JPS6114281A - N-alkylisostearyl amide as antistatic - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION N-alkylisostearamides useful as antistatic agents for laundering textiles; detergent compositions containing an antistatically effective amount of said amides; and washing textiles with said compositions. A method of protecting textiles against electrostatic charging by contacting them within the fabric. These compounds provide optical brighteners in detergent compositions and antistatic protection while reducing detergent performance.

BACKGROUND OF THE PRIOR ART The present invention relates to a novel antistatic agent and detergent composition for use in the washing of textiles containing an antistatic agent which is an N-alkylisostearamide having the formula RC; 0NHR/. In the middle, Re○ is derived from isosteric acid,
R/ is 1 to 18 carbon atoms, preferably 7-18
A primary saturated or unsaturated aliphatic hydrocarbon containing 5 carbons.

The use of a wide variety of chemicals, particularly cationic quaternary ammonium compounds, as softeners and antistatic agents for textile products is very well known in the art. Also such substances for their antistatic and softening effects. Engineering 10, yo, 12 engineering. Oh 3,
Kay21. It is also well known that it is used as a substitute. This latter technique is incompatible with anionic detergents, which are one of the main types of detergents used in washing cycles, since the quaternary compounds previously used are primarily cationic in nature. This fact has made it necessary. Moreover, the quaternary compounds are not substantially effective in the presence of nonionic detergents.

It is also well known that washed articles tend to yellow or discolor when treated with the quaternary compounds mentioned above.

Another disadvantage associated with the use of non-ionic detergents in fabric washing with the above cationic agents is that they interfere with the deposition of the optical brightener onto the fabric, thereby containing this optical brightener. Decreases the optical brightener performance of detergent compositions.

Yet another drawback of cationic quaternary ammonium antistatic fabric softeners is that they interfere with the cleaning properties of detergents by reducing the soil removal performed by the detergents, resulting in a reduction in the cleaning effectiveness of anionic detergents. The presence of the substance negates the fabric softening properties of the cationic quaternary ammonium compound and also eliminates the minimal antistatic activity that the quaternary compound retains.

Accordingly, US Pat. No. 3,451,927 uses a fabric softening and antistatic active composition consisting of a quaternary ammonium compound coexisting with an alkylethanolamide in the water rinse during laundry.

N-alkyl fatty acid amides in which the alkyl group contains 1-22 carbon atoms are disclosed as suds suppressants in anionic detergents in U.S. Pat. No. 3,231,508; N containing 18 carbon atoms
-Alkyl fatty acid amide is US patent g 2,691,6
No. 36, N-to'decyl acetamide is disclosed as a foam stabilizer in anionic detergents; Used as foam enhancers; and higher alkyl hydroxy 7-acetamito-9 or -butyramides are described in U.S. Pat. No. 3,250,
No. 719 has been found to be useful as a suds improver in nonionic detergents.

R' is an aliphatic straight-chain or branched hydrocarbon group having a elementary atom, where R' is hydrogen or an aliphatic straight-chain or branched chain carbonization having from 1 to 10 carbons. Mono- or diamide, which is a hydrogen group, n is 1 or 2, and Ar is a substituted or unsubstituted aromatic group, is described in U.S. Pat.
, 891,912, pearling agents are used in shampoo compositions.
) used as

Anionic, amphoteric and/or non-ionic detergents containing higher alkyl polyhydrokylene carboxyamides as fabric softeners are disclosed in U.S. Pat. No. 3,654,166; and hydroxyl as fabric softeners. Higher fatty acid monoamides of chialkyl polyamines are disclosed in US Pat. No. 3,704,228.

Aliphatic amide-alkylene oxide reaction mixtures have also been utilized as fabric softeners for laundered fabrics, as disclosed in US Pat. No. 4,060,505.

N-substituted short chain carboxamides of secondary aliphatic beta amines have been used as antistatic agents in laundry processes, as shown in US Pat. No. 4,283,192.

Partially neutralized isostearic acid to a mixture of soap and acid generally forms a stable opaque liquid shampoo as shown in U.S. Pat. No. 3,590,122; This combination of salt and instearic acid is also described in U.S. Patent No. 4,097,
It has also been used as two components in the four-component emulsified and solubilized fat composition shown in No. 403.

Alkali metal salts of isostearic acid are disclosed in U.S. Patent Nos. 3 and 6.
No. 25,905, it was commonly used with non-cationic detergents in fabric softener compositions.

However, none of the above prior art discloses N-alkylisostearamides 8 as antistatic agents in anionic and/or nonionic detergents in the presence or absence of builders. Not yet.

SUMMARY OF THE INVENTION The N-alkylisostearamides of the present invention can be applied from cleaning solutions without inhibiting the performance of the detergent or interfering with the activity of optical brighteners that may be present in the detergent composition. It has now been discovered that it is an antistatic agent for synthetic textiles.

Therefore, a primary objective of the present invention is to protect textiles against electrostatic charging during machine drying following washing.

Another object of the present invention is to provide such protection in conjunction with conventional detergent compositions during the domestic laundry process.

Yet another object of the present invention is to provide antistatic agents that are active in the presence of builder-containing laundry detergents.

Another object of the present invention is to provide antistatic properties without compromising detergent properties and without reducing optical brightener performance.

Yet another object of the present invention is to provide antistatic compositions that can be used in single stage laundry operations with detergents and other cleaning additives, brighteners and laundry additives.

It is a further object of the present invention to provide a method for applying a protective treatment to fabrics during laundering to counteract subsequent electrostatic build-up.

Other objects, advantages and novel features of the invention will be set forth in part in the following description, and in part will become apparent to those skilled in the art upon consideration of the following content. , or may be learned by practicing the present invention. The objects and advantages of the invention may be realized and attained by means of the instruments and combinations particularly pointed out in the appended claims.

To achieve the above and other objects according to the present invention in the general terms embodied and broadly described herein,
The antistatic composition of the present invention for washing fabrics comprises an antistatic amount of N-alkylisostearamide expressed by the structural formula % where RCO is derived from instearic acid. and R' is a primary aliphatic saturated or unsaturated hydrocarbon chain containing from 1 to 18 carbons;
- treating the fabric with a composition containing an alkyl isostearamide either as a separate additive or premixed with the detergent during the washing cycle of the washing process.

More particularly, the antistatic property is determined by detergents, preferably anionic or nonionic detergents, N-alkylisostearamides as defined above, and builders, optical brighteners, enzymes, bleaching agents, etc. , and other conventional additives, by laundering the fabric in a composition containing other ingredients such as,

More particularly, the present invention relates to N-alkyl stearylamide as an antistatic agent for use in the washing cycle of textile laundering, and the invention relates to anionic, nonionic, The present invention relates to an antistatic composition for textile washing, comprising a detergent selected from the group consisting of amphoteric surfactants and mixtures thereof, and preferably builder salts and optical brighteners. A method of imparting antistatic properties to textiles during washing consists of treating the textiles during the entire washing cycle with the antistatic N-alkylisostearamide 9 described above.

The N-alkyl isostearamides 9 of the invention containing 1-18 carbon atoms derived from saturated or unsaturated primary amines reduce static electricity generation on cotton and synthetic textiles during washing. Reduce or prevent these antistatic properties by washing in detergent compositions containing the isostearamides described above, which are fully compatible with anionic, nonionic and amphoteric detergents; Antistatic agents can be applied to textiles by separate addition to the wash cycle during laundering. This same treatment imparts a soft hand to the cotton fabric and does not inhibit the detergent activity of the detergent composition. These beneficial effects are achieved without yellowing or discoloration of the fabric and without interfering with the action of optical brighteners that may be present in the detergent composition. These N-alkyl isostearamides have a pH
, thus allowing its use with builder-containing detergents.

The N-alkylisostearamides of the present invention can generally be made by conventional methods for amide synthesis. Isostearic acid is converted to the acid chloride by reaction with thionyl chloride, which is added to a primary amine dissolved in a solvent such as water, ether, or methylene chloride to form an amide. Isolated as a viscous liquid and waxy solid depending on the
Ru. The infrared spectrum is 3.05, 6.1 for secondary amide.
and.

Absorption characteristics at 6.5 microns are shown.

More qualitatively, the N-alkylisostearamides of the present invention are prepared by reacting isostearic acid, a branched isomer of stearic acid of the formula C17H35COOH with predominantly methyl branches, with thionyl chloride. It is prepared from known starting materials by a two-step process, first converting the isostearic acid chloride to the chloride and then reacting the stearoyl chloride with a primary aliphatic amine containing from 1 to 18 carbons. These reactions can be represented by the following formula, where R and R′ are as defined above: 2. RCOCA′+R′NH2−−−−RCON
The conversion of HR'+HCl isostearic acid to isostearoyl chloride is preferably carried out in the presence of dimethylformamide, which acts as a catalyst in this reaction. Since this amide reaction is exothermic and slow, cooling is desirable to control the temperature. This reaction is preferably carried out in the presence of water, any non-reactive solvent such as methylene chloride, methyl ether, benzene, chloroform, etc., and with the acid by-products formed during the reaction. It is carried out in the presence of any tertiary amine such as trimethylamine, pyridine and preferably triethylamine. The reaction mixture was washed sequentially with water or an alcohol/water mixture, dilute acid and water to remove any unreacted starting material, and NaSO
4 or similar neutral salts. The solvent is preferably removed by evaporation in vacuo. Obtained N
- The alkyl isostearamide is liquid, oil, or solid.

The following non-limiting examples illustrate ways to make compounds of the invention.

R is a complex mixture of branched chain isomers of stearic acid
CONH2CH2CH3 (Emery Industry.

Ginyoru Emazol 871).

14 g' (0.05 mol) of isostearic acid and 6.
5I (0.55 mol) of thionyl chloride was mixed with 0.1 ml of dimethylformamide under nitrogen gas.
(catalyst) was added. The mixture was stirred on a hot water bath for 20 minutes, then charged with N2 and stirred for an additional 10 minutes.

Infrared analysis readings show that some acid peaks are still present. Further K O,5& thionyl chloride was added and stirred for an additional VC of 10 minutes. The product obtained is instearoyl chloride. 7. This instearoyl chloride was dissolved in 70 ml of ether.
9 (0.12 mol) of n-propylamine,
Stirred for an additional 10 minutes at room temperature.

The amide was extracted with ether and twice with water, 5% H
Washed twice with C7 and again with water to neutrality, dried over Na2SO4 and evaporated in vacuo to give 14 g of light amber liquid. The bands of infrared analysis are 3290.3076°1645 and 1, which are typical of secondary amides.
Absorption at 546CTL is shown.

The instearoyl chloride prepared by the method of Example 1 was dissolved in 15Tn of 40% methylamine in 15M water.
1 and stirred in a water bath. The reaction mixture was heated at room temperature for 1
Stirred for 5 minutes, extracted with ether, washed twice with 5% HC, 1 solution and until neutral with water. Infrared analysis readings were representative of secondary amides.

Isosteric acid 1'0 of 209 according to the method of Example 1
．． Isostearoyl chloride prepared from 1 g of thionyl chloride 9 and 0.2 d of dimethylformamide was mixed with 11 g (0.85 mol) of n-octylamine in 100 ml of ether (10II, 0.19 mol).
of triethylamine. The reaction mixture was as in Example 2.
22 g of an amber oil are obtained, which exhibits an infrared spectrum value typical of secondary amide 9.

256 g (0,9 mol) isostearic acid, 128 &
(1,08 mol) of thionyl chloride and 4.
5m7! of dimethylformamide was placed in a flask surrounded by a hot water bath and stirred for 7 hours at 2 hours.

At this point, the infrared spectrum showed no unreacted acid. The HGII formed in this reaction is removed by N2
I blew it away. After 1 hour, the reaction mixture was heated in vacuo to remove excess thionyl chloride and distilled to recover instearoyl chloride, which was 140-15
Collected at a pressure of 0.2 mrn at 0°C242
The yield was 89% of theory.

Approximately 2 pieces of this isostearoyl chloride'' (54g)
5 minutes - 31 Cocoamine (C1o-014), 2
The mixture was added to 50ml of methylene chloride and triethylamine of group 25 while maintaining the temperature below 25°C. After the addition of inostearoyl chloride was complete, the mixture was stirred at room temperature for an hour. Transfer the reaction mixture to a separating funnel 2
Neutral to pH paper: twice with 5% alcohol/water mixture, then twice with 5% HGII, and again twice with alcohol/water mixture. I washed it until then. The reaction product was dried over Na 2 SO 4 and evaporated on a rotary evaporator to yield 79 g of a viscous oil of cocoisostearamide. The infrared spectrum is typical of secondary amides3
It shows strong absorption of 280.1642 and 1548.

56g (0.2 mol) of isostearoyl chloride'
of isosteric acid, 25 g (0.21 mol) of thionyl chloride, 1-dimethylformamide (0.0
14 mol) and 50rrLe methylene chloride (
reaction solvent) by stirring the mixture for 7 hours without heating or cooling and for an additional 7 hours on a hot water bath. The infrared spectrum reading shows no carboxylic acid absorption, indicating the reaction is complete.

The amount of isostearoyl chloride recovered is 709.

35g of the above isostearoyl chloride'e27.9
of hydrogenated chloramine, IIJ of triethylamine and 150 ml of methylene chloride.

The resulting N-tallow isostearamide was diluted twice with a 25% alcohol/water mixture, then with 25% ethanol and 50% ethanol.
Washed once with an aqueous solution containing rnl of concentrated HCl and again to neutrality with a 25% alcohol/water mixture, filtered and dried over Nα2S04.

Other aliphatic primary amines may be used in the preparation of the N-alkylisostearamide antistatic agents of the present invention, such as saturated or unsaturated ethyl, butyl, hexyl, nonyl,
Tesyl, dodecyl, tetradecyl, hexadecyl, heptadecyl and octadecylamine and mixtures thereof.

Secondary amines such as N,N-dimethylamine, such as N,N-diethylisostearamide, have a very limited effect on static electricity compared to the secondary isostearamide of the present invention. This produces a tertiary isostearamide.

Isostearamides of amines ranging from heptyl to octadecyl, alamides are superior to those with shorter chains, isostearamide 8 is NTA, =1. . 11. A)) It is effective in detergents using tripolyphosphate as a builder, and there is no significant deterioration in detergent properties.

It has further been discovered that there is no adverse effect on the deposition of optical brighteners. The N-alkylisostearamides of this invention perform equally well in bilge-containing and builder-free detergent systems.

The antistatic compounds of the present invention may be used in conjunction with anionic detergents such as alkylbenzenesulfonic acids and their salts. For example, alkyl is a C8 to C alkyl group, preferably a C to C18 alkyl group. is hydrogen or an alkali metal, the formula alkylphenyl-8o3-M
The compound consists of the well-known classes of anionic detergents, including sodium dodecylbenzenesulfonate, potassium todecylbenzenesulfonate, sodium laurylbenzenesulfonate, and sodium cetylbenzenesulfonate. include. Other things are
paraphytes sulfonates, alkyl sulfates, alcohol ether sulfates, olefin sulfonates and alkylphenol ethoxylate sulfates (e.g. EVA, sodium dinonylphenoxynonaethoxyethanol sulfate, sodium dodecyl hexadecaethoxyethanol sulfate), and other equivalent water-soluble salts. , especially those of the alkali metal series.

Among the alkylbenzenesulfonic acids and salts thereof mentioned above, preferred compounds include those characterized by biodegradable, 6D and especially linear alkyl substituents from C1o to 02°, preferably from C1° to C15. Of course, it is understood that this carbon chain length generally indicates the average chain length. This is because processes for producing products of this type usually use alkylating agents of mixed chain length. However, substantially pure olefins and alkylation compounds used in other techniques have alkyl moieties of substantially (e.g., at least 99%) one chain length;
That is, C1□, C□3. It is clear that alkylated benzene sulfonates can and do be provided when C14 or C15. Linear alkylbenzene sulfonates are further characterized by the position of the benzene ring in the linear alkyl chain, with either positional isomers (ie, alpha to omega) being operable and within consideration.

Benzene sulfonate, toluene, xylene,
Lower alkyl of benzene (C□
to C4) The homologous sequence t- may be used. These sulfonates are generally used in the form of water-soluble salts and include alkali metal, ammonium and lower amine, and alkanolamine cations as cations.

Examples of suitable linear alkylbenzene sulfonates are sodium n-tethylbenzene sulfonate sodium n-to9-decylbenzene sulfonate sodium
Sodium n-tetradecylbenzenesulfonate n
-d Sodium tadecylbenzenesulfonate n-
Hexadecylbenzene sulfonate, including the corresponding lower alkyl-substituted benzene congeners, as well as salts of the cations mentioned above. Of course, mixtures of these sulfonates can be used if the straight alkyl chains have an average chain length of 000 in the mixture.
Mixtures containing shorter or longer compounds than those shown here may be used, as long as they meet the specific needs of C2 to C2.

Straight-chain paraffin sulfonates are also a well-known group of compounds, including: 2-decanesulfonic acid 2-dodecanesulfonic acid 2-tridecanesulfonic acid 2-tetradecanesulfonic acid 2-pentadecanesulfonic acid 2-hexadecanesulfonic acid Includes salts (alkali metal, amine, vulcanolamine, and ammonium), as well as other regioisomers of sulfonic groups.

In addition to the above-mentioned Nomurafuin sulfonate, Cto
Others with a general range of gamma ruxi from `` to C2□ may also be used, with the most preferred being C1
It ranges from □ to C2o.

The straight chain alkyl sulfates contemplated in this invention range from C1o to C2o. A specific example is ■−
Sodium decyl sulfate, sodium n-dodecyl sulfate,
sodium n-hexadecyl sulfate, sodium n-heptadecyl sulfate, sodium n-octadecyl sulfate, and ethoxylated (1 to 100 ethylene oxide molecules) derivatives, and of course the other water-soluble salt-forming cations mentioned above. include.

Among the anionic detergents mentioned above as suitable in the present invention are olefin sulfonates, including long chain alkenesulfonates, long chain human 90-xy alkanesulfonates, as well as disulfonates. Examples of suitable olefin sulfonates are, but are only illustrative of the general class, sodium to8decene-1 sulfonate, sodium tetradecene-1 sulfonate, sodium hexadecene-1 sulfonate, and sodium octadecene-1 sulfonate. be.

Useful in conjunction with the antistatic secondary isostearamides 8 of the present invention are nonionic detergents, which are commercially known and include primary aliphatic alcohol ethoxylates, secondary aliphatic alcohol ethoxylates, Alcohol ethoxylates, alkylphenol ethoxylates, and Plurafax (
ethylene oxide-propylene oxide condensate, and mixtures thereof. Nonionic synthetic organic detergents are generally condensation products of organic aliphatic or alkyl aromatic hydrocarbon compounds and hydrophilic ethylene oxide groups.

In practice, carboxy group, human 90x group, amide 9
or a hydrophobic compound having an amino group with a free hydrogen attached to the nitrogen can be condensed with ethylene oxide 9 or its polyhydration product, polyethylene glycol, to form an anionic detergent. Additionally, the length of the polyethenoxy chains can be adjusted to achieve the desired balance between hydrophilic and hydrophobic elements.

Nonionic detergents are polyethylene oxide condensates of 1 mole of alkylphenols containing from 6 to 12 carbon atoms in linear or branched form and about 3 to 30 moles of ethylene oxide, e.g. 9 moles. nonylphenol condensed with ethylene oxide 9, todecylphenol condensed with 15 moles of ethylene oxide 9, and dinonylphenol condensed with 15 moles of ethylene oxide. Condensation products of the corresponding alkylthiophenols with 5 to 30 mol of ethylene oxide are also suitable.

Also included in the class of nonionic detergents is the condensation of higher alcohols (e.g., alkanols containing about 8 to 18 carbon atoms in a straight or branched chain form) with about 5 to 30 moles of ethylene oxide. Also included are products, e.g., about 1
It is lauryl-myristyl alcohol condensed with 6 moles of ethylene oxide 9.

A preferred group of nonionic surfactants are neodol ethoxylates (Shell), which contain about 5 to 20 ethyleneoxy groups per mole of aliphatic alcohol containing about 10 to 18 carbon atoms. A higher aliphatic alcohol ethoxylate having, for example, a C alcohol condensed with 6.5 moles of ethylene oxide, a C alcohol condensed with 12 moles of ethylene oxide, 13
moles of ethylene oxide, condensed C14-15 alkanol, etc.

In addition to anionic and nonionic detergents that may be used with the antistatic agents of this invention, amphoteric compounds may also be useful. Representative of those compounds that may be used with the textile antistatic compounds of this invention include carboxy- and sulfo-betaines.

The amount of detergent will range from about 5-75%, usually about 15-45% by weight of the total composition.

The compositions of the invention can also be combined with the antistatic compounds of the invention and conventional anionic, nonionic and amphoteric detergents.
ka′・1″′-・brightener・l:)”Cff
, Trope, Bactericide, Antioxidant, Bleach 1 Colorant (
dyes and pigments), fragrances, water-soluble alcohols, suds enhancers, non-detergent alkyl metal benzene sulfonates, and the like.

Builders are generally water-soluble inorganic salts, such as neutral salts such as sodium sulfate or phosphates, silicates, bicarbonates, carbonates, citrates and borates. It is an alkaline builder. Preferred builders are those characterized as condensed phosphates such as polyphosphates and 20phosphates and alkali citrates. Specific examples of alkaline salts are tripolyphosphate, tetrasodium pyrophosphate, pentasodium tripolyphosphate (phase 1
``! or both), sodium hexametaphosphate, and the corresponding potassium salts of these compounds, sodium and potassium silicates, such as sodium metasilicate and other silicates (e.g., Na2O: 1.'6-35102
), sodium carbonate, carbonate, potassium, and sodium and potassium bicarbonate, sodium citrate and potassium citrate. Other salts may also be used, provided that the compounds are water soluble, including the common classes of alkali metal, alkaline earth metal, amine, alkanolamine, and ammonium salts.

Other builders that are organic acid salts may also be used, and in particular: ethylenediaminetetraacetic acid nitrilotriacetic acid diethylenetriaminepentaacetic acid N-(2-hydroxyethyl)-ethylenediaminetetraacetic acid 2-hydroxyethyliminodiacetic acid 1. Dilute with a water-soluble (substituted ammonium and amine) salt of an aminopolycarboxylic acid such as 2-diaminocyclohexane diacetic acid.

Sodium aluminosilicate, such as Zeolite A.

Water-insoluble builders with cation exchange properties may also be used, such as those used alone or in combination with other builders such as sodium tripolyphosphate.

The amount of builder salts comprises 5-75% by weight of the total composition, which may be in liquid or solid form, and is usually about 20-70% by weight of the total composition.
It changes depending on the weight.

N of the invention in combination with detergents and conventional laundry additives
It will be appreciated that in addition to the composition comprising the alkyl isostearamide antistatic agent, it may be formulated in a suitable adsorbent carrier for co-addition with the detergent material to the wash cycle of the laundry process. In that regard, the above-mentioned amide 9 may be dispersed in or adsorbed onto an adsorbent carrier for addition to the laundry cycle, which carrier may be, for example, phosphate, borax, Microcell C (by Johns Manville). 14. Synthetic calcium silicate), bentonite clay such as the former Chikunjiel Bane 1 mineral colloid 101 (Jossia Kaolin Co.), 37.5% tripolyphosphate and 14.
Phosphate-based bead consisting of 5% sodium silicate and spray-dried phosphorus-salt-based bead with dye and water, or 49% sodium bicarbonate, 10.67% sodium carbonate, and 17% silicate solids. A carbonate-based bead consisting of water, colorant, and water. These beads contain isostearamide 9 in liquid or molten form (if solid).
and mix until this amide is dispersed or absorbed into these base beats 9.

The amount of amide 9 used with detergent compositions will generally be relatively small compared to the weight of the active ingredients therein. However, it is recognized that only an effective amount of the above amines needs to be used that actually produces the desired antistatic effect on the fabric. The above-mentioned amides are such that the concentration in the washing solution is in the range of 0.002-0.02%.
From about 2 parts to about 25%, by weight, of the total ingredients present in the detergent composition.

Preferably it is present in an amount of 5% to 20%. Increasing the amount of amide 9 reduces static electricity generated on the fabric during tumble drying or wearing.

The compositions of the present invention may be used in granular, liquid, tablet, or any other conventional form.

Moreover, the above-mentioned rules, the rules disclosed herein,
Secondary isostearamide is used for cleaning during the washing process.
It may be used as an antistatic textile agent by application to textiles during the washing cycle, or it may be premixed with detergent substances.

Laundry compositions and antistatic compositions of the present invention.

The methods of treating textiles therewith as well as the methods thereof are illustrated herein by more detailed examples below. However, it is recognized that these examples are merely illustrative of the invention and are not intended to be limiting.

Add 20 grams of Neodol 23-6.5 to the washer while it contains 120°F (49°C) 651 water. After 1 minute, 3 g of isostearamide is added. After another minute, four types of fabrics, Dacron (D), Nylon (Foundation), Dacron-cotton (D/C) and Acede
), (Ac) were added. The fabric was washed for 14 minutes, rinsed with cold water, and tumble dried.

A qualitative measure of the antistatic properties imparted to the fabric is the presence or absence of static electricity/entanglement when removed from the dryer. A good quantitative measure can be obtained by measuring the charge in kilovolts developed on each fabric when the fabric is rubbed with wool for 5 seconds at low humidity; the sum of the absolute values of the charges on each fabric. is a convenient measure of antistatic properties; the lower the number, the better N-octyl isostearamide is the best of the four. The least effective is diethyl isostearamide 9.

(tlE) 1. Ethoxylated C1°-13 aliphatic alcohol with an average of 6.5 moles of ethylene oxide (Shell) These results demonstrate that ethoxylated C1-13 aliphatic alcohols with an average of 6.5 moles of ethylene oxide can be used as high-grade antistatic agents in cleaning cycles during cleaning with non-ionic detergents without builders. This shows that the lower alkyl isostearamide (chain with 8 carbon atoms) is superior to the lower alkyl isostearamide 9. This tertiary isostearamide, diethyl isostearamide, has minimal antistatic activity.

The Dacron pickup value indicates the substantivity of Ami type 1 to textiles.

Examples 10-13 The procedure of Examples 6-9 is repeated with octyl isostearamide in the presence and absence of 30 g of tripolyphosphate sodium salt (Examples 10 and 11), and the salt is washed in a washing machine. Also added to the washer along with Neodol detergent during wash fill.

Isostearamide is a builder-free system and IJ
It worked equally well in systems containing 41J phosphate builder.

Sodium tridecylbenzenesulfonate 15
Non-ionic detergent 3. 5 Sodium silicate (1:2.4) 10.5 Sodium tripolyphosphate 33 Sodium carbonate
5 Sodium sulfate
24 Sodium Carboxymethyl Cellulose
, 25 optical brightener
, 5. Sand 1.
0 fragrance, 1
5 water 10
．． 1 - Aliphatic alcohol with an average of 7 moles of ethylene oxide (C1□-C□5) Example 15° This composition may be modified to reduce the phosphate content with 20% zeolite.

Example 16 The composition of Example 14 contains all 20 parts of thixo gel (clay) and may be modified to reduce the amount of phosphate.

Example 17° Composition of Example 15 in which the phosphate builder was replaced with a nitrilotriacetate salt.

Example 18 The composition of Example 14 may be modified to replace the phosphate builder with sodium carbonate.

These compositions were spray dried to form powders.

Add 2-10 g of amide antistatic agent to each composition and then premix by suitable means using rotation and/or stirring, with or without heating.

a, N-decyl isostearamide b, N-octyl isostearamide c, N-cocoisostearamide d, N-tallow isostearamide.

Examples 19 and 20 a, b + c- and d ethoxylated alcohols Sodium tripolyphosphate 6° Sodium silicate (1:2.4) 10 Optical brightener 2 Enzyme (proteolytic) 1
．． 5 Fragrances and Colorants 0.35 Moisture
7.15 Example 20 The composition of Example 19 may be modified to replace a portion of the tripolyphosphate with sodium nitrilotriacetate salt.

Add 2-10 g of textile antistatic agent to 4 l of this formulation in powder form.

a. N-decyl isostearamide b. N-octyl isostearamide c. N-cocoisostearamide d. Condensed aliphatic alcohol (C12-C13).

Ethoxylated alcohol 34.0 Dotecylbenzenesulfo*-) 8.5 Ethanol, 6.5 Triethanolamine 0.5 Sodium formate 1.5 Fragrance 0.5 Optical brightener 0.6 Colorant
0.3 moisture 4
7.6 - Aliphatic alcohol (C1□-15) condensed with an average of 6.5 moles of ethylene oxide.

When using 60g of this liquid composition in a washing machine,
2-101! An antistatic agent was also added.

a, N-decyl isostearamide
H1b, N-octyl isostearamide c, N-cocoisostearamide d, N-tallow isostearamide Example 22 Antistatic on anionic laundry detergents containing representative tripolyphosphate builders The effectiveness of N-decyl isostearamide as an agent has been demonstrated in mixed textile loadings (polyester, nylon, acetate and polyester-cotton blends) of 0.2.4. or by washing in 100 Example 14a (whirlpool washer, 120°F (4
9°C), 651 tap water). Antistatic properties were quantified by measuring the charge developed by combining each dry fabric with wool in a controlled manner for 5 minutes. The absolute types of these charges are summed to obtain the electrostatic value. The smaller the number, the greater the antistatic property. Showing the results of two experiments.

Static electricity value Q of decyl isosteanogenide (
37.332
17.174 10.
116 7 , 7 This example clearly demonstrates the antistatic properties of the secondary isostearamides of the present invention at levels as low as about 2% by weight of the detergent composition, with increasing amounts of amide occurring. Reduces static electricity.

The utility of amides in reducing static electricity is shown in Table 1 in Table 1.
5) at 120'F (49°C) in a whirlpool washer (tap water 651) and tumble dry. In each case, 6-3 g of test substance was added to 95-100.9 of anionic detergent or 40 II
of non-ionic detergent and then added to the wash cycle of the laundry process.

The static electricity value is the sum of the absolute values of the surface charges of the four fabrics when taken out from the dryer; the lower the value, the better.

1st Table 23 Example 14 Yes 4
3,4024 Example 14 3g Decyl None 1125 Example 14 3g Coco None 1426 Example 14 6g Coco None 727 Example 14 3g Tallow None 1328 Example 14 6g Tallow None 1529 Example 15
Yes 4730 Example 16
Yes 59, 4731 Example 15 5g
Coco None 1032 Example 16 5I
Coco None 2733 Example 14 5g
Octyl None 93X Example 15 5g
Octyl None 635 Example 16 4g
Octyl None 2336″ Example 16 4
g Coco None 19'374 Example 1
6 6g Octyl None 1938 Example 1
6 6g Coco None 1439 Example 1
4 4g Coco 'No 1240'' Example 1
6 4g Coco None 2641 Example 15 4g Coco None 134t Example 17 4g Coco None 1943" Example 14 4I Coco None 1444" Example 1j 4.9 Octyl None 1345
Example 19--1 Yes 4246
Example 19 3g Coco None 2547
Example 19 5g Coco None 2448
Example 19 5. li' taro nothing
15 (in table) 4 This stearinamide spreads evenly over the inner surface of the 21 flask. Add detergent to the flask and rotate in a hot water bath. The flask walls are scraped once and the mixture is spun again until all of the isostearamide is dispersed to provide a more uniform dispersion.

4g of isostearamide is dispersed with 94g of detergent without heating.

Octyl, decyl, coco and tallow isostearamides premixed with nonionic or anionic detergents containing builders are all effective antistatic agents.

By incorporating bentonite clay as well as isostearamide into phosphate builder-containing anionic detergents, the fabric softening effect of the former is obtained together with the antistatic effect of the latter (Example 32.35°36, 37.38 and 40).

The particular detergent composition used influences the antistatic properties of isostearamide, with both phosphate builder-containing anionic detergents and phosphate-zeolide builder-containing anionic detergents being nitrilotria.

This nitrilotriacetate-containing detergent is more effective than the phosphate/thixo gel anionic activator (Example 3).
9-42). Isostearamide dispersed in builder-containing nonionic detergents has reduced antistatic effectiveness due to apparent inactivation due to intimate contact with nonionic surfactants (Examples 46, 47 and 48).

The isostearamide may be added as such or may be dispersed and/or absorbed in a suitable absorbent such as phosphate-based beads, Microcell C, fabrics such as terry towels, Alternatively, it may be distributed on the surface of granular detergent.

Table 1 shows 51 antistatic agents on various substrates placed in a washing machine.
The results are shown when it was added separately at the same time as the 00I detergent.

Table 50 Example 18 Coco ioy phosphate
12 Base Bead 51 Example 14 Coco 8.8g Towel Piece 1052 Example 14 Taro
8.8S towel piece 1053 Example 14
Coco 10. F phosphate 14 base beet 54 Example 14 Tallow 10g phosphate
12 Base Bead 55 Example 14 Coco 4/I Microcell C956 Example 14 Taro 49 Microcell C1557 Example 14 Coco 10.9
Detergent 1358 Example 14 Tallow 10F detergent 1759'40!9 Example 19
Coco 4g Microcell C156040 & Example 20 Coco 3g Microcell C1361
Example 18 Coco 3g Microcell CI2
62 60P Example 21 Coco 3g Microcell C15 Infrared analysis of the material deposited on the Dacron fabric during washing and recovered by ether extraction shows that it is only cocoisostearamide.

Therefore, cocoisostearamide does not cause co-deposition of surfactants.

Cocoisostearamide does not interfere with detergent properties using standard stained fabric swatches (Test Fabric Nylon, Test Fabric Cotton, Clay on Cotton, Polyester-Clay on Cotton, EMPAlol).
) in a total of 100.9 anionic detergents (Example 14),
4-5. ! This was demonstrated by washing with and without the addition of 5 g of cocoisostearamide absorbed onto Microcell C of i+.

Other carriers or substrates that are useful for the isostearamide include borax, soda ash, granular polyphosphoric acid, preferably at a weight ratio of about 1-5 g of isostearamide to 1.5-1.0,@ of the substrate. 3) Contains IJum, granular sodium pyrophosphate and other suitable absorbent carriers.

The manner in which isostearamide is incorporated into detergents influences the antistatic results. This accounts for variation in performance between experiments using the same components. A preferred form is Microcell C (Isostearamide 9 dispersed on synthetic calcium silicate) as a separate additive to the washing machine during the wash cycle of the laundry process.

Using concentrations of 7.5 to 240 ppm, the compounds of the present invention have no significant effect on the overall detergent properties of stained specimen fabrics, do not reduce the brightener effect, and are effective in the field of nylon or nylon yellowing. No significant yellowing occurs compared to an equivalent weight of quaternary ammonium type antistatic agent which has defects.

The ability of secondary N-alkylisostearamides, with and without builders, to reduce static electricity in the presence of both anionic and nonionic detergents and mixtures thereof was demonstrated in compositions 14-21. This is clearly shown below.

It is understood that the foregoing detailed description is given for illustrative purposes only and that changes may be made without departing from the spirit of the invention. The foregoing "Abstract" is for the convenience of technical exploration only and does not give any flavor as to the scope of the present invention.

Patent applicant: Colgate-Palmolive Company (removed name)

Claims (1)

Claims: 1. having the formula RCONHR', where RCO is derived from isostearic acid and R' is a primary saturated or unsaturated fatty acid hydrocarbon chain containing 1-18 carbons; N
-Alkyl-isostearamide antistatic agents. 2. A compound according to claim 1, wherein the primary fatty chain contains 7-18 carbons. 3. The compound according to claim 2, which is cocoalkyl isostearamide. 4. The compound according to claim 2, which is hydrogenated tallow isostearamide. 5. The compound according to claim 2, which is decyl isostearamide. 6. A textile comprising an effective antistatic amount of an isostearamide antistatic agent according to claim 1 and a detergent selected from the group consisting of anionic, nonionic and amphoteric detergent materials. Antistatic composition for laundry. 7. An antistatic composition for textile laundry, comprising about 2-25% by weight of an amide antistatic agent according to claim 1 and a nonionic detergent. 8. The composition of claim 7 further comprising an optical brightener and a builder. 9. The composition of claim 6, wherein the detergent is anionic and the antistatic agent comprises about 2-25% by weight of the composition. 10. The composition of claim 9 further comprising an optical brightener and a builder. 11. Dispersed in an absorbent substrate; Claim 1
An antistatic composition for use in the washing cycle of textile laundering, comprising an antistatically effective amount of an isostearamide antistatic agent according to paragraph 1. 12. The antistatic composition according to claim 11, wherein the substrate is a synthetic calcium silicate. 13. The antistatic composition of claim 11, wherein the substrate is a phosphate-based bead consisting of tripolyphosphate solids and sodium silicate solids. 14. A method of protecting textiles against electrostatic charging during the washing process, comprising contacting the textile with a composition according to claim 6. 15. A method for imparting antistatic properties to textiles, comprising treating the textiles with a composition according to claim 11 during washing. 16. Washing textiles in a detergent composition comprising an anionic, nonionic surfactant or a mixture thereof premixed with an antistatic isostearamide according to claim 1. Claim 1 consisting of
The method described in Section 5. 17. The method of claim 15, wherein the antistatic isostearamide agent is added separately during the wash cycle.