US2488515A - Utilization of waste wax paper - Google Patents

Utilization of waste wax paper Download PDF

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US2488515A
US2488515A US59310445A US2488515A US 2488515 A US2488515 A US 2488515A US 59310445 A US59310445 A US 59310445A US 2488515 A US2488515 A US 2488515A
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wax
paper
amino
broke
acid
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Laurence R Sherman
Benson W Ronald
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James River Corp of Nevada
Nopco Chemical Co
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Nopco Chemical Co
Crown Zellerbach Corp
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Priority to BE478756D priority Critical patent/BE478756A/xx
Priority to BE464980D priority patent/BE464980A/xx
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Priority to US59310445 priority patent/US2488515A/en
Priority to GB1302146A priority patent/GB615254A/en
Priority to FR926742D priority patent/FR926742A/en
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    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21CPRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
    • D21C5/00Other processes for obtaining cellulose, e.g. cooking cotton linters ; Processes characterised by the choice of cellulose-containing starting materials
    • D21C5/02Working-up waste paper
    • D21C5/022Chemicals therefor
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02WCLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00Technologies for solid waste management
    • Y02W30/50Reuse, recycling or recovery technologies
    • Y02W30/64Paper recycling

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  • the present invention relates to the reclaiming and utilization of waste wax' paper. More particularly the present invention relates tothe utilization of wax cuttings and the like known in the art as wax broke for the manufacture of any other type of paper either alone or in admixture with additional wood fiberor other forms of paper.
  • a second object of the present invention is to provide a novel process which includes fixing the wax derived from wax broke directly on the fibers in such a manner that no wax deposits are formed in the paper making machinery or wax spots in the finished sheet.
  • a suitable quantity of wax broke is charged into a beater or other paper making apparatus capable of disintegrating the same. Thereafter the beater is heated to a temperature sufflcient to melt the wax.
  • the heater is brought to a temperature above this point, such as ap-' proximately -160 F., by the use of steam or by other heating means.
  • a cationic surface active material of the type hereinafter to she described is added to the proportion of at least 3% by weight of the wax.
  • the cationic sub.- stance apparently fixes the residual wax on the fibers and permits the use of the so-treated broke in paper manufacture in the usual manner.
  • the cationic surface active agents used in accordance with the present invention include cer.. tain amino-amides, glyoxalidines cyclized from those amino-amides, and the solubilized derivatives of either.
  • the amino-amides may best be described by the general formula:
  • R represents an aliphatic chain containing from 7 to 23 carbon atoms
  • R denotes a substituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbons
  • n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting ofl, 2 and 3 when R represents an alkylol radical.
  • Glyoxalidines may be formed from amino-amides of the above formula by internal condensation wherein the carboxyl carbon assault atom of the amide group is linked to the nitrogen atom of the nearest amino group in the molecule. This glyoxalidine ring formation occurs when the oxygen and hydrogen atoms of the amido group combine with a hydrogen.
  • compounds corresponding to soluble acid salts or alkylated derivatives of the above type of compound may be used. These may be produced by treating a compound of the general formula above described with an aliphatic monocarboxyiic acid of from 1 to 3 carbon atoms such as acetic, formic, glycolic, etc. or with a suitable ester of a mineral acid, as, for example, diethyl sulfate, triethyl phosphate, ethyl iodide, etc.
  • the resultant solubilized compounds may then be illustrated by the general formula;
  • R R and n have the values assigned of the respective residues of said acid and said ester; and where the formula also encompasses the same derivatives of glyoxalidines produced from the amino-amides prior to addition of the R and Z radicals by linking the carboxyl carbon atom with thenitrogen atom of the nearest amino group accompanied by liberation of a molecular proportion of water.
  • a suitable fat or fatty acid is reacted with a polyalkylene polyamine compound in order to form an amino-amide, or in the alternative, the fatty acid or fat is reacted with an alkylene alkylol polyamine or a polyalkylene alkylol polyamine compound.
  • the amino-amide may be heated to a relatively high temperature to drive oil water in order to form a cyclic compound.
  • the amino-amide, or the cyclic glyoxalidine compound equivalent to the amino-amide may then be treated with an agent rendering the compound water soluble, such as a suitable ester of a mineral acid, for example, diethyl sulphate, triethyl phosphate, ethyl iodide, or an aliphatic monocarboxylic acid of from 1 to 3 carbon atoms such as acetic, formic, glycolic, etc. or the amide or glyoxalidine may be added first to the paper fibers and wax and thereafter the acid.
  • an agent rendering the compound water soluble such as a suitable ester of a mineral acid, for example, diethyl sulphate, triethyl phosphate, ethyl iodide, or an aliphatic monocarboxylic acid of from 1 to 3 carbon atoms such as acetic, formic, glycolic, etc. or the amide or glyoxalidine may be added first to the
  • temperatures in the neighborhood of 200 C. or from 150 to 210 C. are utilized for the amidification, and in the event the cyclic compound is desired, temperatures in the neighborhood of 300 C. are used.
  • Various polyalkylene polyamine, alkylene alkylol polyamine or polyalkylene alkylol polyamine compounds having from 2 to 4 amino groups may be used as, for example, diethylene triamine, ethanol ethylene diamine, ethanol diethylene triamine, triethylene tetramine, etc.
  • Almost any fatty acid or fatty acid glyceride having from 8 to 24 carbon atoms in the chain may be utilized as the fatty acid portion of the compound.
  • olelc acid, ricinoleic acid, lauric acid, stearic acid, palmitic acid, etc. are examples of the fatty acids which may be utilized in preparing the amino-amide compound.
  • Example I 74.8 parts by weight of hydrogenated soybean oil and 25.2 parts of ethanol ethylene diamine were condensed in a closed vessel at 150 C. for from 6 to 8 hours.
  • the product was believed to consist largely of an amino-amide having the following formula:
  • Example II 78.3 parts by weight of peanut oil and 27.5 parts by weight of diethylene triamine were heated together to a temperature of about C. in a closed vessel and held at this temperature for about 6 to 8 hours. Thereafter the amino-amide was added to wax broke in a beater as set forth in Example I. The only difference in the procedure being that after the amino-amide was added to the wax broke and water at 140 F. and beating continued for about 30 minutes, sufilcient acetic acid to bring the pH of the slurry from pH 8 to pH 6 was added and the slurry was again beaten for about 30 minutes. Sheets made from this slurry were also entirely satisfactory and no wax deposits in the beater were observed.
  • Example III 78.3 parts by weight of peanut oil and 27.5 parts by weight of diethylene triamine were heated together to a temperature of between and C. and held at this temperature for 20 minutes. Thereafter the reaction mixture was rapidly heated to 300 C. and the evolved water was collected ina moisture trap. when 5.8 parts of aqueous condensate were collected, the heat washut off and the product allowed to cool.
  • the resultant product was believed to have the followins formula:
  • R represents an aliphatic chain containing from 7 to 23 carbon atoms
  • R denotes a sub- 1 stituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbon atoms
  • n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting'of 1, 2 and 3 when R represents an alkylol radical
  • R denotes a substituent selected from the group consisting respectively of hydrogen, when R-"Z is a 1 to 3 carbon aliphatic monocarboxylic acid, and an aliphatic alkyl group of from 1 to 3 carbon atoms
  • R 2 is an ester of a mineral acid with a 1 to 3 carbon aliphatic alcohol
  • Z is selected from the group consisting of the respective residues of said acid and said ester.
  • a process for reciaiming wax paper broke consisting of forming a suspension in water of the fibers of the waxbroke by disintegrating the broke in water heated to a temperature sufliciently high to melt the wax, and fixing the wax on the fibers by adding a cationic surface active substance to the fiber and wax suspension and thereafter adding an aliphatic rnonocarboxylic acid containing from 1 to 3 carbon atoms per molecule to the suspension to reduce the pH value to approximately 6, said cationic substance being selected from the group consisting of aminoamides having the general formula:
  • R represents an aliphatic chain containing from 7 to 23 carbon atoms
  • R denotes a substituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbon atoms
  • n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting of 1, 2 and 3 when 1'1. represents an alkylol radical.
  • a process for reclaiming wax paper broke consisting of forming a suspension in water of the fibers of the wax paper broke by disintegrating the broke in water heated to a tern perature sumciently high to melt the wax, and fixing the wax on the fibers by adding the acetic acid solubilized derivative of ethanol amino ethylene stearamide to the suspension.
  • a process for reclaiming wax paper broke consisting of. forming a suspension in water of the fibers of the wax paper broke by disintegrating the broke in water heated to a temperature sufiiciently high to melt the wax, and fixing the wax on the fibers by adding ethanol amino ethylene stearamide to the suspension and thereafter adding acetic acid to the suspension.

Description

Patented Nov.15,1949
UTILIZATION OF WASTE WAX PAPE Laurence n. Sherman, Glens Falls, N. Y., and
W. Ronald Benson, Seattle, Wash., assignors of one-half to Nopco Chemical Company, a corporation of New Jersey and one-half to Crown Zellerbach Corporation, San Francisco, Calif.I a corporation of Nevada No Drawing. Application May 10,1945, Serial No. 593,104
6 Claims. (Cl. -92L6) The present invention relates to the reclaiming and utilization of waste wax' paper. More particularly the present invention relates tothe utilization of wax cuttings and the like known in the art as wax broke for the manufacture of any other type of paper either alone or in admixture with additional wood fiberor other forms of paper.
Utilization of waste wax paper, wax trimmings and the like has been a considerable problem in the art inasmuch as the wax on this paper would 'and gradually raising the temperature of the water to a point above the melting point of the wax. Thereafter an emulsifier is added which consists primarily of a mixture of sulfonated oils, such as sulfonated olive oil, cottonseed oil, sperm oil, etc. with mahogany soaps. Although this process has been found commercially acceptable for reclaiming and reusing wax broke, the resultant fibers have not been generally capable of use in any except the heavier forms of paper manufacture. Furthermore, during warm weather at times wax deposits on the screens and other portions of the paper making apparatus would cause trouble.
In accordance with the present process, however, it has been discovered that this action may be prevented if the wax broke is treated after heating with a suitable proportion of a cationic surface active agent of the character to be hereinafter described. The action of the cationic matter appears to be entirely dissimilar to that of the emulsifying gents disclosed in the aforementioned patent in that no true emulsion of the wax is formed and the wax cannot be washed from the paper fibers. Instead the wax and fibers with the wax fixed thereon can be used either by themselves to form sheets or. in the event such a high proportion of wax size is not desired, the fibers may be combined with other paper fibers or other forms of fiber in any suitable proportion.
It is one of the objects of the invention, therefore, to provide a novel process for the utilization of wax paper waste, 1. e. wax broke.
A second object of the present invention is to provide a novel process which includes fixing the wax derived from wax broke directly on the fibers in such a manner that no wax deposits are formed in the paper making machinery or wax spots in the finished sheet.
Other objects and advantages of the present invention will become apparent from the present description and claims.
In practicing the present process a suitable quantity of wax broke is charged into a beater or other paper making apparatus capable of disintegrating the same. Thereafter the beater is heated to a temperature sufflcient to melt the wax. Inasmuch as the type of wax used in making waste paper generally has a melting point of approximately F., the heater is brought to a temperature above this point, such as ap-' proximately -160 F., by the use of steam or by other heating means. Thereafter a cationic surface active material of the type hereinafter to she described is added to the proportion of at least 3% by weight of the wax. The cationic sub.- stance apparently fixes the residual wax on the fibers and permits the use of the so-treated broke in paper manufacture in the usual manner.
The cationic surface active agents used in accordance with the present invention include cer.. tain amino-amides, glyoxalidines cyclized from those amino-amides, and the solubilized derivatives of either. The amino-amides may best be described by the general formula:
wherein R represents an aliphatic chain containing from 7 to 23 carbon atoms; R denotes a substituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbons, and n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting ofl, 2 and 3 when R represents an alkylol radical. Glyoxalidines may be formed from amino-amides of the above formula by internal condensation wherein the carboxyl carbon assault atom of the amide group is linked to the nitrogen atom of the nearest amino group in the molecule. This glyoxalidine ring formation occurs when the oxygen and hydrogen atoms of the amido group combine with a hydrogen. atom of the nearest amino group thereby liberating a molecule of water. Further, compounds corresponding to soluble acid salts or alkylated derivatives of the above type of compound may be used. These may be produced by treating a compound of the general formula above described with an aliphatic monocarboxyiic acid of from 1 to 3 carbon atoms such as acetic, formic, glycolic, etc. or with a suitable ester of a mineral acid, as, for example, diethyl sulfate, triethyl phosphate, ethyl iodide, etc. The resultant solubilized compounds may then be illustrated by the general formula;
where R R and n have the values assigned of the respective residues of said acid and said ester; and where the formula also encompasses the same derivatives of glyoxalidines produced from the amino-amides prior to addition of the R and Z radicals by linking the carboxyl carbon atom with thenitrogen atom of the nearest amino group accompanied by liberation of a molecular proportion of water.
In preparing the cationic compound which fixes the residual wax on the fibers in accordance with the present invention, a suitable fat or fatty acid is reacted with a polyalkylene polyamine compound in order to form an amino-amide, or in the alternative, the fatty acid or fat is reacted with an alkylene alkylol polyamine or a polyalkylene alkylol polyamine compound. Thereafter, the amino-amide may be heated to a relatively high temperature to drive oil water in order to form a cyclic compound. The amino-amide, or the cyclic glyoxalidine compound equivalent to the amino-amide, may then be treated with an agent rendering the compound water soluble, such as a suitable ester of a mineral acid, for example, diethyl sulphate, triethyl phosphate, ethyl iodide, or an aliphatic monocarboxylic acid of from 1 to 3 carbon atoms such as acetic, formic, glycolic, etc. or the amide or glyoxalidine may be added first to the paper fibers and wax and thereafter the acid.
In general, temperatures in the neighborhood of 200 C. or from 150 to 210 C. are utilized for the amidification, and in the event the cyclic compound is desired, temperatures in the neighborhood of 300 C. are used. Various polyalkylene polyamine, alkylene alkylol polyamine or polyalkylene alkylol polyamine compounds having from 2 to 4 amino groups may be used as, for example, diethylene triamine, ethanol ethylene diamine, ethanol diethylene triamine, triethylene tetramine, etc. Almost any fatty acid or fatty acid glyceride having from 8 to 24 carbon atoms in the chain may be utilized as the fatty acid portion of the compound. Thus, olelc acid, ricinoleic acid, lauric acid, stearic acid, palmitic acid, etc. are examples of the fatty acids which may be utilized in preparing the amino-amide compound.
The following specific examples, wherein all proportions are expressed in terms of weight. serve to. illustrate but are not intended to limit the present invention.
Example I 74.8 parts by weight of hydrogenated soybean oil and 25.2 parts of ethanol ethylene diamine were condensed in a closed vessel at 150 C. for from 6 to 8 hours. The product was believed to consist largely of an amino-amide having the following formula:
OuHa-C CzIhOE .Thereafter 17.4 parts of the above amino-amide were placed in a stainless steel vessel and melted. A mixture of 3.7 parts of 70% acetic acid and 78.9 parts of water preliminarily heated to 85 C. were then added to the melt and the entire mass stirred until a homogeneous gel formed. This gel was believed to contain substantial amounts of a compound having the formula:
500 grams of waste wax cuttings containing approximately l2% wax were slowly charged into a Valley 1 pound Niagara beater containing 2300 grams of water at F. Three grams of the cationic agent produced as above set forth were then added and the heating continued with a one pound weight on the lever arm of the beater while heating with steam to a temperature of F. The time of heating and heating was approximately 30 minutes. No scum formed on the surface and no wax break appeared when a small amount of the suspension was poured into cold water. Thereafter hand sheets were made from the suspension of fibers and wax. These sheets had a good appearance and were entirely free from wax spots and the like.
Example II 78.3 parts by weight of peanut oil and 27.5 parts by weight of diethylene triamine were heated together to a temperature of about C. in a closed vessel and held at this temperature for about 6 to 8 hours. Thereafter the amino-amide was added to wax broke in a beater as set forth in Example I. The only difference in the procedure being that after the amino-amide was added to the wax broke and water at 140 F. and beating continued for about 30 minutes, sufilcient acetic acid to bring the pH of the slurry from pH 8 to pH 6 was added and the slurry was again beaten for about 30 minutes. Sheets made from this slurry were also entirely satisfactory and no wax deposits in the beater were observed.
Example III 78.3 parts by weight of peanut oil and 27.5 parts by weight of diethylene triamine were heated together to a temperature of between and C. and held at this temperature for 20 minutes. Thereafter the reaction mixture was rapidly heated to 300 C. and the evolved water was collected ina moisture trap. when 5.8 parts of aqueous condensate were collected, the heat washut off and the product allowed to cool. The resultant product was believed to have the followins formula:
N-cm \[TT- H:
CgHsNH: where R represents the alkyl radicals of peanut oil.
500 grams of waste cuttings were treated with the above cationic agent in a manner similar to that of Example 1. The. resulting hand-made sheets were entirely satisfactory and free from wax spots.
Having described our invention, what we claim as new and desire to secure by LettersPatent is:
1. A process for reclaiming wax paper broke,
the steps consisting of forming a suspension in where R represents an aliphatic chain containing from 7 to 23 carbon atoms, R denotes a sub- 1 stituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbon atoms, and n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting'of 1, 2 and 3 when R represents an alkylol radical, R denotes a substituent selected from the group consisting respectively of hydrogen, when R-"Z is a 1 to 3 carbon aliphatic monocarboxylic acid, and an aliphatic alkyl group of from 1 to 3 carbon atoms, when R 2 is an ester of a mineral acid with a 1 to 3 carbon aliphatic alcohol, and Z is selected from the group consisting of the respective residues of said acid and said ester.
2. A process according to claim 1 in whichthe quantity of said cationic surface active substance added is at least 3% of the weight of the was present in the suspension.
3. A process for reciaiming wax paper broke, the steps consisting of forming a suspension in water of the fibers of the waxbroke by disintegrating the broke in water heated to a temperature sufliciently high to melt the wax, and fixing the wax on the fibers by adding a cationic surface active substance to the fiber and wax suspension and thereafter adding an aliphatic rnonocarboxylic acid containing from 1 to 3 carbon atoms per molecule to the suspension to reduce the pH value to approximately 6, said cationic substance being selected from the group consisting of aminoamides having the general formula:
where R represents an aliphatic chain containing from 7 to 23 carbon atoms, R denotes a substituent selected from the group consisting of hydrogen and alkylol groups containing 1 to 3 carbon atoms, and n is a number selected from the group consisting of 2 and 3 when R stands for hydrogen and n is a number selected from the group consisting of 1, 2 and 3 when 1'1. represents an alkylol radical.
4. A process for reclaiming wax paper broke, the steps consisting of forming a suspension in water of the fibers of the wax paper broke by disintegrating the broke in water heated to a tern perature sumciently high to melt the wax, and fixing the wax on the fibers by adding the acetic acid solubilized derivative of ethanol amino ethylene stearamide to the suspension.
5. A process for reclaiming wax paper broke, the steps consisting of. forming a suspension in water of the fibers of the wax paper broke by disintegrating the broke in water heated to a temperature sufiiciently high to melt the wax, and fixing the wax on the fibers by adding ethanol amino ethylene stearamide to the suspension and thereafter adding acetic acid to the suspension.
6. A process according to claim 5 in which the quantity of ethanol amino ethylene stearamide added is at least 3% of the weight of the wax present in the suspension.
LAURENCE R. SHERMAN. W. RONALD BENSON.
REFERENCES CITED UNITED STATES PATENTS Number Name Date 1,970,426 Levin Aug. 14, 1934 1,992,589 Tucker Feb. 26, 1935 2,096,129 Neitzke Oct. 19, 1937 2,183,259 Hill Dec. 12, 1939 2,186,609 Kress Jan. 9, 1940 2,206,090 Haggenmacher July 2, 1940 2,268,273 Wilkes Dec. 30, 1941 2,277,788 Shipp Mar. 31, 1942 2,343,090 Smith Feb. 29, 1944 2,343,095 Smith Feb. 29, 1944 2,347,178 Fritz et al Apr. 25, 1944 I 2,401,027 Tausch May 28. 1946 2,442,972 Edelstein June 8, 1948 FOREIGN PATENTS Number Country Date 319,745 Great Britain Dec. 29, 1930 OTHER REFERENCES Technical Association Papers, Series 22, pp. 264-267 (1939).
Paper Trade Journal, Aug. 22, 1940, pp. 30, 31. Rayon Textile Monthly, Mar. 1944, p. 79. Journal of Society Chemical Industries, Apr. .1938, p. 117. 4
Paper Trade Journal, June 29, 1944, pp. 27-32. Industrial and Engineering Chemistry, Jan. 1M1) PP. 16-32,
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BE464980D BE464980A (en) 1945-05-10
US59310445 US2488515A (en) 1945-05-10 1945-05-10 Utilization of waste wax paper
GB1302146A GB615254A (en) 1945-05-10 1946-04-30 Improvements relating to the reclaiming of waste wax paper
FR926742D FR926742A (en) 1945-05-10 1946-05-09 Wax paper waste regeneration process

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Cited By (9)

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US2563897A (en) * 1945-07-13 1951-08-14 American Cyanamid Co Sizing cellulosic fibers with cationic melamine resin and hydrophobic material
US2601671A (en) * 1946-10-23 1952-06-24 American Cyanamid Co Resin-impregnated leather board
US2686121A (en) * 1948-07-07 1954-08-10 Morton Chemical Co Process of loading cellulosic fibers
US2694633A (en) * 1950-02-23 1954-11-16 Talbott Dev Associates Affixing organic and inorganic additaments to cellulosic materials
US2745744A (en) * 1951-02-09 1956-05-15 Permacel Tape Corp Treating agents incorporation
US3021252A (en) * 1960-03-31 1962-02-13 Lawrence Paper Co Process of making wax-containing paper using waste wax paper
US3819470A (en) * 1971-06-18 1974-06-25 Scott Paper Co Modified cellulosic fibers and method for preparation thereof
WO1986002116A1 (en) * 1984-10-01 1986-04-10 Dalkiaer Peter A process for manufacturing a liquid absorbing pad, in particular for use in soft hygiene articles and sanitary products
US4735682A (en) * 1985-02-21 1988-04-05 James River-Norwalk, Inc. Method for recovery of cellulosic fibers containing latex solids from latex bonded broke

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US4997523A (en) * 1990-06-20 1991-03-05 Betz Panerchem, Inc. Method for effectively breaking up latex-coated paper during pulping to decrease the potential for white pitch deposition

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US1992589A (en) * 1931-04-17 1935-02-26 Dewey And Almy Chem Comp Organic fiber and method of preparing same
US2096129A (en) * 1936-02-24 1937-10-19 Bennett Inc Manufacture of sized papers
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US2268273A (en) * 1939-05-27 1941-12-30 Carbide & Carbon Chem Corp Textile finishing
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US2343090A (en) * 1940-08-03 1944-02-29 Du Pont Treatment of textiles and composition useful therefor
US2343095A (en) * 1940-08-03 1944-02-29 Du Pont Resin dispersion useful in the textile and paper industries
US2347178A (en) * 1942-01-07 1944-04-25 Nat Oil Prod Co Reversible emulsion and application therefor
US2401027A (en) * 1942-10-21 1946-05-28 American Anode Inc Deposition of rubber from aqueous dispersions of rubber
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GB319745A (en) * 1928-09-27 1930-12-29 Albert Lewis Clapp Manufacture of waterproof fibrous products
US1970426A (en) * 1930-01-22 1934-08-14 Paten And Licensing Corp Paper making process
US1992589A (en) * 1931-04-17 1935-02-26 Dewey And Almy Chem Comp Organic fiber and method of preparing same
US2096129A (en) * 1936-02-24 1937-10-19 Bennett Inc Manufacture of sized papers
US2183259A (en) * 1937-03-03 1939-12-12 Nat Oil Prod Co Process for recovering and reusing constituents of waxed paper
US2186609A (en) * 1937-05-05 1940-01-09 Paper Chemistry Inst Method of removing wax from waxed paper stock
US2206090A (en) * 1937-05-17 1940-07-02 Warwick Chemical Co Waterproofing composition and similar emulsion
US2268273A (en) * 1939-05-27 1941-12-30 Carbide & Carbon Chem Corp Textile finishing
US2277788A (en) * 1940-08-03 1942-03-31 Du Pont Treatment of textiles and composition useful therefor
US2343090A (en) * 1940-08-03 1944-02-29 Du Pont Treatment of textiles and composition useful therefor
US2343095A (en) * 1940-08-03 1944-02-29 Du Pont Resin dispersion useful in the textile and paper industries
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US2347178A (en) * 1942-01-07 1944-04-25 Nat Oil Prod Co Reversible emulsion and application therefor
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2563897A (en) * 1945-07-13 1951-08-14 American Cyanamid Co Sizing cellulosic fibers with cationic melamine resin and hydrophobic material
US2601671A (en) * 1946-10-23 1952-06-24 American Cyanamid Co Resin-impregnated leather board
US2686121A (en) * 1948-07-07 1954-08-10 Morton Chemical Co Process of loading cellulosic fibers
US2694633A (en) * 1950-02-23 1954-11-16 Talbott Dev Associates Affixing organic and inorganic additaments to cellulosic materials
US2745744A (en) * 1951-02-09 1956-05-15 Permacel Tape Corp Treating agents incorporation
US3021252A (en) * 1960-03-31 1962-02-13 Lawrence Paper Co Process of making wax-containing paper using waste wax paper
US3819470A (en) * 1971-06-18 1974-06-25 Scott Paper Co Modified cellulosic fibers and method for preparation thereof
WO1986002116A1 (en) * 1984-10-01 1986-04-10 Dalkiaer Peter A process for manufacturing a liquid absorbing pad, in particular for use in soft hygiene articles and sanitary products
US4735682A (en) * 1985-02-21 1988-04-05 James River-Norwalk, Inc. Method for recovery of cellulosic fibers containing latex solids from latex bonded broke

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BE478756A (en) 1900-01-01
FR926742A (en) 1947-10-09
GB615254A (en) 1949-01-04
BE464980A (en) 1900-01-01

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