US2165265A - Process of imparting hydrophobic properties to cellulose fibers - Google Patents

Process of imparting hydrophobic properties to cellulose fibers Download PDF

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US2165265A
US2165265A US81122A US8112236A US2165265A US 2165265 A US2165265 A US 2165265A US 81122 A US81122 A US 81122A US 8112236 A US8112236 A US 8112236A US 2165265 A US2165265 A US 2165265A
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fibers
acid
cellulose fibers
solution
formaldehyde
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Hubert Franz Emil
Heisenberg Erwin
Steindorff Adolf
Orthner Ludwig
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IG Farbenindustrie AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/41—Phenol-aldehyde or phenol-ketone resins
    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/17—Glyoxal and polyaldehyde treatment of textiles
    • 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2904—Staple length fiber
    • Y10T428/2907—Staple length fiber with coating or impregnation

Definitions

  • the present invention relates to a process of imparting hydrophobic properties to cellulose fibers.
  • fibers of cellulose or hydrated 5 cellulose such as cotton, artificial silk or staple fiber are extraordinarily hydrophil, that is to say they are very quickly wetted when in contact with water. This property is a great disadvantage for many of the applications of this material.
  • This invention consists in a process for making cellulose fibers hydrophobe by applying to the fibers or incorporating with them a compound which contains at least one aliphatic or cycloaliphatic residue having at least 4 carbon atoms and capable of reacting with aldehyde and exposing the fibers thus treated simultaneously or subsequently to the action of an aliphatic aldehyde or dialdehyde, for instance, formaldehyde or glyoxal.
  • Suitable aliphatic compounds are, for example,
  • fatty amines and fatty acid amides such as dodecylamine, hexadecylamine, octadecenylamine, abietic acid amide, lauric acid amide, stearoyl-methylamide, stearoyl-butylamide, stearoyloctadecylamide; further compounds of the character of alkyl-substituted ureas having the general formula:
  • R. stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms
  • X 35 stands for a member selected from the group consisting of O, NH, N. alkyl
  • R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, such as mono-isobutyl urea, monododecyl urea, monooctadecyl urea, stearoyl urea; further fatty acid imino ethers or arnidines.
  • hydroxyl groups such as, for instance, dodecylphenol, diisohexyl-phenol.
  • the cellulose fibers are first saturated with a solution of the aliphatic compound in an organic solvent, for instance, pyridine, or acetone 55 or in an aqueous emulsion of the aliphatic compounds. They are then dried and exposed to the atcion of, for instance, formaldehyde, the concentration of which, when it is used in the form of a solution, must not be more than 5%.
  • formaldehyde may be added to the impregnating solution so that a subsequent treatment with formaldehyde becomes unnecessary; however, care must likewise be taken that the concentration of the aldehyde, for instance, of the formaldehyde, in the treating solution is not more than 5%. In this case the fiber needs only subsequent heating to ensure sufiicient reaction of the formaldehyde with the impregnating compound and the fiber.
  • an acid medium there may be added, for example, to the aqueous emulsion, acetic acid, lactic acid or agents of acid reaction such' as sodium bisulfite.
  • Fibers treated in this manner are characterized by a particularly high stability towards-water and even hot soap solution.
  • such material can be subjected to the usual fulling treatment, that is to say heating for A; hour in a. solution of 50 grams of soap and 5 grams of sodium carbonate per liter at 50 C. without loss of the property of repellent water.
  • the parent material and working conditions an effect can be obtained which is not notably diminished by several washings with boiling soap solution.
  • Another process of rendering cellulose fibers water-repellent consists in treating the fibers with solutions or dispersions of the aldehyde condensation products.
  • a catalyst an acid substance is suitably added to the solutions or dispersions.
  • the fibers may also be pretreated withan acid substance.
  • the said aldehyde condensation products may also be added directly to the spinning solutions from which the artifical cellulose threads are prepared.
  • the fibers which are prepared from solutions containing such an addition may, if required, be treated subsequently with an aldehyde.
  • the silk is then drained, dried, immersed for 5 minutes in aqueous formaldehyde solution of 30 per cent. strength, centrifuged, dried and heated for 16 hours at C.
  • aqueous formaldehyde solution of 30 per cent. strength
  • centrifuged dried and heated for 16 hours at C.
  • the fibrous material may be suspended for hour in a chamber charged with formaldehyde vapor at C.
  • octadecyl-heptadecyl urea another of the substances specified above may be used.
  • Unsoaped dry viscose silk is immersed for 5 minutes in 10 times its weight of an aqueous emulsion containing 2 per cent. of stearin-amide, 0.2 per cent. of an emulsifying agent, obtainable by the reaction of ethylene-oxide with octadecenyl-alcohol, and0.3 per cent. of formaldehyde.
  • the goods are centrifuged, dried and heated for 6 hours at 110 C. A subsequent washing is not necessary.
  • Unsoaped, dry viscose silk is immersed for 5 minutes in 5 times its weight of a solution of 5-10 per cent. strength of methylol-stearinamide in pyridine.
  • the goods are centrifuged, dried and heated for 15 hours at 110 C.
  • Example 4 The operation is conducted as described in Example 2 but 7 per cent. of lactic acid is added to the emulsion. By this addition of acid the stability of the water repelling preparation is strongly increased, particularly towards treatment with boiling dilute acid.
  • Dry viscose artificial silk is treated for 15 minutes with a solution of 5 grams of a condensation product, obtainable from stearic acid amide and aqueous formaldehyde, in 1 liter of carbon tetrachloride.
  • the material is squeezed and dried in the air. Thereupon it is aftertreated at room temperature for 15 minutes with [I a solution of 5 grams of lactic acid in 1 liter of water, squeezed, dried in a current of air and heated for 2 hours at 110 C. The material is finally well rinsed and dried.
  • Viscose artificial silk tissue is treated for 10 minutes with an aqueous solution of the sodium salt of stearyl aminomethanesulfonic acid or stearylmethylaminomethanesulfonic acid, 5 grams of lactic acid being added per liter.
  • the material is squeezed and dried at a temperature of 40 C. to 50 C.
  • the tissue is then heated for 5-10 minutes at a temperature of C. to C.
  • cellulose fibers of all kinds for instance, copper artificial silk, artificial spinning fibers, cotton, also mixtures of wool and cellulose fibers as well as fabrics made from the said fibers and mixtures of fibers may be used. In some cases a preliminary cleansing or desizing of the fibers or fabric is advisable.
  • R star ids for a radical selected from the group consisting of aliphatic and ,cycloali phatic radicals containing at least 4 carbon atoms
  • X stands for a member selected from the group consisting of O, NH, N.alkyl
  • R1 stands for a member of the group consisting of hydrogen and, aliphatic hydrocarbon radicals, at most 5 per cent. of aldehyde and an agent of acid action, and heating them after the impregnation.
  • R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals, containing at least '4 carbon atoms, x
  • R1 stands for a radical selected from the group consisting of O, NH, N.alkyl and R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, treating the fibers with aliphatic aldehydes and subsequently heating them.
  • R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms,'X
  • R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms
  • X stands for a radical selected from the group consisting of 0, NH, N.alky1
  • R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, in the presence of an agent of acid action, and heating them after the impregnation.

Description

Patented July 11, 1939 UNITED STATES PROCESS OF IMPARTING HYDROPI IOBIC PROPERTIES T CELLULOSE FIBERS Franz Emil, Hubert, Dessau-Zlebigk, Erwin Heisenberg, LcipIlI, and Adolf Steindoril. and Ludwig ortlincr, Frankfort-on-the-Maln,
Ger-
many, assignors to I. G. Farbenindustrie Aktlengesellschait, Frankfort on-the-Main, Germany No Drawing. Application May 21,- 1936, Serial 7 No. 81,122. In Germany May 11, 1935;
Claims.. (Cl. 91'l0) The present invention relates to a process of imparting hydrophobic properties to cellulose fibers.
It is known that fibers of cellulose or hydrated 5 cellulose, such as cotton, artificial silk or staple fiber are extraordinarily hydrophil, that is to say they are very quickly wetted when in contact with water. This property is a great disadvantage for many of the applications of this material.
This invention consists in a process for making cellulose fibers hydrophobe by applying to the fibers or incorporating with them a compound which contains at least one aliphatic or cycloaliphatic residue having at least 4 carbon atoms and capable of reacting with aldehyde and exposing the fibers thus treated simultaneously or subsequently to the action of an aliphatic aldehyde or dialdehyde, for instance, formaldehyde or glyoxal.
v Suitable aliphatic compounds are, for example,
fatty amines and fatty acid amides such as dodecylamine, hexadecylamine, octadecenylamine, abietic acid amide, lauric acid amide, stearoyl-methylamide, stearoyl-butylamide, stearoyloctadecylamide; further compounds of the character of alkyl-substituted ureas having the general formula:
/H R.X.CO.N
wherein R. stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms, X 35 stands for a member selected from the group consisting of O, NH, N. alkyl, and R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, such as mono-isobutyl urea, monododecyl urea, monooctadecyl urea, stearoyl urea; further fatty acid imino ethers or arnidines. There also come into consideration compounds containing hydroxyl groups, such as, for instance, dodecylphenol, diisohexyl-phenol. Instead of the products named above there may also be used with advantage their products of reaction with aliphatic aldehydes, for example, their methylol compounds. If these latter are used the separate after-treatment with formaldehyde can be omitted in many 50 cases, a simple after-heating operation sufiicing. The process may be conducted, for example,
as follows: .the cellulose fibers are first saturated with a solution of the aliphatic compound in an organic solvent, for instance, pyridine, or acetone 55 or in an aqueous emulsion of the aliphatic compounds. They are then dried and exposed to the atcion of, for instance, formaldehyde, the concentration of which, when it is used in the form of a solution, must not be more than 5%. The formaldehyde may be added to the impregnating solution so that a subsequent treatment with formaldehyde becomes unnecessary; however, care must likewise be taken that the concentration of the aldehyde, for instance, of the formaldehyde, in the treating solution is not more than 5%. In this case the fiber needs only subsequent heating to ensure sufiicient reaction of the formaldehyde with the impregnating compound and the fiber.
In many cases it is useful to conduct the subsequent heating in an acid medium. For this purpose there may be added, for example, to the aqueous emulsion, acetic acid, lactic acid or agents of acid reaction such' as sodium bisulfite.
Fibers treated in this manner are characterized by a particularly high stability towards-water and even hot soap solution. For example, such material can be subjected to the usual fulling treatment, that is to say heating for A; hour in a. solution of 50 grams of soap and 5 grams of sodium carbonate per liter at 50 C. without loss of the property of repellent water. By suitable combination of the parent material and working conditions an effect can be obtained which is not notably diminished by several washings with boiling soap solution.
Another process of rendering cellulose fibers water-repellent consists in treating the fibers with solutions or dispersions of the aldehyde condensation products. As;a catalyst an acid substance is suitably added to the solutions or dispersions. The fibers may also be pretreated withan acid substance. The said aldehyde condensation products may also be added directly to the spinning solutions from which the artifical cellulose threads are prepared. The fibers which are prepared from solutions containing such an addition may, if required, be treated subsequently with an aldehyde.
The following examples serve to illustrate the invention, but they are not intended to limit it thereto; the parts are by weight:
1. Unsoaped dry viscose silk is immersed for 5 minutes in 5 times its weight of 'a pyridine solution containing 5-10 pen cent. of octadecylhepadecyl urea of the formula:
The silk is then drained, dried, immersed for 5 minutes in aqueous formaldehyde solution of 30 per cent. strength, centrifuged, dried and heated for 16 hours at C. Instead of this treatment with formaldehyde the fibrous material may be suspended for hour in a chamber charged with formaldehyde vapor at C. Instead of octadecyl-heptadecyl urea another of the substances specified above may be used.
2. Unsoaped dry viscose silk is immersed for 5 minutes in 10 times its weight of an aqueous emulsion containing 2 per cent. of stearin-amide, 0.2 per cent. of an emulsifying agent, obtainable by the reaction of ethylene-oxide with octadecenyl-alcohol, and0.3 per cent. of formaldehyde. The goods are centrifuged, dried and heated for 6 hours at 110 C. A subsequent washing is not necessary.
3. Unsoaped, dry viscose silk is immersed for 5 minutes in 5 times its weight of a solution of 5-10 per cent. strength of methylol-stearinamide in pyridine. The goods are centrifuged, dried and heated for 15 hours at 110 C.
4 The operation is conducted as described in Example 2 but 7 per cent. of lactic acid is added to the emulsion. By this addition of acid the stability of the water repelling preparation is strongly increased, particularly towards treatment with boiling dilute acid.
5. 10 parts of monostearylamino-cyanuric diamide are dissolved by warming 50 parts of a 10% lactic acid solution until the mass is homogeneous. The whole is made up with water to 2000 parts and while stirring, 40 parts of formaldehyde of 40 per cent. strength are added. A viscose artificial silk fabric is impregnated with this solution, squeezed, dried at moderate temperature and thereupon heated for 15 minutes at 155 C. to 160 C. The tissue thus treated is very water-repellent even after the usual washing with soap.
A similar good effect is also obtained by causing other amino derivatives of the 1.3.5-triazine, containing an alkyl radical with at least 4 carbon atoms, to act upon the cellulose fibers and "treating them, either simultaneously or subsequently, with aliphatic aldehydes. For example the 1.3.5-triazine of the formula:
obtainable from monochlorcyanuric diamide and l-amino-2-stearylamino-ethane, is a substance of good activity.
6. Dry viscose artificial silk is treated for 15 minutes with a solution of 5 grams of a condensation product, obtainable from stearic acid amide and aqueous formaldehyde, in 1 liter of carbon tetrachloride. The material is squeezed and dried in the air. Thereupon it is aftertreated at room temperature for 15 minutes with [I a solution of 5 grams of lactic acid in 1 liter of water, squeezed, dried in a current of air and heated for 2 hours at 110 C. The material is finally well rinsed and dried.
7. Viscose artificial silk tissue is treated for 10 minutes with an aqueous solution of the sodium salt of stearyl aminomethanesulfonic acid or stearylmethylaminomethanesulfonic acid, 5 grams of lactic acid being added per liter. The material is squeezed and dried at a temperature of 40 C. to 50 C. The tissue is then heated for 5-10 minutes at a temperature of C. to C.
8.'Undyed or dyed viscose artificial silk is treated with a solution which contains per liter of water 5 grams of lactic acid or glycolic acid, and is then dried. This pretreated material is treated for 10 minutes at 60 C. to 70 C. with a solution of a condensation product, obtainable from montanic acid amide and aqueous formaldehyde, in carbon tetrachloride. The material is squeezed, dried and heated for some minutes at a temperature of 140 C. There is thus obtained a hydrophobe tissue having a very good waterrepellent effect.
9. 4 parts of viscose artificial silk are impregnated with 100 parts by volume of a 1 per cent. solution of dodecylvinylether in dioxane, squeezed and dried. The silk is then loosened and heated for 2 hours at 110 C. under reduced pressure in an atmosphere of glacial acetic acid and formaldehyde. Thereupon it is washed while cold, hydro-extracted and dried. The viscose silk is very water-repellent and resistant to boiling.
10. Dyed viscose artificial silk fabric is 'immersed in a 2 per cent. solution of carbamic acidoctadecyl ester having the formula:
C1aH37.O.CO.NH2
in methylene chloride for about 10 minutes, then squeezed and after evaporation of the solvent the material is conducted through a bath which contains 5 per cent. of formaldehyde and 0.5 per cent. of la'cticv acid. The material is then dried in a tentering frame for about half-an-hour at 105 C. to 110C. Even after washing with soap the material is water-repellent and impermeable to water.
Instead of viscose artificial silk, cellulose fibers of all kinds, for instance, copper artificial silk, artificial spinning fibers, cotton, also mixtures of wool and cellulose fibers as well as fabrics made from the said fibers and mixtures of fibers may be used. In some cases a preliminary cleansing or desizing of the fibers or fabric is advisable.
' We claim:
1. The process of imparting hydrophobic properties to cellulose fibers by impregnating the fibers in a bath which contains compounds of the general formula:
' f, wherein R star ids for a radical selected from the group consisting of aliphatic and ,cycloali phatic radicals containing at least 4 carbon atoms, X stands for a member selected from the group consisting of O, NH, N.alkyl and R1 stands for a member of the group consisting of hydrogen and, aliphatic hydrocarbon radicals, at most 5 per cent. of aldehyde and an agent of acid action, and heating them after the impregnation.
3. The process of imparting hydrophobic properties to cellulose fibers by incorporating with them a compound of the general formula:
wherein R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals, containing at least '4 carbon atoms, x
stands for a radical selected from the group consisting of O, NH, N.alkyl and R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, treating the fibers with aliphatic aldehydes and subsequently heating them.
4. The process of imparting hydrophobic properties to cellulose fibers by impregnating the fibers with a condensation product from an aldehyde and a compound of the general formula:
wherein R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms,'X
wherein R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms, X stands for a radical selected from the group consisting of 0, NH, N.alky1 and R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, in the presence of an agent of acid action, and heating them after the impregnation.
- FRANZ EMIL HUBERT.
ERWIN HEISENBERG. ADOLF STEINDORFI". LUDWIG ORTHNER.
US81122A 1935-05-12 1936-05-21 Process of imparting hydrophobic properties to cellulose fibers Expired - Lifetime US2165265A (en)

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Application Number Priority Date Filing Date Title
DEI52329D DE762964C (en) 1935-05-12 1935-05-12 Process for making cellulose fibers water repellent
DE2111698X 1935-09-28
DE485593X 1935-11-23

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US102300A Expired - Lifetime US2111698A (en) 1935-05-12 1936-09-24 Process or preparing hydrophobic cellulose fibers
US166224A Expired - Lifetime US2211976A (en) 1935-05-12 1937-09-28 Process of imparting hydrophobic properties to cellulose fibers

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446864A (en) * 1944-06-26 1948-08-10 Quaker Chemical Products Corp Composition and process for imparting durable water repellent finish to textiles
US2507700A (en) * 1946-11-27 1950-05-16 Monsanto Chemicals N, n', n''-triacylmelamines
US2510522A (en) * 1944-12-09 1950-06-06 Montclair Res Corp Textile treating products and process of making
US2562161A (en) * 1948-02-06 1951-07-31 Cluett Peabody & Co Inc Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product
US2565194A (en) * 1947-03-27 1951-08-21 American Cyanamid Co Chlorotriazine resins and process of making the same
US2608494A (en) * 1948-08-28 1952-08-26 Walkden Makin & Co Ltd Treatment of textile fabrics for imparting antishrink properties thereto
US2641558A (en) * 1948-12-24 1953-06-09 Nat Lead Co Water repellence fixative treatment
US3128272A (en) * 1957-06-11 1964-04-07 Minnesota Mining & Mfg Perfluoroalkyl-substituted triazines
US3190763A (en) * 1960-12-17 1965-06-22 Hoechst Ag Process for the anti-static finishing of high molecular weight compounds
US4289665A (en) * 1977-12-23 1981-09-15 Cassella Aktiengesellschaft Process for the preparation of aqueous emulsions, stable in storage, of N.alkyl-N-alkylol-ureas and their application for the softening of leather

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE907163C (en) * 1938-06-07 1954-03-22 Hoechst Ag Process for making natural fibers of animal or vegetable origin or artificial fibers water-repellent
US2423185A (en) * 1939-07-08 1947-07-01 Hydronapthene Corp Process for the manufacture of coated and impregnated materials
DE766083C (en) * 1940-01-26 1954-02-01 Ig Farbenindustrie Ag Preparations for refining fiber materials
US2418696A (en) * 1942-03-09 1947-04-08 Courtaulds Ltd Modifying the dyeing properties of cellulose or cellulose derivative textile materials
US2451426A (en) * 1943-11-25 1948-10-12 Du Pont Bright zinc plating
NL60268C (en) * 1944-08-14 1947-11-15
US2431202A (en) * 1945-03-01 1947-11-18 Gen Aniline & Film Corp Self-dispersing methylolstear-amides
US2594384A (en) * 1946-11-12 1952-04-29 Monsanto Chemicals Fungi and bacteria resistant papermakers' felts and process for preparing same
US2540726A (en) * 1946-12-03 1951-02-06 Du Pont Treatment of a heat set, oriented nylon fabric with formaldehyde
NL71674C (en) * 1947-08-14
US2574114A (en) * 1948-04-26 1951-11-06 Bozel Maletra Prod Chimiques Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith
US2600698A (en) * 1948-11-13 1952-06-17 Monsanto Chemicals Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound
US2805196A (en) * 1952-02-11 1957-09-03 Tno Permselective electrodialysis
NL236360A (en) * 1958-02-20
US3232697A (en) * 1959-07-01 1966-02-01 Nalco Chemical Co Textile treatment
US3112155A (en) * 1962-02-02 1963-11-26 Sidney L Vail Glyoxal-amide reaction products
US4103051A (en) * 1975-11-03 1978-07-25 Milliken Research Corporation Pilling reduction in textiles
US4295930A (en) * 1980-03-17 1981-10-20 Nalco Chemical Company Alkoxylated dioxolanes as paper sizing agents
US4497715A (en) * 1982-08-03 1985-02-05 Colgate-Palmolive Company N-Alkylisostearamides as antistatic agents
US4563288A (en) * 1982-08-03 1986-01-07 Colgate-Palmolive Company N-Alkyl isostearamide antistatic agents, detergent compositions containing such agents, and processes for washing laundry in the presence of such agents, and with such compositions
US7713215B2 (en) * 2008-01-31 2010-05-11 Shriver Edgar L Steering, piercing, anchoring, distending extravascular guidewire

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AT118595B (en) * 1926-12-01 1930-07-25 Tootal Broadhurst Lee Co Ltd Process for impregnating textile yarns, fabrics and fabrics with synthetic resins.
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US2446864A (en) * 1944-06-26 1948-08-10 Quaker Chemical Products Corp Composition and process for imparting durable water repellent finish to textiles
US2510522A (en) * 1944-12-09 1950-06-06 Montclair Res Corp Textile treating products and process of making
US2507700A (en) * 1946-11-27 1950-05-16 Monsanto Chemicals N, n', n''-triacylmelamines
US2565194A (en) * 1947-03-27 1951-08-21 American Cyanamid Co Chlorotriazine resins and process of making the same
US2562161A (en) * 1948-02-06 1951-07-31 Cluett Peabody & Co Inc Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product
US2608494A (en) * 1948-08-28 1952-08-26 Walkden Makin & Co Ltd Treatment of textile fabrics for imparting antishrink properties thereto
US2641558A (en) * 1948-12-24 1953-06-09 Nat Lead Co Water repellence fixative treatment
US3128272A (en) * 1957-06-11 1964-04-07 Minnesota Mining & Mfg Perfluoroalkyl-substituted triazines
US3190763A (en) * 1960-12-17 1965-06-22 Hoechst Ag Process for the anti-static finishing of high molecular weight compounds
US4289665A (en) * 1977-12-23 1981-09-15 Cassella Aktiengesellschaft Process for the preparation of aqueous emulsions, stable in storage, of N.alkyl-N-alkylol-ureas and their application for the softening of leather

Also Published As

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GB463300A (en) 1937-03-22
BE418549A (en)
GB463472A (en) 1937-03-22
GB485593A (en) 1938-05-23
GB467166A (en) 1937-06-08
FR47692E (en) 1937-06-16
FR806170A (en) 1936-12-09
US2111698A (en) 1938-03-22
BE417657A (en)
DE762964C (en) 1953-11-30
BE415480A (en) 1936-06-30
NL50083C (en) 1941-04-15
FR813868A (en) 1937-06-10
NL44056C (en) 1938-09-15
US2211976A (en) 1940-08-20
NL45055C (en) 1939-02-15

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