WO2017100045A1 - Sulfonamides pipérazine fluorés - Google Patents

Sulfonamides pipérazine fluorés Download PDF

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Publication number
WO2017100045A1
WO2017100045A1 PCT/US2016/064079 US2016064079W WO2017100045A1 WO 2017100045 A1 WO2017100045 A1 WO 2017100045A1 US 2016064079 W US2016064079 W US 2016064079W WO 2017100045 A1 WO2017100045 A1 WO 2017100045A1
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composition
mmol
polymer
fibers
water
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PCT/US2016/064079
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English (en)
Inventor
Georgiy Teverovskiy
Chetan P. Jariwala
Ajay K. VIDYASAGAR
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3M Innovative Properties Company
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Publication of WO2017100045A1 publication Critical patent/WO2017100045A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43—Compounds containing sulfur bound to nitrogen
    • C08K5/435—Sulfonamides

Definitions

  • thermoplastic composition fluorochemical composition and shaped articles made from the thermoplastic composition.
  • organofluorine compounds as surface-active agents (i.e., surfactants) and surface-treating agents is due in large part to the extremely low free-surface energy of a C 6 -Ci2 fluorocarbon group, according to H. C. Fielding, "Organofluorine Compounds and Their Applications," R. E. Banks, Ed., Society of Chemical Industry at p. 214 (1979).
  • organofluorine substances described above are those which have carbon- bonded fluorine in the form of a monovalent fluoroaliphatic radical such as a
  • fluorochemical having a melting point of at least about 25°C and a molecular weight of about 500 to 2500, the fluorochemical being a fluorochemical piperazine, oxazolidinone or perfluorinated alkane having from 15 to 50 carbon atoms.
  • U.S. Patent No. 5,300,587 (Macia et al.) describes oil-repellent polymeric compositions made by blending a perfluoropolyether and a thermoplastic polymer.
  • WO 98/15598 describes water- and oil-repellent resin compositions useful, e.g., for kitchenware and bathroom utensils, comprising thermoplastic or thermosetting resin and perfluoroalkylated polymer, such compositions exhibiting superior anti-fouling and mouldability.
  • melt-blown microfiber webs continue to be in widespread use for filtering particulate contaminants, e.g., as face masks and as water filters, and for other purposes, e.g., to remove oil from water.
  • Rf is a perfluorinated group of having an average of 3 to 5 carbon atoms
  • This invention further provides a polymer composition comprising the partially fluorinated compounds of Formula I and a thermoplastic or thermoset polymer.
  • a polymer composition of this invention can be melted or shaped, for example by extrusion or molding, to produce shaped articles, such as fibers, films and molded articles whose surfaces exhibit excellent oil- and water repellency.
  • the repellent polymer composition is especially useful in the preparation of nonwoven fabrics used in medical gowns and drapes, where repellency to bodily fluids is mandated.
  • Films made from repellent polymer compositions of this invention are useful, for example, for moisture and/or grease-resistant packaging, release liners, and multilayer constructions.
  • the present invention provides oily mist resistant electret filter media comprising polypropylene electret fibers made from repellent polymer
  • Alkyl means a linear or branched, cyclic or acylic, saturated or unsaturated monovalent hydrocarbon .
  • Alkylene means a linear or branched cyclic or acylic, saturated or unsaturated, polyvalent hydrocarbon.
  • Alkylene means a group defined above with an aryl group attached to the alkylene, e.g., benzyl, 1 -naphthyl ethyl, and the like.
  • Hydrocarbyl is inclusive of hydrocarbyl alkyl, alkylene and aryl groups of all indicated valent states. Unless otherwise indicated, the non-polymeric hydrocarbyl groups typically contain from 1 to 40 carbon atoms.
  • This invention provides fluorochemical compositions comprising a thermoplastic or thermoset polymer and at least one partially fluorinated piperazine sulfonamide compounds of Formulas I.
  • the present fluorinated piperazine sulfonamide compounds and compositions thereof provide the necessary performance even with the shorter C3-C5 perfluoroalkyl groups.
  • the short chain perfluorocarboxylic acids are less toxic and less
  • Rf groups are selected from C3-C5 perfluoroalkyl (and/or perfluoroalkylene) groups.
  • Rf is selected contains at least 95% linear perfluorobutyl groups and less than 5% of other perfluoroalkyl groups.
  • R 1 in compounds of Formulas I may be a linear or branched chain, saturated or unsaturated, cyclic or acyclic (or any combination thereof) alkyl or alkylene group having from 1 to 40 carbon atoms.
  • R 1 may contain aryl or arylene groups.
  • the range of structures contemplated for the organic moiety R 1 will be better understood with reference to the compounds suitable for use in steps of the Reaction Schemes described in detail below.
  • R 1 is an aryl group, including phenyl, napthyl, anthracenyl, phenanthanenyl, benzonapthanenyl, and fluorenyl.
  • the aryl group can be a polyvalent alkylene.
  • the aryl groups may be further substituted with one or more alkyl groups, i.e. an alkarylene group.
  • X 1 is a covalent bond and R 1 is an aryl group.
  • the fluoroaliphatic radical-containing piperazine compounds can be prepared using known organic reactions, such as those disclosed in US 5451622 (Boardman et al, incorporated herein by reference.
  • a preferred method of preparation is by the reaction of fluoroaliphatic radical-containing sulfonyl fluorides, RfSChF, with piperazine followed by reaction of the resulting fluoroaliphatic radical-containing sulfonylpiperazine with various organic reactants.
  • the perfluroalkylsulfonyl halide starting material is desirable prepared by electrochemical fluorination (ECF) of a linear C3-C5 sulfonyl fluoride, preferably a linear C 4 sulfonyl fluoride.
  • ECF electrochemical fluorination
  • the electrochemical fluorination yields a complex mixture of linear and branched isomers, as well as higher and lower homologues.
  • ECF of linear C3-C5 alkyl sulfonyl fluorides yields predominately linear products with minor amounts of homologues.
  • the present invention provides a synthetic organic polymer composition comprising the one or more of the fluorinated oligomers of Formulas I and/or II and a thermoplastic or thermoset organic polymer.
  • the compounds of Formula I are useful as polymer melt additives to impart desirable low surface energy properties to the thermoplastic or thermoset polymer.
  • molten additive (as a compound(s) or masterbatch) can be injected into a molten polymer stream to form a blend just prior to extrusion into the desired shaped article.
  • thermoset resins such as epoxy resins, urethanes and acrylates
  • the fluorochemical oligomer may be mixed with the resin and cured by application of heat.
  • thermoset resins may be processed by reactive extrusion techniques such as are taught in U.S. 4,619,976 (Kotnour) and U.S. 4,843,134 (Kotnour).
  • thermoplastic composition containing the compounds of Formula I may be used to provide oil and water repellency to fibers.
  • fluorochemical additives are melt processible, i.e., suffer substantially no degradation under the melt processing conditions used to form the fibers.
  • the amount of fluorochemical compound in the composition is that amount sufficient to produce a shaped article having a surface with the desired properties of oil and water repellency and/or soiling resistance.
  • the amount of fluorochemical compound will be that amount which provides from about 100 to 10,000 ppm fluorine, more preferably 200 to 5000 ppm, most preferably 400 to 3000 ppm fluorine, based on the weight of the shaped article.
  • Annealing may also be effected by contact with heated rolls, such as embossing rolls, at 50°C to 160°C for periods of about 1 to 30 seconds.
  • heated rolls such as embossing rolls
  • the annealing method may also serve to reduce the amount of additive necessary by maximizing fluorine content at the surface of the polymer.
  • the polymer composition of the invention is also useful in preparing blown microfibers for non-woven fabrics having low surface energy, oil and water repellency and/or soiling resistance.
  • the resin, such as polypropylene, used to form the melt blown microfibers should be substantially free from materials such as antistatic agents which could increase the electrical conductivity or otherwise interfere with the ability of the fibers to accept and hold electrostatic charges.
  • the fluorochemical compounds of the invention are used as additives to melt blown microfibers, the additive is preferably present in amounts of about 0.2 to 10 weight percent, more preferably from 0.5 to 5 weight percent and most preferably 0.5 to 2 weight percent.
  • the non-woven webs of fibers of thermoplastic olefinic polymer for use in this invention include non-woven webs manufactured by any of the commonly known processes for producing non-woven webs.
  • the fibrous non-woven web can be made by spunbonding techniques or melt-blowing techniques or combinations of the two.
  • Spunbonded fibers are typically small diameter fibers which are formed by extruding molten thermoplastic polymer as filaments from a plurality of fine, usually circular capillaries of a spinneret with the diameter of the extruded fibers being rapidly reduced.
  • melt blown polypropylene microfibers useful in the present invention can be prepared as described in Van Wente, A., "Superfine Thermoplastic Fibers," Industrial Engineering Chemistry, vol. 48, pp. 1342-1346 (1956) and in Report No. 4364 of the Naval Research Laboratories, published May 25, 1954, entitled “Manufacture of Super Fine Organic Fibers” by Van Wente et al. or from microfiber webs containing particulate matter such as those disclosed, for example, in U.S. Pat. Nos. 3,971,373 (Braun),
  • Multilayer constructions of nonwoven fabrics enjoy wide industrial and commercial utility and include uses such as fabrics for medical gowns and drapes.
  • the nature of the constituent layers of such multilayer constructions can be varied according to the desired end use characteristics, and can comprise two of more layers of melt-blown and spun-bond webs in may useful combinations such as described in U.S. Pat. Nos. 5,145,727 and 5,149,576.
  • the filtering efficiency of a melt-blown microfiber web can be improved by a factor of two or more when the melt-blown fibers are bombarded as they issue from the orifices with electrically charged particles such as electrons or ions, thus making the fibrous web an electret.
  • the web can be made an electret by exposure to a corona after it is collected.
  • Melt-blown polypropylene microfibers are especially useful, while other polymers may also be used such as polycarbonates and polyhalocarbons that may be melt-blown and have appropriate volume-resistivities under expected environmental conditions.
  • any of a wide variety of constructions may be made from the above- described fibers and fabrics, and such constructions will find utility in any application where some level of hydrophobicity, oleophobicity (or other fluid repellency, such as to bodily fluids) is required.
  • the fibers prepared from the synthetic organic polymer composition of the invention may be used in woven and nonwoven medical fabrics (such as drapes, gowns and masks), industrial apparel, outdoor fabrics (such as umbrellas, awning, tents, etc), raincoats and other outdoor apparel, as well as home furnishings such as table linens and shower curtains, and in myriad other related uses.
  • the filter media is annealed, i.e., heated for a sufficient time at a sufficient temperature to cause the fluorochemical additive to bloom to the surface of the fibers.
  • a sufficient temperature to cause the fluorochemical additive to bloom to the surface of the fibers.
  • about 1 to 10 minutes at about 140 deg. C. is sufficient although shorter times may be used at higher temperatures and longer times may be required at lower temperatures.
  • Blown microfibers for fibrous electret filters of the invention typically have an effective fiber diameter of from about 5 to 30 micrometers, preferably from about 7 to 10 micrometers, as calculated according to the method set forth in Davies, C. N., "The Separation of Airborne Dust and Particles," Institution of Mechanical Engineers, London, Proceedings IB, 1952.
  • the electret filter media of the present invention preferably has a basis weight in the range of about 10 to 500 g/m 2 , more preferably about 10 to 100 g/m 2 .
  • the basis weight can be controlled, for example, by changing either the collector speed or the die throughput.
  • the thickness of the filter media is preferably about 0.25 to 20 mm, more preferably about 0.5 to 2 mm.
  • the electret filter media and the polypropylene resin from which it is produced should not be subjected to any unnecessary treatment which might increase its electrical conductivity, e.g., exposure to gamma rays, ultraviolet irradiation, pyrolysis, oxidation, etc.
  • melt-blown microfibers or fibrillated fibers of the electret filters of the invention can be electrostatically charged by a process described in U.S. Pat. Nos. Re.
  • the charging process involves subjecting the material to corona discharge or pulsed high voltage.
  • Films prepared from the composition of this invention can be made which are useful, for example, for grease-resistant packaging, release liners and microporous film applications. These films can be used to make multi-layer constructions in which one, more than one, or all layers contain the fluorochemical additive.
  • KAYDOL Mineral Oil was obtained from Sonneborn, Inc., Parsippany, NJ under trade designation "KAYDOL” White Mineral Oil.
  • the Oil Repellency Test was run in the same manner as the Water Repellency Test described above except that the film samples were challenged to penetration by oil or oil mixtures of varying surface tensions.
  • the reported oil repellency rating corresponds to the oil or oil mixture for which the film sample passed the described test. It is desirable to have an oil repellency rating of at least 1 , preferably at least 3.
  • the oil repellency ratings and the corresponding oil or oil mixtures are shown in Table 2, below:
  • the extruder for PET used was a KraussMaffei Berstorff 25M1VI counter-rotating conical twin screw extruder (obtained from KraussMaffei Berstorff GmbH & Co., Kunststoff Germany) maximum extrusion temperature of approximately 275° C and with the distance to the collector of approximately 1 1 inches (about 28 cm).
  • the extruder used for Nylon-6 was a Leistritz 1 ⁇ i ⁇ ! counter-rotating conical twin screw extruder (obtained from Leistritz GmbH & Co., Nuremberg Germany) with maximum extrusion temperature of
  • the fluorochemical additive and thermoplastic polymer were each weighed and mixed in a plastic container in a desired ratio. Then using a mixer head affixed to a hand drill they were mixed for about one minute until a visually homogeneous mixture was obtained. This mixture was then added to the extruder hopper. The process conditions for each mixture were the same, including the film die construction and the thickness of the film (50 micrometers). The extrusion temperature was approximately 230-275° C depending on the polymer. The polymer throughput rate was about 7.5 Ibs/h (about 3.40 kg/h)
  • 1, 1,2,2,3, 3,4,4,4-nonafluorobutane-l-sulfonyl fluoride (500 mL, 2780 mmol) was added via addition funnel at such a rate so as to maintain a temperature below 90 °C. Upon completion of addition, the temperature was raised to 95 °C and the reaction mixture was allowed to stir for 16 h. The vessel was cooled to 50 °C, and water (300 mL) was added followed by dichloromethane (500 mL). The resulting biphasic mixture was allow to stir for 5 min and then allowed to phase separate. The lower phase was removed, washed 3x with water (300 mL), brine (500 mL) and dried over sodium sulfate (250g).
  • Benzene- 1,3, 5 -tricarbonyl chloride was slowly added via addition funnel to the reaction mixture with vigorous stirring. Upon completion, the mixture was allowed to stir for 16 h at r.t.. Water (300 mL) was then added to the white suspension and the product was collected via filtration.
  • EX1-EX9 either PET or a Nylon-6 polymer were co-extruded with a 1.5 wt. % fluorochemical additive prepared in PE2-PE10, respectively, using the process described above in Method for Forming Polymer Films.
  • the resulting films were annealed at 110 °C for 10 min (PET) or 120 °C for 20 min (Nylon-6).
  • CE10 was prepared in the same manner as EX1-EX9 described above except that C4F9S02N(CH3)CH2CH 2 OOC(CH2)i6COOCH2CH2(CH3)NS02C4F9 was the
  • CEl 1 was prepared in the same manner as EX1-EX9 described above, except that no fluorochemical additive was present.

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

Abstract

La présente invention concerne un nouveau composé sulfonamide pipérazine partiellement fluoré, et une composition polymère contenant le composé fluoré et un polymère thermoplastique ou thermodurcissable. La composition polymère est utile dans la préparation d'articles formés tels que des fibres et des films qui possèdent des propriétés hydrofuges et oléofuges souhaitables.
PCT/US2016/064079 2015-12-11 2016-11-30 Sulfonamides pipérazine fluorés WO2017100045A1 (fr)

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US201562266035P 2015-12-11 2015-12-11
US62/266,035 2015-12-11

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018169642A1 (fr) * 2017-03-17 2018-09-20 3M Innovative Properties Company Articles adhésifs et leurs procédés de fabrication
WO2018229596A1 (fr) * 2017-06-13 2018-12-20 3M Innovative Properties Company Composés d'additifs fondus, leurs procédés d'utilisation, articles et compositions les comprenant
US10590072B2 (en) 2016-09-09 2020-03-17 3M Innovative Properties Company Partially fluorinated aromatic esters
WO2020121248A1 (fr) 2018-12-12 2020-06-18 3M Innovative Properties Company Oxydes aminés tensioactifs fluorés
US10703940B2 (en) 2016-09-08 2020-07-07 3M Innovative Properties Company Adhesive article and method of making the same
US10731055B2 (en) 2016-11-15 2020-08-04 3M Innovative Properties Company Compound, adhesive article, and methods of making the same
US10731054B2 (en) 2016-06-29 2020-08-04 3M Innovative Properties Company Compound, adhesive article, and methods of making the same
WO2022144724A1 (fr) 2020-12-30 2022-07-07 3M Innovative Properties Company Sulfonamides partiellement fluorés destinés à être utilisés dans des films en pet

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US10731054B2 (en) 2016-06-29 2020-08-04 3M Innovative Properties Company Compound, adhesive article, and methods of making the same
US10703940B2 (en) 2016-09-08 2020-07-07 3M Innovative Properties Company Adhesive article and method of making the same
US10590072B2 (en) 2016-09-09 2020-03-17 3M Innovative Properties Company Partially fluorinated aromatic esters
US10731055B2 (en) 2016-11-15 2020-08-04 3M Innovative Properties Company Compound, adhesive article, and methods of making the same
WO2018169642A1 (fr) * 2017-03-17 2018-09-20 3M Innovative Properties Company Articles adhésifs et leurs procédés de fabrication
US10731056B2 (en) 2017-03-17 2020-08-04 3M Innovative Properties Company Adhesive articles and methods of making the same
US11028252B2 (en) 2017-06-13 2021-06-08 3M Innovative Properties Company Melt additive compounds, methods of using the same, and articles and compositions including the same
JP2020523350A (ja) * 2017-06-13 2020-08-06 スリーエム イノベイティブ プロパティズ カンパニー 溶融添加剤化合物、その使用方法、並びにそれを含む物品及び組成物
WO2018229596A1 (fr) * 2017-06-13 2018-12-20 3M Innovative Properties Company Composés d'additifs fondus, leurs procédés d'utilisation, articles et compositions les comprenant
JP7115718B2 (ja) 2017-06-13 2022-08-09 スリーエム イノベイティブ プロパティズ カンパニー 溶融添加剤化合物、その使用方法、並びにそれを含む物品及び組成物
WO2020121248A1 (fr) 2018-12-12 2020-06-18 3M Innovative Properties Company Oxydes aminés tensioactifs fluorés
WO2022144724A1 (fr) 2020-12-30 2022-07-07 3M Innovative Properties Company Sulfonamides partiellement fluorés destinés à être utilisés dans des films en pet
US11970595B2 (en) 2020-12-30 2024-04-30 3M Innovative Properties Company Partially fluorinated sulfonamide for use in PET films

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