US3567491A - Coating compositions - Google Patents
Coating compositions Download PDFInfo
- Publication number
- US3567491A US3567491A US718378A US3567491DA US3567491A US 3567491 A US3567491 A US 3567491A US 718378 A US718378 A US 718378A US 3567491D A US3567491D A US 3567491DA US 3567491 A US3567491 A US 3567491A
- Authority
- US
- United States
- Prior art keywords
- percent
- acrylamide
- ethylene
- paper
- vinyl chloride
- 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
Links
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H19/22—Polyalkenes, e.g. polystyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/10—Aqueous solvent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions 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 a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions 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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D127/00—Coating compositions based on 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 a halogen; Coating compositions based on derivatives of such polymers
- C09D127/02—Coating compositions based on 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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
- C09D127/04—Coating compositions based on 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 a halogen; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C09D127/08—Homopolymers or copolymers of vinylidene chloride
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/10—Coatings without pigments
- D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
- D21H19/20—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- Y10T428/27—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.]
- Y10T428/273—Web or sheet containing structurally defined element or component, the element or component having a specified weight per unit area [e.g., gms/sq cm, lbs/sq ft, etc.] of coating
- Y10T428/277—Cellulosic substrate
Definitions
- This invention relates to fibrous substrates and the coating thereof. More particularly, this invention is concerned with novel coated fibrous substrates in sheet and roll form in which the substrate may be paper, paper board, preformed paper containers, fabrics or other fibrouslike bases.
- the substrate is sequentially coated with an interpolymer latice of ethylene, vinyl chloride, and acrylamide with or without small quantities of other monomers, and with a polyvinylidene chloride polymer.
- This invention further provides that either the interpolymer or polyvinylidene chloride polymer may be used as the precoat and with the overcoat or second coating being the polymer which is not utilized as the precoat.
- Fibrous substrates such as paper
- Paper has a very poor resistance to penetration by water vapor, gases, oil, solvents and greases.
- Wax To improve the water vapor barrier resistance, paper has been coated with a variety of substances. The most common paper coating is Wax. While Wax coated paper has good Water vapor barrier resistance in a smooth or uncreased condition, it has poor resistance after it is creased. Apparently the brittleness of the wax is so great that creasing causes it to fracture and break thereby providing many areas through which water vapor can pass with little or no resistance. Additionally, wax coated paper does not serve to form a hard and scuif resistant surface.
- asphalt is a black, toxic material which limits its application as a paper coating; particularly in the food packaging industry.
- asphalt coatings are subject to changes in flow properties with a variance in temperature.
- Paper has also been coated with a film of polyethylene.
- the resulting polyethylene coated paper is found to have less resistance to water vapor penetration than wax coated paper when the coat is tested in a flat or smooth uncreased condition.
- the polyethylene coated paper is found to be a better barrier than the wax coated paper when creased.
- Plasticized polyvinyl chloride polymers are used in paper coating applications. Since the polyvinyl chloride is normally externally plasticized a loss in permanence of the resistance to water, oil, grease and solvents is experienced as a result of the extraction and bleeding of the plasticizer.
- interpolymers which are prepared and used as one of the coating compositions according to this invention in aqueous dispersion or latex form generally contain from about 5 percent to about percent ethylene, from about 30 to about 95 percent vinyl chloride, and from about 0.1 to about 10 percent of acrylamide.
- Part of the acrylamide in the interpolymer may be replaced by polar monomers such as acrylonitrile methacrylamide, N- (lower alkyl)acrylamide and N-(lower alkyl)methacrylamide containing from 1 to 3 carbon atoms in said lower alkyl groups, N-methylol acrylamide, N[2-(2-methyl-4- oxopentyl)]acrylamide, acrylic acid, methacrylic acid, and alkali metal and ammonium salts of acrylic and methacrylic acids, maleic acid, fumaric acid, half and complete alkali metal and ammonium salts of male-ic and fumaric acid, aconitric acid, itaconic acid, citraconic acid, and alkali metal and ammonium salts thereof half alkyl esters of maleic, fumaric, itaconic and citraconic acids having from 1 to 6 carbon atoms in each alkyl group, acrylyl and methacrylyl esters of hydroxyalkanoic acids
- the acrylamide generally should constitute at least 50 percent by weight of the third or polar monomer of said interpolymer, and preferably constitutes at least about percent of said polar monomer.
- the interpolymers as prepared in aqueous dispersed form are at least terpolymers containing ethylene, vinyl chloride, and acrylamide, and may be a quaternary or higher polymers containing one or more of the above exemplified additional polar monomers in small quantities but generally such additional monomers will not be present in the interpolymer in quantities greater than about 2 percent by weight.
- the interpolymer contain from about 5 percent to about 70 percent ethylene, 30 percent to about 95 percent vinyl chloride, and from about 1 percent to about percent acrylamide.
- a specific example of choice, as presently understood, is a terpolymer containing from about 19 to 23 percent ethylene, about 74 to about 78 percent vinyl chloride, and from about 2 to about 4 percent acrylamide.
- interpolymers used in the practice of this invention are generally unmodified, the modified interpolymers are included for use in this invention.
- Theinterpolymers are particularly amenable to h gdrolytic modiiication by the use ofsmall quantities of a strongly alkaline material such as an alkali metal hydroxide, or a quaternary ammonium hydroxide such as the mineral acids, e.g., hydrochloric, sulfuric, phosphoric, nitric.
- the base or acid used preferably has an ionization constant higher than l0- at 25 C.
- the hydrolyzing treatment, performed with an acid or a base need not be performed to the same extent, especially if the interpolymer contains polar monomers in addition to the acrylamide.
- the aqueous dispersion or polymer latex of the ethylene, vinyl chloride, and acrylamide is generally treated with aqueous base or acid in an amount which is;chemically equivalent to up to about 1100 percent of the amide equivalent in the interpolymer.
- polar monomers which may be used, as described above, to replace part of the acrylamide in the polymers of this invention'include acrylonitrile, N-methylacrylamide, N-ethylacrylamide, N-propylacrylamide, methacrylamide, acrylic methacrylic, maleic, fumaric, itaconie, aconitic, and citraconic acids and alkali metal and ammonium salts of such acids,.preferably the sodium, potassium or ammonium salts, alkyl esters of such acids, e.g., methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, butyl methacrylate, ethyl methacrylate, :monoethyl maleate, dipropyl fumarate, acrylyl 3-hydroxypropionate, methacrylyl 4-hydroxybutanoate, N-acrylylacetamide,N-methacrylyl hexamide, Z-hydroxye
- the ethylene, vinyl chloride, acrylamide interpolymers may be prepared by first mixing ethylene and vinyl chloride in an aqueous medium in the presence of any suitable anionic or nonionic emulsifier and any initiator capable of generating free radicals in the chemical mixture at the chosen reaction temperature and pressure.
- the acrylamide preferably in aqueous solution either alone or mixed with the appropriate amounts of other polar monomers, is added to the polymerizing ethylene and; vinyl chloride mixture gradually throughout the'reaction. Since the acrylamide is very reactive, it cannot be all added at the start of the reaction.
- ethylene/vinyl chloride/acrylamide interpolymers are readily prepared by various means known to' the art.
- the ethylene/ vinyl chloride/acrylamide interpolymers used in this invention are preferably prepared by a process which comprises mixing ethylene and vinyl chloride monomers in the presence of an alkaline buffered reduction-oxidation (redox) initiator-catalyst system, water and from about 1 percent to aboutS percent by weight based upon the monomer feed, or from about 4 percent to about 7 percent based upon the polymer 'product of an anionic or nonionic emulsifying agent having tion are carried out in a 3820 ml. pressure vessel at 30 C..
- redox alkaline buffered reduction-oxidation
- EXAMPLE 1 This example illustrates the preparation of 21/76/3 ethylene/ vinyl chloride/acrylamide terpolymer latex, and the post-stabilization of such latex with an emulsifier.
- Reaction vessel initial charge u. K S O (KPS) 11.0 NaHCO 15.0 FC(NO3)39HQO 08 Tetrasodium ethylenediaminetetraacetate (Na EDTA) 1.5 Sodium lauryl sulfate (SLS) L 1.2 Vinyl chloride (VCli' L 450 Ethylene (E) l 150 H O to make 1700 ml.
- KPS K S O
- FC(NO3)39HQO 08 Tetrasodium ethylenediaminetetraacetate
- SLS Sodium lauryl sulfate
- VCS Vinyl chloride
- E Ethylene
- The. above ingredientmixture was heated to .30" C. with stirring to give a reaction. pressure of 850 p.s.i.g.
- the polymerization was started by adding a 1 Msodium formaldehyde sulfoxylate-NaHSO -CH O 2H (SFS 1.5 M ammonium hydroxide (NH OH) solution to the mixture at a rateof 5.2 ml./hr. at the same time 18- ml./hr.
- ethylene/vinyl chloride/acrylamide polymer latex was obtained containing 47 percent total solids, and 1.5 percent,,sodium lauryl sulfate (based on the weight oftthe polymer). It had a pH of 7.7.
- the composition of the terpolymer was about 21/ 76/ 3 ethylene/ vinyl chloride/acrylamide.
- the latex was ready for use directly as a barrier coating on fibrous substrates such as paper and paperboard.
- EXAMPLE 2 This example illustrates the preparation of the base modified ethylene/vinyl chloride/acrylamide terpolymer.
- Example 2 Using the same reaction vessel and ingredients as are described in Example 1, except that only 10.0 g. of KPS, and only 0.5 g. of SLS was used in the initial; ingredient charge.
- the SFS/NH OH solution was added at the rate of 4 ml./hr. and the SL8 solution was added at 8 mL/hr.
- the polymerization reaction stopped after 5.75 hours with a total of about 1340 g. of vinyl chloride, ml. of acrylamide solution, 23 ml. of SFS/NH OH solution, and 43 ml. of 245 percent SLS being added.
- the resulting terpolymer latex was post-stabilized by mixing therewith an additional 17 ml. of 25 percent sodium lauryl sulfate (SLS).
- SLS sodium lauryl sulfate
- the stabilized latex was then vented from the bottom of the reaction vessel. There was obtaineda3460 g. of material conatining. 49 percent total solids, 1 percent of the SL8 and essentially the same terpolymer as dc scribed in Example 1. The particle size of this polymer latex was somewhat larger than that of Example 1.
- This stabilized ethylene/vinyl chloride/acrylamide terpolymer latex was warmed at 50 C. for 4 to 16 hours after adding 0.4-2.0 g. of sodium hydroxide (added thereto as a 10 percent NaOH in water solution) per kilogram of latex.
- EXAMPLE 3 A four monomer component polymer latex was prepared as follows:
- a pressure reaction vessel was initially charged with 9.0 g. KPS, 12.0 g. NaHCO 0.8 g. FC(NO3) -9H 0, 1.5 g. Na EDTA, 0.5 g. SLS, H O to make 1700 ml., 575 g. E, 470 g. VCl.
- the polymer composition was a 21/ 76/ 2.3 07 ethylene/vinyl chloride/acrylamide/sodium acrylate polymer. It was suitable for use directly as a coating composition for paper and paperboard. The procedure is repeated substituting for the sodium acrylate an equivalent amount of sodium methacrylate of substantially the same monomer portion is obtained.
- the fibrous substrates to which the compositions are applied in carrying out the present invention include papers of all types, such
- the coatings may be applied to building construction papers and boards, such as the facing paper on plasterboard. It may be used as a release-coating on a paper to be used as a liner in a concrete molding form or adapted to be used for covering freshly-laid concrete roads.
- the fibrous substrates such as paper which may be sequentially coated according to this invention with an ethylene, vinyl chloride, acrylamide interpolymer as the precoat or overcoat to produce a product of enhanced barrier characteristics may contain from about 0.5 to .90 pounds of ethylene, vinyl chloride, acrylamide interpolymers on one side per ream (a ream is 3000 sq. ft. and equals 500 sheets, 24 inches by 36 inches). Generally, however, about 1 to 20 pounds of ethylene, vinyl chloride, acrylamide interpolymers per ream is adequate while 1 to 4 pounds is all that is needed for many purposes.
- the amount of polyvinylidene chloride polymer applied as a precoat or an overcoat may be varied considerably. In general, however, the useful range is about 0.1 to 20 pounds of polyvinylidene chloride polymer per ream on one side of a substrate such as paper. For most purposes, 05 to 4 pounds of polyvinylidene chloride polymer per ream is adequate.
- Coating rod numbers 6, 18 and 28 may be utidiameter and more winds for a given rod length which deposits a light continuous wet film whereas the No. 28 rod has a larger wire diameter and fewer winds per inch which deposits a much heavier film.
- the paper is mounted on a flat glass surface, the wire wound rod is placed in the draw-down bar which is positioned at the top of the sheet, latex is then poured across the paper web just in front of the draw-down bar, the draw-down bar is pulled at a uniform speed across the paper web leaving behind a uniformly even wet latex film. All precoated samples are permitted to air dry overnight, then exposed to 120 C. for 2 minutes, then calendered.
- the top coat of ethylene vinyl chloride acrylamide interpolymer or polyvinylidene chloride polymer is applied to the precoated paper utilizing the same procedure as in applying the precoat.
- the coatings may also be prepared by coagulating the polymers from a latex, washing and then extruding the coating by methods known to the art.
- a series of paper sheets of 50 lb. bleached kraft base stock were precoated with varying weights ethylene, vinyl chloride, acrylamide interpolymers and top coated with varying Weights of polyvinylidene chloride polymer.
- the moisture vapor transmission rates for creased and uncreased paper samples are shown in Table II.
- the oil resistance properties of the same coated papers are given in Table III.
- the coatings are then tested for various physical properties.
- the test procedures are hereinafter described and the results are listed in Tables II and III.
- test methods used to determine the physical properties of the paper coated with ethylene, 'vinyl chloride, acrylamide interpolymer and polyvinylidene chloride polymer are listed below with explanatory notes where necessary. Samples were conditioned according to TAPPI T402m49 before testing. The paper base stock used in the testing hereinafter described is indicated for each example.
- Oil resistance creased box test -A 6" x 6" coated one side specimen blank is folded in half in each direction as well as diagonally from corner to corner, each fold i subjected to a 1b. pressure. The blank is further folded one inch from each edge and then made up into a 4" x 4" box having 1" side walls with the coated surface inside. All creases, except those made by the side walls folds converge as an apex in the center of the box bottom. 50 cc. No. 10 SAE oil is poured into the box and the time required to penetrate the creased areas is noted.
- Moisture-vapor transmission rateA.-S.T.M. 3-988 (tropical atmosphere).-Reported as grams H O/100 sq. inches/24 hrs. at 100 F. and 90% relative humidity.
- compositions B through L impart to the paper the desirable combination of oil and water vapor resistance and good flexibility. Such combinations of properties is not attainable when polyvinylidene chloride polymer is used as the sole coating material.
- the paper to be coated can be of a wide variety of types including kraft, bond, parchment, etc.
- the type, weight and other physical properties of the paper to which the coating is applied do not significantly offer the improvement in oil resistance and moisture vapor transmission rate brought about by the method of the invention.
- coated papers provided by the present invention have utility for many purposes which will be obvious to those skilled in the art.
- the coated papers may be used to wrap food products where it is desired to prevent the transmission of moisture from the atmosphere to the packaged product.
- the coated papers are easily heat sealed and hold liquids well. As a result, such coated papers can be used in the manufacture of paper drinking cups and the like.
- a fibrous substrate having on at least one surface TABLE II Total Moisture vapor transmission 1 Rod Coating wt., Rod Coating wt., coating wt., Composition Latex No lbs/1,000 it. Latex No. lbs/1,000 it. lbs/1,000 it. (Increased Greased 6 4. 35 4. 35 1. 36 1. 6 2. 25 6 2. 00 4. 25 1. 77 1. 98 4 1. 40 PVDC 6 2. 80 4. 20 6. 21 7. 68 6 1. 70 6 2. 40 4. 10 3. 78 4. 8 2.10 PVDG 6 1. 68 3. 78 1. 72 1. 79 6 1. PVDC 4 2.10 3. 80 4. 75 5. 21 o 6 1.70 PVDC 8 3.45 5.15 1.21 1.97 II Example 2. 4 2. 30 PVD C 6 2. 51 4. 81 5.
- Example thereof a sequential coating comprising from about 0.5 to about 90 pounds of an interpolymer and from about 0.1 to about 20 pounds of polyvinylidene chloride polymer per each 300 square feet of fibrous substrate, provided that when the coating in immediate contact with the substrate is an interpolymer the superimposed coating is polyvinylidene chloride polymer and further provided that when the initial coating is polyvinylidene chloride polymer the superimposed coating is an interpolymer, said interpolymer being selected from the group consisting of (a) an interpolymer containing from about to about 70 percent ethylene, from about 30 to about 95 percent vinyl chloride, and from about 0.1 to about percent of at least one other polar monomer including at least about 0.1 percent to about 10 percent of acrylamide, any remainder of said polar monomer content being selected from the group consisting of acrylonitrile; methacrylamide; N-(alkyl) acrylamide and N-(alkyl) methacryl amide having from 1 to 3 carbon atoms in each alky
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paper (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71837868A | 1968-04-03 | 1968-04-03 | |
US71836768A | 1968-04-03 | 1968-04-03 | |
US71837168A | 1968-04-03 | 1968-04-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3567491A true US3567491A (en) | 1971-03-02 |
Family
ID=27418978
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US718378A Expired - Lifetime US3567491A (en) | 1968-04-03 | 1968-04-03 | Coating compositions |
US718367A Expired - Lifetime US3567502A (en) | 1968-04-03 | 1968-04-03 | Barrier coatings |
US718371A Expired - Lifetime US3632424A (en) | 1968-04-03 | 1968-04-03 | Barrier coatings |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US718367A Expired - Lifetime US3567502A (en) | 1968-04-03 | 1968-04-03 | Barrier coatings |
US718371A Expired - Lifetime US3632424A (en) | 1968-04-03 | 1968-04-03 | Barrier coatings |
Country Status (8)
Country | Link |
---|---|
US (3) | US3567491A (fr) |
BE (2) | BE730933A (fr) |
CA (1) | CA969694A (fr) |
DE (1) | DE1934616A1 (fr) |
FR (1) | FR2005457A1 (fr) |
LU (2) | LU58350A1 (fr) |
NL (1) | NL6905098A (fr) |
SE (2) | SE353111B (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755233A (en) * | 1970-07-16 | 1973-08-28 | Monsanto Co | Composition comprising ethylene/vinyl chloride/n-methylol acrylamide and a mineral pigment for coating paper |
US3925287A (en) * | 1973-02-02 | 1975-12-09 | Monsanto Co | Ethylene/vinyl chloride interpolymers |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3922424A (en) * | 1972-05-22 | 1975-11-25 | Monsanto Co | Non-woven fibrous material bonded with ethylene/vinyl chloride interpolymers |
US5510124A (en) * | 1994-03-23 | 1996-04-23 | Wm. Wrigley Jr. Company | Method for packaging single units of chewing gum and chewing gum so packaged |
US5897411A (en) * | 1997-10-01 | 1999-04-27 | Reichhold Chemicals, Inc. | Repulpable moisture vapor barrier |
US6001397A (en) * | 1997-12-23 | 1999-12-14 | Wm. Wrigley Jr. Company | Method for packaging chewing gum and chewing gum so packaged |
US6010724A (en) * | 1997-12-23 | 2000-01-04 | Wm. Wrigley Jr., Company | Packaged chewing gum and methods for packaging chewing gum |
WO2002031248A2 (fr) * | 2000-10-13 | 2002-04-18 | Kimberly-Clark Worldwide, Inc. | Emballage auto-thermoscellable et son procede de fabrication |
US20190023951A1 (en) | 2017-07-19 | 2019-01-24 | Ccl Label, Inc. | Barrier coating for adhesive labels |
FR3137392A1 (fr) | 2022-07-01 | 2024-01-05 | Tifany Emballages | Composition bicouches et son utilisation pour l’étanchéisation |
FR3137386A1 (fr) | 2022-07-01 | 2024-01-05 | Tifany Emballages | Composition et son utilisation pour l’étanchéisation |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2914498A (en) * | 1953-11-30 | 1959-11-24 | Union Carbide Corp | Aqueous dispersion of vinyl chloride polymer containing substituted polyacrylamide |
US2945775A (en) * | 1955-04-18 | 1960-07-19 | Dow Chemical Co | Sizing of paper with acrylamide polymers |
DE1250577B (de) * | 1959-11-28 | 1967-09-21 | tarbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brunmg, Frankfurt/M | Überzugsmittel zum Beschichten von Oberflachen von Korpern aus makromolekularen organischen Stoffen |
GB913145A (fr) * | 1960-01-02 | 1900-01-01 | ||
DE1495645C3 (de) * | 1961-05-26 | 1974-11-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung stabiler, wäßriger Emulsionen bzw. Dispersionen von Äthylen-Mischpolymerisaten |
DE1495707B2 (de) * | 1963-01-12 | 1972-01-27 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung stabiler emulsionen von copoly merisaten des aethylens |
NL131848C (fr) * | 1963-11-20 | 1900-01-01 | ||
US3409568A (en) * | 1964-11-27 | 1968-11-05 | Monsanto Co | Ethylene/vinyl chloride copolymer pigment binder for coated paper products and process of preparation |
US3347811A (en) * | 1965-02-02 | 1967-10-17 | Du Pont | Process for preparing aqueous dispersions of ethylene copolymers |
US3380851A (en) * | 1965-03-31 | 1968-04-30 | Air Reduction | Nonwoven fabric with vinyl acetateethylene-n-methylol acrylamide interpolymer as binder |
US3428582A (en) * | 1966-05-06 | 1969-02-18 | Monsanto Co | Interpolymer aqueous dispersions and paper coated therewith |
-
1968
- 1968-04-03 US US718378A patent/US3567491A/en not_active Expired - Lifetime
- 1968-04-03 US US718367A patent/US3567502A/en not_active Expired - Lifetime
- 1968-04-03 US US718371A patent/US3632424A/en not_active Expired - Lifetime
-
1969
- 1969-03-28 CA CA047,241A patent/CA969694A/en not_active Expired
- 1969-04-02 LU LU58350D patent/LU58350A1/xx unknown
- 1969-04-02 DE DE19691934616 patent/DE1934616A1/de not_active Ceased
- 1969-04-02 FR FR6910069A patent/FR2005457A1/fr not_active Withdrawn
- 1969-04-02 SE SE04787/69A patent/SE353111B/xx unknown
- 1969-04-02 BE BE730933D patent/BE730933A/xx unknown
- 1969-04-02 BE BE730935D patent/BE730935A/xx unknown
- 1969-04-02 LU LU58351D patent/LU58351A1/xx unknown
- 1969-04-02 NL NL6905098A patent/NL6905098A/xx unknown
- 1969-04-02 SE SE04786/69A patent/SE352907B/xx unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3755233A (en) * | 1970-07-16 | 1973-08-28 | Monsanto Co | Composition comprising ethylene/vinyl chloride/n-methylol acrylamide and a mineral pigment for coating paper |
US3846354A (en) * | 1970-07-16 | 1974-11-05 | Monsanto Co | Composition comprising ethylene/vinyl chloride/n-methylol acrylamide terpolymer, starch and a mineral pigment for coating paper |
US3925287A (en) * | 1973-02-02 | 1975-12-09 | Monsanto Co | Ethylene/vinyl chloride interpolymers |
Also Published As
Publication number | Publication date |
---|---|
SE352907B (fr) | 1973-01-15 |
US3567502A (en) | 1971-03-02 |
US3632424A (en) | 1972-01-04 |
DE1934616A1 (de) | 1969-12-04 |
LU58351A1 (fr) | 1969-11-13 |
NL6905098A (fr) | 1969-10-07 |
BE730933A (fr) | 1969-10-02 |
LU58350A1 (fr) | 1969-11-13 |
SE353111B (fr) | 1973-01-22 |
FR2005457A1 (fr) | 1969-12-12 |
BE730935A (fr) | 1969-10-02 |
CA969694A (en) | 1975-06-17 |
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