SBIR/STTR Phase II: New Approaches to Using Renewable

SBIR/STTR Phase II: New Approaches to Using Renewable

SBIR/STTR Phase II: New Approaches to Using Renewable Biomass Derived Materials in Epoxy and Vinyl
Ester Resin Products to Reduce Styrene and Other Petroleum Based Raw Materials.
Grant Number:
Award Dates:

DMI-0521976

Tetramer Technologies. L.L.C. Overview

September 1, 2005 - August
31, 2007.

Award Type:

SBIR Phase II

Topic:

BT

Company Name:Tetramer Technologies, L.L.C.
Address:

657 S. Mechanic Street,
Pendleton, SC 29670

PI:

Tetramer Technologies was formed in 2001 as a faculty-driven start-up
company commercializing high value research activities pursued at Clemson
University. It currently employs 11 people- 9 PhDs, 1 Masters, and 1 BS
level.

Competitive Advantages and Critical
Customer Needs Addressed with Tetramer
Technology

Our business model is to focus on developing specialty polymeric or
oligomeric materials through synthesis, structure/activity development, in
close research development relationships with device or other downstream
customers.

The last three years have provided a tipping point of
price differential between non-renewable crude oil and
renewable vegetable oils. This trend is finally establishing
chemicals from biorefineries as more price competitive
with products from crude oil refineries.

Dr. Earl H. Wagener

Technical Objectives/Goals

Tetramer has developed technology which uses renewable
resource biomass raw materials which can be tailored for desired
end use properties in thermoset markets, such as vinyl ester
resins, epoxies, and urethanes.

Copolymerization of LAHEMA with a commercial VER/Styrene

Using biomass derived materials, such as
unsaturated vegetable oil and racemic lactide,
develop new product applications which substitute
significant amounts of petroleum based raw
material in commodity thermosets such as epoxy
resins, unsaturated polyester resins, and
polyurethane.

Meets or exceeds current VOC environmental regulations by
lowering styrene content in vinyl ester resin up to 50% with no
loss in performance.
Can use lower cost racemic lactide raw material.

Replace up to 25% of styrene in vinyl ester resins.
Develop lower cost acrylic derivatives.

Market Opportunity

Technical Results to Date
Vinyl Ester market worldwide is $ 300 MM. Epoxy, urethane and
unsaturated ester markets are > $1 Billion

Synthesis of LAHEMA

Customers collaborations underway with Ashland, Reichhold,
Cargill, 3G Mermet, Battelle, Rohm and Haas, and Dow
Global Styrene regulations have proposed even more reductions

O

Ph

O
Ph

N
H

O

O
O

O
O

O

0

O
O

O

O
O

O

H2
C

OCN

O

AA
COOH

O

OH

O

O

n

O

O

O

n

O

O

O

O
O

O

21

28

Viscosity of VER/Styrene formulations
(42 44 wt % VER) with different LAHEMA
contents for replacement of styrene.

UPR
diacrylate
crosslinker

O

14

w t % LAHEMA

O

O

O

O

3000
2500

150
125

3415.3

100

3246.8
3161.5

75

35

50
0

5

10

15

20

25

w t % LAHEMA

O

O

O

3401.4

141.6

Finance and Revenue Model
Stage 2 and 3 Development will be achieved through Phase IIB
Joint Development Agreements with Target Customers through
2008
Initial Scale-up to 2 - 3 MM lbs will be accomplished locally with
contract manufacturers in 2008-2009 producing revenue streams
of $1.4 - $ 2.1 MM from sale of product

O

O

O

7

O

LAHEMA
HO

NCO

3500

143.9

2000

0

MDI

4000

45-0-54

H2
C

142.2

145.6

Polymer composites are growing due to weight, performance,
and cost vs. steel

Flexural Strength (MPa)

N
H

175

24-21-54

RO

200

4500

25-17-58

GMA

343.2

200

31-12-57

O

375.6

5000

Styrene-LAHEMA-VER

O

O

O

Flexural Modulus (MPa)

O

O

400

30-28-42

x

O

434.8

35-21-44

O

y z

600

Styrene-LAHEMA-VER

Scope of LAHEMA

800

45-0-54

K in em atic Visco sity (cSt)

Properties of Vinyl Ester Resin (VER) with and without LAHEMA

O

O
O

O
O

O

OH

n

Flexural properties of VER/Styrene
formulations (5458 wt % VER) with different
LAHEMA contents for replacement of styrene.
Filled blue circles represent flexural
modulus, and orange squares represent
flexural strength. Lines indicate leastsquared fits to the data.

Scale up to 10 - 25 MM lbs. will come from local VC firms or
customer manufacturing (producing a royalty stream)

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