US2161808A - Treatment of textile materials - Google Patents

Treatment of textile materials Download PDF

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Publication number
US2161808A
US2161808A US93230A US9323036A US2161808A US 2161808 A US2161808 A US 2161808A US 93230 A US93230 A US 93230A US 9323036 A US9323036 A US 9323036A US 2161808 A US2161808 A US 2161808A
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United States
Prior art keywords
materials
hydrazine
formaldehyde
textile materials
textile
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Expired - Lifetime
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US93230A
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Finlayson Donald
Perry Richard Gilbert
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Celanese Corp
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Celanese Corp
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Classifications

    • 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
    • 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
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • This invention is'concerned with improvements of hydroxylamine or hydrazine or derivatives ofw .10 these bodies with formaldehyde or other aldehydes or substances yielding or acting as alde hydes.
  • the reaction may be brought about in or on the textile materials themselves, and may take place in the presence of suitable catalysts,
  • reaction may, for example hydrochloric acid or other mineral acids or organic acids.
  • the reaction may, for example hydrochloric acid or other mineral acids or organic acids.
  • the invention includes not only hydroxylamine and hydrazine themselves as reagents, but also their derivatives, for example the organic derivatives such as alkyl, aryl, aralkyl and acidyl derivatives; the last, in the case of hydroxylamine derivatives, are usually knownas hydroxamic acids.
  • These organic derivatives as well as the hydroxylamine and hydrazine themselves have the general formula R1 80 N-x R. a a where R1 and R2 are hydrogen or organic radicles, e. g. those mentioned above, and X is-OH or NHa.
  • the radicles which are substituted for hydrogen 35 in the hydroxylamine or hydrazine may be, for v example, lower alkyl radicles such as methyl, ethyl, propyl, butyl and the like, or higher alkyl radicles, for example those 01 the alcohols ob tained by reduction of the higher fatty acids, for
  • the -reagents for the formation of the anti-creasing'substance may be applied in suc-' passion, and, after the application of each reagent, the material may be dried so as to cause the reagent to penetrate the fibre.
  • the material may be impregnated with the reagent under vacuum or with increased pressure. Subsequent release of pressure generally enables the flbreto take up excess material deposited between the fibres.
  • the fabric may be centrifuged, or excess of reagent pressed off, and the fabric then subjected to considerable pressure so as to squeeze out any substantial excess above the amount which the fibres themselves are able to absorb.
  • Mechanical pressure for example by means of heavy calender rolls, is usually most effective.
  • the invention may be applied quite broadly to improving the resistance to creasing of all kinds of textile material in which the natural resistance is deficient.
  • the invention contemplates improving the resistance to creasing of natural cellulosic materials, f )1" in'stancecotton .and linen and regenerated cellulosic materials, for instance viscose, cuprammonium and nitrocellulose artiflcial silks.
  • Cellulose acetate and like cellulose derivative materials are preferably subjected to a saponification treatment before applying the anti-crease treatment, the s'aponification being complete or partial, for example to a loss in weight of 15% or more in the case of cellulose acetate.
  • Low grade animal fibre materials may also have their properties improved. by the present invention.
  • Cellulose derivative materials may be caused .to absorb the reagents under swelling gonditions.
  • a swelling agent may be applied to the materials before or during the application of the reagents.
  • a aqueous solution of acetone or of dioxane is very suitable in the case of acetone-soluble cellulose acetate.
  • Such a solution may be applied to the material before impregnation withthe hy'droxylamine, hydrazine or derivative thereof, or the reagent may be dissolved in the swelling solution.
  • the materials to be treated may be subjected to any desired treatment designed to impart particular properties thereto.
  • artificial materials may be stretched before the treatment.
  • Cellulose derivative materials in particular are especially amenable to increase in tenacity by stretching, and reference is made in this connection toU. S.,applications S. Nos. 4,510 and 4,511 filed February 1, 1935.
  • Example 1 g A viscose fabrieQis soaked for about 5 minutes in a 5% solution of hydroxylamine hydrochloride.
  • a creaseless effect is thereby comprises incorporating in? the textile materials a reaction product of an aldehyde, width-a single substance capable of condensation therewith,
  • said substance being selected from the group comprises incorporating in the textile materials w a-reaction product of formaldehyde with a single consisting j'of hydroxylamine, hydrazine and aikyl, aryi, aralk'yl and acidyl derivatives of j'hydroxylamine and hydrazine.
  • tile materials a reaction product of formaldehyde with a single substance'capable of condensation therewith, said substance consisting of hydroxylamine, the incorporation being effected by im pregnating the material with a solution of a 30 hydroxylam ine salt, drying, impregnating with aqueous formaldehyde, again drying and heating to bring about condensation.
  • cellulosic textile tain a condensation product of. formaldehyde with a'single substance capable of conde tives of hydroxy-lamine and 1 hydrazine.

Description

Patented June '13, 1939 UNIT D STATES TREATDIENT F TEXTILE MATERIALS Donald Finlayson and Richard Gilbert Perry, Spondon, near Derby, England, assignors to Oelanese Corporation of America, a corporation oi Delaware No Drawing. Application July 29, 1936, Serial No. 93,230. In Great Britain September 11, 1935 Claim.
This invention is'concerned with improvements of hydroxylamine or hydrazine or derivatives ofw .10 these bodies with formaldehyde or other aldehydes or substances yielding or acting as alde hydes. The reaction may be brought about in or on the textile materials themselves, and may take place in the presence of suitable catalysts,
for example hydrochloric acid or other mineral acids or organic acids. The reaction, may, for
example, be effected by heating the textile materials carrying the reagents for a few minutes.
As previously indicated, the invention includes not only hydroxylamine and hydrazine themselves as reagents, but also their derivatives, for example the organic derivatives such as alkyl, aryl, aralkyl and acidyl derivatives; the last, in the case of hydroxylamine derivatives, are usually knownas hydroxamic acids. These organic derivatives as well as the hydroxylamine and hydrazine themselves have the general formula R1 80 N-x R. a a where R1 and R2 are hydrogen or organic radicles, e. g. those mentioned above, and X is-OH or NHa. The radicles which are substituted for hydrogen 35 in the hydroxylamine or hydrazine may be, for v example, lower alkyl radicles such as methyl, ethyl, propyl, butyl and the like, or higher alkyl radicles, for example those 01 the alcohols ob tained by reduction of the higher fatty acids, for
0 example the radicles of lauryl, oleyl, stearyl and substance in the textile fibre itself, and to avoid.
as far as possible its deposition between the 55 fibres. The -reagents for the formation of the anti-creasing'substance may be applied in suc-' passion, and, after the application of each reagent, the material may be dried so as to cause the reagent to penetrate the fibre. Alternatively or in addition, the material may be impregnated with the reagent under vacuum or with increased pressure. Subsequent release of pressure generally enables the flbreto take up excess material deposited between the fibres. For instance, after soaking a fabric in a solution or emulsion of the desired reagent, the fabric may be centrifuged, or excess of reagent pressed off, and the fabric then subjected to considerable pressure so as to squeeze out any substantial excess above the amount which the fibres themselves are able to absorb. Mechanical pressure, for example by means of heavy calender rolls, is usually most effective.
The invention may be applied quite broadly to improving the resistance to creasing of all kinds of textile material in which the natural resistance is deficient. In particular the invention contemplates improving the resistance to creasing of natural cellulosic materials, f )1" in'stancecotton .and linen and regenerated cellulosic materials, for instance viscose, cuprammonium and nitrocellulose artiflcial silks. Cellulose acetate and like cellulose derivative materials are preferably subjected to a saponification treatment before applying the anti-crease treatment, the s'aponification being complete or partial, for example to a loss in weight of 15% or more in the case of cellulose acetate. Low grade animal fibre materials may also have their properties improved. by the present invention.
Cellulose derivative materials may be caused .to absorb the reagents under swelling gonditions.
Thus, for example, a swelling agent may be applied to the materials before or during the application of the reagents. A aqueous solution of acetone or of dioxane is very suitable in the case of acetone-soluble cellulose acetate. Such a solution may be applied to the material before impregnation withthe hy'droxylamine, hydrazine or derivative thereof, or the reagent may be dissolved in the swelling solution.
The materials to be treated may be subjected to any desired treatment designed to impart particular properties thereto. For example, artificial materials may be stretched before the treatment. Cellulose derivative materials in particular are especially amenable to increase in tenacity by stretching, and reference is made in this connection toU. S.,applications S. Nos. 4,510 and 4,511 filed February 1, 1935.
The following examples illustrate the invention l with formaldehyde, drying the material and but are not intended to limit it in any way:
I Example 1 g A viscose fabrieQis soaked for about 5 minutes in a 5% solution of hydroxylamine hydrochloride.
It is then dried, dipped in a aqueous solution of formaldehyde, again dried, and heated at about for a shorter period. Example 2 130 C. for 5 minutes or temperature about 5 minutes. A creaseless effect is thereby comprises incorporating in? the textile materials a reaction product of an aldehyde, width-a single substance capable of condensation therewith,
' said substance being selected from the group comprises incorporating in the textile materials w a-reaction product of formaldehyde with a single consisting j'of hydroxylamine, hydrazine and aikyl, aryi, aralk'yl and acidyl derivatives of j'hydroxylamine and hydrazine. I i
2. Process for improving the resistance to creasing or crushing of textile materials .which droxylamine and*=with formaldehyde, drying the material and v heating for a short time to about condensation. I I I '4. Process for improving the resistance, to
5 creasing or crushing of cellulosic textilematerials which comprises incorporating in the tex- I tile materials a reaction product of formaldehyde with a single substance capable of condensation therewith,.said substance consisting of hydr A e, the incorporation being effected bysuc "vely soaking the textile material withhydraaine and heating for a short time'to bring about condensation.
5. Process for improving the creasing 'or crushing of cellulosic textile mate- '5- rials which comprises incorporating in the textile materials a reaction product 'of formaldehyde with a single substance capable of condensation therewith, said substance consisting of hydroxylaminathe incorporation beingeffected 10 creasing or crushing of cellulosic textile mate- 15 rials which comprises incorporating in the textile materials a reaction product of formaldehyde with a single substance capable of condensation therewith, said substance consisting of hydrazine,
"the incorporation being eifected by impregnation 20 of the material with hydrazine and formaldehyde followed by heating for a short time.
I '1. Process for improving the resistance to creasing or crushing of cellulosic textile materials which comprises incorporating in the. tex-.-
tile materials a reaction product of formaldehyde with a single substance'capable of condensation therewith, said substance consisting of hydroxylamine, the incorporation being effected by im pregnating the material with a solution of a 30 hydroxylam ine salt, drying, impregnating with aqueous formaldehyde, again drying and heating to bring about condensation.'
8. Process for improving the resistance to,
creasing or crushing of textile materials which 5 comprises incorporating in'the textile materials a reaction'product of formaldehyde with a single substance capable of condensation therewith, said substance consisting of hydrazine? 9. Process :for improving the resistance to creasing or'crushing of cellulosic textile materials which comprises incorporating in. the textile materialsia reaction product of formaldehyde with a single substance capable of condensation therewith, said substance of hydrazine,-
the incorporation being effected byv impregnating the materialv with a solution of a hydrazine salt,
drying, impregnating with aqueous formaldehy'de, again drying and heating to bring about condensation 10. cellulosic textile tain a condensation product of. formaldehyde with a'single substance capable of conde tives of hydroxy-lamine and 1 hydrazine.
DONALD maYsoN. RICHARD GILBERT PERRY.
the group "consisting of hydroxylamine, hydrazine andsalkyl, aryi, aralkyl and acidyideriva-
US93230A 1935-09-11 1936-07-29 Treatment of textile materials Expired - Lifetime US2161808A (en)

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2464342A (en) * 1943-04-16 1949-03-15 Frederick F Pollak Manufacture of waterproof and water-repellent noninflammable fibrous materials
US2497601A (en) * 1943-03-30 1950-02-14 Melle Usines Sa Purification of ether
US2500822A (en) * 1947-02-27 1950-03-14 Socony Vacuum Oil Co Inc Thenaldimines
US2596268A (en) * 1948-02-06 1952-05-13 Hendrik W Meijer Creaseproofing cellulose textiles with glucose-ureide formaldehyde condensation product
US2784174A (en) * 1952-07-09 1957-03-05 Socony Mobil Oil Co Inc Condensation products of thiophenes with formaldehyde and hydroxylamine salts
US2904388A (en) * 1957-05-10 1959-09-15 Olin Mathieson Composition and process for crease-and wrinkleproofing cellulosic textile material
US2904389A (en) * 1958-12-09 1959-09-15 Olin Mathieson Composition of matter useful in rendering cellulose resistant to creasing and wrinkling
US2904390A (en) * 1958-12-09 1959-09-15 Olin Mathieson Method to render cellulose resistant to creasing and wrinkling and the product thereof
US2904387A (en) * 1958-04-28 1959-09-15 Olin Mathieson Composition and process for crease- and wrinkleproofing cellulosic textile material
US2940843A (en) * 1954-03-16 1960-06-14 Aerojet General Co Rocket propellant fuel
US3215651A (en) * 1961-08-25 1965-11-02 Rubber Res Inst Of Malaya Hydrazine-formaldehyde as a reinforcing agent for rubber latex foam
US3234164A (en) * 1955-03-23 1966-02-08 Degussa Conversion of non-fusible and insoluble polyacroleins with hydroxyl amine
US3284234A (en) * 1963-09-03 1966-11-08 Olin Mathieson Stabilized cellulosic material
US3326630A (en) * 1964-02-05 1967-06-20 Olin Mathieson Modification of wool with solution containing formaldehyde and the reaction product of formaldehyde with a monohydrazide or a dihydrazide
EP3712254A1 (en) 2014-05-28 2020-09-23 Children's Hospital Medical Center Methods and systems for converting precursor cells into gastric tissues through directed differentiation

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2870056A (en) * 1954-09-21 1959-01-20 Monsanto Chemicals Fungicidal compositions comprising the mono-phenylhydrazones of alpha-diketones, alpha-ketoaldehydes, and alpha-hydroxyketones
US2844505A (en) * 1954-09-21 1958-07-22 Monsanto Chemicals Fungicidal compositions comprising phenylosazones

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2497601A (en) * 1943-03-30 1950-02-14 Melle Usines Sa Purification of ether
US2464342A (en) * 1943-04-16 1949-03-15 Frederick F Pollak Manufacture of waterproof and water-repellent noninflammable fibrous materials
US2500822A (en) * 1947-02-27 1950-03-14 Socony Vacuum Oil Co Inc Thenaldimines
US2596268A (en) * 1948-02-06 1952-05-13 Hendrik W Meijer Creaseproofing cellulose textiles with glucose-ureide formaldehyde condensation product
US2784174A (en) * 1952-07-09 1957-03-05 Socony Mobil Oil Co Inc Condensation products of thiophenes with formaldehyde and hydroxylamine salts
US2940843A (en) * 1954-03-16 1960-06-14 Aerojet General Co Rocket propellant fuel
US3234164A (en) * 1955-03-23 1966-02-08 Degussa Conversion of non-fusible and insoluble polyacroleins with hydroxyl amine
US2904388A (en) * 1957-05-10 1959-09-15 Olin Mathieson Composition and process for crease-and wrinkleproofing cellulosic textile material
US2904387A (en) * 1958-04-28 1959-09-15 Olin Mathieson Composition and process for crease- and wrinkleproofing cellulosic textile material
US2904389A (en) * 1958-12-09 1959-09-15 Olin Mathieson Composition of matter useful in rendering cellulose resistant to creasing and wrinkling
US2904390A (en) * 1958-12-09 1959-09-15 Olin Mathieson Method to render cellulose resistant to creasing and wrinkling and the product thereof
US3215651A (en) * 1961-08-25 1965-11-02 Rubber Res Inst Of Malaya Hydrazine-formaldehyde as a reinforcing agent for rubber latex foam
US3284234A (en) * 1963-09-03 1966-11-08 Olin Mathieson Stabilized cellulosic material
US3326630A (en) * 1964-02-05 1967-06-20 Olin Mathieson Modification of wool with solution containing formaldehyde and the reaction product of formaldehyde with a monohydrazide or a dihydrazide
EP3712254A1 (en) 2014-05-28 2020-09-23 Children's Hospital Medical Center Methods and systems for converting precursor cells into gastric tissues through directed differentiation

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