Showa Denko K.K. | A chemical company with individualized products.
Versatile Monomer
AOI-VM
TM
Asymmetry, Multi-Functional Hybrid Monomer
O
NCO
O
APPLICATIONS
Photo curing / Dual-cure | Copolymerization
paintings, coatings, adhesives, ink, etc…
MERITS
Easy to insert curable C=C group
High UV reactivity, Isocyanate reactivity
High performance as monomer & polymer
-1-
Introduction
Feature
Showa Denko succeeded to establish its brand new continuous production process of AOI in
large scale, which enable us to offer this to our customers.
To make our focus clear, we named this product AOI-VM™, VM means Versatile Monomer,
for industrial application.
We believe that AOI-VM™ will help to develop new products with higher performance and
lower environmental damage.
・Effective for UV/LED/EB/Heat/Dual
Curing. High reactivity.
・Can copolymerize with
various types of monomers
High reactivity as same as
aromatic isocyanate
O
O
NCO
2-Isocyanatoethyl acrylate, >96%
CAS # 13641-96-8
Regulatory
Appearance
Colorless or light yellow transparent liquid
Odour
Pungent (isocyanate)
EU (REACH)
(Now <1000MT/Y)
P.R.China (IECSC) In Progress (Now <1000MT/Y, Closed List)
US (TSCA)
(NO SNUR)
S. Korea (ECL)
Japan (ENCS)
R.O.C. Taiwan (ECN)
A) When polymerizing double bond first
B) When making NCO group react first
O
O
O
NCO HO
O
O
N
H
O
OH
O
O
Polymers (oligomers) with pendant
NCO can be easily prepared.
COOH
COOH
Polymers (oligomers) and monomers with
pendant acryloyl group can be easily
synthesized.
Merit for
• Easy resin design
• Polymers / Oligomers with pendant NCO or acryloyl group
• Reduce reaction steps
• Reduce solvent (VOC)
• High UV sensitivity
• Sharp molecular weight distribution
• Low viscosity polymer synthesis
• Making polymer high-performed
-2-
High NCO reactivity
HEA-HDI
Reactivity of NCO group (%)
AOI-HD
50
Copolymerization (%)
Basic Application Data
High UV reactivity
40
AOI-HD
30
O
O
N
H
O
H
N
O
O
O
O
O
20
HEA-HDI
O
O
10
O
O
0
TDI
80
AOI
60
HDI
40
IPDI
20
hydrogenat
edMDI
O
H
N
N
H
100
O
0
O
0
O
100
200
300
400
500
600
Time (min)
0
200 400 600 800 1000
Amount of exposure (mJ/cm2)
Toluene solvent, 60℃, Non-catalyst
Relative reactivity of NCO with n-BuOH, NCO/OH = 1/3 (mol)
Irg184, 5mol% Diluted by MMA (twice)
One-step reaction with reduced
byproducts and low viscosity
IPDI + HEA oligomer (2steps reaction)
Mw 31300 Viscosity 35000mPa・s
(Theoretical molecular weight Mw 10570)
AOI oligomer (1step reaction)
Mw 9470 Viscosity 93mPa・s
GPC Chart
mV
mV
(Theoretical molecular weight Mw 8960)
50
50
25
25
0
0
20
22
24
26
28
30
20
22
24
26
28
30
min
min
Base polymer (OH pendant polymer)
Mw 7800, Viscosity 53mPa・s
Anti-scrubbing
Self-mending
100
70
Coatings on iron plate, like automotive
Scratched
by coin
80
60
60
50
Tg　℃
80
● Anti-scrubbing
/ gloss
耐擦傷性：　光沢保持率％
retention (%)
120
40
40
■
20
30
0
300
400
500
600
700
20
800
After one hour
self-mended
Inter crosslinking
point molecular weight (g/eq)
架橋点間分子量　ｇ／ｅｑ
High NV, Reduced VOC
40
6H
6
5H
5
35
4H
4
45
30
33H
25
2H
2
20
1H
15
0
HB
10
B
-1
5
-2
2B
0
300
400
500
600
700
-3
3B
800
押傷が復元する限界鉛筆硬度
◆ Pencil
hardness
when wound restored
Impact resistance
■ Weight(200g) falling height
耐衝撃性：　落錘高さ　at 200ｇ
(cm)
Performance of Paintings/Coatings
Sharp molecular distribution and low viscosity can be obtained
in a single step reaction with AOI-VM.
Urethane acrylate made from AOI-VM without solvent : Clear, Low
viscosity
架橋点間分子量　ｇ／ｅｑ
Inter crosslinking
point molecular weight (g/eq)
By crosslinking, impact resistance is
controlled
*NV=Non Volatile Organic Compound
A reacted oligomer with Poly(caprolactone) diol (Mw3360)
-3-
SHOWA DENKO K.K.
Specialty Chemicals Department
13-9 Shiba Daimon 1-chome, Minato-ku,
Tokyo, 105-8518
Japan
TEL: +81 3 6402 5080
FAX: +81 3 5403 5730
URL: www.sdk.co.jp/english
Karenz: www.karenz.jp
SHOWA DENKO EUROPE GmbH
Konrad-Zuse-Platz 3
81829 Munich
Germany
Tel.: +49 89 93 99 62 0
Fax: +49 89 93 99 62 50
URL: www.showa-denko.com
SHOWA DENKO AMERICA, INC.
420 Lexington Avenue, Suite 2335A,
New York, NY 10170
U.S.A.
Tel.: +1 21 23 70 00 33
Fax: +1 21 23 70 45 66
URL: www.showadenko.us
KOREA SHOWA CHEMICALS CO.
Sunhwa Tower 2F, 43, Sejong-daero 7-gil,
Jung-gu, Seoul 04511
Korea
TEL : +82-2-3454-1831
URL: www.sdkksc.co.kr
SHOWA DENKO (Shanghai) Co., Ltd.
18F Wang Wang Building, No.211,
Shimen Yi Road, Shanghai 200041
China
TEL : +86-21-6217-5000
URL: sdsh.showadenko.com
Revised: Jan 2016
Issued by Showa Denko K.K.
Spec Chem Department
-4-
*The information contained
herein is based upon data
considered true and accurate.
However, SHOWA DENKO K.K.
accepts no responsibility or risk
which may result from the
handling and use of products or
for infringement of any patent.
CAUTION
AOI-VM™ may not be used for
any medical, pharmaceutical
and/or body contact application.
If in doubt, please contact your
sales representative.