World Journal of Organic Chemistry
ISSN (Print): 2372-2150 ISSN (Online): 2372-2169 Website: http://www.sciepub.com/journal/wjoc Editor-in-chief: Subrata Shaw
Open Access
Journal Browser
Go
World Journal of Organic Chemistry. 2019, 7(1), 5-13
DOI: 10.12691/wjoc-7-1-2
Open AccessArticle

Characterization and Synthesis of Functionalized Polysilalkylene Siloxane Monomers by Hydrosilylation Reaction

Ronald P. D’Amelia1, , Joseph Mancuso1, William F. Nirode1 and Sunaldeep Singh1

1Chemistry Department, Hofstra University, Hempstead, NY

Pub. Date: June 27, 2019

Cite this paper:
Ronald P. D’Amelia, Joseph Mancuso, William F. Nirode and Sunaldeep Singh. Characterization and Synthesis of Functionalized Polysilalkylene Siloxane Monomers by Hydrosilylation Reaction. World Journal of Organic Chemistry. 2019; 7(1):5-13. doi: 10.12691/wjoc-7-1-2

Abstract

The synthesis of novel polysilalkylene siloxane monomers is of great interest to industrial chemists owing to their polymeric analogues having extremely useful properties as elastomers, adhesives, fluids, resins, as well as additives to other commercial products. The current industrial process for creating silicone polymers is through hydrosilylation of dienes. This process can produce a wide variety of organosilicon compounds with vast range of uses. The objective of this experiment is to synthesize modified silicone monomers which can be readily hydrolyzed in the presence of water to form their corresponding polymeric analogues. In order to do this, terminal dienes were reacted with either dimethylchlorosilane or methylphenylchlorosilane in the presence of the Karstedt’s catalyst, the most commonly used hydrosilylation catalyst, in order to yield the modified siloxane monomers. We report on the methodologies used to determine the identity of the final products as well as the methods used to determine their properties.

Keywords:
polycarbosiloxanes organosilicon synthesis hydrosilylation fourier transform infrared spectroscopy nuclear magnetic resonance spectroscopy Karstedt’s catalyst

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

Figures

Figure of 5

References:

[1]  Kuhn, F; Nuyken, O; Putzien, S; “Functionalized Polysilalkelene Siloxanes (Polycarbosiloxanes) by Hydrosilylation- Catalysis and Synthesis”, Progress in Polymer Science, 688-713, September 2009.
 
[2]  Barnes, GH; Speier, JL; Webster, JA; “The Addition of Silicon Hydrides to Olefinic Double Bonds. II. The Use of Group VIII Metal Catalysts” J Am Chem Soc, 974-979, 1957.
 
[3]  Karstedt, BD; “Platinum-Siloxane Complexes as Hydrosilation Catalysts” US patents 3775452. Assigned to General Electric Co.; 1973.
 
[4]  Kogure, T; Ojima, I; “Hydrosilylation of Dienes, Acetylenes, and Carbonyls Catalyzed by Transition Metal Complexes” Rev Silicon Germanium Tin Lead Compd 1981.
 
[5]  Kopylova, LT; Lukevits, E; Pukhnarevich, VB; Voronkov, MG; “Prospects for Hydrosilylation” Lituana 1992.
 
[6]  Brook, MA; “Silicon in Organic, Organometallic and Polymer Chemistry” Weinheim, Germany: Wiley VCH; 2000.
 
[7]  Roy, A; “A Review of Recent Progress in Catalyzed Homogenous Hydrosilyation.” Adv Organomet Chem, 55-59, 2008.
 
[8]  Marciniec, B; “Hydrosilylation: A Comprehensive Review on Recent Advances” Adv Silicon Sci, 391-398, 2009.
 
[9]  Boutevin, B; Guida-Pietrasanta; “Polysilalkylene or Silarylene Siloxanes as Hybrid Silicones.” Adv Polym Sci, 179-187, 2005.
 
[10]  Sanchez, JC; Trogler, WC; “Hydrosilylation of Diynes as Route to Functional Polymers Delocalized Through Silicon” Macromol Chem Phys, 1527-1540, 2008.
 
[11]  Abdellah, L; Boutevin, B; Youssef, B; “Synthesis and Applications of Photocrosslinkable Polysiloxanes” Progr Org Coat, 201-236, 1994.
 
[12]  Maxson, MT; Norris, AW, Owen, MJ; “Fluorosilicones In: Scheiers J, editor. Modern Fluoropolymers.” Wiley, 359-372, 1997.
 
[13]  Roessing, M; “Additives in Adhesive Formulations: Wetting Agents- Boon or Bane?” Adhaesion Kleben Dichten, 22-27, 2009.
 
[14]  Almeida, DF; Dias, TC; Lin, S; “Silicone Copolymers and Elastomers Derived From Natural Oils” Dow Corning Corporation, 2008.
 
[15]  Madec, J; Marechal, EJ; “A New Route for Silicon-Containing Block Copolymer Synthesis” Polym Prepr, 814-815, 1993.
 
[16]  Hocker, H; Riedel, J-H; “Preparation and Characterization of Polymers with Pending UV-absorber Groups I. Polymers Based on Poly(dimethylsiloxane).” J Appl Polym Sci, 573-579, 1994.
 
[17]  Xie, Y; Xu, X; Zhang, C; “Recent Development of Organosilicon Quaternary Ammonium Salt as Antimicrobial Agent” Huagong Jishu Yu Kaifa, 25-28, 2008.
 
[18]  Herrwerth, S; Koenig, F; Maurer, T; Stadtmueller, S; “New Phosphated organopolysiloxane Derivatives and Their Use for Improving The Water-Resistance of Leather and Textiles” German Patent DE 102006047898. Assigned to Evonik Goldschmidt GmbH, 2008.
 
[19]  Bender, W; Krumpfer, A; Krumpfer, J; Longenberger, T; Ryan, K; “The Art of Silicones: Bringing Siloxane Chemistry to the Undergraduate Curriculum.” J Chem Educ. 1682-1690, 2017.
 
[20]  Wacker “Silicones, Compounds and Properties” 2011.