iContents
Publishing of the Revised Edition  . ............................................................   viiPreface of Original Japanese Edition  ..........................................................   ixPart 1 Introduction  . ..............................................................................   1
Prologue ................................................................................................... 2
Chapter 1 What are Surfactants ?  ..........................................................   3
Chapter 2 Fundamental Properties and Functions of Surfactants  . .   14(1) Wetting Effect and Penetrating Effect  ................................   21(2) Emulsifying Effect and Dispersing Effect  . .........................   24(3) Foaming Effect  ..................................................................   24(4) Detergency  . ......................................................................   25Part 2 Chemical Structures of Surfactants  ..................................   29Chapter 1 Classification of Surfactants  . ..............................................   30Chapter 2 Nonionic Surfactants  ...........................................................   351. Polyethyleneglycol Type Nonionic Surfactants  ......................   38(1) Alkylphenol Ethylene Oxide Adducts andHigher Alcohol Ethylene Oxide Adducts  ............................   46(2) Polyoxyethylene Fatty Acid Esters (Fatty Acid Ethylene
Oxide Adducts or Polyethyleneglycol Fatty Acid Esters)  ....   54(3) Higher Alkylamine Ethylene Oxide Adducts andFatty Acid Amide Ethylene Oxide Adducts(Polyoxyethylenealkylamines and Polyoxyethylene
Fatty Acid Amides)  ............................................................   56(4) Polypropyleneglycol Ethylene Oxide Adducts(Pluronic Type Nonionic Surfactants or Polyoxyethylene
Polyoxypropylene Glycols)  . ...............................................   582. Polyhydric Alcohol Type Nonionic Surfactants  ......................   59(1) Glycerin Fatty Acid Esters and Pentaerythritol Fatty AcidEsters  ................................................................................   62(2) Sorbitol Fatty Acid Esters and Sorbitan Fatty Acid Esters  ...   64(3) Sucrose Fatty Acid Esters  . ................................................   67(4) Alkyl Polyglucosides  . ........................................................   70(5) Fatty Acid Alkanolamides  ..................................................   703. Summary of Nonionic Surfactants  .........................................   73iiChapter 3 Anionic Surfactants  . ............................................................   751. Carboxylates  .........................................................................   77(1) Soaps  . ...............................................................................   77(2) Polyoxyethylene-Alkyl-Ether Carboxylates  .........................   79(3) Alkyl-Glycol-Ether Carboxylates  . .......................................   802. Salts of Sulfonic Acids (Sulfonates)  .......................................   81(1) Alkylbenzenesulfonates  . ....................................................   81(2) Oil-Soluble Alkylbenzenesulfonates  . ..................................   85(3) a-Olefinsulfonates  ..............................................................   86(4) Alkanoylmethyltaurate (Igepon T Type) Products  ..............   87(5) Dialkyl Sulfosuccinate (Aerosol OT Type) Products  . .........   883. Salts of Carboxylic Acids/Salts of Sulfonic Acids(Carboxylates/Sulfonates)  . ...................................................   904. Salts of Sulfuric Esters (Sulfates)  ..........................................   91(1) Higher Alcohol Sulfates (Higher Alkyl Sulfates)  . ...............   93(2) Higher Alcohol Ethylene Oxide Adduct Sulfates(Higher Alkyl-Ether Sulfates)  . ...........................................   99(3) Sulfated Oils, Sulfated Fatty Acid Esters andSulfated Fatty Acids  .........................................................   100
(4) Sulfated Olefins  ...............................................................   1045. Salts of Phosphoric Esters (Phosphates)  .............................   105(1) Higher Alcohol Phosphates(Salts of Higher Alkyl Phosphates)  ..................................   105(2) Salts of Higher Alcohol Ethylene Oxide Adduct
Phosphates (Salts of Higher Alkyl-Ether Phosphates)  ......   106(3) Salts of Dithiophosphates (Dithiophosphates)  ..................   1076. Summary of Anionic Surfactants  .........................................   107Chapter 4 Cationic Surfactants  . .........................................................   1091. Amine Salt Type Cationic Surfactants  . ................................   114
(1) Amine Salt Type Cationic Sufactants Derived from HigherAlkylamines  .....................................................................   116
(2) Amine Salt Type Cationic Surfactants Derived from Lower
Alkylamines  .....................................................................   1172. Quaternary Ammonium Salt Type Cationic Surfactants  .......   121(1) Quaternary Ammonium Salt Type Cationic Surfactants
Derived from Higher Alkylamines  . ..................................   122(2) Quaternary Ammonium Salt Type Cationic Surfactants
Derived from Lower Alkylamines  .....................................   1243. Summary of Cationic Surfactants  ........................................   126Chapter 5 Amphoteric Surfactants  .....................................................   129

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1. Amino Acid Type Amphoteric Surfactants  ...........................   1312. Betaine Type Amphoteric Surfactants  .................................   1343. Summary of Amphoteric Surfactants  ...................................   136Chapter 6 Relationship Between Chemical Structures ofSurfactants and Their Physical Properties  .....................   137
(1) Relationship Between Hydrophilic and Hydrophobic
Properties of Surfactants (HLB)  . .....................................   139
(2) Relationship Between Properties of Surfactants andType of Hydrophilic Groups  . ...........................................   145
(3) Effect of Lipophilic (Hydrophobic) Properties ofSurfactants on Their Essential Characteristics  .................   149
(4) Relationship Between Properties of Surfactants andType of Hydrophobic Groups  . .........................................   153
(5) Relationship Between Properties of Surfactants andShape or Molecular Weight  . ............................................   156
(6) Summary of Relationship Between ChemicalStructures and Property  . .................................................   162

Part 3 Fundamental Properties of Surfactants andTheir Applications  ................................................................   165Chapter 1 Wetting Agents and Penetrating Agents  . .........................   166
(1) Nature of Solution and Type of Penetrating Agent  ...........   167
(2) Penetrating Agents for Neutral Solutions(General Purpose Penetrating Agents)  .............................   169
(3) Specialty Penetrating Agents  ...........................................   177
(4) Rewetting Agents  . ...........................................................   183Chapter 2 Foaming Agents and Defoaming Agents  ..........................   186
(1) Foaming Agents and Foam Stabilizers  .............................   186
(2) Defoaming Agents  ...........................................................   194Chapter 3 Emulsifying, Dispersing and Solubilizing Agents  ...........   200(1) Methods of Selecting Emulsifying and Dispersing Agents  . .   201(2) Methods of Emulsification  ...............................................   211
(3) Applications of Emulsifying Agents, Dispersing Agents, andSolubilizing Agents  ..........................................................   216Chapter 4 Detergents  . .........................................................................   232
(1) Detergency of Surfactants  ...............................................   232(2) Method for Measuring Detergency  ..................................   233
(3) Types of Detergents and Their Properties  .......................   235
(4) Effects of Builders and Other Additives  ...........................   241
(5) Adsorption of Detergents on Textile Fibers  . ....................   241

iv(6) Applications of Detergents  ...............................................   242

Part 4 Secondar y Properties of Surfactants and TheirApplications  . ..........................................................................   267Chapter 1 Lubricants for Fibers  .........................................................   268
(1) Lubricating Effect of Surfactants on Fibers  ......................   268
(2) Friction Coefficient of Fibers  ...........................................   270
(3) Uses of Lubricants for Fibers  . .........................................   272
(4) Relationship Between Chemical Structures ofSurfactants and Their Lubricating Effect on Fibers  ..........   275
(5) Important Surfactants Used as Lubricants for Fibers  .......   280
(6) Summary of Lubricants for Fibers  ...................................   288Chapter 2 Antistatic Agents  ................................................................   289
(1) Buildup of Static Electricity and Necessity ofIts Elimination  .................................................................   290
(2) Principle of Antistatic Agents (Antistatic Effect ofSurfactants) and Methods for Evaluating Antistatic Properties  . .   292
(3) Antistatic Agents for Textile Fibers  . ................................   296
(4) Antistatic Agents for Plastics  ...........................................   301
(5) High-Molecular Antistatic Agents  . ...................................   307Chapter 3 Lubricating Agents for Metals  . .........................................   313
(1) Types of Lubricating Oils and Additives  . .........................   313
(2) Examples of Lubricating Oils  ...........................................   319Chapter 4 Rust Preventive Agents  .....................................................   321
(1) Surfactants Used as Rust Preventive Agents  ....................   321
(2) Examples of Applications of Rust Preventive Agents  ........   323Chapter 5 Leveling Agents and Fixing Agents for Dyeing  ...............   325
(1) Leveling Agents  . .............................................................   325
(2) Dye-Fixing Agents  ...........................................................   328Chapter 6 Hydrophobifying Agents  ....................................................   329
(1) Water-Repellent Agents  . ..................................................   329
(2) Sizing Agents for Paper  ...................................................   333
(3) Flotation Reagents  ...........................................................   336
(4) Other Hydrophobifying Agents  ........................................   337Chapter 7 Antibacterial Agents  ...........................................................   338Chapter 8 Flocculants  . ........................................................................   341
(1) Flocculants Used in Manufacturing Processes of
Various Industries  . ..........................................................   344
(2) Flocculants Used for Industrial Waste Water Treatment  . .   344
(3) Flocculants Used for Sewage Treatment  ..........................   345

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(4) Drainage and Retention Improvers for Papermaking  ........   346

Part 5 Safety of Surfactants and Their Influences onEnvironment  . .........................................................................   347Chapter 1 Influences of Surfactants on Humans and Animals  . .....   348
(1) Oral Toxicity  ...................................................................   348
(2) Eye Irritation  ...................................................................   349
(3) Skin Irritation  ..................................................................   351
(4) Hemolytic Effect  . ............................................................   353
(5) Acute Toxicity to Fish  . ....................................................   354
(6) Endocrine Disruption (Environmental Hormone Effect)  ....   355Chapter 2 Environmental Impact of Surfactants and Its Control  . ..   357
(1) Oxygen Demand of Surfactants in Waste Water  ...............   357
(2) Biodegradability of Surfactants  ........................................   359
(3) Application of Surfactants for Pollution Control  . ..............   362

Epilogue  . ...............................................................................................   364Indexvii

Publishing of the Revised Edition
This is the English translation of the newly revised edition of Introduction
to Surfactants (Kaimen Kasseizai Nyumon in Japanese), which was publishedin March 2007. Intended as a systematic introductory guide to surfactants,
covering everything from basic principles to practical applications, theJapanese version has always been well received for their great clarity by thoseembarking on the study of surfactants and by those concerned with their actualuse.
The original Japanese version has been revised and reprinted repeatedly
ever since it was first published in November 1963. With the retirement ofthe author, Dr. Takehiko Fujimoto (former chairman of the board of Sanyo
Chemical Industries, ltd.), in June 2004, the book was expected to goout of print. However, due to the enthusiasm of our readers and their wishes
for continued publication, it was decided to enlist the support of our Research
Division and Public Relations Dept., and to carry out revisions for a new edition.
The main thrust of the newly revised Japanese version, is the shift fromreferencing alkylphenol EO (ethylene oxide) adducts to replacement products.
Since the earlier revised edition of the original volume that was published in 1981,
the field of surfactants has seen remarkable technological advances, and thephenomenon of endocrine disruption has come to be recognized as a major issue.
Important nonionic surfactant raw materials such as alkylphenol EO
adducts are derived from nonylphenol (NP) and octylphenol (OP) which
manifest estrogen-like effects in the bodies of animals.
Although alkylphenol EO adduct itself is not an endocrine disruptor,
upon biodegrading in the environment, NP and OP are produced. In orderto address this problem, replacement product development programs andvoluntary bans on water-polluting applications have been undertaken by theconcerned industries. As a result, NP/OP environmental contamination has
now been ameliorated to the extent that virtually no risk remains.
As alkylphenol EO adducts have excellent functionality and have therefore
been used widely in surfactants, these substances were discussed throughout
the original version of this book, and numerous references were made to theirdiverse applications. In light of these developments, it was decided that thecontents of the original edition no longer reflected current world conditions,and a revised Japanese version was prepared in 2007. While the main thrustof this revision was this shift from also alkylphenol EO adducts to replacement
products, the following three guidelines were implemented: 1. to update theclassification of surfactants to be in line with the standards accepted by theJapan Surfactant Industry Association (JSIA); 2. to replace old data regarding
safety and other concerns with data released by the JSIA ; and 3. to reassess

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the appropriateness of the terminology in light of current conditions.
In response to requests from English language readers, an English
translation of Introduction to Surface Active Agents (Surfactants) was firstpublished in 1985. When the latest Japanese revisions were prepared in 2007, it
was decided that the changes in the Japanese version should also be reflected
in a new English version.
As the development of surfactants that substitute other substances foralkylphenol EO adducts is still ongoing, it is inevitable that this revised version
will become outdated. Even so, it is my earnest wish that the reader will findthis volume of use in understanding surfactants and the circumstances of theirproduction and use.
I would like to express my deep gratitude to Dr. Tetsuo Morino (a veteranof our Public Relations Dept.), and to everyone in our Research Division andPublic Relations Dept. for their cooperation in realizing the revision of thisbook.
March 2010
Tetsuo Kakehi Supervisor for the New Edition
Adviser, Sanyo Chemical Industries, Ltd.

ix

Preface of Original Japanese Edition
The present book is a complete rewrite of the book entitled Introduction
to Surfactants (Kaimen Kasseizai Nyumon in Japanese) written by Koich Isodaand Dr. Takehiko Fujimoto, and published in November 1963.
In response to favorable public reception, the original book has run into its
6th edition since first published in 1963. The book was revised by Dr. Fujimoto
several times, but such partial revisions were not sufficient to keep up withthe remarkable progress of technology and society in those years. In 1973,
the book was rewritten completely with the title changed to Introduction toSurfactants, New Edition, and it was supplemented and revised in 1976 andagain in 1981.
In 1963, the Japanese economy was in the early stage of high growth, andwhat are called the golden sixties were just about to bloom. The year of 1973,
when the new rewritten edition was published, saw the real beginning of theseventies, the transition period when social concern moved from quantity toquality + quality.
In the 1980s, with the transition period of the 1970s over, demands arebeing made on industries that they have their own resources of creativity.
The importance of surfactants in a broad sense is increasing more and morethese days in response to the industrial tendency to place emphasis on brainintensive operations rather than mass production, and, in the case of thechemical industry, on specialty chemicals rather than heavy chemicals.
Therefore, even in the case of this kind of book of introduction, it is reallydifficult for a single author to cover the full-grown technical area of surfactants
as it is today. In spite of the skillful support of the research chemists of ourcompany in each specific field, I cannot help conceding that the present bookis far from being “adequate.”
I hope that, though the book is not adequate enough, it will serve you as aspringboard for jumping into the more concrete realm of surfactants, namely,
the realm of their practical applications. I believe that actual practice should
be our excellent teacher, a far better one than any book can be.
It is an unanticipated pleasure for me to be able to revise the book at
the beginning of the 1980s. I wish to take this opportunity of expressing mysincere thanks to the staff of Research Division and Public Relations Dept. ofSanyo Chemical Industries, Ltd. for their invaluable assistance.
July 1981
Dr. Takehiko Fujimoto