The document discusses the development and marketing of gellant technology. It describes how gellants were initially developed serendipitously in 1996 to improve polyamide stability. The technology was then applied to candles without proper market analysis, leading to early struggles. The document outlines how gellants work and their various applications, such as in personal care products, air fresheners, and fuel additives. It also presents sales data showing the growing success of gellant applications in candles and personal care.
1. Applying Marketing Principles
to Bring Technology to
Commercial Reality
CDMA Fall 2005 Meeting
Philadelphia, PA
Gerald C. Marterer, Vice President
International Paper Co.
September 28, 2005
2. How It Started
• 1996 – “playing with molecules” in pure research
environment
• Intent was to improve stability of curing agent
polyamides
• Unexpected serendipitous results:
– Gellation of organics
– A “techno oddity”
– Became technology hobby shop
2
3. Introduction
Pine Trees
Tall Oil Fatty Acid
(TOFA)
Polymerized Fatty
Acid (Dimer)
3
Perhaps you’ve had the opportunity to work with polymerized tall oil fatty acid – commonly referred to as “dimer acid”- or
perhaps one of its esters or amides. It is a product of the pine chemical industry. To be fair, it is a product made as well from
all manner of vegetable oils. There is nothing in the world like dimer acid. First it contains 36 carbon atoms – the closest
material with similar reactivity to dimer is dodecanedioic acid with only 12 carbon atoms. Even in its purest form the atoms
of dimer are arranged in hundreds of combinations of branched chains many with five or six-menbered rings. This makes
the material inherently non-crystalline and therefore good for wetting surfaces and not becoming brittle at lower
temperatures. And it bears two carboxylic acid groups which may be turned into a variety of esters, alcohols, and amides. In
contrast, dodecanedioic acid is a strictly linear diacid, with high crystalline structure, good for making nylons.
4. Dimer Acid
Unique combination: large
hydrocarbon (C36), oil-loving
mass with two acid groups
Hundreds of isomers
Non-crystalline (clarity, good low temperature properties)
Derivatives via reactions at the acid groups
Esters, alcohols and amides
Which have good surface-wetting properties
adhesives, inks, lubricants.
4
Perhaps you’ve had the opportunity to work with polymerized tall oil fatty acid – commonly referred to as “dimer acid”- or
perhaps one of its esters or amides. It is a product of the pine chemical industry. To be fair, it is a product made as well from
all manner of vegetable oils. There is nothing in the world like dimer acid. First it contains 36 carbon atoms – the closest
material with similar reactivity to dimer is dodecanedioic acid with only 12 carbon atoms. Even in its purest form the atoms
of dimer are arranged in hundreds of combinations of branched chains many with five or six-menbered rings. This makes
the material inherently non-crystalline and therefore good for wetting surfaces and not becoming brittle at lower
temperatures. And it bears two carboxylic acid groups which may be turned into a variety of esters, alcohols, and amides. In
contrast, dodecanedioic acid is a strictly linear diacid, with high crystalline structure, good for making nylons.
5. Dimer-Based Polyamides
React dimer acid with a polyamine, remove water
Terminate the chain with a carboxylic acid
Thermoplastic, non-crystalline (clear, flexible) solids
Softening points from ca. 80–190oC
High molecular wt. PAs are hot melt adhesives
Low molecular wt. are for flexographic inks
High amine number are epoxy curing agents
5
Dimer acid-based polyamides are of special interest to my company and to me. We make them by reacting dimer acid and
a diamine such as ethylene diamine or a polyamine such as diethylenetriamine. They can be tough or brittle, have softening
points up to about 200 degrees C and are well-established hot-melt adhesives and electrical potting compounds, epoxy
curing agents, and components for solvent-based flexographic inks for printing on flexible films and foils from alcohol and
alcohol-toluene or alcohol-xylene blends. They are not soluble in water or most organic liquids, certainly not in mineral oils,
ketones, ethers and the like.
6. Dimer Polyamides–Standard vs. Gellant
Conventional dimer-based polyamides have limited solu-
bility in solvents; dissolve only in aromatic/alcohol blends
Used as thixotropic agents for alkyd paints in Europe
Recognized (1996) that termination of the polymer chain
with fatty alcohol gave materials cabable of gelling mineral
oils and fatty esters
Initial application was in clear candles (1999)
New polymers extend gelation to virtually all organic liquids
Applications emerging in home and personal care products.
6
7. How To Make A Gel
Heat the gellant (typically 5-20%
by wt. of the total formulation) to
its melt point (usually 80-100oC);
Add the liquid with agitation,
holding the temperature constant;
Cool to about 10-20oC below the
gellant melt point and
Pour the mixture into a container,
mold, package, etc.
See, e.g. Arizona, US #6,268,466
15% SylvaclearTMA200 in Finsolv®TN
7
8. How Gellants Work
Hydrogen
bonding
O
forms oil- O
N C C
repellant H
N R
H
zones
O O
N C C N R
H H
O Fatty dimer
C N R segments form
H
oil-loving zones
8
9. Gellant Classes
1. Ester Terminated Polyamide (ETPA)
2. Tertiary Amide-Terminated Polyamide (ATPA); dimer acid, a
diamine and a di-fatty amine.
3. Polyether-Terminated Polyamide (PAOPA); dimer acid, a
diamine and a polyether mono amine.
9
10. Gellant Test Data
Ester- and tertiary amide-terminated polyamides can gel
these relatively non-polar liquids:
Mineral spirits Mineral oil
Alcohols (>C8) Heat transfer fluids
Xylene Mono/di/triglycerides
Aliphatic acetates Soya methyl ester
Glycol dimethyl ethers Soybean oil
Plasticizer Esters Castor oil
10
You can see that the release or evaporation of the hexyl acetate looks very like the gelled hexyl acetate. Reader may need to return to previous
slide to talk about spiking and tailing.
11. Gellant Test Data
Polyether-terminated polyamides can gel these relatively
polar liquids:
Propylene carbonate Glycols
N-methyl pyrrolidone 2-Methoxyethyl ether
Aromatic esters Linear polyether polyols
Ethyl lactate Branched polyether polyols
DMSO Dipropylene glycol
Ketones Ethoxy ethyl propionate
11
You can see that the release or evaporation of the hexyl acetate looks very like the gelled hexyl acetate. Reader may need to return to previous
slide to talk about spiking and tailing.
12. “A Hammer in Search of a Nail”
• Sister company involved in fragrances
– Immobilized fragrances
– Clear candles
• Jumped into market with no market analysis or STP
• Initial results felt good
12
13. Gellants in Candles
Mineral Oil - Ester (fuel)
Polyamide (gellant),
Fragrance Oil;
Clarifiers (diol, fatty acid).
See: Bath & Body Works, US #6,214,063
13
23. “Ready, Fire, Aim”
• Samples sent to everyone
• Everyone was interested
• No experience in segments
• How to get burned!
• “Bunny Marketing”
23
24. “Call Time Out”
(2002)
• Market-based analysis
– Ready, aim, fire
– STP
24
25. Market-Based Strategic Planning
“READY” “AIM” “FIRE”
Implementation
Potential
competitor
Market trends responses Application/ People implications
annual plan • Building skills
+ • Building will
• Staffing changes
Characteristics
of customers’ Target
Industries segments Budget External initiatives
• Alliances
+ Attractiveness Value • Divestitures
of important proposition
customer options for
+
Competitive segments attractive Facilities & Tracking and
environment segments AZC value
proposition capital adjustment
for each implications approach
+ targeted
segment
AZC customer/ Customer Expected benefits:
product strategies • Better customer &
profitability and needs product mix
• Higher price levels
AZC
• Sales volume growth
capabilities
• Higher profits and ROI
25
26. “Call Time Out”
(2002)
• Market-based analysis
– Ready, aim, fire
– STP
• Analyze channels
• Determine need for partners
• Determine opportunities for licensing
26
27. Features/Advantages
Controllable gel strength (by concentration,
alcohol)
Light color (approaching “water white”)
High fragrance loading with excellent
compatibility, linear release
Provides gloss to skin care applications
Never act as thickeners - gels do not become
less elastic when diluted, just softer, jelly-like
27
28. Features/Advantages
Compatible with organic components and actives
in formulations, allowing high actives loadings
Release of actives is unimpeded
Transparency for many formulations
Easily processed into formulations with heat
(processing temperatures <100C) and shear; low
process viscosities are typical.
Provides uniform dispersion of pigments and other
solids in formulations
28
29. In Air Fresheners
Can load up to 50% fragrance in gels
Clear, firm, stable
Free-standing or container formats
Compatible with most fragrance oils
Unimpeded release of volatiles.
See: Jeyes, WO
#02/066084
29
30. Water-Friendly Gellants
”WF” gellants dissolve or disperse in water.
Gel blends of surfactant, fragrance, actives, carrier liquids.
Product is a firm, clear
solid that “rinses” away
in water.
Application to bath oil
beads, toilet bowl care
products.
See: Arizona US published
application #2004/0186263
30
31. In Personal Care Products
Cosmetics
• Lipstick
• Mascara
• Foundations
• Scenting oils
Creams, lotions
Antiperspirants
Sunscreens, insect
repellents
See: Arizona, US #6,875,245 and
Color Access, US #6,497,861
31
32. Potential Gellant Segments
Technology fit - does it Large volume Overall
Opportunity work? opportunity Likely margins Comments Attractiveness
•Currently pursuing in Europe,
US
•Largely European initiative
•Barriers to entry include long
product dev. time, testing
•Fuel Additives / •Currently in testing, potentially
Grease attractive
•Candles •Fad-driven, pursued but not
sustained
•Toner •Xerox-initiated interest
•Dust/Particle •Competes against commodity
Control materials
•Phase Change •In testing
•Industrial Cleaners •Competes against commodity
materials
•Paints & Coatings •Limited end-use technology fit
32
33. Gellants for Personal Care
(Sales)
4.00
3.00
Sales Revenue $MM
2.00
1.00
0
2001
Personal Care
33
34. Gellants for Personal Care
(Sales)
4.00
3.01
Sales Revenue $MM
2.01
1.02
0.02
2001 2002
Personal Care
34
35. Gellants for Personal Care
(Sales)
4.00
3.00
Sales Revenue $MM
2.00
1.00
0
2001 2002 2003
Personal Care
35
36. Gellants for Personal Care
(Sales)
4.00
3.00
Sales Revenue $MM
2.00
1.00
0
2001 2002 2003 2004
Personal Care
36
37. Gellants for Personal Care
(Sales)
4.00
3.00
Sales Revenue $MM
2.00
1.00
0
2001 2002 2003 2004 2005F
Personal Care
37
38. Lessons Learned
• Understand patent landscape early on
• Protect composition patents from downstream
applications filings
38
39. Arizona Portfolio Covers Several Key
Gellant Application Areas
Gellant Cable Gel-Based
Filler Candles
Personal Gellant
Care Products Composition
of Matter
Polyamide
Cosmetic
Electrolyte Gels
Products
Assignee Labels
261 Arizona
Patents & Apps.
39
40. Lessons Learned
• Understand patent landscape early on
• Protect composition patents from downstream
applications filings
• Before going to market:
– Use “ready, aim, fire”
– Complete STP
• Beware of short life cycles
• Be ready to partner or license
• “Guns, Germs and Steel”
40