Vestamid Terra - BIO · Existing applications areas Novel applications areas Substitution Unique...

High Performance Polymers

Growth Line – Resource Efficiency

Dr. Benjamin Brehmer

18.06.2013, World Biocongress, Montreal

VESTAMID® Terra

What is in store for bio-

based polyamides?

Source:World Congress on Industrial Biotechnology, Montreal, 2013 page | 2

Layout

Ecological aspects

Conclusion

a

b

c

d

e

Chemistry and supply chain of bio-based polyamides

Introduction to biotechnology at Evonik

Commercial products and application fields


Evonik is the creative industrial group from

Germany, but is active worldwide

A worldwide presence


It is important to understand and innovate in all

three distinct biotech segments

The segments of biotechnology

White Red

Green

Source: OECD


Evonik is currently active in all three segments of

the bioeconomy

RED

• Health – delivery systems, medical devices

• RESOMER®

WHITE

• Industry – polymers and adhesision

• DYNACOLL® Terra

• VESTAMID® Terra

GREEN

• Agriculture – amino acids

• Biolys®

• ThreAMINO® and TrypAMINO®

Bioeconomy activities at Evonik


Evonik is focused on producing and achieving

high-performance for petro and biopolymers

Co

st D

rive

n

Pe

rfo

rma

nce D

rive

n

Engineering

High-performance

Commodity

Amorphous Crystalline

Petro-based Polymers Bio-based Polymers

PEEK

PPA

PPS

PA12

PA612

PBT

PET

PA6/66

PUR

POM

PP

PE-LD PE PE-HD

PE-UHD

LCP

PA46

PAI

PPSU

PEI PMI

PI PES

PMMI

PSU

tPA

PMMA

PPE

PC

ABS

SAN

PS PVC

PE

PP

PLA PHA/B

PTT/3GT

PPA

PA1010

PA1012

PA11

PA610

PA410

~230Mton ~1Mton

Capacity Source: PEMRG & European Bioplastics

The plastics pyramid

Polymers

Semifinished Products

Products from Evonik

Evonik’s

Focus

TPU

CA

PEF


In the world of biopolymers there are four

distinct categories which can be confusing

Biopolymer categorical breakdown

VESTAMID® Terra falls under durable and bio-based

Durable Biodegradable

Petroleum-based

Raw Materials

Biomass-based

Raw Materials

Conventional Polymers

• 99% all polymers

Biopolymers

• Resistant and bio-based

• e.g. PA1010, bio-PE

Biopolymers

• biologically degradable

and bio-based

• e.g. PLA, PHA

Biopolymers

• biologically degradable but

petro-based

• e.g. PBS, PCL

High performance

polymer based

wholly or partially

on renewable

resources

Castor Bean

Confusion still exists as the categories of biopolymer are not yet fully accepted / established

• Most people and/or customers associated biopolymers with biodegradability

• Many people and/or customers regard biopolymers as being recycled polymers


Layout

Ecological aspects

Conclusion

a

b

c

d

e





VESTAMID® Terra product line is based on a

combination of different monomers

Diamine (AA)

C6 H: Hexamethylene Diamine

C10 D: Decamethylene Diamine

AA-BB Biopolymers

Diacid (BB)

C10 S: Sebacic Acid

C12 D: Dodeconioic Diacid

D-G: Triple D-A (Bio-route)

Aromatic T: Terephthalic Acid

NH3H3N NH3H3N

NH3H3N NH3H3N

OHHO

O

O

OHHO

O

O

HO OH

O

O

HO OH

O

O

OH

O

O

PA610 (HS); PA612 (D); PA1010 (DS); PA1012 (DD); PA1012 (DD-G); PA10T (DT)

Bio-based Monomers

• C10 Diamine “D”

• C10 Diacid “S”

• C12 Diacid “D-G”

H2N

H2N

NH2

NH2

http://upload.wikimedia.org/wikipedia/commons/1/12/Terephthalic-acid-2D-skeletal.png


Fatty acid derivates can lead to a wide range of

different polyamide building blocks

Basic chemical derivation from fatty acids

Ricinoloeic Acid 12-Hydroxyoctadec-9-enoic acid

Undecenoic Acid 10-undecinoic acid

Sebacic Acid Octanedicarboxylic acid

Oleic Acid 9-Octadec-9-enoic acid

Azeliac Acid 1,7-nonanedioic acid

Natural Fats and Oils

Plant Species main oil composition / triacylglycerol

Main Isolated Acid after transesterification

Dimer Acid single acid chain

Di-acid double acid chain

Di-amine double amine end-groups

Route 1

Transesterification

Route 2

Amination

Dehyrdation

Hydrogenation

AABB Polyamide AB Polyamide

Polymerization

Polymerization

Castor Bean Ricinolein / triacylglycerol

Peanut Olein / triacylglycerol

Transesterification Transesterification

Caustic oxidation Thermolysis Ozonolysis Dimerisation

DMDA double amine end-groups

Amination

Dehyrdation

Hydrogenation

e.g. PA1010 e.g. PA11

Polymerization

Polymerization

Nonanoic Acid 1-octanedioic acid

NMDA double amine end-groups

Amination

Dehyrdation

Hydrogenation

e.g. PA99 e.g. PA10

Polymerization

Polymerization

Examples: existing / theory


Castor bean and castor oil are the common

source for all biopolyamides like AABB’s

Castor Bean/Oil Monomers Polymers Others

Supply chain of castor bean products and derivatives

Oilseed: ~1.5 Mton

Castor Oil: ~900 kton

Castor Oil Triacylglycerol

Meal/Cake Castor Beans Ricinus Comminus

Ricinoloeic Acid 12-Hydroxyoctadec-9-enoic acid

Glycerin

Undecenoic Acid 10-undecinoic acid

Heptaldehyde

2-Octanol

Sebacic Acid 1,8-octanedicarboxylic acid

Undecenoic Acid: 25 kton

Sebacic Acid: 100 kton

Polyamide 11 exclusively Arkema

VESTAMID® Terra Evonik AABB’s

DMDA Decamethylene diamine

AABB Polyamides PA410, PA610, PA1010, PA1012

Biopolyamides: ~50 kton

VESTAMID® Terra

Sebacic Acid: 75 Mton

Castor Oil: 700 kton

Polyester / ols

Plasticers

Lubricants

Lubricants

VESTAMID® Terra represents one of the many castor oil derivatives


VESTAMID® Terra DS

Polyamide 1010

Polymer

C-10 Diamine

Monomer

The synthesis of VESTAMID® Terra DS is based

solely on renewable feedstocks

Ricinus communis

Castor oil

Ricinoleic methyl ester + glycerine

Sebacic acid + Isooctanol

Monomer


Layout

Ecological aspects

Conclusion

a

b

c

d

e





The are three distant pathways to place

VESTAMID® Terra biopolymers into the market

Existing applications areas Novel applications areas

Substitution

• Tubing • Airbrake • Liners

Unique Performance Bio-Based

Mobility

• Backpanels • Barrier Sheets

Solar

• Powder Coating

Household

• Jacketing

Cables

• Toothbrushes • Carpets • Tires

Filaments

• Shoe Soles • Outdoor Apparel

Sports

• Fine Powders

Cosmetics

• Casings

Electronics

• Toughener • Impact Modifier • Matrix

Composites

• Thin Walled • Components

Electronics

• Flowability • Abrasion • Resilience • Flame Retardance • Water Absorption

.

.

.

Degree of relevant and/or potential volumes

Source:World Congress on Industrial Biotechnology, Montreal, 2013

Several product examples of extruded films and

foils based on VESTAMID® Terra

page | 15

Potential Industries Photovoltaic | Design | Packaging

Reflective backsheets

Flexible laminates Ski laminates / surface

Multi-layered systems Graphically appealing films


Several product examples of the flame retardant

grades of VESTAMID® Terra

page | 16

Potential Industries Electronics | Aeronautics | Building and Infrastructure

Cable boxes and clips

General housings

Lamp housing

Cable trunking systems

Aircraft interior parts


Several product examples of the fiber reinforced

grades of VESTAMID® Terra

page | 17

Potential Industries Automotive | Sports | Building and Infrastructure

Housing cage

Quick connectors

Window profiles and insulation

Rackets and sticks

Shoe soles, studs

© Technoform


Several product examples of multifilament

extruded products from VESTAMID® Terra

page | 18

Potential Industries Carpet | Reinforcement | Textiles

Tiles; micro tufted

Residential wall-to-wall

Sports apparel

Lines and Strings

Tire cord and carcasses

Bandages (USP* approved)

*United States Pharmacopeia (USP) Class VI material classification

© Fotolia, Lovegrove


Several product examples of monofilament

extruded products from VESTAMID® Terra

page | 19

Potential Industries Bristles | Strings | Filters

Toothbrush

General cleaning bristles

Paper Machine Fabrics

Lines and strings

Racket Sports

Tee or Coffee Filters

Membranes for Hot-air Balloons


Several product examples of the extrusion grade

of VESTAMID® Terra

page | 20

Potential Industries Automotive Tubing | Cable Jacketing | Pipes

Pneumatic (airbrake) lines

Fluid (coolant, diesel, clutch) lines

Liners and tubes

Optical wire cables

Rodent / ant resistant


Several product examples of the injection

molding grade of VESTAMID® Terra

page | 21

Potential Industries Sports | Small Components | Automobile

Shoe soles, liners

Winter sport boots

Quick Connectors

Electronic housings

Accessories, optical / writing / time

Interior elements


Several product examples of application based

on the fine powder VESTOSINT® Terra

page | 22

Potential Industries Cosmetics | Composites / Coatings | Additive Manufacturing

Crèmes as oil dispersant

Sunscreens and moisturizers Epoxy toughener

Fluidizing bed coating

Rapid prototyping, design objects, etc.


Layout

Ecological aspects

Conclusion

a

b

c

d

e





Feedstock End-of-life

recycle/disposal Product use

Production

Gate-to-gate

Cradle-to-gate*

Cradle-to-cradle/grave

Global warming Global warming

Global warming Global warming

Acidification

Acidification

Acidification Acidification

Eutrophication

Eutrophication Eutrophication

Eutrophication

Ozone depletion

Ozone depletion

Ozone depletion

Ozone depletion

…

… …

…

LCA

CF

Imp

act ca

teg

orie

s

While an LCA has different impact categories, the

scope defines the type of LCA

LCA: Life cycle assessment; CF: CO2eq over 100years

The main (customer) focus is on the carbon footprint (CF)

*The cradle-to-gate is used for polymers to the point of compounding and pellet production

Sco

pe

Structure of life cycle assessments


Overview of carbon footprint of several polyamides

The VESTAMID® Terra line has a lower carbon

footprint than the petro-based nylons

Source: external publications, internal calculations with PE Int. Databank (Oct 2010)


4,1

0

1

2

3

4

5

6

7

87,3

2,6

7,3

LCA internally calculated by Evonik

Reference data (fossil)

GaBi PA610 granulate

Through downstream technical and procurement

improvements, the CF can be further reduced

Example: Improved LCA of VESTAMID® Terra HS (PA610)

The reduction of the carbon footprint (CF) can increase from 43% to 64%

Hydropower can also be purchased for an additional reduction of around 25%

CO2-Equiv. / kg PA 610

2,0

7,3

PA 610

Classical polymerization PA 610

melted sebacic acid

polymerization

PA 610

melted polymerization &

purchased hydropower


Layout

Ecological aspects

Conclusion

a

b

c

d

e





The choice to employ VESTAMID® Terra products

is based on balancing attributes

Relative comparisons of key physical attributes of polyamides


VESTAMID® Terra is

• Made from plant (bio-sourced)

• Environmental friendly

• Reduces global warming potential

• High performing

• Commercially available in diverse grades

• Competitive against existing polyamides

VESTAMID® Terra

because we care…

Conclusion

Vestamid Terra - BIO · Existing applications areas Novel applications areas Substitution Unique...

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