US2211976A - Process of imparting hydrophobic properties to cellulose fibers - Google Patents

Process of imparting hydrophobic properties to cellulose fibers Download PDF

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US2211976A
US2211976A US166224A US16622437A US2211976A US 2211976 A US2211976 A US 2211976A US 166224 A US166224 A US 166224A US 16622437 A US16622437 A US 16622437A US 2211976 A US2211976 A US 2211976A
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acid
cellulose fibers
fibers
solution
grams
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US166224A
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Hubert Franz Emil
Heisenberg Erwin
Steindorff Adolf
Orthner Ludwig
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GAF Chemicals Corp
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General Aniline and Film Corp
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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

  • Patenteci Aug. 20, 1940 PROCESS OF IMPARTING HYDROPHOBI PROPERTIES T0 CELLULOSE FIBERS Franz Emil Hubert, Dessau, Erwin Heisenberg, Leip g", and Adolf Steindorlf and Ludwig- Orthner, Frankfort-on-the-Main, Germany, assignors, by mesne assignments, to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application September 28, 1937,
  • the present invention relates to a process of imparting hydrophobic properties to cellulose fibers.
  • fibers of cellulose or hydrated cellulose such as cotton, artlficialsilk 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 01' 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 compounds are, for example, fatty amines and fatty acid amides such as dodecyl- "amine, hexadecylamine octadecylamine, octadecenylamine, the amides of carboxylic acids, for example, abietic acid amide, lauric acid amide, stearic acid methylamide, stearic acid butylamide, stearic acid octadecylamide, stearic acid amide, montanic acid amide, paraffin carboxylic acid amide, dichlorostearic acid amide, phenyl-' stearic acid amide, furthermore alkylbenzoic acid amides and the nuclear hydrogenation products thereof, for instance, p-dodecylbenzoic acid amide and dodecylcyclohexylcarboxylic acid yIphenox-ypropionic acid amide; further compounds of the character of alkyl-sub
  • the cellulose fibers are first saturated with a solution of the aliphatic compound in an organic solvent, for instance, pyridine, acetone or in an aqueous emulsion ofthe aliphatic compounds. They are then dried and exposed to'the action of, for instance, formaldehyde.
  • the formaldehyde may be added to the impregnatingsolu ,tion so that a subsequent treatment with formaldehyde becomes unnecessary. 'In this case the fiber needs only subsequent heating to ensure sufilcient reaction of the formaldehyde with the impregnating compound and the fiber.
  • the ,hydrophobe effect is essentially enhanced if the impregnation is carried out in the presence of an agent having a feebly acid action, for example, acetic acid, lactic acid or agents of acid reaction such as sodium bisulfite.
  • the impregnation may be carried out in an aqueous medium as well as in an organic solvent, such as benzine, carbontetrachloride, pyridine and the like.
  • An agent having a feebly acid action may be added during the impregnation, or it may be incorporated with the fiber by a preor' after-treatment.
  • 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 hour in a solution of 50 grams of soap and grams of sodium carbonate per liter at 50 C. without loss of the property of repelling water.
  • the parent material and working conditions 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.
  • An alternative method of incorporating the material in the fibers consists in adding the compound in question as such or its condensation product with aldehyde to the spinning solution which is to serve as the parent material for making artificial cellulose threads.
  • the fibers produced from solutions containing such an addition may, if desired, be subsequently treated with an aliphatic aldehyde.
  • Non-dyed or dyed viscose artificial silk is treated with a solution-which contains per liter
  • a cotton fabric is treated for a short time with an aqueous lactic acid solution of 1 per cent. strength and then dried at 50 C. to 60 C. It is subsequently impregnated for 10 minutes with a solution of 1 per cent. strength of 9.10-dichlorostearic acid methylolamide in cyclohexane, centrifuged and heated at 135 C. to 140 C. for minutes.
  • Dyed artificial silk is impregnated with an alcoholic solution containing'per liter 5 grams of.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Artificial Filaments (AREA)

Description

Patenteci Aug. 20, 1940 PROCESS OF IMPARTING HYDROPHOBI PROPERTIES T0 CELLULOSE FIBERS Franz Emil Hubert, Dessau, Erwin Heisenberg, Leip g", and Adolf Steindorlf and Ludwig- Orthner, Frankfort-on-the-Main, Germany, assignors, by mesne assignments, to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application September 28, 1937,
' Serial NO- 166324. In Germany May 11, 1935 8 Claims.
The present invention relates to a process of imparting hydrophobic properties to cellulose fibers.
This application is a continuation-in-part of "our co-pending U. S. patentapplication Serial No. 81,122, filed May 21, 1936.
It is known that fibers of cellulose or hydrated cellulose, such as cotton, artlficialsilk 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 01' 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 compounds are, for example, fatty amines and fatty acid amides such as dodecyl- "amine, hexadecylamine octadecylamine, octadecenylamine, the amides of carboxylic acids, for example, abietic acid amide, lauric acid amide, stearic acid methylamide, stearic acid butylamide, stearic acid octadecylamide, stearic acid amide, montanic acid amide, paraffin carboxylic acid amide, dichlorostearic acid amide, phenyl-' stearic acid amide, furthermore alkylbenzoic acid amides and the nuclear hydrogenation products thereof, for instance, p-dodecylbenzoic acid amide and dodecylcyclohexylcarboxylic acid yIphenox-ypropionic acid amide; further compounds of the character of alkyl-substituted ureas such as mono-isobutyl 'urea, monododecyl urea, mono-octadecyl urea, stearoyl urea; further fatty acid imlno ethers or amidines.
There also come into consideration compoundsv containing hydroxyl groups, such as, for instance,
dodecylphenol, di-isohexyl-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 cases, a simple after-heating operation suflicing.
The reaction products of carboxylic acid amides with formaldehyde, for instance, have the general formula:
member of the group consisting of hydrogen and aliphatic hydrocarbon radicals.
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, acetone or in an aqueous emulsion ofthe aliphatic compounds. They are then dried and exposed to'the action of, for instance, formaldehyde. The formaldehyde may be added to the impregnatingsolu ,tion so that a subsequent treatment with formaldehyde becomes unnecessary. 'In this case the fiber needs only subsequent heating to ensure sufilcient reaction of the formaldehyde with the impregnating compound and the fiber.
In many cases the ,hydrophobe effect is essentially enhanced if the impregnation is carried out in the presence of an agent having a feebly acid action, for example, acetic acid, lactic acid or agents of acid reaction such as sodium bisulfite. The impregnation may be carried out in an aqueous medium as well as in an organic solvent, such as benzine, carbontetrachloride, pyridine and the like. An agent having a feebly acid action may be added during the impregnation, or it may be incorporated with the fiber by a preor' after-treatment.
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 hour in a solution of 50 grams of soap and grams of sodium carbonate per liter at 50 C. without loss of the property of repelling 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.
An alternative method of incorporating the material in the fibers consists in adding the compound in question as such or its condensation product with aldehyde to the spinning solution which is to serve as the parent material for making artificial cellulose threads. The fibers produced from solutions containing such an addition may, if desired, be subsequently treated with an aliphatic aldehyde.
The following examples serve to illustrate the invention, but they-are not intended to limit it thereto, the parts being by weight:
(1) Unsoaped, dry viscose silk is immersed for 5 minutes in 5 times its weight of a solution of 5 to per cent. strength of methylol-stearinamide in pyridine. The goods are centrifuged. dried and heated for hours at 110 C.
(2) 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 one liter of carbon tetrachloride. The material is squeezed and dried at the air. Tbereupon it is after-treated at room temperature for 15 minutes with 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.
(3) Non-dyed or dyed viscose artificial silk is treated with a solution-which contains per liter,
of water 5 grams of lactic acid or glycolic acid;
" erties to cellulose-fibers by impregnating the fibers in a bath which contains an N-methylol and is then dried. This pre-treated 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. Thereisfthus obtained a hydrophobe tissue having .a,very good water-repellant effect. l
(4) A cotton fabric is treated for a short time with an aqueous lactic acid solution of 1 per cent. strength and then dried at 50 C. to 60 C. It is subsequently impregnated for 10 minutes with a solution of 1 per cent. strength of 9.10-dichlorostearic acid methylolamide in cyclohexane, centrifuged and heated at 135 C. to 140 C. for minutes. I
(5) Artificial silk crepe is impregnated with an alcoholic solution of 2 per cent. strength of dodecylbenzoic acid methylolamide. It is then siueezed, dried at C. and heated for 1 hour at 1 0 C.
(6) Artificial silk crepe is treated for some minutes in an aqueous emulsion of p-dodecylphenylbutyric acid methylolamide, containing per liter 10 grams of the methylolamide and 5 grams of lactic acid. It is subsequently squeezed, dried at 50 C. to C. and heated for 30 minutes at 130 C. to 140 C.
(7) Cotton calico isimpregnated for a short time with a solution of 2 per cent. strength of the condensation product of dodecylcycloli'exylbutyric acid amide and formaldehyde in carbon tetrachloride. Then it is squeezed and heated for 1 hour at 140 C.
(8) Dyed artificial silk is impregnated with an alcoholic solution containing'per liter 5 grams of.
m'aleic acid and 20 grams of isooctylphenoxyacetic acid methylol amide. After centrifuging the whole is heated for 1 hour at C. to C.
(9) 15 grams of beta-naphthoxyacetic acidmethylolamide are dissolved in 1000 grams of alcohol and 10 grams of lactic acid are added to this solution. Artificial silk fabric is treated in the bath so preparedfor ,5 hour at 60 C. to 70 C. Then it is squeezed, dried at about 50 C. and subsequently exposed to a temperature of C. for 60 minutes in a drying cylinder or in a tentering frame or in a drying oven. The fabric has become hydrophobe. The effect is enhanced by washing the fabric in a soap solution rendered alkaline by means of sodium carbonate and subsequent drying.
,With a still better success there may be used a bath prepared in an analogous manner and containing 10-15 grams of iso-octyl-beta-naphthoxyacetic acid-methylolamide.
advisable.
We claim:
1. The process of imparting hydrophobic properties to cellulose fibers by incorporating with them an N-methylol compound of 'an acid amide of a monocarboxylic acid and ammonia which contains at least one radical with at least 4 carbon atoms selected from the group consisting of aliphatic and cycloaliphatic radicals and subsequently heating them.
2. The process of imparting hydrophobic propcompound of an acid amide of a monocarboxylic acid and ammonia having at least one radical with at least 4 carbon atoms selected from the group consisting of aliphatic and cycioaliphatic radicals and heating them after the impregnation.
, 3. The process of imparting hydrophobic properties to cellulose fibers by impregnating the fibers in a bath. which contains an N-methylol compound of an acid amideof a monocarboxylic acid and ammonia having at least one radical with at least 4 carbon atoms selected from the group consisting of aliphatic and cycloaliphatic radicals, and an agent of acid action such as a feeble acid, and heating them after the impregnation.
4. The process of imparting hydrophobic prop- .erties to cellulose fibers by impregnating the :the group consisting of aliphatic and cycloaliphat-ic radicals, in the presence of an age t of acid action such as a feeble acid and heating them after the impregnation.
6. The process of imparting hydrophobic propleast 4 carbon atoms, in the presence of a. feeble erties to cellulose fibers by impregnating the fibers acid and heating them after the impregnation. with a. compound of the general formula: "I. Waterproof cellulose fibers obtained by the process defined in claim 1. 8. Waterproof cellulose fibers obtained by the 5 process defined in claim 6. FRANZ EMIL HUBERT.
cmon ERWIN HEISENBERG.
ADOLF STEINDORFE. 1 wherein R stands for an aliphatic radical with at LUDWIG'ORTHNER. 10
US166224A 1935-05-12 1937-09-28 Process of imparting hydrophobic properties to cellulose fibers Expired - Lifetime US2211976A (en)

Applications Claiming Priority (3)

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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US81122A Expired - Lifetime US2165265A (en) 1935-05-12 1936-05-21 Process of imparting hydrophobic properties to cellulose fibers
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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US81122A Expired - Lifetime US2165265A (en) 1935-05-12 1936-05-21 Process of imparting hydrophobic properties to cellulose fibers
US102300A Expired - Lifetime US2111698A (en) 1935-05-12 1936-09-24 Process or preparing hydrophobic cellulose fibers

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US (3) US2165265A (en)
BE (3) BE415480A (en)
DE (1) DE762964C (en)
FR (3) FR806170A (en)
GB (4) GB463472A (en)
NL (3) NL45055C (en)

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US2431202A (en) * 1945-03-01 1947-11-18 Gen Aniline & Film Corp Self-dispersing methylolstear-amides
US2562161A (en) * 1948-02-06 1951-07-31 Cluett Peabody & Co Inc Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product
US2805196A (en) * 1952-02-11 1957-09-03 Tno Permselective electrodialysis
US3112155A (en) * 1962-02-02 1963-11-26 Sidney L Vail Glyoxal-amide reaction products
US3232697A (en) * 1959-07-01 1966-02-01 Nalco Chemical Co Textile treatment
US4103051A (en) * 1975-11-03 1978-07-25 Milliken Research Corporation Pilling reduction in textiles
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
US4295930A (en) * 1980-03-17 1981-10-20 Nalco Chemical Company Alkoxylated dioxolanes as paper sizing agents
US20090198153A1 (en) * 2008-01-31 2009-08-06 Shriver Edgar L Steering, piercing, anchoring, distending extravascular guidewire

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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
US2446864A (en) * 1944-06-26 1948-08-10 Quaker Chemical Products Corp Composition and process for imparting durable water repellent finish to textiles
NL60268C (en) * 1944-08-14 1947-11-15
US2510522A (en) * 1944-12-09 1950-06-06 Montclair Res Corp Textile treating products and process of making
US2594384A (en) * 1946-11-12 1952-04-29 Monsanto Chemicals Fungi and bacteria resistant papermakers' felts and process for preparing same
US2507700A (en) * 1946-11-27 1950-05-16 Monsanto Chemicals N, n', n''-triacylmelamines
US2540726A (en) * 1946-12-03 1951-02-06 Du Pont Treatment of a heat set, oriented nylon fabric with formaldehyde
US2565194A (en) * 1947-03-27 1951-08-21 American Cyanamid Co Chlorotriazine resins and process of making the same
BE480227A (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
US2608494A (en) * 1948-08-28 1952-08-26 Walkden Makin & Co Ltd Treatment of textile fabrics for imparting antishrink properties thereto
US2600698A (en) * 1948-11-13 1952-06-17 Monsanto Chemicals Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound
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
NL114029C (en) * 1958-02-20
NL272600A (en) * 1960-12-17
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

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DE197965C (en) * 1906-04-24
AT118595B (en) * 1926-12-01 1930-07-25 Tootal Broadhurst Lee Co Ltd Process for impregnating textile yarns, fabrics and fabrics with synthetic resins.
DE542186C (en) * 1929-06-14 1932-01-21 Alexander Nathansohn Dr Process for waterproofing raw, chemically uncleaned textile fibers
FR751641A (en) * 1932-02-29 1933-09-07 Ig Farbenindustrie Ag Process for the preparation of auxiliary condensation products
AT136377B (en) * 1933-01-13 1934-01-25 Heberlein & Co Ag Finishing process for vegetable textiles.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2431202A (en) * 1945-03-01 1947-11-18 Gen Aniline & Film Corp Self-dispersing methylolstear-amides
US2562161A (en) * 1948-02-06 1951-07-31 Cluett Peabody & Co Inc Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product
US2805196A (en) * 1952-02-11 1957-09-03 Tno Permselective electrodialysis
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
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
US4295930A (en) * 1980-03-17 1981-10-20 Nalco Chemical Company Alkoxylated dioxolanes as paper sizing agents
US20090198153A1 (en) * 2008-01-31 2009-08-06 Shriver Edgar L Steering, piercing, anchoring, distending extravascular guidewire
US7713215B2 (en) 2008-01-31 2010-05-11 Shriver Edgar L Steering, piercing, anchoring, distending extravascular guidewire

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US2111698A (en) 1938-03-22
FR806170A (en) 1936-12-09
GB463300A (en) 1937-03-22
NL44056C (en) 1938-09-15
BE418549A (en)
GB467166A (en) 1937-06-08
BE415480A (en) 1936-06-30
BE417657A (en)
FR813868A (en) 1937-06-10
NL45055C (en) 1939-02-15
FR47692E (en) 1937-06-16
GB485593A (en) 1938-05-23
US2165265A (en) 1939-07-11
NL50083C (en) 1941-04-15
DE762964C (en) 1953-11-30
GB463472A (en) 1937-03-22

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