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Erschienen in: Polymer Bulletin 6/2020

26.07.2019 | Original Paper

Reaction of “unreactive” silicone: synthesis of long-chain alkyl fluorosilicone via a simple siloxane equilibration process

verfasst von: Yongjie Zhang, Mingshuai Fan, Xiaopei Li

Erschienen in: Polymer Bulletin | Ausgabe 6/2020

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Abstract

Long-chain alkyl silicone is a type of modified silicones that finds potential applications in various areas. Long-chain alkyl fluorosilicone (LCAFS) can be considered as a modified long-chain alkyl silicone as it synergistically combines the properties of long-chain alkyl silicone and novel fluorosilicone. As far as we know, reports on the synthesis of LCAFS are rare. In this report, a facile method to synthesize LCAFS was explored. It was found that silicone bearing novel C30-45 alkyls and trifluoropropyl pendent groups, namely (C30-45 alkyl) methylsiloxane/trifluoropropylmethylsiloxane copolymer (TF-AMS), could be synthesized via a simple siloxane equilibration process between silanol-terminated polytrifluoropropylmethylsiloxane and (C30-45 alkyl)methyl silicone, a commercially available silicone that is generally considered as unreactive. The chemical structure of TF-AMS was characterized unambiguously by FTIR, NMR, GPC and DSC. The thermal stabilities of TF-AMS were investigated by TGA. Based on our experimental results, a plausible mechanism for the synthesis of TF-AMS was proposed.

Graphic abstract

A novel long-chain alkyl fluorosilicone was synthesized via a simple yet efficient siloxane equilibration process.

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Literatur
1.
Zurück zum Zitat An Q, Wang K, Jia Y (2011) Film morphology, orientation and performance of dodecyl/carboxyl functional polysiloxane on cotton substrates. Appl Surf Sci 257:4569CrossRef An Q, Wang K, Jia Y (2011) Film morphology, orientation and performance of dodecyl/carboxyl functional polysiloxane on cotton substrates. Appl Surf Sci 257:4569CrossRef
2.
Zurück zum Zitat Ji C, Li F, Yun Z (2018) Synthesis of alkyl polymethylsiloxane (APMS) by condensation reaction and study of properties as lubricants. J Macromol Sci Part A Pure Appl Chem 55:332CrossRef Ji C, Li F, Yun Z (2018) Synthesis of alkyl polymethylsiloxane (APMS) by condensation reaction and study of properties as lubricants. J Macromol Sci Part A Pure Appl Chem 55:332CrossRef
3.
Zurück zum Zitat Cheng C, Powell KT, Khoshdel E, Wooley KL (2007) Polydimethylsiloxane- (PDMS-) grafted fluorocopolymers by a “grafting through” strategy based on atom transfer radical (Co)polymerization. Macromolecules 40:7195CrossRef Cheng C, Powell KT, Khoshdel E, Wooley KL (2007) Polydimethylsiloxane- (PDMS-) grafted fluorocopolymers by a “grafting through” strategy based on atom transfer radical (Co)polymerization. Macromolecules 40:7195CrossRef
4.
Zurück zum Zitat Wolf MP, Salieb-Beugelaar GB, Hunziker P (2018) PDMS with designer functionalities—properties, modifications strategies, and applications. Prog Polym Sci 83:97CrossRef Wolf MP, Salieb-Beugelaar GB, Hunziker P (2018) PDMS with designer functionalities—properties, modifications strategies, and applications. Prog Polym Sci 83:97CrossRef
5.
Zurück zum Zitat Mark JE (2004) Some interesting things about polysiloxanes. Acc Chem Res 37:946CrossRef Mark JE (2004) Some interesting things about polysiloxanes. Acc Chem Res 37:946CrossRef
6.
Zurück zum Zitat Kobayashi H, Owen MJ (1993) Surface tension of liquid polysiloxanes having fluorinated alkyl side-chains. Die Makromolekulare Chemie 194:1785CrossRef Kobayashi H, Owen MJ (1993) Surface tension of liquid polysiloxanes having fluorinated alkyl side-chains. Die Makromolekulare Chemie 194:1785CrossRef
7.
Zurück zum Zitat Tolinski M (2015) 12—processing aids for extrusion. In: Tolinski M (ed) Additives for polyolefins, 2nd edn. William Andrew Publishing, Oxford, p 135CrossRef Tolinski M (2015) 12—processing aids for extrusion. In: Tolinski M (ed) Additives for polyolefins, 2nd edn. William Andrew Publishing, Oxford, p 135CrossRef
8.
Zurück zum Zitat Jin Z, Fan H, Li B-G, Zhu S (2016) Evaluation of octyltetramethyldisiloxane-containing ethylene copolymers as composite lubricant for high-density polyethylene. Macromol Mater Eng 301:1494CrossRef Jin Z, Fan H, Li B-G, Zhu S (2016) Evaluation of octyltetramethyldisiloxane-containing ethylene copolymers as composite lubricant for high-density polyethylene. Macromol Mater Eng 301:1494CrossRef
9.
Zurück zum Zitat Zhang M-M, Liu S-W, Zhang Y, Chen L-H, Chi Z-G, Xu J-R (2013) Synthesis and characterization of a novel macromolecular surface modifier for polyethylene. Chin J Polym Sci 31:894CrossRef Zhang M-M, Liu S-W, Zhang Y, Chen L-H, Chi Z-G, Xu J-R (2013) Synthesis and characterization of a novel macromolecular surface modifier for polyethylene. Chin J Polym Sci 31:894CrossRef
10.
Zurück zum Zitat Chen HJ, Shi XH, Zhu YF, Zhang Y, Xu JR (2008) Enrichment of poly(methyl methacrylate) and its graft copolymer of polybutadiene on the surface of polypropylene blends. Appl Surf Sci 254:1763CrossRef Chen HJ, Shi XH, Zhu YF, Zhang Y, Xu JR (2008) Enrichment of poly(methyl methacrylate) and its graft copolymer of polybutadiene on the surface of polypropylene blends. Appl Surf Sci 254:1763CrossRef
11.
Zurück zum Zitat Chen HJ, Shi XH, Zhu YF, Zhang Y, Xu JR (2008) Polypropylene surface modification by entrapment of polypropylene-graft-poly(butyl methacrylate). Appl Surf Sci 254:2521CrossRef Chen HJ, Shi XH, Zhu YF, Zhang Y, Xu JR (2008) Polypropylene surface modification by entrapment of polypropylene-graft-poly(butyl methacrylate). Appl Surf Sci 254:2521CrossRef
12.
Zurück zum Zitat Shin B, Lee KR, Moon MW, Kim HY (1817) Extreme water repellency of nanostructured low-surface-energy non-woven fabrics. Soft Matter 2012:8 Shin B, Lee KR, Moon MW, Kim HY (1817) Extreme water repellency of nanostructured low-surface-energy non-woven fabrics. Soft Matter 2012:8
13.
Zurück zum Zitat Hardman SJ, Hutchings LR, Clarke N, Kimani SM, Mears LLE, Smith EF, Webster JRP, Thompson RL (2012) Surface modification of polyethylene with multi-end-functional polyethylene additives. Langmuir 28:5125CrossRef Hardman SJ, Hutchings LR, Clarke N, Kimani SM, Mears LLE, Smith EF, Webster JRP, Thompson RL (2012) Surface modification of polyethylene with multi-end-functional polyethylene additives. Langmuir 28:5125CrossRef
14.
Zurück zum Zitat Zhu SH, McManus NT, Tzoganakis C, Penlidis A (2007) Effect of a poly(dimethylsiloxane) modified polyolefin additive on the processing and surface properties of LLDPE. Polym Eng Sci 47:1309CrossRef Zhu SH, McManus NT, Tzoganakis C, Penlidis A (2007) Effect of a poly(dimethylsiloxane) modified polyolefin additive on the processing and surface properties of LLDPE. Polym Eng Sci 47:1309CrossRef
15.
Zurück zum Zitat Li X, Yu R, Zhao T, Zhang Y, Yang X, Zhao X, Huang W (2018) A self-healing polysiloxane elastomer based on siloxane equilibration synthesized through amino-ene Michael addition reaction. Eur Polym J 108:399CrossRef Li X, Yu R, Zhao T, Zhang Y, Yang X, Zhao X, Huang W (2018) A self-healing polysiloxane elastomer based on siloxane equilibration synthesized through amino-ene Michael addition reaction. Eur Polym J 108:399CrossRef
16.
Zurück zum Zitat Zheng P, McCarthy TJ (2012) A surprise from 1954: siloxane equilibration is a simple, robust, and obvious polymer self-healing mechanism. J Am Chem Soc 134:2024CrossRef Zheng P, McCarthy TJ (2012) A surprise from 1954: siloxane equilibration is a simple, robust, and obvious polymer self-healing mechanism. J Am Chem Soc 134:2024CrossRef
17.
Zurück zum Zitat Wu X, Yang X, Yu R, Zhao X-J, Zhang Y, Huang W (2018) A facile access to stiff epoxy vitrimers with excellent mechanical properties via siloxane equilibration. J Mater Chem A 6:10184CrossRef Wu X, Yang X, Yu R, Zhao X-J, Zhang Y, Huang W (2018) A facile access to stiff epoxy vitrimers with excellent mechanical properties via siloxane equilibration. J Mater Chem A 6:10184CrossRef
18.
Zurück zum Zitat Djinović VM, Antić VV, Djonlagić J, Govedarica MN (2000) Synthesis of α, ω-dicarboxypropyl oligodimethylsiloxanes by ion-exchange resin catalyzed equilibration polymerization. React Funct Polym 44:299CrossRef Djinović VM, Antić VV, Djonlagić J, Govedarica MN (2000) Synthesis of α, ω-dicarboxypropyl oligodimethylsiloxanes by ion-exchange resin catalyzed equilibration polymerization. React Funct Polym 44:299CrossRef
19.
Zurück zum Zitat Yactine B, Boutevin B, Ganachaud F (2009) Do-it-yourself functionalized silicones part 1: basic methods for characterization of commercial products. Polym Adv Technol 20:66CrossRef Yactine B, Boutevin B, Ganachaud F (2009) Do-it-yourself functionalized silicones part 1: basic methods for characterization of commercial products. Polym Adv Technol 20:66CrossRef
20.
Zurück zum Zitat Elsbernd CS, Spinu M, Krukonis VJ, Gallagher PM, Mohanty DK, McGrath JE (1989) Synthesis and fractionation studies of functionalized organosiloxanes. In: Ziegler JM, Fearon FWG (eds) Silicon-based polymer science. American Chemical Society, Washington DC, p 145CrossRef Elsbernd CS, Spinu M, Krukonis VJ, Gallagher PM, Mohanty DK, McGrath JE (1989) Synthesis and fractionation studies of functionalized organosiloxanes. In: Ziegler JM, Fearon FWG (eds) Silicon-based polymer science. American Chemical Society, Washington DC, p 145CrossRef
21.
Zurück zum Zitat Asuncion MZ, Laine RM (2010) Fluoride rearrangement reactions of polyphenyl- and polyvinylsilsesquioxanes as a facile route to mixed functional phenyl, vinyl T-10 and T-12 silsesquioxanes. J Am Chem Soc 132:3723CrossRef Asuncion MZ, Laine RM (2010) Fluoride rearrangement reactions of polyphenyl- and polyvinylsilsesquioxanes as a facile route to mixed functional phenyl, vinyl T-10 and T-12 silsesquioxanes. J Am Chem Soc 132:3723CrossRef
22.
Zurück zum Zitat Cella JA, Grade MM, Nye SA, Valkenburgh VM, Wengrovius JH (1992) Siloxane equilibration during the condensation reactions of organosilicon functional amines and anhydrides. Macromolecules 25:6355CrossRef Cella JA, Grade MM, Nye SA, Valkenburgh VM, Wengrovius JH (1992) Siloxane equilibration during the condensation reactions of organosilicon functional amines and anhydrides. Macromolecules 25:6355CrossRef
23.
Zurück zum Zitat Zhang Y, Li X, Wang W, Wang S, Xu J, Xu L, Li H (2018) Polysiloxane graft polyethylene synthesized by a novel heterofunctional condensation approach. React Funct Polym 122:68CrossRef Zhang Y, Li X, Wang W, Wang S, Xu J, Xu L, Li H (2018) Polysiloxane graft polyethylene synthesized by a novel heterofunctional condensation approach. React Funct Polym 122:68CrossRef
24.
Zurück zum Zitat Krumpfer JW, McCarthy TJ (2011) Rediscovering silicones: “unreactive” silicones react with inorganic surfaces. Langmuir 27:11514CrossRef Krumpfer JW, McCarthy TJ (2011) Rediscovering silicones: “unreactive” silicones react with inorganic surfaces. Langmuir 27:11514CrossRef
25.
Zurück zum Zitat Graffius G, Bernardoni F, Fadeev AY (2014) Covalent functionalization of silica surface using “inert” poly(dimethylsiloxanes). Langmuir 30:14797CrossRef Graffius G, Bernardoni F, Fadeev AY (2014) Covalent functionalization of silica surface using “inert” poly(dimethylsiloxanes). Langmuir 30:14797CrossRef
27.
Zurück zum Zitat Cypryk M, Apeloig Y (2002) Mechanism of the acid-catalyzed Si–O bond cleavage in siloxanes and siloxanols. A theoretical study. Organometallics 21:2165CrossRef Cypryk M, Apeloig Y (2002) Mechanism of the acid-catalyzed Si–O bond cleavage in siloxanes and siloxanols. A theoretical study. Organometallics 21:2165CrossRef
28.
Zurück zum Zitat Mandelkern L (2011) Fusion of homopolymers, In: Crystallization of polymers volume 1. Equilibrium concepts. Cambridge University Press, p 24 Mandelkern L (2011) Fusion of homopolymers, In: Crystallization of polymers volume 1. Equilibrium concepts. Cambridge University Press, p 24
29.
Zurück zum Zitat Shekh MI, Patel KP, Patel RM (2018) Electrospun ZnO nanoparticles doped core-sheath nanofibers: characterization and antimicrobial properties. J Polym Environ 26:4376CrossRef Shekh MI, Patel KP, Patel RM (2018) Electrospun ZnO nanoparticles doped core-sheath nanofibers: characterization and antimicrobial properties. J Polym Environ 26:4376CrossRef
30.
Zurück zum Zitat Tsuyumoto I (2018) High flame retardancy of amorphous sodium silicate on poly(ethylene-co-vinyl acetate) (EVA). Polym Bull 75:4967CrossRef Tsuyumoto I (2018) High flame retardancy of amorphous sodium silicate on poly(ethylene-co-vinyl acetate) (EVA). Polym Bull 75:4967CrossRef
31.
Zurück zum Zitat Shekh MI, Patel DM, Patel NN, Patel US, Patel KP, Patel RM (2018) Methacrylate copolymers and their composites with nano-CdS: synthesis, characterization, thermal behavior, and antimicrobial properties. Int J Ind Chem 9:153CrossRef Shekh MI, Patel DM, Patel NN, Patel US, Patel KP, Patel RM (2018) Methacrylate copolymers and their composites with nano-CdS: synthesis, characterization, thermal behavior, and antimicrobial properties. Int J Ind Chem 9:153CrossRef
Metadaten
Titel
Reaction of “unreactive” silicone: synthesis of long-chain alkyl fluorosilicone via a simple siloxane equilibration process
verfasst von
Yongjie Zhang
Mingshuai Fan
Xiaopei Li
Publikationsdatum
26.07.2019
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 6/2020
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-019-02883-z

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