US3650671A - Process for finishing cellulosic textile materials with n-methylol compounds - Google Patents

Process for finishing cellulosic textile materials with n-methylol compounds Download PDF

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Publication number
US3650671A
US3650671A US807402A US3650671DA US3650671A US 3650671 A US3650671 A US 3650671A US 807402 A US807402 A US 807402A US 3650671D A US3650671D A US 3650671DA US 3650671 A US3650671 A US 3650671A
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United States
Prior art keywords
cross
acid
linking
acetic acid
textile material
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Expired - Lifetime
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US807402A
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English (en)
Inventor
Gerhard Bergmann
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Hoesch Chemie GmbH
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Hoesch Chemie GmbH
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    • 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
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins

Definitions

  • the invention relates to the finishing of textiles in the process of wet, damp or dry cross-linking with nitrogen-containing methylol compounds.
  • the acid catalysis has the effect of causing the reaction of the methylol group with the hydroxyl group of the cellulose, which has the effect of cross-linking the cellulose.
  • crosslinking catalysts there are used inorganic acids, such as hydrochloric acid alone or in combination with suitable organic acids.
  • the dry cross-linking method it is conventional to carry out the process in the presence of salts which are acid-reacting under the effect of heat. After the cross-linking step has been carried out, it is necessary in the wet or damp cross-linking process to neutralize the acids and to remove them from the textile goods in order to avoid damaging the fibers, which could result from an extended effect of the acids thereon. In contrast to the dry cross-linking method, it is necessary in the damp or wet cross-linking process to follow with an additional past-processing step as well as with a second drying step, which both are required as a result of the required abovediscussed neutralization. Accordingly, this procedure requires additional chemicals and drying energy.
  • the object of the invention is to overcome the drawbacks of the known method.
  • a method is provided whereby two steps in the above-described conventional process are omitted, namely, the neutralization step and the following required drying step.
  • thermally unstable acids such as organic acids like trichloracetic acid, mesoxalic acid, propiolic acid, tetrolic acid, acetoacetic acid, ethanetricarbonic acid or malonic acid. These acids may be used in amounts of to 50 g./l.
  • organic acids like trichloracetic acid, mesoxalic acid, propiolic acid, tetrolic acid, acetoacetic acid, ethanetricarbonic acid or malonic acid.
  • these acids may be used in amounts of to 50 g./l.
  • Preferred amongst the various organic, heat-sensitive acids is trichloracetic acid because it decomposes into chloroform and carbon dioxide at a temperature in the range of about 80 to 100 C., in a time dependent reaction.
  • the salts of this acid form carbonate.
  • trichloracetic acid in combination with one of its salts, the acid residue is neutralized concurrently with the decomposition of the acid-forming carbonate of the acid. In this manner, it is possible to shorten the duration of the necessary time for the heat treatment when causing a neutral textile reaction.
  • Any salt of trichloracetic acid which is heat decomposable can be used including the metal salts thereof like alkaline-, alkaline-earth-, ammonium-, aluminum-, amine-, heavy metal-, sodium or potassium salts.
  • hydrochloric acid phosphoric acid, tartaric acid, and an alkane sulfonic acid or aryl sulfonic acid like ethane or toluene sulfonic acids.
  • the decomposition of the acid is accomplished by subjecting the mixture to a short heat treatment at a temperature of about 130 to 140 C.
  • the decomposition of the thermally unstable acid, after it has effectuated its function as a cross-linker, can also be effectuated by holding the temperature at elevated temperatures for a longer period of time.
  • the textile which is impregnated with the cross-linking catalyst for the synthetic resin and with the conventional additives be cured by subjecting it to a holding period after it has been reduced to a residual water content. Then the textile is subjected to a short additional thermal post-treatment.
  • the thermal post-treatment can also follow directly the drying to the desired residual humidity and, thus the holding or curing period can be omitted.
  • the drying and the heat treatment of the impregnated textile goods can be carried out in one process step.
  • composition of the acid-salt mixture is so selected that after the thermal treatment in accordance with the invention, an alkaline reaction of the fiber is established.
  • chloroform vapors which are generated upon the decomposition of trichloracetic acid are removed in accordance with conventional procedures used in finishing textiles, such as by suction from the dry goods so that the process can be carried out under all the requisite safety requirements.
  • the invention involves the use of a heat-decomposable acid or its salts in a known process in substitution for the known acidic catalysts.
  • a heat-decomposable acid or its salts are particularly well suited.
  • those acids or their salts which decarboxylate into gases, such as CO upon heating to about C. or higher and which therefore are the equivalent of trichloracetic acid or malonic acid and their respective salts.
  • oxalic acid and its salts can be used.
  • EXAMPLE 1 A mercerized and bleached cotton fabric is treated with 200 g./l. of a 50% dimethyloldihydroxyethylene urea 35 g./l. of trichloracetic acid, and
  • the impregnated fabric is heated to C. for 20 seconds, dried to a residual water content of 8% and, after a 20-hour curing period, the fabric is subjected for one minute to a temperature of C.
  • EXAMPLE 3 Another similar cotton textile material is treated as above, the catalyst mixture is trichloracetic acid in an amount of 20 g./l.
  • the products exhibit upon a neutral reaction the characteristic values for a wet cross-linking.
  • the acid content of the textile pieces showed a loss of only 10% under the stated conditions.
  • the major amount of the tri-chloracetic acid was removed upon the thermal post-treatment which followed.
  • the amount of acid used can vary over wide ranges such as to 80 g./l., preferably to 50 g./l. of the liquid mixture for treating the textile.
  • the potassium salt thereof can be used.
  • EXAMPLE 6 The same fabric as in Example 1 is treated with a catalyst mixture of I50 g./l. ofa 50% methylolacryl amide 20 g./l. of trichloracetic acid, and
  • the fabric is foulardised, dried at 80 C., subjected to a thermal treatment at 150 C. for 5 minutes and steamed at 43 p.s.i. for 2 minutes.
  • Example l is repeated using 36.5 g./l. of sodium salt of trichloracetic acid and 10 g./l. ofoxalic acid, or
  • a textile finishing process by cross-linking a textile material comprising a cellulosic textile by the reaction with a resin-forming, cross-linking nitrogen-containing methylol compound in the presence of an acid cross-linking catalyst
  • the improvement which comprises carrying out said crosslinking reaction in the presence of an acid cross-linking catalyst selected from the following: trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa cross-linking acid and a salt of trichloro acetic acid, and heating the cross-linked textile material to decompose the crosslinking catalyst, thereby eliminating subsequent neutralization of the cross-linked textile material.
  • a process for the finishing of a textile material comprising a cellulosic textile, the steps which comprise impregnating the textile material with an aqueous solution comprising a cross-linking, resin'forming, nitrogen-containing methylol compound and an acid cross-linking catalyst selected from the group consisting of trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa thermally unstable cross-linking acid and a salt of trichloro acetic acid and heating and drying the impregnated textile material to cause cross-linking of the textile material with the nitrogencontaining methylol compound and to decompose the crosslinking catalyst.
  • an acid cross-linking catalyst selected from the group consisting of trichloro acetic acid, a mixture of trichloro acetic acid and its salts, and a mixture ofa thermally unstable cross-linking acid and a salt of trichloro acetic acid

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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)
US807402A 1968-03-16 1969-03-14 Process for finishing cellulosic textile materials with n-methylol compounds Expired - Lifetime US3650671A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1719546A DE1719546C3 (de) 1968-03-16 1968-03-16 Verfahren zur Hochveredlung von Textilien

Publications (1)

Publication Number Publication Date
US3650671A true US3650671A (en) 1972-03-21

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US807402A Expired - Lifetime US3650671A (en) 1968-03-16 1969-03-14 Process for finishing cellulosic textile materials with n-methylol compounds

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US (1) US3650671A (es)
AT (1) AT301484B (es)
BE (1) BE729664A (es)
CH (1) CH235169D (es)
DE (1) DE1719546C3 (es)
FR (1) FR2004050A1 (es)
GB (1) GB1221751A (es)
NL (1) NL6904030A (es)
SE (1) SE366784B (es)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849066A (en) * 1972-09-13 1974-11-19 Us Agriculture Method of increasing covering power of knitted cotton fabric
US3910760A (en) * 1973-05-14 1975-10-07 Us Agriculture Azeotropic solvents for permanent press treatments of cotton and cotton blend fabrics
US3933426A (en) * 1972-10-07 1976-01-20 Ciba-Geigy Corporation Process for making textiles containing cellulose crease-resistant
WO2007136384A1 (en) * 2006-05-19 2007-11-29 The Procter & Gamble Company Textile benefit compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2616983C2 (de) * 1976-04-17 1978-12-07 Hoechst Ag, 6000 Frankfurt Verfahren zum gemeinsamen Fixieren und Kondensieren von Pigmentdrucken bzw. Klotzfärbungen und Hochveredlungsprodukten

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837512A (en) * 1954-11-03 1958-06-03 Du Pont Activated cellulose ethers and process of preparing same
US3120507A (en) * 1959-10-23 1964-02-04 Ici Ltd Dyestuffs having a pyrimidine ring substituted by two halogen atoms and by a cyano group in the 5-position
US3518042A (en) * 1966-04-28 1970-06-30 Stevens & Co Inc J P Storable polymeric compositions and processes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR887537A (fr) * 1941-11-20 1943-11-16 Spinnfaser Ag Procédé d'amélioration de filés en cellulose hydratée par un traitement à la formaldéhyde en solution
NL107002C (es) * 1952-06-04 1900-01-01
NL247426A (es) * 1958-09-24
US3138802A (en) * 1962-05-25 1964-06-30 Cotton Producers Inst Of The N Process for imparting durable creases, wrinkle resistance and shape retention to cellulosic textile articles
FR1491628A (fr) * 1965-08-10 1967-08-11 Basf Ag Procédé perfectionné pour l'apprêtage irrétrécissable et sans repassage des tissus

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837512A (en) * 1954-11-03 1958-06-03 Du Pont Activated cellulose ethers and process of preparing same
US3120507A (en) * 1959-10-23 1964-02-04 Ici Ltd Dyestuffs having a pyrimidine ring substituted by two halogen atoms and by a cyano group in the 5-position
US3518042A (en) * 1966-04-28 1970-06-30 Stevens & Co Inc J P Storable polymeric compositions and processes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. T. Marsh, Crease Resisting Fabrics, 1962, Reinhold Publishing Corp., New York, pp. 112 119. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3849066A (en) * 1972-09-13 1974-11-19 Us Agriculture Method of increasing covering power of knitted cotton fabric
US3933426A (en) * 1972-10-07 1976-01-20 Ciba-Geigy Corporation Process for making textiles containing cellulose crease-resistant
US3910760A (en) * 1973-05-14 1975-10-07 Us Agriculture Azeotropic solvents for permanent press treatments of cotton and cotton blend fabrics
WO2007136384A1 (en) * 2006-05-19 2007-11-29 The Procter & Gamble Company Textile benefit compositions

Also Published As

Publication number Publication date
DE1719546B2 (de) 1975-01-16
BE729664A (es) 1969-08-18
CH235169D (es)
SE366784B (es) 1974-05-06
NL6904030A (es) 1969-09-18
DE1719546A1 (de) 1969-11-27
GB1221751A (en) 1971-02-10
AT301484B (de) 1972-09-11
FR2004050B1 (es) 1975-01-10
FR2004050A1 (fr) 1969-11-21
DE1719546C3 (de) 1975-08-28

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