US2980554A - Non-fibrous regenerated cellulose film containing anchoring-plasticizing agent - Google Patents

Non-fibrous regenerated cellulose film containing anchoring-plasticizing agent Download PDF

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US2980554A
US2980554A US78927159A US2980554A US 2980554 A US2980554 A US 2980554A US 78927159 A US78927159 A US 78927159A US 2980554 A US2980554 A US 2980554A
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film
agents
anchoring
regenerated cellulose
cellulose film
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Expired - Lifetime
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Anthony J Gentile
Porter Clemmon
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority to NL247796D priority Critical patent/NL247796A/xx
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US78927159 priority patent/US2980554A/en
Priority to GB123460A priority patent/GB881801A/en
Priority to FR816232A priority patent/FR1245448A/fr
Priority to BE589296A priority patent/BE589296A/fr
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Publication of US2980554A publication Critical patent/US2980554A/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/06—Coating with compositions not containing macromolecular substances
    • C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/06—Cellulose hydrate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31971—Of carbohydrate
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31971—Of carbohydrate
    • Y10T428/31975—Of cellulosic next to another carbohydrate
    • Y10T428/31978—Cellulosic next to another cellulosic
    • Y10T428/31986—Regenerated or modified

Definitions

  • the present invention relates to non-fibrous regenerated cellulose film uniformly impregnated with a dior polysubstituted water-soluble higher nitrogen-base compound as combined ancho'ring-plasticizing agent for subsequently applied topcoat material.
  • the invention includes methods for applying the anchoring-plasticizing agent to the film and further includes the treated cellulose film with and without the topcoat.
  • Non-fibrous regenerated cellulose film i.e., uncoated dry film containing no modifying or treating agent
  • Such film is therefore usually impregnated with a humectant (e.g., glycerol) which acts as a plasticizer.
  • a humectant e.g., glycerol
  • the resulting film is valuable as a wrap.
  • Such film is permeable to water-vapor and is therefore not suitable for wrapping moisture-sensitive products and foods.
  • cellulose film which contains glycerol as plasticizer can be rendered impervious to water by coating it with hydrophobic topcoat material.
  • topcoat material tends to slough from such film in the presence of water, and to prevent this it is customary to pretreat the film with an anchoring agent (usually an aminealdehyde resin).
  • an anchoring agent usually an aminealdehyde resin
  • the anchoring agent is dissolved in the glycerol bath and the film is thus impregnated with the two materials together.
  • the general process is disclosed in Pollard US. Patent No. 2,394,009 granted February 5, 1946.
  • the anchoring agent is generally substantive to cellulose whereas the plasticizer is not, so that the two materials exhaust from the bath at different rates.
  • the bath therefore requires periodic chemical analysis and the separate metering of two different agents.
  • non-fibrous regenerated cellulose film containing a water-soluble com.- pound from the group consisting of amides and amines containing at least 6 lower 'alkyleneoxy groups and at least one hydrophobic substituent of at least 6 carbon atoms are both plasticized and provided with a content of anchoring agent for subsequently applied hydrophobic topcoat material.
  • the compounds have thus been found to serve a double purpose when present in cellulose film.
  • amides includes thioureas, ureas, carbazides, and semi-carbizides.
  • the term amines includes amidines, guanidines, oximes, and ammonium quaternaries.
  • the invention possesses a numberof substantial advantages.
  • v(l) It permits one compound tobe used in place of two, and thus permits elimination of the necessity for maintaining a balance between separately added plasticizing and anchoring agents in the filrn treating bath, and the handling of two different agents.
  • the agents need not contain formaldehyde, and thus are comparatively odorless.
  • the film of the presout invention is thus particularly suited for wrapping foods of delicate flavor, such as cheese.
  • nonfibrous regenerated cellulose film is impregnated with an aqueous solution of one or more of the agents described below, withdrawn, and stripped of excess or free solution in any convenient way, after which the film, now containing the anchoring-plasticizing agent, may be dried and used, or topcoated with or without drying as dictated by the characteristics of the topcoating composi tion.
  • the agents of the present invention are generally effective over a wide pH range so that there is usually no need to control the pH of the bath within narrow limits. It is a feature of the invention, however, that the agents are effective in the range pH 6-pH 8, so that substantially neutral cellulose film can be produced. Such film does not undergo acid tendering and is consequently more desirable.
  • the bath may contain more than one of the agents of the present invention so long as they are generally mutually compatible. Incompatibility is evidenced by precipitation upon admixture.
  • the bath may contain other agents commonly used in the treatment of non-fibrous regenerated cellulose film: for example,
  • the bath may contain a methylolcarbamyl polyazaialkane resin of Jen et al. US. Patent No. 2,764,507, granted on September 25, 6; a fire retardant mixture, for example diammonium phosphate and dicyandiamide as shown in Wooding et al. US. Patent No. 2,757,102, granted on July 13, 1956; a dye; ora scent.
  • water repellent topcoats which may be used are nitrocellulose, cellulose acetate, methyl cellulose, polyethylene, deacetylated chitin, rubber, chlorinated rubber, rubber hydrochloride, ethyl cellulose, butyl methacrylate, moisture-resistant lacquers, waxes such as montan wax, beeswax, carnauba wax and other conventional film-forming waterproofing materials.
  • the topcoat is not necessarily a continuous film, and may and often does consist of printed legends, revenue stamps, or decorative matter.
  • topcoat material is generally applied in the form of a solution in an organic solvent and in such event the film is dried to normal water content before application of the topcoat solution.
  • the topcoat may be applied by fusing molten thermoplastic resin material thereover, for example molten polyethylene, in which case thev film is likewise dried beforehand. Where the topcoat is applied in the form of a latex or emulsion, however, this preliminary drying is not necessary.
  • plasticization and anchoring effect imparted by eachincrement of agent is pronounced when the agent is present in the film in the range of %-15% by weight. Thereafter the increase in plasticization and anchoring tends to level off and the upper economic limit is generally reached when the film contains 25%35% by weight of agent.
  • Our preferred concentration of agent in the film is accordingly between about and based on the dry weight of the film, corresponding to the amount picked up by the film when impregnated to saturation with a solution containing 5% to 10% by weight of the agent.
  • the hydrophobic substituents present in the treating agents may be hydrocarbon substituents such as aryl, alkyl, aralkyl, and alkaryl groups containing more than 6 carbon atoms, or chlo-roalkyl, chloroaryl substituents, or ester substituents.
  • hydrocarbon substituents such as aryl, alkyl, aralkyl, and alkaryl groups containing more than 6 carbon atoms, or chlo-roalkyl, chloroaryl substituents, or ester substituents.
  • the lower alkyleneoxy groups also present in the treating agents contain not more than 4 carbon atoms each and are such as are formed by condensation of a parent amide or amine with a lower alkylene oxide (e.g., ethylene oxide or propylene oxide) or with a lower chlorohydrin (e.g., epichlorohydrin).
  • a parent amide or amine e.g., ethylene oxide or propylene oxide
  • a lower chlorohydrin e.g., epichlorohydrin
  • the number of alkyleneoxy groups introduced should be sufiicient to confer at least some water-solubility, for example 5%.
  • water-soluble as applied to the treating agents of the present invention, in cludes agents which are self-dispersi'ble in water forming cloudy colloidal solutions having the appearance of soap solutions, as well as agents which form clear solutions in water.
  • Anchor-plasticizing agents suitable for use in the present invention may be prepared by a variety of methods and the invention does not depend upon the particular method which is selected.
  • carboxamide-type agents may be prepared by reacting a higher fatty acid nitrogen- Z-hydroxyethylamide with sufiicient alkylene oxide, at least 6 mols, to produce solubility.
  • An example of this is the reaction of N-Z-hydroxyethyl stearamide with 20 mols of ethylene oxide.
  • Amidine-type agents may be prepared by direct reaction of an alkylene oxide or epichlorohydrin upon a higher fatty guanamine, a melamine which has been reacted with a higher fatty acid chloride, or a higher fatty acid substituted urea, thiourea, guanidine, biguanamide, biuret, or dicyandiamide.
  • a further class of suitable treating agents may be prepared by reacting an appropriately substituted sulfonamide with a lower alkylene oxide.
  • Anchoring-plasticizing agents according to the invention can further 'be prepared from high molecular weight polymers.
  • agents having a polyalkylenepolyamine structure can be prepared by partially reacting polyethylenimine with a higher fatty chloride or acid chloride and then reacting the resulting amine or amine-amide with ethylene oxide.
  • Additional agents may be prepared by polymerizing a vinyl amide, for example acrylamide and methacrylamide, alone or with a vinyl compound copolymerizable therewith, partially reacting the polymer with a higher fatty acid chloride and then further reacting with an alkylene oxide, and by reacting a heterocyclic amine, for example 2-dodecylpyridine with ethylene oxide in necessary amount.
  • Treating agents of the quaternary ammonium type may be prepared by reacting a quaternary ammonium compound containing the necessary hydrophobic substituent and a hydroxyl group with ethylene oxide.
  • a quaternary ammonium compound containing the necessary hydrophobic substituent and a hydroxyl group may be reacted with ethylene oxide.
  • phydroxyphenyl trimethyl ammonium chloride may be reacted with ethylene oxide.
  • a tertiary amine may be reacted under acid conditions with ethylene oxide.
  • the ethylene oxide combines directly with the nitrogen atom thereby quaternarizing it.
  • the product starting from N,N-dimethylamine and using hydrochloric acid as the catalyst, is dimethyloctadecyl hydroxy (polyoxyethyl) ammonium chloride.
  • agents containing alkyleneoxy groups in each molecule so that there does not appear to be any maximum to the number thereof which may be present.
  • agents which contain more than 20 such groups per molecule This number of groups generally avoids the danger of the presence of too few and appears to enhance or fortify the plasticizing action of the hydrophobic organic group or groups.
  • the anchoring agents which contain one or more aldehyde-reactive NH-- substituents may be reacted by known means with formaldehyde to yield metholated anchor-plasticizing agents which thermoset when heated at film drying temperatures. Film containing one or more of such modified agents is within the scope of the present invention.
  • the molecular weights of the treating agents while considerable, need not be of polymeric magnitude and we have achieved very satisfactory plasticization and anchoring by the use of agents having molecular weights no greater than 600.
  • laboratory evidence indicates that high molecular weight compounds are more permanent in the properties they impart since they display less tendency to migrate when the treated film is pressed against other material in which the agent is soluble.
  • Our evidence indicates that treating agents having molecular weights in excess of 5000 are more permanent for this reason and, where permanence is of chief importance, such agents are therefore preferred.
  • the invention is illustrated by the drawing, which is a schematic vertical section of non-fibrous regenerated cellulose film containing an anchoring-plasticizing agent a water-soluble compound selected from the group consisting of the amides and amines containing at least one hydrophobic substituent of at least 6 carbon atoms and at least 6 lower alkyleneoxy groups.
  • the film carries an optional hydrophobic topcoat.
  • Example I The manufacture and testing of non-fibrous regenerated cellulose film containing a variety of the anchoringplasticizing agents described above is illustrated by the following.
  • the agents were prepared by reacting a parent amine or amide, as shown in the table below, with 6 or more mols of an alkylene oxide.
  • a series of anchoring-plasticizing baths was prepared by dissolving the agents in laboratory demineralized water and adjusting the pH to the value shown. Except as indicated in the table, dilute aqueous sodium hydroxide or hydrochloric acid was used for this adjustment.
  • the baths when viewed in bulk, ranged in appearance from clear to quite cloudy and their color ranged between water-white and light amber.
  • Sheets of wet swollen washed regenerated cellulose film were immersed in the baths for 5 minutes at room temperature, hung to allow excess bath liquid to drain off, clamped to wooden frames to prevent shrinkage, and oven dried at 200 C. for 10 minutes. The sheets were then removed from the frames. They were water-clear, flexible and odorless.
  • the flexibility of the sheets was determined using as the reference standard a sheet of non-fibrous regenerated cellulose film containing 16% by weight of glycerol as plasticizer. The comparisons were made manually, a rating of 0 indicating no plasticization and a rating of 3 indicating plasticization equal to the glycerol standard. Ratings of 1 and 2 were given to sheets of intermediate plasticity and the rating of 4 was given to sheets which were better plasticized then the sample. The plasticity values obtained are shown in the table below.
  • the films were then topcoated by dipping into a standard nitrocellulose topcoat lacquer solution prepared as described in US. Patent No. 2,394,009, drained, and oven-dried at 200 F. for the times shown in the table below, three minutes at that temperature being about the minimum necessary to dry the topcoat.
  • Strips were cut from the resulting topcoated films, all edges of the strips being freshly cut, and the strips immersed in water at 190 F. Resistance to sloughing was determined by rubbing the films which contained one of the anchoring resins every two to four minutes between the fingers and averaging the results.
  • Non-fibrous regenerated cellulose film containing as anchoring-plasticizing agent a water-soluble compound Results are shown in the table below. selected from the group consisting of the amides and Anchor-Plasticizing Agent Bath Film Topcoat Run Flexi- Mins. to N0. Mols Per- Stab. bility 8 Slough Parent Amine or Amide Et O Kent pH C.
  • Example 2 The pronounced decrease in viscosity of the treating bath produced by moderate elevation of temperature is illustrated by the following.
  • the plasticizing agent is the ammonium quaternary formed 7 by reacting dimethyl (octadecylamidopropyl) amine with 10 to 100 mols of ethylene oxide.
  • Film according to claim 1 having a pH between 6 and 8.
  • Non-fibrous regenerated cellulose film containing as anchoring-plasticizing agent a water-soluble amide containing at least 6 lower alkyleneoxy groups and at least one hydrophobic substituent of at least 6 carbon atoms.
  • Non-fibrous regenerated cellulose film containing as anchoring-plasticizing agent a water-soluble amine containing at least 6 lower alkyleneoxy groups and at least one hydrophobic substituent of at least 6 carbon atoms.
  • Non-fibrous regenerated cellulose film containing as anchoring-plasticizing agent a water-soluble ammonium quaternary containing at least 6 lower alkyleneoxy groups and at least one hydrophobic substituent of at least 6 carbon atoms.
  • Non-fibrous regenerated cellulose film containing as anchoring-plasticizing agent of a water-soluble compound selected from the group consisting of amides and amines containing at least 6 lower alkyleneoxy groups and at least one hydrophobic substituent of at least 6 carbon atoms and carrying hydrophobic topcoat material on at least one side thereof.
  • a process for the manufacture of non-fibrous regenerated cellulose film which comprises passing said film into an aqueous bath containing as anchoringplasticizing agent a water-soluble compound selected from the group consisting of, amides and amines containing at least 6 alkyleneoxy groups and at least one hydrophobic hydrocarbon substituent of at least 6 carbon atoms, thereby impregnating said film with said agent, and drying said film.
  • a process for the manufacture of non-fibrous regenerated cellulose film which comprises impregnating said film with an aqueous bath containing as anchoringplasticizing agent a water-soluble compound selected from the group consisting of water-soluble amides and amines containing at least 6 alkyleneoxy groups and at least one hydrophobic hydrocarbon substituent of at least 6 carbon atoms, and applying hydrophobic organic topcoat material to at least one side thereof.

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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)
  • Laminated Bodies (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
US78927159 1959-01-27 1959-01-27 Non-fibrous regenerated cellulose film containing anchoring-plasticizing agent Expired - Lifetime US2980554A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL247796D NL247796A (enrdf_load_stackoverflow) 1959-01-27
US78927159 US2980554A (en) 1959-01-27 1959-01-27 Non-fibrous regenerated cellulose film containing anchoring-plasticizing agent
GB123460A GB881801A (en) 1959-01-27 1960-01-13 Non-fibrous regenerated cellulose film and process of manufacture
FR816232A FR1245448A (fr) 1959-01-27 1960-01-21 Films de cellulose régénérée imprégnés et procédé pour les fabriquer
BE589296A BE589296A (fr) 1959-01-27 1960-04-01 Films de cellulose régenérée impregnes et procédé pour les fabriquer.

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US78927159 US2980554A (en) 1959-01-27 1959-01-27 Non-fibrous regenerated cellulose film containing anchoring-plasticizing agent

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BE (1) BE589296A (enrdf_load_stackoverflow)
FR (1) FR1245448A (enrdf_load_stackoverflow)
GB (1) GB881801A (enrdf_load_stackoverflow)
NL (1) NL247796A (enrdf_load_stackoverflow)

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316120A (en) * 1966-06-03 1967-04-25 American Cyanamid Co Process for preparing topcoated plasticized non-fibrous regenerated cellulose film and the resultant product
US3447948A (en) * 1965-09-02 1969-06-03 Fmc Corp Resin coated cellulosic sheet having reduced tendency to accumulate an electrostatic charge
US3505072A (en) * 1969-06-09 1970-04-07 George B Rullman Method and apparatus for operating a single line conveyor
US3917894A (en) * 1968-01-15 1975-11-04 Tee Pak Inc Process for coating regenerated cellulose film and the coated film
US4876092A (en) * 1986-02-01 1989-10-24 Teikoku Seiyaku Kabushiki Kaisha Sheet-shaped adhesive preparation applicable to oral cavity
US4938998A (en) * 1985-08-24 1990-07-03 Juergen Stock Process for treating the surface of a plastic article
US20030107149A1 (en) * 2001-10-12 2003-06-12 International Fluidics. Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US20040258896A1 (en) * 2001-10-12 2004-12-23 Monosolrx Llc. Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US20060039958A1 (en) * 2003-05-28 2006-02-23 Monosolrx, Llc. Multi-layer films having uniform content
US20060147493A1 (en) * 2002-07-22 2006-07-06 Yang Robert K Packaging and dispensing of rapid dissolve dosage form
US20070149731A1 (en) * 2001-10-12 2007-06-28 Monosolrx, Llc. PH modulated films for delivery of actives
US20070154527A1 (en) * 2001-10-12 2007-07-05 Monosoirx, Llc Topical film compositions for delivery of actives
US20070172515A1 (en) * 2006-01-20 2007-07-26 Monosolrx, Llc Film bandage for mucosal administration of actives
US20070190157A1 (en) * 2006-01-20 2007-08-16 Monosoirx, Llc. Film lined packaging and method of making same
US20070281003A1 (en) * 2001-10-12 2007-12-06 Fuisz Richard C Polymer-Based Films and Drug Delivery Systems Made Therefrom
US20080044454A1 (en) * 2002-04-11 2008-02-21 Monosolrx Llc Uniform films for rapid dissolve dosage form incorporating taste-masking compositions
US20080075825A1 (en) * 2006-09-20 2008-03-27 Fuisz Richard C Edible Water-Soluble Film Containing a Foam Reducing Flavoring Agent
US20080081071A1 (en) * 2006-09-29 2008-04-03 Pradeep Sanghvi Film Embedded Packaging and Method of Making Same
US20080260809A1 (en) * 2002-04-11 2008-10-23 Monosol Rx, Llc Polyethylene oxide-based films and drug delivery systems made therefrom
US20100021526A1 (en) * 2001-10-12 2010-01-28 Monosol Rx, Llc Ph modulated films for delivery of actives
US7666337B2 (en) 2002-04-11 2010-02-23 Monosol Rx, Llc Polyethylene oxide-based films and drug delivery systems made therefrom
US20110033542A1 (en) * 2009-08-07 2011-02-10 Monosol Rx, Llc Sublingual and buccal film compositions
US8475832B2 (en) 2009-08-07 2013-07-02 Rb Pharmaceuticals Limited Sublingual and buccal film compositions
US8663687B2 (en) 2001-10-12 2014-03-04 Monosol Rx, Llc Film compositions for delivery of actives
US8765167B2 (en) 2001-10-12 2014-07-01 Monosol Rx, Llc Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions
US8900498B2 (en) 2001-10-12 2014-12-02 Monosol Rx, Llc Process for manufacturing a resulting multi-layer pharmaceutical film
US8900497B2 (en) 2001-10-12 2014-12-02 Monosol Rx, Llc Process for making a film having a substantially uniform distribution of components
US8974826B2 (en) 2010-06-10 2015-03-10 Monosol Rx, Llc Nanoparticle film delivery systems
US10272607B2 (en) 2010-10-22 2019-04-30 Aquestive Therapeutics, Inc. Manufacturing of small film strips
US10285910B2 (en) 2001-10-12 2019-05-14 Aquestive Therapeutics, Inc. Sublingual and buccal film compositions
US11077068B2 (en) 2001-10-12 2021-08-03 Aquestive Therapeutics, Inc. Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions
US11191737B2 (en) 2016-05-05 2021-12-07 Aquestive Therapeutics, Inc. Enhanced delivery epinephrine compositions
US11207805B2 (en) 2001-10-12 2021-12-28 Aquestive Therapeutics, Inc. Process for manufacturing a resulting pharmaceutical film
US11273131B2 (en) 2016-05-05 2022-03-15 Aquestive Therapeutics, Inc. Pharmaceutical compositions with enhanced permeation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2763571A (en) * 1954-03-23 1956-09-18 American Cyanamid Co Non-fibrous regenerated cellulose film carrying an anchoring agent and method of making
US2823141A (en) * 1953-05-08 1958-02-11 Olin Mathieson Process for coating regenerated cellulose film with resin and resulting product

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2823141A (en) * 1953-05-08 1958-02-11 Olin Mathieson Process for coating regenerated cellulose film with resin and resulting product
US2763571A (en) * 1954-03-23 1956-09-18 American Cyanamid Co Non-fibrous regenerated cellulose film carrying an anchoring agent and method of making

Cited By (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3447948A (en) * 1965-09-02 1969-06-03 Fmc Corp Resin coated cellulosic sheet having reduced tendency to accumulate an electrostatic charge
US3316120A (en) * 1966-06-03 1967-04-25 American Cyanamid Co Process for preparing topcoated plasticized non-fibrous regenerated cellulose film and the resultant product
US3917894A (en) * 1968-01-15 1975-11-04 Tee Pak Inc Process for coating regenerated cellulose film and the coated film
US3505072A (en) * 1969-06-09 1970-04-07 George B Rullman Method and apparatus for operating a single line conveyor
US4938998A (en) * 1985-08-24 1990-07-03 Juergen Stock Process for treating the surface of a plastic article
US4876092A (en) * 1986-02-01 1989-10-24 Teikoku Seiyaku Kabushiki Kaisha Sheet-shaped adhesive preparation applicable to oral cavity
US20070281003A1 (en) * 2001-10-12 2007-12-06 Fuisz Richard C Polymer-Based Films and Drug Delivery Systems Made Therefrom
US10888499B2 (en) 2001-10-12 2021-01-12 Aquestive Therapeutics, Inc. Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US20050184427A1 (en) * 2001-10-12 2005-08-25 Monosolrx, Llc. Thin film with non-self-aggregating uniform heterogeneity and drug delivery systems made therefrom
US9855221B2 (en) 2001-10-12 2018-01-02 Monosol Rx, Llc Uniform films for rapid-dissolve dosage form incorporating anti-tacking compositions
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NL247796A (enrdf_load_stackoverflow) 1900-01-01
FR1245448A (fr) 1960-11-04
BE589296A (fr) 1960-10-03

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