US3351483A - Method of softening textile fabrics - Google Patents
Method of softening textile fabrics Download PDFInfo
- Publication number
- US3351483A US3351483A US403939A US40393964A US3351483A US 3351483 A US3351483 A US 3351483A US 403939 A US403939 A US 403939A US 40393964 A US40393964 A US 40393964A US 3351483 A US3351483 A US 3351483A
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- Prior art keywords
- fabric
- solid
- detergent
- urea
- softener
- Prior art date
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Classifications
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
- C11D3/323—Amides; Substituted amides urea or derivatives thereof
Definitions
- This invention relates to compositions and methods for treating textile fabrics to clean the fabrics and to impart thereto desired feel characteristics.
- compositions useful for treating fabrics to improve the softness and feel characteristics thereof are known in the art.
- these softener compositions designated fabric softeners or textile softening agents, which are employed to treat fabrics, are liquids which contain as the principal active component a quaternary ammonium compound, that is, a substituted ammonium salt in which all four of the hydrogens of the ammonium radical are substituted by organic radicals.
- the liquid fabric softeners When used in domestic laundering, the liquid fabric softeners are added to the rinse water during the rinse cycle which is generally from about 3 to 5 minutes duration. This necessitates that the user monitor the laundering operation or take other recautions so that the liquid fabric softener is added at the proper time. In the case of housewives and other users, particularly in connection with automatic washing machines, the user generally must return to the washing machine either just prior to or during the rinse cycle of the washing operation which, to a busy user, is obviously burdensome.
- the user must take special precaution to employ the proper amount of liquid fabric softener in the rinse cycle of the washing operation and avoid large excesses thereof in order to prevent an overdosage which frequently renders the clothes water repellent with a greasy film remaining on the fabric surface as well as imparting a certain degree of yellowness to the fabrics.
- liquid fabric softeners cannot be combined with solid household laundry detergents in a single package but more important the conventional liquid softeners if added separately during the wash cycle do not fulfill their intended purpose and have no effect on the softness of the washed clothes.
- Laboratory tests indicate that the known liquid fabric softeners are, for all practical purposes, ineffective when used in the wash cycle together with or in the presence of household laundry detergents.
- Use directions on the labels of currently available fabric softeners caution that the products are to be used only in the rinse cycle, thus entailing all of the indicated disadvantages associated with the use of a fabric softener during the rinse cycle.
- household laundry detergent Over of the common household laundry detergents utilize synthetic surface active agents of the anionic and nonionic type.
- These household laundry detergent compositions generally include various builders such as alkali carbonates, silicates, phosphates and the like, but the synthetic surfactants are the principal active cleansing agents in the compositions.
- household laundry detergent means any composition useful for laundering fabrics which includes synthetic surface active agents of the anionic or nonionic type and various builders, which composition may or may not include other conventional ingredients such as optical brighteners, perfumes, antiredeposition agents and h. Soaps with or without builders are also included in the term household laundry detergent.
- the fabric softeners utilized in the present invention function effectively when employed during the wash cycle of the laundering operation in the presence of household laundry detergents.
- the use of the fabric softeners in the Wash cycle is highly advantageous from the standpoint of user convenience, and offers the significant and totally unexpected advantages that desired softness and feel characteristics are effectively imparted to the fabrics. Moreover, these desiderata are accomplished while at the same time the possibility of the fabrics receiving an overdosage of the fabric softener is effectively avoided.
- the fabric softeners can be added to a washload of textile fabrics in accordance with the present invention prior to or during the wash cycle of the laundering operation before addition of the household laundry detergent or simultaneously therewith, or during the washing cycle after addition of the detergent. It is also an object of the present invention to provide stable, solid, multipurpose fabric Washing and softening compositions comprising a household laundry detergent and a specified solid fabric softener whereby one addition of the composition to the wash cycle achieves both a cleaning and softening effect on the textile fabrics.
- the fabric softeners which are employed in the present invention are cation-active organic nitrogen compounds having textile softening properties and being capable of forming solid complexes or adducts with urea.
- These cation-active organic nitrogen compounds which can be used as active textile softening agents, are known to the art and comprise compounds such as quaternary ammonium compounds and amines containing at least one straight-chain organic radical of at least 8 carbon atoms and preferably from 12 to 22 carbon atoms.
- quaternary ammonium compounds having at least one straightchain organic radical containing between 12 and 22 carbon atoms
- primary, secondary and tertiary amine compounds having at least one straight-chain organic radical containing between 12 and 22 carbon atoms
- 1,3-propylene diamine compounds having a C to C straight-chain organic radical
- imidazoline compounds having a C to C straight-chain organic radical and like compounds.
- Specific preferred fabric softening compositions include such compounds as di-(hydrogenated tallow) dimethylammonium chloride, Z-heptadecyl-l, l-methyl [(2-stearoylamido)ethyl] imidazolinium methyl sulfate, di-(hydrogenated tallow) dimethylammonium methyl sulfate, primary tallow amine, primary hydrogenated tallow amine, tallow 1,3-propylene diamine, oleyl 1,3-propylene diamine and coco 1,3-propylene diamine, di-(soya) dimethylammonium chloride, and di-(coco) dimethylammonium chloride.
- Cationic nitrogen compounds having at least one organic radical of at least 8 carbon atoms, preferably from 12 to 22 carbon atoms, which themselves may range from liquids to semi-solid waxy masses, can be converted into free-flowing powders by reaction with urea as is known in the art. It is in the form of the urea complex that the cationic fabric softeners are employed in the methods and compositions of the present invention.
- the preparation of solid water-soluble urea adducts of quaternary ammonium compounds is disclosed in various prior art patents such as, for example, US. Patent 2,676,955 to Weitkamp et al., dated April 27, 1954; the disclosure thereof being hereby incorporated herein and made part of this application.
- a dry, free-flowing fabric softener comprising a urea inclusion compound of a softening agent is likewise disclosed in US. Patent 2,940,816 to Mitchell S. Sniegowski, dated June 14, 1960, and this type of material can be used in the present invention.
- the cationic nitrogen-containing component constitutes from about 4 to about 40 percent, preferably from about 18 to about 30 percent by Weight of the softener compositions utilized in the present invention.
- Urea which is reacted with the cationic nitrogen-containing compound to form an adduct constitutes the major component of the softener composition and is employed in amounts ranging from about 50 to about 90 percent by weight.
- the urea should be employed in an amount at least equal to that required for reaction with the cationic compound and preferably the urea is employed in theoretical excess of the cationic compound in a proportion ranging from about 2 to 180 moles of urea per mole of the cationic compound.
- the amount of Water present in the reaction mixture corresponds to from about 2 to about 15 percent, preferably about 3 to about 5 percent by weight of the composition.
- a solid reaction product is produced and flaked on a rolling mill or the like to a thickness not substantially in excess of 0.025 inch.
- a typical fabric softener composition suitable for use in accordance with the present invention is as follows, the parts being by weight:
- a solid fabric softener composition as exemplified above can be employed in the wash cycle of a laundering operation in the presence of conventional household laundry detergents.
- the anionic surface active agents employed in household laundry detergent compositions are the alkyl sulfates, alkyl aryl sulfonates such as alkyl benzene sulfonates, mono-glyceride sulfates, sulfoethyl oleates, sulfoethyl-N-methyl olcic amides, fatty acid soaps such as sodium stearate and the like.
- nonionic surfactants include polyglycol ether type surfactants; polyalkylene oxide derivatives of phenolic compounds such as dibutyl and diamyl phenols and cresols, heptyl, octyl, nonyl, decyl phenols and cresols; polyalkylene oxide derivatives of aliphatic organic hydroxy compounds and carboxy compounds; polyalkylene oxide derivatives of such mercapto compounds as dodecyl mercaptan, oleyl mercaptan, etc.; polyalkylene oxide derivatives of carboxylic acid amides and of sulfonamides.
- the fabric softener composition comprising the urea-cationic complex is employed in amounts sufficient to obtain satisfactory fabric softening.
- the specific amount to employ depends, of course, upon the amount of the active textile softening agent present.
- the fabric softener composition (cationic-urea complex) constitutes from about 10 to about 50 percent or more by weight of the fabric softenerdetergent composition. Minor amounts of secondary ingredients such as perfumes and dyes can also be employed in the compositions of the invention.
- Typical fabric softener-household laundry detergent compositions of the invention are as follows, the parts being by Weight:
- Organic surfactant 15-407 Sodium phosphate or polyphosphate 20-50 Sodium sulfate 5-60 Sodium silicate 0-8 Sodium carboxymethyl cellulose 0-1.5
- the specified solid fabric softeners can be added in accordance with this invention prior to or during the wash cycle of the laundering operation separately from the household laundry detergent and either before or after addition thereof or simultaneously therewith such as is the case when the fabric softenerhousehold laundry detergent compositions of the invention are employed.
- the fabric softener composition is employed in sufficient amounts to obtain a desired effect on the texture and feel of the fabrics treated therewith.
- the make-up of the compositions of this invention given heretofore is such to provide this amount of fabric softener when the laundry detergents are employed in usual amounts.
- Example I In one set of tests cup of a commercial laundry detergent sold under the trade name Tide by the Procter & Gamble Co. of Cincinnati, Ohio, was used in a General Electric top-loading automatic washing machine.
- Tide is a Well known commercially available household laundry detergent comprising sodium alkyl aryl sulfonate, sodium alkyl sulfate, sodium tripolyphosphate. Twenty grams of a solid flake fabric softener containing 4.8 grams (24%) of the active softener, a urea adduct of the quaternary ammonium compound, di(hydrogenated tallow) dimethylammonium chloride, were added to the wash cycle simultaneously with the detergent. The urea adduct of the quaternary ammonium compound was prepared in flake form by the method described in the above-mentioned Weiss patent applications.
- the wash load was composed of three Terry cloth bath towels and huck towel ballast to make a 6 lb. total load.
- the machine fill was set to the 6-10 lb. load fill (20.51-1 gal. of water).
- City tap Water having a hardness of about 136 ppm. (as calcium carbonate) was used in all washing and rinsing.
- Example 11 Using substantially the same procedure as in Example I, various cationic textile softening agents having at least one straight-chain organic radical of at least 8 or more carbon atoms complexed with urea were employed it as the active fabric softeners. These cationic softeners were complexed with urea as previously indicated and employed in the solid flake form. The number of panel members participating in each evaluation is indicated by the number below the slant bar. The number of panel members who selected the test fabric as softer or as having a better hand than the control (no fabric softener) is indicated by the number above the slant bar. The results are shown in Table I.
- Example III Utilizing substantially the same test procedure as in Example I and the same solid fabric softener, a number of washing operations were carried out with different household laundry detergents; detergent #1 being a commercially available low foaming anionic type household laundry detergent (sold under the trade name Dash by Procter & Gamble Co.
- detergent #2 a commercially available controlled foam nonionic type household laundry detergent (sold under the trade name All by Lever Brothers, Inc.). In both cases cup of detergent was used, which in the case of detergent #1 weighed 106 grams and detergent #2 Weighed 108 grams. Panel evaluations of duplicate washings are given in Table II.
- the amount of active liquid softener added to the wash cycle was controlled to provide substantially the same amount of active textile softening agent as in the solid softener (urea-di(hydrogenated tallow)dimethylarnmonium chloride).
- the solid softener was added to the dry clothes while the liquid softeners were necessarily added after introduction of wash water to avoid localized deposition.
- the liquid softeners used in the wash cycle were evaluated against the control (household laundry detergent alone) and the solid softener plus the same detergent (Tide). The results are indicated in Table III. TABLE III.SOLID SOFTENER-l-DETERGENT WASH- ING VS.
- Example V Laboratory tests on treated fabrics showed no decrease in water absorbency by the water drop method after 15 consecutive launderings of a 6-pound load with a household laundry detergent and 2 rounded tablespoons full (about 20 grams) of a solid fabric softener (urea complex).
- Example V1 Four solid fabric softener compositions were prepared by the preferred method previously described. Each of these compositions contained 22% of the active cationic fabric softener and 75% urea with the remainder being the minor ingredients shown in the typical composition illustrated heretofore. Using substantially the same procedure as in Example I, each of these products was employed in a wash-cycle softening test, the temperature of the wash water being 120 F.
- the active cationic material in each of these compositions was as follows:
- A Di(hydrogenated tallow) dimethyl ammonium chloride
- B Di-coco dimethyl ammonium chloride
- C Equal parts of di(hydrogenated tallow) dimethyl ammonium chloride and di-coco dimethyl ammonium chloride
- D Di-soy dimethyl ammonium chloride
- Each of the three terry-cloth towels from each of the test loads was then evaluated for softness by the following procedure:
- the three towels from the test using softener A were designated A-l, A-2 and A-3.
- the three from the test using softener B were designated B-l, B-2 and B-3, and so on with the other test towels, including the control.
- the test towels were then presented in pairs to a panel of six individuals who were asked to pick one of the pair as softer, an answer of no difference not being permitted. In no case was a panel member aware of the history of the specific towels he was judging.
- test towels were paired so that each treatment was compared three times by each panel member to each of the other treatments. That is, towel A-l was compared to B-l, C-l, D-1 and Control-l, A-2 was compared to 13-2, (3-2, D-2 and Control 2, and so on. Similarly, B-l was compared to C-l, D-1 and Control-l, and so on. Three towels per treatment, each compared to four other treatments, gives twelve comparisons. With six panel members, this gives a total of 72 panel comparisons for each treatment. The total number of times a towel representing a given treatment was chosen as softer, expressed as a percentage of the maximum possible choices (72), is an index of its relative softness. The results of this experiment are shown in Table IV.
- Example VII When fabrics are washed repeatedly using the same solid fabric softener in each wash cycle, the softness is enhanced compared to that attained in a single cycle.
- the data in Table V were obtained using the same procedure as in Example VI, except that the test wash loads were subjected to five consecutive washings using solid softeners containing 22% of the designated active cationic compounds before the test terry-cloth towels were evaluated for relative softness by the panel.
- Long-chain primary amines are effective softening ingredients in the solid fabric softener compositions of the invention.
- Compositions containing 22% of a long-chain primary amine with 75% urea were evaluated using the procedure of Example VI except that the terry-cloth towels were first cut in half and then distributed among the wash loads according to the following pattern:
- Example X Bosset of di-coco dimethyl ammonium chloride (2C) and amines Percent of maximum possible first choices (A) 30% 2C 52 (B) 20% 2C+10% lauryl amine (C) 20% 2C+10% H-tallow amine 45 (D) 20% 2C+10% arachidyl-behenyl amine 43 (E) 20% 2C+10% oleyl amine 58 (F) 20% 2C+10% tallow-l,3-propy1enediamine 50 (G) 20% 2C+10% stearlc ethanol ethylene diamide 52
- Example 1X Percent of Maximum Possible First Choices With Household Laundry Five 0 cles y Detergent 140 F. 120 F. F. 140 F. F. 90 F.
- househoud laundry detergent and fabric softener can be added at substantially the same time during the wash cycle thus eliminating the need of the user returning to the Washing operation during the rinse cycle;
- the solid fabric softener of the invention can be advantageously utilized with household laundry detergents; deposition of an excessive amount of textile softening agent on the fabrics is effectively avoided thereby obviating the possibility of the fabrics losing their desired water absorbency nating the deposition of greasy yellow colored films on the clothes;
- multi-purpose softening and cleaning compositions having formulations such as can be packaged together are provided thus affording conveniences to both the supplier and the user.
- the fabric softener compositions contemplated herein need not be employed in flake form but can be in powder or granular form, the principal requirement being that they be solid complexes with urea.
- liquid fabric softeners not complexed with urea do not afford satisfactory results when employed in the wash cycle of the laundering operation as opposed to the rinse cycle.
- the wash cycle can be considered as complete when the wash water containing the added household laundry detergent is drained from the wash tub, and the terms washing, wash cycle and washing operation should be so interpreted.
- a method of treating a textile fabric to clean and soften the fabric which comprises Washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition, said household laundry detergent being selected from the group consisting of anionic organic detergents and nonionic organic detergents and mixtures thereof with or without detergent builders, said solid fabric softener composition being present during the wash cycle and consisting essentially of a complex of urea with (1) a quaternary ammonium textile softening compound containing at least one straight-chain hydrocarbon radical of at least 8 carbon atoms or (2) an amine textile softening compound containing at least one straight-chain hydrocarbon radical of at least 8 carbon atoms.
- a method of treating a textile fabric to clean and soften the fabric which comprises washing said fabric with a household laundry detergent in the presence of a and elimifabric softening effective amount of a solid fabric softener composition, said household laundry detergent being selected from the group consisting of anionic organic detergents and nonionic organic detergent and mixtures thereof with or without detergent builders, said solid fabric softener composition being present during the wash cycle and consisting essentially of a complex of urea with (1) a quaternary ammonium textile softening compound containing at least one straight-chain hydrocarbon radical of from 12 to 22 carbon atoms or (2) an amine textile softening compound containing at least one straight-chain hydrocarbon radical of from 12 to 22 carbon atoms.
- a method of treating a textile fabric to clean and soften the fabric which comprises washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition which is present during the wash cycle and consisting essentially of a complex of urea with a quaternary ammonium compound containing at least one straightchain hydrocarbon radical of from 12 to 22 carbon atoms, said household laundry detergent being selected from the group consisting of anionic organic detergents and non ionic organic detergents and mixtures thereof with or without detergent builders.
- a method of treating a textile fabric to clean and soften the fabric which comprises washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition which is present during the wash cycle and consisting essentially of a complex of urea with an amine compound containing at least one straight-chain hydrocarbon radical of from 12 to 22 carbon atoms, said household laundry detergent being selected from the group consisting of anionic organic detergents and nonionic organic detergents and mixtures thereof with or without detergent builders.
- a method of treating a textile fabric to clean and soften the fabric which comprises washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition which is present during the wash cycle and consisting essentially of a complex of urea with di(hydrogenated tallow) dimethyl ammonium chloride, said household laundry detergent being selected from the group consisting of anionic organic detergents and nonionic or ganic detergents and mixtures thereof with or without detergent builders.
- a method of treating a textile fabric to clean and soften the fabric which comprises washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition which i present during the wash cycle and consisting essentially of a complex of urea with hydrogenated tallow amine, said household laundry detergent being se lected from the group consisting of anionic organic detergents and nonionic organic detergents and mixtures thereof with or without detergent builders.
- a method of treating a textile fabric to clean and soften the fabric which comprises Washing said fabric with a household laundry detergent in the presence of a fabric softening effective amount of a solid fabric softener composition which is present during the wash cycle and consisting essentially of a mixture of hydrogenated tallow amine and di(hydrogenated tallow) dimethyl ammonium chloride complexed with urea, said household laundry detergent being selected from the group consisting of anionic organic detergents and nonionic organic detergents and mixtures thereof with or without detergent builders.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1374263D CH1374263D (no) | 1963-02-14 | ||
GB1052847D GB1052847A (no) | 1963-02-14 | ||
FR952579A FR1384670A (fr) | 1963-02-14 | 1963-11-04 | Nouvel adoucissant et procédé pour le traitement des tissus |
DE19631444090 DE1444090A1 (de) | 1963-02-14 | 1963-11-05 | Zusammensetzungen und Verfahren zur Behandlung von Textilien |
CH1181667A CH490490A (de) | 1963-02-14 | 1963-11-08 | Textilwaschmittel mit weichmachenden Eigenschaften |
US403939A US3351483A (en) | 1963-02-14 | 1964-10-14 | Method of softening textile fabrics |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25864563A | 1963-02-14 | 1963-02-14 | |
US403939A US3351483A (en) | 1963-02-14 | 1964-10-14 | Method of softening textile fabrics |
Publications (1)
Publication Number | Publication Date |
---|---|
US3351483A true US3351483A (en) | 1967-11-07 |
Family
ID=26946774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US403939A Expired - Lifetime US3351483A (en) | 1963-02-14 | 1964-10-14 | Method of softening textile fabrics |
Country Status (5)
Country | Link |
---|---|
US (1) | US3351483A (no) |
CH (2) | CH490490A (no) |
DE (1) | DE1444090A1 (no) |
FR (1) | FR1384670A (no) |
GB (1) | GB1052847A (no) |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3454494A (en) * | 1965-08-03 | 1969-07-08 | Standard Chem Products Inc | Textile softener compositions |
US3498816A (en) * | 1967-08-29 | 1970-03-03 | Du Pont | Flock coating composition |
US3505221A (en) * | 1966-07-20 | 1970-04-07 | Armour Ind Chem Co | Fabric softener |
US3537993A (en) * | 1966-06-21 | 1970-11-03 | Procter & Gamble | Detergent compositions |
US3862905A (en) * | 1972-03-12 | 1975-01-28 | Henkel & Cie Gmbh | Washing agents containing an aminocarbonamide textile softener and process of washing and softening textiles |
US3891563A (en) * | 1972-09-11 | 1975-06-24 | Colgate Palmolive Co | Softergent composition containing n-alkyl-1,3-propylene diamine |
US4001123A (en) * | 1972-09-11 | 1977-01-04 | Colgate-Palmolive Company | Fabric softener compositions containing N-alkyl-1,3-propylene diamine treated with maleic anhydride |
US4057673A (en) * | 1974-10-09 | 1977-11-08 | Colgate Palmolive Company | Fabric conditioning with improved composition containing a plasticizer |
US4080162A (en) * | 1972-09-11 | 1978-03-21 | Colgate-Palmolive Company | Technical N-alkyl-1,3-propylene diamine and formulations containing same |
US4264457A (en) * | 1980-02-04 | 1981-04-28 | Desoto, Inc. | Cationic liquid laundry detergent and fabric softener |
US4327133A (en) * | 1977-11-21 | 1982-04-27 | Lever Brothers Company | Additives for clothes dryers |
EP0065387A1 (en) * | 1981-05-08 | 1982-11-24 | Unilever Plc | Fabric conditioning materials |
US4417995A (en) * | 1981-04-21 | 1983-11-29 | Lever Brothers Company | Fabric conditioning composition |
US4421792A (en) * | 1980-06-20 | 1983-12-20 | Lever Brothers Company | Additives for clothes dryers |
US4493773A (en) * | 1982-05-10 | 1985-01-15 | The Procter & Gamble Company | Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants |
US4627927A (en) * | 1982-07-05 | 1986-12-09 | Lion Corporation | Additive composition for granular detergent |
US4795032A (en) * | 1987-12-04 | 1989-01-03 | S. C. Johnson & Son, Inc. | Wash-added, rinse-activated fabric conditioner and package |
US4970008A (en) * | 1988-12-20 | 1990-11-13 | Kandathil Thomas V | Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines |
US5185088A (en) * | 1991-04-22 | 1993-02-09 | The Procter & Gamble Company | Granular fabric softener compositions which form aqueous emulsion concentrates |
EP0547723A1 (en) * | 1991-12-18 | 1993-06-23 | Colgate-Palmolive Company | Free-flowing powder fabric softening composition and process for its manufacture |
US5536421A (en) * | 1992-09-28 | 1996-07-16 | The Procter & Gamble Company | Method for using solid particulate fabric softener in automatic dosing dispenser |
US20020128671A1 (en) * | 1999-06-04 | 2002-09-12 | Scimed Life Systems, Inc. | Polymer covered vaso-occlusive devices and methods of producing such devices |
US7524318B2 (en) | 2004-10-28 | 2009-04-28 | Boston Scientific Scimed, Inc. | Ablation probe with flared electrodes |
US9150819B2 (en) | 2007-06-15 | 2015-10-06 | Ecolab Usa Inc. | Solid fabric conditioner composition and method of use |
US9506015B2 (en) | 2014-11-21 | 2016-11-29 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US9688945B2 (en) | 2014-11-21 | 2017-06-27 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US9725679B2 (en) | 2014-11-21 | 2017-08-08 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2021561C2 (de) * | 1969-05-02 | 1985-02-21 | Unilever N.V., Rotterdam | Verfahren zum Weichmachen von Textilien im Heißlufttextiltrockner und Mittel zu seiner Durchführung |
GB1514276A (en) * | 1975-10-22 | 1978-06-14 | Unilever Ltd | Fabric-softening compositions |
AU570738B2 (en) * | 1983-10-26 | 1988-03-24 | Unilever Plc | Detergent powder |
Citations (8)
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US2584056A (en) * | 1948-03-04 | 1952-01-29 | Olin Mathieson | Preparation of stable, solid, watersoluble, surface-active compositions containing urea and a quaternary ammonium compound |
US2634261A (en) * | 1948-01-09 | 1953-04-07 | Shell Dev | Urea complexes |
US2676955A (en) * | 1950-10-21 | 1954-04-27 | Standard Oil Co | Urea adducts of quaternary ammonium compounds |
US2734830A (en) * | 1950-01-13 | 1956-02-14 | ||
US2940816A (en) * | 1957-11-25 | 1960-06-14 | Corn Products Co | Fabric softener containing urea inclusion compound of hydrogenated tallow quaternary ammonium salt |
US3003954A (en) * | 1957-07-19 | 1961-10-10 | Staley Mfg Co A E | Methods and compositions of matter for softening textile fibers, yarns, and fabrics |
US3095373A (en) * | 1959-01-30 | 1963-06-25 | Wyandotte Chemicals Corp | Fabric softeners |
US3256180A (en) * | 1962-08-14 | 1966-06-14 | Little Inc A | Fabric softener compositions |
-
0
- GB GB1052847D patent/GB1052847A/en active Active
- CH CH1374263D patent/CH1374263D/xx unknown
-
1963
- 1963-11-04 FR FR952579A patent/FR1384670A/fr not_active Expired
- 1963-11-05 DE DE19631444090 patent/DE1444090A1/de active Pending
- 1963-11-08 CH CH1181667A patent/CH490490A/de not_active IP Right Cessation
-
1964
- 1964-10-14 US US403939A patent/US3351483A/en not_active Expired - Lifetime
Patent Citations (8)
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US2634261A (en) * | 1948-01-09 | 1953-04-07 | Shell Dev | Urea complexes |
US2584056A (en) * | 1948-03-04 | 1952-01-29 | Olin Mathieson | Preparation of stable, solid, watersoluble, surface-active compositions containing urea and a quaternary ammonium compound |
US2734830A (en) * | 1950-01-13 | 1956-02-14 | ||
US2676955A (en) * | 1950-10-21 | 1954-04-27 | Standard Oil Co | Urea adducts of quaternary ammonium compounds |
US3003954A (en) * | 1957-07-19 | 1961-10-10 | Staley Mfg Co A E | Methods and compositions of matter for softening textile fibers, yarns, and fabrics |
US2940816A (en) * | 1957-11-25 | 1960-06-14 | Corn Products Co | Fabric softener containing urea inclusion compound of hydrogenated tallow quaternary ammonium salt |
US3095373A (en) * | 1959-01-30 | 1963-06-25 | Wyandotte Chemicals Corp | Fabric softeners |
US3256180A (en) * | 1962-08-14 | 1966-06-14 | Little Inc A | Fabric softener compositions |
Cited By (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3454494A (en) * | 1965-08-03 | 1969-07-08 | Standard Chem Products Inc | Textile softener compositions |
US3537993A (en) * | 1966-06-21 | 1970-11-03 | Procter & Gamble | Detergent compositions |
US3505221A (en) * | 1966-07-20 | 1970-04-07 | Armour Ind Chem Co | Fabric softener |
US3498816A (en) * | 1967-08-29 | 1970-03-03 | Du Pont | Flock coating composition |
US3862905A (en) * | 1972-03-12 | 1975-01-28 | Henkel & Cie Gmbh | Washing agents containing an aminocarbonamide textile softener and process of washing and softening textiles |
US4080162A (en) * | 1972-09-11 | 1978-03-21 | Colgate-Palmolive Company | Technical N-alkyl-1,3-propylene diamine and formulations containing same |
US4001123A (en) * | 1972-09-11 | 1977-01-04 | Colgate-Palmolive Company | Fabric softener compositions containing N-alkyl-1,3-propylene diamine treated with maleic anhydride |
US3891563A (en) * | 1972-09-11 | 1975-06-24 | Colgate Palmolive Co | Softergent composition containing n-alkyl-1,3-propylene diamine |
US4057673A (en) * | 1974-10-09 | 1977-11-08 | Colgate Palmolive Company | Fabric conditioning with improved composition containing a plasticizer |
US4327133A (en) * | 1977-11-21 | 1982-04-27 | Lever Brothers Company | Additives for clothes dryers |
US4264457A (en) * | 1980-02-04 | 1981-04-28 | Desoto, Inc. | Cationic liquid laundry detergent and fabric softener |
US4421792A (en) * | 1980-06-20 | 1983-12-20 | Lever Brothers Company | Additives for clothes dryers |
US4417995A (en) * | 1981-04-21 | 1983-11-29 | Lever Brothers Company | Fabric conditioning composition |
EP0065387A1 (en) * | 1981-05-08 | 1982-11-24 | Unilever Plc | Fabric conditioning materials |
US4427558A (en) | 1981-05-08 | 1984-01-24 | Lever Brothers Company | Fabric conditioning materials |
US4493773A (en) * | 1982-05-10 | 1985-01-15 | The Procter & Gamble Company | Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants |
US4627927A (en) * | 1982-07-05 | 1986-12-09 | Lion Corporation | Additive composition for granular detergent |
US4795032A (en) * | 1987-12-04 | 1989-01-03 | S. C. Johnson & Son, Inc. | Wash-added, rinse-activated fabric conditioner and package |
US4970008A (en) * | 1988-12-20 | 1990-11-13 | Kandathil Thomas V | Fabric conditioner comprising a mixture of quaternary ammonium compounds and select tertiary amines |
US5185088A (en) * | 1991-04-22 | 1993-02-09 | The Procter & Gamble Company | Granular fabric softener compositions which form aqueous emulsion concentrates |
EP0547723A1 (en) * | 1991-12-18 | 1993-06-23 | Colgate-Palmolive Company | Free-flowing powder fabric softening composition and process for its manufacture |
US5259964A (en) * | 1991-12-18 | 1993-11-09 | Colgate-Palmolive Co. | Free-flowing powder fabric softening composition and process for its manufacture |
GR1001506B (el) * | 1991-12-18 | 1994-02-28 | Colgate Palmolive Co | Μαλακτική σύν?εση υφάσματος σε ελευ?έρως ρέουσα σκόνη & μέ?οδος βιομηχανικής κατασκευής αυτής. |
US5536421A (en) * | 1992-09-28 | 1996-07-16 | The Procter & Gamble Company | Method for using solid particulate fabric softener in automatic dosing dispenser |
US5792219A (en) * | 1992-09-28 | 1998-08-11 | The Procter & Gamble Company | Method for using solid particulate fabric softener in automatic dosing dispenser |
US20020128671A1 (en) * | 1999-06-04 | 2002-09-12 | Scimed Life Systems, Inc. | Polymer covered vaso-occlusive devices and methods of producing such devices |
US7524318B2 (en) | 2004-10-28 | 2009-04-28 | Boston Scientific Scimed, Inc. | Ablation probe with flared electrodes |
US9150819B2 (en) | 2007-06-15 | 2015-10-06 | Ecolab Usa Inc. | Solid fabric conditioner composition and method of use |
US9506015B2 (en) | 2014-11-21 | 2016-11-29 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US9688945B2 (en) | 2014-11-21 | 2017-06-27 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US9725679B2 (en) | 2014-11-21 | 2017-08-08 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US10415003B2 (en) | 2014-11-21 | 2019-09-17 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US10947481B2 (en) | 2014-11-21 | 2021-03-16 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
US11466233B2 (en) | 2014-11-21 | 2022-10-11 | Ecolab Usa Inc. | Compositions to boost fabric softener performance |
Also Published As
Publication number | Publication date |
---|---|
CH1374263D (no) | |
CH1181667A4 (no) | 1970-06-30 |
FR1384670A (fr) | 1965-01-08 |
GB1052847A (no) | |
DE1444090A1 (de) | 1968-10-24 |
CH490490A (de) | 1970-06-30 |
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