US3058848A - Anti-crease finishings and their manufacture - Google Patents

Anti-crease finishings and their manufacture Download PDF

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Publication number
US3058848A
US3058848A US3392460A US3058848A US 3058848 A US3058848 A US 3058848A US 3392460 A US3392460 A US 3392460A US 3058848 A US3058848 A US 3058848A
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United States
Prior art keywords
imidazolidone
dimethylol
fabric
crease
chlorine
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Gruber Gunter
Wannow Hans-Andreas
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CASSEILA FARBWERKE MAINKUR AG
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CASSEILA FARBWERKE MAINKUR AG
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    • 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
    • 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
    • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
    • Y10T442/277—Coated or impregnated cellulosic fiber fabric
    • Y10T442/2828—Coating or impregnation contains aldehyde or ketone condensation product
    • Y10T442/2852—Amide-aldehyde condensate [e.g., modified urea-aldehyde condensate, etc.]

Definitions

  • This invention relates to a process for finishing cellulose materials. More particularly it relates to an anticrease finishing which is resistant to chlorine by applying dimethylol-imidazolidone-2 together with ethers derived from dimethylol-imidazolidone-Z.
  • the present invention also relates to a novel composition of matter which is suitable for use in anti-crease finishing of cellulose fabrics.
  • dimethylol-imidazolidone-Z in the presence of suitable acid-forming agents imparts an excellent crease resistance to fabrics consisting of cellulose fibers, in particular to cotton.
  • finishes of dimethylol-imidazolidone-2 present a chlorine retaining power owing to the content of nitrogen, especially in those cases where, during the finishing of the fabrics, the condensation was carried out below 150.
  • the chlorine retaining power has detrimental effects in that the fabrics thus finished assume a yellow discoloration and lose their strength when subjected, after intense washing, to chlorine treatment and heating (ironing).
  • aminotriazine formaldehyde resins accordinging to US. patent specifications No. 2,690,404 and U.S. 2,833,674
  • polymeriza-ble vinyl or vinylidene compounds together with a compound copolymerizable therewith accordinging to US. patent specification No. 2,755,198
  • the finishings so obtained do no longer exhibit the soft feel and the high respiratory activity of the non-finished fabric which is due to the resinous nature of the additives as above mentioned.
  • the ratio between dimethylol-imidazolidone-2 and its ether may range from 9560% to 540%, whereby the impregnating liquors may contain 20 to 100 grams of the mixture per liter solution. Concentration and conditions of application may be controlled to provide 1 t0 7% pick-up of the impregnating agents on the weight of the fabric.
  • the ethers of the dimethylol-imidazolidone-2 which may be used under this invention are in particular those being soluble in water, such as the methyl-, propylo1 ethylene-glycol-ether.
  • the ethers of the dimethylolimidazolidone-2 containing unsaturated alcohols, such as 'allyl alcohol which are soluble in the impregnating baths exhibit a particularly favorable action.
  • Even ethers which contain higher alcohols, such as butyl alcohol, and are insoluble in the impregnating liquors may be employed.
  • the water-insoluble ethers have to be admixed, in form of an emulsion, to the solution containing the dimethylol-imidazolidone-2 during the impregnation of the fabric.
  • Example 1 A bleached and mercerized fabric consisting of a cotton poplin mixed fabric is impregnated on the padding machine with an aqueous solution of:
  • the pick-up of liquor is on the weight of the airdried fabric. Subsequently, the fabric is dried at temperatures of 6080 and afterheated at during 3 minutes.
  • the finished fabric cutting is boiled out at first in distilled water for 3 minutes and treated at 27 for 15 minutes in the wetted state with a sodium hypochlorite solution containing 0.25% active chlorine in the liquor ratio 1:50. Then the chlorinated sample is rinsed in fresh water for one minute at a temperature of 2l27, afterwards the excess water being squeezed by hand and this rinsing process being repeated 6 times. Subsequently, the sample is dried in the drying oven at 80 and suspended for 4 hours in an air-conditioned test room possessing a temperature of 20 and a relative dampness of 65%.
  • the finished sample is heated for 30 seconds with an ironing press, the metal plate of which is heated to To make comparisons as to the deterioration of the fiber during the heating process that is caused by the effects of the chlorine retaining power are effected as described above.
  • dially ether of the dimethylol-imidazolidone-2 utilized in the above example may be prepared as :follows:
  • Example 2 A cotton fabric treated with caustic soda and bleached is finished with an aqueous solution consisting of:
  • the bis-glycol-dimethylol-imidazolidone-2 which is used in the above example may be prepared in the following manner:
  • Rough yield 970 parts of a clear solution of about 50% bis-glycol-dimethylol-imidazolidone-2.
  • the raw material may be used straightly for the finish.
  • An article of manufacture comprising a cellulosic fabric containing from 1 to 7% of an anti-crease mixture of dimethylol-irnidazolidone-Z and an ether thereof whereby the ratio between dimethylol-imidazolidone-2 and its ether range from -60% to 5-40%.
  • a process of anti-crease finishing of cellulosic fabrics which comprises impregnating the fabric with impregnating liquors containing a mixture of dimethylolimidazolidone-Z and ethers thereof whereby the ratio between dimethylol-imidazolidone-2 and its ether ranges from 95-60% to 540% and the impregnating liquors contain 20 to 1 00 grams of the mixture per liter of solution, controlling the concentration and conditions of application to provide 1 to 7% pick-up of the impregnating agents on the weight of the fabric, and fixing the impregnating agents on the fabric by drying and heating the impregnated materials.

Description

United States Patent 3,i53,848 ANTi-CREASE AND THEE MANUFACTURE Giinter Gruber, Frankfurt am Main-Feehenheim, and Hans-Andreas Wannew, Frankfurt am Main, Germany, assignors to Casseiia Farhwerke Mainkur Aktiengesellschait, Frankfurt am Main-Feehenheim, Germany, a company of Germany No Drawing. Fiied .iune 6, 1960, Ser. No. 33,924 Ciairns priority, appiicatien Germany June 11, 1959 4 (Iiairns. (Cl. 117-13 .4)
This invention relates to a process for finishing cellulose materials. More particularly it relates to an anticrease finishing which is resistant to chlorine by applying dimethylol-imidazolidone-2 together with ethers derived from dimethylol-imidazolidone-Z. The present invention also relates to a novel composition of matter which is suitable for use in anti-crease finishing of cellulose fabrics.
It is known that dimethylol-imidazolidone-Z in the presence of suitable acid-forming agents imparts an excellent crease resistance to fabrics consisting of cellulose fibers, in particular to cotton. Further, it is known that finishes of dimethylol-imidazolidone-2 present a chlorine retaining power owing to the content of nitrogen, especially in those cases where, during the finishing of the fabrics, the condensation was carried out below 150. The chlorine retaining power has detrimental effects in that the fabrics thus finished assume a yellow discoloration and lose their strength when subjected, after intense washing, to chlorine treatment and heating (ironing).
Moreover, it is known from the US. patent specification 2,373,136 that ethers of the dimethylol-imidazolidone-2 may be also used for crease-proof finishing. The resultant effects, however, as regards the improvement of the crease resistance are so low that such processes have not become of practical interest.
Furthermore, it is known that aminotriazine formaldehyde resins (according to US. patent specifications No. 2,690,404 and U.S. 2,833,674) or polymeriza-ble vinyl or vinylidene compounds together with a compound copolymerizable therewith (according to US. patent specification No. 2,755,198) may be added to the impregnating liquors with a view to reducing the chlorine retaining power of fabrics finished with dimethylol-imidazolidone-Z. The finishings so obtained, however, do no longer exhibit the soft feel and the high respiratory activity of the non-finished fabric which is due to the resinous nature of the additives as above mentioned.
Now, we have found surprisingly that the detrimental efiects of the chlorine retaining power may be avoided in the case of anti-crease finishing of fabrics which are improved with dimethylol-imidazolidone-Z by impregnating the fabric with liquors containing a mixture of dimethylol-irnidazolidonefi and ethers thereof prepared from dimethylol-imidazolidone-2 with aliphatic alcohols, and finishing by drying and heating the impregnated material to fix the impregnating agents onto the fabric.
The ratio between dimethylol-imidazolidone-2 and its ether may range from 9560% to 540%, whereby the impregnating liquors may contain 20 to 100 grams of the mixture per liter solution. Concentration and conditions of application may be controlled to provide 1 t0 7% pick-up of the impregnating agents on the weight of the fabric.
It is an object of the invention to provide anti-crease finishings without any loss of strength of the treated fabric.
It is further object of this invention to provide anticrease finishings which do not exhibit any discoloration when subjected, after intense washing, to chlorine treatment and subsequent ironing.
ice
It is still a further object of this invention to obtain anti-crease finishings which retain the soft feel and respiratory activity of the non-treated fabric.
The ethers of the dimethylol-imidazolidone-2 which may be used under this invention are in particular those being soluble in water, such as the methyl-, propylo1 ethylene-glycol-ether. The ethers of the dimethylolimidazolidone-2 containing unsaturated alcohols, such as 'allyl alcohol which are soluble in the impregnating baths exhibit a particularly favorable action. Even ethers which contain higher alcohols, such as butyl alcohol, and are insoluble in the impregnating liquors may be employed. In this case the water-insoluble ethers have to be admixed, in form of an emulsion, to the solution containing the dimethylol-imidazolidone-2 during the impregnation of the fabric. I
The production of the ethers mentioned above is effected according to known methods.
The following examples of the method of the present invention are given as illustrative only, the parts being by weight and all temperatures in degrees centigrade, the invention, however, not being limited to the specific details of the examples:
Example 1 A bleached and mercerized fabric consisting of a cotton poplin mixed fabric is impregnated on the padding machine with an aqueous solution of:
45 grams/ liter dimethylol-imidazolidone-Z 15 grams/ liter diallyl-dimethylol-imidazolidone-2 15 grams/ liter crystallized magnesium chloride,
the pick-up of liquor is on the weight of the airdried fabric. Subsequently, the fabric is dried at temperatures of 6080 and afterheated at during 3 minutes.
Two groups of samples of the fabric thus finished were washed with 3 grams/liter Marseilles soap and 2 grams/ liter calcined soda at boiling temperature 3 or 10 times each for half an hour and subsequently subjected to chlorine stability test which is conducted as follows:
In connection with the Tentative Test Method 69-52, Damage Caused by Retained Chlorine, by the American Association of Textile Chemists and Colorists, the finished fabric cutting is boiled out at first in distilled water for 3 minutes and treated at 27 for 15 minutes in the wetted state with a sodium hypochlorite solution containing 0.25% active chlorine in the liquor ratio 1:50. Then the chlorinated sample is rinsed in fresh water for one minute at a temperature of 2l27, afterwards the excess water being squeezed by hand and this rinsing process being repeated 6 times. Subsequently, the sample is dried in the drying oven at 80 and suspended for 4 hours in an air-conditioned test room possessing a temperature of 20 and a relative dampness of 65%. At the end of this period the finished sample is heated for 30 seconds with an ironing press, the metal plate of which is heated to To make comparisons as to the deterioration of the fiber during the heating process that is caused by the effects of the chlorine retaining power are effected as described above.
The present test yielded the following result:
From the above table it becomes obvious that the tensile strength of the fabric finished with the mixture out of dimethylol-imidazolidone-Z together with the allylether of the dimethylol-imidazolidone-2 remained rather stable after chlorine treatment and subsequent heating, Whereas the fabric finished only with dimethylol-imidazolidone-2 had been considerably destroyed under the same procedure. The considerable deterioration of the fabric finished with dimethylol-imidazolidone-2 which was caused by the chlorine treatment during the heating and repeated washing process, may furthermore be observed in an intense browning of the material. In contrast thereto, the fabric finished with the mixture out of dimethylol-imidazolidone-Z and the allylether thereof, which had been subjected to the same test, remained entirely white.
The dially ether of the dimethylol-imidazolidone-2 utilized in the above example may be prepared as :follows:
258 parts imidazolidone-Z, 190 parts paraformaldehyde and 1000 parts \allyl alcohol are stirred in the presence of 1 part n caustic soda lye at 50-6'0. After approximately 20 minutes time the mixture is cooled down to room temperature and admixed in portions with 20 parts in total of concentrated hydrochloric acid while stirring. The temperature is held for 1 hour at 20-25. Then the solution is neutralized with caustic soda lye, the excess allyl alcohol distilled, sucked off from the resultant sodium chloride and the filtrate is distilled in the high vacuum. The diallyl-dimethylol-imidazolidone-2 has a boiling point of 145 2 mm.
Example 2 A cotton fabric treated with caustic soda and bleached is finished with an aqueous solution consisting of:
50 grams/liter dimethylol-imidazolidone-2 20 grams/liter bis-glycol-dimethylol-imidazolidone-2 grams/liter crystallized magnesium chloride further modification and,
an insignificant percentage in tensile strength after the treatment with chlorine and subsequent heating of the fabric which had "been washed repeatedly. Moreover, there was no discoloration to be observed, whereas a fabric finished in the same method only with dimethylolimidazolidone-Z gets brown and loses its stability almost entirely.
The bis-glycol-dimethylol-imidazolidone-2 which is used in the above example may be prepared in the following manner:
260 parts imidazolidone-Z and 190 parts paraformaldehyde are dissolved at 5060 in 500 parts glycol in the presence of 0.5 part 10 n caustic soda lye. The clear viscous solution is cooled as low as 20, admixed with 14 parts concentrated hydrochloric acid and agitated for 1 hour at 20-25. Subsequently, the solution is neutralized with 10 n caustic soda lye and sucked off from the common salt which might have precipitated.
Rough yield: 970 parts of a clear solution of about 50% bis-glycol-dimethylol-imidazolidone-2. The raw material may be used straightly for the finish.
It will be understood that this invention is capable to accordingly, it is desired t include such modifications within this invention as may fall within the scope of the appended claims.
We claim:
1. An article of manufacture comprising a cellulosic fabric containing from 1 to 7% of an anti-crease mixture of dimethylol-irnidazolidone-Z and an ether thereof whereby the ratio between dimethylol-imidazolidone-2 and its ether range from -60% to 5-40%.
2. A process of anti-crease finishing of cellulosic fabrics which comprises impregnating the fabric with impregnating liquors containing a mixture of dimethylolimidazolidone-Z and ethers thereof whereby the ratio between dimethylol-imidazolidone-2 and its ether ranges from 95-60% to 540% and the impregnating liquors contain 20 to 1 00 grams of the mixture per liter of solution, controlling the concentration and conditions of application to provide 1 to 7% pick-up of the impregnating agents on the weight of the fabric, and fixing the impregnating agents on the fabric by drying and heating the impregnated materials.
3. The process according to claim 2 wherein the impregnating liquor contains a mixture of dimethylolmidazOlidione-Z and the diallyl ether of dimethylolimidazolidone-Z with the ratio between dimethylolimidazolidone-Z and its ether ranges from 95-60% to 540%.
4. The process according to claim 2 wherein the impregnating liquor contains a mixture consisting of dimethylol-imidazolidone-Z and the diethylene-glycol ether of the dimethylol-imidazolidone-Z.
References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. AN ARTICLE OF MANUFACTURE COMPRISING A CELLULOSIC FABRIC CONTAINING FROM 1 TO 7% OF AN ANTI-CREASE MIXTURE OF DIMETHYLOL-IMIDAZOLIDONE-2 AND AN ETHER THEREOF WHEREBY THE RATIO BETWEEN DIMETHYLOL-IMIDAZOLIDONE-2 AND ITS ETHER RANGE FROM 95-60% TO 5-40%.
US3392460 1959-06-11 1960-06-06 Anti-crease finishings and their manufacture Expired - Lifetime US3058848A (en)

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DEC19186A DE1134655B (en) 1959-06-11 1959-06-11 Process for the production of a chlorine-resistant anti-crease finish
DEC24188A DE1148966B (en) 1959-06-11 1961-05-24 Process for anti-crease finishing on fabrics made from cellulose fibers

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US3058848A true US3058848A (en) 1962-10-16

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US19497062 Expired - Lifetime US3188232A (en) 1959-06-11 1962-05-15 Process for rendering cellulosic textile fabric crease resistant and the resulting article

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BE (2) BE618016A (en)
CH (2) CH384525A (en)
DE (2) DE1134655B (en)
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US3350221A (en) * 1964-02-06 1967-10-31 Kendall & Co Process for making filter-sheet material

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2373136A (en) * 1943-11-23 1945-04-10 Du Pont Ethylene urea derivatives
US2819179A (en) * 1954-01-18 1958-01-07 American Cyanamid Co Textile finishing process

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2734083A (en) * 1956-02-07 Preparation of n
NL82933C (en) * 1949-08-15
BE513352A (en) * 1951-08-18
US2755198A (en) * 1953-02-27 1956-07-17 Monsanto Chemicals Novel compositions and treatment of textile materials
US2690404A (en) * 1954-03-09 1954-09-28 Dan River Mills Inc Method of making wrinkle resistant fabric and composition therefor
US2810624A (en) * 1954-04-08 1957-10-22 Rohm & Haas Cellulose plisse fabric and method of producing by applying 1, 3-bis(hydroxy-methyl)-2-imidazolidone and chemical shrinking agent
US2833674A (en) * 1955-06-21 1958-05-06 Rohm & Haas Compositions for the treatment of textiles, the textiles obtained and processes for the treatment thereof
US2901463A (en) * 1955-06-21 1959-08-25 Rohm & Haas Compositions, textiles treated therewith and processes for the treatment thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2373136A (en) * 1943-11-23 1945-04-10 Du Pont Ethylene urea derivatives
US2819179A (en) * 1954-01-18 1958-01-07 American Cyanamid Co Textile finishing process

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US3188232A (en) 1965-06-08
NL121445C (en) 1900-01-01
NL278832A (en) 1900-01-01
CH384525A (en) 1962-05-30
NL125290C (en) 1900-01-01
DE1148966B (en) 1963-05-22
CH404601A (en) 1965-09-15
BE618016A (en) 1900-01-01
DE1134655B (en) 1962-08-16
BE591782A (en) 1900-01-01
NL252492A (en) 1900-01-01

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