SURFACTANTS

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introduction
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Are surfactants of natural or synthetic origin ?

They can be either. Surfactants from natural origin (vegetable or animal) are known as oleo-chemicals and are derived from sources such as palm oil or tallow. Surfactants from synthetic origin are known as petro-chemicals and are derived from petroleum.

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What does surfactant do ?

Water & Oil are mortal enemies Surface Tension Force between two liquids

Surfactants acts as clamp binding Water & Oil are together 8/19/12

How does surfactant work?

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Cleaning/Detergency
Real Soil Composition

How does cleaning take place ?

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Required Effects when Cleaning

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How Surfactants Work

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Surfactant
Definition
Surface Active Agent

Substance which reduces surface/interfacial tension between two phases Compounds having tendency to gather around the interface between two different materials by altering the properties of interface remarkably

Serves as good mediator to settle dispute between two phases which are not friends

Water: surface tension = 72 dynes/cm Water + 1.0% Surfactant: Surface tension = 20 40 dynes/cm

types
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INTRODUCTION

Anionic (-ve) Cationic (+ve) Zwitterionic Nonionic (No charge)

Cetylpyridinium bromide
O

Sodium dodecylsulfate (SDS)

O S - + O Na O + N BrO O

(Charge depends on pH)

Dipalmitoylphosphatidylcholine (lecithin)

OCH 2CH2N(CH3)3+ P OO

O
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OH

Polyoxyethylene(4) lauryl ether (Brij 30)

Types of Surfactants

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Ionic Surfactants
Anionic Surfactants
Carboxylates

Soa ps

LABS

Alkyl benzene Sulphonates

FAS 8/19/12

Ionic Surfactants
Anionic Surfactants
Sulfosuccinate Diester

Sulfosuccinate Monoester

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Ionic Surfactants: Uses

Anionic Surfactants

Cleansing Formulation

Shampoo Hand wash Bath gels Tooth Paste Soaps & Detergents

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Cationic Surfactants(1)

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Cationic Surfactants(2)

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Important Property
Substantivity

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Cationic Surfactants

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Ionic Surfactants
Amphoteric Surfactants
Cocobetaine (CB)

Cocoamidopropylbetaine ( CAPB)

C H N 3 + C H 3 C O N H ( C H 2 )3

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C H 2 C CO HO N 3 + C H 3

C H 2 C O

Uses :

Amphoteric Surfactants

Betaines are used in personal care products e.g. hair shampoos, liquid soaps, and cleansing lotions. All-purpose cleaning agents, hand dishwashing agents, and special textile detergents..

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Nonionic Surfactants

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Nonionic Surfactants

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Water Solubility of Nonionics

Reason

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Cloud Point

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Effect of moles of EO on Cloud Points of Nonionic

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Influence of Cloud Point on

Soil Removal

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HLB Hydrophilic Lipophilic Balance

HLB is a means of expressing the hydrophilic property of surfactants in figures

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HLB Value
Significance
HLB Value 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

Water in oil emulsifier

Oil in water Emulsifiers

Use Wetting Agents Detergents

Solubilizer

HLB According to Griffin

(only for PEG types)

substantive to skin and hair

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HLB According to Griffin

(only for polyhydric alcohol types)

HLB = 20 ( 1 SV / AV )
Where S V = Sap value of ester of polyhydric alcohol AV = Acid value of fatty acid used Calculation of HLB value of PEG-7-glyceryl-cocoate AV of cocofatty acid = 265 mg KOH/g SV of PEG-7-glyceryl-cocoate = 95
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HLB According to Davis

HLB = 7 + m * Hh + n * Hl
where

m - number of hydrophilic groups in the molecule Hh - Value of the hydrophilic groups n - Number of lipophilic groups in the molecule

Ex : Calculation of HLB of SLES

Hl - Value of the lipophilic groups

Formula of SLES : CH3(CH2)11O (CH2CH2O)2SO3Na HLB = 7 + (1 x 1.3 + 2 x 0.33 + 38.7)+(12 x 0.475) = 42

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Nonionic Surfactants
Properties

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Nonionic Surfactants
Applications

Cleansing agent in detergents Emulsifying agents household & I & I formulations Wetting agents in textile processing, agrochemical formulations

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Contents
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CONTENTS
Selection criteria Types Emulsifiers Foam Stabilizers Wetting agents Lipid Crystal Modifiers Solubilizers/ Dispersing agent Starch Complexers
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Protein Modifiers

Selection criteria
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Selection criteria

Type selection : Anionic, cationic.. Correct solubility for unique application

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terms
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TERMS

CMC Solid Fat Index (SFI) & SFC Span 60/ Span 80 Tween 60/ Tween 80

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Term SOLVENT

Definition The medium in which soil is suspended and carried away from the surface. The customer adds most of the solvent to Simple Green Products- I.E. water Abbreviation for Surface Active Agent,surfactants work at the boundary layer (the interface) between the soil and the solvent. Each molecule of surfactant has a hydrophilic end which is attracted to water, and a hydrophobia end which is attracted to soil. In an effective cleaner/degreaser such as Simple Green, many surfactant molecules attack the soil with their hydrophobic ends, breaking it up into small bits and surrounding it. Their hydrophilic ends then allow the soil to be lifted, suspended, and washed away.

SURFACTANTS

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PENETRATING & WETTING AGENTS EMULSIFIERS SOLUBILIZERS DISPERSANTS

By changing the chemical composition of the hydrophilic and hydrophobic ends of the surfactant molecule, different surfactants with varying degrees of effectiveness can be created. By "punching up" the penetration and wetting ability of the surfactant, more water is able to surround soil particles that would otherwise repel water. Enable surfactants to break up soils (particularly petroleum soils) into smaller droplets that are more easily dispersed throughout the solvent. Enable soils to be dissolved so that they are no longer solid particles, thereby making them easier to break apart. Enable the spreading of particles throughout the solvent and prevent them from readhering to the cleaned surface.

Chelators [ key-laters ] bind up hardness minerals found in water, enabling the other active ingredients to more effectively attack the soils. Chelators can also pull CHELATING AGENTS minerals and metals into solution and, in some extreme precision applications, this is not always desirable.

SAPONIFIERS BUILDERS

Are strong alkaline chemicals that make animal fats soluble in water and more easily washed away. Give the overall solution additional strength to hold heavy soil loads. The most common builder is phosphate but, due to environmental concerns, phosphate is not used as much in modern solvents.

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Critical Micelle Concentration

CMC

Minimum concentration at which surfactants molecules begin to form micelles Determined by surface tension measurements
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< Below CMC = Surfactant adsorbs

Important Property
SmallMicelle

Micelle

Extremel y Dil. Soln 8/19/12

Dil. Soln

Soln at CMC

Soln above CMC

As surface concentration of ionic surfactant increases, if attractive hydrophobic interactions between alkyl chains can compensate for ionic head group repulsion, hemimicelles can form.

Specific Interactions: Chain-Chain

At low coverages, patches can form on the surface.

_ _ _ _ _ _ 8/19/12

_
+

+ + ++ +

Surfactant Behavior

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Solid Fat Index (SFI) & Solid Fat Content (SFC)

Solid Fat Index (SFI)

Ratio of solid fat to total fat Based on dilatometry

(change in volume liquid fat has a greater volume than solid fat)

Common among US suppliers. They converts SFI to SFC based on empirical equation
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Hydrophillic-Lipophillic Balance (HLB)

Invented by Willam Graffin (55 yrs ago) Ratio of oil loving portion to water loving portion Made for easier use of nonionics (end use appln.) Intended as a large scale use of emulsion performance concept for choosing emulsifiers
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Ranges = 1-20

HLB Hydrophilic Lipophilic Balance

HLB is a means of expressing the hydrophilic property of surfactants in figures

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HLB determination

HLB

= [M.W. hydrophilic portion / M.W. of lopophilic portion]/ 5

Example

: 20 mole ethoxylate of oleyl alcohol

M.W. 20 moles of ethylene oxide ( one mole ETO =44 )= 20 x 44 = 880 M.W. (oleyl alcohol)= 270 880+ 270 = 1150 ( M.W. of whole compound) What percentage of 1150 is 880 ? 880/1150 = 76.5% 76.5% divided by 5 = 15.3 15.3 is the HLB value of (20 mole ethoxylate of oleyl alcohol)

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HLB According to Griffin

(only for polyhydric alcohol types)

HLB = 20 ( 1 SV / AV )
Where S V = Sap value of ester of polyhydric alcohol AV = Acid value of fatty acid used Calculation of HLB value of PEG-7-glyceryl-cocoate AV of cocofatty acid = 265 mg KOH/g SV of PEG-7-glyceryl-cocoate = 95
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HLB Value
Significance
HLB Value 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18

Water in oil emulsifier

Oil in water Emulsifiers

Use Wetting Agents Detergents

Solubilizer

HLB and Use of Surfactants

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Solubility HLB Range Antifoam 1-3.5 (Reverse micelle) W/O emulsifiers 3.5-8 Wetting & spreading agents powder (in oils) 7-9 O/W emulsifiers 8-16 Detergent solution 13-15 Solubilizers 15-40

properties
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Solubilization

Spontaneous transfer of a compound insoluble in the bulk solvent into solution due to incorporation into the surfactant micelles

Normal micelles non-polar compound

Reverse micelles

polar compound

amphiphilic compound 8/19/12

Correct solubility for unique application

High Low

- for detergents - spreading & dispersion - invert emulsion

Medium

ExamplesSoaps - Medium to high in water Low in oils/fats. Anionics (SLS) - Very High in

1.

2.

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Wetting effect
Paraffin or new cotton cloth barely wetted by water But When surfactant is added to water their surface easily becomes wet

Surfactant in floor cleaner as a wetting 8/19/12agent

Wetting

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Contact Angle and Wetting

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5959

Emulsifiers

Role Types

:Form emulsions, Stabilize emulsions, Modify structures : Water In Oil - Low Hlb Oil In Water - High Hlb :

Examples
1.

Mono & diglycerides: HLB = 1 to 10 (Highly lipophilic) : produced by transesterification of glycerol and triacylcerides Polysorbates: Polyoxyenthyene esters of sorbitan monoesters Lecithin: A mixture of phospholipids including phosphatidyl cholines, phosphatidyl ethanolamines, inositol phosphatides, etc

2.

3.

Example 1. Glycerol Monostearate : HLB value of 3.6~4.2 Dissolves in hot grease, paraffine, ethanol, chloroform, acetone and 8/19/12 aether, the material is widely used when producing of chocolate, margarine, ice cream, skin care balsam, cold cream, hair oil and drug

Emulsions

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Emulsification

Examples of Emulsions

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Foaming effect
Foam consist of gas covered with thin liquid film. Surfactant molecule absorbed to interface between gas and liquid

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Substantivity

Adsorptive property of Cationics & related nitrogen compounds Adsorption, particularly into solid surfaces Attraction between +ve charge on nitrogen atom & -ve charge surfaces

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cloud point & pour point

The Cloud point of a fluid is the temperature at which dissolved solids are no longer completely soluble, precipitating as a second phase giving the fluid a cloudy appearance. The highest temp at which a nonionic surfactant solution is clear.
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The pour point of a liquid is the

What causes cloud points?

The solution becomes cloudy at & above the CPt temperature as the solution splits in to two phases

Phase1 : Very dilute surfactant solution Phase2 : Surfactant-rich micellar phase

The cloudiness you see comes from the micelles growing large enough to scatter light Cloud points are reversible, and upon 8/19/12

cloud point & pour point

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Fabric softener
(also called Fabric Conditioner) *is used to prevent static cling and makes the fabric softer.

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An emulsifier
*(also known as an emulgent or surfactant) is a substance which stabilizes an emulsion.

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An adhesive
*is a compound that adheres or bonds two items together.

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An ink
*is a liquid containing various pigments and/or dyes used for colouring a surface to render an image or text. Ink is used for drawing or writing with a pen or brush.

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A laxative
*is a preparation used for encouraging defecation, or the expulsion of feces. Laxatives are most often taken to treat constipation.

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detergents
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Detergent
*is a compound, or a mixture of compounds, intended to assist cleaning. The term is often used to differentiate between soap and other chemical surfactants used for cleaning purposes.

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Soil Removal Mechanisms

Deterge ncy (surface

chemistry)

Mechanic al
Roll-up Reduction in Soil Adhesion Liquefaction / Solubilization

Chemical

Liquid Soil

Solid Soil

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7575

Mechanism for Stain Removal

Liquid soil (Roll-up) Solid soil (Emulsification)

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7676

Anionic Surfactants
Linear Alkyl benzene sulfonate (LAS)

Main Strengths

S O

O-

Inexpensive (unless oil is expensive) Very effective at particulate soil removal Ca2+ sensitive (although not like soap)
7777

Weaknesses

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Anionic Surfactants
Soap Advantages

O C O-

Non-petroleum derived Oil particulate soil removal Very Ca2+ sensitive Need to separate low and high molecular weight acids and hydrogenate for odor control
7878

Weakness

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Composition of Coconut Oil Fatty Acid

Fatty Acid Caproic acid Caprylic acid Capric acid Lauric acid Myristic acid Palmitic acid Palmitoleic acid Stearic acid Oleic acid Linoleic acid Linolenic acid Composition C 6:0 C 8:0 C 10:0 C 12:0 C 14:0 C 16:0 C 16.1 C 18:0 C 18:1 C 18:2 C 18:3 % ND - 0.7 4.6 - 10.0 5.0 - 8.0 45.1- 53.2 16.8 - 21 7.5 - 10.2 ND 2.0 - 4.0 5.0 - 10.0 1.0 - 2.5 ND - 0.2 7979

Anionic Surfactants

Alcohol ether sulfate Strengths

O S O O - Na+

C12 -C15 O CH2CH2O - CH2CH2O - CH2CH2O

Alcohol ethoxy sulfate

Milder to the skin than alkyl benzene sulfonate Less effected by water hardness than other anionic surfactants High foaming Both the hydrophile and hydrophobe can be modified to give a range of chemical and physical properties Improved proteinaceous soil removal
8080 More expensive of than alkyl benzene sulfonate.

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Weaknesses

Nonionic Surfactants
Alcohol Ethoxylate

Strengths

RO

CH2CH2O n H

R= C11 - C16 Alkyl and n = 7 - 9

Ca2+ insensitive Decrease critical micelle concentration (CMC) Good for oil soil removal Very harsh towards hands (lipid extraction) Forms a gel phase on dilution with H2O and needs to be processed at T > 125 oF (52 oC) or utilize significant amounts of mechanical energy

Weakness

Higher levels of ethoxylation are solids and need to be melted and / or transported and stored hot n=7-9 C4 -C10 Alkyl O CH2CH2O n H Alkyl phenol ethoxylates are less expensive than linear ethoxylates but are possible endocrine disruptors. 8/19/12 8181

Commercial Routes for Production of Linear Alkylbenzenesulfonate

Blend of C10 to C14 olefins
+

Catalyst AlCl3 or HF

linear alkylbenzene

SO3

NaOH
O S O O - Na+ O S O OH

sodium linear alkylbenzene sulfonate

linear alkylbenzene sulfonic acid

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8282

Synthesis of Fatty Acids and Alcohols from Plants & Animals O

R R R C O C O C O CH2 O O CH CH2 O

H2O

CH2OH OH

OH

CH2OH

Triglyceride transesterification CH3OH

Fatty Acid hydrogenation H2

Glycerine

O R C OCH 3

hydrogenation H2

CH2OH

Methyl ester + Glycerine 8/19/12

8383

Synthesis of Alcohol Ethoxylate & Alcohol Ether Sulfate

O R OH

H2C

CH2

catalyst

RO

CH2CH2O n H

alcohol

ethylene oxide

alcohol ethoxylate SO3

RO

CH2CH2O n SO3- Na +

NaOH

RO

CH2CH2O n SO3H

alcohol ether sulfate

alkyl ether sulfuric acid

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8484

Laundry Detergent Formulations Raw Materials Percentage

Surfactants Wt. ratio of anion : nonionic Buffer Chelating Agent Polymers Enzymes Optical Brightener Fragrance Water (or Powder Filler) 10 30 % ~ 2:1 13% 05% 0 1% 01% 0 0.20 % 0 0.50 % 90 50 %
8585

Detergent Evaluations

Evaluations normally done in washing machines or on tergotometers.

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8686

Evaluation

Need to acquire or make stains

Laborious and time consuming process Reproducibility is major concern

For consumer stained garments, need to match stain intensity. Laboratory made stains, need to weigh and apply stain reproducibly.

For example, to evaluate 4 products on 10 stain sets requires: (4 clothes/stain)*10 stains*4 products * 2 repeats = 320 stain clothes

Evaluation either by instrumental reading or panelists

Reflectance Colorimeter shades of color calibrated with black (0) and white (100).

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Reflectance

8787

Challenges Facing the Detergent Industry

Increasing cost of raw materials Cost of transportation Changing demographics

Manufacturing sector of the economy in decline means that few consumers get clothes really dirty Nintendo effect leads to less youth participation in organized sports

Wal-Mart effect Wall Street effect

Emphasis of reduction in capital expenditures

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Structure of a Personal Care Corporation

CE O CFO Marketi ng
Advertisin g Focus Groups

Financ e Purchasi ng Manufacturi ng

Supplier Chain

R&D Customers Retailers Wal-Mart Drug / Food Stores Consum ers

Raw Material Suppliers

8989

Detergents ingredients
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Buffers
Importance of buffers

Maintaining an alkalinity reserve

Ease of obtaining the target pH during Common Detergent Buffers pKa manufacturing Sodium Citrate pKa3 = 6.3

Phosphates Borate (Borax, Na2B4O710H2O) Sodium Carbonate (Soda Ash) Sodium Silicate (Sand + NaOH)

pKa2 = 7.2 pKa3 =12.67 pKa = 9.24 pKa2 = 10.33 pKa ~ 10 -11.2
9191

Chelating Agents
Chelating agents complex Ca2+ and Mg2+ which allows for better surfactant efficiency.
Detergent Chelating Agents EDTA Phosphates Zeolites Sodium Carbonate Polymers of polycarboxylic acids Sodium Citrate Comments Impacts bioavailability of Ca2+. Not normally used in laundry applications. Eutrophication Solid particles, Increases septic tank burden Precipitation of CaCO3 (used in powders) Very Expensive Most commonly used in liquid laundry detergents.
9292

Enzymes
Biological macromolecules which have a high affinity for a select subset of stains

Advantages

Very efficient catalysts

Disadvantages

Difficult to stabilize (lifetime of a laundry detergent may last more than 6 months to 1 year

Sensitive to high pH (pH > 9) Some surfactants denature proteins 9393

Very expensive

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Classes of Enzymes

Protease

Protein sensitive stains include: milk (casein), grass, meats, blood Most widely used enzyme Proteases will destroy other enzymes (enzymes are proteins) Degrade starch based foods Reduces pilling by cleaving cellulose linkages Breaks down triglycerides (natural oils)

Amylase

Cellulase

Lipase

8/19/12 9494 Works slowly and most effectively after the wash cycle is

Anti-Redeposition
Keep suspended soils from redepositing on garments.

Modified cellulosics

Sacrificial layer provides a multi-wash benefit.

Cellulose deposits on cotton. Soil/stain deposits on cellulose. Cellulose (with soil) removed by detergent.

Benefit is only for cotton

Combination of anionic polymer (polyacrylate) with partially cationic polymer (polyvinylpyrolidone, PVP). PV Mechanism is likely entrapment of particulates. P PVP methacrylate at reducing Laurylalso effective Acrylic acid dye transfer 8/19/12 9595 copolymer, z/y > 10

Bleach

Normally added to laundry process as a separate product.

Tide with Bleach powder is exception

O

Most common bleaches H are chlorine bleach R C O O (OCl and peroxides)Acid Peroxy

Difficult or expensive to stabilize the bleach or other raw materials (from bleach) in the formulation. Reacts with conjugated carbon double bonds to decolorize chromophores.
-Carotene

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9696

Optical Brighteners

Fluorescent Whitening Agents Generate a bluish hue that most people associate with a more satisfying white. Worldwide consumers recognize about 2500 different shade of white. Increases the brightness by converting UV light into visible light. Emitted blue light hides yellow and brown tones making treated textiles (or paper appear whiter). Generate a strong purple color when exposed to UV light.
9797

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How Do Optical Brighteners Work?

H H N N N N
+

H C N N SO3 Na
+

H N Na - O3S C

N N

H N

H N

N H

Optical Brightner

Highly strained system (steric hindrance) Can control wavelength of light emission by changing steric and/or electron donating characteristics Can alter solubility and deposition by changing the substituents (more 8/19/12 9898 hydrophobic or hydrophilic)

Fragrances

Important factor in consumer acceptance or rejection of product. Top notes: Fragrance out of bottle. Middle notes: Fragrance while doing laundry (smell on wet clothes). Bottom notes: Fragrance on dry garments (need to with stand heat of dryer). Target: Elusive fresh and clean smell.
9999 Different cultures have different

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Surfactant applications
Oral Skin Sodium Lauryl Sulfate Ammonium Lauryl Sulfate Sodium Lauryl Ether Sulfate Ammonium Lauryl Ether Sulfate Alcohol ethoxylates Sulfosuccinate Ethanolamides Amine oxide Hair Soap Bath Sun Disinfectant/Bl protection eaching

Surfactant applications
Oral Skin Hair Soap Bath Disinfectant/ Bleaching

Benzalkonium chloride

CAPB CAPB - DC PEG -7 Glyceryl Cocoate

Surfactant based Soap noodles & flakes

FORMULATIONS
INGREDIENTS Click to edit Master subtitle style

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Soap
Lye tends to produce a better and lyefor soap making (also known as harder bar of soap whereas potash sodium hydroxide) produces a not so nice softer bar of usepotash(potassium hydroxide) soap skin conditioners: hydrogenated bars of soap: coconut oil, palm oil, tallow acid (skin conditioner), tallow (rendered beef fat), or lard coconut acid, soap (sodium (rendered pork fat), tallowate, sodium cocoate, and/or softer soaps: olive oil, soybean oil, sodium palm kernelate) or canola oil glycerin (emollient and texture enhancer) Detergents may also be added to Sorbitolis another emollient used soap to help increase the cleaning along with glycerine. power of the product. nutrients : Aloe Vera Balsam copaiba preservatives :Because soap is Honey made from oils and fats, Oatmeal - this is a great ingredient 8/19/12 preservatives are often included to for all natural soap

Liquid Soap
The buffer agents in liquid detergent help to resist pH changes caused by the other ingredients in the liquid. A stabilizer in the detergent is added in order to keep the various ingredients in detergent in a constant liquid state and avoid their separation when you store it for long periods of time. Cleaning agents in liquid detergent are called surfactants, or surface active agents. 8/19/12

DTERGENT (POWDER)

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FACE WASH

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FACIAL CREAMS

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HAIR OIL

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SHAMPOO

HAIR GEL

TOOTHPASTE
Active Ingredients: Abrasives-50%: f Fluoride aluminum hydroxide(Al(OH)3), Antibacterial agents, most often calcium carbonate (CaCO3), Triclosan is used to control plaque various Desensitizing agents calcium hydrogen phosphates, Anti-tartar agents varioussilicasandzeolites, Sodium bicarbonate (baking soda) andhydroxyapatite Enzymes, to enhance the (Ca5(PO4)3OH). antibacterial properties of saliva Xylitol, a non-sugar sweetener, Fluoride: Sodium fluoride(NaF) which reduces levels of cariogenic is the most common source of (decay causing) bacteria in the fluoride, butstannous fluoride mouth and enhances (SnF2),olaflur(an organic salt remineralization of fluoride), andsodium monofluorophosphate(Na2PO3F) (Natural toothpastes may contain

SHAVING CREAM
Functions Pleasing foam Easy rinsing Minimalskin/eyeirritation Feels thick and/or creamy Pleasant fragrance Lowtoxicity Goodbiodegradability Slightlyacidic(pHless than 7) No damage to hai Ammonium chloride Ammonium lauryl sulfate Glycol Sodium laureth sulfate Sodium lauryl sulfate Sodium Lauroamphoacetate Polysorbate20 (PEG 20) Polysorbate80 Citric Acid Quaternium-15 Polyquaternium-10 Di-PPG-2 myreth-10 adipate Methylisothiazolinone tetrasodium EDTA