Multifunctional coupling agents. II. Chain extension and terminal group modification of polyamides

2004 ◽  
Vol 94 (5) ◽  
pp. 2170-2177 ◽  
Author(s):  
L. Jakisch ◽  
H. Komber ◽  
R. Wursche ◽  
F. Böhme
2016 ◽  
Vol 658 ◽  
pp. 270-275 ◽  
Author(s):  
Bin Zheng ◽  
Lian Li Wang ◽  
Lifei Du ◽  
Kuo-Wei Huang ◽  
Huiling Du

2006 ◽  
Vol 426 (4-6) ◽  
pp. 361-364 ◽  
Author(s):  
Takeo Miyake ◽  
Takashi Tanii ◽  
Koichi Kato ◽  
Takumi Hosaka ◽  
Yuzo Kanari ◽  
...  

2020 ◽  
Vol 253 ◽  
pp. 117525 ◽  
Author(s):  
Xiaofang Feng ◽  
Zongxue Yu ◽  
Runxuan Long ◽  
Xiuhui Li ◽  
Liangyan Shao ◽  
...  

2019 ◽  
Vol 171 ◽  
pp. 107653
Author(s):  
Yi Li ◽  
Yuancong Zhong ◽  
Shuguang Wen ◽  
Yong Zhang ◽  
Renqiang Yang

2020 ◽  
Vol 6 (2) ◽  
pp. 865-878 ◽  
Author(s):  
Cunyang Wang ◽  
Guangxiu Cao ◽  
Tianxiao Zhao ◽  
Xiumei Wang ◽  
Xufeng Niu ◽  
...  

2008 ◽  
Vol 47 (5) ◽  
pp. 986-999 ◽  
Author(s):  
Chengxiang Lu ◽  
Li Chen ◽  
Ronggen Ye ◽  
Xufu Cai

2021 ◽  
Vol 17 ◽  
pp. 1440-1446
Author(s):  
Memory Zimuwandeyi ◽  
Manuel A Fernandes ◽  
Amanda L Rousseau ◽  
Moira L Bode

Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the first total synthesis of the enantiomer of pavettamine, ent-pavettamine. The symmetrical structure of the molecule allows for the synthesis of a common C5 fragment that can be divergently transformed into two synthons for later convergent coupling to furnish the target carbon framework. Based on the success of the protocol we employed for the synthesis of the naturally occurring pavettamine, (S)-malic acid was again the starting material of choice for the synthesis of the two individual C5 fragments, with strategic differences in terminal-group manipulation allowing for the synthesis of ent-pavettamine rather than pavettamine. Chain extension and stereoselective ketone reduction were achieved using the (R)-methyl p-tolyl sulfoxide chiral auxiliary to give the desired 1,3-syn-diol C5 unit. A protecting-group strategy was also developed for the orthogonal protection of the alcohol and amine functional groups as they were unveiled. The functionalized C5 fragments were coupled via reductive amination revealing the C10 carbon backbone. Deprotection of the alcohol and amine functional groups successfully provided ent-pavettamine as a TFA salt.


2010 ◽  
Vol 38 (1) ◽  
pp. 80-98 ◽  
Author(s):  
M. Gerster ◽  
C. Fagouri ◽  
E. Peregi

Abstract One challenge facing green tire technology is to achieve good silica hydrophobation/dispersion within the polymer matrix without a detrimental increase in the rubber compound’s viscosity during compounding. This phenomenon is well known to be induced by premature and unwanted coupling and/or crosslinking of the traditional coupling agents. The current state-of-the-art polysulfides silanes, bis(3-triethoxysilylpropyl)tetrasulfide and to a lesser extent bis(3-triethoxysilylpropyl)disulfide (“Product Application—VP Si 75/VP X 75-S in the Rubber Industry,” Degussa Hüls Report No. PA 723.1E), need to be carefully incorporated with careful temperature control during the rubber compounding to prevent this “scorchy” behavior. This paper will present novel monofunctional silanes which are suited for preparing highly silica-loaded rubber compounds of superior processability, while applying fewer mixing passes, thereby reducing mixing times which can lead to improved productivity and cost savings. Additionally, these safer coupling agents can be processed at higher temperatures which can, again, lead to reduced mixing time and better ethanol removal thereby improving the tire’s physical properties and reducing the volatile organic compounds generated during the tire’s use. The rubber compounds produced using these monofunctional silanes are characterized by lower Mooney viscosity and improved processability. Advantageously, within these novel chemical classes of coupling agents, selective functionalization of the silanes allows production of tailor-made coupling agents which can respond to the specific requirements of the tire industry (Vilgis, T. A. and Heinrich, G., “Die Physic des Autoreifens,” Physikalische Blätter, Vol. 57, 2001, pp. 1–7).


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