[go: up one dir, main page]

US3015578A - Two-sided paper - Google Patents

Two-sided paper Download PDF

Info

Publication number
US3015578A
US3015578A US723654A US72365458A US3015578A US 3015578 A US3015578 A US 3015578A US 723654 A US723654 A US 723654A US 72365458 A US72365458 A US 72365458A US 3015578 A US3015578 A US 3015578A
Authority
US
United States
Prior art keywords
paper
polymer
hydrocarbon
coating
wax
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
US723654A
Inventor
Daniel D Ritson
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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 American Cyanamid Co filed Critical American Cyanamid Co
Priority to US723654A priority Critical patent/US3015578A/en
Priority to GB9976/59A priority patent/GB845848A/en
Application granted granted Critical
Publication of US3015578A publication Critical patent/US3015578A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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
    • 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
    • Y10T428/31808—Cellulosic is paper

Definitions

  • the present invention relates to coated, impregnated paper. More particularly, the invention relates to paper impregnated with a hydrocarbon liquid or wax and carrying on one side only a grease-resistant polymer coating.
  • wax or hydrocarbon oil impregnated paper carrying a copolymer coating of the type described can be made by a two-step process involving complete immersion of the paper in the hydrocarbon in liquid form.
  • one side of the paper is coated with the polymer.
  • the paper is passed directly into and through a bath of the hydrocarbon in liquid form whereby the entire body of the paper becomes impregnated with the hydrocarbon whi h acts as agent rendering the paper resistant to penetration by water vapor.
  • the invention depends primarily on the discovery that the polymer and the wax are so mutually repellent that even at bath temperatures up to 200 C. the polymer is substantially unaliected by the wax, and substantially none of the wax adheres thereto as the sheet is removed from the bath.
  • the product of the invention is thus paper uniformly impregnated with a non-volatile hydrocarbon solid or liquid and carrying externally on one side only a hard, glossy and grease-resistant polymer coating.
  • the invention does not depend upon the particular way in which the first step is performed.
  • the polymer may be applied in solvent solution form or as a hot melt.
  • application of the copolymer in aqueous emulsion form is preferred, the aqueous content of the emulsion being removed by drying before the paper is passed through the impregnating bath. Enough of the polymer is applied to render the paper grease-resistant, and the necessary amount may be applied as one coating or as a plurality of coatings with intermediate dryings.
  • the product of this step is paper raw stock carrying on one side a hard, flexible, hydrophobic, glossy polymer coating.
  • the paper is immersed in the hydrocarbon bath until at least sufiicient has been absorbed so that the paper when removed from the bath has a low water vapor transmission value.
  • the temperature of the bath should be sufiiciently high so that the hydrocarbon is entirely a liquid of watery viscosity permitting uniform impregnation with rapid elimination of the air content of the paper.
  • the polymer coating is not rendered tacky by the process even at bath temperatures as hi h as 200 F. and thus the paper may be carried down into, through, and out of the bath with the coated side of the paper in direct contact with a steel roll or bar.
  • Paper produced by the foregoing process is illustrated in the attached drawing, which is a schematic crosssection of a sheet produced thereby.
  • 1 represents paper impregnated with a non-volatile hydrocarbon havng a liquefaction point below 200 F.
  • 2 represents the ethyl acrylate-acrylonitrile copolymer coating thereover.
  • the polymer referred to consists essentially of copolymerized acrylonitrile and ethyl acrylate in weight ratio between about 25:75 and 40:60.
  • the copolymer is thus essentially a linear carbon chain or parafiin polymer having nitrile and carbethoxy groups attached thereto. Additional substituent groups may be present for diluent or other purposes such as alkyl, acid, aryl, acetoxy, ketone or chloro groups.
  • the polymers are prepared by copolymerization of appropriate monomer mixtures, and thus these additional groups may be introduced by addition of monomers carrying the desired groups.
  • Suitable monomers include methacrylonitrile, ethyl methacrylate, ethacrylonitrile, etc.; acrylic acid; methacrylic acid, maleic anhydride, maleic acid, ethyl maleate, etc., styrene, p-methyl styrene, p-chloro-methyl styrene, etc., vinyl acetate; vinyl methyl ketone, and vinyl chloride.
  • the number of such substituent groups in the polymer is minor (less than 10% of the number of the nitrile groups plus the carbethoxy groups) and thus the groups do not affect the characterizing properties of the polymer.
  • Hydrophilic radicals particularly carboxy groups are advantageous as these groups increase the contact angle between the hydrocarbon liquid and the polymer on the paper causing the hydrocarbon impregnating agent to flow off more rapidly than would otherwise be the case.
  • the polymer may contain dyes, one or more oil soluble dyes such as Nigrosine Base CF or Acetin Blue and pigments such as phthalocyanine blue and organophilic grade titanium dioxide white so as to provide a colored coating on the paper.
  • dyes one or more oil soluble dyes such as Nigrosine Base CF or Acetin Blue
  • pigments such as phthalocyanine blue and organophilic grade titanium dioxide white so as to provide a colored coating on the paper.
  • the aqueous phase may contain a small amount of trimethyl olmelamine or other water-soluble thermosetting melamine-formaldehyde or urea-formaldehyde condensate.
  • the condensate polymerizes tending to improve the hardness and grease resistance of the coating as a whole.
  • the hydrocarbon liquid used in the impregnation step may be any of the materials heretofore employed for the purpose.
  • the hydrocarbon may be soft pastes or normally liquid, such as petrolatum or the petroleum oil customarily used in the manufacture of loin paper.
  • the hydrocarbon may be a normally solid moderately low melting material such as the parafiin wax customarily used for the manufacture of the semi-transparent waxed paper of commerce. Higher melting paraflin or microcrystalline waxes may be used such as commonly used in manufacture of bread wrap. In general, best resistance to transmission of water vapor occurs when the hydrocarbon used is a wax, and suflicient is left on the sheet to form a continuous coating.
  • the wax may contain pigments, dyes, perfumes and other materials as have heretofore been employed in the manufacture of waxed paper.
  • the paper of the present invention finds principal use for the packaging where moisture vapor resistance and grease resistance are both required. It is suitable for the packaging of meat, fish and materials having a delicate flavor which must be protected, such as cottage cheese and baked goods.
  • Example 1 The following illustrates one method of preparing coated, impregnated paper according to the present invention.
  • Sheets of coating raw stock of 51 lb. basis weight (25" x 38"/500 ream) were coated with an aqueous acrylonitrile-ethyl acrylate emulsion applied at 44% solids by means of a 0.005 Bird applicator. Three coats of emulsion were applied, and the sheets were oven-dried at 220 F. for three minutes after each coat; the total weight of the polymer on the paper was 13 lb. (25" x 38/500 ream).
  • the sheets carried a clear, hard, glossy polymer coating on one side, and were raw paper on the other.
  • the sheets were cut to 5 x 7". Samples were retained as controls and the remainder passed through a bath of paraifin wax (MP. 133135 R); the bath contained a horizontal /2" stainless steel pipe and the sheets were passed under the pipe to efiect complete impregnation, the coated (polymer) side of each sheet being the up side. The sheets showed no tendency to adhere to the pipe.
  • MP. 133135 R paraifin wax
  • the polymer emulsion was prepared by copolymerizing at pH 9 for 6 hours acrylonitrile with ethyl acrylate in 30:70 weight ratio using ammonium persulfate as the catalyst and Duponol C (an anionic high alkyl sulfate) as emulsifier; the emulsion solids was 45%, the remainder being water. The residual monomers were removed by further redox treatment. No emulsion particles were larger than 6 The molecular weight of the polymer by the Staudinger method based on intrinsic viscosity was about 100,000.
  • Example 2 The process of Example 1 was repeated except that the wax bath was replaced by a clear white mineral oil (Nujol) bath at room temperature, and after impregnation the excess oil was doctored ofl.
  • the mineral oil showed no tendency to wet the polymer coating and ran off in the same manner as molten paraffin wax.
  • a sheet was obtained resembling the test sheet material of Example 1, except that the flexibility was greater.
  • Example 3 The procedure of Example 1 was repeated except that the polymer was applied in the form of a 10% by weight solution in anhydrous methyl ethyl ketone. The solution was viscous and was applied to a thickness of about 0.0015 by Bird applicator (three 0.005 coatings with intermediate oven dryin-gs) at 220 F. for 5 minutes to remove solvent. After wax impregnation the sheets closely resembled the sheets of Example 1.
  • Paper according to claim 1 wherein the hydrocarbon is paraffin wax.
  • Process which comprises first coating one side of paper raw stock with a polymer having a molecular Weight in excess of 50,000 consisting essentially of copolymerized acrylonitrile and ethyl acrylate in weight ratio between about 25:75 and 40:60, and then passing the stock carrying said coating through a body of non-volatile liquid hydrocarbon having a liquefaction point below 200 F. thereby impregnating said stock with said hydrocarbon without wetting the polymer coating thereon; whereby a paper is formed which carries externally a hard and glossy grease-resistant coating on one side only, and which is resistant to passage of water vapor therethrough.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)

Description

1962 D. D. RITSON 3,015,578
TWO-SIDED PAPER Filed March 25. 1958 ACRYLONITRILE-ETHYL ACRYLATE (WT. RATIO 2575 TO 40=60) COPOLYMER COATING 2 VOLATILE HYDROCARBON (LIQ.
PT. BELOW 200 F) INVENTOR.
DANIEL D. RITSON ATTORNEY United States Patent Ofiice 3,015,578 Patented Jan. 2, 1962 3,015,578 TWO-SZ'DED PAPER Daniel D. Qitson, Riverside, Conn, assignor to American Cyanamid Company, New York, N.Y., a corporation of Maine Filed Mar. 25, 1958, Ser. N 723,654 6 Claims. (Cl. 117-68) The present invention relates to coated, impregnated paper. More particularly, the invention relates to paper impregnated with a hydrocarbon liquid or wax and carrying on one side only a grease-resistant polymer coating.
it is known that paper coated with a polymer of high molecular weight consisting essentially of a minor amount of acrylonitrile copolymerized with a major amount of ethyl acrylate (or coated with a polymer formed from similar copolymerizable monomers) possesses good resistance to penetration by grease when the grease is applied to the side of the paper carrying the polymer coating. It is further known that paper which has been impregnated with a non-volatile solid or liquid hydrocarbon possesses good resistance to penetration by water vapor.
The discovery has now been made that wax or hydrocarbon oil impregnated paper carrying a copolymer coating of the type described can be made by a two-step process involving complete immersion of the paper in the hydrocarbon in liquid form. In the first step, one side of the paper is coated with the polymer. In the second step, the paper is passed directly into and through a bath of the hydrocarbon in liquid form whereby the entire body of the paper becomes impregnated with the hydrocarbon whi h acts as agent rendering the paper resistant to penetration by water vapor. The invention depends primarily on the discovery that the polymer and the wax are so mutually repellent that even at bath temperatures up to 200 C. the polymer is substantially unaliected by the wax, and substantially none of the wax adheres thereto as the sheet is removed from the bath.
The product of the invention is thus paper uniformly impregnated with a non-volatile hydrocarbon solid or liquid and carrying externally on one side only a hard, glossy and grease-resistant polymer coating.
The invention does not depend upon the particular way in which the first step is performed. Thus the polymer may be applied in solvent solution form or as a hot melt. In practice, application of the copolymer in aqueous emulsion form is preferred, the aqueous content of the emulsion being removed by drying before the paper is passed through the impregnating bath. Enough of the polymer is applied to render the paper grease-resistant, and the necessary amount may be applied as one coating or as a plurality of coatings with intermediate dryings. The product of this step is paper raw stock carrying on one side a hard, flexible, hydrophobic, glossy polymer coating.
In the second step, the paper is immersed in the hydrocarbon bath until at least sufiicient has been absorbed so that the paper when removed from the bath has a low water vapor transmission value. The temperature of the bath should be sufiiciently high so that the hydrocarbon is entirely a liquid of watery viscosity permitting uniform impregnation with rapid elimination of the air content of the paper. The polymer coating is not rendered tacky by the process even at bath temperatures as hi h as 200 F. and thus the paper may be carried down into, through, and out of the bath with the coated side of the paper in direct contact with a steel roll or bar.
As the paper leaves the bath, the hydrocarbon liquid flows completely from the treated side substantially as readily as water flows from a surface treated with paraffin wax. Surface (unadsorbed) hydrocarbon liquid may be removed from the web side by squeeze rolls, air jets or other convenient means, after which the paper is cooled and rolled.
Paper produced by the foregoing process is illustrated in the attached drawing, which is a schematic crosssection of a sheet produced thereby. In the drawing 1 represents paper impregnated with a non-volatile hydrocarbon havng a liquefaction point below 200 F., and 2 represents the ethyl acrylate-acrylonitrile copolymer coating thereover.
The polymer referred to consists essentially of copolymerized acrylonitrile and ethyl acrylate in weight ratio between about 25:75 and 40:60. The copolymer is thus essentially a linear carbon chain or parafiin polymer having nitrile and carbethoxy groups attached thereto. Additional substituent groups may be present for diluent or other purposes such as alkyl, acid, aryl, acetoxy, ketone or chloro groups. The polymers are prepared by copolymerization of appropriate monomer mixtures, and thus these additional groups may be introduced by addition of monomers carrying the desired groups. Suitable monomers include methacrylonitrile, ethyl methacrylate, ethacrylonitrile, etc.; acrylic acid; methacrylic acid, maleic anhydride, maleic acid, ethyl maleate, etc., styrene, p-methyl styrene, p-chloro-methyl styrene, etc., vinyl acetate; vinyl methyl ketone, and vinyl chloride. The number of such substituent groups in the polymer is minor (less than 10% of the number of the nitrile groups plus the carbethoxy groups) and thus the groups do not affect the characterizing properties of the polymer.
Hydrophilic radicals, particularly carboxy groups are advantageous as these groups increase the contact angle between the hydrocarbon liquid and the polymer on the paper causing the hydrocarbon impregnating agent to flow off more rapidly than would otherwise be the case.
The molecular weight of the polymer should be at least about 50,000 to form a film of good flexibility, durability and non-blocking properties.
The polymer may contain dyes, one or more oil soluble dyes such as Nigrosine Base CF or Acetin Blue and pigments such as phthalocyanine blue and organophilic grade titanium dioxide white so as to provide a colored coating on the paper.
When the polymer is applied in emulsion form, the aqueous phase may contain a small amount of trimethyl olmelamine or other water-soluble thermosetting melamine-formaldehyde or urea-formaldehyde condensate. When the paper is heated the condensate polymerizes tending to improve the hardness and grease resistance of the coating as a whole.
The hydrocarbon liquid used in the impregnation step may be any of the materials heretofore employed for the purpose. Thus the hydrocarbon may be soft pastes or normally liquid, such as petrolatum or the petroleum oil customarily used in the manufacture of loin paper. On the other hand, the hydrocarbon may be a normally solid moderately low melting material such as the parafiin wax customarily used for the manufacture of the semi-transparent waxed paper of commerce. Higher melting paraflin or microcrystalline waxes may be used such as commonly used in manufacture of bread wrap. In general, best resistance to transmission of water vapor occurs when the hydrocarbon used is a wax, and suflicient is left on the sheet to form a continuous coating.
The wax may contain pigments, dyes, perfumes and other materials as have heretofore been employed in the manufacture of waxed paper.
The paper of the present invention finds principal use for the packaging where moisture vapor resistance and grease resistance are both required. It is suitable for the packaging of meat, fish and materials having a delicate flavor which must be protected, such as cottage cheese and baked goods.
The invention will be more particularly described with reference to the examples. The examples represent specific embodiments and are not to be construed as limitations thereon.
Example 1 The following illustrates one method of preparing coated, impregnated paper according to the present invention.
Sheets of coating raw stock of 51 lb. basis weight (25" x 38"/500 ream) were coated with an aqueous acrylonitrile-ethyl acrylate emulsion applied at 44% solids by means of a 0.005 Bird applicator. Three coats of emulsion were applied, and the sheets were oven-dried at 220 F. for three minutes after each coat; the total weight of the polymer on the paper was 13 lb. (25" x 38/500 ream). The sheets carried a clear, hard, glossy polymer coating on one side, and were raw paper on the other.
The sheets were cut to 5 x 7". Samples were retained as controls and the remainder passed through a bath of paraifin wax (MP. 133135 R); the bath contained a horizontal /2" stainless steel pipe and the sheets were passed under the pipe to efiect complete impregnation, the coated (polymer) side of each sheet being the up side. The sheets showed no tendency to adhere to the pipe.
As the sheets were pulled from the bath, the wax completely ran oil the polymer coated side without wetting. Excess wax was doctored off the opposite side by means of a smooth metal rod. The treatment did not significantly alter the color, hardness or the gloss of the polymer coatings.
Additional controls were prepared by passing sheets of the raw stock through the parafiin bath without polymer coatings.
The grease resistance values of the samples were deteremed by TAPPI method T454M44 (using turpentine) and the water vapor permeability by the weight increase of calcium chloride in a cup having a top capped with the paper under test. Results are as follows:
1 Turpentine evaporated before penetrating film.
2 At 73 F. and 50% RE.
3 At 100 F. and 90% RH.
The polymer emulsion was prepared by copolymerizing at pH 9 for 6 hours acrylonitrile with ethyl acrylate in 30:70 weight ratio using ammonium persulfate as the catalyst and Duponol C (an anionic high alkyl sulfate) as emulsifier; the emulsion solids was 45%, the remainder being water. The residual monomers were removed by further redox treatment. No emulsion particles were larger than 6 The molecular weight of the polymer by the Staudinger method based on intrinsic viscosity was about 100,000.
Example 2 The process of Example 1 was repeated except that the wax bath was replaced by a clear white mineral oil (Nujol) bath at room temperature, and after impregnation the excess oil was doctored ofl. The mineral oil showed no tendency to wet the polymer coating and ran off in the same manner as molten paraffin wax. A sheet was obtained resembling the test sheet material of Example 1, except that the flexibility was greater.
Example 3 The procedure of Example 1 was repeated except that the polymer was applied in the form of a 10% by weight solution in anhydrous methyl ethyl ketone. The solution was viscous and was applied to a thickness of about 0.0015 by Bird applicator (three 0.005 coatings with intermediate oven dryin-gs) at 220 F. for 5 minutes to remove solvent. After wax impregnation the sheets closely resembled the sheets of Example 1.
I claim: A
1. Paper uniformly impregnated with a non-volatile hydrocarbon having a liquefaction point below 200 F. and carrying externally on one side only a hard and glossy grease-resistant coating of a polymer having a molecular weight in excess of about 50,000 consisting essentially of copolymerized acrylonitrile and ethyl acrylate in weight ratio between about 25:75 and 40:60, said paper being resistant to passage of water vapor therethrough.
2. Paper according to claim 1 wherein the hydrocarbon is paraffin wax.
3. Process which comprises first coating one side of paper raw stock with a polymer having a molecular Weight in excess of 50,000 consisting essentially of copolymerized acrylonitrile and ethyl acrylate in weight ratio between about 25:75 and 40:60, and then passing the stock carrying said coating through a body of non-volatile liquid hydrocarbon having a liquefaction point below 200 F. thereby impregnating said stock with said hydrocarbon without wetting the polymer coating thereon; whereby a paper is formed which carries externally a hard and glossy grease-resistant coating on one side only, and which is resistant to passage of water vapor therethrough.
4. Process according to claim 3 wherein the polymer is applied to the paper as an aqueous emulsion and the paper is dried before it is impregnated with the hydrocarbon.
5. Process according to claim 3 wherein the hydrocarbon is parafiin wax having a melting point between and F.
6. Paper uniformly impregnated with a non-volatile hydrocarbon having a liquefaction point below 200 F. and carrying externally on one side only a hard glossy grease-resistant coating of a polymer having a molecular weight in excess of about 100,000 consisting essentially of copolymerized acrylonitrile, ethyl acrylate and acrylic acid in about 30:65 :5 weight ratio.
References Cited in the file of this patent UNITED STATES PATENTS -n a y

Claims (1)

1. PAPER UNIFORMLY IMPREGNATED WITH A NON-VOLATILE HYDROCARBON HAVING A LIQUEFACTION POINT BELOW 200*F. AND CARRYING EXTERNALLY ON ONE SIDE ONLY A HARD AND GLOSSY GREASE-RESISTANT COATING IF A POLYMER HAVING A MOLECULAR WEIGHT IN EXCESS OF ABOUT 50,000 CONSISTING ESSENTIALLY OF COPOLYMERIZED ACRYLONITRILE AND ETHYL ACRYLATE IN WEIGHT RATIO BETWEEN ABOUT 25:75 AND 40;60, SAID PAPER BEING RESISTANT TO PASSAGE OF WATER VAPOR THERETHROUGH.
US723654A 1958-03-25 1958-03-25 Two-sided paper Expired - Lifetime US3015578A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US723654A US3015578A (en) 1958-03-25 1958-03-25 Two-sided paper
GB9976/59A GB845848A (en) 1958-03-25 1959-03-23 Coated impregnated paper and process of producing same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US723654A US3015578A (en) 1958-03-25 1958-03-25 Two-sided paper

Publications (1)

Publication Number Publication Date
US3015578A true US3015578A (en) 1962-01-02

Family

ID=24907137

Family Applications (1)

Application Number Title Priority Date Filing Date
US723654A Expired - Lifetime US3015578A (en) 1958-03-25 1958-03-25 Two-sided paper

Country Status (2)

Country Link
US (1) US3015578A (en)
GB (1) GB845848A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316123A (en) * 1964-01-28 1967-04-25 American Cyanamid Co Paper carrying non-blocking flexible grease-proof vinyl polymer coating
US3384509A (en) * 1964-09-08 1968-05-21 American Cyanamid Co Paper coated with reaction product of ester resin with amine-aldehyde resin

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US691951A (en) * 1901-05-27 1902-01-28 Cellulose Products Company Water and grease proof paper.
US1766817A (en) * 1924-06-26 1930-06-24 Friedlander Substitute for hard paper, ebonite, fiber, and the like and alpha process for manufacturing the same
US2117349A (en) * 1936-03-12 1938-05-17 Rohm & Haas Esters of acrylic acid
US2290633A (en) * 1940-09-18 1942-07-21 Kelco Co Coated paper and paper products
US2603576A (en) * 1945-11-02 1952-07-15 Arkansas Company Inc Water repellent textiles and method of making same
US2776236A (en) * 1954-03-19 1957-01-01 Eastman Kodak Co Waterproof photographic paper and method of making same
US2873211A (en) * 1955-10-26 1959-02-10 American Marietta Company Ston Carboxylic-nitrile-acrylate ester coating composition, process and coated product

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US691951A (en) * 1901-05-27 1902-01-28 Cellulose Products Company Water and grease proof paper.
US1766817A (en) * 1924-06-26 1930-06-24 Friedlander Substitute for hard paper, ebonite, fiber, and the like and alpha process for manufacturing the same
US2117349A (en) * 1936-03-12 1938-05-17 Rohm & Haas Esters of acrylic acid
US2290633A (en) * 1940-09-18 1942-07-21 Kelco Co Coated paper and paper products
US2603576A (en) * 1945-11-02 1952-07-15 Arkansas Company Inc Water repellent textiles and method of making same
US2776236A (en) * 1954-03-19 1957-01-01 Eastman Kodak Co Waterproof photographic paper and method of making same
US2873211A (en) * 1955-10-26 1959-02-10 American Marietta Company Ston Carboxylic-nitrile-acrylate ester coating composition, process and coated product

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3316123A (en) * 1964-01-28 1967-04-25 American Cyanamid Co Paper carrying non-blocking flexible grease-proof vinyl polymer coating
US3384509A (en) * 1964-09-08 1968-05-21 American Cyanamid Co Paper coated with reaction product of ester resin with amine-aldehyde resin

Also Published As

Publication number Publication date
GB845848A (en) 1960-08-24

Similar Documents

Publication Publication Date Title
US2790736A (en) Methods of making coated paper products and the products obtained
US5247008A (en) Fluorine containing copolymers and aqueous dispersions prepared therefrom
US3037952A (en) Aqueous compositions comprising water insoluble linear polymer and an ammonium salt of a copolymer of methyl methacrylate and acrylic acid monomer and article coated therewith
CN112513370A (en) Oil proofing agent for paper
US2661309A (en) Coated paper and method of producing same
US2990391A (en) Vinylidene chloride-acrylonitrile copolymer in solution of a mixture of tetrahydrofuran and toluene and method of preparing an article therefrom
JP2000154493A (en) Modification of paper substrate
CN114316118A (en) Oil-repellent agent and oil-repellent paper product
US2597087A (en) Synthetic resin coated paper
GB1026850A (en) Improvements in coating process and product
ATE65811T1 (en) LATEX OF A SYNTHETIC POLYMER AND PROCESS FOR MAKING A COATED PAPER WITH LOW GLOSS USING THE LATEX.
US2554663A (en) Method of glossing paper
US3567491A (en) Coating compositions
TWI890873B (en) Oil resistant agent and oil resistant composition
US3048501A (en) Paper products having a coating of mineral pigment in a binder of ammonium or amine salt of a copolymer of acrylic acid or methacrylic acid, acrylamide or methacrylamide, and a (c1-c4)-alkyl acrylate or methacrylate, and production thereof
JPH0317958B2 (en)
US3015578A (en) Two-sided paper
US2554662A (en) Process of glossing paper
US2945775A (en) Sizing of paper with acrylamide polymers
US2889299A (en) Grease resistant cellulosic webs coated with a linear anionic thermoplastic ethyl acrylate-acrylonitrile-methacrylic acid polymer containing a hydrophilic inorganic pigment as extender and composition for manufacture thereof
JP2756099B2 (en) Method for producing polymer containing hydrocarbon wax
DE1925091B2 (en) AQUATIC DISPERSION ON THE BASIS OF AETHYLENE MIXED POLYMERISATES AND THEIR USE
US3136652A (en) Method and apparatus for coating paper
US3298855A (en) Moisture-resistant wrapping paper
JP3274001B2 (en) Method for producing paperboard and paperboard obtained by the method