biotech forum february 9, 2011 improved performance sugar-based chemistries for biomedical...
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Biotech Forum
February 9, 2011
Improved Performance
Sugar-Based Chemistries for Biomedical Applications
BPA Replacement
Water Uptake
High Use Temperature Polyesters
Low Molar Mass Designer Compounds
M. Jaffe, A. J. East, W. Hammond, X. Feng, P. Saini
New Jersey Institute of Technology
Improved Performance
Sugar-Based Chemistries for Biomedical Applications
BPA Replacement
Water Uptake
High Use Temperature Polyesters
Low Molar Mass Designer Compounds
M. Jaffe, A. J. East, W. Hammond, X. Feng, P. Saini
New Jersey Institute of Technology
2
Overview
IsosorbideIsosorbide
Backbone Modification
Coatings and Adhesives
Isosorbide was developed as a polyester backbone modifier: Raises Tg, lowers dX/dt in PET for next generation package (Hoechst, DuPont) Thermosets
isosorbide diglycidyl ether for bis-A free
epoxies
Low molar massCosmetic and Polymer
Additives
UV Stabilizers, Plasticizers,
humectants, anti-oxidants
Thermoplastics
Polyesters Polycarbonates
Polyamides Polyurethanes
New Monomers and polymers
New AB Monomers with
controlled stereochemistry
Tm=61°C, Tb=160°C, GRAS, 8 kilo soluble 1 liter water
Medical Adhesives, soluble drugs,
Performance biomaterials
3
Isosorbide Chemistry
• Isosorbide reactivity and stereochemistry is complex but can be exploited Unequal reactivity of pendent hydroxyls (endo-exo) allows
asymmetric substitution with stereochemical controlo New stereoregular AB monomers
– New stereoregular polyesters
o New approach to ester backbone modificationo Low molar mass multifunctional “designer” compounds
Isosorbide thermodynamics allow for epimerization reaction to isoidide (exo-exo)
Isosorbide is a precursor to isoidide stereochemistry Glucose isosorbide, other sugars not investigated (yet) Strong IP position
Fast
Slow
Isosorbide Isoidide
4
Isosorbide-based Epoxy Replace BPA
•Dry mechanical properties similar to Bis A epoxy
•Water uptake <1% to > 50%
O
O
H
H O
O
O
O
H
HO
O
OH
OO
(R)
O
O
(S)
O
O
O
O
Water soluble before crosslinking
5
Isosorbide Compounds Water Uptake
• Observations Isosorbide-based epoxy networks are
capable of significant water uptake o Current data ranges from < 1% to > 50%
– Target is application dependent but < 1% is often desired
o Reacting free OH with isocyanates to produce polyoxazolidones significantly lowers water uptake
Isosorbide based polyesters are not noticeably hydroscopic
o Large PEIT databaseo AB monomerso Stereochemically controlled PisosT.
PisoiT Cinnamic acid esters, fatty acid esters,
hydroxy acids are not noticeably hydroscopic
• Conclusion: Isosorbide water uptake is a function of the local chemical environment and is controllable
Bisisosorbide diglycidyl ether
O
O
O OO O
OH
O
O
O O
Bisisosorbide triglycerol
O
O
OO
O
OH
O
O
OOH
OH
OHOH
F 3C C O O H
H 2O
High Water Uptake
O
O
H
H O
O
O
O
H
HO
O
O
ON
O
NO
O
R R
NH
OR
Low Water Uptake
Medical Adhesive
PEG Replacement
6
Isosorbide - Thermoplastics
Polycarbonates Replace bis-phenol A Improve thermal performance
• Polyesters Improved performance for commodity polyesters, Raise
Tg New stereoregular polymers New LCPs with renewable disrupters, mesogens
• Polyurethanes
7
Controlled Stereochemistry Isosorbide/Isoidide Monomers and Polymers
Poly(isoidide phenyl ether)
• Advantages Controlled stoichiometry,
stereochemistry New group of high performance
semicrystalline polyesterso Tg>150 °C, Tm>300 °Co Low water uptake
Will works with all condensation polymers tp increase Tg
o Reduced sublimation, reduced color Biocompatible, Resorbable
compositions New patent platform
O
O
OH
O R
O
OH
O
O
O
OH
OR OH
O
8
Commercial Polymer Backbone Modification with Isosorbide: Next generation
• New High Use Temperature Homopolymers, Tg > 150 C, Tm ~ 300C+ Controlled stereochemistry based on AB monomers Esters or ether ester backbones
• Modify PET To Increase Tg TA + EG + AB Transesterify PET + AB Poly(AB) + PET Control modifier Stereochemistry
• Modify PLLA To Increase Tg Isosorbide based AB monomer Decouple backbone relaxations to increase Tg Raise IV to increase toughness
• New LCPs Disrupters Mesogens
40
60
80
100
120
140
160
0 0.2 0.4 0.6 0.8 1
Tg as f[(Poly(isoTA)]
PLLA
(calculated)
O
O
O
O
R
O
n
O
R =
Isosorbide series
O
O
HO
OH
O
O
HO
OH
OH
Diadzein Genistein
9
Low molar mass compounds
• Bis compounds UVA, UVB absorbers Plasticizers Anti-oxidants Thermoset monomers
• Asymmetric substituted (“designer”) compounds UVA-UVB UVA-plasticizer Plasticizer-Cl scavenger Limited by utility All new compositions of
matter
UV Absorbance of all synthesized sunscreens
-10000
0
10000
20000
30000
40000
50000
60000
250 300 350 400 450 500
wavelength(nm)
exti
ncti
on
co
eff
icie
nt
Seri es1 Seri es2 Seri es3 Seri es4 Seri es5 Seri es6 Seri es7 Seri es8 Seri es9 (1) (12) (6) (10) (11) (3) (7) (9) (14)
Not water solubleStable to 300 °C+
10
Support
• Companies Food packaging Surfactants and solvents for personal care UV absorbers for cosmetics High performance polyesters (in progress) BPA free low water uptake epoxies (in progress) Improved polyester fiber
• Agencies Sustainable liquid crystalline polymers
11
Conclusions
• Sugar derived compounds possess unique, exploitable stereochemistry
• Isosorbide provides a ubiquitous platform of cost-effective chemistries for biomedical applications and Isosorbide isomers
• A proprietary technology platform is being created Isosorbide Isoidide