US20140174461A1 - Surface Attachment of Particles to Cellulose Ester Fibers - Google Patents

Surface Attachment of Particles to Cellulose Ester Fibers Download PDF

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Publication number
US20140174461A1
US20140174461A1 US13/722,661 US201213722661A US2014174461A1 US 20140174461 A1 US20140174461 A1 US 20140174461A1 US 201213722661 A US201213722661 A US 201213722661A US 2014174461 A1 US2014174461 A1 US 2014174461A1
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United States
Prior art keywords
fibers
metal oxide
oxide particles
particles
cellulose ester
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Abandoned
Application number
US13/722,661
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English (en)
Inventor
Jeremy Kenneth Steach
Zhufang Liu
Charles Edwan Sumner, Jr.
Guy Ralph Steinmetz
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Eastman Chemical Co
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Eastman Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Chemical Co filed Critical Eastman Chemical Co
Priority to US13/722,661 priority Critical patent/US20140174461A1/en
Assigned to EASTMAN CHEMICAL COMPANY reassignment EASTMAN CHEMICAL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LIU, ZHUFANG, SUMNER, JR., CHARLES EDWAN, STEACH, Jeremy Kenneth, STEINMETZ, GUY RALPH
Priority to BR112015014449A priority patent/BR112015014449A2/pt
Priority to KR1020157019054A priority patent/KR20150096496A/ko
Priority to CA2892176A priority patent/CA2892176A1/en
Priority to JP2015549456A priority patent/JP2016507224A/ja
Priority to RU2015129485A priority patent/RU2015129485A/ru
Priority to PCT/US2013/074029 priority patent/WO2014099468A1/en
Priority to EP13814717.8A priority patent/EP2934201B1/en
Priority to MX2015006881A priority patent/MX2015006881A/es
Priority to CN201380066567.2A priority patent/CN104869852A/zh
Publication of US20140174461A1 publication Critical patent/US20140174461A1/en
Priority to US14/818,906 priority patent/US20150335065A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02—Manufacture of tobacco smoke filters
    • A24D3/0204—Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212—Applying additives to filter materials
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/02—Manufacture of tobacco smoke filters
    • A24D3/0204—Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212—Applying additives to filter materials
    • A24D3/022—Applying additives to filter materials with liquid additives, e.g. application of plasticisers
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/067—Use of materials for tobacco smoke filters characterised by functional properties
    • A24D3/068—Biodegradable or disintegrable
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
    • A24D3/10—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent of cellulose or cellulose derivatives
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/16—Use of materials for tobacco smoke filters of inorganic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/10—Esters of organic acids, i.e. acylates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/10—Esters of organic acids, i.e. acylates
    • C08L1/12—Cellulose acetate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/10—Esters of organic acids, i.e. acylates
    • C08L1/14—Mixed esters, e.g. cellulose acetate-butyrate

Definitions

  • the invention generally relates to a method of attaching particles, such as metal oxides, to the surface of cellulose ester fibers.
  • Typical cigarette filters are made from a continuous-filament tow band of cellulose acetate-based fibers, called cellulose acetate tow, or simply acetate tow.
  • cellulose acetate tow a continuous-filament tow band of cellulose acetate-based fibers
  • simply acetate tow a continuous-filament tow band of cellulose acetate-based fibers.
  • the use of acetate tow to make filters is described in various patents, and the tow may be plasticized. See, for example, U.S. Pat. No. 2,794,239.
  • the conversion of acetate tow into cigarette filters may be accomplished by means of a tow conditioning system and a plugmaker, as described, for example, in U.S. Pat. No. 3,017,309.
  • the tow conditioning system withdraws the tow from the bale, spreads and de-registers (“blooms”) the fibers, and delivers the tow to the plugmaker.
  • the plugmaker compresses the tow, wraps it with plugwrap paper, and cuts it into rods of suitable length.
  • a non-volatile solvent may be added to solvent-bond the fibers together.
  • solvent-bonding agents are called plasticizers in the trade, and historically have included triacetin (glycerol triacetate), diethylene glycol diacetate, triethylene glycol diacetate, tripropionin, acetyl triethyl citrate, and triethyl citrate. Waxes have also been used to increase filter firmness. See, for example, U.S. Pat. No. 2,904,050.
  • plasticizer bonding agents work well for bonding and selective filtration.
  • plasticizers typically are not water-soluble, and the fibers will remain bonded over extended periods of time.
  • conventional cigarette filters can require years to degrade and disintegrate when discarded, due to the highly entangled nature of the filter fibers, the solvent bonding between the fibers, and the inherent slow degradability of the cellulose acetate polymer. Attempts have, therefore, been made to develop cigarette filters having improved degradability.
  • degradable cellulose ester fibers such as those used in cigarette filters, and especially those that may be fabricated without using plasticizers or having reduced entanglement when wet.
  • the present invention provides a method of attaching metal oxide particles to the surface of cellulose ester fibers.
  • the method comprises contacting cellulose ester fibers with a mixture comprising metal oxide particles dispersed in a protic liquid to attach the metal oxide particles on the surface of the fibers.
  • the mixture is substantially free of plasticizer.
  • the invention provides for cellulose ester fibers made by the method according to the invention.
  • the invention provides for a cigarette filter which comprises the cellulose ester fibers made by the method according to the invention.
  • FIG. 1 shows an image from a scanning electron microscope (SEM) of the TiO 2 particles attached to the cellulose acetate fiber surface from Example 1.
  • SEM scanning electron microscope
  • FIG. 2 shows an image from a SEM of the ZnO particles attached to the cellulose acetate fiber surface from Example 2.
  • particles such as metal oxides, may be attached to the surface of cellulose ester fibers without the use of a plasticizer.
  • the present invention provides a method of attaching metal oxide particles to the surface of cellulose ester fibers.
  • the method comprises contacting cellulose ester fibers with a mixture comprising metal oxide particles dispersed in a protic liquid to attach the metal oxide particles on the surface of the fibers.
  • the mixture is substantially free of plasticizer.
  • plasticizer is intended to describe a solvent that, when applied to cellulose ester fibers, solvent-bonds the fibers together.
  • plasticizers include triacetin (glycerol triacetate), diethylene glycol diacetate, triethylene glycol diacetate, tripropionin, acetyl triethyl citrate, triethyl citrate, and mixtures thereof with one or more polyethylene glycols.
  • substantially free it is meant that a plasticizer is not present in an amount that appreciably hinders the rate of degradation of the cellulose ester fibers compared to the rate of fiber degradation in the absence of the plasticizer.
  • the mixture is free of plasticizer.
  • the metal oxide particles that may be used in the present invention is not particularly limiting.
  • the metal of the metal oxide may be selected from Groups 1-16 of the Periodic Table of Elements.
  • Preferred metals for the metal oxides include titanium, zinc, and aluminum.
  • the metal oxides may be mono-metal or mixed metal oxides, such as a bimetal oxide.
  • a preferred class of metal oxides particles includes those that are photoactive agents.
  • photoactive agent refers to an agent that, when applied to a cellulose ester fiber, increases the rate at which the fiber degrades upon exposure to UV radiation.
  • Photoactive agents useful according to the invention include titanium dioxides, although other photoactive metals or metal compounds may likewise be used.
  • the titanium dioxide particles may be in rutile or anatase form, or a mixture of the two crystalline forms in the same particle.
  • the amount of anatase phase present in the mixed-phase particles may vary, for example, from 2 to 98 wt %, from 15 to 95 wt %, or from 50 to 95 wt %, as measured using x-ray diffraction techniques.
  • the rutile phase in the mixed-phase particles may likewise vary in a similar manner, for example, from 2 to 98 wt %, from 15 to 95 wt %, or from 50 to 95 wt %, as measured using x-ray diffraction techniques. These mixed-phase particles are especially suitable at enhancing fiber degradation.
  • the titanium dioxide particles may be prepared by a variety of methods known in the art, including high-temperature hydrolysis.
  • the particles may also be obtained commercially.
  • the metal oxide particles for use in the present invention may vary in size, for example, from 1 nm to 50 microns in diameter.
  • Preferred metal oxide particle diameters include, for example, from 1 nm to 250 nm and from 5 to 50 nm.
  • the surface area of the metal oxide particles may also vary over a wide range, such as, for example, from 1 to 400 m 2 /g, as measured by the BET surface area method.
  • the particles Preferably, have a surface area in the range of, for example, 10 to 300 m 2 /g or 10 to 150 m 2 /g.
  • the protic liquid for use in the present invention may be any compound that has a hydrogen atom bonded to an oxygen, provided that it does not dissolve the cellulose ester fibers.
  • Examples of protic liquids include water, most alcohols, formic acid, and acetic acid. Water, lower alcohols (e.g., those containing C 1 -C 4 ), and mixtures thereof are preferred protic liquids.
  • Examples of the lower alcohols include methanol, ethanol, isopropanol, and n-butanol.
  • the mixture comprising metal oxide particles dispersed in the protic liquid may be prepared in any matter.
  • the metal oxide particles may be added to the protic liquid, and the mixture may be shaken, stirred, or sonicated to disperse the particles in the liquid.
  • the amount of metal oxide particles dispersed in the protic liquid may vary over a wide range.
  • the mixture may contain from 1 to 1,000 ppm of the metal oxide particles.
  • the mixture may contain from 10 to 500 ppm of the metal oxide particles.
  • the cellulose ester fibers are brought into contact with the mixture for a sufficient amount of time for the particles to deposit or attach themselves on the surface of the fibers.
  • the contact time may vary over a wide range, for example, from 1 second to 1 hour.
  • the contacting step may be carried out in any manner.
  • the fibers may be dipped into the mixture and allowed to soak for a desired amount of time.
  • the fibers may be pulled through the mixture until a desired amount of particles are deposited on the fibers.
  • cellulose ester fiber means a fiber formed from one or more cellulose esters, such as cellulose acetate, for example, by melt-spinning or solvent-spinning.
  • the cellulose esters useful in the present invention include cellulose acetates, cellulose propionates, and cellulose butyrates with varying degrees of substitution, as well as mixed esters of these, e.g., cellulose acetate propionate, cellulose acetate butyrate, and cellulose acetate propionate butyrate.
  • the cellulose ester may be a secondary cellulose ester. Examples of suitable cellulose esters include those described in U.S. Pat. Nos. 1,698,049; 1,683,347; 1,880,808; 1,880,560; 1,984,147; 2,129,052; and 3,617,201; the entire contents of which are hereby incorporated by reference.
  • cigarette filters are traditionally made with cellulose acetate fibers, the invention is not limited to traditional esters or to cigarette filters.
  • the typical degree of substitution per anhydroglucose unit (DS/AGU) of acetate for cigarette filters is about 2.45
  • filters may be readily constructed with a range of acetyl levels, such as from 1.5 to 2.8, or from 1.8 to 2.7, or from 1.9 to 2.5, or for example, an average DS/AGU of about 2.0. Lower DS/AGU values may provide faster degradation.
  • the cellulose ester can be spun into fiber, for example, by melt-spinning or by spinning from an appropriate solvent (e.g., acetone, acetone/water, tetrahydrofuran, methylene chloride/methanol, chloroform, dioxane, N,N-dimethylformamide, dimethylsulfoxide, methyl acetate, ethyl acetate, or pyridine).
  • an appropriate solvent e.g., acetone, acetone/water, tetrahydrofuran, methylene chloride/methanol, chloroform, dioxane, N,N-dimethylformamide, dimethylsulfoxide, methyl acetate, ethyl acetate, or pyridine.
  • solvent e.g., acetone, acetone/water, tetrahydrofuran, methylene chloride/methanol, chloroform, dioxane, N,N-dimethylformamide, dimethyls
  • the spinning solvent can be acetone containing less than 3 wt % water.
  • the spinning solvent can be acetone containing 5-15 wt % of water.
  • the spinning solvent can be acetone containing 15-30 wt % of water.
  • the cellulose ester may have a melt temperature, for example, from 120° C. to 250° C., or from 180° C. to 220° C.
  • the cellulose ester fibers for use in the present invention may be continuous fibers, or may be staple fibers having a shorter length, rendering the fibers more susceptible to degradation.
  • the staple fibers may have a length from 3 to 10 mm, or from 4 to 8 mm.
  • the staple fibers may likewise be randomly oriented.
  • the cellulose ester fibers may be crimped and have, for example, from 4-20 crimps per inch, or from 10 to 15 crimps per inch.
  • the fibers may have a denier/filament (DPF), for example, of 20-0.1, or from 5-1.5 DPF.
  • DPF denier/filament
  • the fibers may optionally contain lubricants or processing aids such as mineral oil, used in an amount from 0.1 to 3%, or from 0.3 to 0.8% by weight.
  • liquid on the surface of the fibers may be removed.
  • This optional removal step may be performed in any manner.
  • the excess liquid may be allowed to drain off of the fibers.
  • the excess liquid may also be wiped off or pressed off of the fibers.
  • the excess liquid may also be removed by evaporation, optionally at elevated temperature such as in an oven at 50 to 100° C. Any of these techniques may be used in combination to remove excess liquid from the fibers.
  • the fibers may optionally be removed.
  • the excess or unattached particles may be removed by any manner.
  • the fibers may be contacted with a protic liquid without metal oxide particles or with a lower concentration of metal oxide particles than the original treating mixture.
  • the excess particles may also be removed by motion, such as centrifugal or vibratory. Any of these techniques may be used in combination to remove excess, loosely attached, or unattached particles from the fibers, if desired.
  • the fibers may be dried to produce finished fibers with metal oxide particles attached to their surface. Residual liquid in the fibers may be removed in this step.
  • the drying step may be performed in any matter. Preferably, the fibers are dried in an oven at elevated temperatures such as from 50 to 150° C.
  • the metal oxide particles may be attached to the surface of the fibers using the method of the invention.
  • the finished fibers may contain from 0.01 to 10 wt % of metal oxide particles, while other amounts are possible.
  • the invention relates to cellulose ester fibers prepared using the method of the invention.
  • the fibers are free of plasticizer.
  • the fibers produced according to the invention are particularly useful in cigarette filters.
  • the fibers according to the invention may be formed into cigarette filters according to methods known in the art.
  • the cellulose acetate fiber samples with surfaced attached metal oxide particles were prepared by weighing 1 gram of cellulose acetate tow. A 0.01% w/w mixture of metal oxide particles in a protic liquid was prepared. The mixture was sonicated for 30 minutes to disperse the particles in the liquid. The cellulose acetate tow with no additive was added to the mixture and allowed to soak for 30 minutes. Tow samples were removed from the dispersion, and the excess water was drained off the sample. The tow was then transferred to a 75° C. oven. The samples were left in the oven for 1 hour. After 1 hour, the samples were removed from the oven and placed in deionized H 2 O.
  • the samples were sonicated for 30 minutes so as to remove excess or unattached particles from the surface of the cellulose acetate fibers. After sonicating, the fibers were transferred to an oven at 100° C. The cellulose acetate tow was left in the oven until dry.
  • Evonik/Degussa P25 TiO 2 particles were dispersed in Nanopure H 2 O (18M ⁇ .cm) and attached to the surface of cellulose acetate fibers according to the general procedures described above.
  • the P 25 TiO 2 particles were an ultrafine-size, uncoated mixed-phase TiO 2 having an average particle size of about 20 nm.
  • FIG. 1 shows an image from a scanning electron microscope (SEM) of the P25 TiO 2 particles attached to the cellulose acetate fiber surface from Example 1.
  • ZnO particles were dispersed in isopropanol and attached to the surface of cellulose acetate fibers according to the general procedures described above.
  • the ZnO particles were obtained from Aldrich and had an average particle size of less than 1 micron.
  • FIG. 2 shows an image from a SEM of the ZnO particles attached to the cellulose acetate fiber surface from Example 2.
  • Acetate tow was made with cellulose acetate fibers containing no pigment in the fibers.
  • the weathering results are shown in Table 1.
  • Acetate tow was made with cellulose acetate fibers containing pigment size ( ⁇ 200 nm) and coated TiO 2 particles (Kronos 1071) in the fibers. This example was prepared to understand the effect of size and coating of the TiO2 on photodegradation. The weathering results are shown in Table 1.
  • Acetate tow was made with cellulose acetate fibers containing no pigment in the fibers with photoactive TiO 2 particles (Degussa Evonik P25) attached to the fiber surface using the general procedures described above.
  • the TiO 2 particles used in this example were an ultrafine size and uncoated mixed-phase TiO 2 .
  • the weathering results are shown in Table 1.
  • Acetate tow was made with cellulose acetate fibers containing pigment size ( ⁇ 200 nm) and coated TiO 2 (Kronos 1071) in the fibers with photoactive TiO 2 particles (Degussa Evonik P25) attached to the fiber surface using the general procedures described above.
  • the TiO 2 particles used in this example were an ultrafine size and uncoated mixed-phase TiO 2 .
  • This example was prepared to understand the effect of size and coating of the TiO 2 particles on photodegradation, and how photoactive TiO 2 on the surface can change the rate of photodegradation.
  • the weathering results are shown in Table 1.
  • Example 3 displayed a weight loss of 33%, while Example 5 showed a 67% weight loss.
  • Example 4 displayed a weight loss of 15%, while Example 6 had a weight loss of 60%.
  • Cellulose acetate fiber samples with surfaced attached particles were prepared according to the general procedures described above to determine the stability of the particles on the fiber surface.
  • Four fiber samples were prepared with TiO 2 particles, while another four fiber samples were prepared with ZnO particles.
  • the surface-attached fiber samples were placed in individual beakers of water and placed in a sonicator. The samples were then sonicated up to 5 hours. The samples were then analyzed by ICP-OES to determine Zn and Ti content on the fibers. The results of the ICP-OES analysis for the sonicated samples are shown in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pens And Brushes (AREA)
US13/722,661 2012-12-20 2012-12-20 Surface Attachment of Particles to Cellulose Ester Fibers Abandoned US20140174461A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US13/722,661 US20140174461A1 (en) 2012-12-20 2012-12-20 Surface Attachment of Particles to Cellulose Ester Fibers
CN201380066567.2A CN104869852A (zh) 2012-12-20 2013-12-10 颗粒至纤维素酯纤维的表面附着
JP2015549456A JP2016507224A (ja) 2012-12-20 2013-12-10 セルロースエステル繊維に対する粒子の表面付着
KR1020157019054A KR20150096496A (ko) 2012-12-20 2013-12-10 셀룰로스 에스터 섬유에 대한 입자의 표면 결합
CA2892176A CA2892176A1 (en) 2012-12-20 2013-12-10 Surface attachment of particles to cellulose ester fibers
BR112015014449A BR112015014449A2 (pt) 2012-12-20 2013-12-10 método para afixar partículas de óxido de metal na superfície das fibras de éster de celulose, fibras de éster de celulose, e, filtro de cigarro
RU2015129485A RU2015129485A (ru) 2012-12-20 2013-12-10 Поверхностное присоединение частиц к волокнам из сложного эфира целлюлозы
PCT/US2013/074029 WO2014099468A1 (en) 2012-12-20 2013-12-10 Surface attachment of particles to cellulose ester fibers
EP13814717.8A EP2934201B1 (en) 2012-12-20 2013-12-10 Surface attachment of particles to cellulose ester fibers
MX2015006881A MX2015006881A (es) 2012-12-20 2013-12-10 Union superficial de particulas a fibras de ester de celulosa.
US14/818,906 US20150335065A1 (en) 2012-12-20 2015-08-05 Surface attachment of particles to cellulose ester fibers

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US13/722,661 US20140174461A1 (en) 2012-12-20 2012-12-20 Surface Attachment of Particles to Cellulose Ester Fibers

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US14/818,906 Abandoned US20150335065A1 (en) 2012-12-20 2015-08-05 Surface attachment of particles to cellulose ester fibers

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EP (1) EP2934201B1 (zh)
JP (1) JP2016507224A (zh)
KR (1) KR20150096496A (zh)
CN (1) CN104869852A (zh)
BR (1) BR112015014449A2 (zh)
CA (1) CA2892176A1 (zh)
MX (1) MX2015006881A (zh)
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WO (1) WO2014099468A1 (zh)

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WO2017027213A1 (en) * 2015-08-07 2017-02-16 Eastman Chemical Company Metal-organic framework for fluid stream filtration applications

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CN108610506B (zh) * 2018-04-26 2020-09-22 浙江理工大学 一种一体成型的环保防护垫及其生产方法

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US20130213421A1 (en) * 2012-02-16 2013-08-22 R. J. Reynolds Tobacco Company Apparatus and associated method for forming a filter component of a smoking article

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KR20150096496A (ko) 2015-08-24
EP2934201A1 (en) 2015-10-28
JP2016507224A (ja) 2016-03-10
CN104869852A (zh) 2015-08-26
RU2015129485A (ru) 2017-01-25
BR112015014449A2 (pt) 2017-07-11
EP2934201B1 (en) 2016-09-21

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