US3027270A - Process for preventing quaternary nitrogen compound odors - Google Patents

Process for preventing quaternary nitrogen compound odors Download PDF

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US3027270A
US3027270A US817083A US81708359A US3027270A US 3027270 A US3027270 A US 3027270A US 817083 A US817083 A US 817083A US 81708359 A US81708359 A US 81708359A US 3027270 A US3027270 A US 3027270A
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odors
fabric
quaternary nitrogen
water
treated
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US817083A
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James F Cotton
Nevels Dora Alice
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West Point Manufacturing Co
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West Point Manufacturing Co
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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
    • D06M11/54—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur dioxide; with sulfurous acid or its salts
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating 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

Definitions

  • the present invention relates to certain novel improvements for avoiding or controlling the formation of undesirable odors normally encountered in fabrics or similar materials which have been treated with quaternary nitrogen compounds or the like for the purpose of imparting water repellency and/or other desired characteristics.
  • Textile fabrics, woven, knit or non-woven, are fre quently treated with quaternary nitrogen compounds such as long chain fatty pyridinium and picolinium salts and other alkyl or aryl amines and imines for a variety of purposes.
  • these compounds hereinafter referred to broadly as water repellents for convenience, are used to confer durable water repellency, spot resistance, softness, and the like, to textile fabrics.
  • Dimensional stability, crush and wear resistance, durability and appearance of textiles such as cotton, rayon, wool, nylon, and the like may also be improved by using these compounds in conjunction with various types of resins.
  • the principal object of the present invention is to provide a straightforward, inexpensive and highly effective method of controlling or eliminating undesirable pyridine, picoline or related odors in materials treated with water repellents of the type indicated heretofore and normally subject to such odors as a result of such treatment.
  • Other objects will also be apparent from the following detailed description of the invention.
  • the method of the present invention comprises impregnating filamentary or sheet material 3,627,270 Patented Mar. 27, 1962 treated with a quaternary nitrogen water repellent or the like and normally subject to odors as a result of such treatment, with an aqueous solution of a compound supplying the HSO ion.
  • any water-soluble organic and inorganic compound capable of forming HSO ions in aqueous solution may be used as the odor controlling agent of the invention.
  • Particularly desirable is sodium meta bisulfite (Na S O because of its availability and low cost.
  • other water soluble salts of sulfurous acid for example, the sulfites and bisulfites of the alkali metals of group I-A of the periodic table, i.e. lithium, sodium,'potassium, rubidium and cesium and of the alkaline earth metals of group ILA, such as beryllium, magnesium, and calcium, as well as those of zinc and aluminum.
  • Ammonium bisulfite, sulfurous acid per se or sulfur dioxide in solution SO +H O H SO may also be used.
  • the odor control agent may be applied to the material at any stage in the treatment of the material.
  • the agent may be applied simultaneously with the water repellent or at some later stage, such as after padding on the repellent or after the drying and/or curing of the same.
  • the amount of odor control agent to be used according to the invention can be widely varied, the optimum in any particular case depending upon other operating factors, such as the nature and amount of water repellent applied to the material, the degree of cure, whether the odor control agent is added simultaneously with or after the Water repellent compound, etc.
  • sufiicient odor control agent should be used to react with all free and potentially free pyridine and/or picoline or related odor-forming components.
  • Usually, or less (e.g. down to about 10%) of the agent by weight on the weight of the quaternary ammonium water repellent or like material may be utilized. If there is too great an excess of agent, the odor of sulfur dioxide may be detectable.
  • Any fibrous material normally subject to the formation of undesirable odors from pyridine, picoline, etc., when treated with water repellents of the type indicated, may be processed according to the invention described herein.
  • the invention is applicable to control odors occasioned by any of the durable water repellents: and softening compounds, particularly quaternary nitrogen compounds such as long chain fatty pyridinium and picolinium salts and other alkyl and aryl amides and imides.
  • Long chain fatty amide compounds capable of being methylolated and fixed to fibers or mixed with thermosetting resins and fixed to fibers may be used, principally for softening.
  • Typical water repellents contemplated for treatment herein include stearoxymethyl pyridinium chloride; stearamido methyl pyridinium chloride; stearoxyrnethyl picolinium chloride; and 1-(octadecyloxymethyl)pyridinium chloride.
  • Quaternary nitrogen compounds useful in imparting water repellency are also described in article entitled imparting Water-Repellency to Textiles by Chemical Methods, Textile Research Journal, 18, 396 (1948).
  • the odor control treatment described herein may take place simultaneously with the repellent and/or softening treatment, or subsequent thereto at any stage, including after curing of the repellent. It is desirable, but not required, to use a water wash after the odor control treatment to remove the surplus odor control agent and insure development of the maximum repellency.
  • Example I Bleached and dyed neturalized cotton poplin fabric was treated for durable water repellency by padding to pickup by weight stearamidomethyl pyridinium chloride with 3% sodium bisulfite and 0.50% sodium acetate. The thus treated fabric was then dried and cured for 3 minutes at 330 F. The fabric was then washed through a S-box serpentine washer at 130 F, followed by drying. The fabric was free from pyridine odors and water repellency was satisfactory. When the bisulfite was omitted, a definite pyridine odor was noticeable in the fabric.
  • Example 11 Bleached, dyed and neutralized cotton twill fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxyrnethyl pyridinium chloride with 3% sodium bisulfite and 0.50% sodium acetate. The thus treated fabric was then dried and cured for 5 minutes at 320 F. The fabric was then washed through a 5-box serpentine washer at 130 F., followed by drying. The fabric was free from pyridine odors, whereas such odors were markedly present in the absence of any bisulfite, and the AATCC spray rating was 100.
  • Example III Bleached, dyed and neutralized cotton fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxymethyl picolinium chloride with 3% sodium bisulfite and 0.25% sodium acetate. The thus treated fabric was then dried and cured for 2 minutes at 340 F. The fabric was then washed through a. S-box serpentine washer at 130 F., followed by drying. The
  • AATCC spray rating was increased from before washing to after washing and the fabric was free of picoline odors.
  • Example IV Bleached, dyed and neutralized cotton fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxymethyl pyridinium chloride with 0.50% sodium acetate. During passage of the fabric to the dryer, the fabric was sprayed evenly to pickup by weight 3% sodium bisulfite from a solution. The thus treated fabric was then dried and cured for 3 minutes at 330 F. The fabric was free of pyridine odors.
  • said repellent is selected from the group consisting of long chain fatty pyridinium and picolinium salts.

Description

United t itates Patent Q 3,027,276) PROCESS lFQR PREVENTING QUATERNARY NTTRGGEN CGMPQUND ODURS James F. Cotton, West Point, 8a., and Dora Alice Nevels, Shawrnut, Ala, assignors to West Point Manufacturing Company, West Point, 8a., a corporation of Georgia No Drawing. Filed dune 1, 195%, Ser. No. 817,083
7 Claims. (Cl. 111-62) The present invention relates to certain novel improvements for avoiding or controlling the formation of undesirable odors normally encountered in fabrics or similar materials which have been treated with quaternary nitrogen compounds or the like for the purpose of imparting water repellency and/or other desired characteristics.
Textile fabrics, woven, knit or non-woven, are fre quently treated with quaternary nitrogen compounds such as long chain fatty pyridinium and picolinium salts and other alkyl or aryl amines and imines for a variety of purposes. For example, these compounds, hereinafter referred to broadly as water repellents for convenience, are used to confer durable water repellency, spot resistance, softness, and the like, to textile fabrics. Dimensional stability, crush and wear resistance, durability and appearance of textiles such as cotton, rayon, wool, nylon, and the like may also be improved by using these compounds in conjunction with various types of resins.
Materials treated with quaternary nitrogen compounds and/or like water repellents have the disadvantage of containing offensive, disagreeable and/or toxic odor produced in the process of curing the water repellent material. These disagreeable odors frequently consist of pyridine, picoline, and/or other agents derived from the water repellent or incorporated therewith to confer water solubility to the compound for fabric impregnation before drying and curing. After curing, it is customary to extensively wash in alkaline and neutral baths to attempt to control disagreeable odors. The inability of these washes to control the disagreeable odors results in the production of fabrics presenting an unpleasant and potentially dangerous odor to the ultimate user of the fabrics as Well as people who, in the performance of their duties, are required to be in close association with the treated fabric. Such people are textile-finishing operators, warehousemen, and apparel fabricators. In places such as Warehouses, where large amounts of the repellent treated materials are stored, the accumulation of these offensive, disagreeable and toxic odors is so great as to require the use of gas masks in the enclosed area.
In the treatments of fabrics with the above described water repellents, there is often such a strong and voluminous evolution of offensive, disagreeable and/or toxic odors of pyridine and/or picoline or the like from the treating baths of which the water repellent material is a component, that the operators of the application machinery and the personnel required for preparation of the baths are frequently required to wear gas masks.
It will be appreciated from the foregoing that the prior art application of Water repellents, including quaternary nitrogen or the like, leave much to be desired in the Way of effective odor control, simplicity of operation, etc. Accordingly, the principal object of the present invention is to provide a straightforward, inexpensive and highly effective method of controlling or eliminating undesirable pyridine, picoline or related odors in materials treated with water repellents of the type indicated heretofore and normally subject to such odors as a result of such treatment. Other objects will also be apparent from the following detailed description of the invention.
Broadly stated, the method of the present invention comprises impregnating filamentary or sheet material 3,627,270 Patented Mar. 27, 1962 treated with a quaternary nitrogen water repellent or the like and normally subject to odors as a result of such treatment, with an aqueous solution of a compound supplying the HSO ion.
The control of odors in fabrics and similar materials treated with aldehyde resins, using a compound supplying the H30; ion to tie up free or potentially free odorforming formaldehyde, is described in U.S. Patent 2,870,- 041. The success of the present invention is based on the further surprising discovery that the H; ion may also be effectively used to control or prevent the completely different type of odors, e.g. picoline or pyridine odors, which normally result from the treatment of fabrics or other textiles with water repellents such as long chain picolinium or pyridinium salts, other quaternary nitrogen compounds and the like. The manner in which the HSO functions in the present case to achieve the desired odor control is not fully understood but, apparently the H80 ion reacts with the water repellent itself and/or the odor forming components thereof, to give a stable odorless product or products.
For the purposes described herein, any water-soluble organic and inorganic compound capable of forming HSO ions in aqueous solution may be used as the odor controlling agent of the invention. Particularly desirable is sodium meta bisulfite (Na S O because of its availability and low cost. However, there may also be used other water soluble salts of sulfurous acid, for example, the sulfites and bisulfites of the alkali metals of group I-A of the periodic table, i.e. lithium, sodium,'potassium, rubidium and cesium and of the alkaline earth metals of group ILA, such as beryllium, magnesium, and calcium, as well as those of zinc and aluminum. Ammonium bisulfite, sulfurous acid per se or sulfur dioxide in solution (SO +H O H SO may also be used.
The odor control agent may be applied to the material at any stage in the treatment of the material. For example, the agent may be applied simultaneously with the water repellent or at some later stage, such as after padding on the repellent or after the drying and/or curing of the same.
The amount of odor control agent to be used according to the invention can be widely varied, the optimum in any particular case depending upon other operating factors, such as the nature and amount of water repellent applied to the material, the degree of cure, whether the odor control agent is added simultaneously with or after the Water repellent compound, etc. Generally speaking, for durable water repellents, sufiicient odor control agent should be used to react with all free and potentially free pyridine and/or picoline or related odor-forming components. Usually, or less (e.g. down to about 10%) of the agent by weight on the weight of the quaternary ammonium water repellent or like material may be utilized. If there is too great an excess of agent, the odor of sulfur dioxide may be detectable.
Any fibrous material normally subject to the formation of undesirable odors from pyridine, picoline, etc., when treated with water repellents of the type indicated, may be processed according to the invention described herein. This includes textile materials such as fibers, yarns and fabric, whether woven, knit or non-woven, comprising natural or synthetic fibers, particularly cotton, wool, rayon, nylon, linen, etc.
The invention is applicable to control odors occasioned by any of the durable water repellents: and softening compounds, particularly quaternary nitrogen compounds such as long chain fatty pyridinium and picolinium salts and other alkyl and aryl amides and imides. Long chain fatty amide compounds capable of being methylolated and fixed to fibers or mixed with thermosetting resins and fixed to fibers may be used, principally for softening.
Typical water repellents contemplated for treatment herein include stearoxymethyl pyridinium chloride; stearamido methyl pyridinium chloride; stearoxyrnethyl picolinium chloride; and 1-(octadecyloxymethyl)pyridinium chloride. Quaternary nitrogen compounds useful in imparting water repellency are also described in article entitled imparting Water-Repellency to Textiles by Chemical Methods, Textile Research Journal, 18, 396 (1948).
As indicated heretofore, the odor control treatment described herein may take place simultaneously with the repellent and/or softening treatment, or subsequent thereto at any stage, including after curing of the repellent. It is desirable, but not required, to use a water wash after the odor control treatment to remove the surplus odor control agent and insure development of the maximum repellency.
The invention is further illustrated by the following examples:
Example I Bleached and dyed neturalized cotton poplin fabric was treated for durable water repellency by padding to pickup by weight stearamidomethyl pyridinium chloride with 3% sodium bisulfite and 0.50% sodium acetate. The thus treated fabric was then dried and cured for 3 minutes at 330 F. The fabric was then washed through a S-box serpentine washer at 130 F, followed by drying. The fabric was free from pyridine odors and water repellency was satisfactory. When the bisulfite was omitted, a definite pyridine odor was noticeable in the fabric.
Example 11 Bleached, dyed and neutralized cotton twill fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxyrnethyl pyridinium chloride with 3% sodium bisulfite and 0.50% sodium acetate. The thus treated fabric was then dried and cured for 5 minutes at 320 F. The fabric was then washed through a 5-box serpentine washer at 130 F., followed by drying. The fabric was free from pyridine odors, whereas such odors were markedly present in the absence of any bisulfite, and the AATCC spray rating was 100.
Example III Bleached, dyed and neutralized cotton fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxymethyl picolinium chloride with 3% sodium bisulfite and 0.25% sodium acetate. The thus treated fabric was then dried and cured for 2 minutes at 340 F. The fabric was then washed through a. S-box serpentine washer at 130 F., followed by drying. The
-3 AATCC spray rating was increased from before washing to after washing and the fabric was free of picoline odors.
Example IV Bleached, dyed and neutralized cotton fabric was treated for durable water repellency by padding to pickup by weight 5% stearoxymethyl pyridinium chloride with 0.50% sodium acetate. During passage of the fabric to the dryer, the fabric was sprayed evenly to pickup by weight 3% sodium bisulfite from a solution. The thus treated fabric was then dried and cured for 3 minutes at 330 F. The fabric was free of pyridine odors.
It will be appreciated that various modifications may be made in the invention described herein without deviating from the scope thereof as defined in the following claims.
We claim:
1. In a process for treating textile material with an aldehyde-free treating agent containing a quaternary nitrogen water repellent, the improvement whereby odors resulting from said treatment are obviated comprising impregnating said material with a compound supplying the H80 ion.
2. The process of claim 1 wherein said material is impregnated with said compound simultaneously with the application of the water repellent.
3. The process of claim 1 wherein said material is impregnated with said compound after application of the water repellent.
4. The process of claim 1 wherein said material is dried and cured.
5. The process of claim 1 wherein said compound is sodium bisulfite in aqueous solution.
6. The process of claim 1 wherein from 10% to 100% of said compound is used, based on the Weight of repellent.
7. The process of claim 1 wherein said repellent is selected from the group consisting of long chain fatty pyridinium and picolinium salts.
References Cited in the file of this patent UNITED STATES PATENTS 2,294,435 Wolf Sept. 1, 1942 2,870,041 Waddle Ian. 20, 1959 OTHER REFERENCES Howard: The Effect of Chlorine and Subsequent Treatment With Sodium Bisulfite Upon the Physical Properties of Cotton Fabrics Treated With Various Resins, Textile Research Journal, February 1956, vol. 26, page 125.

Claims (1)

1. IN A PROCESS FOR TREATING TEXTILE MATERIAL WITH AN ALDEHYDE-FREE TREATING AGENT CONTAINING A QUATERNARY NITROGEN WATER REPELLENT, THE IMPROVEMENT WHEREBY ODORS RESULTING FROM SAID TREATMENT ARE OBVIATED COMPRISING IMPREGNATING SAID MATERIAL WITH A COMPOUND SUPPLYING THE HSO3-ION.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3196036A (en) * 1960-08-08 1965-07-20 West Point Pepperell Inc Process for controlling undesirable aldehyde and amine odors in treated textile material
US3484271A (en) * 1965-06-25 1969-12-16 Riegel Paper Corp Two step in situ reaction for producing coated paper webs
US3958044A (en) * 1973-02-03 1976-05-18 Lion Yushi Kabushiki Kaisha Method for coating inorganic compounds in powdered form
US4244059A (en) * 1979-04-23 1981-01-13 The Procter & Gamble Company Nether garment for and method of controlling crotch odors
US20030219789A1 (en) * 1999-10-28 2003-11-27 Raitano Arthur B. 36P6D5: secreted tumor antigen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2294435A (en) * 1936-12-04 1942-09-01 Heberlein Patent Corp Process for rendering textiles water-repellent
US2870041A (en) * 1958-06-02 1959-01-20 West Point Mfg Co Process for preventing aldehyde odors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2294435A (en) * 1936-12-04 1942-09-01 Heberlein Patent Corp Process for rendering textiles water-repellent
US2870041A (en) * 1958-06-02 1959-01-20 West Point Mfg Co Process for preventing aldehyde odors

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3196036A (en) * 1960-08-08 1965-07-20 West Point Pepperell Inc Process for controlling undesirable aldehyde and amine odors in treated textile material
US3484271A (en) * 1965-06-25 1969-12-16 Riegel Paper Corp Two step in situ reaction for producing coated paper webs
US3958044A (en) * 1973-02-03 1976-05-18 Lion Yushi Kabushiki Kaisha Method for coating inorganic compounds in powdered form
US4244059A (en) * 1979-04-23 1981-01-13 The Procter & Gamble Company Nether garment for and method of controlling crotch odors
US20030219789A1 (en) * 1999-10-28 2003-11-27 Raitano Arthur B. 36P6D5: secreted tumor antigen

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