G an Ag eemen numbe : 101058371
P ojec ac onym: ESTELLA
P ojec i le: Design o bio-based he mose
polyme wi h ecycling capabili y by
dynamic bonds o bio-composi e
manu ac u ing
DELIVERABLE 2.4
Epoxy esin selec ion
Con ac ual Da e o Deli e y: 31 Oc obe 2024
Ac ual Da e o Deli e y: 31 Oc obe 2024
Lead con ac o o his deli e able: ICSO
Au ho (s):
Bie na (ICSO),
Gio gio To ani, Filipa A. Vicen e
(NIC), Ghazal Ta akoli Gheinani, Willem
Vogelzang (WR), Ma ia Schonhe , Daniela
T ambi as (FEY), (AND)
Pa icipan s(s):
ICSO, NIC, WR, FEY, AND
WP
con ibu ing o he deli e able:
WP2
Na u e: Con iden ial
Ve sion V. 5
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA_D2.4_ 5
- This is he p ope y o ESTELLA Pa ies: shall no be dis ibu ed/ ep oduced wi hou o mal app o al o ESTELLA Gene al
Assembly.
The Communi y is no liable o any use ha may be made o he in o ma ion con ained he ein.
Execu i e Summa y
The wo k desc ibed in his epo ocused on he selec ion o epoxy esin ma ices
de eloped wi hin he ESTELLA p ojec o upscaling, based on he mechanical
and he mal p ope ies o he p oduc s, as well as hei ecycling po en ial. Task
2.4 is desc ibed as ollows:
T2.4 Selec ion and p oduc ion o he epoxy esins o mula ions [ICSO, NIC, WR]
(M22-M29)
In his ask he esul s o he he mal and mechanical analyses o T2.2 and he
ecyclabili y esul s o T4.1 will be compiled in o de o selec hose ha mee he
g
and he eco e y o 65% o ma ices a e ecycling p ocess). This will lead o he
syn hesis and p oduc ion o wo inal selec ed epoxy esin o mula ions scaled up
o p oduce enough ma e ial. Fo associa i e CAN sys ems, his will be 15kg pe
esin. O iginally, his amoun was es ima ed a 25-30kg o bo h he high-
pe o mance and he low pe o mance esins. Howe e , a e p oducing he
di e en associa i e epoxy esins and cha ac e ising hem, i became clea ha ,
wi h he p ope ies ob ained o he la e , he e would be no sui able applica ion
wi hin he p ojec o he low pe o mance esin. The e o e, scaling-up his esin
would no be an e icien use o esou ces and ime. Mo eo e , based on he
bes o mula ions de eloped so a wi hin he p ojec , i became e iden ha
upscaling he p ocess o p oduce 25-30kg o hese esins would be challenging
and ime-consuming. A he same ime, educing his amoun o 15kg will in no
way hinde he success ul comple ion o he p ojec objec i es, so he p oposed
amoun o epoxy esin was educed. In case he dissocia i e CAN sys em is
selec ed, WR will scale up o 1kg, which allow o ep ocessing/ ecycling
ac i i ies. In he case o dissocia i e CANs, i was also no ed ha he mos
p omising epoxy esin equi es a complex p ocedu e ha p e en s scaling up o
3-5kg, wi h 1 kg being su icien o scaling up.
Below a e he main indings o he esea ch on syn hesis and ecycling o
associa i e and dissocia i e epoxy esins.
Associa i e bio-based epoxy om lignin wi h CAN [NIC]
Conside ing he de elopmen o associa i e bio-based epoxy om lignin wi h
CANs, wo dis inc pa hways we e explo ed: i) eac ion be ween lignin
monome s ( anillin and sy ingaldehyde) and a ious diamines o c ea e imine
bonds (Schi bases), ii) unc ionaliza ion o highe molecula weigh (MW)
ac ions o lignin de i ed om so wood K a lignin o c ea e es e and e he
bonds.
Conside ing he p ojec objec i e, only one epoxy esin ul ils wo o he equi ed
equi emen s o Tgand elonga ion a b eak. In he ecycling o lignin-based
epoxy esin de eloped by NIC, no dissolu ion was obse ed using glycol as
a sol en . The dissolu ion o his ype o ma ix we e obse ed when cy ene and
combina ion o Cy ene-wa e we e used as sol en oge he wi h he p esence
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA_D2.4_ 5
- This is he p ope y o ESTELLA Pa ies: shall no be dis ibu ed/ ep oduced wi hou o mal app o al o ESTELLA Gene al
Assembly.
The Communi y is no liable o any use ha may be made o he in o ma ion con ained he ein.
o acidic ca alys s such as p-TSA ca alys and TAR. Howe e , none o he di e en
app oaches allowed he comple e dissolu ion o he bio-based epoxy esin.
Associa i e ossil epoxy esins wi h CAN [ICSO]
Epoxy i ime s de eloped by ICSO we e based on he low-molecula weigh
ossil epoxy esin, c osslinked wi h ca boxylic acids and/o anhyd ides in ing
opening condensa ion eac ion. Epoxidized plan oils we e used as eac i e
diluen s o modi y p ope ies o esin. The use o a mix u e o c osslinking
subs ances, speci ically a combina ion o acid and anhyd ide allowed o he
mee ing o p ojec equi emen s o glass ansi ion empe a u e Tg, ensile
s eng h and Young modulus. The elonga ion alue was no achie ed, as his
would ha e o be a he expense o de e io a ion o he o he pa ame e s.
Signi ican e o s we e de o ed o de eloping an e icien p ocess o he
chemical ecycling o cu ed epoxy esins based on Epidian-6. The cu ed epoxy
ma e ial was comple ely dissol ed in p opylene glycol. The dissolu ion p ocess
was ca e ully moni o ed o ensu e comple e depolyme iza ion o he c oss-linked
esin wi hou chemical deg ada ion o he monome s.
Dissocia i e ecyclable esins [WR]
WR de eloped syn hesis o epoxy ma e ials con aining Diels-Alde bonds, using
Diels-Alde mechanisms, ocusing on he use o bio-based aw ma e ials and
ecycling po en ial. The he mal beha io o he de eloped he mose s is
a c i ical pa ame e o selec ing he op imal o mula ion, gi en he in ended
applica ions o Es ella ma e ials. Amongs he ma e ials de eloped by WR, some
o mula ions exhibi glass ansi ion empe a u es (Tg) ha a e nea he speci ied
ange o Es ella ma e ials. Also, h ee o mula ions possess a bio-based con en
exceeding o app oaching 60%. Addi ionally, hese h ee o mula ions ha e
mechanical p ope ies ha mee he es ablished c i e ia, u he suppo ing hei
sui abili y o he a ge applica ions. Howe e , heological s udies e ealed ha
none o he o mula ions exhibi ed he necessa y iscosi y d op equi ed o
e ec i e ecycling o ep ocessing. Fu he mo e, a emp s by o he pa ne s o
ecycle o mula ion A, as one o he bes pe o mance o mula ions, h ough
chemical o mechanical me hods we e unsuccess ul.
Conclusions
A e e iewing all he obse a ions and esul s, and e alua ing he easibili y o
syn hesizing hese he mose esins, i was concluded ha none o WR's
o mula ions will be selec ed o scale-up in his p ojec . In e alua ing he di e en
o mula ions de eloped by NIC, speci ically hose using lignin monome s and
lignin i sel o p epa e bio-based epoxy esins con aining CANs, i was de e mined
ha he o me did no mee he sus ainabili y equi emen s. Among he ou
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA_D2.4_ 5
- This is he p ope y o ESTELLA Pa ies: shall no be dis ibu ed/ ep oduced wi hou o mal app o al o ESTELLA Gene al
Assembly.
The Communi y is no liable o any use ha may be made o he in o ma ion con ained he ein.
o mula ions o he la e , only one showed po en ial; howe e , e en his op ion
did no ully mee all o ESTELLA's equi emen s.
In con as , he ossil-based epoxy esin ma e ials being de eloped a ICSO
demons a ed e y good mechanical p ope ies and ecycling po en ial. As
a esul , he o mula ion de eloped a ICSO was selec ed as he inal composi ion
wi h he po en ial o la ge -scale implemen a ion.
This D2.4 deli e able has me i s objec i es, wi h he excep ion o selec ing he
dissocia i e CAN sys em. I was concluded ha he o mula ions de eloped by
WR did no mee he p ojec 's equi emen s and would no be selec ed o scale-
up. This decision was based on a comp ehensi e analysis o he da a and
alignmen wi h he p ojec objec i es. Conside ing he p ope ies o all he
de eloped sys ems, i was decided o upscale only he ossil-based epoxy
i ime . Acco ding o he amendmen o he G an Ag eemen , i was also
de ia ion in ime and plan o he Deli e able.
