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Fast Responsive Photochromic Materials Through Nanoemulsion Entrapment

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Fast Responsive Photochromic Materials Through Nanoemulsion Entrapment Department of Chemistry Faculty of science Fast responsive photochromic materials through nanoemulsion entrapment Héctor Torres Pierna PhD Thesis PhD in Material Science 2019 Supervisor: Tutor: Dr. Claudio Roscini Prof. Jordi Hernando Campos Memòria presentada per aspirar al Grau de Doctor per: Héctor Torres Pierna Vist i plau Director: Tutor: Dr. Claudio Roscini Prof. Jordi Hernando Bellaterra, de , . III To my family “We are trying to prove ourselves wrong as quickly as possible, because only in that way can we find progress.” ―Richard P. Feynman “There is nothing like looking, if you want to find something. You certainly usually find something, if you look, but it is not always quite the something you were after.” ―J.R.R. Tolkien, The Hobbit or There and Back Again IV Preface: This doctoral research has been performed under the scope of Industrial Doctorates Project. Financed by the Generalitat de Catalunya, the aim of this program is to promote technology transfer from public research centers and universities to private companies, to promote applied research and the launch of innovative products into de market.1 The research group where this work has been carried out is Nanostructured Functional Materials (Nanosfun), from the Catalan Institute of Nanoscience and Nanotechnology (ICN2), from which the thesis director Dr. Claudio Roscini is part.2 The company involved in this project is Futurechromes S.L.., a start-up company created to exploit a technology previously developed in Nanosfun.3 This doctoral research was carried out by Héctor Torres Pierna, currently in possession of a MSc degree in Industrial Chemistry, and ascribed to the Materials Science PhD program, at the Universitat Autònoma de Barcelona,4 under tuition of Prof. Jordi Hernando. As direct outcome of this industrial doctorate project, by the time this dissertation is deposited, a patent has been filed and granted (US10227527B2), a scientific journal article is pending of publication, several prototypes produced, and important steps towards the commercialization of photochromic products based on the developed technology have been done. 1 http://doctoratsindustrials.gencat.cat/en 2 https://icn2.cat/en/nanostructured-functional-materials-group 3 http://futurechromes.com/ 4 https://www.uab.cat/web/postgraduate/phds/all-phd-programmes/general- information/materials-science-1345467765430.html?param2=1345657420764 VI Industrial Doctorate Program Scheme VII Acknowledgements: First of all, I would like to acknowledge to the people that made this project possible. This starts by my PhD thesis director Dr. Claudio Roscini, who has invested brains, body and soul into this project, always having new insights and kind words to motivate me; and Prof. Daniel Ruiz-Molina, who with his knowledge and experience has paternally guided us in this project from its very beginning. Also of crucial importance, I would like to thank to Aurora Conill and Piergiorgio Pelassa, for personally trusting in me and this project, and for their talent, competence and boldness in the industrial research, finances and business that they provided to this project. Thanks also to our industrial partners (confidential) for joining us and in this adventure. Special acknowledgments also go to the lovely Dr. Nuria Vázquez-Mera and Prof. Jordi Hernando, for their original work on photochromic microcapsules that founded the grounds for this project 6 years ago, and for always having the perfect line to cheer up our moods. I would like to also personally thank to Bea, Ayala, Pablo, Julià, Fernando, Josep, Noe, Jaume, ‘Xiquet’… well, to ALL of my current and former partners in the Nanosfun research group, and also to Marcos Rosado, Javier Saiz and all the other ICN2 staff members who helped me along all these years. Thanks for your company and camaraderie, for all the coffees, for all the advices, for all whinings and laughters together. Last, but not least at all, to my family. Thanks to my parents, for helping me in every step of my life journey and for their moral support; and of course, thanks to Dydy, for always supporting me with all her strengths, for believing in me every single day and for brightening my heart and my mind every day with her blue moonlight. VIII Contents Preface: .............................................................................................................. VI Acknowledgements: ........................................................................................ VIII List of abbreviations:........................................................................................ XIII Abstract. ............................................................................................................ XV 1 Introduction .................................................................................................. 3 1.1 Photochromism ..................................................................................... 3 1.2 Applications of photochromic materials and products market ............ 4 1.3 T-type photochromic dyes .................................................................... 6 1.4 Fast fading and matrix effect ................................................................ 7 1.5 Transparency and light scattering .......................................................10 1.6 Nanoemulsion entrapment .................................................................11 1.7 Nanoemulsions ...................................................................................12 1.8 References: .........................................................................................15 2 Objectives....................................................................................................25 3 NEE technology development .....................................................................29 3.1 Proof of concept ..................................................................................29 3.2 NEE film characterization ....................................................................33 3.2.1 Photochromic performance ........................................................33 3.2.2 NEE film structure and composition ...........................................38 3.3 Universality of the emulsion entrapment technique ..........................45 3.3.1 Substitution of the dye................................................................45 3.3.2 Effect of the hydrophobic oil ......................................................48 IX 3.3.3 Effect of the film-forming, water soluble polymer .....................52 3.4 Effect of temperature on the photochromic performances of the NEE films .............................................................................................................53 3.5 Preliminary fatigue study ....................................................................55 3.6 Time stability of the nanoemulsion ....................................................56 3.7 Photochromic film recyclability ..........................................................60 3.8 Conclusions .........................................................................................63 3.9 References ..........................................................................................64 4 Towards commercial products....................................................................69 4.1 Improvement of the photochromic performance ..............................70 4.1.1 Selecting an appropriated neutral color dye ..............................70 4.1.2 Payload and thickness optimization ...........................................78 4.1.3 Improving photochromic performance of NEE films via triplet sensitization ....................................................................................................81 4.1.4 Improving the color development of NEE films. Conclusions .....85 4.2 Enhancement of the moisture resistance of NEE films .......................85 4.2.1 Preliminary moisture exposure tests and PVA grades screening ... .....................................................................................................86 4.2.2 Cross-linking of PVA 40-88 ..........................................................90 4.2.3 Highly hydrolyzed PVA matrixes ...............................................100 4.2.4 Water insoluble polymers .........................................................105 4.2.5 Enhancing moisture resistance of NEE films. Conclusions ........107 4.3 Reducing the haze of NEE films .........................................................109 4.3.1 Reducing the haze of NEE films with PVA 40-88 matrix ...........110 X 4.3.2 Reducing haze of NEE films with PVA 10-98 matrix ..................117 4.3.3 Reducing haze conclusions .......................................................121 4.4 Preliminary accelerated aging test....................................................123 4.5 Scaling-up NEE production ................................................................127 4.5.1 Scale-up of the NEE production set-up .....................................127 4.5.2 Nanoemulsion processing rate .................................................128 4.5.3 Scale-up of the film casting .......................................................130 4.6 Towards commercial products: conclusions .....................................132 4.7 References ........................................................................................134 5 Working prototypes ..................................................................................139
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