US3862045A - Antistatic softening composition - Google Patents

Antistatic softening composition Download PDF

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US3862045A
US3862045A US30485972A US3862045A US 3862045 A US3862045 A US 3862045A US 30485972 A US30485972 A US 30485972A US 3862045 A US3862045 A US 3862045A
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antistatic
ammonium
alkyl
softening
composition
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Toshio Sato
Mamoru Katsumi
Natsuko Tsuda
Akira Yoshida
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Kao Corp
Kao Soap Co Ltd
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Kao Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/325Amines
    • D06M13/342Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/372Treating 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 containing etherified or esterified hydroxy groups Polyethers of low molecular weight
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms

Abstract

An antistatic fabric softening composition comprising the following four ingredients (I) to (IV): I. 4 - 10% by weight of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms; II. 0.5 - 3.0% by weight of at least one antistatic agent selected from compounds expressed by the following formula

WHEREIN R1 is an alkyl group having 14 to 22 carbon atoms, R2 stands for an alkyl group having 1 to 3 carbon atoms of a benzyl group, X designates Cl, Br or C2H5SO4, and the sum of m and n is from 5 to 20, AND COMPOUNDS EXPRESSED BY THE FOLLOWING FORMULA

WHEREIN R3 is an alkyl group having 16 to 22 carbon atoms, R4 and R5 stand independently for an alkyl group having 1 to 3 carbon atoms, and p is a number of from 1 to 4; III. 0.5 - 2.0% by weight of at least one non-ionic surfactant containing an alkyl group having 8 to 18 carbon atoms and having 40 - 90 moles of ethylene oxide units; and IV. 2 - 10% by weight of at least one additive selected from the group consisting of alcohols having 1 to 3 carbon atoms, glycols having 2 to 3 carbon atoms, glycerol, sorbitol and urea.

Description

. United States Patent Sato et al.

[11] 3,862,045 1 Jan. 21, 1975 [54] ANTISTATIC SOFTENING COMPOSITION I [75] Inventors: Toshio Sato; Mamoru Katsumi;

Natsuko Tsuda; Akira Yoshida, all of Wakayama, Japan [731' Assignee: Kno Soap Co., Ltd., Chuo-ku,

Tokyo, Japan 22 Filed: Nov. 8, 1972 21 Appl. No.: 304,859

[30 Foreign Application Priority Data Nov .15, 1971 Japan 46-91342 [52] U.S. CL... 252/8-75, 252/88, 252/545, 252/547 [51] Int. Cl 006m 13/46 [58] Field of Search 8/187, 188; 252/86, 8.75,

[56] References Cited UNITED STATES PATENTS 3,578,592 5/1971 Pontelandolfo 252/88 3,681,241 8/1972 Rudy 252/88 X 3,703,480 11/1972 Grand et al.'... 252/88 X 3,756,950 9/1973 Gluck 252/88 X Primary Examiner-Stephen J. Lechert, Jr. Attorney, Agent, or Firm-Woodhams, Blanchard and Flynn [57] ABSTRACT An antistatic fabric softening composition comprising the following four ingredients (I) to (1V):

1. 4 10% by weight of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms;

11. 0.5 3.0% by weight of at least one antistatic agent selected from compounds expressed by the following formula (CH CH O) H wherein R, is an alkyl group having 14 to 22 carbon atoms, R stands for an alkyl group having 1 to 3 carbon atoms of a benzyl group, X designates Cl, Br or C H SO and the sum of m and n is from 5 to 20,

and compounds expressed by the following formula wherein R is an alkyl group having. 16 to 22 carbon 4 Claims, No Drawings 1 v ANTISTATIC SOFTENING COMPOSITION FIELD OF THE INVENTION This invention relates to a fabric softening composition which is stable even at high concentrations and which imparts an excellent antistatic property.

DESCRIPTION OF THE PRIOR ART Softening agents have heretofore been used frequently as finishing agents for textile fabrics. They are utilized mainly for-finishing underwears and diapers after washing thereof to impart soft touch to these textile fabrics. Important properties required of softening agents are as follows.

a.'They impart a soft touch or feeling to treated textile fabrics.

b. They impart an antistatic property-to treated textile fabrics.

c. They do not reduce water absorption of treated textile fabrics.

d. Even in the form of concentrated liquid fabric softener solutions, they are stable at the temperature encountered during the marketing process and during the laundering process and they can maintain 1 low viscosity under such environmental changes.

Among the above properties, the property (a) should naturally be required at'first and is most important among the above properties. However, also each of properties (b) to (d) has a great significance in actual applications.

Fabric softening agents of various compositions are known in the art, but most of them' comprise as a main ingredient a quaternary, ammonium salt having two long-chain alkyl groups.

In some instances, non-ionic surfactants such as alkylphenol-ethylene oxide adducts and solvents such as alcohols and/or glycols are added to such main ingredient so as to improve the solution stability and other properties. Although fabric softening agents of known compositions can give satisfactory softening effects, any of them fails to exhibit sufficient effects with respect to properties (b) to (d), especially antistatic property and stability.

Consumption of clothes and garments composed of synthetic fibers has recently increased very rapidly, but clothes of synthetic fibers are fatally defective in, that they are readily statically charged as compared with clothes of natural fibers. When the fabrics are statically charged, they tend to catch dust thereon very easily or cling to the body, or tend to generate sparks on wearing or undressing. It is well known that these undesired phenomena caused by accumulation of static chargesare great disadvantages of clothes and garments of synthetic fibers.

It is necessary to solve the problem that liquid soften-- ers frequently undergo phase separation and have a tendency to be very viscous under various climate and temperature conditions unless the active softening ingredients are present only in low concentrations. Further, it is also required that softening agents are hardly frozen or solidified at temperatures around the freezing point and, if they become frozen or become extremely viscous at these low temperatures, they must readily recover their original viscosities when the temperature is returned to room temperature.

In order to impart antistatic activity-to a fabric softening agent, it may at first be considered to incorporate into the composition an antistatic agent. However, when for instance, stearyl trimethyl ammonium chloride, which is an antistatic agent broadly used, is incorporated into a fabric softening agent comprising as a 5 main ingredient a quaternary ammonium salt having two long-chain alkyl groups, an antistatic effect may be attained, but the stability of an aqueous solution of the agent is extremely lowered, with the result that the agent is no longer applicable to practical use. Further,

the incorporation of such antistatic agent is accompanied with a disadvantage-that discoloration or quenching of fluorescence is brought about in the case of clothes treated with an anionic direct dye or an anionic fluorescent dye. Further, even if such softening agent comprising the above quaternary ammonium salt and an antistatic agent-is incorporated with a known solution stabilizer comprising an alkylphenol-ethylene oxide adduct or other similar non-ionic surfactant and a solvent such as alcohols and glycols, the resulting composition is still inferior in the solution stability. On the other hand, when other well-known anti-static agents are employed, the resulting compositions are more or less defective in the point of antistatic performance, solution stability, yellow discoloration of solutions and so on, and they cannot be applied to practical use. As a result of research works made with a view to developing an antistatic softening composition free of the above-mentioned defects, we have found that when a specific antistatic agent is incorporated into a specific softening composition, the above defects can be overcome, and based on this finding we have arrived at this invention.

SUMMARY OF THE INVENTION Accordingly, this invention provides a softening composition which exhibits an excellent softening effect to fabrics and a sufficient solution stability even at a high concentration and which can impart an excellent antistatic property to the treated textile fabrics. ln accordance with this invention, there is provided an antistatic softening composition comprising the following four ingredients (I) to-(IV):

I. 4 10 percent by weight of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms;

II. 0.5 3.0 percent by weight of at least one antistatic agent selected from compounds expressed by 'the following formula- (ea ca m R -'N R X and compounds expressed by the following formula 3 wherein R is an alkyl group havnig l6 to 22 carbon atoms, R, and R stand independently for an alkyl group having 1 to 3 carbon atoms, and p is a number of from 1 to 4; having lll. 0.5 2.0 percent by weight of at least one nonionic surfactant containing an alkyl group having 8 to 18 carbon atoms and having 40 90 moles of ethylene oxide units; and

IV. 2 percent by weight of at least one additive selected from the group consisting of alcohols having l to 3 carbon atoms, glycols having 2 to 3 carbon atoms. glycerol. sorbitol and urea.

The balance of the composition is water.

Now, description will be made on preferred compounds.

As the quaternary ammonium salt (I), there may be preferably mentioned, distearyl dimethyl ammonium chloride and di-halogenatcd-tallt)walkyl dimethyl ammonium chloride. Preferable examples ofthe non-ionic surfactant (lll) include R,;()(CH CH Ol,,,H (in which R.; is an alkyl group having l2 to 18 carbon atoms),

The composition of this invention comprising the above ingredients alone can fully attain the intended objects of this invention, but in order to ensure the stability on storage for a long period. it is preferred that the composition is incorporated with a small amount of an inorganic salt such as NaCl and Na SO,. usually ().()l to 0.5 percent by weight. The composition of this invention is further characterized in that. when a fluorescent dye of the distilbene or diaminostilbene type is incorporated in the composition ofthis invention. the fluorescent dye exhausts on the fabrics and acts effectively.

This invention will now be illustrated more specifically by reference to Examples.

EXAMPLE l Antistatic agents were incorporated into a softening composition, and the solution stability, and the antistatic effect and other properties of treated products were 7 (in WhlCh R7 iS an alkyl group having 8 IO 12 carbon Distearyl dimethyl ammonium 6.4% by weight atoms) and R,,COO(CH CH O),,,H.(in which R, is an zl gi by weight alkyl group having 1 l to 17 carbon atoms), in each of Nrmylphenol polyoxyethylenc 1:07! by weight which it is preferred that m is a number of from to E l e s U h h 90. Propylene glycol, ethylene glycol, glyeerine and 30 mf' z urea are preferable as the additive (IV). WLlltJI' balance Properties Change in of Treated Solution State Textile Fabrics .u a a Antistatic Agent l3 3 3 m w ill 31 5-H m t q E. a:

-n-'U H It! M ---l 1 -1 Q) 'U 'U O U a 1) 0; -H "4 m 44 H E o o in tn 4- H m a 25* ..-s B 2 o H ca U a .m a (D U (D E 'u U U 0 u 4-? u. .2 t3 8 E ii) 8 "8 3 3 E fll tg l m 3'3 A 7 CH I 3 R -tilCH ci 920 x A A x 0 0 x h CH B 7 CH I 3 R -N-CH c9." 470 x x x x 0 x x R -4:48 C2, A X X X 0 X X CH (1%) 7 C .m .naes 8 Properties Change in of Treated Solution State Textile Fabrics 4 o u at?! m 42 Antistatic Agent e +1 m m o H :3 m 1 v E cu 'HI'G H r6 G! "-1 1 a) '0 e 4 u u o a -.-i -|-l m 4 v-l E O Q If) (I) H II) m ss a a s 0 u ru 0 e m "3 o u w E 'o u u o u u u tn-t O o o O H .1 .p .H -v-1H OO 0 0 N O C Cl) A: i m Hv-l lm m 3 3 n -otnm a 2,73ox x (I) A Ax A o @-0(Eo) u 2,680X x A A A x A o x N (EO) H l R CON :490 A A O A O X A X (EO) H m+n=5 R COO(E0) H 762 X X A A A X A O P (E0) H R -N 838 x A A x A x A x Notes:

1. EO means C H O and Rcoco indicates a coconut alkyl (cocoyl) group.

2. The viscosity is expressed in the cps unit.

3. 20C.; 5 times means the state of the solution observed after the procedure of freezing at 20C. and rc-melting at C. has been repeated 5 times.

4. R indicates an alkyl group ofC,H and R shows the presence of a double bond.

5. Each mark has the following meaning:

@ particularly excellent 0 excellent and sufficient A performance being slightly insufficient and state being accompanied with a little degradation X insufficient performance and state with a considerable degradation and not applicable to practical use.

From the above results, it is recognized that compositions incorporated with anionic antistatic agents H to K and non-ionic antistatic agents L and P fail to impart intended antistatic performance to treated products, and other performances and stability are also insufficient. Compositions incorporated with cationic antistatic agents A to D can impart sufficient antistatic property. but compositions incorporated with antistatic agents A, B, B and D are defective in solution stability and whiteness of the treated fabrics and they are not usable for practical applications. Although the composition incorporated with antistatic agent C is not completely satisfactory, it can be put into practical use. The composition incorporated with antistatic agent C is especially excellent in various properties. Compositions incorporated with amphoteric antistatic agents E to G can impart sufficient antistatic property, but compositions incorporated with antistatic agents F and G are defective in stability and whiteness of the treated product and they cannot be put into practical use.

EXAMPLE 2 In connection with the antistatic agent-containing compositions (C, C and E) which exhibited excellent properties in Example I, the influences of the number of moles of the ethylene oxide (EO) units of the nonionic surfactant and the additives to those compositions were examined to obtain compositions having more excellent properties and being applicable to practical use. Results are shown in Table 2.

The following three composition systems were tested, in which each percentage ratio was on the weight basis.

, 9 10 System-Q v Distearyl dimethyl amxtimnchloxide 7.0%

tem n R N-CH c2 1.0%

H (m+n=6) Nonylphenol polyoxyethylene (x) ether 1.0%

Urea 0 9% "Sodium chloride o 02% water 7 balance Szitem R bistoeryl dimethyl emoniu'm chloride 7.6%

' (Em fl a I I I 11 N -c a c u sof 2 .02

(E l fl (m+n=20) Stearie acid polycxyethyleneixl ether 0.5% web 1m; o 9% Sodium chlozide 0.02%

Water balance Szstem I v f a nipz n ril intbyl "l eride I 720'! a -z'q -ca coo- 2.0x

- Nonylphenol pol lyoxyethylene (x) ether 1.0%

Una: y I

' Sqdium emu-nee I 0.02%

filter i i a ii In the a O c, X iS ethylen OXide m um r. This procedure was repeated 5 times and the condition Properties were measured and evaluated according of the sample was examined. to the following methods: 3. Dispersion stability:

The sample was allowed to stand in a thermostat chamber maintained at 50C. for 1 month, and the state i of the sample was examined as to whether the phase separation was caused.

Each mark has the following meaning: (9: particularly excellent I. Viscosity at room temperature:

The compositions were allowed to stand at room temperature for l month after blending, and the viscosities were measured at 30C.. each value being expressed in the cps unit.

0 excellent 2. recovery after freezing: The sample was allowed to stand at 2()C. for 1 day to freeze it, and it was defrosted at room temperature. X i ffi i A slightly insufficient -'1elp1e 2 Pro er Recove assets? 1:221 2121:1213 g fgleditgie' 9 o 3 6 9 3 6 9 '33 '13) o 3 6 '10 7 760 950 1060? x x x x x x x 20 450 190 240 Asa-ox x x x x x x x so 31.0 no 145 215 11 1; x A 1: "40* I068' 7 as 759x 0 o A oo 01A 7a 75 70 x e o- @v A Q 10 a0 84.86 X@@O0@A ss -9 a 111 as ,58 x o e A 210 250 316 336" x A o A A e 'o 2i, 329-1200 1400 911a x x -x x xxx 1;

10- 735 560719 lllZXXQXXXXXil 20. 2.16 e10 e21- 816 x x x' x x x x 3.0 "-1150- 215 1tv x A 1: x101; 40 10s as s9 as x a e A ;;A. o a; so 3 9a 7a e4 s4 sap a] i I 1 70- 111m 61 "r7 100 1'60 .120 94' fiat- :1 0 A 411 was 12400 M100 it x x x 4100 use 6400 6180 x 1c 1709. 4-10 120 11.0 x A A TA 1400, no 110 I 1.40 0 o sso arm -11 s 5e 951,0 0 .0 'i 10" 5 80 as- 79 I ZZA XiO o #0 1 3112 a? 'm we ice h Iiio" 1 11f 160 x} A 1 1 120 aoao no "620 710 x x i a EXAMPLE 3 1. Viscosity: Examples of compositions included in the scope of Th viscosity was measured in the same manner as in this invention are illustrated in Table 3, each of which Example 1, each value being expressed in the cps unit.

has excellent properties and can be put into practical 2. Frictional Electrification Voltage:

use. I Polyester fabric swatches and acrylic fabric swatches Data of stability, antistatic characteristic and other were respectively dipped in a 0.1 or 0.3 percent soluproperties of these compositions are shown in Table 4. tions of each softening composition (the weight ratio of The properties were measured and evaluated according the fabrics to the treating solution was 1:20). Agitation to the following methods. was applied for 5 minutes, and the fabrics were 13 squeezed ata squeeze ratio of I percent and dried. The cloths were allowed to stand at a temperature of C. and a relative humidity of percent for 2 days. The resulting fabrics were used as samples. The frictional electrification voltage was determined by employing a rotary static tester (Kaken type of Kyoto University). in general, it is admitted that, when the frictional electrification voltage is lower than 300 volts (V), troubles due to static electricity can be neglected.

incidentally, when the above starting fabric swatches were subjected to this static testwithout treatment with the antistatic softening composition of this invention, it was found that the-polyester fabric swatches exhibited a frictional electrification voltage of-2,2OO V and the acrylic fabric swatches exhibited 1,900 V.

3. Softness:

A cotton towel cloth, a bleached cotton diaper cloth and an acrylic blanket were respectively washed according to an ordinary method, and treated with a ().l or 0.3 percent solution of the softening composition, followed by drying. Each sample was subjected to the touch test by 5 men and 5 women, and the softness was evaluated based on points given to the sample. Each value shown in Table 4 is the sum of points given by each tester. Thus, a higher value means a higher softness.

4. Water Absorption:

A cotton broadcloth was treated with a ().l or 0.3 percent solution of the softening composition and dried. The resulting cloth was used'as a test sample. The water absorption was measured according to Klemm method (the method in which the sample cloth is kept in the vertical state, the bottom 'is'dipped in water, and the rate of water rise is measured). In Table 4', the position of water rising within 1 minute from dipping was expressed in the cm unit.

Compo- Quaternary Table 3 I Y sition Amt'itonium Non-Ionic No. alh Anti static-Agent Surfactant Additive Others 1 distearyl dimethyl stearyl methyl nonylphenol urea (4.0%)

ammonium chloride dipolyoxyethylene (8) pol-yoxyethylene (7.0%) ammonium chloride (85) ether (0.9%)

1 2 distearyl dimethyl stearyl methyl nonylphenol urea (4.0%) Na'CIL ammonium chloride dipolyoxyethylene (8) polyo'xyethylene (0.02%)

(7.0%) ammonium chloride (85) ether (0.9%) v (0.9%)

3 di-hydrogenatedpalmityl benzyl nonylphenol sorbitol NaBr beef-tallowdipolyoxyethylene (8) polyoxyethylene (4.0%) (0.04%) alkyl diethyl ammonium chloride ether (1.0%) ammonium bromide (2.0%)

4 distearyl dimethyl'. behenyl methyl stearic acid propylene NaCR.

ammonium chloride dipolyoxyethylene (20) polyoxyethy'lene glycol (0.02%) (7.0%) ammonium chloride ester (1.0%) (8.0%)

5 dipalmityl stearyl propyl lauryl alcohol ethanol Na S0 dihydroxyethyl dipolyoxyethylene(l5) polyoxyethyle'ne (7.0%) (0 05%) ammonium chloride ammonium chloride (50) ether (0.5%)

6 di--hydrogenated hydrogenated-beefoctylalcohol urea (2.0%) NaCl beef-tallow tallo'walkyl' ethyl polyoxyethylene sorbitol (0.02%) alkyl methyl dipolyoxyethylene (6) (50) ether (0.5%) (3.0%) ethyl-ammonium ammonium ethosulfate ethosulf ate (6.0%) (1.5%)

7 dibehenyl dinethyl hydrogenated-rbeef nonylphenol glycerine NaCR.v

' amn'oni-um chloride tallow alkyl .methyl polyoxyethylene (3.0%) (0.03%)

(5.0%) dipolyoxyethylene (20) ether (0. 8%)

. ammonium chloride 8 di-hy'droQenated- CH nonylphenol ethylene NaCl 1 beef-tallow-alkyl R 4 6 6) polyoxyethylene glycol (0.02%)

. dimethyl ammonium 18 2 (50) ether (1.0%) (5.0%)

chloride (7.0%) CH (2.0%)

'9 i distea -Yl methyl stearic acid" egrlgitol 121333-285) h dro eth 1 polyoxyethylene ammonis um bzomide 16 CHZCOOG (so) ester (1.0%) (7.0%) CH (2.5%)

10 dibehenyl dimethyl- C H stearyl alcohol ethanol Na SO ammonium chloride R fi-B (CH 6 polyoxyethylene (5.0%) (0.01%)

(7.0%) i 22 2 3 (50) ether (2.0%)

ll di-hydrogenated- C H nonylphenol urea (3.0%) NaCl beef-tallow- Q polyoxyethylene (0.02%)

dimethyl. ammonium 22 2 ether (1.0%)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. An antistatic fabric softening composition com-- tca ca m a R-N-R X I (ca cn o) I-l wherein R, is an alkyl group having l4 to 22 carbon atoms. R stands for an alkyl group having I to 3 carbon atoms or a benzyl group. X designates Cl, Br or C H SO and the sum of m and n is from 5 to 20,

and compounds expressed by the following formula (CH g-C wherein R is an alkyl group having 16 to 22 carbon atoms, R, and R stand independently for an alkyl group having 1 to 3' carbon atoms, and p is a number of from 1 to 4;

III. 0.5 2.0 percent by weight of at least one nonionic surfactant containing an alkyl group having 8 to 18 carbon atoms and having 40 moles of ethylene oxide units; and (IV) 2 10 percent by weight of at least one additive selected from the group consisting of alcohols having 1 to 3 carbon atoms, glycols having 2 to 3 carbon atoms, glycerol, sorbitol and urea.

2. An antistatic softening composition according to claim 1, in whichsaid quaternary ammonium salt is selected from distearyl dimethyl ammonium chloride and di-halogenated-tallowalkyl dimethyl ammonium chloride.

3. An antistatic softening composition according to claim 1, in which said non-ionic surfactant (lll) is selected from the compounds represented bythe following formulas:

R.,O(CH CH O),,,H (in which R is an alkyl group having 12 to 18 carbon atoms),

group of propylene glycol, glycerine and urea.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 862 045 Dated January 2L, 1975 'Ioshio Sato, Mamoru Katsumi, InV n Natsuk Tsur'ia' and Akira Yoshida It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

On the title page, in the Assigneeportion; change "Kno Soap Co. Ltd." to ---Kao ,Soap Co. Ltd.---,

Col. 15, line 26; replace the incorrect formula with the following:

:4 R3 T (CH COO and sealed this 15th day of japril 1"" Fracomerks F ORM P04 050 (10-69) USCOMM-DC 6037 6-P69 U5 GOVERNMENY PRINTING OFFICE:

Claims (3)

  1. 2. An antistatic softening composition according to claim 1, in which said quaternary ammonium salt is selected from distearyl dimethyl ammonium chloride and di-halogenated-tallowalkyl dimethyl ammonium chloride.
  2. 3. An antistatic softening composition according to claim 1, in which said non-ionic surfactant (III) is selected from the compounds represented by the following formulas: R6O(CH2CH2O)mH (in which R6 is an alkyl group having 12 to 18 carbon atoms),
  3. 4. An antistatic softening composition according to claim 1, in which said additive (IV) is selected from the group of propylene glycol, glycerine and urea.
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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4038196A (en) * 1975-03-12 1977-07-26 Kao Soap Co., Ltd. Softening agent for woven fabrics
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4144367A (en) * 1977-05-09 1979-03-13 Minnesota Mining And Manufacturing Company Carpet-treating compositions
US4160823A (en) * 1976-03-29 1979-07-10 Kao Soap Co., Ltd. Transparent hair rinsing composition
US4203872A (en) * 1975-08-01 1980-05-20 Flanagan John J Surfactant system
US4222905A (en) * 1978-06-26 1980-09-16 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal performance
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
US4259217A (en) * 1978-03-07 1981-03-31 The Procter & Gamble Company Laundry detergent compositions having enhanced greasy and oily soil removal performance
US4264479A (en) * 1978-12-18 1981-04-28 Flanagan John J Surfactant system
US4268401A (en) * 1975-07-02 1981-05-19 Blendax-Werke R. Schneider Gmbh & Co. Liquid detergent compositions having washing and softening properties
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4369134A (en) * 1980-02-05 1983-01-18 Kao Soap Co., Ltd. Creamy cleansing compositions
US4391605A (en) * 1980-08-07 1983-07-05 Wool Development International Limited Textile treatment
US4493773A (en) * 1982-05-10 1985-01-15 The Procter & Gamble Company Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants
US4540521A (en) * 1984-01-16 1985-09-10 National Distillers And Chemical Corporation Liquid quaternary ammonium antistatic compositions
FR2586425A1 (en) * 1985-08-20 1987-02-27 Colgate Palmolive Co liquid detergent compositions containing stabilizing agents in suspension and an additive of urea type and processes for cleaning fabrics using the
US4789496A (en) * 1985-08-20 1988-12-06 Colgate-Palmolive Company Built nonaqueous liquid nonionic laundry detergent composition containing
US4844822A (en) * 1987-07-06 1989-07-04 The Dial Corporation Softener/antistat compositions
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US5336447A (en) * 1990-11-30 1994-08-09 Lever Brothers Company, Division Of Conopco, Inc. Process and composition for treating fabrics
US6369159B1 (en) 1987-05-13 2002-04-09 Pdm Holdings Corp. Antistatic plastic materials containing epihalohydrin polymers
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US20160215237A1 (en) * 2013-10-10 2016-07-28 Akzo Nobel Chemicals International B.V. Fabric Softener Composition and The Use Thereof

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DE2525610C2 (en) * 1975-06-09 1985-04-11 Henkel Kgaa, 4000 Duesseldorf, De
JPS52141446U (en) * 1976-04-17 1977-10-26
JPS5619846Y2 (en) * 1979-06-27 1981-05-12
DE3415892A1 (en) * 1983-05-11 1984-11-15 Colgate Palmolive Co Concentrated fabric softening composition and method for producing same
JPS61102481A (en) * 1984-10-25 1986-05-21 Lion Corp Softening composition
JP2660205B2 (en) * 1988-06-03 1997-10-08 ミヨシ油脂株式会社 Method for producing a fiber treating agent

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US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening
US3703480A (en) * 1970-11-16 1972-11-21 Colgate Palmolive Co Fabric-softener compositions
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US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening
US3703480A (en) * 1970-11-16 1972-11-21 Colgate Palmolive Co Fabric-softener compositions
US3756950A (en) * 1971-03-08 1973-09-04 Lever Brothers Ltd Fabric softening compositions

Cited By (25)

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Publication number Priority date Publication date Assignee Title
US4038196A (en) * 1975-03-12 1977-07-26 Kao Soap Co., Ltd. Softening agent for woven fabrics
US4268401A (en) * 1975-07-02 1981-05-19 Blendax-Werke R. Schneider Gmbh & Co. Liquid detergent compositions having washing and softening properties
US4203872A (en) * 1975-08-01 1980-05-20 Flanagan John J Surfactant system
US4160823A (en) * 1976-03-29 1979-07-10 Kao Soap Co., Ltd. Transparent hair rinsing composition
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4144367A (en) * 1977-05-09 1979-03-13 Minnesota Mining And Manufacturing Company Carpet-treating compositions
US4259217A (en) * 1978-03-07 1981-03-31 The Procter & Gamble Company Laundry detergent compositions having enhanced greasy and oily soil removal performance
US4139477A (en) * 1978-03-16 1979-02-13 E. I. Du Pont De Nemours And Company Fabric conditioning compositions
US4222905A (en) * 1978-06-26 1980-09-16 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal performance
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
US4264479A (en) * 1978-12-18 1981-04-28 Flanagan John J Surfactant system
US4284435A (en) * 1979-11-28 1981-08-18 S. C. Johnson & Son, Inc. Method for spray cleaning painted surfaces
US4369134A (en) * 1980-02-05 1983-01-18 Kao Soap Co., Ltd. Creamy cleansing compositions
US4391605A (en) * 1980-08-07 1983-07-05 Wool Development International Limited Textile treatment
US4493773A (en) * 1982-05-10 1985-01-15 The Procter & Gamble Company Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants
US4540521A (en) * 1984-01-16 1985-09-10 National Distillers And Chemical Corporation Liquid quaternary ammonium antistatic compositions
FR2586425A1 (en) * 1985-08-20 1987-02-27 Colgate Palmolive Co liquid detergent compositions containing stabilizing agents in suspension and an additive of urea type and processes for cleaning fabrics using the
US4789496A (en) * 1985-08-20 1988-12-06 Colgate-Palmolive Company Built nonaqueous liquid nonionic laundry detergent composition containing
US6369159B1 (en) 1987-05-13 2002-04-09 Pdm Holdings Corp. Antistatic plastic materials containing epihalohydrin polymers
US4844822A (en) * 1987-07-06 1989-07-04 The Dial Corporation Softener/antistat compositions
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US5336447A (en) * 1990-11-30 1994-08-09 Lever Brothers Company, Division Of Conopco, Inc. Process and composition for treating fabrics
US20060138380A1 (en) * 2003-06-26 2006-06-29 Torsten Kulke Aqueous liquid compositions of cyclodextrine or cyclodextrine derivatives and a process using the said composition
US20160215237A1 (en) * 2013-10-10 2016-07-28 Akzo Nobel Chemicals International B.V. Fabric Softener Composition and The Use Thereof

Also Published As

Publication number Publication date Type
ES408371A1 (en) 1975-11-01 application
JPS4854300A (en) 1973-07-30 application
GB1410790A (en) 1975-10-22 application
DE2255260B2 (en) 1978-10-26 application
DE2255260C3 (en) 1979-06-21 grant
JPS5010439B2 (en) 1975-04-21 grant
DE2255260A1 (en) 1973-05-24 application

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