Acrylic pressure-sensitive adhesives （PSAs） are widely used from industrial manufacturing processes to

commercial products because of their self-adhesion, weather and water resistances, and low cost.

Among these uses, industrial manufacturing processes require the acrylic PSAs to show high adhesive property

and easy peelability according to various situations and environments. Therefore, it is very interesting

to control the adhesive property and peelability of the acrylic PSAs by their chemical structures and external

stimuli such as light and heat. The control of the adhesive property by heat is useful because it is convenient

and easy to incorporate into the manufacturing processes. An acrylic PSA bearing a long alkyl side chain group

as its crystalline unit can control its adhesion because the crystalline unit undergoes a reversible order-disorder

transition with a change in temperature. By use of this reversible phase transition, it is possible to develop

a“ cool-off”（ CO） type adhesive that can be easily peeled off by cooling and“ warm-off”（ WO） type adhesive

that can be easily peeled off by heating. In this review, we introduce CO-type PSAs for high-temperature heat

resistance and a WO-type PSA with improved WO function that we have developed so far.

Highly tough epoxy resins modified with polyurethane for composite materials and adhesives of onecomponent

curing type using dicyandiamide were synthesized by in-situ method. As the 1st reaction，

bisphenol F type epoxy resin， polypropylene glycol and 4,4’-diphenylmethane-diisocyanate were charged

at 16 levels and reacted at 120 ℃ for 2 hours to synthesize urethane-pre-polymers. As the 2nd reaction，

1,4-buthane-di-ol of a chain-extender and the above urethane-pre-polymers were reacted at 120 ℃ for 2

hours to synthesize 16 levels of epoxy resins modified with polyurethanes having different rations of Hard

Segment : Soft Segment : Segment with n=1body of bisphenol F type epoxy resin added to the polyurethanes’

end. These epoxy resins modified with polyurethanes， bisphenol F type epoxy resin of an agent to control

the concentration of polyurethane， dicyandiamide of a hardener and 1,3,5-triazine-2,4,6（1H,3H,5H）-trione，

compounded with 6-2-（2-methyl-1H-　imidazol-1-yl）ethyl-1,3,5-triazine-2,4-diamine （1:1） of a curing

accelerator were mixed to prepare a one-component resin composition， which was then pre-baked at 120 ℃

for 45 minutes and post-baked at 150 ℃ for 45 minutes to obtain cured products. As a result of measuring the

properties， it was found that a cured product of an epoxy resin modified with 10 wt.% polyurethane， which

has 5 wt.% Hard Segment， 2.3 wt.% Soft Segment and 52.7 wt.% of Segment with n=1body of bisphenol F type

epoxy resin added to the polyurethanes’ ends， showed excellent properties suitable for composite materials

and adhesives of one-component curing type using dicyandiamide， i.e.， the fracture toughness was 1.87

MPa･m0.5， the tensile fracture elongation was 7.2 %， the tensile fracture strength was 67.6 MPa， the tensile

modulus was 2.2 GPa and the Tg（ DSC） was 132 ℃.

A novel crystalline polymer （DE-BP Polymer） was synthesized by reacting an epoxy resin having a diphenylene

ether structure （DGDE） with 4,4’-dihydroxybiphenyl. Then, the properties of DE-BP Polymer were

compared with those of the polymer from DGDE and 4,4’-dihydroxydiphenylether（ DE-DE Polymer）. The

melting point of DE-BP Polymer in differential scanning calorimetry was 245.6 ℃ , which was 59.8 ℃ higher

than that of DE-DE Polymer, and the glass transition temperature in dynamic mechanical analysis was

120.2℃ , which was 26.5℃ higher than that of DE-DE Polymer. In addition, the thermal conductivity of DEBP

Polymer was 0.33 W / m·K, which was higher than that of DE-DE Polymer.

An epoxy resin having a m-terphenyl structure（ DGMTP） was synthesized, followed by evaluating the physical

properties of the cured polymer with phenol novolac. The glass transition temperature was 160℃ , which

was 33℃ higher than that of bisphenol A type epoxy resin （DGBPA）, and 4 ℃ higher than that of biphenyl

type epoxy resin （DGTBP）. In addition, the char yield at 700℃ was 29.2 wt%, which was significantly higher

than 15.6 wt% of DGBPA, and the 10 wt% weight loss temperature was 404℃ . These results indicate higher

thermal stability of the DGMTP cured polymer based on a m-terphenyl structure.