Biocompatible, drug-loaded anti-adhesion barrier using visible-light curable furfuryl gelatin derivative

Kim, Eun-Hye,Kim, Jae-Won,Han, Ga-Dug,Noh, Seung-Hyun,Choi, Jae-Hee,Choi, ChangSun,Kim, Mi-Kyung,Nah, Jae-Woon,Kim, Tae-Yeon,Ito, Yoshihiro,Son, Tae-Il Elsevier 2018 INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES Vol.120 No.1

<P><B>Abstract</B></P> <P>Recently, many of studies have been attempted to determine how to decrease adhesion. To effectively prevent adhesion, decrease in unnecessary surgical procedures, prevention of contact with other tissue, and drug treatment for inflammation are required. However, current anti-adhesion materials have disadvantages. To solve current problems, we prepared a biocompatible drug-loaded anti-adhesion barrier using a visible-light curable furfuryl gelatin derivative. We used riboflavin as a photo-initiator in the photo-curing process. The biocompatibility of riboflavin was estimated compared with that of Rose Bengal. In addition, the curing ratio was measured to determine whether riboflavin initiated photo-curing. We also evaluated the curing ratio of riboflavin according to the concentration of F-gelatin and the photo-irradiation time. A drug used to decrease inflammation that causes adhesion should not disappear from the surgical site and should also be released consistently. For this, we observed the release profiles of photo-immobilized ibuprofen with different concentrations of F-gelatin. Because an anti-adhesion barrier should protect from bacterial infection we evaluated the protective ability of a barrier formed by F-gelatin. In conclusion, a drug-loaded anti-adhesion barrier was prepared using a visible-light curable furfuryl gelatin derivative, with riboflavin as a photo-initiator. We expect that this drug-loaded anti-adhesion barrier effectively decrease adhesion formation.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Riboflavin showed the better photo-curable property and biocompatibility as photo-initiator than Rose Bengal. </LI> <LI> As concentration of furfuryl gelatin and photo-irradiation time increase, the photo-curing ratio increase. </LI> <LI> Release profile of photo-immobilized ibuprofen can be controlled by changing the concentration of furfuryl gelatin. </LI> <LI> Surgical site can be protected from bacterial infection by furfuryl gelatin barrier and adhesion also can be decreased. </LI> <LI> Drug-loaded anti-adhesion barrier can protect surgical site and prevent inflammation. </LI> </UL> </P>

광경화 아크릴레이트 단량체의 복합경화 특성

배진우(Jin Woo Bae),정재현(Jae Hyun Jung),왕혁식(Hyuck Sik Wang),김석현(Seok Hyeon Kim),김일중(Il Joong Kim),김익재(Ik Jyae Kim),송기국(Kigook Song) 한국고분자학회 2017 폴리머 Vol.41 No.2

광경화와 열경화능을 가진 아크릴레이트 단량체를 사용하여 광경화-열경화 또는 열경화-광경화의 순서에 따른 경화속도 변화를 고찰하였다. Isocyanatoethyl acrylate(ICEA)와 2-hydroxyethyl methacrylate(HEMA) 처럼 광경화와 열경화 메카니즘이 다른 단량체 혼합물에 먼저 UV에 의한 광반응을 진행한 후, 2차로 열경화를 하는 복합경화시스템을 조사하였다. 이 경우 1차 광경화에 의해 고분자 사슬이 형성되면, 2차로 열경화에 의해 우레탄 반응에 참여하는 관능기들이 고분자 사슬에 묶이게 되어 열경화에 의한 우레탄 반응을 더 높은 온도에서 진행하여야 하며, 전환율도 낮아지는 것을 확인하였다. 반면에, 같은 조성의 혼합물에 열경화를 먼저 진행하고 광경화를 하는 복합경화의 경우에는 열경화에 의해 우레탄 아크릴레이트 단량체가 먼저 생성된 후, 단량체 양 말단에서 반응이 진행되어 빠르게 광경화 반응이 진행되었다. Dual curing systems of acrylates with thermo- and photo-reactions were studied to understand the effect of curing sequence on the curing reaction kinetics. A combined curing system that photochemical reaction with UV light followed by thermal cure was applied to acrylate monomer mixtures such as isocyanatoethyl acrylate (ICEA) and 2-hydroxyethyl methacrylate (HEMA). In such case, the polymer chain was formed by the first photo-curing and, then the functional groups participating in the urethane reaction were bound to the polymer chain, so that the urethane reaction by the thermal curing should be carried out at a higher temperature and the conversion rate was low. On the other hand, in the case of a dual curing process in which the photo-curing proceeded after the thermal curing, the urethane acrylate monomer was first formed by the thermal reaction, and then the faster photo-reaction proceeded at both ends of the monomer.

FTIR을 이용한 광반응 아크릴레이트 혼합물의 열경화 거동 연구

왕혁식(Hyuck Sik Wang),이승혁(Seung Hyuk Lee),부석형(Seok Hyeong Bu),송기국(Kigook Song) 한국고분자학회 2019 폴리머 Vol.43 No.1

열경화 반응을 할 수 있는 아크릴레이트 단량체들과 가교반응을 할 수 있는 diacrylate 올리고머의 혼합물에 대한 경화조건 변화에 따른 열경화 거동을 조사하였다. 열경화에 의한 우레탄 반응과 아크릴레이트의 광경화 반응을 time-resolved FTIR 실험으로 각 반응의 특성 IR 피크를 관찰하여 혼합물의 경화 속도와 경화율 변화를 측정하였다. 혼합물에 대하여 우레탄 열경화만 진행한 거동을 아크릴레이트 광경화 후 우레탄 열경화를 진행한 복합경화 경우와 비교하였다. Diacrylate 올리고머의 분자량과 아크릴레이트 단량체의 구조에 따른 우레탄 열경화 속도 변화를 조사하였다. Thermal curing behaviors of acrylate mixtures, which consist of photo-curable monomers and cross-linkable diacrylate oligomers, were studied under various curing conditions. The curing kinetics and curing degree of the mixtures were investigated using time-resolved FTIR spectroscopy by monitoring IR characteristic peaks of urethane thermal and acrylate photo-curing reactions. The thermal curing process of the mixture was compared with the dual curing process that is composed of urethane thermal-curing after acrylate photo-curing process. The effects of molecular weight of the diacrylate oligomer and of the acrylate monomer structures on the thermal curing kinetics were investigated.

광·열복합경화조건에 따른 폴리우레탄 아크릴레이트계 수지를 이용한 TPEE Mono-filament의 경화성 및 물성 연구

최주환,김아롱 한국섬유공학회 2019 한국섬유공학회지 Vol.56 No.5

Flexibility and hardness are very important for expressing color in textile materials using UV curing technology. In the preceding study, the lack of hardness resulted in dye migration challenges. In this study, we investigated the effects of an oligomer, hardener content ratios, and curing time on the UV and thermal dual curable resin on thermoplastic copolyester (TPEE) mono-filament while maintaining flexibility. We observed that an O-3 oligomer with 13,000 mPa·s viscosity, 11.25:4.65 ratio of HDI/Photoinitiator, photocuring time of 40 s, and thermal curing time of 5 min, showed the best formula conditions. By dual curable resin treatment of the TPEE filament, the tensile strength increased under all UV and heat treatments, but the elongation increased after 10 min of heat treatment. We also observed the surface and cross-section of the dual curing TPEE mono-filament.

온도에 따른 반응성 액정의 분자 배열 및 경화 반응 연구

이몽룡(Mongryong Lee),배진우(Jin Woo Bae),송기국(Kigook Song) 한국고분자학회 2015 폴리머 Vol.39 No.1

LC242와 같이 분자량이 큰 광반응성 액정 물질은 온도를 낮출 때 액정상에서 결정으로의 변화가 빠르지 못하여 액정분자를 재결정을 할 때는 충분한 시간이 필요하다. 액정 상태에서 분자의 배열 정도가 온도에 따라 영향받는 것을 알 수 있는데, 액정상의 LC242는 온도가 높아짐에 따라 액정 배열을 한 방향으로 계속 유지하고 있어도 온도에 따른 LC242 분자들의 움직임에 의하여 조금씩 배열이 달라져 복굴절의 변화를 가져오는 것을 알 수 있다. 광반응성 액정을 경화할 때 액정 상의 온도에서 광조사를 하면 고체상의 경우보다 반응 속도가 빠르고 경화도가 훨씬 많이 진행되는 것을 Photo-DSC 실험과 FTIR을 이용하여 정량적으로 분석하였다. Since a transition from liquid crystal to crystal state is slow for the large photo-reactive liquid crystal molecules, it needs a long time for recrystallization of LC242 molecules when lowering the temperature of the liquid crystal. Although liquid crystals usually align along one direction, the directions of individual liquid crystal molecules are little different from one another with increasing temperature, resulting in changes of birefringence of the liquid crystal films. When the photo-reactive liquid crystals are photo-cured, faster curing kinetics and much larger curing degrees are observed for the films cured at the liquid crystal phase.

Preliminary Study on the Effects of Out-of-Plane Deposition Angle on Product Characteristics of a UV Photo-Curing Process

장용훈(Yong-Hun Jang),안동규(Dong-Gyu Ahn),송재국(Jae-Guk Song),김동인(Dong-In Kim),신보성(Bo-Sung Shin) Korean Society for Precision Engineering 2017 한국정밀공학회지 Vol.34 No.1

The goal of this paper is to investigate the effects of out-of-plane deposition angle on product characteristics of a UV photo-curing process. Specimens are manufactured from a commercialized UV photo-curing machine, the NOBEL V1.0. The influence of the out-of-plane deposition angle of the specimen on surface characteristics, including morphology of the sloped surface, pick-to-pick distance of convex region, and roughness of the sloped surface, is examined via the observation of the sloped surface. In addition, the influence of the radius of curvature of the specimen on the surface roughness of the sloped surface is evaluated. The effects of the out-of-plane deposition angle on impact strength of specimens are investigated via Izod impact experiments. Finally, we discuss the influence of the out-of-plane deposition angle on failure characteristics of specimens for impact loads.

광경화성 아크릴 수지의 경화특성에 관한 연구

김성현(Sung Hyun Kim),장현석(Hyun Suk Chang),박선희(Sun Hee Park),송기국(Ki Gook Song) 한국고분자학회 2010 폴리머 Vol.34 No.5

광경화성 수지인 아크릴레이트의 경화 특성과 메카니즘에 대하여 Photo-DSC와 FTIR, Raman spectrometer를 이용하여 조사하였다. 아크릴레이트 종류, 관능기 수, 광 세기 등에 따른 경화 속도에 관한 정보는 시간에 따른 Photo-DSC curve에서 계산하였고, FTIR과 Raman을 이용하여 경화 반응의 전환율과 반응 메카니즘을 조사하였다. 광경화 반응에서 산소의 영향을 알아보기 위하여 아크릴레으트 수지와 thiol-ene 수지의 경화과정을 비교하였는데, 공기 중 산소가 아크릴레이트의 라디칼 반응에서 금지제로 작용하여 아크릴레이트 수치는 80% 이하의 전환율을 보인 반면 thiol-ene 수지는 산소가 반응에 영향을 미치지 않는 것을 알 수 있었다. The curing mechanism and characteristics of UV curable acrylate resins were studied using Photo-DSC, FTIR, and Raman spectroscopy, Effects of chemical structures of acrylate, numbers of functional group, and UV intensity on curing kinetics were investigated with Photo-DSC. FTIR and Raman spectroscopy has been used to understand curing mechanisms and reaction conversion. In order to investigate the effect of oxygen on the photo-curing reaction, the curing process was compared between the acrylate and thiol-ene resins. The reaction conversion was found to be less than 80% for acrylate resins. The photo-curing reaction of the acrylate resin could not proceed to the end because of oxygen which acts as a reaction inhibitor while the thiol-ene resin was hardly affected from oxygen during the curing process.

유착방지제의 응용을 위한 가시광 경화형 Carrageenan 유도체의 제조

김재원(Jae-Won Kim),김은혜(Eun-Hye Kim),한가득(Ga-Dug Han),노승현(Seung-Hyun Noh),김신웅(Shin-Woong Kim),최창순(Chang-sun Choi),나재운(Jae-woon Nah),김태연(Tae-Yeon Kim),손태일(Tae-Il Son) 한국고분자학회 2018 폴리머 Vol.42 No.3

유착방지제를 개발하기 위해 천연고분자인 K-Carrageenan을 이용하여 가시광 경화형 carrageenan 유도체(FCm-Carrageenan)를 제조하였다. Carrageenan은 생분해성, 생체적합성 등과 같은 특성을 가진 천연고분자이다. Riboflavin은 무독성, 생체적합성을 가지는 천연 광개시제이다. Riboflavin은 가시광 경화형 carrageenan 유도체에 광경화를 유도한다. ¹H NMR(proton nuclear magnetic resonance), GPC(gel permeation chromatography) 분석을 통하여 F-Cm-Carrageenan이 제조된 것을 확인하였으며 가시광 조사시간에 따른 광경화 정도를 판단하기 위해서 광경화실험을 진행하였다. 또한 유착방지제로 응용가능 여부를 판단하기 위해서 세포독성 실험, 유착방지 실험, 세포투과 실험을 진행하였다. 따라서 가시광 경화형 carrageenan 유도체는 새로운 형태의 유착방지제로서 응용될 수 있다고 사료된다. To develop anti-adhesion agent using photo-reaction, visible light curable carrageenan derivatives (F-Cm-Carrageenan) was prepared by using K-Carrageenan which is natural polymer. Carrageenan is a natural polymer having properties such as bio-degradability and bio-compatibility. Riboflavin is a non-toxic, bio-compatible natural photo-initiator. Riboflavin induces photo-crosslinking in visible light-curing carrageenan derivatives. ¹H NMR (proton nuclear magnetic resonance) and GPC (gel permeation chromatography) analysis were conducted to confirm that F-Cm-Carrageenan was prepared. Photo-curing test was conducted to determine the degree of photo-curing with visible light irradiation time. To evaluate the applicability as an anti-adhesion agent, cytotoxicity test, anti-adhesion test and cell penetration test were conducted. Therefore, it is considered that the visible light curable carrageenan derivatives can be applied as a new type of anti-adhesion agent.

Optimization of Photo-Curing Conditions of Silver Ink for Flexible Electronic Device Applications

김민하,김동욱,박상규,이재형 한국진공학회 2014 한국진공학회 학술발표회초록집 Vol.2014 No.8

Electrochemical characterization of photo-curable biopolymer electrolyte containing acrylated chitosan and methacrylated alginate

한아람,고용태,안규근,김현경 한국공업화학회 2015 한국공업화학회 연구논문 초록집 Vol.2015 No.0

Photo-curable biopolymer electrolyte comprising the blend of Acrylated Chitosan (AC) and Methacrylated Alginate (MA) as host polymer and LiClO4 in ethylene carbonate as liquid electrolyte is prepared by Ultra Violet (UV) curing technique. The conductivity has been investigated as a function of AC and MA polymer blend ratio with fixed content of liquid electrolyte at temperature range of 298.15K-358.15K using impedance spectroscopy. The maximum conductivity is found to be 3.222E- 03 S/cm at 298.15K for 5 to 5 ratio (AC/MA) concentration. The coordination of liquid electrolyte to the 5 to 5 ratio (AC/MA) concentration was shown to play an important role for physical state such as free volume. To verify this reason, emphasis is placed on the application of Arrhenius equation, the effects of activation energy, glass temperature and carrier density are taken into account.