PRIPOL dimerised fatty acids

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PRIPOL dimerised fatty acids

• Large hydrocarbon part (C36)
• hydrophobic
• hydrolytic resistance of derivatives
• affinity for non-polar matrices and surfaces

• Irregular non-crystalline structure
• flexibility
• low Tg
• flow, wetting

• Di-functional constituent for
• polyamides
• polyesters
• polyurethanes

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Different forms of PRIPOL dimer technology
PRIPOL dimer acid PRIPOL dimer
diol PRIPLAST polyesters made with PRIPOL dimer
acid or dimer diol
HO----
----- OH
E-E
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A unique performance effect

• PRIPOL and PRIPLAST technology provide
• a unique combination of resistance against
• Moisture
• Chemicals
• Heat
• Oxidation
• Radiation

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Supportive data
Polyurethane samples were prepared from a range
of Priplast polyols and competitive
technologies (hexane diol adipate,
polycaprolacton, hexane diol carbonate, PTMEG,
PPG, and polybutadiene diol) All polyols used
had molecular weight of 2000, except Priplast
3196, which is 3000 All recipes were identical
in molecular ratio one part polyol, 2 parts of
butane diol, 3.1 parts of pure MDI All
polyurethanes were made via the prepolymer route
first a prepolymer of polyol and MDI, followed by
chain extension with butane diol
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Moisture uptake of PRIPLAST dimerate and other
polyurethanes
Moisture uptake at 23 C,
Recipe 1 Polyol 2 Butanediol 3.1
MDI Conditions 1 week in H2O dist.
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Hydrolysis of PU from PRIPLAST dimerate and other
polyols
Retention of tensile strength,
Recipe 1 Polyol 2 Butanediol 3.1
MDI Conditions 1 week in H2O (dist.) at 90
C
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Effect of UV-radiation on PU from PRIPLAST
dimerate and other polyols
Retention of tensile strength,
Recipe 1 Polyol 2 Butanediol 3.1
MDI Conditions 2 weeks exposure to UV-B
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Effect of oxidation on PU from PRIPLAST dimerate
and other polyols
Retention of tensile strength / elongation,
Recipe 1 Polyol 2 Butanediol 3.1
MDI Conditions Exposure to 140 C for 4
weeks
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PRIPLAST versus other diols stability of TPU
Retention of tensile strength,
Recipe 1 Polyol 2 Butanediol 3.1
MDI Exposure for 2 weeks
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Weather resistance
Retention of tensile strength,
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Hydrolytic stability of PU in boiling water
Retention of tensile strength,
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Mechanical properties of PU from PRIPLAST
dimerate and other polyols
crystalline adipate
Recipe 1 polyol 2 BDO 3.1 MDI
PTMEG
strain hardening
Priplast 3192 HDO dimerate/adipate
Stress
Priplast 1838 HDO dimerate
no strain hardening
Poly BD/rubber
Strain
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Effect of polyol on modulus and tensile strength
Recipe 1 Polyol 2 BDO 3.1 MDI
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Elongation of PU made with PRIPLAST dimerate and
other polyols
Elongation at break,
Recipe 1 Polyol 2 BDO 3.1 MDI
differences only for different MW (3196 is mw
3000, all others 2000) and functuionality
(poly-BD)
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Shore-A hardness of PU made with PRIPLAST
dimerate and other polyols
Shore A
Recipe 1 Polyol 2 BDO 3.1 MDI
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T(g) of PU made with PRIPLAST dimerate and other
polyols
Glasstransition temp., C
Recipe 1 Polyol 2 BDO 3.1 MDI P1838 ()
1-1-2.1
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PRIPLAST polyols for elastomers
A unique combination of thermo-oxidative and
hydrolysis resistance Low-temperature
flexibility and flex fatigue resistance Low-modul
us and soft-touch applications
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Elastomers by one-shot processing of PRIPLAST
polyols
- Priplast polyols do not mix well with many
other polyols (especially adipates), chain
extenders and isocyanates - one-shot processing
without precautions may cause difficulty very
brittle product, or very sticky product - good
one-shot processing is possible by making a blend
of PRIPLAST polyol and chain extender (like
butane diol), and convert this blend in a
one-shot process - if for some reason (cost,
performance) it is considered to blend PRIPLAST
polyol with other polyester polyols, we
recommend to NOT make a physical blend, but
instead work with one single PRIPLAST polyol made
with a mixture of acids
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Blending polyols
- very careful when mixing partially crystalline
polyols disturbance of crystallinity kills
hydrolytic stability, green strength and
tensile strength. Acceptable combinations 3192
with hexane diol adipate, 3195 with butane diol
adipate - only recommended for the propolymers,
for reasons of limited compatibility
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PRIPLAST polyols for coatings
- for exceptional weatherability and protection
(anticorrosive applications) - for exceptional
flexibility, flex fatigue resistance - for
adhesion to low-energy substrates like
plastics - for 2K, moisture cure and aqueous
dispersion type
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PRIPLAST technology for polyurethane coatings
benefits
hydrocarbon character, strength (preservation of
hydrogen bonds) hydrophobicity durability
(hydrolytic resistance) substrate protection
(moisture barrier) adhesion to low energy
substrates non-crystallinity, strength (flow,
substrate wetting) low glass transition long open
time durability (low-temperature
flexibility, stress absorption)
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PRIPLAST technology for PU coatings conditions
No NMP or other cosolvents solids content at
least 35 particle size max. 500 nm aliphatic
diisocyanates for colour stability reasons
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PRIPLAST technology in aqueous polyurethane
dispersions
recipe 44g Priplast 3195, 6.0g DMPA at 130C/10
mbar for 30 minutes break vacuum with N2, cool to
110C, add 38.9g IPDI in 10 minutes, react for 1
hour cool to 60C and add 35g acetone, stir until
a clear solution is obtained cool to 50C, add 6g
BDO and 25g acetone slowly, then another 10g of
acetone react to NCO-number 1.8 (20 hours without
catalyst, about 8 hours with catalyst) add 140g
acetone add mix of 3.1g IPDA0.3g NH4OH (25)20g
water, react for 5 hours add 1.8g NH4OH (25),
stir for half an hour add 100g water while
intensively stirring, until phase inversion
(CRITICAL step) add 50g of water, then remove
acetone at 50C under gradually increased vacuum
(down to 450 mbar, to prevent foaming) to
increase crosslinking use 5.5g BDO with 0.5g
TMP
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Formulations
Priplast 3195 (2000 MW) Priplast 3195, with TMP
crosslinker hexane diol/neopentylglycol (1/1
molar basis) adipate, 1700 MW (Fomrez ER
191) hexane diol/neopentylglycol (1/1 molar
basis) adipate/dimerate (1/1 weight basis), 1700
MW Reference Commercially available benchmark
(aliphatic polyester polyol, 4 NMP, 40 solids,
sold at about Euro 7/kg dispersion)
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PRIPLAST technology in aqueous polyurethane
dispersions
- resulting white dispersions have 40 solids and
100-200 nm particles, and give clear
transparent film - film blocking of
Priplast-based materials exceeds that of
commercial PU dispersions - freeze thaw
stability gt1 month at -5/40C
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Properties of coatingsbased on PRIPLAST and
other polyols
Polyol water uptake adhesion cross cut
24h/23 24h/50 alufoil steel acryl PVC ABS PR
IPLAST 3195 2 8 0 0 0 0 0 slight haze PRIPLAST
3195/TMP 3 7 0 0 0 0 0 slight haze HDO/NPG
adipate 9 14 0 0 5 0 0 white HDO/NPG
3 8 0 0 5 0 0 adipate/dimerate slight
haze Commercial PUD 8 15 4 0 0 1 1 whit
e
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Chemical resistance of coatingsbased on PRIPLAST
and other polyols
Polyol ethanol butter desin- coffee water ethyl
aceton (50) fectant acetate 1 h 24h 10
min 24h 16 h 10 sec 10 sec PRIPLAST
3195 1 0 1 0 0 5 5 PRIPLAST 3195/TMP 3 0 1 0 0 4
5 HDO/NPG adipate 0-1 0 1 0 0 5 5 HDO/NPG/AA/C
36 0-1 0 1 0 0 5 5 Commercial
PUD 5 1 5 2 5 4 4
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Properties of coatingsbased on PRIPLAST and
other polyols
Polyol Elongation Hardness Impact Gloss ()
König pencil (cm.kg) (20) (60) (85) PRIPLA
ST 3195 290 108 4B gt 200 135 137 113 PRIPLAST
3195 with 3 TMP 300 114 B gt
200 166 141 118 HDO/NPG adipate 170 101 HB gt
200 152 125 113 HDO/NPG adipate/ dimerate
180 101 F gt 200 149 135 111 Commercial
PUD 273 120 B gt 200 158 138 114
Gloss measured in gloss units
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Stability of PU dispersions based on PRIPLAST
polyols
kept at 50C
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Benefits of PRIPLAST technology for PU dispersion
coatings
outstanding dispersion stability outstanding
weatherability and low moisture
absorption outstanding chemicals
resistance good flexibility, hardness and
gloss readily manufacturable
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PRIPLAST polyols for adhesives
For hot melts, reactive hot melts, polyurethane
dispersions for thermo-oxidative and hydrolytic
resistance for flexibility, also at low
temperatures for adhesion to low-energy
substrates for universal adhesion on a variety
of substrates
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Polyol effect of adhesion to steel final strength
of moisture cured adhesive
PRIPLAST products
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Polyol effect on adhesion to plastic final
strength of moisture cured adhesive
Untreated polyethylene 2.5 MDI/1 polyol
PRIPLAST products
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Advice on PRIPLAST polyols for adhesives
Specially recommended for applications with long
open time. Green strength is typically low
because of non-crystalline character, but
specialist advice is available to overcome
this moisture curing is slower because of
hydrophobicity
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PRIPLAST 3191 in water repellent, flexible PU
sealant foam

• Low water absorption, hence good water sealing
  properties
• Good hydrolytic resistance and compression set
  over conventional polyester foams, hence improved
  life cycle
• Low fogging
• Low air permeability, hence improved sealing
  properties

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Compression set of PU foam from PRIPLAST dimerate
vs. other polyols
Compression set after hydrolysis,
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Water seal test
100 mm
Water seal properties Leaking of water after
- PU from Priplast 3191 gt 24 hrs -
Conventional PU lt 10 min
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Water absorption test
Water absorption properties - PU from Priplast
3191 lt 1 V/V - Conventional PU 20 V/V
24 hrs. immersion in water
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Physical properties
Characteristic Priplast 3191 Conventional po
lyester polyester foam foam (low fogging
grade) Density, kg/m3 50
50 Water absorption (ASTM D 994) lt 1
gt 20 Water seal properties gt 24
hrs lt 10 min. Air permeability, litre /
min lt 15 50 Non fogging
properties - Reflectrometric method
96.6 85.1 (3 hrs / 100 C) -
Gravimetric method 0.70 mg
0.95 mg (16 hrs / 100 C)
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Application of PRIPLAST 3191 based foams

• Automotive industry, sealants for
• Airconditioning systems
• Windows
• Head and tail lamps
• Mirrors
• Door locks
• Sun roofs
• General industry, sealants for
• Airconditioning and ventilation
• Roof windows
• Refrigerators

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Starting formulation
(a) Tegostab B-8002, ex. Th. Goldschmidt (b)
Dispersant ex. Uniqema (c) Tertiary amine
catalyst ex. Osi Specialities
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Choosing the PRIPLAST polyol that is required
2 categories partially crystalline products
3192, 3195 amorphous products 3190, 3196, 3197,
3198, 1838, 1839 partially crystalline crystalli
nity gives additional tensile strength (esp.
3192) crystallinity gives green strength in
adhesives crystallinity is good for hydrolytic
stability crystallinity comes with lower
ingredient cost (because of adipic) amorphous fo
r adhesion to non-polar substrates and
compatibilizing with non-polar matrices for low
glass transition temperatures (pressure sensitive
adhesives, very flexible coatings)
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PRIPOL 2033 , dimerdiol

• Specifications
• acid value max. 0.20 mg KOH/g
• saponification value max. 2.0 mg KOH/g
• hydroxyl value 202 - 212 mg KOH/g
• colour APHA max. 50 Hazen
• moisture max. 0.10
• monomer alcohol max. 2.0
• dimer alcohol min. 96.5
• trimer alcohol max. 1.5
• viscosity typically 2500 mPa.s at 25 C
• MW approx. 540

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PRIPLAST polyester polyolsportfolio
3192 semi-crystalline best hydrolytic stability
(like polycarbonate diol), MW 2000 best
tensile strength (similar to PTMEG), best green
strength. for coatings, elastomers,
adhesives 3195 semi-crystalline, cheaper
alternative to 3192 (slightly less for MW
2000 hydrolytic stability, green strength,
tensile strength) 3190 amorphous, MW
2000 adhesives and coatings for low-energy
substrates applications that require a very
low Tg (-20C and lower) users that require a
low-viscosity liquid 3196 amorphous, MW
3000 compatibilizing, pressure sensitive
adhesives 3197 amorphous compatibilizing 3198 amo
rphous, MW 1300 coloured, for adhesives, primer
coatings 1838 amorphous, MW 2000 pressure
sensitive adhesives, compatibilizing 1839 amorphou
s, MW 2000 coloured cost-effective alternative to
1838 3191 amorphous, MW 1700 water-repellant foam
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PRIPLAST polyester polyolsspecifications
PRIPLAST acid value OH-value Colour Moisture mg
KOH/g mg KOH/g Gardner 3192 max.
0.5 52-60 max. 2 max. 0.1 3195 max.
1.0 52-60 max. 2 max. 0.10 3190 max.
1.0 52-60 max. 2 max. 0.08 3196 max.
0.5 34-40 max. 2 max. 0.1 3197 max.
0.5 52-60 max. 2 max. 0.08 3198 max.
1 78-88 max. 6 max. 0.01 1838 max.
1.0 52-60 max. 2 max. 0.08 1839 max.
1.0 52-60 max. 6 max. 0.08 3191 0.7-1.5 68-73
- max. 0.07