Synthesis and Application of a Novel Colorless DAR Coupler

doi:10.7517/j.issn.1674-0475.2005.02.151

Abstract

Abstract: With [5-mercapto-(1, 3, 4) thiadiazol-2-yl-thio]-acetic acid adopted as the adsorption group and trifluoro-acetic acid 2-( 4-amino-phenyl )-hydrazide as the strengthen groups respectively, a novel colorless DAR (A) coupler was synthesized from N,N’-bis-(2-chloro-5-n-dodecyloxy-carbonyl) phenylmalonamide. The intermediates and the target compound were characterized and confirmed by means of IR, MS,¹HNMR. It contributed much to the increase of the photosensitivity of the color negative film and without changing the absorption spectrum of the main coupler developed.

Key words: DAR coupler, adsorption group, strengthen group, synthesis, application

CLC Number:

TQ57

YU Kai, LIANG Xiao-cong, ZHANG Da-de. Synthesis and Application of a Novel Colorless DAR Coupler[J]. Imaging Science and Photochemistry, 2005, 23(2): 151-157.

References

[1] Matejec Reinhart, Becker Manfred, Odenwaelder Heinrich, Metz Hans Joerg. Color photographic recording materials[P].DE patent,3 605 713, 1987-08-27.
[2] Bruce W Hotten. Phenylamides of organoamine ployacetic acide as anti-oxidants greasea[P].US patent, 3 214 377, 1965-10-26.
[3] 朱正华,胡倩琪,徐秀珍,姚祖光. 二当量成色剂的近代发展 [J]. 感光科学与光化学,1988, 1:38-51.Zhu Z H, Hu Q Q, Xu X Z, Yao Z G. Recent progress of 2-equivalent couplers [J].Photographic Science and Photochemistry, 1988, 1: 38-51.
[4] 刘玉婷,等.DAR成色剂研究进展 [J]. 感光科学与光化学,2004, 22 (2):126-136.Liu Y T, et al. Progress of research work on DAR coupler[J].Photographic Science and Photochemistry, 2004, 22 (2): 126-136.
[5] 于凯, 等. 无色功能性成色剂[J]. 信息记录材料,2003, 4:33-38.Yu K, et al. Colorless function couplers[J]. Information Recording Materials, 2003, 4: 33-38.
[6] 郭奇珍,陈馨娥. 2,5-二巯基-1,3,4-硫二氮茂衍生物的合成 [J].化学学报,1963. 29 (1):62-63.Guo Q Z, Chen Q E. Synthesis of 2,5-dithiol-1,3,4-thiadiazole and derivatives [J]. Acta Chimica Sinica, 1963, 29 (1): 62-63.
[7] 刘玉婷,等. DAR黄成色剂的合成 [J]. 感光科学与光化学,2004,22 (1):28-32.Liu Y T,et al. Synthesis of DAR yellow coupler [J]. Photographic Science and Photochemistry, 2004,22 (1):28-32.
[8] Murase Kiyoshi,Mase Toshiyasu, Hara Hiromu. Thiadiazole compounds as antagonists of SRS-A[P].US patent,4 855 310, 1989-08-08.
[9] Kobayashi Hidetoshi, Toriuchi Masaharu. Silver halide color photographic light-sensitive material[P].US patent, 4 724 199, 1988-02-09.
[10] Mifune Hiroyuki, Hirano Shigeo, Akimura Yoshitaka. Silver halide photographic light-sensitive materials[P].US patent,4 323 643, 1982-04-06.
[11] Kobayashi Hidetoshi, Mihayashi Keiji. Silver halide photographic light-sensitive material[P]. EP, 0 147 765, 1985-07-10.
[12] Kobayashi Hidetoshi, Takahashi Toshirou, Hirano Shigeo, Hirosa Takeshi, Adachi Keiichi. Silver halide photographic light-sensitive materials[P]. US patent,4 390 618, 1983-06-28.

[1]	ZHU Tao, ZHANG Yan, DONG Lulu, GUO Pengyue, YANG Dongzhi. Biomimetic Synthesis of Au QDs and the Application of Glucose Detection in Serum [J]. Imaging Science and Photochemistry, 2020, 38(6): 941-949.
[2]	TAO Pingfang, FENG Yuqin, ZHOU Neng, QIN Liqin, ZHANG Pei. Hydrothermal Synthesis of α-NaYF₄: Ce³⁺/Tb³⁺ Nanospheres with High Fluorescence Properties [J]. Imaging Science and Photochemistry, 2018, 36(2): 161-170.
[3]	JI Haixia, DONG Lulu, DU Yan, YAO Xinyue, YANG Dongzhi. Biomimetic Synthesis of CdS Quantum Dots in Living Cancer Cells [J]. Imaging Science and Photochemistry, 2018, 36(1): 57-63.
[4]	ZENG Ze, ZHONG Rong, ZHANG Chunhui, XIE Gang. Synthesis and Properties of Phenylglyoxylic Acid Ester/2959 Photoinitiator [J]. Imaging Science and Photochemistry, 2017, 35(6): 808-815.
[5]	DENG Yafeng, ZHOU Yihua, QIAN Jun, LUO Yan, WU Lihui. Preparation and Application of Carbon Quantum Dots Based on Up Conversion Photoluminescence [J]. Imaging Science and Photochemistry, 2017, 35(6): 884-893.
[6]	WANG Hua. Chemical and Photochemical Synthesis of Thiophene-based Helicenes [J]. Imaging Science and Photochemistry, 2017, 35(5): 603-613.
[7]	ZHANG Qingbao, LIU Qiang. Applications of Visible-light-driven Aerobic Oxidation in Organic Synthesis [J]. Imaging Science and Photochemistry, 2017, 35(5): 614-625.
[8]	CAO Yitao, WU Lizhu, TONG Zhenhe(TUNG Chenho), ZHANG Tierui. Photochemical Synthesis of Inorganic Nanomaterials [J]. Imaging Science and Photochemistry, 2017, 35(5): 642-648.
[9]	GUI Mengxi, YU Yang, ZHU Chengyi, LIU Hongfang, WANG Feng. Advances on Molecular Systems for Photocatalytic CO₂ Reduction Based on Cobalt Complexes as Catalysts [J]. Imaging Science and Photochemistry, 2017, 35(5): 649-657.
[10]	HUA Xin, BAO Chunyan, LIN Qiuning, ZHU Linyong. Construction of Photo-controlled Hydrogels and Their Applications in Biomedical Fields [J]. Imaging Science and Photochemistry, 2017, 35(4): 379-395.
[11]	LEI Yuan, ZHANG Sai, GAO Jun. Synthesis,Structure and Photochromic Properties of N-ethyl-9'-n Bromobutoxy Spirooxazine and Its Modified PMMA [J]. Imaging Science and Photochemistry, 2016, 34(6): 526-533.
[12]	XIA Jing, WANG Lei, ZHU Dandan, LI Xuanze, MENG Xiangmin. Research Advancement of Preparation of SnS₂ Nanosheets and Device Applications [J]. Imaging Science and Photochemistry, 2016, 34(3): 219-232.
[13]	JIANG Wei, WU Xiang. Hydrothermal Synthesis and Photocatalytic Properties of ZnS Microflowers [J]. Imaging Science and Photochemistry, 2016, 34(3): 252-256.
[14]	KONG Xianghao, LI Xiang, CHEN Zhuoyi, YANG Hua, LI Guo. Continuous Observation Oriented Application Mode Design and Analysis for Geostationary-orbit High-resolution Optical Imaging Satellites [J]. Imaging Science and Photochemistry, 2016, 34(1): 43-50.
[15]	YANG Ke, ZHANG Yan, XU Jianhua. The Application of Electron Transfer Photo-oxidation Reaction in Organic Synthesis [J]. Imaging Science and Photochemistry, 2014, 32(5): 433-446.