US2795517A - Modification of the properties of fibrous materials - Google Patents

Modification of the properties of fibrous materials Download PDF

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US2795517A
US2795517A US47220854A US2795517A US 2795517 A US2795517 A US 2795517A US 47220854 A US47220854 A US 47220854A US 2795517 A US2795517 A US 2795517A
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Prior art keywords
fabric
parts
solution
water
hydrazide
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English (en)
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Lowe Arthur
Williams Gerald
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Priority claimed from GB3346553A external-priority patent/GB760598A/en
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    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds
    • D21H17/08—Isocyanates
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
    • 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
    • D06M13/10—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 oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • 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
    • D06M13/422—Hydrazides
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H11/00—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only
    • D21H11/16—Pulp or paper, comprising cellulose or lignocellulose fibres of natural origin only modified by a particular after-treatment
    • D21H11/20—Chemically or biochemically modified fibres
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60K—ARRANGEMENT OR MOUNTING OF PROPULSION UNITS OR OF TRANSMISSIONS IN VEHICLES; ARRANGEMENT OR MOUNTING OF PLURAL DIVERSE PRIME-MOVERS IN VEHICLES; AUXILIARY DRIVES FOR VEHICLES; INSTRUMENTATION OR DASHBOARDS FOR VEHICLES; ARRANGEMENTS IN CONNECTION WITH COOLING, AIR INTAKE, GAS EXHAUST OR FUEL SUPPLY OF PROPULSION UNITS IN VEHICLES
    • B60K2704/00—Control devices, wherein the control is combined with or mainly influenced by the working of the engine or the main coupling, e.g. control device is linked to the carburettor control and is influenced by depression of pedal, for semi-automatic or non-automatic transmission having toothed wheels
    • B60K2704/02—Control devices, wherein the control is combined with or mainly influenced by the working of the engine or the main coupling, e.g. control device is linked to the carburettor control and is influenced by depression of pedal, for semi-automatic or non-automatic transmission having toothed wheels without preselection system, the control being mechanical
    • 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
    • Y10S8/11—Isocyanate and carbonate modification of fibers
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2033—Coating or impregnation formed in situ [e.g., by interfacial condensation, coagulation, precipitation, etc.]

Definitions

  • This invention relates to the modification of the properties of fibrous materials and more particularly to the treatment of textiles, leather, paper, etc. with organic hydrazides and nitrous acid, and, preferably, formaldehyde.
  • Any organic hydrazide containing one or more hydrazide groups in the molecule, can be used in the process of this invention.
  • dihydrazides of succinic, glutaric, adipic and sebacic acids, hexadecane-l:l6-dicarboxylic dihydrazide, benzoic acid hydrazide, isophthalic acid dihydrazide or citric acid trihydrazide.
  • the treatment of the fibrous material with the'hydrazide and nitrous acid may be accomplished for example by padding through an aqueous-solution or dispersion of an acid salt of the hydrazide, drying and then padding through an aqueous solution of an alkali salt of nitrous acid.
  • the hydrazide salt impregnated material may be sprayed with a solution of a nitrite.
  • hydrazide and nitrite may be accomplished simultaneously by padding through a solution or dispersion containing both the hydrazide and the nitrite.
  • the impregnated material is then dried and treat- :ed with an acid in order to liberate the nitrous acid.
  • Suitable concentrations of hydrazide or salt thereof and nitrite in the treatment baths are from about 0.5% to about 20% so that with a take-up of about 100%, the proportion of hydrazide and nitrite deposited on the fibre is from about 0.5 to about 20%.
  • the temperature of the treatment baths may vary between C. and 100 C. It is sometimes convenient to treat the material with the hydrazide salt solution atelevated temperatures such as 50100 C. and then with the alkali nitrite at lower temperaturessuch as 0 to 20. C.
  • the modification of the properties of thefibrous material is'achieved by drying the material after treatment with hydrazide and nitrous acid. Afterdrying, the treated material is preferably baked at a temperature of from about 50 C. to about 200 C. The time required for the baking step, after drying the material, is usually from about 3 minutes to about half an hour. In some cases, satisfactory results are obtained by conditioning the treated material at room temperature for some hours, with out any. baking stage.
  • viscose rayon fabrics thathave been treated according to the process of this inventionhave enhanced dimensional stability.
  • Treated paper is found to possess a greatly increased wet strength.
  • -A'substantial degree of water-repellency may also be imparted to cellulosic materials.
  • Softening agents or substances to give a firm handle may be incorporated with the hydrazide in order-to give enhanced effects.
  • the modification of the properties of the fibrous materials is still further increased by inclusion in the treatment baths of formaldehyde.
  • the formaldehyde may be added to any of the treatment baths, containing, for example, the hydrazide salt or the nitrite or the mixture of hydrazide and nitrite.
  • concentration of formaldehyde in the treatment baths is conveniently from about 1% to 15% by weight, so that with a take-up of about the amount of formaldehyde deposited on the fibre is from about -1% to about 15 by weight of the fibre.. 1
  • the .treatment process of this invention may be combined with other treatments of the fibrous material and these other treatments are thereby modified, improved, enhanced in effect or rendered more permanent;-
  • Such other treatments are for example mechani cal finishes applied to cotton fabrics such as calendering, embossing, beetling, rippling, pressing or schreinering.
  • the effects so obtained vary according to theprocess; thus'for example there may be produced lustre, glaze and finishes known as moire or cite.
  • an amide, an amidine or an aminotriazine may be applied to the material during the treatment with the hydrazide so as to be present within the material during the subsequent baking treatment.
  • Particularly suitable amides (which include thioamides, carboxylic acid amides and sulphonarnides) are urea, dithiourea and acetamide, benzene sulphonarnide or p-toluene sulphonamide; suitable amidines include cyanamide, guanidine and aminoguanidine; andsuitable aminotriazines include melamine.
  • the improvement which is brought about by these amides, amidines or aminotriazines is demonstrated by the firmer handle of the finished material and the greater resistance of the mechanical eifect to washing.
  • Example 1 'A cotton fabric is immersed ina solution of parts of sebacic-acid dihydrazide dihydrochloride in 95 parts of water'a't 60 C.'and squeezed between rollers so that the uptake of the solution is 75% of thedry weight of the fabric.
  • the fabric is then dried at 50 'C. and then immersed ina solution'of 5 parts of sodium'nitrite in 95.
  • Example 2 A cotton fabric is immersed in a dispersion containing Sparts of sebacic acid dihydrazide, 3 parts of sodium nitrite, 0.3 part of the disodium salt of methylene dinaphthylene sulphuric acid and 91.7 parts of water and squeezed between rollers so that the uptake of the solution is 75% of the dry weight of the fabric.
  • the fabric is dried at 50 C. and then immersed in a solution of 5 parts of acetic acid in 95 parts of water and squeezed between rollers so that the uptake of the solution is 75% of the dry weight.
  • the fabric isthen dried at 2030 4 C.
  • the resulting glaze is resistant to boiling soap solutions.
  • Example 3 A viscose staple fibre plain weave fabric is immersed in a solution containing 3 parts of adipic dihydrazide dihydrochloride and 97 .parts of water and squeezed between rollers so that the uptake of the solution is 80% of the dry weight of the fabric. The fabric is then stretched back to its former dimensions on a pin stenter and sprayed in this state with a solution of 10 parts of sodium nitrite in 90 parts of water so that the whole material is thoroughly wetted out and has increased in weight by 100%. The treated material is then dried and baked by heating in an oven at 125. C. vfor 10 minutes. a
  • the material is then dried and baked by heating in an oven at C. for 5 minutes.
  • Theresulting paper has a wet strength many times greater than the untreated material.
  • Example 6 A viscose staple fibre plain weave fabric is immersed in a. solution containing 2.5 parts of sebacic acid dihydro- :chloride, 2.5 parts ofacetamide and 95 parts of water at 50 C.. and squeezed between rollers so that theuptake of solution is 75% of the-dry weight of thefabric.
  • the fabric is stretched back to its original dimensions on a pin stenter and dried in an oven at a temperature of 125 C. for 5 minutes.
  • the dry fabric is then immersed in an aqueous solution containing 1.6% formaldehyde and 3.0% sodium nitrite and squeezed between rollers so that the uptake of the solution is 75% of the dry weight of the fabric.
  • the fabric is stretched to its original dimensions on a pin. stenter and then placed in an oven maintained at a temperature of 125 C. for 15 minutes.
  • Example 8 A mercerised cotton gaberdine fabric is padded through a solution containing 2.5 parts of sebacic dihydradize dihydrochloride, 3 parts of stearic hydrazide hydrochloride and 94.5 parts of water at 80 C. and squeezed between rollers so that the uptake of the solution is 60% of the dry weight of the fabric. The fabric is then air-dried and padded through a solution containing 1 part of formaldehyde, 3 par-ts of sodium nitrite and 96 parts of water at 20 C., squeezed between rollers so that the uptake of the solution is 60% of the dry weight of the fabric and finally placed in an oven maintained at a temperature of 130 C. for 10 minutes.
  • the fabric is then rinsed in warm water for 5 minutes and dried.
  • the fabric thus obtained has a high degree of water-repellency which is only slightly affected by washing in aqueous solution of 0.1% soap and 0.1% soda ash at the boil for 1 hour, or by dry cleaning in white spirit for /2 hour.
  • Example 9 A mercerised cotton gaberdine fabric is padded through a solution containing 2.5 parts of sebacicv dihydrazide hydrochloride, 3 parts of stearic hydrazide hydrochloride and 94.5 parts of water at 80 C. and squeezed between rollers so that the uptake of the solution is 65% of the dry weight of the fabric. The fabric is then air dried and padded through a solution containing 3 parts-of sodium nitrite and 97 parts of water at 20 C., squeezed between rollers so that the uptake of the solution is 60% of the dry weight of the fabric and finally placed in an'oven maintained at a temperature of 130 C. for minutes. The fabric is then rinsed in warm water for 5 minutes and dried. The fabric thus obtained has a high degree of water-repellency which is only slightly affected by washing in aqueous 0.1% soap solution at 70 C. for 1 hour.
  • Example 10 A mercerised cotton gaberdine fabric is padded through a solution containing 2.5 parts of sebacic dihydrazide dihydrochloride, 3 parts of ll-hydroxystearic hydrazide hydrochloride and 94.5 parts of water at 80 C. and squeezed between rollers so that the uptake of the solution is 60% of the dry weight of the fabric.
  • the fabric is then air-dried and padded through a solution containing 1 part of formaldehyde, 3 parts of sodium nitrite and 96 parts of water at C. squeezed between rollers so that the uptake of 6 the solution is 60% of'the dry weight of the fabric and finally "placed'in anoven' maintained'at"atemperature of 130 C. for 10 minutes.
  • the fabric is then rinsedin Warm water for 5 minutes and. dried.
  • the fabric thus obtained has a high degreeof water repellency, which is only slightly affected by washing in an aqueous solution of 0.1% soap and 0.1% sodaash at the boil for 1 hour,
  • a mercerised cotton gaberdine fabric is padded through a solution containing 255 parts of sebacic dihydrazide dihydrochloride, 3 parts of stearic hydrazide hydrochloride and-94.5 parts of waterat"- and squeezed between rollers so that the uptake ofthesolution is 60% of the dry weight of the fabric.
  • The;fabric is then padded through a solution containing 3 parts of formaldehyde, 9 parts of sodium nitrite and- 88 parts of water and squeezed between rollers so that the increase in weight of the fabric is now 100% of the dry weight.
  • the wet fabric is then rinsed thoroughly.
  • Example 12 I A viscose staple fibre plain 'weave fabric is immersed in a solution containing 2.5 parts 'of isophthalic dihydrazide dihydrochloride and 97.5 parts of water and squeezed between rollers so that the uptake of the solution is 80% of the dry weight of the fabric.
  • the fabric is then stretched back to its former dimensions on a pin stenterand sprayed in this state with a solution of 10 parts of sodium nitrite in 90 parts of water so that the whole material is thoroughly wetted out and has increased in weight by
  • the treated material is then dried and baked by heating in an oven at C. for 10 minutes.
  • the fabric thus obtained shows good resistance to shrinkage by alkaline washing treatments.
  • Example 13 A viscose staple fibre plain weave fabric isimmersed in a solution containing 4 parts of the hydrochloride of polyacrylic polyhydrazide (obtained by heating ethyl polyacrylate with hydrazide hydrate) and 96 parts of water and squeezed between rollers so that the uptake of the solution is 75 of the dry weight of the fabric.
  • the fabric is then dried at 20-50 C. and then immersed in a solution of 3 parts of sodium nitrite and 1% of formaldehyde in 96 parts of water and squeezed between rollers so that the Y uptake of the solution is 75% of the dry weight.
  • the wet fabric is then stretched to its former dimensions on a pin stenter and then dried and baked by heating in an oven at C. for 10 minutes.
  • the resulting fabric has a firm full handle and shows good dimensional stability when subjected to alkaline washing treatments.
  • a plain weave cotton fabric is immersed in a solutionof 4.5 parts of sebacic dihydrazide dihydrochloride 'in' 95.5 parts of water, squeezed between rollers so that the uptake of the rollers is 7 5% of the dry weight of the fabric.
  • the wet fabric is then immersed in a solution of 4 parts of sodium nitrite in 96 parts of water, squeezed through rollers so that the weight of the fabric is now twice as great as its dry weight.
  • the fabric is then conditioned to contain 10% of its weight of moisture, and embossed according to conventional means.
  • the fabric is then given a heat treatment of 3 minutes at 140 C.
  • the embossed design produced is highly resistant to washing in boiling soap solutions.
  • the heat treatment after embossing may be omitted and the-fabric conditioned at roomtemperature for 24 hfours.-
  • The. resulting embossed design is resistant to washing inboiling soap solutions.
  • Example 15 A cellulose acetate plain weave fabric is passed through a solution of 4 parts of sebacic dihydrazide dihydrochloride in 96 parts of water at 60 C., squeezed through rollers so that the uptake of the solution is 50% of the dry weight
  • Example 16 A mercerised cotton gaberdine fabric is passed through a solution of" 3 parts of stearic hydrazidehydrochloride and 97 parts of water at 70 C. and squeezed between roller'sso-that'the uptake of the solution is 60% of the dry weight of the fabric.
  • the fabric is then passed through a solution of 2 parts sodium nitrite in 98 parts of water, squeezed between rollers so that the weight of the wet fabric is now twice that of the dry fabric and finally dried and baked in an oven at 140 C. for 10 minutes.
  • the fabric is then rinsed in warm water for minutes and dried.
  • the fabric thus obtained has a high degree of water repellency.
  • Example 17 25 parts of bleached sulphite pulp are suspended in 1500 parts of water and disintegrated by vigorous stirring. 12.5 parts of a aqueous solution of aluminium sulphate are added followed by 0.6 part of sebacic dihydrazide dihydrochloride. After standing at 20 C. for 30 minutes, 3 parts of sodium nitrite are added and the suspension is stirred for a further 5 minutes. 3500 parts of water are then added and after stirring for a further 5 minutes, the mixture is filtered and the resulting paper dried and baked at 115 C. for 10 minutes. Paper prepared by this method has a markedly higher bursting strength than that prepared when the hydrazide is omitted.
  • Example 18 A plain weave cloth made up from polyethylene terephthalate yarn is padded through a solution containing 2.5 parts of sebacic-dihydrazide hydrochloride, 3 parts of stearic hydrazide hydrochloride and 94.5 parts of water at 80 C. and squeezed between rollers, the uptake of the solution being 35% of the dry weight of the fabric. The cloth is then dried at 50-60 C. and padded through a solution containing 3 parts of sodium nitrite and 97 parts ofwater at 20 C., squeezed between rollers and placed in an oven maintained at a temperature of 120 C. for minutes. The fabric is then rinsed in warm water and dried. The cloth thus obtained has a high degree of water repellency which is only slightly affected by washing in aqueous 0.1% soap solution at 70 C. for 1 hour.
  • Example I 9 sebacic dihydrazide' dihydrochloride, 3 parts of ll-li'y droxystearic'hydrazide hydrochloride and 94.5 parts of water at C. and squeezed between rollers so that the uptake of the solution is 45% of the dry weight of the fabric.
  • the cloth is then air dried and padded through a solution containing 1 part of formaldehyde, 3 parts'of sodium nitrite and 96 parts of water at 20 C., squeezed between rollers so that the uptake of the solution is 45% of thedry Weight of the fabric and finally placed in an oven maintained at a temperature of C. for 10 minutes.
  • the fabric is then rinsed in warm water for 5 minutcs'and dried.
  • the fabric thus obtained has a high degree of water repellency.
  • Example 20 Pelts are immersed in 215% aqueous solution of adipic dihydrazide for 12 hours at a temperature of 1520 C. The pelts are then freed from supernatant liquor by decantation and immersed in a 3% aqueous solutionof nitrous acid containing l;6% formaldehyde for 12 hours at a temperature of 15 C. After thorough rinsing with water and drying at 20 C. a tanned leather having a shrink temperature of 87 C. is obtained.
  • a process for the modification of the properties of fibrous materials involving in situ formation of an organic isocyanate in said fibrous material which comprises impregnating said material with an organic hydrazide in a substantially aqueous medium and thereafter forming nitrous acid in said hydrazide impregnated material to produce said isocyanate.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US47220854 1953-12-02 1954-11-30 Modification of the properties of fibrous materials Expired - Lifetime US2795517A (en)

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Application Number Priority Date Filing Date Title
GB3346553A GB760598A (en) 1953-12-02 1953-12-02 Modification of the properties of fibrous materials
GB2795517X 1954-11-24

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US2795517A true US2795517A (en) 1957-06-11

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US (1) US2795517A (xx)
BE (1) BE533827A (xx)
FR (1) FR1116501A (xx)
NL (1) NL88699C (xx)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432456A (en) * 1960-08-12 1969-03-11 Bayer Ag Polyurethanes prepared from dihydrazides
US5635239A (en) * 1989-12-08 1997-06-03 Kimberly-Clark Worldwide, Inc. Absorbent structure possessing improved integrity

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1875452A (en) * 1932-09-06 Max habtmann
US2173029A (en) * 1936-02-19 1939-09-12 Heberlein Patent Corp Process for rendering textiles water-repellent and products therefrom
US2334476A (en) * 1940-09-04 1943-11-16 Du Pont Unsaturated isocyanate
US2544709A (en) * 1947-04-14 1951-03-13 Armstrong Cork Co Method of preparing low molecular weight isocyanates
US2680131A (en) * 1952-07-29 1954-06-01 Aerojet General Co Trans vinylene diisocyanate and method of preparation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1875452A (en) * 1932-09-06 Max habtmann
US2173029A (en) * 1936-02-19 1939-09-12 Heberlein Patent Corp Process for rendering textiles water-repellent and products therefrom
US2334476A (en) * 1940-09-04 1943-11-16 Du Pont Unsaturated isocyanate
US2544709A (en) * 1947-04-14 1951-03-13 Armstrong Cork Co Method of preparing low molecular weight isocyanates
US2680131A (en) * 1952-07-29 1954-06-01 Aerojet General Co Trans vinylene diisocyanate and method of preparation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3432456A (en) * 1960-08-12 1969-03-11 Bayer Ag Polyurethanes prepared from dihydrazides
US5635239A (en) * 1989-12-08 1997-06-03 Kimberly-Clark Worldwide, Inc. Absorbent structure possessing improved integrity

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Publication number Publication date
BE533827A (xx) 1900-01-01
FR1116501A (fr) 1956-05-08
NL88699C (xx) 1900-01-01

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