Journal of Oleo Science

Copyright 2008 by Japan Oil Chemists Society

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

REVIEW

Preparations and Properties of Anti-corrosion

Additives of Water-soluble Metal Working
Fluids for Aluminum Alloy Materials
Shoji Watanabe
Akitsu 1-3-5-502, Narashino, Chiba 275-0025 (Professor Emeritus of Chiba University; Former: Department of Applied Chemistry, Faculty of
Engineering, Chiba University, Yayoicho, Inage-ku, Chiba, 263-0085 JAPAN)

Abstract: This short review describes various types of anti-corrosion additives of water-soluble metal
working fluids for aluminum alloy materials. It is concerned with synthetic additives classified according
to their functional groups; silicone compounds, carboxylic acids and dibasic acids, esters, Diels-Alder
adducts, various polymers, nitrogen compounds, phosphoric esters, phosphonic acids, and others. Testing
methods for water-soluble metal working fluids for aluminum alloy materials are described for a practical
application in a laboratory.
Key words: water-soluble metal working fluids, additives, aluminum alloy materials, anti-corrosion property, testing
methods

1 INTRODUCTION
A 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 in
metal working and cutting for irons are known. However,
the review of those for aluminum alloy materials is quite
few. Aluminum materials are apt to be blackish by mechanical processing, owing to corrosion of aluminum. Various
attempts to prepare high performance additives for aluminum materials have recently been made. Many patents
on corrosion inhibitors in metal working and cutting of aluminum materials are known. Usually water-soluble cutting
fluids consist of many components. However, the detailed
compositions of the commercial products have not been
known. The most important additive is a surface active
agent having anti-corrosion and other useful properties.
The surface active agent is called a metal working fluid
additive. This short review article describes preparations
and properties of new types of metal working fluids additives which have been developed in our laboratory and
reported in literatures.

2 METAL WORKING FLUIDS ADDITIVES FOR ALUMINUM ALLOY MATERIALS

This chapter describes our evaluation of various additives derived from a variety of organic compounds for
water-soluble metal working fluids of aluminum alloy materials. Alkanolamines such as triethanolamine or
diethanolamine are used to dissolve acidic ingredients into
water, to increse anti-microbial activity of the fluids, and
for other purposes. Aluminium alloy materials are apt to be
blackish in alkaline media (pH=9.0). Various corrosion
inhibitors are added to cutting fluids. The use of triethanolamine or diethanolamine salts gave the best results
in our experiments for anti-corrosion and lubricity characteristics of cutting fluid additives.
2.1 Silicone compounds
It is well known that sodium metasilicate is effective for
corrosion inhibitor of aluminum alloy materials 5). However,
solubility of sodium metasilicate in water is poor. The longterm safe keeping of the fluids containing sodium metasilicate is difficult because of the precipitation of inorganic
compounds. Recently, it has been reported that compound
(II) in Fig. 1, which is prepared from water-soluble silicate

Correspondence to: Shoji Watanabe, Akitsu 1-3-5-502, Narashino, Chiba 275-0025, JAPAN
E-mail: s-wata@mui.biglobe.ne.jp
Accepted September 26, 2007 (received for review August 13, 2007)

Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online

http://jos.jstage.jst.go.jp/en/

S. Watanabe

(I) and alkali, is very effective as an anti-corrosion additive

for aluminum metal 6) . A mixture of compound (II), triethanolamine and water showed good anti-corrosion property for aluminum alloy materials. As other patents,
polyalkyl {(N-aminoalkyl) iminoalkyl} siloxane 7) and others
are known. In the near future, new silicone surface active
agents may be put on the market. A better additive may be
prepared.
2.2 Carboxylic acids and dibasic acids
p-t-Butylbenzoic acid 8) and dodecanedioic acid 4) have
excellent anti-corrosion properties for iron materials. It is
reported that the metal working fluid composed of t-butylbenzoic acid, dodecenylsuccinic ester, morpholine and benzotriazole shows excellent anti-corrosion properties for
aluminum, copper and iron materials 9).
The dibasic acids higher than dodecanedioic acid have
not been examined regarding their properties as the corrosion inhibitor against aluminum alloy materials. Interestingly, the author and coworkers have found that the salts
of dibasic acid (C16 , C18 and C20) with an amine show
good anti-corrosion property against aluminum alloy. For
example, the aqueous solution of 1,18-octadecanedioic acid
with 2-amino-2-methyl-1-propanol showed good anti-corrosion property for aluminum alloy materials. Similarly, the
salts of 1,16-hexadecanedioic acid and 1, 20-eicosanedioic
acid with 2-amino-2-methyl-1-propanol showed anti-corrosion property for aluminum alloys. The results are shown
in Table 1 10, 11).
2.3 Esters
It is known that esters of higher hydroxy fatty acids
have anti-corrosion properties for iron materials 12). In this
section the author describes the evaluations of some esters
as an aluminum corrosion inhibitor. Dodecanedioic acid
anhydride (IV) was prepared by the dehydration reaction of
dodecanedioic acid (III) with acetic anhydride as shown in
Fig. 2. A variety of half esters of (III) were prepared from
the reaction of (IV) and various hydroxyl compounds. For

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

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

Table 1 Anti-corrosion Property of Higher Dibasic Acids for Aluminum Alloy

Materials 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

Testing method is described in the Section 3.

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

Water-soluble Metal Working Fluids Additives

example, compound (VI) was obtained from (IV) and

trimethylolpropane (V). Triethanolamine salt of the half
ester (VI) showed good anti-corrosion properties for aluminum as shown in Table 2. Monoesters (e.g., glycerol,
trimethylolpropane, phytanetriol, 1,4-cyclohexanediol and
ricinoleic acid tetramer) of (III) exhibited good anti-corrosion behavior for aluminum 13, 14).
The long use of water-soluble metal working fluids is apt
to produce precipitates owing to Ca2+ and Mg2+ in hard
water. The additives which possess both the anti-corrosion

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

Anhydride 15).
Table 2 Anti-corrosion Tests of Half Esters for
Aluminum 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

Dodecanedioic acid anhydride

Glycerin (2:1)

8.74

Dodecanedioic acid anhydride

Ricinoleic acid tetramer (1:1)

8.61

Dodecanedioic acid anhydride

Phytanetriol (2 :1)

8.87

Dodecanedioic acid anhydride

1,4-Cyclohexanediol (1.5 :1)

8.53

Adipic acid anhydride

Phytanetriol (2:1)

8.72

Glutaric acid anhydride

Trimethylolpropane (2:1)

8.2

Glutaric acid anhydride

Monostearin (1.5:1)

8.69

Glutaric acid anhydride

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

property for aluminum and a good hard water tolerance

have not been reported. The author and co-workers developed the additives having both of them. A variety of half
esters and diesters were prepared from the reactions of
various hydroxyl compounds with some acid anhydrides.
For example, a mixture of tetrahydrofuran oligomer
(PTMG) (VII) and maleic anhydride was heated to give
diester (VIII) in high yields (Fig. 3). The diester of PTMG
and polybutylene oxide (PBO) with maleic anhydride
showed both anti-corrosion properties for aluminum alloy
material and hard water tolerance (Table 3) 15). New esters
having anti-corrosion and other useful properties will
appear in near future.
2.4 Diels-Alder adducts
It is known that oleic acid, ricinoleic acid and dehydrated castor oil fatty acids have a considerable anti-corrosion
property for aluminum material. In this section the author
describes the evaluations of some thermal products of
unsaturated fatty acids with acrylic acid and maleic anhydride as an aluminum corrosion inhibitor. A mixture of
dehydrated ricinoleic acid (IX) with acrylic acid in the
presence of anhydrous aluminum chloride was heated at
140 to give a Diels-Alder adduct (X) with various byproducts (Fig. 4). The main product was assumed to be the
corresponding Diels-Alder adduct. Similarly, other DielsAlder products were prepared from the reaction of (IX)
with some dienophiles. Triethanolamine salt of compound
(X) showed good anti-corrosion properties for aluminum as
shown in Table 4. The thermal adduct of (IX) with maleic
anhydride and that of linoleic acid with acrylic acid or
maleic anhydride exhibited good anti-corrosion behavior
for aluminum, respectively. Interestingly, the anti-corrosion properties of these thermal adducts were better than
those of (IX) and linoleic acid. These results suggest that
the presence of the bulky alkyl group in higher unsaturated
fatty acid molecule enhances their anti-corrosion property
for aluminum material 16).

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

S. Watanabe

Table 3 Reaction Products of Various Alcohols with Maleic Anhydride and Their Anti-corrosion Tests for
Aluminum and Hard Water Tolerance 15).
Entry
No.

Alcohols

Acid
anhydride

Molar
ratio

Anti-corrosion test of
aluminum After 24 h

Hard water tolerance

After 24 h

PTMG 650

MA

11

PTMG 650

MA

12

PTMG 1000

MA

11

PTMG 1000

MA

12

PBO 650

MA

12

PBO 1000

MA

12

Ricinoleic acid

NPG

Tall oil fatty acids

Undecylenic acid

Dodecanoic acid

Numbers of 650 and 1000 are average molecular weights of PTMG and PBO.
Hard water tolerance tests were performed according to the references method 35).
MA is maleic anhydride.

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

---

2.5 Various polymers

Recently, homopolymers and copolymers are used for
metal working fluids additives. For example, water soluble
metal working fluids containing compounds (XI) or (XII) in
Fig. 5 are used as cutting and grinding fluids for aluminum
materials 17).
The following compounds for corrosion inhibitors and
processing fluids have been reported; maleic acid homo-

polymers or copolymers 18), graft copolymers of polyether

and monoethylenic unsaturated carboxylic acids 19), alkylene oxide adducts to fatty alcohols (weight average molecular weight = 1000 10,000) 20), and oil-soluble copolymers
(molecular weight > 3000) having a special structure 21) and
many others.

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

Water-soluble Metal Working Fluids Additives

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).

2.6 Nitrogen compounds

Organonitrogen compounds, such as alkanolamines, benzotriazoles, pyrazoles and tetrazols are now employed as
the additives of water-soluble metal working fluids. Various attempts to prepare high performance additives from
these nitrogen compounds have recently been made, and
many patents are known. Some of them are briefly mentioned as follows.
Diamines with such a structure as (XIII) in Fig. 6 are
good in the anti-corrosion effect for aluminum, copper and
other metals 22). Additives containing pyrazole compounds

(XIV) show excellent anti-rust and anti-corrosion properties for aluminum, magnesium and an alloy of Al and Mg 23).
An additive containing compounds (XV) can inhibit corrosions of tanks composed of aluminum and aluminum
alloys 24). Tetrazole compounds such as compound (XVI) can
be used as an anti-corrosion inhibitor for an article of cast
aluminum 25). 2-Mercaptobenzothiazoles (compound XVII)
are suitable for water-soluble metal working fluids for aluminum and other metals 26). It is reported that water-soluble fluids containing a Schiff's base (XVIII) are good for
high speed grinding of aluminum, copper, tungsten and

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

S. Watanabe

titanium. For example, N, N-bis(1-methyl-3-oxo-butylidene)-ethylenediamine and (N-1-methyl-3-oxo-butylidene)

amine are reported in the patent 27). Many other patents are
published.
2.7 Phosphoric esters
Various phosphoric esters are widely used as antistatic
agents of plastics and others 5). It is presumed that phosphoric esters may be used in commercial water-based cutting fluids for the sake of the prevention against corrosion
of aluminum materials. For example, ricinoleic acid phosphoric ester has excellent anti-corrosion property and
lubricity 28). We prepared some phosphoric esters by the
reaction of phosphorous oxychloride with hydroxyl fatty
compounds. Compound (XIX) was prepared from ricinoleic

Fig. 7 Preparation of Phosphoric Ester (XIX) of

Ricinoleic Acid 29).

acid and POCl3 as shown in Fig. 7. Corrosion inhibitor performance against an aluminum material was examined for
aqueous solutions containing the salts of these phosphoric
esters and alkanolamines. The results are summarized in
Table 5. The amine salts of compound (XIX) and phosphoric esters of ricinoleic acid dimer, tetradecylalcohol and
hexadecylalcohol showed good anti-corrosion property for
aluminum alloy materials 29,30) . Recently, a convenient
preparative method of phosphate esters using P2O5 has
been reported 31).
2.8 Phosphonic acid
Ammonium salts of alkylphosphonic acids have been
used as surface active agents 5). Recently, alkylphosphonic
acids have been employed for a water-soluble metal working fluid additive 32). In this section the author describes
the evaluations of some alkylphosphonic acids as an aluminum corrosion inhibitor. Octylphosphonic acid was prepared according to the method described in literature 33).
Then, diethyl octylphosphonate (XX) was prepared by the
thermal reaction of octylbromide with triethylphosphite as
shown in Fig. 8. The hydrolysis of (XX) with hydrochloric
acid gave octylphosphonic acid (XXI). Hexyl- and
decylphosphonic acids were prepared in a similar fashion.
Triethanolamine salts of octylphosphonic acid (XXI) and
decylphosphonic acid showed good anti-corrosion property
for aluminum as shown in Table 6 34). These results indicate
that alkylphosphonic acids have anti-corrosion property
for aluminum alloy materials.
Alkyldiphosphonic acids were prepared by the reaction

Table 5 Anti-corrosion Characterization of Various Phosphoric Esters of Hydroxy Fatty Compounds

against Aluminum Pieces 29).
Solubility for
water

Anti-corrosion property for

aluminum piece

Phosphoric esters

Alkanol amines

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

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

Water-soluble Metal Working Fluids Additives

tolerance.
Some monoesters of octylphosphonic acid (XXI) were
prepared by the reactions of some lower alcohols with
octylphosphonic acid dichloride (XXII) as shown in Fig. 9.
Aqueous solutions of diethanolamine salts of monoester
(XXIII) with diethyleneglycol monomethyl ether showed
both the good anti-corrosion property for aluminum and a

of alkyldibromide with excess triethylphosphite followed

by hydrolysis with hydrochloric acid. Diethanolamine salts
of these diphosphonic acids showed good anti-corrosion
property for aluminum alloy materials as shown in Table 6.
However, when the amine salts of these phosphonic acids
were diluted with hard water containing Ca2+, much precipitate was recognized. That is, they have no hard water

Table 6 Anti-corrosion Tests and Hard Water Tolerance of Alkylphosphonic Acids and Their Esters
for Aluminum Alloy Materials 34,35).
Hard water
tolerance
pH 9.0

Concentration %

Anti-corrosion tests for

aluminum pH 9.0

Hexylphosphonic acid

0.50
0.15
0.05

0.50
0.15
0.05

Octylphosphonic acid (XXI)

0.50
0.15
0.05

Decylphosphonic acid

Octane-1,8-diphosphonic acid

0.50
0.15
0.05
0.50
0.15
0.05

Decane-1,10-diphosphonic acid

0.50
0.15
0.05

Dodecane-1, 12-diphosphonic acid

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

Sample

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

S. Watanabe

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

Fig. 10 Photographs of Aluminum Pieces.

The indexing is , , and from
left to right 35).

Fig. 9 Preparation of Monoester (XXIII) of

Octylphosphonic Acid with Diethyleneglycol Monomethyl Ether 35).
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 Others
Anti-corrosion additives having water-repellent, antipollution and other properties are now being developed.
For example, it is reported that a diluted solution of a mixture of 1H, 1H, 2H, 2H-perfluorodecanethiol (0.1%) and a
fluorinated polymers (0.1%) in a fluorinated solvent (99.8%)
has multifunctional effects 36). Many other patents are published.

3 TESTING METHOD
The properties of water-soluble cutting fluids to be analyzed are: surface tension, emulsion stability, pH, chlorine,
total sulfur, foamability, corrosion resistance, friction coefficient, welding load, microbial resistance, hard water tolerance and others. Perfect measurements of these performances are hard. Corrosion tests for aluminum alloy materials are the most important. Practical tests should be performed on good samples. As the measurement of weight
loss 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 is

superior method according to the theoretical consideration 3941). Discoloration of aluminum surface is discussed in
this review. Then, a convenient test method is described as
follows.
Preparation of sample solution: A solution (100 g) was prepared by dissolving 0.50 g of test material and 0.5 g of triethanolamine or diethanolamine in deionized water (99.0 g).
This solution corresponds to 0.50% solution. The pHs of
these test solutions were adjusted at 9.0 0.2 by adding
acetic acid or sodium hydroxide solution. Similarly, sample
solutions were prepared with city water (Shiga, Japan;
hardness 30).
Anti-corrosion test of aluminum pieces: Size of test piece of
aluminum alloy (ADC-12) 42) is 6 cm 3 cm 0.5 cm. ADC
12 is composed of Cu (1.5 ~ 3.5%), Si (9.6 ~ 12.0), Mg (under
0.3), Zn (under 1.0), Fe (under 1.3), Mn (under 0.5), Ni (under
0.5), Sn (under 0.3) and Al (the rest). The test piece was
washed with acetone, polished with emery paper (#240)
and washed with acetone again, and they were immersed 3
cm depth in each sample solution (50 ml). After keeping for
24 h at 30, the change in color of the surface of the aluminum piece was checked by visual observation. The corrosion-inhibiting effect was evaluated according to the following indexing.
No appearance of discoloration of aluminum surface
A little discoloration of aluminum surface
Gray
Dark gray
The photographs corresponding to the indexing are
shown in Fig. 10. This test is a convenient method for the
practical application in a factory.
Hard water tolerance tests were performed according to
the method reported in literature 35).
A number of investigations on the inhibition mechanism
of aluminum corrosion are known. For example, the following papers describe the aluminum corrosions 37,39,43).

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

Water-soluble Metal Working Fluids Additives

4 SUMMARY
The relationship between anti-corrosion and lubricating
properties and chemical structure of organic compounds
has not been well known. For aluminum alloy materials,
further elaboration is definitely desirable to elucidate the
dependence of anti-corrosion performance on the chemical
structures of the molecule.

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

References
1. 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 and
Hall), pp.95-131 (1955).
4. Watanabe, S. Characteristic properties of water-soluble cutting fluids additives for iron materials. J. Oleo
Sci. 56 (8), 385-397 (2007).
5. Suga, K.; Watanabe, S. Yuki Kogyo Kagaku, Yukagaku (Industrial Organic Chemistry, Oil Chemistry, in
English), Kohdansha,Tokyo, Japan, p.52 (1971).
6. Nanbu, N.; Arimatu, K.; Ito, Y. ; Nanbu, T. Japan
Patent Publication 2006-299357 (P2006-299357A) (2006,
11, 2).
7. Maeda, A.; Shigehiro, K. Japan Patent Application
2000-26802 (P2000-26802A) (2000. 1. 25).
8. Watanabe, S.; Fujita, T.; Suga, K.; Kasahara, K.
Antirust and lubricity characteristics of cutting fluids
additives. 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 additives for aluminum materials, Recent Res. Develop. Oil
Chem. (Pandalai, S.G. ed.) Transworld Research Network (India) Vol. 6, pp.23-29 (2003).
11. Yamamoto, S.; Tomoda, H.; Watanabe, S. Japan Patent
Application 2001-119170 (2001. 4. 18).
12. Watanabe, S.; Nakagawa, H.; Ohmori, Y.; Fujita, T.;
Sakamaoto, M. Characteristic properties of cutting
fluid additives derived from the derivatives of ricinoleic acid polymer. J. Am. Oil Chem. Soc. 71 (9), 10031006 (1994).

13. Watanabe, S. New water-soluble cutting fluids additives derived from half esters for aluminum materials,
Rivista Itali. Sostanze Grasse 80 (6), 397-399 (2003).
14. Tomoda, H.; Watanabe, S. Japan Patent Application
2003-36145 (2003. 2. 14).
15. Yamamoto, S.; Tomoda, H.; Watanabe, S. Water-soluble
metal working fluids additives derived from the esters
of acid anhydrides with higher alcohols for aluminum
alloy materials. J. Oleo Sci. 56 (9), 463-469 (2007).
16. Watanabe, S. New water-soluble cutting fluids additives derived from the thermal reaction products of
unsaturated fatty acids with acrylic acid and maleic
anhydride. 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. Japan
Patent 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 200443794 (P2004-43794A) (2004. 2. 12).
21. Yuki, T.; Nishida, M. Japan Patent Publication 20042747 (P2004-2747A), (2004. 1. 8).
22. Echigo, M.; Kuwabara, H.; Koyama, T. Japan Patent
Publication 2005-113195 (P2005-113195A) (2005. 4. 28).
23. Hashimoto, S.; Rei, G.; Hamanabe, T.; Yagi, H. Japan
Patent Publication 2005-133143 (P-2005-133143A),
(2005. 5. 28).
24. Nakae, J.; Matushita, T. Japan Patent Publication
Heisei 10-168585, (1998. 6. 23).
25. Fukumura, K.; Maekawa, T. Japan Patent Publication
1994-6-184771 (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 Publication 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 additives for aluminum materials. Recent Res. Develop. Oil
Chem. 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 production of lanonol phosphates by a sustained-release
method. 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,

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

S. Watanabe

34.

35.

36.
37.

38.

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

(1967).
Watanabe, S. New water-soluble cutting fluids additives from phosphonic acids for aluminum materials,
Rivista Italia. Sostanze Grasse 82 (2), 97-99 (2005).
Kohara, I.; Tomoda, H.; Watanabe, S. New water-soluble metal working fluids additives from phosphonic
acid derivatives for aluminum alloy materials. J Oleo
Sci. 56 (10) 527-532 (2007).
Fujie, A.; Kawate, A.; Aihara, T. Japan Patent Publication 2006-283180 (P2006-283180A) (2006. 10. 19).
Ramachandra, M.; Radhakrishna, K. Microstructure,
mechanical properties, wear and corrosion behaviour
of Al-Si/FLYASHp composite. Mater. Sci. Technol. 21
(11), 1337-1343 (2005).
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 and
impedance study. Mater. Sci. Technol. 22 (1), 97-104
(2006).
40. Kawato, Y.; Kamiusuki, T.; Watanabe, S. Water-soluble
metal working fluids additives derived from the derivatives of 3-mercaptopropionic acid. J. Surfactants &
Detergents 9 (4), 391-394 (2006).
41. Japanese Industrial Standard, Pitting potential, JIS
G 0577 (2000).
42. Japanese Industrial Standard, Aluminum alloys die
castings (ADC 12), JIS H 5302 (1990).
43. Seri, M. Kinzokuzairyo no Fushoku to Boushoku no
Kiso, Seizan-do Shuppan (2006).

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