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Made by alkylation of tertiary amines
+
charge(s) and counter-anion(s) with negative charge(s)
--------
Antimicrobial Quats:
Disruption of intermolecular interactions (bacteriostatic, fungistatic, algistatic,
antiviral activity)
Corrosion Inhibitors:
Substantivity of the cationics will create protective coatings
Ore Flotation:
Quats will form monomolecular films on negative particles. Air bubbles will
float the hydrophobic components
Asphalt Emulsions:
Cationic emulsions will coat inorganic particles and metal surfaces even in
wet conditions (highway construction, vehicle undercoating)
Miscellaneous Applications:
Cosmetics, Hair conditioners, Pigment dispersants, etc.
Consumer Specialties | Business Line Household Care Page | 5
Fabric Softening
1. Overview
2. Rinse Cycle Products
3. Dryer Cycle Products
+
from: J.N. Israelachvilli et al., J. Chem. Soc.,
Faraday Trans. II, 72 (1976) 1525-1568
Homogenize
- -
“heat” quat to T °C
T °C
Disperse quat
into water at T °C; mix
t °C
3. Cooled down while being mixed
homogenized
- -
at T °C
• Industrial process
Doctor Blade
Cutting Blade
Squeeze
Roll
ADOGEN® 471
R O R'
80 10
60
1
40
0.1
20
0 0.01
Dialkyl-dimethyl Ester Dialkyl-dimethyl Ester
OECD 301 E (5 d) OECD 301 C (30 d) OECD 201 (Algae) OECD 202 (Daphnia) OECD 203 (Fish)
Ester quaternaries yielded significantly better data than the standard dialkyl-
dimethyl quaternaries
Consumer Specialties | Business Line Household Care Page | 24
Fabric Softener Actives
1. Chemistry, Biodegradability
2. Chemistry, Performance
3. Physical State
4. Improvement: Room Temperature Dispersible Quat
Imidazolinium
VARISOFT® 475 75% Paste, tallow
Softening
Fragrance Impact
Static Control
Range of Formulation
Biodegradation
Consumer Specialties | Business Line Household Care **** = most favorable Page | 30
Fabric Softener Actives
1. Chemistry, Biodegradability
2. Chemistry, Performance
3. Physical State
4. Improvement: Room Temperature Dispersible Quat
CH 3 OSO3
R O O R
Ester Quat N
O OH O
CH3OSO3
H H
Amidoamine R N
N
N R
O ((CH2)2O)nH O
O
Imidazolinium N N CH3OSO3
R N
H
R
Nitrile R N R Cl
CH 3 OSO3
TEA Ester Quats
R O O R
Ester Quat N Biodegradable
O OH O
Globally accepted
Regional CAS numbers
CH3OSO3
H H Descriptor matches fatty acid
Amidoamine R N
N
N R
Nitrile R N R Cl
361,000 (2014)
+2.5% -0.1%
+5.7%
+3.8%
+6.0%*
45 °C (113 °F)
Pumping Temperature 25 °C (77 °F) minimum 55 °C (131 °F) minimum
minimum
Homogenize
- -
“heat” quat to T °C
T °C
Disperse quat
into water at T °C; mix
t °C
3. Cooled down while mixed
Preservative
20 40 60 80 100 Time
(min)
Preservative
20 40 60 80 100 Time
(min)
100
Statistics
60 Fabric samples prepared according
to ASTM Method D 5237
40 Statistical differences reported at
Softer
95% confidence level (Friedman
20
Simple Rank)
Brand A is based on TEA Ester
0 Quat technology
Control EVONIK Brand A
1.5
Force
0
1
5
9
13
17
21
25
29
33
37
41
45
49
53
57
61
65
69
73
77
81
85
89
93
97
101
105
Displacement
Consumer Specialties | Business Line Household Care Page | 50
Fabric Softener Dispersion
Softening Performance – PHABROMETER®
110
Fabric samples prepared
according to ASTM Method D
100
5237
Average of five replicates per
Softer
90
sample
80 Statistical differences reported at
95% confidence level
70
Brand A is based on TEA Ester
Control Brand A EVONIK
Quat technology
REWOQUAT® WE 45 offers
Potential cost savings for
Storage and handling
Processing
Energy use & cycle time
Formulation flexibility and performance
Ability to produce both non-concentrated and ultra formulas
Stable formulations from 5% to 20%
Softening and anti-stat equal to other ester quats
Patent pending technology
Storage
Actives Anti-
Active Type Dryer Cycle Product Biodegradability1 Temperature
(%) Static
(° F)
Readily
VARISOFT® DS 355 65 **** 155-165
(OECD 301)
TEA Ester
Quats
Readily
VARISOFT® DS 362 65 **** 160-170
(OECD 301)
Dialkyldimethyl
Humidity Chamber
4.00
3.50
3.00
Static Decay Time (s)
2.50
2.00
1.50
1.00
0.50
0.00
National Brand VARISOFT® DS 355 VARISOFT® DS 362
(C2H5O)xH N+ (C2H5O)yH
R’
Actives
Product x+y R R’ Counter Ion
(%)
Variquat
100 15 CH3 Coco Methyl Chloride
K 1215
Rewoquat
100 5 CH3 Coco Methyl Sulfate
CPEM
Variquat
100 2 CH3 Coco Methyl Chloride
638
Consumer Specialties | Business Line Household Care Page | 58
Antistatic Spray Performance:
Ethoxylated Quats Work Well
0.25
50.00
0.20
0.10
30.00
0.05
20.00
0.00
Static Guard Varisoft 137 90 Varisoft 222 LM WE 45 Rewoquat Adogen 66
90 CPEM
10.00
0.00
Static Guard Varisoft 137 90 Varisoft 222 LM WE 45 Rewoquat Adogen 66
90 CPEM
Consumer Specialties | Business Line Household Care Page | 59
Ethoxylated Quats
1. Antistatic Sprays
2. Cleaner blends
Drying
Rinsing
-
Cleaning
1. Mechanical energy
Most carwashes do not use brushes anymore to protect the car
finish
“Touchless” systems are getting more popular
2. Time
Longer reaction time: better cleaning, but higher chance of
damaging the car finish
Longer time → less capacity → time is money
-
3. Temperature
Higher temperature: better cleaning, but higher chance of
damaging the car finish, higher energy cost
4. Chemistry
Most important factor
Should be highly efficient, safe, economical
Environmental friendly: minimum waste (water/chemical)
Water
Oil
Paint
Composition
Specialty blend of cationic and nonionic surfactants
Performance
Excellent degreasing and soap scum removal
Good emulsification, anti-redeposition
Provides antistatic property
Easy rinsing, quick drying
Imparts gloss
Ease of Formulation
Good surfactant compatibility (even with anionics)
100% active liquid, easy to process
No solvent or hydrotrope needed
Moderate foaming
High/low pH, temp., hard/soft water
Consumer Specialties | Business Line Household Care Page | 64
REWOQUAT® CQ 100 G
Hard Surface Cleaning Results
National Brand CQ 100 G based National Brand CQ 100 G based National Brand CQ 100 G based
All Purpose All Purpose Tub & Tile Cleaner Tub & Tile Traffic Film Traffic Film
Cleaner Cleaner 3.5 % active Cleaner Remover Remover
10.9 % active 2.0 % active 1.0 % active 10.9 % active 2.0 % active
Water
- - - - - - - -
Paint
Major Challenges
-
Step 1. Step 2. Step 3.
Cleaning Rinsing Drying -
(Anionic) (Water) Softening
A
Cationic emulsifier Anionic surfactant Inactive, insoluble
B
Scavenger (monoquat) Anionic Inactive, soluble
surfactant
Recommendations:
• Use level:
Depending on rinse efficiency
Use at least the same amount as the anionic carry-over concentration
• Chemistry:
Monoalkyl diquats are the most efficient
CH3 2CH3OSO3
Cl Cl (CH2 -CH2-O)xH
R CH3 CH3
N CH3 Cl R N (CH2-CH2-O)yH
R N
N N CH3 CH3 (CH2-CH2-O)zH
CH3 CH3
CH3 CH3
R = tallow, x, y, z > 1
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Customers associate semi-wet cars with poor
cleaning: they can easily be resoiled, water droplets
leave spots after drying
Water
- - - - - - - -
Paint
rinse aid
water film
surface
1. Water film adheres to
2. Sprayed -on rinse aid
the surface upon
penetrates through water film
washing and rinsing
and spreads over the surface
Water
++ + ++ +
+ + + +
+ +
++ + + ++ +
+
- - - - - - - -
Paint
water film
rinse aid hydrophobic film
water film
surface
Water
++ +
+ +
+
++ + +
+ + + +++
- - - - - - - -
Paint
water film
rinse aid hydrophobic film
water film
surface
Water
Water beads up, smaller
droplets combine to bigger ones
(Beading) and removed by + + + +- + + + + + + + +
- - - - - - -
a blower Paint
A2
A1
θ1 θ2
B1 B2
the face area increases: A2>A1
higher droplet profile (“larger sail”), easier water removal by the blower or driving
wind
the footprint decreases: B2<B1
less contact between the droplet and the surface: less sticking, easier
water removal by the blower or driving wind
Consumer Specialties | Business Line Household Care Page | 79
Drying, Protection
1. Theory and Practice
2. Organomodified Silicones
3. Traditional and Biodegradable Systems
Siliconophilic
Silicone Oil
Polyether-
Alkylsiloxanes
siloxanes
Alkylpolyether-
siloxanes
Ionic Siloxanes
Hydrophilic Lipophilic
Consumer Specialties | Business Line Household Care Page | 81
Basics of Silicone Quats
+ /
+ +
Consumer Specialties | Business Line Household Care Page | 82
Silicone Quats
Strong Bond Between Surface and Molecule
Surface
Silicone Backbone
Surface
Silicone Backbone
Surface
What a difference!!! ☺
HISTORICAL EVOLVING
Goal:
Develop an emulsifier that enables the formulation of rinse aids/drying
agents to address the needs of the evolving market
Biodegradability
Environmental friendliness (low aquatic toxicity)
Formulation versatility (for both traditional and biodegradable ingredients)
Water reclaim system friendly formulations (due to droughts)
Performance: improved drying/protection for less spotting
Safety: low toxicity
Raw materials from renewable resources
Price/performance advantages
Ester Quats:
X
CH3
TEA type:
R O O R
medium performance, limited formulas N
good biodegradability, low toxicity O OH O
(1:2:1 mixture of mono-, di- and tri-fatty-alkyl ratio) (+ monoquat and triquat)
(R = Fatty Alkyl)
MDEA type: X
-
good performance, versatile formulas CH3
good biodegradability, low toxicity R O O R
N
(enhanced di-fatty-alkyl content) O CH3 O
(+ monoquat)
Consumer Specialties | Business Line Household Care
(R = Fatty Alkyl) Page | 91
Traditional and New Hydrophobes
Ester Oils:
Alkyl Laurate, Palmitate, Stearate, etc.
good performance, versatile formulas O
good biodegradability
R O R'
low toxicity
low odor
R = Fatty Alkyl
R'=straight or branched Alkyl >C5