光点击化学修饰石油树脂研究

doi:10.7517/j.issn.1674-0475.2016.04.380

影像科学与光化学 ›› 2016, Vol. 34 ›› Issue (4): 380-387.DOI: 10.7517/j.issn.1674-0475.2016.04.380

• 应用与发展 • 上一篇

光点击化学修饰石油树脂研究

扶浩¹, 杨建文², 刘晓暄¹

1. 广东工业大学材料与能源学院高分子材料与工程系, 广东广州 510006;
2. 中山大学材料科学与工程学院, 广东广州 510275

收稿日期:2016-02-21 修回日期:2016-04-11 出版日期:2016-07-15 发布日期:2016-07-15
通讯作者: 刘晓暄
基金资助:
国家自然科学基金项目(21374135)资助

Modification of Petroleum Resins by Photo-induced Click Chemistry

FU Hao¹, YANG Jianwen², LIU Xiaoxuan¹

1. Department of Polymeric Materials and Engineering, School of Materials and Energy, Guangdong University of Technology, Guangzhou 510006, Guangdong, P. R.China;
2. School of Materials Science and Engineering, Sun Yat-sen University, Guangzhou 510275, Guangdong, P. R.China

Received:2016-02-21 Revised:2016-04-11 Online:2016-07-15 Published:2016-07-15

摘要/Abstract

摘要：

为改善传统石油树脂改性方法能耗高、效率低等缺陷,本文应用点击化学,在常温下,以甲苯为溶剂,以Darocur1173为光引发剂,在UV-LED灯辐照下,通过3-巯基丙酸与DCPD石油树脂发生巯基-烯加成反应,制备的产物命名为DCPD-COOH。以三苯基膦为催化剂,用甲基丙烯酸缩水甘油酯(GMA)与DCPD-COOH反应,制备了可光固化的丙烯酸酯石油树脂,命名为DCPD-A。固化漆膜的设计配方:DCPD-A(50份)、活性稀释剂甲基丙烯酸羟乙酯(HEMA,50份),光引发剂Darocur1173(5份)。在该配方下制得的固化漆膜其附着力达到0级,铅笔硬度为2H。制备的DCPD-A与极性溶剂或者极性树脂的相容性较好,可应用于光固化涂料和光固化油墨等领域。

关键词: DCPD石油树脂, 巯基/烯点击化学, UV固化, 光化学改性

Abstract:

The traditional modification methods of the petroleum resins are always linked with high energy consumption and low efficiency, To overcome this drawbacks, the photo-induced click chemistry of 3-mercaptopropionic acid was utilized to modify a type of petroleum resin, DCPD, in this work. The reaction was carried out in toluene solution and at room temperature, using Darocur1173 as photoinitiator and a UV-LED lamp as light source. The resulting product is named as DCPD-COOH. In the presence of triphenyl phosphine, DCPD-COOH was allowed to react with glycidyl methacrylate (GMA)to transform to an acrylate petroleum resin, named as DCPD-A. Upon UV irradiation of a mixture of 50 portion of DCPD-A, 50 portion of a reactive diluent 2-hydroxyethyl methacrylate(HEMA), and 5 portion of Darocur1173, a UV-cured thin film with 0 level of adhesion and 2H of pencil hardness was prepared. The modified petroleum resin has good compatibility with polar solvent and resins, applicable as UV-curing coatings and inks.

Key words: DCPD petroleum resin, thiol-ene click chemistry, UV-curing, photo-induced modification

扶浩, 杨建文, 刘晓暄. 光点击化学修饰石油树脂研究[J]. 影像科学与光化学, 2016, 34(4): 380-387.

FU Hao, YANG Jianwen, LIU Xiaoxuan. Modification of Petroleum Resins by Photo-induced Click Chemistry[J]. Imaging Science and Photochemistry, 2016, 34(4): 380-387.

参考文献

[1] 王军.石油树脂生产及应用进展[J].化学与粘合,2003,(5):253-255. Wang J. Progress in production and application of petroleum resins[J]. Chemistry and Adhesion, 2003, (5):253-255.
[2] 林洁,蒋山,贺民,纪敏,张耀亨,张霖,蔡天锡.C5石油树脂的研究及应用[J].合成树脂及塑料,2006, 23(2):81-84. Lin J,Jiang S,He M,Ji M,Zhang L, Cai T X. Research and application of C5 petroleum resin[J]. China Synthetic Resin and Plastic, 2006, 23(2):81-84.
[3] 付宗燕.C9石油树脂生产工艺及其应用[J]. 石化技术, 2006, 13(1):49-53. Fu Z Y.Application and production of C9 petroleum resin[J]. Petrochemical Industry Technology, 2006, 13(1):49-53.
[4] 杜新胜,陈世龙,李亮.C5/C9共聚石油树脂的研究进展[J].粘接,2013,(6):67-69. Du X S,Chen S L,Li L. Research and development of C5/C9 copolymerized petroleum resins[J]. Adhesion, 2013,(6):67-69.
[5] 杜新胜,徐海燕.双环戊二烯石油树脂的研究进展[J].上海涂料,2013,51(3):31-34. Du X S,Xu H Y.Research and development of dicyclopentadiene petroleum resin[J]. Shanghai Coating, 2013, 51(3):31-34.
[6] 杜新胜,张荣.C5石油树脂在涂料中的应用[J].上海涂料,2013,51(12):27-30. Du X S,Zhang R. The application of C5 petroleum resin in coatings[J]. Shanghai Coating, 2013, 51(12):27-30.
[7] Nagayama T,Nakata S.Resin for printing ink composition, printing ink composition and method for producing resin for printing ink composition. Japan patent,189593.2013-09-26.
[8] Yamane H.Preparation process of petroleum resin and hydrogenated petroleum resin. Japan patent,189764.2004-07-08.
[9] Mizui,Kinya T,Masami I,Tadao.Hydrocarbon resin and modified hydrocarbon resin product thereof.US patent, 4533700. 1985-08-06.
[10] Hattori A. Petroleum resin acrylate and method for producing the same.Japan patent,024898, 2008-02-07.
[11] Lowe A B.Thiol-ene "click" reactions and recent applications in polymer and materials synthesis[J]. Polymer Chemistry, 2010, (1):17-36.
[12] 杨建文,曾兆华,陈用烈.光固化涂料及应用[M].北京:化学工业出版社,2005. Yang J W, Zeng Z H, Chen Y L. Photocuring Coatings and Its Application[M]. Beijing: Chemical Industry Press, 2005.
[13] Pogantsch A, Rentenberger S, Langer G, Keplinger J, Kern W, Zojer E. Tuning the electroluminescence color in polymer light-emitting devices using the thiol-ene photoreaction[J]. Advanced Functional Materials, 2005, 15(3), 403-409.
[14] Lotti L, Coiai S, Ciardelli F, Galimberti M, Passaglia E. Thiol-ene radical addition of L-cysteine derivatives to low molecular weight polybutadiene[J]. Macromolecular Chemistry and Physics, 2009, 210(18), 1471-1483.
[15] Hong M, Liu S R, Li B X, Li Y S. Application of thiol-ene click chemistry to preparation of functional polyethylene with high molecular weight and high polar group content: influence of thiol structure and vinyl type on reactivity[J]. Journal of Polymer Science Part A: Polymer Chemistry, 2012,50(12) : 2499-2506.
[16] 彭高聪,路宝田,向绍基,谢国煌.浅色度C9石油树脂的研究Ⅲ核磁共振和红外光谱表征[J].涂料工业,1998,(1):39-42. Peng G C, Lu B T, Xiang S J, Xie G H. Study on the light color petroleum resin part Ⅲ NMR and IR characterization[J]. Paint and Coatings Industry, 1998, (1): 39-42.

光点击化学修饰石油树脂研究

Modification of Petroleum Resins by Photo-induced Click Chemistry

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 8

编辑推荐

Metrics

本文评价

[1]	吴保林, 黄笔武, 杜志鹏, 雍涛, 韩琳琳. 纳米SiO₂改性苯基缩水甘油醚丙烯酸酯的紫外光固化性能研究[J]. 影像科学与光化学, 2019, 37(4): 304-314.
[2]	蒋乙峰. 生物基UV固化预聚物制备及性能研究[J]. 影像科学与光化学, 2019, 37(3): 241-248.
[3]	秦长喜, 牛娟妮, 高超. 纳米金属氧化物隔热窗膜及性能研究[J]. 影像科学与光化学, 2017, 35(1): 80-87.
[4]	蒋辉, 王德海, 胡祥太, 陈敏. POP-290阻燃剂对丙烯酸酯光固化涂料的影响[J]. 影像科学与光化学, 2010, 28(3): 209-216.
[5]	刘慧, 刘炼, 张春庆. 新型紫外光固化粘接性单体的合成与应用研究[J]. 影像科学与光化学, 2006, 24(3): 218-224.
[6]	王艳梅, 魏杰. 超支化树脂改性UV固化粉末涂料[J]. 影像科学与光化学, 2003, 21(2): 126-131.
[7]	李妙贞, 覃耀进, 常志英, 王尔鑑. AM/AMPS共聚物光化学改性[J]. 影像科学与光化学, 2002, 20(4): 247-252.
[8]	储九荣, 温序铭, 徐传骧, 吴志勇. UV-光固化光纤涂料的研制[J]. 影像科学与光化学, 2000, 18(3): 271-276.