WO2024254474A2 - Copolymères séquencés à fractions de polyester et leurs applications - Google Patents

Copolymères séquencés à fractions de polyester et leurs applications Download PDF

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Publication number
WO2024254474A2
WO2024254474A2 PCT/US2024/033044 US2024033044W WO2024254474A2 WO 2024254474 A2 WO2024254474 A2 WO 2024254474A2 US 2024033044 W US2024033044 W US 2024033044W WO 2024254474 A2 WO2024254474 A2 WO 2024254474A2
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independently
functionalized
unfunctionalized
moiety
composition
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WO2024254474A3 (fr
Inventor
Osama M. Musa
Matthew Adam Henry FARMER
Steven Peter Armes
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ISP Investments LLC
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ISP Investments LLC
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6882—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
    • C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6852—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2438/00—Living radical polymerisation
    • C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]

Definitions

  • RAFT reversible addition–fragmentation chain transfer
  • PCT published application 2020/117170 discloses a biosensor comprising a polyphosphonoundecyl acrylate-co-polyvinylimidazole-co-polyvinylferrocene-co-polyglycidyl methacrylate tetra block copolymer as an electron transmitter between the glucose oxidase and redox centre of the electrode for measuring glucose from sweat.
  • U.S. U.S.
  • U.S. patent 10,905,636 discloses block copolymers comprising repeating units derived from monomers comprising lactam and acryloyl moieties and hydrophobic monomers, compositions, and applications thereof.
  • U.S. published application 2020/0407470 discloses methods of synthesis of homopolymers and non-homopolymers comprising repeating units derived from monomers comprising lactam and acryloyl moieties in an aqueous medium.
  • U.S. published application 2019/0382519 discloses cross-linked block copolymers comprising repeating units derived from monomers comprising lactam and acryloyl moieties, compositions, and applications thereof.
  • U.S. published application 2019/0382519 discloses cross-linked block copolymers comprising repeating units derived from monomers comprising lactam and acryloyl moieties, compositions, and applications thereof.
  • Non-limiting examples of alkalizing agent can be chosen from ammonia, alkali carbonates, alkanolamines, like mono-, di- and triethanolamines, as well as their derivatives, sodium or potassium hydroxides and compounds of the following formula: wherein R 1 may be a propylene residue that may be optionally substituted with an hydroxyl group or a C 1 -C 4 alkyl radical; R 2 , R 3 , R 4 and R 5 are identical or different and represent a hydrogen atom, a C1-C4 alkyl radical or C1-C4 hydroxyalkyl radical.
  • the personal care compositions may additionally comprise one or more buffers.
  • Suitable buffering agents include, but are not limited to alkali or alkali earth carbonates, phosphates, bicarbonates, citrates, borates, acetates, acid anhydrides, succinates and the like, such as sodium phosphate, citrate, borate, acetate, bicarbonate, and carbonate.
  • the personal care compositions may be formulated in any of the product forms known to a person of ordinary skill in the art. Non-limiting product forms are described below.
  • Non-limiting sun care product forms include: solutions, liquids, creams, powders, lotions, gels, pastes, waxes, aerosols, sprays, mists, roll-ons, sticks, milks, emulsions, and wipes.
  • Non-limiting body care product forms include: foams, peels, masks, gels, sticks, aerosols, lotions, salts, oils, balls, liquids, powders, peels, pearls, bar soaps, liquid soaps, body washes, cleansers, scrubs, creams, flakes, other bath and shower products, shaving products, waxing products, and sanitizers.
  • (6) Foot care Non-limiting foot care product forms include: mousses, creams, lotions, powders, liquids, sprays, aerosols, gels, flakes, and scrubs.
  • Non-limiting oral care product forms include: toothpastes, adhesives, gums, gels, powders, creams, solutions, lotions, liquids, dispersions, suspensions, emulsions, tablets, capsules, rinses, flosses, aerosols, strips, films, pads, bandages, microencapsulated products, syrups, and lozenges.
  • personal care compositions comprising polymer(s) described herein complexed with iodine. These compositions may be used in treating skin conditions, non- limiting examples of which include dermatitis, wounds, bacterial infections, burns, rashes, and herpes.
  • the personal care compositions may be used in products for male and/or female personal grooming and/or toiletry such as: sanitary napkins, baby diapers, adult diapers, feminine products, products for incontinence, and other related products.
  • products for male and/or female personal grooming and/or toiletry such as: sanitary napkins, baby diapers, adult diapers, feminine products, products for incontinence, and other related products.
  • An array of additional personal care compositions, methods, and uses are contemplated.
  • compositions may be found in the following brochures by Ashland Specialty Ingredients (Bridgewater, NJ), each of which is herein incorporated in its entirety by reference: Plasdone TM K-29/32, Advanced non-oxidative, non-abrasive teeth whitening in toothpastes, mouthwashes, and oral rinses (2010), Polymers for oral care, product and applications guide (2002), A composition guide for excellent hair styling gels and lotions (4/2003), PVP (polyvinylpyrrolidone) (no date provided), and Textile chemicals, solutions for the most challenging product environment (no date provided).
  • PVP polyvinylpyrrolidone
  • compositions described in the publications listed below, each of which is herein incorporated in its entirety by reference: (1) Prototype Compositions - Personal Care Products (2009) from Xiameter, Dow Corning. (2) Sun care compositions under the category “Refreshing Sun”, “Younger Sun”, “Sun for Men”, and “Sunny Glow” from Dow Corning. (3) Cosmetic Nanotechnology, Polymers and Colloids in Cosmetics, 2007, ACS Symposium Series. (4) Review Paper: Lipid nanoparticles (SLN, NLC) in cosmetic and pharmaceutical dermal products, International Journal of Pharmaceutics, Volume 366, 2009. Optional: Additional composition ingredients [00134] It is also contemplated that the personal care compositions optionally may contain one or more additional ingredients.
  • Conditioning agents may be chosen from synthetic oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, proteins and hydrolyzed proteins, cationic surfactants, ceramide type compounds, fatty amines, fatty acids and their derivatives, as well as mixtures of these different types of compounds.
  • suitable synthetic oils include: polyolefins, e.g., poly- ⁇ - olefins, such as polybutenes, polyisobutenes, polydecenes, and blends thereof. The polyolefins may be hydrogenated.
  • the conditioning agent may be a fluorinated or a perfluorinated oil.
  • the fluoridated oils may also be fluorocarbons such as fluoramines, e.g., perfluorotributylamine, fluoridated hydrocarbons such as perfluorodecahydronaphthalene, fluoroesters, fluoroethers, and blends thereof.
  • Non-limiting examples of suitable silicones include: polyalkyl siloxanes, polyaryl siloxanes, polyalkyl aryl siloxanes, silicone gums and resins, polyorgano siloxanes modified by organofunctional groups, and blends thereof.
  • Suitable polyalkyl siloxanes include polydimethyl siloxanes with terminal trimethyl silyl groups or terminal dimethyl silanol groups (dimethiconol) and polyalkyl (C1-C20) siloxanes.
  • Suitable polyalkyl aryl siloxanes include polydimethyl methyl phenyl siloxanes and polydimethyl diphenyl siloxanes.
  • Suitable silicone gums include polydiorganosiloxanes, such as those having a number- average molecular weight between 200,000 Da and 1,000,000 Da used alone or mixed with a solvent.
  • suitable silicone gums include: polymethyl siloxane, polydimethyl siloxane/methyl vinyl siloxane gums, polydimethyl siloxane/diphenyl siloxane, polydimethyl siloxane/phenyl methyl siloxane, polydimethyl siloxane/diphenyl siloxane/methyl vinyl siloxane, and blends thereof.
  • Non-limiting examples of suitable silicone resins include silicones with a dimethyl/trimethyl siloxane structure and resins of the trimethyl siloxysilicate type.
  • the organo-modified silicones suitable for use include silicones such as those previously defined and containing one or more organofunctional groups attached by means of a hydrocarbon radical, and grafted silicone polymers.
  • the organo-modified silicones may be one from the amino functional silicone family.
  • the silicones may be used in the form of emulsions, nano-emulsions, or micro- emulsions.
  • the cationic polymers that may be used as conditioning agents generally have a molecular weight (average number) from about 500 Da to about 5,000,000 Da.
  • the copolymers may contain one or more units derived from acrylamides, methacrylamides, diacetone acrylamides, acrylic or methacrylic acids or their esters, vinyl lactams such as vinyl pyrrolidone or vinyl caprolactam, and vinyl esters.
  • polymers composed of piperazinyl units and alkylene or hydroxy alkylene divalent radicals with straight or branched chains, possibly interrupted by atoms of oxygen, sulfur, nitrogen, or by aromatic or heterocyclic cycles, as well as the products of the oxidation and/or quaternization of such polymers.
  • water-soluble polyamino amides prepared by polycondensation of an acid compound with a polyamine. These polyamino amides may be reticulated.
  • a polyalkylene polyamine containing two primary amine groups and at least one secondary amine group with a dioxycarboxylic acid chosen from among diglycolic acid and saturated dicarboxylic aliphatic acids having 3 to 8 atoms of carbon.
  • Such polymers include those described in U.S. patents 3,227,615 and 2,961,347.
  • (9) cyclopolymers of alkyl diallyl amine or dialkyl diallyl ammonium such as the homopolymer of dimethyl diallyl ammonium chloride and copolymers of diallyl dimethyl ammonium chloride and acrylamide.
  • Non-limiting examples of suitable compounds include: hydrolyzed collagens having triethyl ammonium groups, hydrolyzed collagens having trimethyl ammonium and trimethyl stearyl ammonium chloride groups, hydrolyzed animal proteins having trimethyl benzyl ammonium groups (benzyltrimonium hydrolyzed animal protein), hydrolyzed proteins having groups of quaternary ammonium on the polypeptide chain, including at least one C1-C18 alkyl, and blends thereof.
  • the conditioning agent may also comprise a cationic surfactant such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide.
  • Conditioning agents may also be selected from the group consisting of: mono-, di-, and tri- alkyl amines, and quaternary ammonium compounds with a counterion such as a chloride, a methosulfate, a tosylate, etc.
  • Non-limiting examples of suitable amines include: cetrimonium chloride, dicetyldimonium chloride, behentrimonium methosulfate, and blends thereof.
  • the conditioning agent may comprise a fatty amine.
  • suitable fatty amines include dodecyl amines, cetyl amines, stearyl amines such as stearamidopropyl dimethylamine, and blends thereof.
  • the conditioning agent may comprise a fatty acid or derivative(s) thereof.
  • Non-limiting examples of suitable fatty acids include: myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, isostearic acid, and blends thereof.
  • the derivatives of fatty acids include carboxylic ester acids including mono-, di-, tri- and tetra- carboxylic acids esters, amides, anhydrides, esteramides, imides, and mixtures of these functional groups.
  • compositions may also be in the form of aqueous or hydro-alcoholic solutions.
  • the physiological and cosmetically acceptable medium may consist exclusively of water, a cosmetically acceptable solvent, or a blend of water and a cosmetically acceptable solvent, such as a lower alcohol composed of C1 to C4, such as ethanol, isopropanol, t-butanol, n-butanol, alkylene glycols such as propylene glycol, and glycol ethers.
  • personal care compositions may comprise vitamin(s), provitamin(s), and/or mineral(s).
  • Non-limiting examples of suitable vitamins include ascorbic acid (vitamin C), vitamin E, vitamin E acetate, vitamin E phosphate, B vitamins such as B3 and B5, niacin, vitamin A, derivatives thereof, and blends thereof.
  • suitable provitamins include: panthenol, retinol, and blends thereof.
  • suitable minerals include: talc, clay, calcium carbonate, silica, kaolin, mica, and blends thereof. Further examples of minerals that may be used in the personal care compositions may be found in a brochure titled Minerals for personal care from Imerys Performance Minerals, the disclosure of which is herein incorporated in its entirety by reference.
  • Non-limiting examples of suitable cationic surfactants include: derivatives of aliphatic quaternary ammonium compounds having at least one long alkyl chain containing from about 8 to about 18 carbon atoms, such as, lauryl trimethylammonium chloride, cetyl pyridinium chloride, cetyl trimethylammonium bromide, di-isobutylphenoxyethyl-dimethylbenzylammonium chloride, coconut alkyltrimethylammonium nitrite, cetyl pyridinium fluoride, and blends thereof.
  • quaternary ammonium fluorides having detergent properties such as compounds described in U.S. Patent 3,535,421.
  • Nonionic surfactants may act as germicides in the compositions disclosed herein.
  • Nonionic surfactants useful herein include compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound which may be aliphatic or alkylaromatic in nature.
  • Non-limiting examples of suitable zwitterionic surfactants include betaines and derivatives of aliphatic quaternary ammonium compounds in which the aliphatic radicals can be straight chain or branched, and which contain an anionic water-solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Stepan ® Pearl 2 Stepan ® Pearl 4, Stepan ® Pearl Series, Neobee ® M-20, Stepan ® PTC, Amphosol ® 2CSF, Steol ® , Stepan-Mild ® GCC, Stepan ® SLL-FB, Stepanol ® AM, Stepanol ® PB, Alpha-Step ® BSS-45, Bio-Terge ® 804, Stepan-Mild ® L3, Stepan ® SLL-FB, Stepan ® SSL-CG, and Stepanol ® CFAS-70 from Stepan Company.
  • compositions that may comprise the polymers described herein. Disclosures on such compositions may be found in the publications listed below, each of which is herein incorporated in its entirety by reference: (1) Prototype Compositions - Personal Care Products (2009) from Xiameter, Dow Corning. (2) Sun care compositions under the category “Refreshing Sun”, “Younger Sun”, “Sun for Men”, and “Sunny Glow” from Dow Corning. (3) Cosmetic Nanotechnology, Polymers and Colloids in Cosmetics, 2007, ACS Symposium Series.
  • Non-limiting examples of properties that may be beneficially modified by the block copolymers and compositions disclosed herein are solution viscosity, rheology, thickening, film formation, lubricity, gloss, adhesion, impact resistance, fluid snap, film brittleness, film toughness, coating hardness, water resistance, tack, surface gloss and shine, surface tension, wetting, foaming and foam stabilization, tensile strength, solvency, solubilization speed, compatibility, bio- adhesion, particulate suspension, particulate dispersive properties, dispersive properties, delivery of hydrophobic compositions, formulation stabilization, suspension stability, dispersion stability, flexibility, chemical resistance, abrasion resistance, penetration, hydrolytic degradability, biodegradability, biocompatibility, and combinations thereof.
  • This vial was placed in an ice bath and deoxygenated with a stream of dry N 2 gas for 30 min. The vial was then allowed to warm to room temperature for 10 min before being immersed in an oil bath set at 80 °C. The reaction mixture was stirred magnetically and monitored by visual inspection. As soon as the reaction mixture became much more viscous after 7.5 min, deoxygenated deionized water (7.07 mL, preheated to 80 °C, targeting 10% w/w solids) was added using a degassed syringe/needle. At this point, the reaction vial was removed from the oil bath and subjected to vortex mixing for 2 min to ensure a homogeneous solution, then re-immersed in the oil bath.
  • the vial was then allowed to warm to room temperature for 10 min before being immersed in an oil bath set at 80 °C.
  • the reaction mixture was stirred magnetically and monitored by visual inspection. As soon as the reaction mixture became much more viscous after 14 min, deoxygenated deionized water (2.98 mL, preheated to 80 °C, targeting 10% w/w solids) was added using a degassed syringe/needle. At this point, the reaction vial was removed from the oil bath and subjected to vortex mixing for 2 min to ensure a homogeneous solution, then re-immersed in the oil bath.
  • This vial was placed in an ice bath and deoxygenated with a stream of dry N 2 gas for 30 min. The vial was then allowed to warm to room temperature for 10 min before being immersed in an oil bath set at 80 °C. The reaction mixture was stirred magnetically and monitored by visual inspection. As soon as the reaction mixture became much more viscous after 10min, deoxygenated deionized water (6.87 mL, preheated to 80 °C, targeting 10% w/w solids) was added using a degassed syringe/needle. At this point, the reaction vial was removed from the oil bath and subjected to vortex mixing for 2 min to ensure a homogeneous solution, then reimmersed in the oil bath.
  • Potassium dihydrogen phosphate (10.0 g, 0.073 mol) was dissolved in deionized water (80 mL). Then the solution pH was adjusted with 0.1 M HCl and made up to 100 mL using further deionized water to provide a final solution pH of 2.9. Ammonium chloride (6.80 g, 0.13 mol) was dissolved in 28% aqueous ammonia solution (100 mL) to afford a final solution pH of 10.8. A single Oxoid PBS tablet was dissolved in deionized water (100 mL) and 0.1 M HCl was used to adjust the solution pH to pH 7.4.
  • a 10% w/w aqueous dispersion of PDMAC50-PCL16-PDMAC50 nanoparticles was diluted to 1.0% w/w using each of the above aqueous solutions in turn.
  • the resulting three aqueous dispersions were stirred at 37 °C for four weeks and sampled periodically for GPC and DLS analysis.
  • the same protocol was employed to study the hydrolytic degradation of aqueous dispersions of PCL21-PDMAC70 and PCL42-PDMAC120 nanoparticles.
  • Table 1 Summary of reagent quantities used for the ring-opening polymerization of CL in dry toluene at 20 ° C. Each reaction was quenched after the stated reaction time using benzoic acid.
  • Table 2 Summary of reagent quantities used for the DCC/DMAP catalyzed esterification of PCL precursors using the CEPA RAFT agent. Esterification was performed under nitrogen in refluxing dry CH 2 Cl 2 .
  • Azoxystrobin 2.00 g
  • PDMAC x -PCL 16 -PDMAC x nanoparticles (0.25 g, 10% w/w)
  • SAG1572 antifoam (0.10 g, 1.0% w/w)
  • deionized water 7.65 g
  • This aqueous suspension was then ball-milled using an IKA Ultra-Turrax Tube Drive at 6000 rpm for 30 min. The beads were removed by filtration to afford a 20% w/w aqueous suspension of azoxystrobin microparticles.
  • This suspension was purified by centrifugation for 10 min at 13 000 rpm using a Thermo Heraeus Biofuge Pico centrifuge. The aqueous supernatant was decanted and the sedimented azoxystrobin microparticles were redispersed in deionized water. Two further centrifugation- redispersion cycles were performed to remove any excess non-adsorbed triblock copolymer nanoparticles prior to characterization by optical microscopy, laser diffraction and TEM. Characterization Techniques 1 H NMR Spectroscopy [00251] Spectra were obtained using a 400 MHz Bruker Avance-400 spectrometer operating at 298 K with 16 scans being averaged per spectrum.
  • the mean z-average particle diameter (D z ) and polydispersity index (PDI) were averaged over three consecutive runs consisting of ten measurements each.
  • D z The mean z-average particle diameter
  • PDI polydispersity index
  • D n The mean number-average particle diameter
  • D n The mean number-average particle diameter
  • count rate were averaged over three consecutive runs consisting of ten measurements each.
  • Copper/palladium grids (Agar Scientific, UK) were coated in-house with a thin film of amorphous carbon and then treated with a plasma glow discharge for 30 seconds to generate a hydrophilic surface.
  • a 10 ⁇ L droplet of freshly diluted 1.0% w/w aqueous copolymer dispersion was placed on a hydrophilic grid for 1 min, then blotted to remove excess sample.
  • Each grid was negatively stained for a further 25 seconds using a 10 ⁇ L droplet of 0.75% w/v aqueous uranyl formate solution, which was then carefully blotted to remove excess stain.
  • Each grid was dried with the aid of a vacuum hose. Imaging was performed using a FEI Tecnai Spirit 2 microscope equipped with an Orius SC1000B camera operating at 80 kV.
  • Aqueous Electrophoresis A Malvern Instruments Zetasizer Nano ZS instrument was used to characterize copolymer dispersions diluted to 0.1% w/w using 1 mM KCl as background electrolyte. Mobilities were determined at 20 °C and the solution pH was adjusted using either 0.1 M NaOH or 0.1 M HCl as required. Zeta potentials were calculated from the Henry equation using the Smoluchowski approximation.
  • Differential Scanning Calorimetry Measurements were performed using a TA DSC25 Discovery series instrument operating from -90 to 100 °C at a rate of 10 °C min –1 using aluminum T zero pans and standard lids. Instrument calibration was performed using an indium standard.
  • Shear-induced Polarized Light Imaging Shear alignment experiments were conducted using a mechano-optical rheometer (Anton Paar Physica MCR301 with SIPLI attachment). Measurements were performed using a plate ⁇ plate geometry composed of a 25 mm polished steel plate and a fused quartz plate connected to a variable temperature Peltier system. The gap between plates was set at 0.50 mm for all experiments. An additional Peltier hood was used to ensure good control of the sample temperature. Sample illumination was achieved using an Edmund Optics 150 W MI-150 high-intensity fiber- optic white light source. The polarizer and analyzer axes were crossed at 90° to obtain polarized light images, which were recorded using a color CCD camera (Lumenera Lu165c)

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Graft Or Block Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention propose des copolymères séquencés comprenant des liaisons polyester. Ces copolymères sont obtenus par réaction de précurseurs de formation de polyester, d'agents RAFT et de monomères polymérisables par voie radicalaire. L'invention propose en outre des compositions comprenant les copolymères séquencés et leurs applications dans divers domaines industriels. L'invention propose en outre un procédé de réduction de la taille de particules d'un principe actif par obtention d'une composition qui comprend des particules colloïdales des copolymères séquencés et du principe actif et par soumission de la composition à une opération de réduction de taille appropriée. Chaque a, b et R11 sont décrits dans la présente invention.
PCT/US2024/033044 2023-06-08 2024-06-07 Copolymères séquencés à fractions de polyester et leurs applications Ceased WO2024254474A2 (fr)

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US202363507007P 2023-06-08 2023-06-08
US63/507,007 2023-06-08
US202363583897P 2023-09-20 2023-09-20
US63/583,897 2023-09-20

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AU2014296278C1 (en) * 2013-07-30 2023-02-02 Genevant Sciences Gmbh Block copolymers and their conjugates or complexes with oligonucleotides
CN109996757A (zh) * 2015-06-12 2019-07-09 罗地亚经营管理公司 含枝状体的混合纳米粒子、生产此类混合纳米粒子的方法以及它们的用途
WO2020126448A1 (fr) * 2018-12-20 2020-06-25 Solvay Specialty Polymers Italy S.P.A. Dispersion polymère de fluorure de vinylidène
US20240117103A1 (en) * 2022-09-15 2024-04-11 Seoul National University R&Db Foundation Polymer, method of preparing same, and polyurethane prepared by using same

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