US2281589A - Moistureproof wrapping material - Google Patents

Moistureproof wrapping material Download PDF

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Publication number
US2281589A
US2281589A US339493A US33949340A US2281589A US 2281589 A US2281589 A US 2281589A US 339493 A US339493 A US 339493A US 33949340 A US33949340 A US 33949340A US 2281589 A US2281589 A US 2281589A
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US
United States
Prior art keywords
coating
moistureproofing
sheet
film
cellulose
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
US339493A
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English (en)
Inventor
James A Mitchell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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
Priority to BE442159D priority Critical patent/BE442159A/xx
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US339493A priority patent/US2281589A/en
Priority to DEK161251D priority patent/DE752714C/de
Priority to CH231939D priority patent/CH231939A/de
Priority to FR874945D priority patent/FR874945A/fr
Application granted granted Critical
Publication of US2281589A publication Critical patent/US2281589A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/13—Unsaturated aldehydes, e.g. acrolein; Unsaturated ketones; Ketenes ; Diketenes
    • 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
    • C08J2429/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2429/12—Homopolymers or copolymers of unsaturated ketones
    • 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]
    • Y10T428/31801—Of wax or waxy material
    • Y10T428/31804—Next to cellulosic
    • 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]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic
    • Y10T428/31884—Regenerated or modified cellulose
    • Y10T428/31891—Where addition polymer is an ester or halide
    • 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]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31935—Ester, halide or nitrile of addition polymer
    • 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

Definitions

  • the resulting sheet of softened regenerated cellulose coated or sized with an insoluble deposit of the ketone dimer was. after conditioning to bring it to the desired moisture content. coat ed with a moistureprooflns composition of the by passing it therethrough. The excess of the moistureproofing coating composition was removed by scraping, and the coated sheet dried at a temperature above the melting point of the wax. The finished web was again conditioned to bring it to the desired moisture content.
  • the resulting product was a sheet of regenerated cellulose with a moistureproofing coating which was substantially odorless, transparent, flexible and moistureproof.
  • the moistureproofing coating adhered very tenaciovsly to the sheet when in direct contact with water for very substantial periods of time (3 days or more).
  • the moistureproofing coating was found to loosen and flake off in a period of 6 hours when subjected to contact with water.
  • the product hav- 1 ing the anchored coating served as a very satisfactory wrapping for products containing large amounts of water or moisture, such as butter, cheese, wet fish, frozen fish, ice cream and the like, even when in direct contact therewith.
  • Example II A film prepared as described in Example I and softened with ethylene glycol, was treated with a The excess sizing material was removed by Per cent Linseed oil acids ketene dimers 5 Ethyl cellulose 0.5 Toluene 94.5
  • the film was found to be transparent and completely tack-free. It could be stored for considerable periods of time without exhibiting any tendencies for adjacent sheets to stick together.
  • This material was coated with a moistureproofing composition of the following formulation:
  • moistureproof sheet wrapping material which'retained its coating in a firmly adherent condition in excess of 1 week when subjected to direct contact with water.
  • Example III Regenerated cellulose film, softened with glycerol and dried in the manner described in U. S. A.
  • Patent No. 1,606,824 (Brandenberger) was sprayed with a solution comprising:
  • Example V A regenerated cellulose film, softened with glycerol, was coated, by means of spraying, with a solution comprising:
  • moistureproofing coating was found to adhere firmly to the base sheet even when submerged in water for a period of time considerably greater than that required to loosen the coating from a similar sheet coated with the same moistureproofing composition in which the intermediate layer of ketene dimer had been omitted.
  • Example VI A regenerated cellulose film, softened with glycerol, was coated by passing it through a solution containing:
  • Toluene 730 The moistureproofing coating, after removal of the solvent, was found to adhere firmly to the base sheet even when submerged in water for a period of time much greater than that required to loosen a similar coating from a similar base sheet in which there was no intermediate layer of ketene dimer.
  • Example VII A regenerated cellulose film softened with glycerol, was sized by passing through a solution of:
  • the moistureproofing coating was found to adhere firmly to the base sheet 'even when submerged in-water for a' period of time considerably greater than that required to loosen the coating from a similar sheet coated with the same moistureproofing composition in which the intermediate layer of ketene dimer had been omitted.
  • Example VIII A regenerated cellulose film softened with glycerol was coated by passing through a solution containing:
  • Pliolite is a thermoplastic rubber derivative made by condensing rubber with a catalyst such as tin tetrachloride (see Pa er Trade Journal, page 96, February 23, 1939, J. l. E. XXVI, 125, and U. s. A. Patents Nos. 1,797,188, 1,846,247, 1,853,334 and 2,052,391). The chemical structure is also described in Rubber Age, April 1939, and J. I. E. c. XIX, 1033.
  • the moistureproofing coating was found to adhere firmly to the base sheet even when submerged in water for a period of time considerably greater than that required to loosen the coating from a similar sheet coated with the same moistureproofing composition in which the intermediate layer of ketene dimer had been omitted.
  • this invention contemplates any transparent, water-sensitive, non-fibrous cellulosic sheet, especially those containing water miscible softening agents (glycerol, glycol, etc.).
  • This includes cellulosic film regenerated or precipitated from aqueous alkaline cellulosic dispersions or solutions, for example, regenerated cellulose precipitated from viscose (solutions of cellulose xanthate), cuprammonium cellulose and cellulose ethers and esters, which ethers and esters have not been substituted to an extent or degree sufiicient to cause them to loose their water sensitivity, such as glycol cellulose, cellulose glycolic acid, alkyl cellulose (preferably methyl or ethyl cellulose), and similar celluloslc products.
  • anchorage of moistureproofing coatings on regenerated cellulose and like film is obtained by an ethenone material anchoring coat.
  • anchor or equivalents (anchoring, anchored, etc.) is meant the securing of the surface coating to the base in such a way that the resultant product will withstand the deleterious eifects of water (or moisture).
  • the surface coating will not loosen and/or flake off from the water sensitive base when the product is directly in contact with water for appreciable and substantial periods of time (several days when immersed in water at 20 (3.).
  • Whether a substance is an anchoring agent or not is easily shown, for example, by comparing the time of immersion in water required to loosen a moistureproof coating which has been coated over a sub-layer of the substance, with the time required to bring about the same loosening with the same moistureproofing coating in the absence of the sub-layer of the substance being tested.
  • the ethenones of these Sauer applications are of two general types, namely, aldoethenones, in which only one methylene hydrogen is replaced or substituted, and ketoethenones, in which both methylene radicals have been replaced.
  • aldoethenones in which only one methylene hydrogen is replaced or substituted
  • ketoethenones in which both methylene radicals have been replaced.
  • the more important subdivisions of the aldoethenone group are the alkylethenones and acylethenones.
  • the main sub-generic groups are the dialkylethenones and the acylalkylethenones.
  • the ethenones can be formed by the dimerization of the corresponding ketenes, and may therefore also be called ketene dimers.”
  • the preferred radicals are derived from propionic, butyric, caprylic, lauric, stearic, keto-stearic, undecylenic, oleic, linoleic, drying oil acids and fish oil acids.
  • a long list of specific ethenones and their formulae are disclosed in U. S. A. patent application Serial No. 234,842, filed October 3, 1938, by Handford, to which reference is made in the interest of brevity.
  • Application of the ethenone material to the base sheet may be made by any of the conventional coating or sizing procedures, as for example, with applicator rolls, by dipping or immersing the sheet in a bath of the material, by brushing a solution on the sheet, by spraying the solution on a sheet, or any other convenient, means. After application of the under-coating composition it may be smoothed and the excess removed in any suitable manner, as for example, by doctor knives, squeeze rolls, etc.
  • a preferred concentration range is 2% to 5%.
  • the ethenone material may be applied in pure form as a melt.
  • the solvent is evaporated after application of the solution, preferably at temperatures above normal room temperature, but not exceeding 125 0. It is desirable that the anchoring coat set up to a hard tack-free state in three to five minutes or less at a temperature of between '70 and 110 C. if
  • ethenone material which will produce a film or size of a fair degree of flexibility, is preferred.
  • the under-coat usually is extremely thin, being often within the range 0.00001 to 0.00003 of an inch in thickness.
  • the heat necessary (if any) to condition the ethenone treated sheet material for receiving its final moistureproofing coating may be applied in a variety of ways, as for example, by bringing the cellulosic sheet into contact with heated drier rolls (or other heated surfaces), or by leading the sheet (or web) through a heated atmosphere in some other manner (U. S. A. Patent No. 2,115,132, Alles 8: Edwards).
  • certain other substances non-reactive with the other ethenone material, may be combined therewith.
  • These include natural resins, synthetic resins, waxes, wax-like materials, cellulose substitution derivatives such as cellulose esters, cellulose ethers and the like. stances serve the specific purposes of giving desirable surface characteristics, such as non-tackiness, during subsequent operations, an increase in moistureproofness of the final product, etc.
  • Dyes and/or pigments may be added to either,
  • the intermediate or moistureproofing layer or both.
  • the moistureproofing coating composition com prises organic solvent soluble binder material from the group comprising cellulose substitution derivatives (cellulose esters, cellulose ethers, etc.) rubbery materials (rubber, balata, isoprene, neoprene, etc.), and polymerized alpha-beta unsaturated acid esters (alkyl methacrylates, etc.); moistureproofing material (waxes, waxy material, etc.) blending material and the plasticizing material, and it is applied from solution in an organic solvent.
  • organic solvent soluble binder material from the group comprising cellulose substitution derivatives (cellulose esters, cellulose ethers, etc.) rubbery materials (rubber, balata, isoprene, neoprene, etc.), and polymerized alpha-beta unsaturated acid esters (alkyl methacrylates, etc.); moistureproofing material (waxes, waxy material, etc.) blending material and the plasticizing material, and it is applied from
  • the preferred moistureproofing coating compositions are those of U. S. A. Patents No. 1,737,187 (Charch & Prindle), 2,077,400 (Collins), 2,137,636 (Barrett), and the like.
  • any wax (used generically to include waxy substances like paraffin wax, as well as true waxes which are monohydric alcohol esters of higher fatty acids) may be employed.
  • the constituents are dissolved in a solvent (a single organic liquid or mixture of liquids, as is expedient) to give a clear, homogeneous solution which may be smoothly'applied to the surface of the sized or coated base in a layer sufficiently thin that the'solids (resulting from evaporation of the solvent) will produce a layer in the neighborhood, and preferably not exceeding, 0.0005 of an inch in thickness.
  • a solvent a single organic liquid or mixture of liquids, as is expedient
  • the application of the moistureproofing coating may be accomplished by any suitable manner, such as application from a melt or solution in organic solvent. Passing the base film through a bath of the coating composition, spraying the composition on the base, etc., are preferred procedures.
  • any excess of the coating may be removed in any desired manner, such as by doctor knives, doctor rolls, etc.
  • Various coatin procedures are known in the art, and in the interest of brevity need not be reviewed here.
  • Patents No. 1,826,6967-8-9 Clearer films are obtained when the coated film is chilled rapidly after evaporation of the solvent from the coating.
  • the invention comprehends the coating of still other bases, such as rayon fabrics and the like, in order to anchor surface coatings thereto.
  • the present invention may be employed to improve the anchorage of various coattioned heretofore, for example, paper, cotton cloth, and the like, which are water sensitive.
  • various coattioned heretofore for example, paper, cotton cloth, and the like, which are water sensitive.
  • the ethenone material improves the adhesion between the coating and the base.
  • the ethenone material sizes may be used satisfactorily where the final coating is of a discontinuous character, as for example, in the printing of colors, symbols, indicia, advertisements, etc.
  • regenerated cellulose sheets, tubes, caps, sausage casings, etc. when coated or sized with the ethenone material, may be printed with printing ink either having a lacquer base or a drying oil base for giving any desired indicia, and after drying, the printing adheres securely to the base even after being subjected to rigid washing, boiling and other process steps.
  • the present invention effects the production of flexible, substantially odorless, non-fibrous, non-porous, cellulosic sheet material having a moistureproofing coating securely anchored thereto, which is resistant to deterioration when subjected to the action of liquid water over long periods of time.
  • a further advantage is the adaptability of the process of the invention to the equipment now used in the production of regenerated cellulose film and the like, without necessitating a substantial change in the design-of such equipment. Still further advantages are lower cost, minimum waste and greater efficiency.
  • the composite films of the present invention in the absence of pigments, have a high degree of transparency.
  • Moistureproofness, moistureproofing and moistureproof materials and expressions are defined in U. S. A. Patent No. 2,147,180 (Ubben). In the interest of brevity the definitions are not'repeated here. The terms and expressions related thereto and employed herein are used in accordance with such definitions.
  • a moistureproof wrapping material sheet comprising a regenerated cellulose base sheet having a moistureproofing coating adhered thereto with a layer of ethenone material of the formula:
  • R and Z are aliphatic groups
  • R and Z are aliphatic groupsfand thereafter over-coating the ketene dimer layer with a moistureproofing coating.
  • Per cent Oleic acid ketene dimer 5 Toluene 95 drying, coating with a moistureproofing coating composition comprising essentially:

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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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Laminated Bodies (AREA)
  • Paints Or Removers (AREA)
US339493A 1940-06-08 1940-06-08 Moistureproof wrapping material Expired - Lifetime US2281589A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE442159D BE442159A (enrdf_load_stackoverflow) 1940-06-08
US339493A US2281589A (en) 1940-06-08 1940-06-08 Moistureproof wrapping material
DEK161251D DE752714C (de) 1940-06-08 1941-05-29 Verankerung von Lackschichten auf wasserquellbaren Folien
CH231939D CH231939A (de) 1940-06-08 1941-07-04 Verfahren zum Verankern eines wasserabstossenden Überzugs auf einem wasserquellbaren Gebilde.
FR874945D FR874945A (fr) 1940-06-08 1941-08-30 Procédé d'imperméabilisation de pellicules perméables à l'eau

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US339493A US2281589A (en) 1940-06-08 1940-06-08 Moistureproof wrapping material

Publications (1)

Publication Number Publication Date
US2281589A true US2281589A (en) 1942-05-05

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US339493A Expired - Lifetime US2281589A (en) 1940-06-08 1940-06-08 Moistureproof wrapping material

Country Status (5)

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US (1) US2281589A (enrdf_load_stackoverflow)
BE (1) BE442159A (enrdf_load_stackoverflow)
CH (1) CH231939A (enrdf_load_stackoverflow)
DE (1) DE752714C (enrdf_load_stackoverflow)
FR (1) FR874945A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2465337A (en) * 1944-11-01 1949-03-29 Du Pont Process of preparing ketenes
US2627477A (en) * 1949-10-06 1953-02-03 Hercules Powder Co Ltd Higher alkyl ketene dimer emulsion
US2820719A (en) * 1952-08-27 1958-01-21 Davies Young Soap Company Process for rendering fabrics water repellent
DE1191682B (de) * 1954-08-23 1965-04-22 Warren S D Co Verfahren zur Herstellung von Streichpapier
US3189480A (en) * 1961-04-25 1965-06-15 Beiersdorf P & Co Ag Pressure sensitive adhesive sheet material with diketene-acrylic acid ester copolymer coating

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2465337A (en) * 1944-11-01 1949-03-29 Du Pont Process of preparing ketenes
US2627477A (en) * 1949-10-06 1953-02-03 Hercules Powder Co Ltd Higher alkyl ketene dimer emulsion
US2820719A (en) * 1952-08-27 1958-01-21 Davies Young Soap Company Process for rendering fabrics water repellent
DE1191682B (de) * 1954-08-23 1965-04-22 Warren S D Co Verfahren zur Herstellung von Streichpapier
US3189480A (en) * 1961-04-25 1965-06-15 Beiersdorf P & Co Ag Pressure sensitive adhesive sheet material with diketene-acrylic acid ester copolymer coating

Also Published As

Publication number Publication date
CH231939A (de) 1944-04-30
FR874945A (fr) 1942-08-31
DE752714C (de) 1952-10-27
BE442159A (enrdf_load_stackoverflow) 1900-01-01

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