US2596268A - Creaseproofing cellulose textiles with glucose-ureide formaldehyde condensation product - Google Patents

Creaseproofing cellulose textiles with glucose-ureide formaldehyde condensation product Download PDF

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Publication number
US2596268A
US2596268A US70585A US7058549A US2596268A US 2596268 A US2596268 A US 2596268A US 70585 A US70585 A US 70585A US 7058549 A US7058549 A US 7058549A US 2596268 A US2596268 A US 2596268A
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United States
Prior art keywords
ureide
glucose
formaldehyde
cellulose
creaseproofing
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Expired - Lifetime
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US70585A
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English (en)
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Hendrik W Meijer
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Classifications

    • 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
    • D21H17/20—Macromolecular organic compounds
    • D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
    • D21H17/24—Polysaccharides
    • 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
    • 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
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones
    • D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
    • D21H17/50—Acyclic compounds

Definitions

  • My invention relates to a process for treatin cellulosic material, as well as to the material thus treated.
  • cellulosic material rayon, linen, jute, flax, hemp, cotton, paper, cardboard and the like.
  • the material may be in the form of fibres, threads, yarns, fabrics, lengths, sheets, shaped articles and the like. It may also consist wholly or partly of regenerated cellulose.
  • the process according to my invention is of the last-mentioned kind, and consists in the cellulosic material being treated, in the presence of aldehydes or compounds forming aldehydes during the treatment, at a pH less than 2.0, with a solution of nitrogen-containing reaction products formed with liberation of water from aldoses or ketoses with at least four carbon atoms in the molecule and organic compounds containing at least one NH: group and either at least one other NHz group or at least a mono-substituted NI-Iz group.
  • the said nitrogen-containing reaction products can be obtained by reaction of the said aldoses or ketoses in the presence of a dehydrating agent a 2 with the organic compounds containing at least one NH: group and either at least one other NH: group or at least a mono-substituted NH: group.
  • R represents hydrogen, an alkyl-, aryl-, or an alkyl-aryl group and G represents the glucosyl radical.
  • suitable aldoses and ketoses are hexoses, such as glucose, galactose, mannose and fructose.
  • hexoses such as glucose, galactose, mannose and fructose.
  • polysaccharides which hydrolyse under the reaction conditions to hexoses, such as cane sugar or maltose.
  • organic compounds containingat least one free NH2 group and at least one unsubstituted or mono-substituted NI-Iz group are urea, thiourea and guanidine, as well as their alkyl-, aryl-, or alkyl-aryl derivatives monosubstituted in an NHz group, such as methyland butyl-urea, and substituted or unsubstituted melamines and diamides.
  • This compound is formed by a condensation in weak alkaline medium which is known in itself. It was found that in a weak acid medium the addition product is even formed instantaneously at room temperature. Even in a very strong acid medium no polycondensation to a water-insoluble compound can occur, and also not in the presence of a great excess of formaldehyde, for example an at least five-fold molar excess, as is preferably applied according to my invention.
  • cellulosic material is introduced into such a solution at a pH of 2 and is dried after pressing out at elevated temperature, e. g. 90 C., combination with the fibre will take place by the formation of methyl-glucose-ureide bridges between two cellulose chains.
  • bridges are formed by reaction of the formaldehyde with reactive NH groups of the methylglucose-ureide on the one hand and with hydroxy groups of the cellulose chains on the other hand; in other words, the hydrogen atoms which are connected to nitrogen will be replaced by hyv droxy-methyl groups, whereafter the hydroxymethyl groups thus formed form bridges with the hydroxy groups of the cellulose, water being split off according to the following schematic representation, in which -R- represents the cellulose chain:
  • the treatment should be carried out at a low pH (2 or less) to accomplish a reaction with the cellulose chains.
  • the pH used is preferably between 1 and 2. It can be obtained by the addition of strong acids, but according to a further feature of my invention itis preferred to establish the low pH gradually during the treatment by means of compounds, such as ammonium salts of strong acids, which bring about the required low pH during the, treatment by reaction with aldehydes, such as formaldehyde.
  • the bath should adjust itself to this low pH. very slowly, which can beensured by the addition of a bufferas compound such as triethanolamine. The re?
  • quired low pH value can also be obtained by the addition of compounds such as monochloroacetamide, beta-chlorohydrocinnamic acid, whichrrelease the required quantityof acid upon heating.
  • compounds such as monochloroacetamide, beta-chlorohydrocinnamic acid, whichrrelease the required quantityof acid upon heating.
  • Formaldehyde and glyoxal are suitable aldehydes.
  • aldehydes instead of aldehydes, compounds forming aldehydes during the treatment can also be used. Para-formaldehyde and methyl acetamide are examples of such compounds.
  • a rayon fabric is passed at room temperature through the solution thus obtained and is squeezed "out to a 100 percent wet pick-up and isthendriedforl0nr1inutes'at-90 C. at a pH of about 2.
  • the fabric is subsequently washed for one minute at'70 C., to remove free formaldehyde and'further chemicals, with an aqueous solution of 011 per cent-of soap and 0.1 per cent of soda. After rinsing with lukewarm water for some-minutes,'the fabric is dried below 100 C.
  • the fabric thus obtained is practically uncreasable after 24 hours conditioning, does not shr-lnlo'when washed and has increased 13' per 4 cent in weight, which increase, as well as the uncreasability itself, is permanent to washing.
  • Example II 120 grams of pure glucose-ureide is dissolved at room temperature in 400 cos. of an aqueous 40 formaldehyde solution. The mixture is then diluted with 3100 ccs. of water, whereupon a solution of 10 grams. of ammonium chloride in grams of water is added. A piece of paper was immersed in this solution for a few seconds and subsequently squeezed out to a per cent wet pick-up, after which it was dried for 3 minutes, at 90 C. at a pH of 2.5. The paper thus obtained has increased 3 per cent in weight, and has a much greater strength in the wet condition than before the treatment and a greater resistance to folding.
  • Example III A solution was prepared as in Example I. b t with this difference: that instead of grams of pure glucose-ureide, grams of a clear syrup, obtained by condensation of can sugar with urea, was used.
  • a process for chemically fixing onto. cellulose fibers a ureide selected from the group con-, sisting of the ureides of the methylol-ketoses, and methylol-aldoses which comprises treating. the cellulose fibers at a pH between 1 and 2 with the said ureide in the presenceof a member selected from the groupconsisting of formaldehyde and formaldehyde-yielding compounds, at a temper ature of about 90 C. whereby the resultant chemical linkage with the cellulosev is permanent and fast. to washing.
  • a process for chemically fixing, methylolglucose ureide onto cellulose fibers which comprises treating the latter at a pH between 1 and 2 with the said ureide in, the presence of free'forme aldehyde ata temperature. of about 90 0., whereby theresultant chemical linkage. with the. cellulose is permanent to washing.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US70585A 1948-02-06 1949-01-12 Creaseproofing cellulose textiles with glucose-ureide formaldehyde condensation product Expired - Lifetime US2596268A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL676419X 1948-02-06

Publications (1)

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US2596268A true US2596268A (en) 1952-05-13

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US (1) US2596268A (en(2012))
GB (1) GB676419A (en(2012))
NL (1) NL72024C (en(2012))

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2808404A (en) * 1953-05-11 1957-10-01 Gen Mills Inc Sulfated fatty urea nu-glycosides
US3135710A (en) * 1960-09-22 1964-06-02 Rohm & Haas Aqueous dispersion of aminoplast and butene-2-diol-1, 4

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB209697A (en) * 1922-08-11 1924-01-11 John Stogdell Stokes Improvements in and relating to synthetic resins and the process of making same
GB450620A (en) * 1935-01-21 1936-07-21 British Celanese Process for the improvement of textile materials
FR813990A (fr) * 1936-02-15 1937-06-12 Zundel Lab Procédé de traitement de tissus donnant un apprêt souple, permanent et infroissable
GB480958A (en) * 1935-08-30 1938-02-28 Pagani & C Improvements in or relating to the production and application of synthetic resins made from carbohydrate ureide and formaldehyde
US2161808A (en) * 1935-09-11 1939-06-13 Celanese Corp Treatment of textile materials
US2203492A (en) * 1937-06-30 1940-06-04 Ici Ltd Dyed cellulosic material

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB209697A (en) * 1922-08-11 1924-01-11 John Stogdell Stokes Improvements in and relating to synthetic resins and the process of making same
GB450620A (en) * 1935-01-21 1936-07-21 British Celanese Process for the improvement of textile materials
GB480958A (en) * 1935-08-30 1938-02-28 Pagani & C Improvements in or relating to the production and application of synthetic resins made from carbohydrate ureide and formaldehyde
US2145695A (en) * 1935-08-30 1939-01-31 Mattiotto Paolo Process for manufacturing water soluble artificial resins for treating textiles
US2161808A (en) * 1935-09-11 1939-06-13 Celanese Corp Treatment of textile materials
FR813990A (fr) * 1936-02-15 1937-06-12 Zundel Lab Procédé de traitement de tissus donnant un apprêt souple, permanent et infroissable
US2203492A (en) * 1937-06-30 1940-06-04 Ici Ltd Dyed cellulosic material

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2808404A (en) * 1953-05-11 1957-10-01 Gen Mills Inc Sulfated fatty urea nu-glycosides
US3135710A (en) * 1960-09-22 1964-06-02 Rohm & Haas Aqueous dispersion of aminoplast and butene-2-diol-1, 4

Also Published As

Publication number Publication date
GB676419A (en) 1952-07-30
NL72024C (en(2012))

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