US3105500A - Soil retaining finish for textiles - Google Patents
Soil retaining finish for textiles Download PDFInfo
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- US3105500A US3105500A US831489A US83148959A US3105500A US 3105500 A US3105500 A US 3105500A US 831489 A US831489 A US 831489A US 83148959 A US83148959 A US 83148959A US 3105500 A US3105500 A US 3105500A
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- cationic
- anionic
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
Definitions
- This invention relates to the treatment of fibrous and related materials. More particularly, it relates to a process for imparting a durable soil-attracting and soil-retaining finish to fibrous, shredded, cellular and related materials by treatment with a composition containing a long-chain anion active material and a long-chain cation active material.
- lt is an object of the present invention to provide a treatment for materials which will result in increased absorption of soil, more efiicient pick-up of soil and better soil retaining or holding ability than untreated materials.
- a further object of the present invention is to provide a process for imparting a durable soil-attracting and soilretaining finish to fibrous materials, particularly durable to washing or laundering.
- soil scavengers such as oils and waxes, are not durable to laundering.
- fibrous employed herein and throughout the present specification and claims is intended to include fibers or materials formed therefrom, whether they be of vegetable, animal or of synthetic origin or mixtures of two or more of such materials.
- vegetabie fibrous materials those of cotton, jute, hemp, ramie, linen and the like may be mentioned.
- Wool is illustrative of animal fibers, while synthetic fibers may be typified by nylon, viscose rayon, cellulose acetate, polyester fibers, available commercially as Dacron, and acrylic fibers, such as are available commercially as Creslan, Orlon and Acrilan, may be mentioned.
- fibrous as employed herein may apply to the fibers themselves or fabrics and articles formed therefrom. In the case of fabrics, they may be knitted,
- cellulosic materials and in particular those containing a substantial percentage of cotton, as, for example, at least 50%, and cellulose acetate have resulted in particularly good results.
- long-chain as applied herein in reference to anions and cations is intended to refer to aliphatic chains containing between 8 and 30 carbon atoms, and in the case of alkyl-aryl compounds of the benzene series betwen about 4 and 26 carbon atoms. Where the aryl group is naphthalene, the alkyl group may contain between 0 and about 22 carbon atoms. These or their equivalent materials may be employed. Essentially the materials suited for use in the preparation of the soil retaining finish are anion and cation active materials characterized by surface activity and capable of combining with one another, usually and preferably to form an insoluble precipitate in water.
- anion and cation active materials may be derived from anionic and cationic surface-active agents or surfactants. These materials are well known and have been described heretofore for various purposes, including wetting, penetrating, emulsifying, dispersing, solubilizing, foaming, frothing and washing or scouring in addition to other uses.
- the anionic active agents may be divided into the following major classes:
- anionic surface active agents which may be the source for the long-chain anions are the following:
- cationic-active agents may be divided into the following major classes:
- Dimethyl benzyl cetyl ammonium chloride Dimethyl 2-hydroxyethyl stearamidopropylammonium nitrate Dimethyl benzyl stearamidopropyl amonium chloride carboxyethyl ammonium It will be apparent that mixtures of two or more anionic-active agents and two or more cationic-active agents may be employed in accordance with the present invention.
- the anionic-and cationic-active agents are reacted in aqueous solution using essentially equimolar amounts of the reactants.
- the reaction product consisting of long-chain anionic and long-chain cationic portions is sufiiciently insoluble in water, it may be separated by physical means, as, for example, filtration.
- the product is too soluble in the aqueous medium for isolation by physical separation, as for example, filtration, it may be separated by extraction with a water-insoluble organic solvent in which the product is itself soluble. The organic solvent may then be evaporated to give the desired endproduct.
- the solution of the isolated product in a non-aqueous solvent such as alcohol or acetone, is applied to the fibrous material, which is then dried and/ or cured.
- a non-aqueous solution of essentially equimolecular amounts of the anionic-and cationicactive agent is supplied to the fibrous material, which is then dried and/ or cured.
- the soil-attracting and/or soilretaining finish is formed in situ on the fibrous material, the reaction between the materials being effected during the drying and removal of the solvent from the surface having been finished.
- the anionicand cationic-active agents are applied consecutively in non-aqueous solution to the fibrous material to be finished.
- the application may be in either order, it is believed more advantageous to apply the cationic agent first, since the cationic agent appears to have greater aflinity for the fibrous material, especially if it is of cellulosic nature.
- the first and second of the abovedescribed methods give approximately the same results and are preferred.
- the third is believed to be less satisfactory due to the leaching of the first component from the fibrous substrate by the solvent employed for the second component.
- Suitable non-aqueous solvents for use in applying the long-chain anionic-cationic products to the fibrous materials include ethanol, isoprapanol and acetone. However, other suitable alcohols, ketones, esters, ethers and the like may be employed.
- the composition of the present invention or the components thereof may be applied to suitable fibrous material by any of the conventional means, such as dipping, spraying, immersing, padding or the like.
- the soil-retaining property of the treated material is increased as the amount of the finishing composition of this invention increases on the material. Below a concentration of about 0.5% on the dry weight of the material there is relatively little improvement over the untreated material. In general, an application of at least 2% is recommended; however, the amount applied will depend on the nature of the material being treated. Also, the effectiveness of the treatment and its durability to washing is to some extent dependent upon the choice of anionic and cationic components. Thus, anionic and cationic components which result in the formation of a product having a low solubility in water so as to be capable of being characterized as being substantially waterinsoluble are more durable to washing than those having greater solubility in water.
- the material After application of the soil-retaining finish to a suitable fibrous substrate, the material is preferably dried, resulting in the evaporation of the solvent medium, and thereafter cured into intimate association with the fibrous substrate. Curing may be eifected at temperatures on the order of from between about 250 to about 350 for periods of time of from between about ten minutes to about five minutes, respectively. In general, curing of the finish on the substrate improves the soil-retaining ability of the finish and is greatly preferred. It should be noted that the above temperatures and times are merely illustrative with respect to curing conditions and that in general curing times and temperatures may be varied over wide limits to achieve good results.
- EXAMPLE 1 Dimethyl 2-H ydroxyethyl Stearamidopropyl Ammonium Bis( Tridecyl) -Sulf0succinate CHg-C O O C13Hz7 [(CH3)2(HOC2H4) (Ci- ⁇ H350 ONHCaHe) NP ICHF-C O O CraHzy S O a Solution A was prepared by dissolving 84 parts (0.153 mole) of sodium bis(tridecyl)-sulfosuccinate in 2,716 parts of water while stirring and heating to 67 C.
- Solution B was prepared by dissolving 73 parts (0.153 mole) of dimethyl 2-hydroxyethyl stearamidopropyl ammonium nitrate in 588 parts of water at 35 C. while stirring. Solution B was slowly added to solution A while the latter was cooled in an ice bath. At about 20 C. a white, Waxy precipitate was formed, which was separated by filtration and washed with water. The wax-like product was dried in vacuo at 65 C. to a solids content of about EXAMPLE 2 The product of Example 2 was prepared by a process similar to that of Example 1 with substitution of an equivalent amount of dimethyl-Z-hydroxyethyl stearamidopropyl ammonium phosphate for the nitrate used in Example 1.
- BOleic acid ester of sodium isethionate BOleic acid ester of sodium isethionate.
- Anionic agent D is usually identified as a cationic agent. However, it is believed that an exchange takes-place in the cationic portion thereof with the second cationic agent, to give a new and more durable (less soluble) salt.
- EXAMPLES 8-10 Ethanol solutions containing an anionic and a cationic surface active agent at a 1:1 molar ratio were prepared. The quantities used, on 100% real basis, are shown in Table II. Also shown are the strengths of the solutions in terms of percent organic salt on weight of solution.
- Example 4 Example 8 Example 1 Example 9 Example 6 Example 10 Example 7 1 One of the components in Example 5 was too insoluble in ethanol for it to be used in this method of preparation.
- Example 11 Example 5
- Example 12 Example 6
- Example 13 Example 7
- Example 14 TABLE III Anionic Agent Cationic Agent Total Solution
- Example N 0. Parts Strength, with percent 2 Name Parts Name Parts Water A 0. 58 E 0. 42 50 2. 0 B 0. 49 E 0. 51 50 2. 0 C 0. 46 F 0.55 50 2.0 D 0.51 F 0. 49 50 2.0
- EXAMPLE 15 An approximately 3% application of the product of Example 2 was made on viscose rayon carpet by padding with an approximately 3% solution of the product of Example 2 in ethanol (6 parts of product in 200 parts of ethanol) with a pick-up of based on the weight of the carpet. The carpet was dried.
- the washes referred to in Table IV were carried out at F. in a Laundromat Washing machine with neutral soap according to a standard procedure.
- Viscose carpet was treated with a 2% solution of the product of Example 1 in ethanol using a 100% pick-up on the weight of the carpet. The treated oanpet was dried for one hour at 225 F.
- the soiling test was carried out as described in Example 15.
- the treated carpet had a soiling index of 4.81.
- EXAMPLE 17 Cotton flannel cloth was treated with various amounts of the product of Example 1. The applications were made from solutions in alcohol with approximately a 100% pick-up on the weight of the fabric. All of the fabrics were dried for 30 minutes at 225 F., and some of the fabrics were cured for 6 minutes at 290 F., as indicated in Table V. Also, as indicated, some of the treated fabrics were Washed for 20 minutes in -a Laundromat washer with soap and 140 F. water. Portions of all the fabrics were then soiled by the standard procedure described in Example 15. The reflectance measurements of the fabrics before and after soiling were then determined and the soiling indices were calculated, as described in Example 15. The results are shown in Table V.
- EXAMPLE 18 Viscose carpet was treated with 1% solutions of the product of Example 1 in various solvents. The solutions were prepared in two ways: in Method A the dry product was dissolved in the solvent; in Method B a 50% stock solution in ethanol was diluted with the solvent chosen. The pick-up on the weight of the carpet was approximate- 1y 100%. The washing was done by the procedure of Example 15. The soiling index [was determined as described in Example 15. The results are shown in Table VI.
- Example 1 One percent applications of the products of Example 1 (in alcohol) and Example 3 (on solids basis) were applied to cotton flannel and the soiling test of Example was applied to the treated fabrics. The results are shown in Table VII.
- the examples serve to show that the products made by the procedures of Examples 1 and 3 give substantially the same results on cotton flannel.
- EXAMPLE 22 The alcoholic solutions of Examples 8-10 were applied to cotton flannel with a 100% pick-up on the weight of the fabric. The fabrics were dried and cured as in Example 20. The washings and soiling tests were carried out as in Example 20. The results are shown in Table X.
- Table X illustrates that applications of the soil-retaining finishing composition of this invention from alcoholic solutions is durable up to 5 launderings.
- EXAMPLE 23 The aqueous solutions of Examples 1114 were applied to cotton flannel with a 100% pick-up on the weight of the fabric. The treated fabrics were dried at 225 F., for 10 minutes and cured at 290 F. for 6 minutes. The washings were carried out in 100 F. water with soap and soda ash present. The fabrics were soiled by the procedure of Example 15. The results are shown in Table XI below.
- EXAMPLE 24 TABLE XII Product Washes Index 1 Anionic Agent: sodium bis (tridecyl)-sult'osuccinate. Cationic Agent: dimethyl 2-hydroxyethyl stearamidopropyl ammonium nitrate.
- This example serves to show that the anionic and cationic agents used in preparing the product of Example 1, when used separately, impart less soil-retaining properties to cotton flannel than the product of Example 1.
- EXAMPLE Applications of 1% and 2% solids of the products of Example 1 on the weight of the fabric were made to spun acetate from alcohol. Strips, 10.5 cm. x 4 cm. were taken, rolled into a tight pack, inserted in glass tubes and cigarettes attached. The cigarettes were smoked by means of a smoking apparatus consisting of a flask with a suction bulb and water as a metering liquid. Ten pufis of 35 m1. at -second intervals were made on each cigarette. Several cigarettes were smoked through the same filter, and the weight pick-up was taken at intervals after desiccating for 25 hours. This Weight was taken as a measure of the tars and/or solids picked up. In Table XIII, the tar and/ or solids pick-up of the treated acetate is compared with that of untreated acetate or untreated acetate padded through alcohol only.
- the present invention has Wide-spread utility.
- the present process may be employed for the treating of a number of articles or materials capable of being converted to a number of articles, wherein soil attraction and retention is highly desirable.
- suitable end-products fibrous doormats, dust cloths, dust mops, wiping cloths, wood-cellulose products, sponges, both natural and synthetic, are illustrative.
- compositions which are com patible with the essential components of the present composition may be employed therewith.
- disinfectants, perfumes, coloring agents, and the like may be employed in compositions insofar as they do not interfere with or impair significantly the soil-retaining and attracting properties of the finish.
- a process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent, as a soil retaining finish from about 2 to about 5% of an essentially equimolecular amount of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing said finish on said fibrous material.
- a process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent, from about 2 to about 5% of a composition containing essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing said component on said fibrous material to react the anionic and cationic components to form the soil retaining finish.
- a process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent solution, as a soil retaining finish from about 2 to about 5% of the water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing the said finish on said fibrous material.
- Fibrous material having as a durable soil retaining finish thereon from about 2 to about 5% of a water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cat-ionic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, said water insoluble reaction product having been applied from a non-aqueous solvent solution.
- Fibrous material according to claim 4 containing cellulose.
- Fibrous material according to claim 4 containing cellulose acetate.
- a soil retaining composition comprising at least 2% solids of a water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having 1 1 12 from about 13 to about 18 carbon atoms, and a non- 2,693,430 Cross et a1.
- Nov. 2, 1954 aqueous solvent therefor. 2,739,598 Eirich Mar. 27, 1956 2,746,928 Darragh et a1. May 22, 1956 References Cited in the file Of this patent 2,763,267 Muller Sept. 18, 1956 UNITED STATES PATENTS 5 2,789,223 Touey Feb. 5, 1 7
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Description
United States Patent 3,105,500 SOIL RETAINING FDIISH FOR TEXTILES Abraham Wilson, Millstone, William Julius van Loo, 3n,
Middlesex, and Frank M. Cowen, North Plainiield,
N.J., assignors to American Cyanamid Company, New
York, N.Y., a corporation of Maine No Drawing. Filed Aug. 4, 1959, Ser. No. 831,489
9 fllaims. '(Cl. 131208) This invention relates to the treatment of fibrous and related materials. More particularly, it relates to a process for imparting a durable soil-attracting and soil-retaining finish to fibrous, shredded, cellular and related materials by treatment with a composition containing a long-chain anion active material and a long-chain cation active material.
lt is an object of the present invention to provide a treatment for materials which will result in increased absorption of soil, more efiicient pick-up of soil and better soil retaining or holding ability than untreated materials.
It is a further object of the present invention to provide a process for treating filter materials to improve the removal of solids, liquids or gaseous materials from a fluid or gaseous medium.
A further object of the present invention is to provide a process for imparting a durable soil-attracting and soilretaining finish to fibrous materials, particularly durable to washing or laundering. Here it should be noted that known soil scavengers, such as oils and waxes, are not durable to laundering.
It is a still further object of the present invention to provide a composition which when applied to fibrous materials imparts soil-attracting and soil-retaining properties thereto which is comparatively easy to prepare and to employ.
Still further, it is an object of the present invention to provide various fibrous materials having a durable soilattracting and soil-retaining finish thereon and more specifically such materials as cigarette filters or filters normally employed in the manufacture of cigarettes.
These and other objects and advantages of the present invention will become more apparent from the detm'led description thereof set forth hereinbelow.
In accordance with the present invention we have found that these and other objects and advantages may be obtained by treating fibrous, shredded, cellular and related materials with a composition containing long-chain anions and long-chain cations.
The term fibrous employed herein and throughout the present specification and claims is intended to include fibers or materials formed therefrom, whether they be of vegetable, animal or of synthetic origin or mixtures of two or more of such materials. As illustrative of vegetabie fibrous materials, those of cotton, jute, hemp, ramie, linen and the like may be mentioned. Wool is illustrative of animal fibers, while synthetic fibers may be typified by nylon, viscose rayon, cellulose acetate, polyester fibers, available commercially as Dacron, and acrylic fibers, such as are available commercially as Creslan, Orlon and Acrilan, may be mentioned.
As indicated, fibrous as employed herein may apply to the fibers themselves or fabrics and articles formed therefrom. In the case of fabrics, they may be knitted,
were Patented Get. 1, 1953 woven, non-woven, felted or otherwise formed and may be suitable for a wide variety of end uses.
Of the possible fibrous materials contemplated, cellulosic materials, and in particular those containing a substantial percentage of cotton, as, for example, at least 50%, and cellulose acetate have resulted in particularly good results.
The term long-chain as applied herein in reference to anions and cations is intended to refer to aliphatic chains containing between 8 and 30 carbon atoms, and in the case of alkyl-aryl compounds of the benzene series betwen about 4 and 26 carbon atoms. Where the aryl group is naphthalene, the alkyl group may contain between 0 and about 22 carbon atoms. These or their equivalent materials may be employed. Essentially the materials suited for use in the preparation of the soil retaining finish are anion and cation active materials characterized by surface activity and capable of combining with one another, usually and preferably to form an insoluble precipitate in water.
The anion and cation active materials may be derived from anionic and cationic surface-active agents or surfactants. These materials are well known and have been described heretofore for various purposes, including wetting, penetrating, emulsifying, dispersing, solubilizing, foaming, frothing and washing or scouring in addition to other uses.
The anionic active agents may be divided into the following major classes:
Alkyl aryl sulfonates Alkyl sulfates Alkyl sulfonates Sulfated and sulfonated amides and amines Sulfated and sulfonated esters and ethers Among the many anionic surface active agents which may be the source for the long-chain anions are the following:
Sodium bis(tridecyl)-sulfosuccinate Sodium N-methyl-Nbleoyl taurate Oleic acid ester of sodium isethionate Sodium lauryl sulfate Disodium bis(sulfonaphthyl)-methane Sodium octylphenoxy polyglycol sulfonate Sodium alkylbenzenesulfonate Sodium isopropylnaphthalenesulfonate Sodium heptadecyl sulfate Polyoxyethylene sorbitan monostearate The cationic-active agents may be divided into the following major classes:
Salts of simple primary and tertiary amines Quaternary ammonium salts Salts and quaternary derivatives of amino acids Salts and quaternary derivatives of imidazolines Salts and quaternary derivatives of amino esters Among the many cationic surface-active agents which may be the source for the long-chain cations are the following:
Dimethyl benzyl cetyl ammonium chloride Dimethyl 2-hydroxyethyl stearamidopropylammonium nitrate Dimethyl benzyl stearamidopropyl amonium chloride carboxyethyl ammonium It will be apparent that mixtures of two or more anionic-active agents and two or more cationic-active agents may be employed in accordance with the present invention.
In one of the methods of treating fibrous materials in accordance with the present invention, the anionic-and cationic-active agents are reacted in aqueous solution using essentially equimolar amounts of the reactants. When the reaction product consisting of long-chain anionic and long-chain cationic portions is sufiiciently insoluble in water, it may be separated by physical means, as, for example, filtration. When the product is too soluble in the aqueous medium for isolation by physical separation, as for example, filtration, it may be separated by extraction with a water-insoluble organic solvent in which the product is itself soluble. The organic solvent may then be evaporated to give the desired endproduct. In either case, the solution of the isolated product in a non-aqueous solvent, such as alcohol or acetone, is applied to the fibrous material, which is then dried and/ or cured.
In a second method, a non-aqueous solution of essentially equimolecular amounts of the anionic-and cationicactive agent is supplied to the fibrous material, which is then dried and/ or cured. In accordance with this technique, it is believed that the soil-attracting and/or soilretaining finish is formed in situ on the fibrous material, the reaction between the materials being effected during the drying and removal of the solvent from the surface having been finished. I
In a third method, the anionicand cationic-active agents are applied consecutively in non-aqueous solution to the fibrous material to be finished. Although the application may be in either order, it is believed more advantageous to apply the cationic agent first, since the cationic agent appears to have greater aflinity for the fibrous material, especially if it is of cellulosic nature.
Generally speaking, the first and second of the abovedescribed methods give approximately the same results and are preferred. The third is believed to be less satisfactory due to the leaching of the first component from the fibrous substrate by the solvent employed for the second component.
While it is generally recommended that equimolecular amounts of anionic and cationic agents be employed in preparing the soil-retaining finishing material, slight excesses of either of the components are permissible. An excess of one over the other, however, is economically disadvantageous and, in general, should be avoided. Additionally, substantial excesses of one of the components over the other may result in the formation of a colloidal solution, preventing the isolation of the product by simple physical separation means, as, for example, filtration. In general, this difiiculty is overcome by employing equimolecular amounts of reactants and by reacting at a low temperature.
Suitable non-aqueous solvents for use in applying the long-chain anionic-cationic products to the fibrous materials include ethanol, isoprapanol and acetone. However, other suitable alcohols, ketones, esters, ethers and the like may be employed. The use of Water as the solvent where the product is sufficiently soluble in water in general produced less satisfactory results with respect to the durability of the finish to laundering. The composition of the present invention or the components thereof may be applied to suitable fibrous material by any of the conventional means, such as dipping, spraying, immersing, padding or the like.
In general, the soil-retaining property of the treated material is increased as the amount of the finishing composition of this invention increases on the material. Below a concentration of about 0.5% on the dry weight of the material there is relatively little improvement over the untreated material. In general, an application of at least 2% is recommended; however, the amount applied will depend on the nature of the material being treated. Also, the effectiveness of the treatment and its durability to washing is to some extent dependent upon the choice of anionic and cationic components. Thus, anionic and cationic components which result in the formation of a product having a low solubility in water so as to be capable of being characterized as being substantially waterinsoluble are more durable to washing than those having greater solubility in water.
After application of the soil-retaining finish to a suitable fibrous substrate, the material is preferably dried, resulting in the evaporation of the solvent medium, and thereafter cured into intimate association with the fibrous substrate. Curing may be eifected at temperatures on the order of from between about 250 to about 350 for periods of time of from between about ten minutes to about five minutes, respectively. In general, curing of the finish on the substrate improves the soil-retaining ability of the finish and is greatly preferred. It should be noted that the above temperatures and times are merely illustrative with respect to curing conditions and that in general curing times and temperatures may be varied over wide limits to achieve good results.
In order to illustrate the present invention, the following examples are given primarily by way of illustration. No details or enumerations contained therein should be construed as limitations on the present invention, except insofar as they appear in the appended claims. All parts and percentages are by weight, unless otherwise clearly indicated.
EXAMPLE 1 Dimethyl 2-H ydroxyethyl Stearamidopropyl Ammonium Bis( Tridecyl) -Sulf0succinate CHg-C O O C13Hz7 [(CH3)2(HOC2H4) (Ci-{H350 ONHCaHe) NP ICHF-C O O CraHzy S O a Solution A was prepared by dissolving 84 parts (0.153 mole) of sodium bis(tridecyl)-sulfosuccinate in 2,716 parts of water while stirring and heating to 67 C. Solution B was prepared by dissolving 73 parts (0.153 mole) of dimethyl 2-hydroxyethyl stearamidopropyl ammonium nitrate in 588 parts of water at 35 C. while stirring. Solution B was slowly added to solution A while the latter was cooled in an ice bath. At about 20 C. a white, Waxy precipitate was formed, which was separated by filtration and washed with water. The wax-like product was dried in vacuo at 65 C. to a solids content of about EXAMPLE 2 The product of Example 2 was prepared by a process similar to that of Example 1 with substitution of an equivalent amount of dimethyl-Z-hydroxyethyl stearamidopropyl ammonium phosphate for the nitrate used in Example 1.
EXAMPLE 3 50% of the product of Example 1 on the weight of the solution.
(When the above solution was diluted with water and the precipitate was filtered oil and dried, the product was similar to that of Example 1.)
EXAMPLES 4-7 Equimolecular amounts of anionic and cationic surface active agents in aqueous solutions were combined. The aqueous reaction mixture was extracted with ethyl acetate or methyl ethyl ketone, and the product was recovered by distilling off the solvent. The quantities used are shown in Table 1 below.
ASodium bis(tridecyl)-sulfosuccinate.
BOleic acid ester of sodium isethionate.
CSodium N-methylN-oleoyl taurate.
Dl\lixture of octadecylamine salt of octadecylcarbamic acid, and octadecylguanidine salt of octadecylcarbamic acid reacted with ethylene oxide.
EDimethyl benzyl cetyl ammonium chloride.
t tDimethyl 2-hydroxyethyl stearamidopropyl ammonium n1 ra e.
Anionic agent D is usually identified as a cationic agent. However, it is believed that an exchange takes-place in the cationic portion thereof with the second cationic agent, to give a new and more durable (less soluble) salt.
EXAMPLES 8-10 Ethanol solutions containing an anionic and a cationic surface active agent at a 1:1 molar ratio were prepared. The quantities used, on 100% real basis, are shown in Table II. Also shown are the strengths of the solutions in terms of percent organic salt on weight of solution.
These examples correspond in composition to those of Examples 4-7 (Table I) as follows:
Example 4 Example 8 Example 1 Example 9 Example 6 Example 10 Example 7 1 One of the components in Example 5 was too insoluble in ethanol for it to be used in this method of preparation.
TABLE II Anionic Agent Cationic Agent Total Solution Example No. Parts Strength,
with percent 2 Name 1 Parts Name Parts Ethanol A 0. 58 E 0. 42 50 2. 00 C 0. 28 F 0. 34 50 1. 24 D 0. 38 F 0. 32 50 1. 40
1 For identification see Table I. 2 Percent organic salt in solution.
EXAMPLES 11-14 Aqueous solutions or dispersions of equimolecular amounts of anionic and cationic agents were prepared. The quantities used, on 100% real basis, are shown in Table III.
These examples correspond in composition to those of Examples 4-7 (Table I) as follows:
Exampe 4 Example 11 Example 5 Example 12 Example 6 Example 13 Example 7 Example 14 TABLE III Anionic Agent Cationic Agent Total Solution Example N0. Parts Strength, with percent 2 Name Parts Name Parts Water A 0. 58 E 0. 42 50 2. 0 B 0. 49 E 0. 51 50 2. 0 C 0. 46 F 0.55 50 2.0 D 0.51 F 0. 49 50 2.0
1 For identification see Table I. Percent organic salt in solution.
EXAMPLE 15 An approximately 3% application of the product of Example 2 was made on viscose rayon carpet by padding with an approximately 3% solution of the product of Example 2 in ethanol (6 parts of product in 200 parts of ethanol) with a pick-up of based on the weight of the carpet. The carpet was dried.
The washes referred to in Table IV were carried out at F. in a Laundromat Washing machine with neutral soap according to a standard procedure.
The soiling test using a drum type laboratory soiler and a synthetic soil was carried out by the procedure described in the American Dyestulf Reporter 45, (1956). The results are shown in Table IV below.
Where Rs and RM are the fraction of light reflected from soiled and unsoiled test pieces, respectively. Thus, a soiling index of 1.0 or greater indicates that the treated fabric has an equal or greater afilnity for soil than the untreated fabric.
EXAMPLE 16 Viscose carpet was treated with a 2% solution of the product of Example 1 in ethanol using a 100% pick-up on the weight of the carpet. The treated oanpet was dried for one hour at 225 F.
The soiling test was carried out as described in Example 15. The treated carpet had a soiling index of 4.81.
EXAMPLE 17 Cotton flannel cloth was treated with various amounts of the product of Example 1. The applications were made from solutions in alcohol with approximately a 100% pick-up on the weight of the fabric. All of the fabrics were dried for 30 minutes at 225 F., and some of the fabrics were cured for 6 minutes at 290 F., as indicated in Table V. Also, as indicated, some of the treated fabrics were Washed for 20 minutes in -a Laundromat washer with soap and 140 F. water. Portions of all the fabrics were then soiled by the standard procedure described in Example 15. The reflectance measurements of the fabrics before and after soiling were then determined and the soiling indices were calculated, as described in Example 15. The results are shown in Table V.
TABLE V soiling Index Fabric Treatment, percent Washes None None None None None None The data in Table V indicates that the degree of soiling depends upon the concentration of the agent onthe fabric, the soiling scavenging efiect at concentrations of 0.5% or less being negligible. The initial scavenging efiect is improved by curing the dried fabric at 290 F. Applications of 2% or more of the agent are effective after five washes.
EXAMPLE 18 Viscose carpet was treated with 1% solutions of the product of Example 1 in various solvents. The solutions were prepared in two ways: in Method A the dry product was dissolved in the solvent; in Method B a 50% stock solution in ethanol was diluted with the solvent chosen. The pick-up on the weight of the carpet was approximate- 1y 100%. The washing was done by the procedure of Example 15. The soiling index [was determined as described in Example 15. The results are shown in Table VI.
One percent applications of the products of Example 1 (in alcohol) and Example 3 (on solids basis) were applied to cotton flannel and the soiling test of Example was applied to the treated fabrics. The results are shown in Table VII.
TABLE VII Comparison of Products Prepared by Two Mthods Product: Soiling Example 1.. 1. 76 Example 3 1.74
The examples serve to show that the products made by the procedures of Examples 1 and 3 give substantially the same results on cotton flannel.
EXAMPLE Cotton flannel was treated with 2% solutions of the products of Examples 4-7 in ethanol, using a 100% pick-up on the weight of the fabric. The treated fabrics were dried at 200 F. for 6 minutes and cured at 300 F. for 6 minutes. The washings were carried out in a Laundromat washer with soap and 140 F. water by the standard procedure. The fabrics were soiled by the standard procedure of Example 15. The results are shown in table VIII.
TABLE VIII Soiling Index Product Initial 1 Wash 3 Washes 1. 89 1. 65 2. 06 1. 7 5 1. 30 1. 1. 73 1 0. 97 1.15 Example 7-.. 1. 48 1. 46 l. 27
1 This product was not durable to laundering, although the czofresponding composition of Example 9 was durable (Table EXAMPLE 21 Cotton flannel was treated with 2% solutions or dispersions of the products of Examples 4-7 in water, using a 100% pick-up on the weight of the fabric. The treated fabrics were dried at 225 F. for 10 minutes and cured at 290 F. for 6 minutes. washings were carried out in 100 F. water with soap and soda ash present. The fabrics were soiled by the procedure of Example 15. The results are shown in Table 1X.
TABLE IX soiling Index Product Initial 1 Wash 3 Washes Example 4 2.34 1. 05 113 Example 5 2. 79 0. 97 1.05 Example 6 2.45 0. 01 098 Example 7 1.97 1.03 0.97
These examples serve to show that aqueous applications of the products of Examples 4-7 are not durable to laundering.
EXAMPLE 22 The alcoholic solutions of Examples 8-10 were applied to cotton flannel with a 100% pick-up on the weight of the fabric. The fabrics were dried and cured as in Example 20. The washings and soiling tests were carried out as in Example 20. The results are shown in Table X.
TABLE X Percent Soiling Index Product applicatiOn Initial 1 Wash 5Washes Example 8- 2.00 1. 65 1. 57 1. 69 Example 9- 1. 24 1. 61 1. 57 1. 40 Example 10 1. 40 1.80 1.44 1.39
Table X illustrates that applications of the soil-retaining finishing composition of this invention from alcoholic solutions is durable up to 5 launderings.
EXAMPLE 23 The aqueous solutions of Examples 1114 were applied to cotton flannel with a 100% pick-up on the weight of the fabric. The treated fabrics were dried at 225 F., for 10 minutes and cured at 290 F. for 6 minutes. The washings were carried out in 100 F. water with soap and soda ash present. The fabrics were soiled by the procedure of Example 15. The results are shown in Table XI below.
TABLE XI Soiling Index Product Initial 1 Wash 5 Washes Example 11 1. 75 1.13 1.05 Example 12 1. l0 1. 04 1. 05 Example l3 1. 65 0. 92 0. 80 Example 14 1. 77 1. 13 l. 00
These examples serve to show that applications of the non-isolated products of Examples 4-7 are not durable to laundering when applied from aqueous solution.
EXAMPLE 24 TABLE XII Product Washes Index 1 Anionic Agent: sodium bis (tridecyl)-sult'osuccinate. Cationic Agent: dimethyl 2-hydroxyethyl stearamidopropyl ammonium nitrate.
This example serves to show that the anionic and cationic agents used in preparing the product of Example 1, when used separately, impart less soil-retaining properties to cotton flannel than the product of Example 1.
EXAMPLE Applications of 1% and 2% solids of the products of Example 1 on the weight of the fabric were made to spun acetate from alcohol. Strips, 10.5 cm. x 4 cm. were taken, rolled into a tight pack, inserted in glass tubes and cigarettes attached. The cigarettes were smoked by means of a smoking apparatus consisting of a flask with a suction bulb and water as a metering liquid. Ten pufis of 35 m1. at -second intervals were made on each cigarette. Several cigarettes were smoked through the same filter, and the weight pick-up was taken at intervals after desiccating for 25 hours. This Weight was taken as a measure of the tars and/or solids picked up. In Table XIII, the tar and/ or solids pick-up of the treated acetate is compared with that of untreated acetate or untreated acetate padded through alcohol only.
As will be seen from the above examples and disclosure, the present invention has Wide-spread utility. Thus, the present process may be employed for the treating of a number of articles or materials capable of being converted to a number of articles, wherein soil attraction and retention is highly desirable. As examples of suitable end-products, fibrous doormats, dust cloths, dust mops, wiping cloths, wood-cellulose products, sponges, both natural and synthetic, are illustrative.
Further industrial and domestic applications include the use of the soil-retaining finish in elements in air conditioners and furnace filters to improve filtration properties and possibly effect the better removal of pollen and absorption of odors.
The utility in such specific applications as cigarette filters is clearly demonstrated in Table XIII, where it is shown that the 1% applications level absorption is substantially three times better than the untreated cellulose acetate.
It will be noted that other materials which are com patible with the essential components of the present composition may be employed therewith. Thus, for example, disinfectants, perfumes, coloring agents, and the like may be employed in compositions insofar as they do not interfere with or impair significantly the soil-retaining and attracting properties of the finish.
We claim:
1. A process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent, as a soil retaining finish from about 2 to about 5% of an essentially equimolecular amount of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing said finish on said fibrous material.
2. A process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent, from about 2 to about 5% of a composition containing essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing said component on said fibrous material to react the anionic and cationic components to form the soil retaining finish.
3. A process for imparting a durable soil retaining finish to fibrous materials which comprises applying thereto, from a non-aqueous solvent solution, as a soil retaining finish from about 2 to about 5% of the water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, and thereafter drying and curing the said finish on said fibrous material.
4. Fibrous material having as a durable soil retaining finish thereon from about 2 to about 5% of a water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cat-ionic surface active component, said anionic and cationic component having about 13 to about 18 carbon atoms, said water insoluble reaction product having been applied from a non-aqueous solvent solution.
5. Fibrous material according to claim 4 containing cellulose.
6. Fibrous material according to claim 4 containing cellulose acetate.
7. Fibrous material according to claim 4 in which the material is formed cotton fabric.
8. A cigarette filter impregnated with at least 0.5% of a water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having from about 13 to 18 carbon atoms, said reaction product having been applied to said cigarette filter material from a nonaqueous solvent solution.
9. A soil retaining composition comprising at least 2% solids of a water insoluble reaction product of essentially equimolecular amounts of a long chain anionic surface active component and a long chain cationic surface active component, said anionic and cationic component having 1 1 12 from about 13 to about 18 carbon atoms, and a non- 2,693,430 Cross et a1. Nov. 2, 1954 aqueous solvent therefor. 2,739,598 Eirich Mar. 27, 1956 2,746,928 Darragh et a1. May 22, 1956 References Cited in the file Of this patent 2,763,267 Muller Sept. 18, 1956 UNITED STATES PATENTS 5 2,789,223 Touey Feb. 5, 1 7
2,051,843 Gotte Aug. 25, 1936 FOREIGN PATENTS 2,482,816 Van Mater Sept. 27, 1949 501,402 Belgium Mar. 15, 1951
Claims (1)
1. A PROCESS FOR IMPARTING A DURABLE SOIL RETAINING FINISH TO FIBROUS MATERIALS WHICH COMPRISES APPLYING THERETO FROM A NON-AQUEOUS SOLVENT, AS A SOIL RETAINING FINISH FROM ABOUT 2 TO ABOUT 5% OF AN ESSENTIALLY EQUIMOLECULAR AMOUNT OF A LONG CHAIN ANIONIC SURFACE ACTIVE COMPONENT AND A LONG CHAIN CATIONIC SURFACE ACTIVE COMPONENT, SAID ANIONIC AND CATIONIC COMPONENT HAVING ABOUT 13 TO ABOUT 18 CARBON ATOMS, AND THEREAFTER DRYING AND CURING SAID FINISH ON SAID FIBROUS MATERIAL.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US831489A US3105500A (en) | 1959-08-04 | 1959-08-04 | Soil retaining finish for textiles |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US831489A US3105500A (en) | 1959-08-04 | 1959-08-04 | Soil retaining finish for textiles |
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Publication Number | Publication Date |
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US3105500A true US3105500A (en) | 1963-10-01 |
Family
ID=25259177
Family Applications (1)
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US831489A Expired - Lifetime US3105500A (en) | 1959-08-04 | 1959-08-04 | Soil retaining finish for textiles |
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US3334373A (en) * | 1965-04-07 | 1967-08-08 | American Cyanamid Co | Disposable fibrous dusting device |
US3481773A (en) * | 1965-08-02 | 1969-12-02 | Yardney International Corp | Process and composition for treating polyamide substance and resultant hydrophilic product |
US3622378A (en) * | 1968-08-09 | 1971-11-23 | Du Pont | Fibers with anionic-cationic finish |
US3645780A (en) * | 1966-08-08 | 1972-02-29 | Monsanto Co | Improving soil resistance through the use of rare earth metal containing compounds |
US3668133A (en) * | 1969-06-30 | 1972-06-06 | Hiroshima Kago Minamikanon Kk | Detergent oily agent adapted to be well adsorbed in fabrics and having detergency |
US4445521A (en) * | 1977-03-15 | 1984-05-01 | L'oreal | Composition and process for the treatment of keratin materials with polymers |
US4590955A (en) * | 1984-07-11 | 1986-05-27 | Olin Corporation | Cigarette paper with reduced CO on burning |
WO1999032002A1 (en) * | 1997-12-19 | 1999-07-01 | Sung Michael T | A method and apparatus for the selective removal of specific components from smoke condensates |
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US2051843A (en) * | 1933-05-15 | 1936-08-25 | American Hyalsol Corp | Method of producing a waterproof scroop on fiber materials |
US2482816A (en) * | 1943-06-08 | 1949-09-27 | Nat Lead Co | Method of waterproofing textiles with zirconyl compounds |
US2693430A (en) * | 1948-12-16 | 1954-11-02 | Gen Aniline & Film Corp | Process for rendering textile materials water-repellent |
US2739598A (en) * | 1953-05-04 | 1956-03-27 | R S Aries And Associates Inc | Filter for tobacco smoke |
US2746928A (en) * | 1952-06-26 | 1956-05-22 | California Research Corp | Germicidal detergent compositions |
US2763267A (en) * | 1951-11-27 | 1956-09-18 | Muller Paul Adolf | Smoke filter of fibrous material, especially for tobacco products |
US2780228A (en) * | 1954-03-03 | 1957-02-05 | Eastman Kodak Co | Filters for tobacco smoke comprising cellulose esters and ethers |
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US2051843A (en) * | 1933-05-15 | 1936-08-25 | American Hyalsol Corp | Method of producing a waterproof scroop on fiber materials |
US2482816A (en) * | 1943-06-08 | 1949-09-27 | Nat Lead Co | Method of waterproofing textiles with zirconyl compounds |
US2693430A (en) * | 1948-12-16 | 1954-11-02 | Gen Aniline & Film Corp | Process for rendering textile materials water-repellent |
BE501402A (en) * | 1950-02-21 | |||
US2763267A (en) * | 1951-11-27 | 1956-09-18 | Muller Paul Adolf | Smoke filter of fibrous material, especially for tobacco products |
US2746928A (en) * | 1952-06-26 | 1956-05-22 | California Research Corp | Germicidal detergent compositions |
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3334373A (en) * | 1965-04-07 | 1967-08-08 | American Cyanamid Co | Disposable fibrous dusting device |
US3481773A (en) * | 1965-08-02 | 1969-12-02 | Yardney International Corp | Process and composition for treating polyamide substance and resultant hydrophilic product |
US3645780A (en) * | 1966-08-08 | 1972-02-29 | Monsanto Co | Improving soil resistance through the use of rare earth metal containing compounds |
US3622378A (en) * | 1968-08-09 | 1971-11-23 | Du Pont | Fibers with anionic-cationic finish |
US3668133A (en) * | 1969-06-30 | 1972-06-06 | Hiroshima Kago Minamikanon Kk | Detergent oily agent adapted to be well adsorbed in fabrics and having detergency |
US4445521A (en) * | 1977-03-15 | 1984-05-01 | L'oreal | Composition and process for the treatment of keratin materials with polymers |
US4719099A (en) * | 1977-03-15 | 1988-01-12 | L'oreal | Composition and process for the treatment of keratin materials with polymers |
US4590955A (en) * | 1984-07-11 | 1986-05-27 | Olin Corporation | Cigarette paper with reduced CO on burning |
WO1999032002A1 (en) * | 1997-12-19 | 1999-07-01 | Sung Michael T | A method and apparatus for the selective removal of specific components from smoke condensates |
US6119699A (en) * | 1997-12-19 | 2000-09-19 | Sung; Michael T. | Method and apparatus for the selective removal of specific components from smoke condensates |
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