Latest developments in bio plastics (thermosets)

Latest developments in
bioplastics (Thermosets)
Jokin Hidalgo, TECNALIA
Alvaro Tejado (TECNALIA), Maider Azpeitia (TECNALIA),
Alejandro Salvador (TECNALIA).
www.innobite.eu

Donostia - San Sebastian

20/02/2014

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Why we talk bio-plastics?

Latest developments in bioplastics

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Driving forces: Sustainability
"Sustainable development is development that meets the needs of the
present without compromising the ability of future generations to
meet their own needs.
(World Commission on Environment and Development, 1988)

“El desarrollo sostenible se define como el desarrollo que satisface las
necesidades del mundo actual, sin comprometer las necesidades de las
generaciones futuras.”
(Comisión mundial del medio ambiente y del desarrollo, 1988)

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Driving forces Consumers
forces:

DuPont Industrial Biosciences, “China Green Living Survey,” 2012.
http://biosciences.dupont.com/china-green-living-survey/
Task X.Y


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Driving forces: Governments Country

Acronim

Web

Austria

ÖNORM

www.as-search.at

Spain

AENOR

www.aenor.es

France

AFNOR

www.afnor.org

Germany

DIN

www.din.de

Italy

UNI

www.uni.com

Japan

JIS

www.jsa.or.jp/default_english.asp

UK

BSI

www.bsigroup.com

US

ASTM

www.astm.org

International

ISO

www.iso.org

Europe

CEN

www.cen.eu

Standardisation bodies associated with the production of standards of biodegradability of plastics

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Driving forces: Generally Accepted Ecolabels.


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Driving forces Clear up misunderstandings
forces:


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forces:


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forces:


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forces:


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Driving forces: Global interest
Growing interest in all indexed books related to bioplastics and biocomposites.

Ngram Viewer


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Driving forces: Research - Patents


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Driving forces: Research - Patents


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Driving forces: Market


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http://www.plasticseurope.es

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http://www.plasticseurope.es

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Plastemart, “Bio based plastics on the rise”
http://www.plastemart.com/upload/Literature/Demand-for-bio-based-plastics-rising.asp

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Driving forces: Future lack of resources

http://www.oilposter.org/

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History


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History


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History
▪ 1839, Charles Goodyear and his brother Nelson discovered the
vulcanization of natural rubber.

▪ 1846 Christian Schönbein produced nitrocellulose.
Then Alexander Parkes get the Parkesine, and John Wesley Hyatt the
celluloid
▪ 1907, Leo Hendrik Baekeland, an American of Belgian origin, developed
the first truly synthetic polymer, a thermoset polymer resulting from the
reaction of phenol with formaldehyde.


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History


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History


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Bioplastics:

http://en.european-bioplastics.org/

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Bioplastics: Market



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Bioplastics: Market


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Biorefinery: Resources from renewable sources.


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Biorefinery: From almost everywhere…
We can extract raw materials to generate useful biopolymers, from almost all the
tree of life, as we can read in the next articles:

Vegetables: “Polysaccharides from Wastes of Vegetable Industrial Processing”.
Animals: “Animal Waste for the Production of Biofuels and Biopolymers”.
Fungi:

“Are mushrooms the new plastic?”

Micro algae: ”Making plastics from algae”.
Bacteriums: “Researchers Train Bacteria to Convert Bio-Wastes Into Plastic”.


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Biorefinery:
Diagram of possible applications of polymers obtained from bio refining processes of cereals and pulses.

R. Wool and X. Sun, Bio-based polymers and composites. Elsevier, 2005

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Biorefinery:


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Bio-based polymers:
Natural rubber
Starch
Poly (lactic acid)
Poly (hydroxyalkanoates)
Poly (butylene succinate)
Poly (γ-glutamic acid)
Glycosaminoglycans
Proteins

Cellulose
Hemicelluloses
Lignin

Chitin / Chitosan
Task X.Y


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Bio-based polymers:
Polyolefins
Polyesters
Polycarbonates
Polyamides
Methyl acrylate
Poly (vinyl chloride)
Thermosetting resins: polyurethanes,
polyester, epoxy, phenolic, alkydic.
Task X.Y


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Bio-based polymers:

Task X.Y


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http://www.nova-institut.de

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Bio-based polymers:


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Bio-based polymers:

Mono-Ethyleneglycol (MEG)


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Bio-based polymers:
Other C2 based building blocks:
Acetic acid

Dichloroethane (formed by chlorination of ethane)
Vinylchloride (formed by dehydrochlorination of dichloroethane)
Ethylene oxide (oxidation of ethylene)
Ethylenediamine (reaction of 1,2-dichloroethane and ammonia)


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Bio-based polymers:


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Bio-based polymers:

Ethyl Lactate


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Bio-based polymers:

Propylene Glycol (1,2-Propanediol)

,
coolants and antifreeze, hydraulic and brake fluid, aircraft
de-icing fluid, heat transfer fluids, paints and coatings.


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Bio-based polymers:
DuPont formed a joint venture with
agriculture products company Tate & Lyle

1,3 Propanediol

Susterra® PDO: products from textiles to coatings
and engineering plastics.
Susterra® PDO is co-polymerised with terephthalic
acid to produce poly(trimethylene) terephthalate
(PTT) sold by DuPont under the trade name Sorona®
.
Sorona® PTT has been targeted at clothing, carpet
and automotive textile markets.
Cerenol™ polyols based on PDO can be used in
variety of applications from personal care and
functional fluids to performance coating and
elastomers.

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Bio-based polymers:

Production of resins and polymers (mainly epoxy
resins (76%) )
Epichlorohydrin


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Bio-based polymers:

Epichlorohydrin

Glycerol


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Bio-based polymers:

Isopropanol production via fermentation and its
conversion into propylene have been reported by
Mitsui Chemicals, INC.
Isopropanol

Propylene


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Bio-based polymers:

n-Propanol

Recently a Braskem patent was published which
describes the fermentative production of npropanol and the subsequent dehydration into
propylene.

Propylene


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Bio-based polymers:

Coatings, adhesives, sealants, textiles, fibres,
polymer additives/impact modifiers, super
absorbent polymers…
Acrylic acid


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Bio-based polymers:

n-Butanol

Succinic Acid

Methyl methacrylate


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Bio-based polymers:


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Bio-based polymers:

Succinic Acid


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Bio-based polymers:

Furfural

Levulinic acid

Isoprene

Xylitol

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Bio-based polymers:

Lysine

Adipic acid

Glucaric acid


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Bio-based polymers:

2,5-Furandicarboxylic acid (FDCA)

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Bio-based polymers:

Sorbitol
Isosorbide

Task X.Y


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Bio-based polymers:

p-Xylene


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Bio-based polymers:
Fatty Acid derivatives

Lubricants, metal-working fluids, fuel additives,
personal care products, corrosion inhibitors,
rheology modifiers…


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Bio-based polymers:


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Bio-based polymers:

Task X.Y


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Bio-based polymers:

Tannin-based
Bark of various trees.

Review of existing bioresins and their Applications (Jim Dewar)2007

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Bio-based polymers:

Lignin:
and

resin,
.

Lignin: 5-50%
of the wood.

(For PF) Barrier to commercial development if different blends and source of lignins
are going to give different properties.
Review of existing bioresins and their Applications (Jim Dewar)2007
Task X.Y


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Bio-based polymers:

R. J. A. Gosselink, “Lignin as a renewable aromatic resource for the chemical industry,” 2011.

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Bio-based polymers:
Lignin:

resin

Plasticsengineeringblog, “Rumplestiltskin Wanted,” Plasticsengineeringblog,
http://plasticsengineeringblog.com/2012/11/12/rumplestiltskin-wanted/

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Bio-based polymers:

Cashew Nut Shell Liquid (CNSL)

,

and

Review of existing bioresins and their
Applications (Jim Dewar) 2007

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Bio-based polymers:

Triglycerides

Triglycerides consist of three fatty acids (i.e., carbon numbers from 22 down to
14 and double bonds down from 3 to 0) covalently linked to a central glycerol.

Chemistries available for turning such oils into useful polymeric products
(Amines, monoglycerides, polyols, maleates, acrylates , epoxy, hydroxyl, and
maleate half esters .


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Bio-based polymers:
: from Soya Oil …

: Bio 1,3-propanediol from corn dextrose via
fermentation…

: Variety of renewably sourced raw materials.

: From renewable resources like corn, linseed oil,
soy, canola…
Isosorbide, propylene glycol, glycerin, industrial
ethanol and ethylene glycol…


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Bio-based polymers:
Prepregs: sustainable, fire
retardant prepregs suitable for composite applications.
Similar performance to phenolic.
Derived from hemicellulose crop waste such as sugar
cane bagasse.

derived from naturally occurring pine oil.

Bio-based
(ortho-, iso-, and terephthalic,
dicyclopentadiene (DCPD) modified and bisphenol A
fumarate) and
.

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Bio-based polymers:
Polyols for

.

Dimer diamine for use in both thermoplastic
as well as curative in thermoset
and
systems.

Polymerised fatty acids. Dimer diol building block with high
di-functionality provides good colour, water repellency,
flexibility, thermo-oxidative and UV stability and
outstanding hydrolysis / chemical resistance for
and
coatings, adhesives and
elastomers.
and
resins from cardanol [Industrial
oily alkyl-phenolic product obtained by vacuum distillation
of "cashew nut shell liquid" (CNSL)].

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Bio-based polymers:

Companies commercializing novel
pathways to biobased commodity
chemicals:
February 2014 / Pathways to novel chemicals
http://www.aocs.org/Membership/informArticleDetail.cfm?itemnumber=19304


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Bio-based polymers:

Task X.Y


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Bio-based polymers:

http://materia.nl/article/worlds-first-biobased-facade/

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Bio-based polymers:

Task X.Y


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Bio-based polymers:

Task X.Y


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Bio-based polymers:

Task X.Y


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Bio-based polymers:

http://abcnews.go.com/Technology/ford-makes-car-lined-coke-bottle-material/story?id=20904665

http://www.dieselpowermag.com/tech/ford/1109dp_fords_bio_plastic_techology/photo_01.html
Task X.Y


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Bio-based polymers:

en.wikipedia.org
Task X.Y


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Thank you
www.innobite.eu
INNOBITE is co-funded by the European Community
Seventh Framework Programme for European Research and
Technological Development (2012-2015)

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Driving forces: Governments - Standards
Title
CEN/TR 16208:2011 Biobased products- Overview of standards

Mandate TC
M/429
___

CEN/TR 15932: 2010 Plastics - Recommendation for terminology and
characterisation of biopolymers and bioplastics

___

CEN/TC 249 2010-03-24

CEN/TS 16137:2011 Plastics - Determination of bio-based carbon
content

M/430

CEN/TC 249 2011-04-27

CEN/TR 16227:2011 Liquid petroleum products – Bio-lubricants –
Recommendation for terminology and characterisation of biolubricants and bio-based lubricants

M/430

CEN/TC 19

CEN/TS 16295:2012 Plastics - Declaration of the bio-based carbon
content

M/430

CEN/TC 249 2012-02-15

CEN/TS 16398:2012 Plastics - Template for reporting and
communication of bio-based carbon content and recovery options of
biopolymers and bioplastics- Data sheet

M/430

CEN/TC 249 2012-10-31

Task X.Y

Presentation Title

Publication Date
2011-05-04

2011-08-10

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Driving forces: Governments - Standards
Title

Mandate TC

prEN 16575 Bio-based products - Vocabulary
FprCEN/TS 16640 Bio-based products - Determination of the
bio-based carbon content of products using the radiocarbon
method
CEN/TR xxxxx Bio-based products - Overview of available and
possible methods and techniques for determination of the
total bio-based content of products
TS xxxxx Bio-based products - Bio-based solvents Requirements, application classes and test methods
EN xxxxx Bio-based products - Sustainability criteria

M/492
M/492

Expected
Publication Date
CEN/TC 411 2014-12-30
CEN/TC 411 2014-02-22

M/492

CEN/TC 411 2014

M/491

CEN/TC 411 2015

M/492

CEN/TC 411 2016

EN xxxxx Bio-based products - Life Cycle Assessment

M/492

CEN/TC 411 2016

EN xxxxx Bio-based products - Determination of the biobased content - Method based on the 14C content and
elemental X.Y
Task analysis
Presentation Title

CEN/TC 411 2016
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