• Rapid Communication in Photoscience
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• v.2 no.1
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• pp.24-27
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• 2013

A polymeric photobase generator containing oxime-urethane groups is applied to a fluorescence micropatterning material. Polymer bearing oxime-urethane groups was prepared by copolymerization of methyl methacrylate with methacryloyloxyethyl benzophenoneoxime urethane (MBU). The reaction of amino groups in the irradiated copolymer film with dansyl chloride (Dns-Cl) was monitored by using UV absorption, IR absorption and fluorescence spectroscopy. The fluorescence spectrum of the Dns-Cl-treated irradiated copolymer film shows a strong fluorescence with a fluorescence maximum wavelength at 510 nm. A blue fluorescent micropattern with a line width of $2{\sim}3{\mu}m$ was obtained. Treatment of the irradiated copolymer film with Dns-Cl and rhodamine B mixture led to the formation of green, red, and orange-colored fluorescence micropatterns. Thus, various colored micropatterns on a single polymer film can be obtained by selective excitation of each dye molecules.

• Bulletin of the Korean Chemical Society
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• v.21 no.7
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• pp.690-696
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• 2000

Epoxy copolymers containing oxime urethane groups were prepared by the polymerization of glycidyl methacrylate and N-[5-(benzophenoneoximinocarbonylamino)pentanyl]maleimide (BOPM). Their physical properties were characterized by GPC, DSC and TGA analyses. Photochemical changes of the copolymers were studied by UV, IR spectroscopy, and contact angle measurements. A photoinduced cross-linking reaction in copolymer films was observed by measuring the insoluble fraction. Irradiation of the copolymers at 254 nm UV light leads to the formation of pendant amino groups by photodissociation of the oxime-urethane groups. Treatment of the amino groups with HCl resulted in the formation of ammonium salts, which changed the polymer surface to be hydrophilic. An insoluble fraction of the copolymers increased with irradiation time, heating time, and heating temperature. Cross-linking of the epoxy resin effectively catalyzed by the photogenerated pendant amines upon heating.

• Macromolecular Research
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• v.14 no.3
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• pp.300-305
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• 2006

The chemical structure of a semi-aromatic polyimide-I, which was prepared by the chemical imidization of cyclopentanetetracarboxylic dianhydride and 2,2-bis(4-aminophenyl)hexafluoropropane, was characterized by $^{13}C-NMR$ spectroscopy. The chemically imidized polyimide-I was used for the preparation of a photosensitive polyimide (PSPI) through the addition of benzophenone and benzophenone oxime hexamethylene diurethane (BOHD), a photobase generator containing oxime-urethane groups. The polyimide-I film containing benzophenone and BOHD was not soluble in 2.38 wt% tetrabutylammonium hydroxide solution in $H_2O$. However, it became soluble following irradiation with 310 nm UV light. A positive tone image with a resolution of $5{\mu}m$ was obtained with this PSPI, having sensitivity($D_c$) of $1.2J/cm^2$ and contrast(${\gamma}_p$) of 1.08. Thus, a polyimide, which is not intrinsically photosensitive, can become photosensitive through the addition of a photobase generator containing oxime-urethane groups as a photosensitive compound.

• Macromolecular Research
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• v.12 no.4
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• pp.352-358
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• 2004

For their application as one-component photoresists, we prepared epoxy terpolymers containing oxime-urethane and benzophenone groups by the radical polymerization of glycidyl methacrylate (GMA), metha-cryloxyethyl benzophenoneoxime urethane (MBU), and N-(4-benzoyl)phenylmaleimide (BPMI). The terpolymer composition was optimized to provide the most photosensitive photoresist. The photo-decomposition reaction of the oxime-urethane groups in the terpolymer was monitored by UV absorption spectroscopy, and the photo-crosslinking reaction of the epoxy terpolymer was observed by measuring the normalized thickness. The photosensitivity of the epoxy terpolymer increased as the amount of BPMI and MBU units increased up to 16 and 24 mol%, respectively. Among the terpolymers we prepared, terpolymer T-II(contents of GMA, MBU, BPMI are 75, 19, 6.1 mole%, respectively) exhibited the highest photosensitivity ( $D_{c}$ $^{0.5}$ = 430 mJ/$\textrm{cm}^2$) and had a moderate contrast (${\gamma}$$^{p}$ = 1.23). Negative-tone micropatterns having a line width of ca. 10 ${\mu}{\textrm}{m}$ were obtained by developing the system with chloroform.m.

• Proceedings of the Korean Society of Potoscience Conference
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• 2002.06a
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• pp.29-29
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• 2002

• Proceedings of the Polymer Society of Korea Conference
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• 2006.10a
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• pp.177-177
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• 2006

Copolymers containing oxime-urethane groups, which led to the formation of pendant amino groups photochemically, were applied to a fluorescent image-recording material through the reaction with fluorescamine, a prefluorescent dye for amino groups. This imaging method permits the fluorescent image to be erased or restored by treatment with base or acid. Copolymers containing phthalimide carbamate groups were applied to a bicolor fluorescent imaging material through the consecutive reaction with fluorescamine and rhodamine. A various colored fluorescent micropattern (green, red or red-yellow) was observed through the changes of excitation wavelength by using a conforcal microscope.