G2-14

Dopamine Acrylamide, as an UV Adhesive
Material Found out in Biodiversity
M. Matsuno皿d R. Akaishi
Osaka Organic Chemical Industry LTD., Katayama-cho, Kashiwara City, Osaka Japan
Abstract-- In a bio-inspired catechol monomer, dopamine acrylarnide (DopAm) and 4-(methacryla1nido)phenylboronic acid (4MAPB), those surface affinities were investigated by quartz crystal microbalance (QCM) measurements. To each surface ofSi02 andAg, DopAm and 4-M紐B had greater adhesive capacity than 4-hydroxybuthyl acrylate (4-HBA), methacrylic acid (Mん�). and so on.
Subsequently, in UV-curing surface adhesions to ABS, glass, and ITO (coated on glass), a polymer contaii1ing only I wt% ofDopAm
was adhered more effectively than that containing the same an1ount of4-M紐B. Furthermore, when each O.Swt% ofDopAm and 4MAPB were used at once, the effect was most enhancement for glass and ITO. Finally, ill UV-curing tacky adhesions, a co-polymer
containing DopAm was also more effective tl1an that containing 4-MAPB for pairs ofdissimilar materials, i.e., PET/Cu and PET/Al,in which the synergistic effect ofDopAm and 4-MAPB was found in the same as UV-curing surface adhesions.

I. INTRODUCTION

II. TECHNICAL WORK PREPARATION

From the perspective of biodiversity, there are various
adhesive mechanisms which are in Gecko legs, wildburdock fruit, mussels, etc. In mussels, L-dopa has acatechol group is an important adhesive component [I](Fig. l ).

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胄•

暑．．＇,,
クふ． 、、；｀.
ヽ,.>.· <--:·｀- ‘ _·，し安ふ←-こミ)Muss出’’:CocN;b)L-Dopa
HOHOµ。

℃こc)DopAm●Fig. I a) Mussels and each structure ofb)しdopa and c) Dop 知
We focused on L-dopa, dopamine [2], and dopamine
acrylamide(DopAm)(Fig.l) as a biomimetic adhesivemonomer, which are corresponding to a rare case of an
artificially chemical evolution. DopAm and its analogues
were studied well about an adhesive gel [3], ananoimprint lithography [4), a dental adhesive in eugenol
monomer [5], and so on. And as another chemistry,
catechol groups and boric acid produced correspondingboric acid esters by equilibrium reactions [6], which wereused for cross linking i11 polymers [7] and various
applications [8, 9]. From our previous report, in eco­friendly UV curing without solvents, when a small
amount of Dop.Ain was used with main monomers,
surface adhesiveness to mate1ials and tacky adhesivenessfor pairs of diss面Jar materials were more improved thanthose without DopAm [10). 1n this study, somesynergistic e:ffects were found with DopAm and 4(methacrylamido)phenylboronic acid (4-MAPB). The
properties of DopAm with 4-MAPB were introduced indetail and its application pot.ential was discussed.

A. Chemicals and Materials
Commercially available chemicals as solvents werereagent grade and used without further purification. 2Methyl-2-propenoic acid [i.e., Methacがic acid(MAA)]
and its esters(Mitsubishi Chemical Co. Ltd.), N-(2-(3,4dihydroxyphenyl)ethyl]prop-2-enamide [i.e., dopamine
acrylamide(DopAm)] and acrylate esters(Osaka Organic
Chemical Indus切Ltd.) [11] were also used as received
from the manufactttrers. [4(2-methylpropー2-enoylamino)
phenyl]boronic acid [i.e., 4(methacrylamido)phenyl­ーboronic acid (4-MAPB)] and 2-[4-(2-methylprop-2enoylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2dioxaborolane (pinacol-protected4-MAPB)
wereprepared by dehydration of the ainines as these precursors
皿dMAA with l-ethyl-3(3-dimethylaminopropyl)ーcarbodiimide hydrochlo1ide(EDC · HCI).
In cross-cut peel tests for surface adhesion, ABS resinplates(Type: N, thickness: 2.0mm)(Taiyukizai Co., Ltd.),soda-lime glass plates(thickness: 0.7mm)(Foresight Co.,Ltd.), indium tin oxide (ITO)-coated glass plates(thickness: 0.7 mm/glass, 0.13µm/ITO)(EHC Co., Ltd.)
were used. In the peel tests for su1face adhesion, anadhesive tape(Cellotape™, Nichiban Co., Ltd.) was used.
In the 180° peel tack tests, polyester (PET) films(Lumirror 60, thickness: 75µm)(Toray Industries, Inc.),
PP plates(Type: N, thic畑ess: 2.0mm)(Taiyukizai Co.,Ltd.), Cu plates(Type: FR-4R 1700, thickness: 1.6mm)(Taiyukizai Co., Ltd.), and Al plates (Type: A1050P,thickness: 0.8mm)(Nippon Testpanel Co., Ltd.) wereused. The surfaces of these materials were cleaned withacetone or ethanol before use.
B. Instruments and Experiments
A 9 MHz quartz c1ystal microbalance (QCM)
measurements were performed on a SEIKO EG&G
QCA922 analyzer. In the UV-curing, monomers orm以tures were coated on sample plates with RDS Mayer
Coating Bar No. IO(coating thickness: 22.9µin) and wereexposed to a Heraeus LIGHT HAMMER 10 UV system.