of investigations on the inhibition mechanismof aluminum corrosion are known. For example, the follow-ing papers describe the aluminum corrosions37,39,43).

8J. Oleo Sci. 57, (1) 1-10 (2008)

Fig. 8 Preparation of Octylphosphonic Acid (XXI)33).

Fig. 9 Preparation of Monoester (XXIII) ofOctylphosphonic Acid with Diethy-leneglycol Monomethyl Ether 35).

Fig. 10 Photographs of Aluminum Pieces. The indexing is , , and fromleft to right35).


4 SUMMARYThe relationship between anti-corrosion and lubricating

properties and chemical structure of organic compoundshas not been well known. For aluminum alloy materials,further elaboration is definitely desirable to elucidate thedependence of anti-corrosion performance on the chemicalstructures of the molecule.

ACKNOWLEDGMENTThe author is indebted to Dr. Yoneshima of NEOS Co. Ltd.for his helpful support.

References1. Yamamoto, A.; Suzuki, O. Cutting fluids and grinding

fluids, Asakura Shoten (1966).2. Hiroi, S.; Yamanaka, Y. Cutting fluids and grinding

fluids, Saiwai Shobo (1982).3. Watanabe, S. Developments in oils and fats, Chapter

4, Derivatives of long chain fatty acids (Hamilton, R.J.ed.) Blacky Academic and Professional (Chapman andHall), pp.95-131 (1955).

4. Watanabe, S. Characteristic properties of water-solu-ble cutting fluids additives for iron materials. J. OleoSci. 56 (8), 385-397 (2007).

5. Suga, K.; Watanabe, S. Yuki Kogyo Kagaku, Yuka-gaku (Industrial Organic Chemistry, Oil Chemistry, inEnglish), Kohdansha,Tokyo, Japan, p.52 (1971).

6. Nanbu, N.; Arimatu, K.; Ito, Y. ; Nanbu, T. JapanPatent Publication 2006-299357 (P2006-299357A) (2006,11, 2).

7. Maeda, A.; Shigehiro, K. Japan Patent Application2000-26802 (P2000-26802A) (2000. 1. 25).

8. Watanabe, S.; Fujita, T.; Suga, K.; Kasahara, K.Antirust and lubricity characteristics of cutting fluidsadditives. Lubrication Engineering 38 (7), 412-415(1982).

9. Takahashi, Y.; Taketome, Y.; Takahashi, K.; Yoshikawa,M. Japan Patent Publication (B2), 2838115 (1998. 10.16).

10. Watanabe, S. New water-soluble cutting fluids addi-tives for aluminum materials, Recent Res. Develop. OilChem. (Pandalai, S.G. ed.) Transworld Research Net-work (India) Vol. 6, pp.23-29 (2003).

11. Yamamoto, S.; Tomoda, H.; Watanabe, S. Japan PatentApplication 2001-119170 (2001. 4. 18).

12. Watanabe, S.; Nakagawa, H.; Ohmori, Y.; Fujita, T.;Sakamaoto, M. Characteristic properties of cuttingfluid additives derived from the derivatives of ricinole-ic acid polymer. J. Am. Oil Chem. Soc. 71 (9), 1003-1006 (1994).

13. Watanabe, S. New water-soluble cutting fluids addi-tives derived from half esters for aluminum materials,Rivista Itali. Sostanze Grasse 80 (6), 397-399 (2003).

14. Tomoda, H.; Watanabe, S. Japan Patent Application2003-36145 (2003. 2. 14).

15. Yamamoto, S.; Tomoda, H.; Watanabe, S. Water-solublemetal working fluids additives derived from the estersof acid anhydrides with higher alcohols for aluminumalloy materials. J. Oleo Sci. 56 (9), 463-469 (2007).

16. Watanabe, S. New water-soluble cutting fluids addi-tives derived from the thermal reaction products ofunsaturated fatty acids with acrylic acid and maleicanhydride. J. Korean Oil Chem. Soc. 20 (4), 372-376(2003).

17. Matushita, T. Japan Patent Publication 2004-43734,(P2004-43734A) (2004. 2. 12).

18. Wakabayashi, Y.; Ogino, R.; Kobayashi, N. JapanPatent Publication 2006-2229 (P2006-2229A), (2006. 1.5).

19. Yamaguchi, S. Japan Patent Publication 1999-264085(1999. 9. 28).

20. Imai, G.; Okamoto, A. Japan Patent Publication 2004-43794 (P2004-43794A) (2004. 2. 12).

21. Yuki, T.; Nishida, M. Japan Patent Publication 2004-2747 (P2004-2747A), (2004. 1. 8).

22. Echigo, M.; Kuwabara, H.; Koyama, T. Japan PatentPublication 2005-113195 (P2005-113195A) (2005. 4. 28).

23. Hashimoto, S.; Rei, G.; Hamanabe, T.; Yagi, H. JapanPatent Publication 2005-133143 (P-2005-133143A),(2005. 5. 28).

24. Nakae, J.; Matushita, T. Japan Patent PublicationHeisei 10-168585, (1998. 6. 23).

25. Fukumura, K.; Maekawa, T. Japan Patent Publication1994-6-184771 (1994. 7. 5).

26. Jyodo, A. Japan Patent Publication 2004-10729(P2004-10729A), (2004. 1. 15).

27. Satoh, T.; Nishioka, A.; Itoh, D. Japan Patent Publica-tion 2004-14813 (P2004-14813A) (2004. 1. 15).

28. Nanbu, N. Japan Patent Publication 2004-67770(P2004-67770A), (2004. 3. 4).

29. Watanabe, S. New water-soluble cutting fluids addi-tives for aluminum materials. Recent Res. Develop. OilChem. 6, 23-29 (2003).

30. Yamamoto, S.; Kohara, I.; Watanabe, S.; Tomoda, H.Japan Patent Publication (P2000-313975A) (2000. 11.14).

31. Taotao, Q.; Xuechuan, W.; Longfang, R. Study on pro-duction of lanonol phosphates by a sustained-releasemethod. J. Surfactants & Detergents 10 (1), 9-12(2007).

32. Hayashi, N.; Mochizuki, K.; Ohsawa, M.; Kaneko, M.;Kanamori, H. Japan Patent Publication 2004-262960(P 2004-262960A) (2004. 9. 24).

33. Fieser, J.F.; Fieser, M. Reagents for Organic Synthsis,

9J. Oleo Sci. 57, (1) 1-10 (2008)

S. Watanabe

John Wiley and Sons, Inc., New York, Vol. 1, p.1212(1967).

34. Watanabe, S. New water-soluble cutting fluids addi-tives from phosphonic acids for aluminum materials,Rivista Italia. Sostanze Grasse 82 (2), 97-99 (2005).

35. Kohara, I.; Tomoda, H.; Watanabe, S. New water-solu-ble metal working fluids additives from phosphonicacid derivatives for aluminum alloy materials. J OleoSci. 56 (10) 527-532 (2007).

36. Fujie, A.; Kawate, A.; Aihara, T. Japan Patent Publi-cation 2006-283180 (P2006-283180A) (2006. 10. 19).

37. Ramachandra, M.; Radhakrishna, K. Microstructure,mechanical properties, wear and corrosion behaviourof Al-Si/FLYASHp composite. Mater. Sci. Technol. 21(11), 1337-1343 (2005).

38. Japanese Industrial Standard, Method of salt spray

testing, JIS Z 2371 (2000).39. Rao, K.S.; Rao, K.P. Corrosion resistance of AA2219

aluminum alloy; Electrochemical polarization andimpedance study. Mater. Sci. Technol. 22 (1), 97-104(2006).

40. Kawato, Y.; Kamiusuki, T.; Watanabe, S. Water-solublemetal working fluids additives derived from the deriva-tives of 3-mercaptopropionic acid. J. Surfactants &Detergents 9 (4), 391-394 (2006).

41. Japanese Industrial Standard, Pitting potential, JISG 0577 (2000).

42. Japanese Industrial Standard, Aluminum alloys diecastings (ADC 12), JIS H 5302 (1990).

43. Seri, M. Kinzokuzairyo no Fushoku to Boushoku noKiso, Seizan-do Shuppan (2006).

10J. Oleo Sci. 57, (1) 1-10 (2008)

Anticorrosion Additive for Metalworking Fluids

Documents

Transcript of Anticorrosion Additive for Metalworking Fluids