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
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
E alua ion o ecyclabili y o
he de eloped ma ices
DELIVERABLE 4.1
Con ac ual Da e o Deli e y: 31 Oc obe 2024
Ac ual Da e o Deli e y: 29 Oc obe 2024
Lead con ac o o his deli e able: FEYECON (FEY)
Au ho (s):
Ma ia F.P. Schonhe , Daniela T ambi as (FEY), Mª
Dolo es
Rami ez (AND),
,
Na alia Bie na (ICSO), Filipa Vincen e
, Gio gio To ani
(NIC)
Pa icipan s(s):
FEY; AND ISCO, NIC
WP con ibu ing o he deli e able:
WP 4
Na u e: Con iden ial
Ve sion V. 5
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA-Deli e ables_4.1.V5
©ESTELLA - 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.
he ein.
Execu i e Summa y
The wo k desc ibed in his epo was ocused on he ecyclabili y o epoxy
esin ma ices de eloped wi hin he Es ella p ojec by means o di e en
ecycling me hods. The expe imen s we e conduc ed in he p ojec
pa ne s loca ions (FeyeCon (FEY), Andal ec (AND), Ins y u Ciezkiej
Syn ezy O ganicznej Blachownia (ICSO), and Na ional Ins i u e o
Chemis y (NIC) in he pe iod M17-M29. The deli e able exhibi s some ime
de ia ions conce ning he analysis o ecycled ma e ials and he
op imiza ion o ecycling p ocesses. This delay was caused by se backs in
epoxy ma ices syn hesis (wo k conduc ed in T2.2). Despi e hese
limi a ions, no signi ican impac on he o e all p ojec implemen a ion is
an icipa ed. The comple ed wo k has success ully me i s objec i es as
ou lined in he g an ag eemen by iden i ying p omising ecycling
me hods and de ailing he p elimina y cha ac e is ics o ecycled
ma e ials, he eby p o iding a solid ounda ion o con inued e o s in Task
4.4.
Objec i es
In he ESTELLA P ojec , Task 4.1 is desc ibed as ollows:
ecyclabili y in o de o selec in T2.4 wo ma ices o he composi e
ab ica ion in T4.3 (one wi h he mos exigen equi emen s and ano he
wi h less demanding ones)". The main objec i es o hese asks we e o
de elop ecycling me hods ha we e ailo ed o b eak he co alen
adap able ne wo k uniquely p esen in each o he de eloped ma ices
and assess hei ecyclabili y based on he changes in hei p ope ies. Fo
his pu pose, scCO2-assis ed and chemical ecycling p ocesses we e
selec ed o be in es iga ed.
Key ou comes
1. Diels-Alde esin (Composi ion: DGEBA+ u u ylamine+ BMI-689):
a. scCO2-assis ed ecycling: The addi ion o scCO2induced swelling
and oaming, accele a e he s uc u al disin eg a ion o he ma ix
and acili a es he dissolu ion o he esin (Figu e 1). The ecyclabili y
assessmen is s ill ongoing.
Figu e 1. DA esin: O iginal shape (le ), a e scCO2-assis ed ecycling:
disin eg a e (middle le ), oamed (middle igh ) and dissol ed ( igh )
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA-Deli e ables_4.1.V5
©ESTELLA - 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.
he ein.
b. Chemical ecycling: Dissolu ion was obse ed when acidic
solu ion (e.g., Cy ene/wa e / a a ic acid (TAR) o u u ylamine
we e used as sol en a p ocessing empe a u e o 80-90 C
(Figu e 2).
Figu e 2. Diels-Alde esin dissolu ion in acidic sol en s (le and
middle) and u u ylamine ( igh ) a e ea men .
2. Epidian 6-based esin wi h a ious composi ions de eloped by
ICSO: The ma ix can be ei he pa ially o o ally dissol ed mainly in
glycol sol en s. The ecycling empe a u es can a y signi ican ly
om 60 o 180 0C, depending on he p esence o absence o
addi ional co-sol en /ca alys and he ini ial c oss linke s. The
p ocess in ol es e apo a ing he sol en using o a y e apo a o
and adding esh c osslinke o he concen a ed ecycled esin,
allowing he dissol ed oligome s/monome s o be eused (Figu e 3).
Figu e 3. Example o E-6-based esin dissolu ion in glycol (middle) and
ecycled esin concen a e ( igh )
3. NIC esin (Composi ion: Func ionalized lignin + 1,4-Bu anediol
diglycidyl e he (B14DODGE): Despi e simila CAN bond wi h ICSO
esin, he ecyclabili y o his sample was sligh ly di e en , only
limi ed o no dissolu ion obse ed in glycol. The esin ma ix can be
ecycled by using o he ypes o sol en s like bio-based dipola
he e ocyclic cycloalkanones ep esen ed by Cy ene wi h acidic
ca alys such as p- oluenesul onic acid and TAR in combina ion wi h
small amoun o wa e (10% / ) using a empe a u e anged om
80-180 C. The ecycled esin was able o be eshaped o he
o ma ion o new esin (Figu e 4).
G an Ag eemen 101058371 P ojec ESTELLA
ESTELLA-Deli e ables_4.1.V5
©ESTELLA - 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.
he ein.
Figu e 4. F om le o igh : o iginal NIC esin, ecycled esin, emoulded
samples 1 ( om exp 14) and 2 ( om exp 18).
4. Cha ac e is ics o ecycled esins: In gene al, changes in he
he mal p ope ies o ecycled esins we e obse ed. This
obse a ion is based on he decline o glass ansi ion empe a u es
(all esin ypes) and mel ing empe a u e (DA esin). No all he
ecycled ma e ials ha e been analysed ye due o he delays in he
deli e y o he pa ne s.
Conclusions
The esul s om Task 4.1 success ully demons a ed he easibili y o
ecycling epoxy ma ices con aining speci ic CAN bonds, de eloped by
he Es ella p ojec pa ne s wi hin he p omised imeline. This ecyclabili y
is e idenced by he dissolu ion o hese esins in chemical sol en s unde
milde condi ions compa ed o con en ional epoxy esins. Howe e ,
u he in es iga ions a e equi ed o e alua e whe he he key
cha ac e is ics o hese ma ices, pa icula ly hei mechanical p ope ies,
can be e ec i ely p ese ed a e ecycling. The subsequen wo k on
hese ma e s will be con inue in Task 4.4 and going o be epo ed in mo e
de ailed in D4.4.
