含硫聚氨酯是一种新型高档镜片材料,具有折射率高、色散系数低、质量轻、耐磨性能和耐冲击性能高的优点。分类总结了合成含硫聚氨酯所需单体异硫氰酸酯和硫醇化合物的合成方法,并概述了国内外含硫聚氨酯的制备方法和研究进展,展望了其发展方向。
Polyurethane containing-sulfur is a new type of high-quality lens material,which has high refractive index,low dispersion coefficient,light and the advantage of wear resistance and impact resistance performance.The synthesis of the monomers of isothisocyanate and mercaptan,and reviewed the research progress on sulfur-containing polyurethane.The development also was prospected.
[1] 高长有.含硫高折光指数光学塑料的分子设计[J].材料研究学报,1999,13(1):9-16.
[2] Goddard S J.Novel 2-aryl-2,3,5,6,7,8-hexahydro-3-thioxoimidazo-[1,5-a-]pyridin-1(BaH)-ones as herbicides:US4138242[P].1979-02-06.
[3] Molina P,Alajarin M,Arques A.Convenient improved syntheses of isocyanates or isothiocyanates from amines[J].Synthesis,1982:596-597.
[4] Karlfried D,Engelbert K.Sulfonyl isothiocyanates and a process for their production:US3346590[P].1967-10-10.
[5] Ogata M,Watanabe Y,Tawara K.Phenyl isothiocyanate derivatives and their production:US4248869[P].1981-02-03.
[6] Yamaguchi M,Ohi H.Dithiocarbamic acid salt,process for production thereof,and process for production of isothiocyanate using said dithiocarbamic acid salt:US5274166[P].1993-12-28.
[7] 黄瑞秋,王惠林,周嘉.有机中间体制备[M].北京:化学工业出版社,1997,54,58.
[8] 李在国.有机中间体制备[M].北京:化学工业出版社,2001,64,72.
[9] Wong R,Dolman S J.Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts[J].Journal of Organic Chemistry,2007,72(10):3969-3971.
[10] 杜晓华,许响生,傅幼锋,等.非硫光气法合成一些难合成的芳基异硫氰酸酯[J].农药,2004,45(2):78-79.
[11] 吕延文,余志群.芳磺酰异硫氰酸酯的合成工艺研究[J].化学世界,2009,50(12):731-733.
[12] 杨锦宗.工业有机合成基础[M].北京:中国石化出版社,1997,526.
[13] Wang S S,Magliocco L G.Process of alkoxy isothiocyanate preparation:US5194673[P].1993-03-16.
[14] Rothenberg A S,Magliocco L G.Process for the beneficiation of sulfide minerals:US7011216[P].2006-03-14.
[15] 库尔卡尼S·V,·德塞V·C.在二烷基芳胺存在下制备羰基异硫氰酸酯及其衍生物的方法:CN12777190A[P].2000-06-09.
[16] Lewellyn M E.Process for the preparation of N-allyl-O-alkyl thionocarbamates:US4482500[P].1984-11-13.
[17] 栾和林,姚文,武荣成.一种硫代氨基甲酸酯类化合物的制备方法:CN1153774A[P].1997-07-09.
[18] Iranpoor N,Firouzabadi H,Akhlaghinia B,et al.Conversion of alcohols,thiols,carboxylic acids,trimethylsilyl ethers,and carboxylates to thiocyanates with triphenylphosphine/diethylazodicarboxylate/NH4SCN[J].ChemInForm,2004(1):92-96.
[19] Iranpoor N,Firouzabadi H,Nowrouzi N.Preparation of thiocyanates and isothiocyanates from alcohols,thiols,trimethylsilyl-,and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone(DDQ)/n-Bu4NSCN system[J].Tetrahedron,2006,62(23):5498-5501.
[20] 武荣成,咸建良.硫代氨基甲酸酯的制备方法:CN101367755A[P].2009-02-18.
[21] 苏海兰.乙烯-硫化氢催化加成合成乙硫醇[D].天津:天津大学,2007.
[22] Whtison B L,Boots H L.Contro system for multiple ultraviolet reaction:US3288679[P].1996-11-29.
[23] Tsao M W,Hoffmann C L,Rabolt J F,et al.Studies of molecular orientation and order in self-assembled semifluorinated,n-alkanethiols:single and dual component mixtures[J].Langmuir,1997,13(16):4317-4322.
[24] 徐克勋.精细有机化工原料及中间体手册[M].北京:化学工业出版,1998,497-498.
[25] 胡昆,祁燕杰,任杰,等.萝卜硫素衍生物及其制备方法和用途:CN102775336A[P].2012-11-14.
[26] 冈崎光树,金村芳信,永田辉幸.多元硫醇及其制法和由其制得的含硫的聚氨酯基树脂及制法和透镜:CN1215737A[P].1999-05-05.
[27] 汪山献松,陈国贵,林晓华,等.四硫基多元硫醇制法和采用该硫醇制备聚氨酯基树脂镜片的方法:CN101684085A[P].2010-03-31.
[28] Kanemura Y,Imai M,Sasagawa K,et al.High-refractivity plastic lens resin formed by reacting at least one polyisocyanate with at least one polythiol:US4775733[P].1988-10-04.
[29] 叶耘峰,李乐,唐果东,等.高折射率透明聚氨酯弹性体的制备及性能研究[J].聚氨酯工业,2018,33(6):9-11.
[30] 王明华,纪立军,郑莹,等.一种聚氨酯型高折射含硫光学树脂单体及其制备方法:CN105777596A[P].2017-12-12.
[31] 大久保毅,高松健.硫醇化合物、制备该化合物的方法和含该化合物的光学产品:CN1421444A[P].2003-06-04.
[32] Jang D G,Roh S G,Kim J H.Method for preparing thioepoxy-based optical material and polymerizable composition thereof:US9372281[P].2016-06-21.
[33] Teruyuki N,Koju O,Tohru M.Lens comprising a resin having a large refractive index and process for praring the lens:EP0351073[P].1990-01-17.