WO2010025381A2 - Article formed from electrospinning a dispersion - Google Patents
Article formed from electrospinning a dispersion Download PDFInfo
- Publication number
- WO2010025381A2 WO2010025381A2 PCT/US2009/055386 US2009055386W WO2010025381A2 WO 2010025381 A2 WO2010025381 A2 WO 2010025381A2 US 2009055386 W US2009055386 W US 2009055386W WO 2010025381 A2 WO2010025381 A2 WO 2010025381A2
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- WIPO (PCT)
- Prior art keywords
- dispersion
- set forth
- weight
- curable compound
- article
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- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920000131 polyvinylidene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- GNMJFQWRASXXMS-UHFFFAOYSA-M trimethyl(phenyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)C1=CC=CC=C1 GNMJFQWRASXXMS-UHFFFAOYSA-M 0.000 description 1
- MQAYPFVXSPHGJM-UHFFFAOYSA-M trimethyl(phenyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=CC=C1 MQAYPFVXSPHGJM-UHFFFAOYSA-M 0.000 description 1
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 description 1
- AXRFZYRPSHSKBF-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;iodide Chemical compound [I-].CCCCCCCCCCCCCC[N+](C)(C)C AXRFZYRPSHSKBF-UHFFFAOYSA-M 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0015—Electro-spinning characterised by the initial state of the material
- D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
- D01D5/0038—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion the fibre formed by solvent evaporation, i.e. dry electro-spinning
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/38—Formation of filaments, threads, or the like during polymerisation
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
- Y10T442/681—Spun-bonded nonwoven fabric
Definitions
- Electrospinning is a versatile method that includes use of an electrical charge to form a mat of fibers.
- electrospinning includes loading a solution into a syringe and driving the solution to a tip of the syringe with a syringe pump to form a droplet at the tip.
- Electrospinning also usually includes applying a voltage to the needle to form an electrified jet of the solution. The jet is then elongated and whipped continuously by electrostatic repulsion until it is deposited on a grounded collector, thereby forming the mat of fibers.
- the article may also exhibit an isotropic or non-isotropic nature of the water contact angle and/or the water contact angle hysteresis.
- the article may include domains that exhibit an isotropic nature and domains that exhibit a non-isotropic nature.
- the fibers may also be of any size and shape and are typically cylindrical. Typically, the fibers have a diameter of from 0.01 to 100, more typically of from 0.05 to 10, and most typically of from 0.1 to 1, micrometers ( ⁇ m).
- the fibers are often referred to as "fine fibers", which encompasses fibers having both micron-scale diameters (i.e., fibers having a diameter of at least 1 micron) and fibers having nanometer-scale diameters (i.e., fibers having a diameter of less than 1 micron).
- the fibers may also have a glass transition temperature (T g ) of from 25°C to 500°C.
- the liquid may be either the dispersed phase or the continuous phase.
- the dispersion includes solid particles as the dispersed phase and the liquid as the continuous phase.
- the dispersion includes a non-polar liquid as the dispersed phase and a polar liquid as the continuous phase.
- the liquid may be present in amounts of from 20 to 80, of from 30 to 70, of from 40 to 60, or in an amount of about 50, parts by weight per 100 parts by weight of the dispersion, so long as a total amount of the dispersion does not exceed 100 parts by weight.
- the dispersion may be further defined as a "colloid" or "colloid dispersion,” terminology which can be used interchangeably.
- the curable compound may be present in amounts of from 20 to 80, of from 30 to 70, of from 40 to 60, or in an amount of about 50, parts by weight per 100 parts by weight of the dispersion, so long as a total amount of the dispersion does not exceed 100 parts by weight.
- oligomer as used herein includes identifiable chemical groups, including dimers, trimers, tetramers and/or pentamers, linked together through reactive moieties capable of condensation.
- preferred organic reactive moieties capable of condensation include, but are not limited to, hydrolyzable moieties, hydroxyl moieties, hydrides, isocyanate moieties, amine moieties, amide moieties, acid moieties, alcohol moieties, amine moieties, acrylate moieties, carbonate moieties, epoxide moieties, ester moieties, and combinations thereof.
- the (condensation) curable compound may include hydrocarbylene and/or fluorocarbylene groups.
- Hydrocarbylene groups include a divalent moiety including carbon and hydrogen.
- Fluorocarbylene groups include a hydrocarbylene moiety with at least one of the hydrogens replaced with at least one fluorine atom.
- Typical fluorocarbylene groups include partially or wholly fluorine substituted alkylene groups.
- the (condensation) curable compound may also include olefinic moieties including acrylate moieties, methacrylate moieties, vinyl moieties, acetylenyl moieties, and combinations thereof.
- the dispersion may also include one or more surfactants.
- the dispersion includes a (first) surfactant and a second surfactant or multiple surfactants.
- the surfactant may be combined with the liquid, with the curable compound, or with both the liquid and the curable compound, prior to formation of the dispersion. Typically, the surfactant is combined with the liquid before the dispersion is formed.
- Surfactants are also known as surfactant active agents, surface active solutes, emulsifiers, emulgents, and tensides.
- the surfactant is present in an amount of from 0.1 to 100, more typically of from 0.01 to 5, even more typically of from 0.5 to 5, and most typically of from 1.5 to 5, parts by weight per 100 parts by weight of the dispersion.
- the dispersion may also include a thickener.
- thickeners increase a viscosity of the dispersion at low shear rates while maintaining flow properties of the dispersion at higher shear rates.
- Suitable thickeners for use in the instant invention include, but are not limited to, polyalkylene oxides such as polyethylene oxide, polypropylene oxide, polybutylene oxide, and combinations thereof.
- dispersions typically have two different types of viscosities, a total viscosity and a viscosity of the dispersed phase.
- the dispersion of the instant invention typically has a total viscosity of at least 20 centistokes at a temperature of 25 0 C.
- the dispersion has a viscosity of at least 20 centistokes, more typically from about 30 to about 100 centistokes, most typically from about 40 to about 75 centistokes at a temperature of 25 0 C using a Brookfield rotating disc viscometer equipped with a thermal cell and an SC4-31 spindle operated at a constant temperature of 25 0 C and a rotational speed of 5 rpm.
- the viscosity of the dispersed phase is not limited and is not believed to affect the total viscosity.
- the dispersed phase is solid and has an infinite viscosity.
- the dispersion may also have a zero shear rate viscosity of from 0.1 to 10, from 0.5 to 10, from 1 to 10, from 5 to 8, or about 6, PaS. Further, the dispersion may have a conductivity of from 0.01- 25 mS/m. In various embodiments, the conductivity of the dispersion ranges from 0.1-10, from 0.1-5, from 0.1-1, from 0.1- 0.5, or is about 0.3, mS/m.
- the dispersion may also have a surface tension of from 10-100 niN/m. In different embodiments, the surface tension ranges from 20-80, or from 20-50, mN/m. In one embodiment, the surface tension of the dispersion is about 30 mN/m.
- More typical conductivity-enhancing additives include quaternary ammonium-based organic salts including, but not limited to, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, phenyltrimethylammonium chloride, phenyltriethylammonium chloride, phenyltrimethylammonium bromide, phenyltrimethylammonium iodide, dodecyltrimethylammonium chloride, dodecyltrimethylammonium bromide, dodecyltrimethylammonium iodide, tetradecyltrimethylammonium chloride, tetradecyltrimethylammonium bromide, tetradecyltrimethylammonium iodide, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, and he
- the droplet is then typically exposed to a high-voltage electric field.
- the droplet exits the tip of the syringe in a quasi- spherical shape, which is the result of surface tension in the droplet.
- Application of the electric field results in the distortion of the spherical shape into that of a cone.
- the generally accepted explanation for this distortion in droplet shape is that the surface tension forces within the droplet are neutralized by the electrical forces.
- Narrow diameter jets of the dispersion emanate from the tip of the cone. Under certain process conditions, the jet of the dispersion undergoes the phenomenon of "whipping" instability. This whipping instability results in the repeated bifurcation of the jet, yielding a network of fibers.
- the fibers are ultimately collected on a collector plate.
- the liquid such as water
- the collector plate is typically formed from a solid conductive material such as, but not limited to, aluminum, steel, nickel alloys, silicon wafers, Nylon ® fabric, and cellulose (e.g., paper).
- the collector plate acts as a ground source for the electron flow through the fibers during electro spinning of the dispersion. As time passes the number of fibers collected on the collector plate increases and the non-woven fiber mat is formed on the collector plate.
- the fibers may be collected on the surface of a liquid that is not part of the dispersion, thereby achieving a free-standing non-woven mat.
- liquid that can be used to collect the fibers is water.
- the step of electro spinning comprises supplying electricity from a DC generator having generating capability of from about 10 to about 100 kilovolts (KV).
- KV kilovolts
- the syringe is electrically connected to the generator.
- the step of exposing the droplet to the high- voltage electric field typically includes applying a voltage and an electric current to the syringe.
- the applied voltage may be from about 5 KV to about 100 KV, typically from about 10 KV to about 40 KV, more typically from about 15 KV to about 35 KV, most typically from about 20 KV to about 30 KV. In one specific example, the applied voltage may be about 30 KV.
- the applied electric current may be from about 0.01 nA to about 100,000 nA, typically from about 10 nA to about 1000 nA, more typically from about 50 nA to about 500 nA, most typically from about 75 nA to about 100 nA. In one specific embodiment, the electric current is about 85 nA.
- the dispersion is at a temperature within 60°C of ambient temperature. More typically, when electro spinning, the dispersion is at a temperature within 60°C of a processing temperature.
- the step of electro spinning is believed to at least partially cure the condensation curable compound.
- the step of electro spinning completely cures the condensation curable compound.
- the step of electrospinning does not completely cure, or even partially cure, the curable compound such that an additional curing step is needed.
- the method may include the step of drying to more completely cure the curable compound.
- the curable compound is further defined as the condensation curable compound, it is hypothesized that the step of drying removes the liquid (e.g. water) and drives the condensation reaction to the right, i.e., towards completion.
- the method may also include the step of annealing the fibers. This step may be completed by any method known in the art. In one embodiment, the step of annealing may be used to enhance the hydrophobicity of the fibers. In another embodiment, the step of annealing may enhance a regularity of microphases of the fibers.
- the step of annealing may include heating the article. Typically, to carry out the step of annealing, the article is heated to a temperature above ambient temperature of about 20 0 C. More typically, the article is heated to a temperature of from about 40 0 C to about 400 0 C, most typically from about 40 0 C to about 200 0 C.
- a droplet at a tip of the stainless steel tube is electrospun into thin white fibers which are deposited onto the grounded aluminum foil.
- the step of electro spinning is performed at a plate gap of 30 cm, a tip protrusion of 3 cm, an applied voltage of 22 kV, and a flow rate of 1 mL/hr.
- the electro spinning is performed for one hour.
- the resultant fibers are one to five microns in diameter and tend to have fiber- fiber junctions. Spherical defects are present within the fibers, as shown in Figure 1. [0052] After electro spinning for one hour, the fibers form an opaque white membrane with a thickness of approximately 200 microns.
- the fibers formed in the aforementioned Example evidence that electro spinning a dispersion allows fibers to be formed that exhibit characteristics of the dispersed phase, i.e., the condensation curable compound, as opposed to the continuous phase.
- the fibers formed in this Example exhibit elastomeric stress and strain properties and an elastomeric stress-strain curve.
- the formation of these types of fibers allows for more efficient and accurate production of a variety of materials to be used in medical, scientific, and manufacturing industries.
- the use of the dispersion also allows for a variety of types of curable compounds to be utilized thus forming new products.
Abstract
Description
Claims
Priority Applications (7)
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CN2009801405233A CN102187022B (en) | 2008-08-29 | 2009-08-28 | Article formed from electrospinning dispersion |
JP2011525240A JP2012501390A (en) | 2008-08-29 | 2009-08-28 | Articles formed from electrospinning of dispersions |
MX2011002221A MX2011002221A (en) | 2008-08-29 | 2009-08-28 | Article formed from electrospinning a dispersion. |
CA2735440A CA2735440A1 (en) | 2008-08-29 | 2009-08-28 | Article formed from electrospinning a dispersion |
US13/061,232 US20110165811A1 (en) | 2008-08-29 | 2009-08-28 | Article Formed From Electrospinning A Dispersion |
EP20090792065 EP2318575A2 (en) | 2008-08-29 | 2009-08-28 | Article formed from electrospinning a dispersion |
IL211432A IL211432A0 (en) | 2008-08-29 | 2011-02-27 | Article formed from electrospinning a dispersion |
Applications Claiming Priority (2)
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US9297908P | 2008-08-29 | 2008-08-29 | |
US61/092,979 | 2008-08-29 |
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WO2010025381A3 WO2010025381A3 (en) | 2010-07-22 |
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US (1) | US20110165811A1 (en) |
EP (1) | EP2318575A2 (en) |
JP (1) | JP2012501390A (en) |
KR (1) | KR20110058827A (en) |
CN (1) | CN102187022B (en) |
CA (1) | CA2735440A1 (en) |
IL (1) | IL211432A0 (en) |
MX (1) | MX2011002221A (en) |
TW (1) | TW201016909A (en) |
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JP2012012754A (en) * | 2010-06-04 | 2012-01-19 | Jnc Corp | Fiber obtained from polymer containing silsesquioxane skeleton, fiber assembly and methods for producing them |
KR101272248B1 (en) | 2011-05-04 | 2013-06-13 | 한국과학기술연구원 | Organic/inorganic hybrid polysilsesquioxane microfiber using electrospinning, and the method for preparing the same |
US8715828B2 (en) | 2008-08-29 | 2014-05-06 | Dow Corning Corporation | Emulsion of metallized particles comprising a compound having a pendant Si-H group |
US9315631B2 (en) | 2012-01-18 | 2016-04-19 | Dow Corning Corporation | Methods of making saccharide siloxane copolymers |
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Also Published As
Publication number | Publication date |
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EP2318575A2 (en) | 2011-05-11 |
JP2012501390A (en) | 2012-01-19 |
KR20110058827A (en) | 2011-06-01 |
CN102187022A (en) | 2011-09-14 |
MX2011002221A (en) | 2011-08-03 |
CA2735440A1 (en) | 2010-03-04 |
WO2010025381A3 (en) | 2010-07-22 |
US20110165811A1 (en) | 2011-07-07 |
IL211432A0 (en) | 2011-05-31 |
TW201016909A (en) | 2010-05-01 |
WO2010025381A4 (en) | 2010-09-23 |
CN102187022B (en) | 2013-10-23 |
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