US3427122A - Sizing compositions containing acrylamide and dimethylolated acetylene mono-ureine - Google Patents

Sizing compositions containing acrylamide and dimethylolated acetylene mono-ureine Download PDF

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Publication number
US3427122A
US3427122A US498081A US3427122DA US3427122A US 3427122 A US3427122 A US 3427122A US 498081 A US498081 A US 498081A US 3427122D A US3427122D A US 3427122DA US 3427122 A US3427122 A US 3427122A
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United States
Prior art keywords
acrylamide
ureine
acetylene
mono
dimethylolated
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Expired - Lifetime
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US498081A
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English (en)
Inventor
Pierre Talet
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Nobel Bozel SA
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Nobel Bozel SA
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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/402Amides imides, sulfamic acids

Definitions

  • a cellulose textile dressing composition comprising a condensate of one mole of dimethylolated acetylene-mono-ureine and 0.01 to 0.10 mole acrylamide, and a catalyst of glyoxylic acid.
  • the present invention relates to improvements in sizing compositions containing acrylamide and acetylene-monoureme.
  • methylolated derivatives AMU/AA-m
  • AMU/AA-m methylolated derivatives
  • AMU-m dimethylolated acetylene-mono-ureine
  • AMU-m dimethylolated acetylene-mono-ureine
  • the methylolated products (AMU/AA-m) can be prepared in situ, for example by simultaneous condensation of urea with glyoxal (the two being constituents of acetylene-mono-ureine), acrylamide and formaldehyde.
  • Such an in situ preparation may be considered as industrially advantageous since it reduces the cost of the AMU/AA-m product.
  • acrylamide still remains a relatively costly product and the amount used in the reaction is large since one gram-molecule of acrylamide should be present for one gram-molecule of acetylenemono-ureine.
  • An object of the invention is to provide a highly effective yet inexpensive sizing for cellulose textile materials.
  • AMU-m dimethylolated acetylene-mono-ureine
  • the textile sizing product of my invention is consequently essentially dimethylolated acetylene-mono-ureine modified by incorporating acrylamide in an amount less than one gram-molecule of acrylamide for one grammolecule of dimethylolated acetylene-mono-ureine.
  • the acrylamide associated with dimethylolated acetylenemono-ureine is in a free state or in a combined state.
  • the amount of acrylamide used is advantageously between 0.08 and 0.1 gram-molecule per gram-molecule of the dimethylolated acetylene-mono-ureine.
  • the sizing product according to the invention may be easily prepared, in situ, by condensation of urea with 3,427,122 Patented Feb. 11, 1969 glyoxal (constituents of acetylene-mono-ureine) followed by condensation with formaldehyde and with a suitable amount of acrylamide, for example, n/ 10 gram-molecule (moles) of acrylamide or less, for n gram-molecule (moles) of AM'U-m; there is thus formed in situ a very low proportion (equal to or less than n/ 10 gram-molecule) of AMU/AA-m, the rest of the mixture being constituted by dimethylolated acetylene-mono-ureine (AMU-m).
  • AMU-m dimethylolated acetylene-mono-ureine
  • the process for preparing a sizing product comprises condensing a molecular equivalent of urea with a molecular equivalent of glyoxal, then with 0.08 to 0.1 molecular equivalent of acrylamide and a sufiicient amount of formaldehyde for obtaining a complete methylolation, formaldehyde being used in slight excess with respect to the amount theoretically necessary for obtaining such methylolation.
  • one molecular equivalent of urea is condensed with one molecular equivalent of glyoxal, then with a sufiicient amount of formaldehyde for obtaining a complete methylolation, the formaldehyde being used in a slight excess with respect to the amount theoretically necessary for obtaining such methylolation.
  • Dimethylolated acetylene-mono-ureine is then obtained; the latter is then mixed at ambient temperature with a suitable amount of acrylamide, advantageously from 0.08 to 0.1 tmolecular equivalent.
  • a further object of the invention is to provide a process for treating cellulose textile materials with the above described sizing product, such process being essentially characterized by the fact that, in order to bind said sizing product, a catalyst constituted by glyoxylic acid or by a composition containing glyoxylic acid is used.
  • compositions which may be used include, besides solutions of glyoxylic acid itself, a mixture of glyoxylic acid with zinc nitrate and trichloro acetic acid or the like.
  • the solution containing the active sizing compound is brought up to the desired dilution by adding water after which'the catalyst is dissolved therein together with other desired additives.
  • the textile material is then impregnated with the thus obtained solution and then the remainder process treatment is carried out in a conventional manner.
  • Example 1 concerns the preparation, in situ, in accordance with the invention of a size constituted by dimethylolated acetylene-mono-ureine chemically combined with a small amount of acrylamide.
  • Example 2 concerns the preparation, in situ, and in accordance with the invention, of a size comprising dimethylolated acetylene-mono-ureine and a small amount of free acrylamide.
  • Example 3 concerns the preparation of a control size constituted by dimethylolated acetylene-mono-ureine without any acrylamide.
  • Example 1 of formaldehyde (40% by volume-36.5% by weight) are added.
  • the pH of the solution is brought up to 8.38.4 by the addition of hydrated barium hydroxide.
  • the term perature is from 18 to 20 C.
  • Example 2 Example 1 is repeated except that acrylamide is not condensed by heating with dimethylolated acetylenemono-ureine. It is simply introduced at the end of the run.
  • Example 3 Example 1 is repeated but in the absence of acrylamide.
  • Test series II The same series of tests was carried out using three solutions containing 125 gms. per litre (the first containing the product of Example 1, the second the product of Example 2 and the third the product of Example 3) but using 18% by weight of a catalyst of formula:
  • the non-creasing of the fabric is detennined with the DAM apparatus in accordance With I.T.F. specifications which are quite similar to those of AATCC 66-1959T specifications. Generally speaking, this property is expressed by the value of a residual angle of the fabric previously folded under standard conditions.
  • the washings are effected in a washing machine provided with a reciprocating drum over a period of 10 minutes at 80 C.
  • a mixture of soap and sodium carbonate is used.
  • the scorch tester apparatus is used in accordance with the AATCC92 specifications. In accordance with this test samples are treated with hypochlorite then, after drying, they are heated between the two plates of the scorch tester at 180 C. The loss of mechanical strength is then measured and is expressed as loss with respect to treated samples not submitted to the scorch tester.
  • Test series III The resistance of the sizes to acidic hydrolysis was studied using the following method:
  • the fabrics are passed in baths containing 160 gms. per litre of the methylolated derivatives corresponding to the above examples in the presence of catalyst I or catalyst II.
  • Table II gives the angles of crease in the dry state of fabrics which have been sized and submitted to said acidic treatment together with the loss of the non-creasing properties expressed in with respect to the gain of the noncreasing properties obtained with the size without acidic treatment (as such).
  • Test series IV The action of chlorine on these fabrics which have been submitted to an acidic washing step under the conditions specified was applied in accordance with the AATCC92- 1962 specifications and evaluated in the scorch tester. The results obtained are given in Table III.
  • Example 4 Example 1 is repeated except that 0.6 mole of acrylamide is used instead of 0.172 mole. Results similar to those shown in Tables I, II, and III for the product of Example 1 are obtained.
  • Example 5 Example 2 is repeated except that 0.6 mole of acrylamide is used instead of 0.172 mole. Results similar to those shown in Tables I, II and III for the product of Example 2 are obtained.
  • a dressing composition for textiles consisting essentially of dimethylolated acetylenemono-ureine and acrylamide, said acrylamide being present in an amount between 0.01 and 0.10 moles per mole of dimethylolated acetylene-mono-ureine.
  • a dressing composition for textiles consisting essentially of a condensate of one mole of acetylene-monoureine, a molar excess of formaldehyde and 0.01 to 0.10 of acrylamide, and a catalyst of glyoxylic acid.
  • a dressing composition comprising condensing urea with glyoxal to provide acetylenemono-ureine, condensing from 0.01 to 0.10 mole of acrylamide with each mole of acetylene-mono-ureine, and then condensing the reaction product of acrylamide and acetylene-mono-ureine with a molar excess of formaldehyde.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US498081A 1965-04-30 1965-10-19 Sizing compositions containing acrylamide and dimethylolated acetylene mono-ureine Expired - Lifetime US3427122A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR15467A FR1450514A (fr) 1965-04-30 1965-04-30 Compositions d'apprêt à base d'acrylamide et d'acétylène-mono-uréine

Publications (1)

Publication Number Publication Date
US3427122A true US3427122A (en) 1969-02-11

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US498081A Expired - Lifetime US3427122A (en) 1965-04-30 1965-10-19 Sizing compositions containing acrylamide and dimethylolated acetylene mono-ureine

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US (1) US3427122A (fr)
BE (1) BE677619A (fr)
CH (1) CH465550A (fr)
DE (1) DE1619123A1 (fr)
ES (1) ES325597A1 (fr)
FR (1) FR1450514A (fr)
GB (1) GB1131620A (fr)
LU (1) LU50637A1 (fr)
NL (1) NL6605693A (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2173005A (en) * 1936-07-08 1939-09-12 Du Pont Resinous products from aldehydes and acrylic amides
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products
US2885438A (en) * 1952-11-26 1959-05-05 Ciba Ltd Process for the preparation of polymer-izable acrylamido methylene ureas
US3024246A (en) * 1959-03-11 1962-03-06 Union Carbide Corp Certain nu-methylol-nu-(3-methylol imidazolidon-2-yl) ethyl acylamides and process
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins
US3246946A (en) * 1961-05-09 1966-04-19 Rohm & Haas Method of crease-proofing cellulosic fabrics and fabrics obtained
US3363973A (en) * 1962-12-28 1968-01-16 Nobel Bozel Condensation products of acrylamide with acetylene-mono-ureine

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2173005A (en) * 1936-07-08 1939-09-12 Du Pont Resinous products from aldehydes and acrylic amides
US2885438A (en) * 1952-11-26 1959-05-05 Ciba Ltd Process for the preparation of polymer-izable acrylamido methylene ureas
US2876062A (en) * 1953-09-03 1959-03-03 Phrix Werke Ag Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products
US3024246A (en) * 1959-03-11 1962-03-06 Union Carbide Corp Certain nu-methylol-nu-(3-methylol imidazolidon-2-yl) ethyl acylamides and process
US3246946A (en) * 1961-05-09 1966-04-19 Rohm & Haas Method of crease-proofing cellulosic fabrics and fabrics obtained
US3209010A (en) * 1961-11-13 1965-09-28 Gagliardi Res Corp Polyalkylated monoureins
US3363973A (en) * 1962-12-28 1968-01-16 Nobel Bozel Condensation products of acrylamide with acetylene-mono-ureine

Also Published As

Publication number Publication date
BE677619A (fr) 1966-09-12
LU50637A1 (fr) 1967-09-11
CH361466A4 (fr) 1968-08-15
DE1619123A1 (de) 1970-03-26
ES325597A1 (es) 1967-02-16
GB1131620A (en) 1968-10-23
FR1450514A (fr) 1966-06-24
CH465550A (fr) 1969-01-15
NL6605693A (fr) 1966-10-31

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