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
- 239000000203 mixture Substances 0.000 title claims description 30
- 229920002994 synthetic fiber Polymers 0.000 title claims description 12
- 239000012209 synthetic fiber Substances 0.000 title claims description 12
- -1 MONOCARBOXYLIC ACID SALT Chemical class 0.000 claims description 9
- 239000002585 base Substances 0.000 description 41
- 125000004432 carbon atom Chemical group C* 0.000 description 34
- 239000002480 mineral oil Substances 0.000 description 28
- 235000010446 mineral oil Nutrition 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000835 fiber Substances 0.000 description 9
- UCWYGNTYSWIDSW-QXMHVHEDSA-N (z)-n-[3-(dimethylamino)propyl]octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCCN(C)C UCWYGNTYSWIDSW-QXMHVHEDSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- WCSBDRIEINNXNW-YPKPFQOOSA-N (z)-n-[2-(diethylamino)ethyl]octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCN(CC)CC WCSBDRIEINNXNW-YPKPFQOOSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- TWMFGCHRALXDAR-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCCN(C)C TWMFGCHRALXDAR-UHFFFAOYSA-N 0.000 description 1
- WWVIUVHFPSALDO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C WWVIUVHFPSALDO-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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 [having hydrocarbon substituents containing less than thirty carbon atoms]
-
- 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 [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] 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
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- 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 (en, 2012) |
AT (1) | AT238130B (en, 2012) |
BE (1) | BE624404A (en, 2012) |
CH (1) | CH414935A (en, 2012) |
DE (1) | DE1419420C3 (en, 2012) |
GB (2) | GB966822A (en, 2012) |
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 |
US4891214A (en) * | 1986-10-23 | 1990-01-02 | Sherex Chemical Company, Inc. | Particulate emulsifiable hair conditioning composition |
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 (4)
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 |
US4891214A (en) * | 1986-10-23 | 1990-01-02 | Sherex Chemical Company, Inc. | Particulate emulsifiable hair conditioning composition |
EP0292481A4 (en) * | 1986-10-23 | 1990-05-14 | Frank H Stevens | PARTICULATE EMULSIBLE HAIR CONDITIONER. |
Also Published As
Publication number | Publication date |
---|---|
AT238130B (de) | 1965-01-25 |
GB971527A (en) | 1964-09-30 |
DE1419420B2 (de) | 1973-12-06 |
BE624404A (en, 2012) | |
GB966822A (en) | 1964-08-19 |
CH414935A (de) | 1966-06-15 |
US3174985A (en) | 1965-03-23 |
DE1419420C3 (de) | 1974-07-04 |
DE1419420A1 (de) | 1968-10-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2528378A (en) | Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same | |
EP0656048B1 (en) | Liquid softener composition | |
US2809159A (en) | Antistatic and rewetting treatment of textile material | |
US3211646A (en) | Composition for reducing readiness with which synthetic fibers accept an electric charge | |
US5696070A (en) | Quarternary ammonium salt, method for production thereof, and softener composition using salt | |
JPH0441776A (ja) | 液体柔軟仕上剤 | |
EP0342331B1 (de) | Ziehfähige Zusammensetzung für die Behandlung von polyesterhaltigen Fasermaterialien | |
US2970158A (en) | Surface active agents | |
US4014800A (en) | Fiber-lubricating compositions | |
US2740759A (en) | Preparation for treating textile fibers and yarns | |
JPS63282372A (ja) | 柔軟仕上剤 | |
DE69533466T2 (de) | Flüssige Weichspülerzusammensetzung | |
JP3791117B2 (ja) | 柔軟剤組成物 | |
DE69230056T2 (de) | Weichmacherzusammensetzungen für Textilien | |
KR20010049208A (ko) | 합성섬유용 처리제 및 합성섬유의 처리방법 | |
US3634117A (en) | A textile material coated with an ammonium dialkyl phosphate antistatic agent | |
JPH09105076A (ja) | 液体柔軟仕上剤組成物 | |
US3240715A (en) | Alkylolamide surface active compositions soluble in aqueous solutions of electrolytes | |
US4865768A (en) | Phosphoric acid salt of the reaction product of a mono-carboxylic acid with a polyamine | |
JP2763651B2 (ja) | 柔軟仕上剤 | |
US3719597A (en) | Acyl-amino-pr opyl-dialkylammonium dialkyl phosphates as textile finishing agents | |
US3775446A (en) | Acyl-amino-propyl-dialkylammonium dialkyl phosphates | |
JP2003003369A (ja) | 柔軟基剤及び柔軟仕上剤 | |
JPH04333666A (ja) | 液体柔軟剤組成物 | |
JP3195501B2 (ja) | 液体柔軟仕上剤組成物 |