US3211646A - Composition for reducing readiness with which synthetic fibers accept an electric charge - Google Patents
Composition for reducing readiness with which synthetic fibers accept an electric charge Download PDFInfo
- Publication number
- US3211646A US3211646A US233145A US23314562A US3211646A US 3211646 A US3211646 A US 3211646A US 233145 A US233145 A US 233145A US 23314562 A US23314562 A US 23314562A US 3211646 A US3211646 A US 3211646A
- Authority
- US
- United States
- Prior art keywords
- formula
- carbon atoms
- base
- readiness
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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
- D06M13/405—Acylated polyalkylene polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/46—Textile oils
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
- Y10S260/19—Non-high polymeric antistatic agents/n
- Y10S260/20—Antistatic agent contains pentavalent nitrogen
Definitions
- hydrophobic fibers for example semisynthetic fibers from cellulose esters such as cellulose diacetate or cellulose triacetate, from polyesters such as polyterephthalic acid glycol ester, from polyamides, polyurethanes or polyacrylonitrile.
- the preparations of the invention contain on one hand the salts of the composition defined above under (a) and on the other hand the bases of the Formula 2 mentioned under (b).
- the salts themselves are composed of organic monocarboxylic acids and of bases of the Formula 1.
- These bases are as such known; they contain an ethylenediamine (CH CH or preferably a propylenediamine radical (-CH CH CH and as the linear aliphatic hydrocarbon radical R with 11 to 17 carbon atoms, for example, a radical of one of the formulae 12,
- the radicals RCO need not be uniform, and the diamines may very Well be acylated with different saturated and/ or unsaturated fatty acid radicals.
- the acyl radical RCO may be, inter alia, the radical of the so-called commercial stearic acid, a product consisting predominantly of stearic acid and containing further higher fatty acids, more especially palmitic acid and a small proportion of oleic acid and having a mean molecular weight of about 270.
- saturated radicals R it is of advantage to the solubility of these products to add a certain proportion of these compounds in which radical R is unsaturated.
- R and R present in the compounds of the Formula 1 are alkyls with 1 to 2 carbon atoms, that is to say methyl or ethyl groups. R and R may be identical or different from each other.
- acids for the manufacture of the salts referred to under (a) there are suitable, for example, aliphatic monocarboxylic acids with up to 5 carbon atoms, such as propionic acid, or more especially acetic or formic acid.
- the bases of the Formula 2 to be added to the salts from monocarboxylic acids and bases of the Formula 1, must contain as the linear aliphatic hydrocarbon radical R a radical with at least one double bond, and also in this case the residue of the composition (that is the radical of oleic acid) is preferred.
- the base contains an unsaturated radical R it is even possible to react an amount of the base in excess of 2 molecular proportions with 1 molecular proportion of halogencarboxylic acid to form directly a mixture, suitable for making the preparations, of 1 molecular proportion of salt and the excess of the base that has not been consumed in the quaternation and neutralization.
- the mineral oil solutions preferably contain from to 30% of the salt-base-mixture and from 85 to 70% of mineral oil;
- a so-called antistatic agent that is to say a substance capable of reducing the electrostatic charge
- electrically charged fibers tend to stick, for example to machine parts, or to repel one another in spinning.
- the fibers must be rendered soft and capable of sliding easily to ensure that the final yarn is pliable, and easy to spin and weave.
- the lubricating and softening agent used for this purpose is very frequently a mineral oil. Since the mixtures of the kind defined above are readily soluble in mineral oils, it is easy to achieve with such solutions readily and advantageously both effects simultaneously, namely a reduction of the electrostatic charge and the softening and lubricating.
- the viscosity of the mineral oils which is of importance to their suitabilityas lubricants, is at most affected to a minor and wholly acceptable degree.
- the preparations can therefore be applied to the fibers in the usual manner, exactly as is practized with mineral oil alone.
- the mineral oil is easy to remove the final product by rinsing with water.
- Example 1 36.5 parts of oleic acid dimethylaminopropylamide of (1 mol) are, mixed with 6 parts of acetic acid (1 mol) while being cooled. The resulting acetate is liquid and readily soluble in water.
- threads from polyamides there may be used threads from cellulose acetate or polyesters or filaments from polyacrylonitrile to which similar, good antistatic properties are thus imparted.
- Example 2 73 parts of oleic acid' dimethylaminopropylamide (2 mols) are heated to 55 to 60 C. in a reaction vessel equipped with an agitator. In the course of 30 minutes 9.4 parts of chloracetic acid (1 mol) are added, the air is then displaced by nitrogen and the mixture is heated on for 4 hours a1: 55 to 60 C. The resulting tough paste gives in water a clear solution of neutral reaction.
- Example 3 71.8 parts (1 mol) of commercial stearic acid dimethylaminopropylamide of the formula RCHN-OHz-CH2CH:N
- Example 4 91.2 parts of lauric acid dimethylaminopropylamide (2 mols) are heated to 55 to 60 C. in a reaction vessel equipped with an agitator. In the course of 30 minutes 14.1 parts of chloracetic acid (1 mol) are added, the air is displaced with nitrogen and the batch is heated on for 4 hours at 55 to 60 C., whereupon a tough paste is obtained. The preparation gives a clear solution in water and the solution is of neutral reaction. 3 parts of this mixture are mixed with heating with 4 parts of the acetate of oleic acid dimethylaminopropylamide (see Example 1) and 3 parts of oleic acid dimethylaminopropylamide, and the resulting mixture is dissolved as described in Example 1. A clear solution is obtained, without the viscosity of the oil being appreciably increased. 7 When the solution is poured into water, a fine emulsion results.
- Example 5 (1 mol) are mixed with 6 parts of glacial acetic acid (1 mol) and 9 parts of the acetate so obtained are mixed with 1 part of the oleic acid diethylaminoethylamide. 1 part of the resulting mixture is dissolved in 4 parts. of mineral oil, for example Mentor 2.8.
- the preparation is in the form of a clear solution of low viscosity and immediately forms an emulsion when poured into water.- Threads or filaments treated with this preparation 1305-- sess an antistatic finish.
- R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms
- R and R each represents an alkyl radical containing at most 2 carbon atoms and m is a whole number of at the most 2
- the ratio of base (b) to salt (a) being at least 1:10 and at most 20:10
- a mineral oil which is present in an amount of 70 to 85 percent, calculated on the total of the ingredients )+(c)- 2.
- a composition for reducing the readiness with which synthetic fibers accept an electrostatic charge consisting essentially of (a) an aliphatic monocarboxylic acid salt of an aliphatic monocarboxylic acid containing up to 5 carbon atoms and of a base of the formula in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms, R and R each represents an alkyl radical containing at most 2 carbon atoms and m is a whole number of at the most 2; (b) abase of the formula Ra R-CHN-CH2(CH2)m N in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms and at least one double bond, R and R each represent an alkyl radical containing at most 2 carbon atoms and m" is a whole number of at the most 2; the ratio of base (b) to salt (a) being at least 1:10 and at most 20:10; and (c) a mineral oil which is present in an amount of 70 to 85 percent, calculated
- a composition for reducing the readiness with which synthetic fibers accept an electrostatic charge consisting essentially of (a) a monocarboxylic acid salt of (1) a monocarboxylic acid of the formula in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms, R and R each represent an alkyl radical containing at most 2 carbon atoms, X represents a halogen atom and m is a whole number of at the most 2, and of (2) a base of the formula in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms, R and R each 6 represents an alkyl radical containing at most 2 carbon atoms and m is a whole number of at the most 2; (b) a base of the formula in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms and at least one double bond, R and R each represents an alkyl radical containing at most 2 carbon atoms and m' is a whole number of at the most 2;
- a composition for reducing the readiness with which synthetic fibers accept an electrostatic charge consisting essentially of (a) a monocarboxylic acid salt of an aliphatic monocarboxylic acid containing up to 5 carbon atoms and of a base of the formula in which R represents a linear aliphatic hydrocarbon radical containing 11 to 17 carbon atoms, R and R each represents an alkyl radical containing at most 2 carbon atoms and m is a whole number of at the most 2; (b) a base of the formula in which R and R each represents an alkyl radical containing at most 2 carbon atoms and m is a whole number of at most 2; the ratio of base (b) to salt (a) being at least 1:10 and at most 20:10; and (c) a mineral oil which is present in an amount of 70 to 85 perecent, calculated on the total of the ingredients (a)+(b)+(c).
- a composition for reducing the readiness with 7 which synthetic fibers accept an electrostatic charge consisting essentially of (a) the acetate of the base of the formula CH3 CH3 CHz-CH OH -N o1 CHI-c o 011 and of the base of the formula 9 I 7 CH3 H O-(CH -0H:CH-(OHzh-fi-HN-OEh-CHrOHz-N (b) the base of the formula given under (a); the ratio of base (b) to salt (a) being at least 1:10 and at most 20:10; and (c) a mineral oil which is present in an amount of 70 to 85 percent, calculated on the total of the ingredients (a)+(b)+(c).
- composition for reducing the readiness with which synthetic fibers accept an electrostatic charge consisting 8 essentially of (a) the acetate of the base of the formula Hac-(OH2) fiHN0H,oHr-0H,N
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1284261 | 1961-11-06 | ||
CH24762 | 1962-01-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3211646A true US3211646A (en) | 1965-10-12 |
Family
ID=25684015
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US233145A Expired - Lifetime US3211646A (en) | 1961-11-06 | 1962-10-25 | Composition for reducing readiness with which synthetic fibers accept an electric charge |
US233150A Expired - Lifetime US3174985A (en) | 1961-11-06 | 1962-10-25 | Amine salt of a quaternary ammoniumcontaining acid |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US233150A Expired - Lifetime US3174985A (en) | 1961-11-06 | 1962-10-25 | Amine salt of a quaternary ammoniumcontaining acid |
Country Status (6)
Country | Link |
---|---|
US (2) | US3211646A (fr) |
AT (1) | AT238130B (fr) |
BE (1) | BE624404A (fr) |
CH (1) | CH414935A (fr) |
DE (1) | DE1419420C3 (fr) |
GB (2) | GB966822A (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3548036A (en) * | 1962-11-02 | 1970-12-15 | Basf Ag | Polymonoolefins containing an amine antistatic additive dispersed therein |
US4264516A (en) * | 1977-08-01 | 1981-04-28 | Ciba-Geigy Corporation | Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof |
EP0292481A1 (fr) * | 1986-10-23 | 1988-11-30 | Frank H Stevens | Composition particulaire emulsifiable pour lotion capillaire. |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3914496A (en) * | 1974-03-01 | 1975-10-21 | Basf Ag | Antistatic finishing of surfaces |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
US2717842A (en) * | 1952-09-10 | 1955-09-13 | American Cyanamid Co | Antistatic treatment and treated products |
US2730464A (en) * | 1951-05-17 | 1956-01-10 | Shell Dev | Antistatic treatment of textile yarns |
US2877178A (en) * | 1955-12-20 | 1959-03-10 | Gen Aniline & Film Corp | Ampholytic compositions in wet treatments |
US2956949A (en) * | 1955-10-19 | 1960-10-18 | Eastman Kodak Co | Fiber treating compositions |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE559500C (de) * | 1927-07-26 | 1932-09-20 | Chemische Ind Ges | Verfahren zur Herstellung quaternaerer Ammoniumsalze |
US2742464A (en) * | 1951-04-25 | 1956-04-17 | Koebner Adolf | Production of capillary active amine-amides |
US2777872A (en) * | 1953-11-02 | 1957-01-15 | Du Pont | Unsaturated organic compounds |
US2805135A (en) * | 1954-08-25 | 1957-09-03 | Eastman Kodak Co | Stabilized hydrocarbon fuel oil compositions and stabilizaers therefor |
US2802785A (en) * | 1954-08-30 | 1957-08-13 | Union Oil Co | Water flooding process |
US2883370A (en) * | 1954-10-19 | 1959-04-21 | American Cyanamid Co | Copolymer of acrylonitrile, a quaternary ammonium compound and at least one additional comonomer |
US2993918A (en) * | 1956-04-02 | 1961-07-25 | John J Mccabe Jr | Novel compositions of matter and methods for preparing them |
-
0
- BE BE624404D patent/BE624404A/xx unknown
-
1961
- 1961-11-06 CH CH1222862A patent/CH414935A/de unknown
-
1962
- 1962-10-25 US US233145A patent/US3211646A/en not_active Expired - Lifetime
- 1962-10-25 US US233150A patent/US3174985A/en not_active Expired - Lifetime
- 1962-11-01 GB GB41451/62A patent/GB966822A/en not_active Expired
- 1962-11-01 GB GB41452/62A patent/GB971527A/en not_active Expired
- 1962-11-05 AT AT870162A patent/AT238130B/de active
- 1962-11-05 DE DE1419420A patent/DE1419420C3/de not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2589674A (en) * | 1947-05-24 | 1952-03-18 | American Cyanamid Co | Aliphatic amido propyl quaternary ammonium salts |
US2730464A (en) * | 1951-05-17 | 1956-01-10 | Shell Dev | Antistatic treatment of textile yarns |
US2626876A (en) * | 1951-08-17 | 1953-01-27 | American Cyanamid Co | Antistatic treatment of articles comprising a vinyl resin and treated articles |
US2717842A (en) * | 1952-09-10 | 1955-09-13 | American Cyanamid Co | Antistatic treatment and treated products |
US2956949A (en) * | 1955-10-19 | 1960-10-18 | Eastman Kodak Co | Fiber treating compositions |
US2877178A (en) * | 1955-12-20 | 1959-03-10 | Gen Aniline & Film Corp | Ampholytic compositions in wet treatments |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3548036A (en) * | 1962-11-02 | 1970-12-15 | Basf Ag | Polymonoolefins containing an amine antistatic additive dispersed therein |
US4264516A (en) * | 1977-08-01 | 1981-04-28 | Ciba-Geigy Corporation | Quaternary ammonium salts of antistatic agents or softening agents containing fatty acid radicals, process for the production and use thereof |
EP0292481A1 (fr) * | 1986-10-23 | 1988-11-30 | Frank H Stevens | Composition particulaire emulsifiable pour lotion capillaire. |
US4891214A (en) * | 1986-10-23 | 1990-01-02 | Sherex Chemical Company, Inc. | Particulate emulsifiable hair conditioning composition |
EP0292481A4 (fr) * | 1986-10-23 | 1990-05-14 | Frank H Stevens | Composition particulaire emulsifiable pour lotion capillaire. |
Also Published As
Publication number | Publication date |
---|---|
US3174985A (en) | 1965-03-23 |
DE1419420A1 (de) | 1968-10-03 |
AT238130B (de) | 1965-01-25 |
CH414935A (de) | 1966-06-15 |
GB971527A (en) | 1964-09-30 |
BE624404A (fr) | |
GB966822A (en) | 1964-08-19 |
DE1419420B2 (de) | 1973-12-06 |
DE1419420C3 (de) | 1974-07-04 |
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