By Roger Corneliussen
By Roger Corneliussen
By Roger Corneliussen
Renewable Plasticizers
US Patent 8,802,877 (August 12, 2014), “Process for Modifying Vegetable Oils and Primary Plasticizer for Vinyl Polymers,” Milton Sobrosa Cordeiro, Sergio Teixeira, and Ariovaldo Fernandes, Jr. (NPC Industrias Quimicas Ltda., Mogi das Cruzes, Brazil).
Epoxidized vegetable oils have been used in small proportions as secondary plasticizers and thermo-co-stabilizers in the production of flexible, semi-rigid, and rigid polyvinyl chloride materials. However, the use of epoxidized triglycerides as primary plasticizers results in exudation due to limited compatibility with the polymeric matrix.
Cordeiro et al. developed compatible plasticizers for vinyl polymers by transesterification of vegetable oils and alcohols, catalyzed by an alcoxide generated by the reaction of an alcohol with an alkaline metal.
Controlled Release
US Patent 8,808,752 (August 19, 2014), “Controlled Release Articles and Method for Producing the Same,” Junji Oshima (Japan Envirochemicals, Ltd., Osaka-shi, Osaka, Japan).
Micro-encapsulation of antibiotics for preventing microorganism growth enables a slow controlled-release for lasting effects. This is done by interfacial polymerization involving an oil phase and an aqueous phase. This blending of different phases is complicated, leading to increased ingredient and production costs.
Oshima developed a simple process by dissolving the hydrophobic antibiotic in a hydrophobic acrylic monomer, dispersing the solution in water and polymerizing the monomer with an oil-soluble initiator. To be successful the antibiotic has a melting temperature less than 80°C. This process is simple, leading to decreased costs at all levels with good performance. The antibiotic is selected from a sterilizer, antibacterial agent, antiseptic, anti-algae, fungicide, herbicide, insecticide, attractant, repellent, rodenticide, etc. having antibiotic activities.
Non-Toxic Flame Retardants
US Patent 8,814,998 (August 26, 2014), “Method of Preparation and Application for Flame Retarding Composition,” Aziz Khadbai, Joseph Roberts Sparling, James Burton Anderson, and Ian Douglas Buchanan (Texas, USA).
Many consumer products use combustible materials such as wood, plastics, synthetic wood, and composites requiring flame retardants. However, common flame retardants can be toxic and dangerous to health.
Khadbai et al. developed water-soluble coatings of phosphates and borates. Such coatings are safe and effective flame retardants and can be applied by coating, painting, dipping, or spraying. An example water solution consists of 69-81 wt% water, 1-20 wt% ammonium polyphosphate, 4-5 wt% sodium borate, 4-5 wt% boric acid, and 0.8-1 wt% hydrogen peroxide.
Light-Emitting Diodes
US Patent 8,815,414 (August 26, 2014), “Polymer Compound and Polymer Light Emitting Device using the Same,” Shigeya Kobayashi, and Hidenobu Kakimoto (Sumitomo Chemical Company, Limited, Tokyo, Japan).
Certain polymers can form light-emitting compounds but they have insufficient light emission efficiency (light emission luminance per electric current). Kobayashi and Kakimoto developed light-emitting materials based on substituted benzocyclobutanes These polymers combined hole-transporting material with electron-transporting material, light-emitting material, stabilizer, and antioxidant.
Cyclobutane is condensed to aromatic rings such as benzene, naphthalene, anthracene, and pyrene and may have different substituents such as alkyl, alkoxy, alkylthio, and aryl groups. A polymer light-emitting device consists of a polymer electron-transporting layer between a cathode and a light-emitting layer, and a polymer hole-transporting layer between an anode and a light-emitting layer, resulting in a maximum outer quantum yield of 1.5 % when a voltage is applied between an anode and a cathode.
Polymeric Dyes
US Patent 8,816,040 (August 26, 2014), “Polymer Dye,” Takaki Kanbara, Junpei Kuwabara, Hikaru Yamada, and Nobutaka Fujimoto (Univ. of Tsukuba, Tsukuba and Sumitomo Seika Chemicals Co., Ltd., Kako-gun, Japan).
In many color applications, a metallic luster is desirable without problems of metallic fillers. Metallic problems range from solubility and toxicity, to blocking electromagnetic waves and corrosion. In addition, metals often require expensive and costly plating processes.
Kanbara et al. developed a polymer dye with a metallic luster for a variety of colors, without containing any metals. The 2000 to 50,000 number-average molecular weight polymer contains monocyclic heterocyclic groups such as diketopyrrolopyrrole, squalene, or carotene.
Reactive Nanoparticles
US Patent 8,816,107 (August 26, 2014),”Functionalised Nanoparticles, Their Production and Use,” Giovanni Baldi, Alfredo Ricci, Mauro Comes Franchini, Daniele Bonacchi, and Marco Bitossi (Colorobbia Italia S.p.A., Sovigliana-Vinci, Italy).
Nanoparticles are usually not soluble in a hydroalcoholic environment, which is very important for biomedical and pharmacological applications. Baldi et al. found that mono- and di-functional compounds are able to bind with nanoparticles of transition metal oxides and metals, forming stable complexes. The functionalized nanoparticles can be used in processes which require a specific hydrophobic/hydrophilic behavior such as the production of plastics (e.g., polyethylene or polyester) or synthetic fibers (e.g., nylon) and natural fibers (e.g., cotton).
Piezoelectric Polymer
US Patent 8,829,121 (September 9, 2014), “Piezoelectric Polymer Material and Method for Producing Same,” Mitsunobu Yoshida, Shunsuke Fujii, Hitoshi Onishi, Yoshiro Tajitsu, Taizo Nishimoto, Kazuhiro Tanimoto, and Kenichi Goto (Mitsui Chemicals, Inc., Minato-ku, Tokyo, and Kansai Univ., Suita-shi, Osaka, Japan).
In piezoelectric materials, mechanical stress results in electrically charged materials. Typical piezoelectric materials are PZT (PbZrO3–PbTiO3-based solid solution), which is a ceramic material. However, since PZT contains lead, toxicity is a problem, reducing potential medical applications. Because piezoelectric polymeric materials are generally electrically inferior to PZT, there is demand for improved polymer piezoelectric materials.
Yoshida et al. developed a helical chiral polymer such as polylactic acid with a weight-average molecular weight of 50,000-1,000,000, optical activity, and 20-80% crystallinity, showing enhanced piezoelectricity. This polymer can also be blended with polyvinylidene fluoride for piezoelectric materials.
Biodegradable Sorbents
US Patent 8,829,107 (September 9, 2014), “Biodegradable Superabsorbent Polymer Composition with Good Absorption and Retention Properties,” Franck Furno, Harald Schmidt, and Nicolaas De Bruin (Evonik Degussa GmbH, Essen, Germany).
Superabsorbent polymers based on acrylic acid or acrylates are not biodegradable and, therefore, not environmentally friendly. Furno, Schmidt, and De Bruin developed a biodegradable superabsorbent polymer by adding starch to the monomer mixture during polymerization of the superabsorbent polymer. The starch compound is introduced into the monomer solution as a powder or powder suspension and then polymerized to form a hydrogel. The hydrogel has a water content of 30 to about 80 wt% and is an easily kneadable dough-like mass. The monomers are unsaturated monomers copolymerizable with acrylamides and methacrylamides or vinylamides.
Aramid Polymerization
US Patent 8,835,600 (September 16, 2014), “Process of Forming an Aramid Copolymer,” Kiu-Seung Lee (E.I. du Pont de Nemours and Co., Wilmington, Delaware, USA).
Forming aramid copolymers is difficult because of the very different reactivity ratios of the reactants. Lee developed a method for forming a controlled copolymer composition by mixing two organic (N-methyl-2-pyrrolidone (NMP) or dimethylacetamide) solutions. One of the solutions contains a precise ratio of amino phenyl benzimidazole and paraphenylene diamine dihydrochloride. The other solution with the same solvent contains terephthaloyl dichloride. Polymerization occurs when the two solutions are mixed. HCl forms a rigid monomer, enabling precise copolymerization to high molecular weights.
Food Packaging
US Patent 8,840,826 (September 23, 2014), “Method of Making Multilayer Container,” Katsuro Sasauchi and Jun Kawata (Nakamoto Packs Co., Ltd., Osaka, Japan).
Most food containers are formed by thermoforming sheet plastics. However, many food products are heated by microwaves to 100°C. Most thermoplastic containers do not have high heat resistance and transparency for this situation.
Sasauchi and Kawata found a suitable thermoformed multilayer sheet consisting of an A-PET layer and a functional resin layer with oxygen barrier properties and impact resistance. During thermoforming there are two stretching and heat setting processes.
Hydrogels
US Patent 8,841,408 (September 23, 2014), “Macromonomers and Hydrogel Systems using Native Chemical Ligation, and Their Methods of Preparation,” Phillip B Messersmith, Bi-Huang Hu, Jing Su (Northwestern Univ., Evanston, Illinois, USA).
Hydrogels are hydrophilic polymeric networks which can absorb and retain large amounts of water. Hydrogels are useful in controlled release systems for drug delivery, tissue repair, and tissue engineering, and as surgical sealants and adhesives. Although great progress in medical applications of hydrogels has been made, it remains challenging to develop cross-linking methods that satisfy the demanding biological and handling requirements for medical treatment. Accordingly, there is an unmet need for biocompatible hydrogels capable of deployment by minimally invasive methods and solidification under physiological conditions.
Messersmith, Hu, and Su developed biocompatible macromonomer hydrogels using a thioester that readily reacts with an N-terminal thiol (cysteine) through transesterification and rearrangement to form an amide bond through a five-member ring intermediate.
Barrier Sensors
US Patent 8,845,969 (September 30, 2014), “Material, System, and Method that Provide Indication of a Breach,” Mahalaxmi Gita Bangera, Michael H. Baym, Roy P.Diaz, Roderick A. Hyde, Muriel Ishikawa; Y., Edward K. Y. Jung, Jordin T. Kare, Erez Lieberman, Nathan P. Myhrvold, Dennis J. Rivet, Michael A. Smith, Elizabeth A. Sweeney, and Lowell L Wood, Jr. (The Invention Science Fund I, LLC., Bellevue, Washington, USA).
Barrier materials are very useful, but if the barrier is broken, the effects can be serious. Some signaling system indicating a breach would be helpful.
Bangera et al. developed a multilayer film barrier with a barrier layer and a signaling layer for clothing, like gloves. A breach in some way changes sends an electromagnetic signal to a detector. The detector can include a radio frequency identification sensor and/or a radio frequency identification reader. This material may also include a second signaling layer which emits a chemical when broken. The signaling layer is based on optical fibers which changes a signal when broken. The second signaling layer is formed by coating with or dipping into a liquid containing an indicator chemical.
Polynorbornene
US Patent 8,835,580 (September 16, 2014), “Catalyst for Norbornene Monomer Polymerization and Method for Producing Norbornene Polymer,” Satoshi Fujibe and Nobuyuki Kibino (Showa Denko K.K., Tokyo, Japan).
Polynorbornene is one of the cyclic polyolefins that are special in that the crystals are very similar to the amorphous phase, resulting in strength, stiffness, transparency, and heat resistance. Applications include optical films with a low glass transition of 35°C. The addition of polar groups could greatly expand its usefulness and improve its range of properties. Although norbornene monomers are polymerized with transition metal catalysts, polar groups deactivate these catalysts, making polymerization of monomers with polar groups impossible.
Fujibe and Kibino developed a catalyst for polar norbornene polymerization. The catalyst is based on a transition metal complex containing a π-allyl ( ξ3-allyl) ligand and a bidentate β-ketoimine ligand as a main catalyst, and a norbornene compound in which a methylene chain is introduced between a norbornene skeleton and an ester group.
Restoring Soil
US Patent 8,802,915 (August 12, 2014), “Hydrocarbon Decomposition for Soil and Water Remediation,” Pedro Murillo Gutierrez (Chihuahua, Mexico).
There are many methods for cleaning hydrocarbon-polluted soil. These methods are usually based on sequestrants, flocculants, or surfactants which extract the hydrocarbons for transport to some other site. But the hydrocarbon pollution is only transfered to another site and not eliminated.
Murillo Gutierrez developed a dihydroguaiaretic surfactant with a phosphate source. When mixed with the contaminated soil, the surfactant induces a break-up of the hydrocarbons and oxidation into mineral fertilizers at room temperature and atmospheric pressure. The end product is a fertile soil with complete elimination of the pollutant.