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 2.3
S udy o he e e sion/ deg ada ion o CAN
Con ac ual Da e o Deli e y: 31/12/2024
Ac ual Da e o Deli e y: 30/12/2024
Lead con ac o o his deli e able: WR
Au ho (s):
(ICSO), Gio gio To ani, Filipa A. Vicen e (NIC),
Ghazal Ta akoli, A ijana Susa, Willem Vogelzang,
Wou e Teunissen, Ian Jansen, He man Beukelae
(WR)
Pa icipan s(s):
WR, ICSO, NIC
WP con ibu ing o he deli e able:
WP2
Na u e: Con iden ial
Ve sion V. 3
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Execu i e Summa y
This epo p o ides a summa y o he wo k conduc ed unde Task 2.3 o he
ESTELLA p ojec , which ocused on s udying he e e sion and deg ada ion o
Co alen Adap able Ne wo ks (CANs) and in es iga ing he ep ocessabili y and
ecycling e iciency o a ious CAN-based ma e ials. NIC concen a ed on he
ep ocessabili y o bio-epoxy esins con aining associa i e CANs, analysing hei
ecycling e iciency and he ma e ial p ope ies pos - ecycling. ICSO ocused on
he deg ada ion o he epoxy i ime ma e ials also inco po a ing associa i e
CANs by subjec ing he ma e ials o dissolu ion and depolyme iza ion in he
p esence o sol en s ia anses e i ica ion a high empe a u es. Capabili y o
e-c osslinking o he he mose s was also analysed. Meanwhile, WR ca ied ou
a comp ehensi e s udy on he e e sion and deg ada ion o he mose s
con aining Diels-Alde (DA) unc ionali ies, examining he pa ame e s ha
in luence he ep ocessabili y o dissocia i e CANs. The esea ch yielded
impo an indings on he e e sion and deg ada ion beha iou s o bo h
associa i e and dissocia i e CAN-based esins, p o iding aluable insigh s in o
hei ep ocessabili y and po en ial o sus ainable applica ions. Below a e he
summa y o he main indings o he esea ch pe o med on e e sion and
deg ada ion o associa i e and dissocia i e esins.
Associa i e bio-based epoxy om lignin wi h CAN [NIC]
NIC has been s udying he ecycling and ep ocessing o lignin-based epoxy esin
con aining associa i e CAN. The e e sion and/o deg ada ion s udies o epoxy
esins wi h CANs was only pe o med o one ype o lignin-based epoxy esin
ins ead o wo, due o he subop imal p ope ies ob ained o he o he
de eloped epoxy esins, hei limi ed possibili y o scalabili y, and/o indings
co e ed in he Sa e and sus ainable by design (SSbD) epo . This applies o he
esin ob ained h ough he unc ionalisa ion o highe molecula weigh (MW)
lignin ac ions and c osslinked wi h 1,4-bu anediol diglycidyl e he o o m he
inal epoxy esin. Conside ing he ep ocessabili y, wo app oaches we e s udied.
In he i s one, he epoxy esin was dissol ed in g een sol en s, and he eshaping
was es ed. In his case, i was possible o eshape he epoxy esin. Howe e , he
ecycled ma e ial was oo b i le compa ed o he o iginal one. The second
me hod es ed he sel -healing p ope ies o he epoxy esin by ho p essing in
he p esence and absence o pu e esh epoxide (1,4 bu anediol diglycidyl
e he ). The esul s showed ha he ho p essing did no suppo he sel -healing
o he epoxy esin sample.
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Associa i e ossil epoxy esins wi h CAN [ICSO]
ICSO epo s he success ul de elopmen , cha ac e isa ion and ecycling o
epoxy i ime ma e ials ailo ed o mee bo h high pe o mance c i e ia and
sus ainabili y goals. By selec i ely combining pe ochemical epoxy esins wi h
bio-based modi ie s and op imising he cu ing agen composi ion (speci ically
con aining bo h acid and anhyd ide), he esea ch eam has achie ed
mechanical p ope ies and glass ansi ion empe a u es (Tg) ha mee he
p ojec equi emen s.
A key achie emen is he demons a ion o a cos -e ec i e chemical ecycling
p ocess using p opylene glycol as a sol en . This app oach enables cu ed epoxy
ma e ials o be dissol ed and he aw componen s eco e ed o euse.
Inco po a ing 15-20% ecycled ma e ial in o he new o mula ions e ained he
desi ed p ope ies while educing ma e ial was e. These indings highligh he
po en ial o indus ial-scale implemen a ion, ad ancing he p inciples o a
closed-loop economy in he polyme indus y.
Dissocia i e biobased DA-con aining esins [WR]
WR p esen s he main indings o hei esea ch in he con ex o s udying he
e e sion and deg ada ion o Diels-Alde (DA) bonds and pa ame e s in luencing
he ep ocessabili y o he dissocia i e CANs. Acco dingly, he "back- o-
monome " e o-Diels-Alde ( DA) p ocess o he selec ed o mula ion in esponse
o hea as s imulus was s udied in de ail. The WR-selec ed he mose
demons a ed excellen ep ocessabili y, success ully unde going ex usion o a
leas i e cycles while main aining a high eco e y a e o he mal and
mechanical p ope ies. Comp ession moulding p o ed o be a less p e e ed
app oach o he ep ocessing o some o he o mula ions.
Rema kably, empe a u e was shown o play a c ucial ole on he success ul
ep ocessabili y o he DA-con aining he mose s. Acco dingly, i was no iced
ha a highe empe a u es, he ex en o he iscosi y d op equi ed o
ep ocessing o ma e ial, is lowe ed mo e d as ically a e e e y cycle. In
addi ion, e en hough he minimum iscosi y eco ded a lowe empe a u es
was highe (making ep ocessing less con enien ), he deg ee o he es o a ion
o DA bonds seemed o be g ea e , and he deg ee o deg ada ion o DA
unc ionali y seemed o be much smalle . These indings highligh he impo ance
o op imizing ep ocessing empe a u es o balance ecycling e iciency and
ma e ial longe i y.
A sys ema ic s udy o ac o s a ec ing DA bond e e sibili y and he mose
ep ocessabili y was also pe o med and e ealed:
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- Inc easing DA bond concen a ion imp o es low beha iou abo e he
DA h eshold bu equi es an op imal le el o balance
he mal/mechanical p ope ies wi h ep ocessabili y. Excess
concen a ion comp omises pe o mance.
- C osslink densi y has a s ong in luence on he ep ocessabili y as well as
he mal and mechanical p ope ies o ma e ials. The compe i ion
be ween c osslink densi y and DA bond clea age signi ican ly a ec s
ma e ial ep ocessabili y and p ope ies. Ou s udies e ealed ha
beyond a ce ain c osslink densi y, he ma e ial's low beha iou becomes
independen o DA bonds. The e o e, he balance be ween hese ac o s
mus be ca e ully ailo ed o achie e desi ed ou comes.
- The posi ion o DA bonds also impac s ep ocessabili y. DA bonds in he
c osslinke appea o enhance ep ocessabili y, hough u he s udies a e
equi ed o comp ehensi e unde s anding.
These insigh s collec i ely suppo he de elopmen o mo e ecyclable DA-
con aining he mose s wi h ex ended usabili y.
Taken oge he , he D2.3 deli e able has success ully me all ou lined objec i es,
scope o impac , as speci ied in he G an Ag eemen . Howe e , a mino delay
in submission has occu ed due o he ex ended imelines in p eceding in e -
connec ed asks and he upscaling ac i i ies o ce ain pa ne s.
