JPH07268388A - Detergent composition containing nonionic glycolipid surfactant - Google Patents

Abstract

PURPOSE: To provide the subject detergent composition comprising an aldobionamide as a nonionic glycolipid surfactant which is environmentally friendly and suitable for cleaning fibers, textiles and hard surfaces.

CONSTITUTION: There is provided the aimed composition comprising, as a nonionic glycolipid surfactant, an aldobionamide [preferably an aldobionamide of the formula (wherein R₁ and R₂ are each H, an aliphatic hydrocarbon, an aromatic residue, an alicyclic residue, an amono acid ester or an ether amine with the proviso that R₁ and R₂ are not both H simultaneously)]. N- tetradecyllactobionamide, for example, is prepared by adding molten tetradecylamine to lactobiono-1,5-lactone as a starting material in a methanol solvent thereby causing to react together and subsequently cooling to obtain a crystal followed by isolation by recrystallization from methanol.

COPYRIGHT: (C)1995,JPO

Description

Detailed Description of the Invention

The present invention relates to novel detergent compositions suitable for cleaning fibers (woven and knitted fabrics) and hard surfaces. The composition of the present invention comprises a glycolipid surfactant, in particular a nonionic aldobionamide as the surfactant.

Aldionamide is defined as the amide of aldobionic acid (or aldobionolactone), which is a sugar substance in which the aldehyde group (generally at the C1 position of the sugar) is replaced by a carboxylic acid ( For example, a cyclic saccharide). Aldonamides may be based on compounds containing one saccharide sugar unit (eg gluconamide) or two saccharide units (eg lactobionamide or maltobionamide), or more than two saccharide units. And a compound having an aldehyde group that can utilize the terminal sugar of the polysaccharide. However, there must be at least 2 saccharide units. Because these substances are less densely packed in the solid state, they are more water soluble than chain saccharides (eg gluconamide or glucoheptonamide) and can make stable compositions. Is.

Most surfactants currently used in detergent compositions are based on petrochemicals. Given the growing concern over the environmental problems caused by the use of petrochemicals and the continuing rise in prices of these petrochemicals, it is not possible to develop alternative carbohydrate-derived surfactants. Would be useful. These naturally occurring compounds represent a synthetically useful, inexpensive, optically pure, environmentally friendly and renewable source of raw materials.

US Pat. No. 2,752,334 (Walton) discloses compounds which are reactants of aldonic acids (eg lactobionic acid) and fatty amines. The compound is said to be useful as an emulsifier in food compositions.

Archives of Biochem. And Williams et al.
Biophysics, 195 (1): 145-151 (1979) describes glycolipids prepared by linking aldobionic acid to an alkylamine through an amide bond. Although these compounds are said to make micelles like all surfactants, there is no disclosure or suggestion of their use in detergent compositions.

USP5009814 is the following formula

[0007]

[Chemical 3]

[Wherein R ₁ is alkyl and R ₂ is
It is hydrogen, alkyl or alkyl hydroxide, and X is a polyhydroxy group. ] And N-polyhydroxyalkyl fatty acids used as thickeners in aqueous surfactant systems.

This is a completely different class of compound from the aldobionamides of the present invention. In the disclosed compounds, the polyhydroxy groups are separated by a methylene group attached to the nitrogen atom rather than a carbonyl group which results in an amide bond, which is the opposite of the compounds of the present invention. These compounds are obtained by the reaction of amines of monosaccharides (monosaccharides) and alkyl esters of fatty acids, while the aldobionamides of the invention are di (or larger).
It is obtained by the reaction of sugar lactones of saccharides with fatty amines.

In addition, there are a series of Procter and Gamble patent applications that disclose a number of compositions containing polyhydroxyamides. For example, WO09 / 06172A discloses a liquid detergent composition comprising a polyhydroxyamide.
There are at least 20 other patent applications that list various compositions containing similar polyhydroxyamides.

The polyhydroxyamides of each of these documents, like the compound of USP5009814, are completely different from the aldobionamides of the present invention. Again, the polyhydroxy groups in each case are separated by a methylene group attached to the nitrogen atom rather than a carbonyl group.

FR2523962 (Monsigny) has the formula:
HOCH ₂ (CHOH) _m CONHR [in the formula, m is 2 to
6 and R is a chain or branched alkyl group having 6 to 18 carbon atoms. ] Is disclosed.
These surfactants are stated to have low foaming and must be ethoxylated or propoxylated in a typical manner in order to achieve sufficient solubility.

The document does not disclose the aldobionamide of the present invention. In the solid state, aldobionamide is less densely packed than aldonamide, so it has greater solubility (lower Kraft point) and greater foaming. The document does not disclose or suggest the aldobionamides of the present invention as it discloses low foaming (indicating low solubility, high Kraft point), and in fact The disclosure is far from the invention.

It is therefore highly desirable to find carbohydrates, especially aldobionamides, which can be used well as surfactants in detergent compositions.

The present invention therefore provides a fiber (product) containing a nonionic glycolipid surfactant which is an aldobionamide.
Alternatively, a detergent composition suitable for cleaning hard surfaces is provided.

The aldobionamide according to the present invention is generally represented by the formula: ANR ₁ R ₂ [wherein A is an aldobionic acid except that it does not contain an OH group extending from the carbonyl group of a conventional aldobionic acid. NR ₁ R ₂ is
In the case of ordinary aldobionic acid, it is bonded to a place having a hydroxyl group; R ₁ and R ₂ may be the same or different, and hydrogen, an aliphatic hydrocarbon, an aromatic radical, an alicyclic radical, an amino acid ester, It is selected from the group consisting of ether amines and mixtures thereof. However, R ₁ and R ₂ do not become hydrogen at the same time. ].

The aldobionamide in the preferred composition of the present invention is one in which R is hydrogen and R ₁ is an alkyl group having 8 to 24 carbon atoms.

The preferred compound A is a disaccharide (disaccharide) residue, which forms a compound which is aldobionic acid except for the OH group.

The present invention relates to the use of personal product or detergent compositions containing environmentally friendly surfactants, in particular environmentally friendly nonionic surfactants such as aldobionamide.

Aldobionamide is defined as the amide of aldobionic acid (or aldobion lactone), which is a sugar substance in which the aldehyde group (generally at the C1 position of the sugar) is replaced by a carboxylic acid (eg, , A cyclic saccharide containing at least two saccharide units), which when dried cyclizes to an aldobion lactone.

The aldobionamide may be based on a compound containing two saccharide units (eg lactobionamide or maltobionamide via an aldbionamide bond) or it may contain more than two saccharide units, A compound in which the terminal sugar of the polysaccharide has an aldehyde group may be used as a base. By definition, an aldobionamide must contain at least 2 saccharide units and is not linear. Disaccharide compounds such as lactobionamide or maltobionamide are preferred. Examples of other aldobionamides (disaccharides) that can be used include cellobionamides, meribionamides and gentiobionamines.

A specific example of an aldobionamide that can be used for the purposes of the present invention is the disaccharide lactobionamide, shown below.

[0023]

[Chemical 4]

[Wherein R ₁ and R ₂ may be the same or different and are hydrogen; an aliphatic hydrocarbon radical (for example, an alkyl group or an alkene which may contain a hetero atom such as N, O or S). Group or an alkoxylated alkyl chain such as an ethoxylated or propoxylated alkyl group), preferably an alkyl group having 8 to 24 carbon atoms, more preferably 10 to 18 carbon atoms; aromatic radical (substituted or unsubstituted) Substituted aryl groups and arenes); alicyclic radicals; amino acid esters; ether amines and mixtures thereof. However, R ₁ and R ₂ do not become hydrogen at the same time. ] Another preferred aldobionamide is maltobionamide of the formula:

[0025]

[Chemical 5]

[Wherein R ₁ and R ₂ may be the same or different and are from the group consisting of hydrogen, aliphatic hydrocarbons, aromatic radicals, alicyclic radicals; amino acid esters, ether amines and mixtures thereof. To be selected. However, R ₁ and R ₂ do not become hydrogen at the same time. ] Suitable aliphatic hydrocarbon radicals include saturated and unsaturated radicals including methyl, ethyl, amyl, hexyl, heptyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl,
Examples include, but are not limited to, heptadecyl and octadecyl, and allyl, undecenyl, oleyl, linoleyl, linolenyl, propenyl and heptenyl.

Examples of aromatic radicals include benzyl.

Examples of suitable aliphatic-aromatic mixed radicals include benzyl, phenylethyl and vinylbenzyl.

Examples of cycloaliphatic radicals include cyclopentyl and cyclohexyl.

The aldobionamides used in the composition of the present invention are based on other known nonionic surfactants based on petrochemicals (eg Neodol ™, Shell.
It has been found that it has properties equal to or better than those of the (alkoxylated surfactants) of (manufacturing) series (that is, critical micelle concentration, Kraft point, foaming, and cleaning property). This means that the aldobionamide is a useful, environmentally friendly alternative to conventional nonionic surfactants.

Without wishing to be bound by theory, it is believed that the lower solubility of aldobionamide is due to the sugar structure. The structure does not result in the dense packing as found in linear monosaccharide aldonamides such as gluconamide. It is also believed that the higher number of hydroxyl groups probably helps to increase the solubility of aldobionamide.

Also, the surfactants of the present invention may be used in combination with other nonionic surfactants, especially ethoxylated alcohol nonionic surfactants, or other surfactants (eg, cations) used in detergent compositions. And anionic, zwitterionic, amphoteric) as cosurfactant.

Detergent Compositions Aldionionamide surfactants can be used in fabric or hard surface cleaning or detergent compositions.

An example of a liquid detergent composition is USP 49591.
79 (Aronson et al.), Which is hereby incorporated by reference. Examples of powder detergent compositions are described in USP 4,929,379 (Oldenburg et al.), Which is also incorporated herein by reference.

The liquid detergent composition of the present invention may or may not contain a builder, and may or may not be aqueous. The composition generally comprises about 5-70% by weight.
Detergent actives and 0 to 50% by weight builder. The liquid detergent composition of the present invention further comprises an amount of electrolyte (defined as a water-soluble salt), the amount of which depends on whether the composition is structured or not. Structuring the composition means forming a lamellar phase sufficient to impart solid suspending ability.

The unstructured, non-suspendable composition does not require an electrolyte, but in particular at least 1% by weight, more preferably at least 5% by weight and most preferably at least 15% by weight electrolyte. use. Formation of the lamellar phase can be detected by methods well known to those skilled in the art.

The water-soluble electrolyte salt may be a detergent builder such as sodium tripolyphosphate inorganic salt, or a non-functional electrolyte such as sodium sulfate or sodium chloride. Preferably, whatever builder is used in the composition, it is preferred that the builder comprises all or part of the electrolyte.

In general, the liquid detergent composition further comprises enzymes such as proteases, lipases, amylases and cellulases, which, when present, are present in the composition.
Used in an amount of 01-5%. Stabilizers or systems may be used with the enzyme, the amount generally being 0.1 to 15% by weight of the composition.

The enzyme stabilizing system comprises calcium ions, boric acid, propylene glycol and / or short chain carboxylic acids. Preferably, the composition comprises 0.01 to 50 millimoles, preferably 0.1 to 30 millimoles, more preferably 1 to 20 millimoles of calcium ions per liter.

If calcium ions are used, the amount of calcium ions is chosen such that there is always some minimum amount available in the composition for the enzyme after complexing with the builders and the like. Any water-soluble calcium salt can be used as a source of calcium ions, such as calcium chloride, calcium formate, calcium acetate and calcium propionate. The amount of calcium ions is small, generally 0.1 per liter, because calcium is present in the enzyme slurry and composition water.
It is often from 05 to 2.5 mmol.

Another enzyme stabilizer that can be used is propionic acid or a propionic acid salt capable of forming propionic acid. If used, this stabilizer may be used in an amount of 0.1-1 of the composition.
Used in an amount of 5% by weight.

Other preferred enzyme stabilizers are polyols containing only carbon, hydrogen and oxygen atoms, preferably containing 2 to 6 carbon atoms and 2 to 6 hydroxyl groups.
Examples include propylene glycol (particularly preferred is 1,2-propanediol), ethylene glycol, glycerol, sorbitol, mannitol and glucose. The amount of polyol is generally 0.5 to 15% by weight of the composition, preferably 1.0 to
8% by weight.

The composition of the present invention may also, if desired,
0.25-5% by weight, more preferably 0.5-3% by weight
Boric acid may be included. Although not preferred, boric acid may be a compound capable of forming boric acid in the composition. Boric acid is preferred, but other compounds such as boron oxide, borax and other alkali metal borates (eg sodium orthoborate, sodium metaborate, sodium pyroborate and sodium pentaborate) are also suitable. Further, boric acid having a substituent (for example, phenyl boric acid,
Butane boric acid and p-bromophenyl boric acid) can also be used instead of boric acid.

A particularly preferred stable system is a combination of a polyol and boric acid. Preferably, the weight ratio of added polyol to boric acid is at least 1, more preferably at least about 1.3.

With respect to the cleaning actives, the cleaning actives are
It may be an alkali metal or alkanolamine soap or a fatty acid having 10 to 24 carbon atoms including a polymerized fatty acid, or an anionic, nonionic, cationic, amphoteric or amphoteric synthetic detergent substance or the like. It may be a mixture of.

Examples of the anionic synthetic detergent include alkylbenzenesulfonic acid having 9 to 20 carbon atoms and 8 to 8 carbon atoms.
22 first or second alkane sulfonic acid having 8 to 8 carbon atoms
24 olefin sulphonic acids, sulphonated polycarboxylic acids prepared by sulphonation of pyrolysates of alkaline earth metal citrates (eg GB1082179).
, C8-22 alkyl sulfonic acid, C8-24 alkyl polyglycol-ether-sulfonic acid, -carboxylic acid and -phosphoric acid (containing up to 10 mol of ethylene oxide) salts (for example, sodium,
Salts of potassium, ammonium and substituted ammonium (such as mono-, di- and triethanolamine) are included. Yet another example is “Surface Active Agents
andDetergents ”(vol. I and II) by Schwarts, Perry
and Berch. Any suitable anionic can be used and is not limited to the above examples.

Examples of non-ionic synthetic detergents which can be used in the present invention include ethylene oxide, propylene oxide and / or various similar oxides with 8 to 18 carbon atoms.
Alkylphenol, a condensation substance with a fatty acid amide having 8 to 18 carbon atoms, and a nonionic one having an alkyl chain having 8 to 18 carbon atoms and two alkyl chains having 1 to 3 carbon atoms. Triamine oxide may be mentioned. Still another example is described in the above document.

The average number of moles of ethylene oxide and / or propylene oxide present in the above-mentioned nonionic substance is 1 to 30. Mixtures of various nonionics can also be used, for example mixtures of low alkoxylation nonionics and high nonionics.

Examples of cationic detergents that can be used are:
Quaternary ammonium compounds such as alkyl dimethyl ammonium halides.

Examples of amphoteric or zwitterionic detergents which can be used in the present invention include N-alkylamine acids, sulfobetaines, and condensation products of fatty acids and protein hydrolysates, which are relatively expensive. , Usually in combination with anionic or nonionic detergents. Mixtures of different active detergents can also be used, preference being given to mixtures of anionic and nonionic detergent activators. Soaps of fatty acids (sodium, potassium and substituted ammonium salts) can also be used, preferably with anionic and / or nonionic synthetic detergents.

The builders which can be used in the present invention include ordinary alkaline detergent builders (inorganic or organic),
0-50% by weight of the composition, preferably 1-20% by weight,
Most preferably it can be used in an amount of 2 to 8% by weight.

Examples of suitable inorganic alkaline detergent builders include the water-soluble alkali metal salts of phosphoric acid, polyphosphoric acid, boric acid, silicic acid and carbonic acid. Specific examples of such salts include the sodium and potassium salts of triphosphoric acid, pyrophosphoric acid, orthophosphoric acid, hexametaphosphoric acid, tetraboric acid, silicic acid and carbonic acid.

Examples of suitable organic alkaline detergent builders include (1) water-soluble aminopolycarboxylates, such as the sodium and potassium salts of ethylenediaminetetraacetic acid, nitrilotriacetic acid and N- (2-hydroxyethyl) nitrilodiacetic acid; (2) Water-soluble salts of phytic acid, such as sodium phytate and potassium phytate (see USP 2379942); (3) Water-soluble polyphosphonates, especially sodium ethane-1-hydroxy-1,1-diphosphonate. Potassium and lithium salts; sodium, potassium and lithium salts of methylenediphosphonic acid; sodium, potassium and lithium salts of ethane-1,1,2-triphosphonic acid; ethane-2-carboxy-1,1-diphosphonic acid, hydroxymethane Diphospho Acid, carboxyl diphosphonic acid,
Ethane-1-hydroxy-1,1,2-triphosphonic acid, ethane-2-hydroxy-1,1,2-triphosphonic acid, propane-1,1,3,3-tetraphosphonic acid,
Propane-1,1,2,3-tetraphosphonic acid and alkali metal salts of propane-1,2,2,3-tetraphosphonic acid; (4) of polycarboxylate polymers and copolymers as described in USP 3308067. Water-soluble salts are mentioned.

Polycarboxylic acid salt builders can also be used satisfactorily, and examples thereof include water-soluble salts of mellitic acid, citric acid and carboxymethyloxysuccinic acid, and salts of polymers of itaconic acid and maleic acid. Other polycarboxylate builders include DPA
(Dipicolinic acid) and ODS (oxydisuccinic acid). Certain zeolites or aluminosilicates can also be used. One of the aluminosilicates useful in the composition of the present invention is the formula: Na _x (AlO ₂ .SiO ₂ ) _y , where x
Is 1.0 to 1.2 and y is 1. ] The amorphous water-insoluble hydrated compound of
g ⁺⁺ ion exchange capacity is about 50mg equivalents CaCO ₃ / g, and wherein the particle sizes of 0.01 to 5 microns. About this ion exchange builder, GB1470
250 (Procter & Gamble).

Another water insoluble synthetic aluminosilicate ion exchange material useful in the present invention exists in crystalline form,
Formula: Na _z [(AlO ₂ ) _y · (SiO ₂ )] · xH ₂
O [wherein z and y are integers of at least 6;
The molar ratio of y to y is in the range of 1.0 to 0.5 and x is 1
It is an integer of 5 to 264. ]. The aluminosilicate ion exchange material has a particle size of 0.1 to 100 microns, a calcium ion exchange capacity for an anhydride of at least 200 mg equivalent CaCO ₃ / g, and a calcium exchange rate for an anhydride of at least 2 grains / g. Gallons / minute / g. These synthetic aluminosilicates are more fully described in GB 1429143 (Procter & Gamble).

In addition to the components described above, the preferred compositions of the present invention often include a series of optional components, which are used in conventional amounts in known amounts. Detergent compositions are generally based on aqueous enzyme-containing detergent compositions, although it is often desirable to use phase modifiers. This component, together with water, constitutes the solvent matrix of the liquid composition defined in the claims. Suitable phase regulators are well known in the liquid detergent art, for example alkylaryl sulfonates having an alkyl group of up to 3 carbon atoms (eg xylene sulfonic acid, toluene sulfonic acid,
Representative examples are hydrotropes such as ethylbenzene sulfonic acid, cumene sulfonic acid and sodium, potassium, ammonium and ethanolamine salts of isopropylbenzene sulfonic acid. Alcohol can also be used as a phase modifier. This phase modifier is often used in an amount of 0.5 to 20% by weight, and the sum of the phase modifier and water is usually 35 to 65% by weight.

The preferred compositions of the present invention may further comprise a series of optional ingredients, often in added amounts (usually up to 5% by weight). Examples of such additives include polyacids, foam control agents, emulsifiers, antioxidants, bactericides, dyes, fragrances, brighteners and the like.

A foam control agent may be utilized to beneficially utilize the claimed composition under various conditions of use. In general, any detergent foam control agent can be used, but preferred for use in the present invention are alkylated polysiloxanes such as dimethyl polysiloxane (often referred to as silicone). Silicones are often used in amounts not exceeding 0.5% by weight, most preferably 0.01-0.2% by weight.

It may also be desirable to use an emulsifier to the extent that it contributes to a uniform appearance of the concentrated liquid detergent composition. Examples of suitable emulsifiers include LYT
RON (trademark) 621 (Monsanto Chemical Corporatio
There are known polystyrenes commercially available as (n. Emulsifiers are often used in amounts of 0.3 to 1.5% by weight.

The compositions of the present invention may also have an art-established amount for known uses (often radical scavengers) (ie 0.001-0.25% by weight of the total composition). Known antioxidants can be included. These antioxidants are often mixed with fatty acids.

The composition of the present invention also comprises USP 50715.
86 (Lever brothers Company), incorporated herein by reference, may also include a peptizer polymer.

When the liquid composition is an aqueous composition, the balance of the composition is in an aqueous medium. If non-aqueous, the above ingredients make up the total composition (the non-aqueous composition may contain up to 5% by weight of water).

An ideal liquid detergent composition has the following (1)-
(7) (wt%): (1) 5 to 70% cleaning active system; (2) 0 to 50% builder; (3) 0 to 40% electrolyte; (4) 0.01 to 5% Enzyme; (5) 0.1 to 15% enzyme stabilizer; (6) 0 to 20% phase modifier; and (7) balance water and minor substances.

The detergent composition of the present invention may also be a powder detergent composition.

Such powder compositions generally comprise from 5 to 40% by weight of a detergent active system consisting of anionic active agents, nonionic active agents, fatty acid soaps or mixtures thereof; 20
~ 70 wt% alkaline buffer; up to 60 wt%, preferably 10-60 wt%, more preferably 40 wt%
Builder up to; including balance minor substance and water.

The alkaline buffer may be any buffer capable of providing a 1% solution of substance having a pH above 11.5 or exactly 12. The preferred alkaline buffers are alkali metal silicates, in particular sodium orthometasilicate or sodium disilicate, of which sodium metasilicate is preferred, since it reduces corrosion of the metal parts of the washing machine. Alkaline buffer is 0
Suitable is ˜70 wt%, preferably 0-30 wt%.

The composition of the present invention also comprises 60% of the total composition.
Up to and preferably 10 to 60% by weight and more preferably up to 40% by weight detergent builder may and usually are included.

Suitable builders include pyropolyphosphoric acid, tripolyphosphoric acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, ether polycarboxylic acids, citric acid,
Mention may be made of sodium, potassium and ammonium or substituted ammonium salts such as carbonic acid, orthophosphoric acid, carboxymethyloxysuccinic acid. Other builders include DPA and ODS. Further, a builder having a small solubility is also included, and for example, there is zeolite that can be easily dispersed. Especially preferred are builders of polyphosphates, nitrilotriacetates, citrates, carboxymethyloxysuccinates and mixtures thereof.

Other conventional materials can also be present in small amounts. However, it exhibits a good dissolution and dispersion behavior, and includes, for example, sequestering agents such as ethylenediaminetetraphosphonic acid; sodium salts of carboxymethyl cellulose, polyvinylpyrrolidone or maleic anhydride / vinyl methyl ether copolymers, and hydrotropes. Soil dispersants; Dyes; Fragrances; Brighteners; Alkali-stable enzymes; Bactericides; Anti-tarnish agents; Foam inhibitors; Textile softeners; Oxygen or dichlorocyanurate or alkali metal hypochlorite Examples include chlorine bleach.

The balance of the composition is generally water, and at least a portion can be present as bound water of hydration.

An ideal powder detergent composition has the following (1) to
(7) (wt%): (1) 5-40% detergent activator; (2) 0-60% builder; (3) 0-30% buffer salt; (4) 0-30% sulfuric acid. (5) 0 to 20% bleaching system; (6) 0 to 4% enzyme; and (7) 100% small amount of substance and water.

In another aspect of the invention, glycolipid surfactants may be used in the light duty liquid detergent composition, eg USP4671894 (Lamb et al.), USP.
4368146 (Aronson et al.) And USP45553.
66 (Bissett et al.). All of these documents are incorporated herein by reference.

In general, such compositions comprise an anionic surfactant mixture of sulphate and sulphonate with a foam stabilizer. These compositions also include nonionic surfactants to reduce the amount of non-working components such as solvents and hydrotropes, and zwitterionic surfactants to enhance their ability to remove greasy and particulate soils. An agent may be included.

Other components that can be used in such a composition include emulsifiers (eg ethylene glycol distearate), thickeners (eg guar gum), antibacterial agents, discoloration inhibitors, heavy metal chelating agents (eg , EDT
A), perfumes and dyes.

The present invention will be described in more detail by the following examples, but the following examples are merely for illustrating the present invention, and the present invention is not limited by the following examples. .

[0076]

EXAMPLES Method for producing N-alkyl lactobionamides Synthesis of N-alkyl lactobionamides N-alkyl lactobionamides were prepared in anhydrous DMF or methanol, or without solvent, as shown below.
It was synthesized by reacting commercially available lactobiono-1,5-lactone with various chain alkylamines.

[0077]

[Chemical 6]

[In the formula, n is 2 to 17. ] Dimethylformamide solvent In this method, 80% lactobiono-1,5-lactone was added.
Dissolved in a small amount of anhydrous DMF at ° C, then added 1 equivalent of alkylamine. This method yielded high yields, but the product was colored and required repeated washings with solvent.

Methanol Solvent This method was carried out as described in USP2752334 (Walton). Lactobiono-1,5-lactone and alkylamines were refluxed in methanol to give the corresponding colored substances in moderate yields. Sequential washing with solvent was required to decolorize the product.

Solventless Method Excess alkylamine and lactobiono-1,5-lactone were heated at 90-100 ° C with vigorous stirring. A colored substance was obtained in moderate yield.

An example of each of these methods is given in more detail below.

Another of N-tetradecyl lactobionamide
In a 5 liter 3-neck round bottom flask equipped with a condenser and a bi-mechanical stirrer, lactobiono-1,5-lactone (400 g) was warmed with methanol (3.5 l, 5 l).
0-55 ° C). Molten tetradecylamine (1.0 eq, 272g) was then added. The reaction was cooled to room temperature and then stirred overnight for complete crystallization. The desired white material was filtered and isolated by recrystallisation from methanol (91% yield, 550 g). The methanol filtrate contained a mixture of N-tetradecyl lactobionamide and tetradecylammonium lactobionate.

The above method can also be used to isolate other N-alkyl aldbionamides.

Example 1: Preparation of N-decyl lactobionamide 20 g of lactobiono-1,5-lactone (1 equivalent) was dissolved in 40 ml of anhydrous DMF at 75-80 ° C and 8.8.
g (1 equivalent) of decylamine was added. The reaction product is 7
Stir at 5-80 ° C. for 30 minutes, cool and add ethyl ether (150 ml). The product was filtered and washed with ethyl ether (2 x 100 ml). Recrystallisation from methanol / ethyl ether gave the desired material in 80% yield.

Example 2: Preparation of N-dodecyl lactobionamide 30 g of lactobiono-1,5-lactone (1 eq.) Was dissolved in 70 ml of anhydrous DMF at 75-80 ° C, 15.
85 g (1 eq) dodecylamine was added. The reaction mixture was stirred at 70-80 ° C. for 30 minutes, cooled and ethyl ether (200 ml) was added. The product was filtered and washed with ethyl ether (2 x 150 ml). Recrystallization from methanol gave the desired material in 90% yield.

Example 3: Preparation of N-tetradecyl lactobionamide Lactobiono-1,5-lactone (20 g, 1 eq) was dissolved at 65 ° C in 60 ml of anhydrous DMF. 12.5g
Add (1 equivalent) tetradecylamine and add 3 at 65 ° C.
Stir for 0 minutes. The reaction mixture was cooled and ethyl ether (2 x 150 ml) was added. The product was filtered and washed with ethyl ether. Recrystallization from methanol gave the desired material in 92% yield.

Example 4: Preparation of N-hexadecyl lactobionamide A procedure similar to that of Example 3 was carried out using 10 g of lactobiono-1,
Performed using 5-lactone (1 eq) and 7.1 g hexadecylamine (1 eq). Recrystallization from methanol gave the desired material in 90% yield.

Example 5: Preparation of N-propyl lactobionamide 5 g of lactobiono-1,5-lactone (1 equivalent) was added to 8
It was dissolved in 20 ml of anhydrous DMF at 0 ° C and 0.86 g (1
Eq) propylamine was added. The reaction was stirred at 80 ° C. for 30 minutes and the solvent was removed. The residue was washed with ethyl ether (2 x 50 ml) and recrystallized with methanol / ethyl ether to give the desired material in 80% yield.

Example 6: Preparation of N-pentyl lactobionamide Lactobiono-1,5-lactone (5 g, 1 eq) and amylamine (1.41 g, 1 eq) are heated in 30 ml of anhydrous methanol and refluxed for 1 hour. did. A small amount of activated carbon was added and hot filtration was performed. The solvent was removed and the residue was washed with ethyl ether then acetone and dried. The yield was 50%.

Example 7: Preparation of N-octyl lactobionamide Lactobiono-1,5-lactone (10 g, 1 eq) and octylamine (7.6 g, 2 eq) are heated to 90 ° C. for 30 minutes with vigorous stirring. did. The reaction was cooled and washed with ethyl ether (2 x 150 ml). Recrystallisation twice with methanol / ethyl ether gave the desired material in 80% yield.

Example 8: Preparation of N-dodecyl lactobionamide 20 g lactobiono-1,5-lactone and 11 g.
Of dodecylamine (1 eq) was dissolved in 200 ml of methanol by heating to reflux temperature. The reaction mixture was stirred overnight at room temperature. The product was filtered, methanol (100 ml) then ethyl ether (2 x 75
ml). Recrystallization from methanol gave the desired material in 57% yield.

Example 9: N-Lactobionyl dodecyl glycinate 9.0 g of dodecyl glycinate hydrochloride are dissolved in 50 ml of anhydrous methanol with gentle heating to 2.0 M
After adding 16 ml of methanolic ammonia in
0.9 g (1 equivalent) of Lactobiono-1,5-lactone was added. The reaction mixture was heated to reflux for 2.0 hours, activated carbon was added and the mixture was hot filtered. The solvent was removed, the product was washed with ethyl ether and dried in a vacuum oven at 40 ° C. with P ₂ O ₅ to give a yield of about 75%.

Example 10: N-Lactobionyl dodecyl β-alanate Using a method similar to that described above for dodecyl glycinate, 3.0 g of dodecyl β-alanate hydrochloride in anhydrous methanol 3.45 g of lactobiono-. Reacted with 1,5-lactone. The yield was about 70%.

Example 11: N-dodecyloxypropyl lactobionamide 400 g of 50 g of lactobiono-1,5-lactone
Dissolved in methanol (50-55 ° C) and oxypropyldecylamine (Adogen (R) 180, 31.6 g, 1 equivalent)
Is added. The reaction is cooled to room temperature and then stirred overnight. Reduce the solvent to 150 ml and add acetone (40
0 ml) is added. The product was filtered, washed with acetone and dried in a vacuum oven at 40 ° C.

Example 12: Preparation of cocolactobionamide Lactobiono-1,5-lactone (400 g, 1 eq)
Was dissolved in methanol (2.3 l, 50 ° C.) with stirring and cocoamine (Adogen ™ 160-D (R) 21
(1, 8 g, 1 eq) was added slowly over 10 minutes.
After the addition was complete, the reaction mixture was stirred for an additional 10 minutes and the solution was seeded with a small amount of cocolactobionamide.
It was left overnight with stirring at room temperature. The product was filtered, washed twice with warm acetone and dried in a vacuum oven at 40 ° C. The yield was 394 g.

Example 13: Preparation of talloractobionamide Lactobiono-1,5-lactone (200 g, 1 eq)
Was dissolved in methanol (1.3 L, 45 ° C.) with stirring and tallow amine (Adogen ™ 170-D (R) 1
44, 7 g, 1 eq) was added slowly in several portions. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The product was filtered, washed with isopropanol, then acetone and dried in a vacuum oven at 40 ° C. Yield 270
It was g.

Example 14: Preparation of oleyl lactobionamide Lactobiono-1,5-lactone (100 g, 1 eq)
Was dissolved in methanol (400 ml, 50 ° C.) and oleylamine (Adogen ™ 127-D, 76.1 g, 1
Equivalent) was added slowly. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The product was filtered, washed twice with acetone and dried in a vacuum oven at 40 ° C. Yield 13
It was 0 g.

Example 15: Preparation of N-dodecyl-N-methyl lactobionamide Lactobiono-1,5-lactone (8.7 g, 1 eq)
Was dissolved in methanol (30 ml, 50 ° C.) and N-dodecylmethylamine (5 g, 1 eq) was added. The reaction mixture was stirred at room temperature overnight. The solvent was removed, the product was washed with acetone and dried in a vacuum oven at 40 ° C. The yield was 12 g.

Surfactant To investigate the effectiveness of these compounds as surfactants, various physical properties of the surfactant (ie, CM
C, Kraft point, foam height, zein dissolution, detergency) were measured. In particular, these properties were compared to the well-known and commonly used ethoxylated nonionic surfactants. The results of these various measurements are shown in Examples 16-18 below.

Example 16: Critical Micelle Concentration (CMC) CMC is defined as the concentration at which the surfactant begins to form micelles in solution. In particular, substances that contain both hydrophobic and hydrophilic groups (such as surfactants) disturb the structure of the solvent (ie, water) in which they are present, thus increasing the free energy of the system. Tend. Therefore,
Such materials collect at the surface, where their hydrophobic groups are oriented towards the outside of the solvent, minimizing the free energy of the solution. Another way to minimize the free energy is achieved by aggregating these surface-active molecules into clusters or micelles. In the cluster or micelle, the hydrophobic group faces the inside of the cluster and the hydrophilic group faces the solvent.

The CMC value is determined by measuring the surface tension using the Wilhemy plate method. Although not wanting to be bound by theory, a low CMC is a measure of surfactant (ie, one surfactant with a lower CMC has greater surfactant activity than another). . In this regard, the smaller CMC means
It is believed to mean that a smaller amount of surfactant is needed to obtain a similar surfactant effect to a surfactant with a higher CMC. CMC of various surfactants
Was measured and the results are shown below.

Surfactant CMC n-dodecyl-β-D-glucoside 1.9 × 10 ^-4 M (25 ° C.) n-C ₁₂ alcohol (with 7 EOs) 7.3 × 10 ^-5 M ( 40 ° C.) C ₁₀ -lactobionamide ----- C ₁₂ -lactobionamide 4.2 × 10 ⁻⁴ M (45 ° C.) C ₁₄ -lactobionamide 4.5 × 10 ⁻⁵ M (45 ° C.) From the above table As can be seen, the CMC values for N-decyl and tetradecyl lactobionamide are N-dodecyl-β.
It was found to be comparable to -D-glucoside and heptaethoxylated dodecyl alcohol. These values indicate that the lactobionamide surfactant is comparable to other widely used nonionic surfactants.

Example 17: Kraft Point The temperature at which the surfactant starts forming micelles instead of precipitation is called Kraft point (T _k ), and the solubility of the surfactant is
At this temperature it equals CMC.

Kraft point measurements were made by making a 1% aqueous dispersion of surfactant. If the surfactant was soluble at room temperature, the solution was cooled to 0 ° C. If no surfactant was precipitated, the Kraft point was considered to be <0 ° C. In case of precipitation, the solution was warmed slowly with stirring in a water bath. The temperature at which the precipitate dissolved was measured and used as the Kraft point.

When the Kraft point was above room temperature, the solution was first rapidly heated to dissolve all surfactants. Then, after cooling until a precipitate was formed, it was slowly warmed and the Kraft point described above was measured.

Without wishing to be bound by theory, it is believed that lower Kraft points indicate greater solubility of the surfactant in aqueous systems.

The Kraft points for various lactobionamides are shown below.

[0108] From this table it can be seen that surfactants with a chain length of C ₁₀ tend to have better surface activity at lower temperatures than those with C ₁₂ and C ₁₄ .

Example 18: Foam Height Foam is an important property in many consumer products. Foam is one of the main factors that determines the commercial value of products such as shampoo and soap. Also, the acceptability of many consumer products is closely related to the quality (physiological aspect) of the foams produced thereby.

Most of the foam data for surfactants is typically obtained by the Ross-Miles method (Ross, J. and Miles,
GD, Am. Soc. For Testing Material Method D1173-5
3 Philadelphia, PA. (1953); Oil & Soap (1958) 62: 1
260), and the foam-forming ability of these surfactants was also investigated using this method.

According to the Ross-Miles method, 2.9 mm-i.
d. 200 ml of the surfactant solution in a pipette of a certain size with the orifice of the above is placed on the same solution of 50 ml in a cylindrical container maintained at a constant temperature (often 60 ° C.) by a water jacket from 90 cm above. I dropped it. The bubble height generated in the cylinder was read immediately after the entire solution had flowed out of the pipette (first bubble height) and then again after a period of time (generally 5 minutes).

Using this method, foam formation (measured first) and foam stability (foam height after 10 minutes) are reported. All foaming was done at 45 ° C. in water with a hardness of 120 ppm. The height of bubbles is expressed in mm.

The initial foam height and foam height after 10 minutes (ie foam stability) for various surfactants and surfactant mixtures are given below.

[0114] As can be seen from the above, the foam stability of the C ₁₄ -lactobionamide and the C ₁₂ and C ₁₄ lactobionamide mixture is the best.

The stability of this type of foam is not so common in other nonionic substances.

N-dodecyl and N-tetradecyl lac
Evaluation of Detergency of Tobionamide General Experiments Detergency of three types of lactobionamide samples (C ₁₂ -lactobionamide , C ₁₄ -lactobionamide and lactobionamide having a C ₁₂ to C ₁₄ ratio of 1: 1) was measured by Tergo.
It was evaluated by a tometer test. The performance of lactobionamide is demonstrated by Neodo, a commercially available ethoxylated nonionic substance.
l (trademark) 25-7 (alkyl chain length is 12 to 15 carbon atoms)
And has 7 ethoxy groups). N-
Since the alkyl lactobionamides are expected to be in a mixed active system, the Tergotometer test showed linear alkylbenzene sulfonate (LAS) / lactobionamide ratios of 25/75, 50/50, 75/25 and 90.
It went to / 10.

The test cloth used in most of the tests was Lev.
er clay cloth (very hydrophobic ditallow, 65/35 polyester / cotton cloth coated with kaolinite clay / quartz mixture coated with dimethylamine cation), VDC cloth (treated with greasy soil collected from a vacuum cleaner bag) 65/35 polyester / cotton blend), W
KF30C cloth (polyester with standard WFK stains)
And WFK30D cloth (pigment / sebum-stained polyester). To test the ability of C ₁₂ -lactobionamide to remove blood stains, EMPa-116
A cloth (cotton cloth stained with milk and ink in addition to blood) was used.

Phosphorus-free, using zeolite as a builder b
The urkeite base powder was added to the sides at approximately 1.85 g / l. Hardness was added with a Ca: Mg ratio of 2: 1. The system was maintained at pH = 10 and the Tergotometer test was run for 10 minutes.

Improving detergency is achieved with a dirty cloth and tergotomete
It is measured by the change in reflectance (ΔR) with respect to the cloth treated with r. The reflectance was measured using a reflectometer, and the amount of change was obtained by the difference in reflectance before and after each washing.

Example 19 As described above, a sample of C ₁₂ -lactobionamide, C ₁₄ -lactobionamide and lactobionamide having a C ₁₂ to C ₁₄ ratio of 1: 1 was prepared at 15 ° C. and 180 pp.
Evaluations were performed on Lever clay fabrics under various tergotometer conditions (harsh conditions) of m-salt at various anionic (LAS) to lactobionamide (or commercial Neodol) ratios. The results are shown below.

ΔR 0/100 25/75 50/50 75/25 100/0 C ₁₂ 11.2 10 9.2 10.3 12.2 C ₁₄ 10.1 9.5 9.6 11.2 15 1: 1 C at various anionic to nonionic ratios ₁₂ / C ₁₄ 11.9 10.7 10.0 12 14 Neodol 25-7 16.8 15.0 12.8 11.8 12.0 The above results show that pure LAS (ie,
The detergency of the 100/0 ratio) was better than both the three lactobionamide samples (ie, 0/100 ratio) and the samples consisting of various anionic to nonionic ratios. Also, using the above conditions, LAS /
We also tested on the Neodol 25-7 series. Comparing the Neodol results with the lactobionamide results shows that for the Lever clay cloth, Neodol 25-7 is superior to both the pure and mixed active systems of lactobionamide. It is speculated that the low temperature and high hardness conditions used in these tests affected the results.

Example 20 For samples of C ₁₂ -lactobionamide, C ₁₄ -lactobionamide and lactobionamide with a C ₁₂ to C ₁₄ ratio of 1: 1 15 ° C., 180 ppm salt tergotome.
Under ter conditions (harsh conditions), various anionic substances (L
The AS) to lactobionamide or Neodol (nonionic) ratio was evaluated for VCD fabrics. The results are shown below.

ΔR 0/100 25/75 50/50 75/25 100/0 C ₁₂ 28.2 27.5 30 31 32 C ₁₄ 29.8 29.5 31.5 33.5 33.8 1: 1 C at various anionic to nonionic ratios ₁₂ / C ₁₄ 29.8 29.5 29.5 32.5 32.5 Neodol 25-7 25 25.5 31.0 31.5 32 Test results (15 ° C. and 180 ppm hardness) obtained using VCD cloth are the lactobionamide sample and LA.
Anionic surfactants showed better results as well, although there was no significant difference between detergency with S. However, unlike the results obtained using the Lever clay cloth (Example 19 above), the results for the LAS / lactobionamide mixed system are similar to those for the LAS / Neodol system even at the harsh conditions of 15 ° C. and 180 ppm. Results were equal or better.

Example 21 C ₁₂ -lactobionamide and Neodol 25-7 (nonionic) samples were tested under tergotometer conditions (mild conditions) at 40 ° C., 120 ppm hardness and pH 9.7.
VCD fabrics were evaluated at various anionic (LAS) to nonionic ratios. The results are shown below.

ΔR 0/100 25/75 50/50 75/25 100/0 C ₁₂ 33 34 34.9 36 35 Neodol 25-7 32.8 32 33.0 34 34.5 at various anionic to nonionic ratios The results show that various LASs using VCD cloth:
C ₁₂ - lactobionamide ratio and LAS: Neodol 25-
7 shows the ΔR value obtained for the ratio. The results for these mild conditions (40 ° C., 120 ppm) are the results of the same test performed at 15 ° C. and 180 ppm, ie C ₁₂ -lactobion when tested in a mixed nonionic / anionic system. Amido Neodol 25-7
It is comparable to the result of showing the result equal to or better than.

Example 22 C ₁₂ -lactobionamide and Neodol 25-7 (non-ionic) samples were tested under tergotometer conditions (mild conditions) at 40 ° C., 120 ppm hardness and pH 9.7.
The EMPA-116 fabric was evaluated at various anionic (LAS) to nonionic ratios. The results are shown below.

ΔR 0/100 25/75 50/50 75/25 100/0 C ₁₂ 35 38 40 42 45 Neodol 25-7 32.5 34 37.0 40 41 at various anionic to nonionic ratios. Results were obtained using EMPA-116 test cloth,
Various LAS: C ₁₂ -lactobionamide ratios and LA
The ΔR value obtained for the S: Neodol 25-7 ratio is shown (40
C, 120 ppm 2: 1 Ca: Mg hardness). The results show that the removal of blood by C ₁₂ -lactobionamide is not as great as LAS, but compared with Neodol 25-7, 3Δ
It can be seen that only R units are good.

Example 23 For samples of C ₁₂ -lactobionamide and Neodol 25-7 (nonionic), various anionic substances (LAS) versus non-ionic substances under tergotometer conditions of 40 ° C., 120 ppm hardness and pH ˜10. WKF30C in ionic substance ratio
And the WFK30D cloth was evaluated. The results are shown below.

ΔR 0/100 25/75 50/50 75/25 100/0 WFK30D C ₁₂ 15.0 18.0 21.8 25 26 Neodol 25-7 12.0 16.0 19.5 22.8 26 WFK30C at various anionic to nonionic ratios. C ₁₂ 4.0 6.2 9.0 10.9 11.0 Neodol 25-7 2.0 4.8 7.0 9.5 11.0 As can be seen from the results, the anionic surfactant was again used in all anionic / nonionic pure systems and mixed systems. Are better. In addition, lactobionamide is
Neodol 25-7 in mixed active and all non-ionic systems
Equal to or slightly better than.

Generally, in detergency evaluations, the surfactants of the present invention were tested for all substances tested (Lever Clay).
However, it is better than the commercially available Neodol 25-7. Further, in the examples in which the same result was not obtained, the washing was performed under severe conditions.

Example 24 Furthermore, the evaluation of detergency of greasy soil was carried out by examining the removal of radioisotope-labeled triolein in a tergotometer experiment. In this example, reference is made to the drawings.

Stain removal was evaluated using ³ H triolein, and after washing, 4 × 1 ml samples of the wash liquor were removed from each pot and assayed for activity with a scintillation counter. Detergency (%) was calculated from the following relational expression.

[0133] During the cleaning property _{(%) = A w / A} s × 100 [ wherein, A _w is the total activity of the washing liquid, A _s is the amount of activity that is first applied to the fabric. ] The washing conditions were as follows: washing time: 20 minutes; washing temperature: 40 ° C; stirring: 7
0 rpm; washing liquid volume: 500 ml; substance usage:
1 g / l; salt concentration (sodium carbonate): 0.05 M; amount of stains attached to the knit polyester test cloth: about 1.9% by weight.

[0134] C ₁₄ -, C ₁₂ - and coconut - shown in the accompanying FIG washing of measurement results in a mixture with lactobionamides alone and C ₁₂ EO ₃ nonionic surfactant.

When these lactobionamides were mixed with 3EO nonionics, synergistic detergency was observed.
For example, in the case of C ₁₄ substance, the surfactant composition is 80%.
A synergistic sharp maximum (about 65% detergency) was observed with lactobionamide / 20% nonionic.

These detergency results indicate that lactobionamide is a substance that can replace high HLB ethoxylated nonionic surfactants, especially in detergent compositions for textiles.

Example 25: Cyclic Aldionamide vs. Chained Aldonamide The aldobionamide of the present invention (ie, at least 2).
1 wt% solution of C ₁₀ , C ₁₂ and C ₁₄ gluconamide and lactobionamide (water) to show that saccharide units having 4 saccharide units are advantageous over chain saccharides (eg gluconamide). The Kraft point of 1 g of surfactant in 99 g) was measured.

Gluconamides have the general formula:

[0139]

[Chemical 7]

[Wherein R ₁ and R ₂ are as defined above for the aldobionamide of the present invention. ]
The results are shown below.

[0141] As is evident from these results, the Kraft point of lactobionamide is always much lower than that of gluconamide.
That is, the solubility of lactobionamide is considerably high.

A low craft point is also associated with high foaming.

[Brief description of drawings]

FIG. 1 is a graph showing the detergency of various surfactants.

─────────────────────────────────────────────────── ───

[Procedure amendment]

[Submission date] March 1, 1993

[Procedure Amendment 1]

[Document name to be amended] Statement

[Name of item to be corrected] 0133

[Correction method] Change

[Correction content]

Detergency (%) = (A _W / A _S ) × 100 where A _W is the total activity of the wash liquor and A _S is the amount of activity initially applied to the fabric. ] The washing conditions were as follows: washing time: 20 minutes; washing temperature: 40 ° C; stirring: 7
0 rpm; washing liquid volume: 500 ml; substance usage:
1 g / l; salt concentration (sodium carbonate): 0.05 M; amount of stains attached to the knit polyester test cloth: about 1.9% by weight.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Vijayan Harriachian, United States, New Jersey, County of Essexs, West South Orange Avenue 420 (72) Inventor Michael Matsusaro United States, New York -10920, Congers, Dover Road-39 (72) Inventor Abid Naiden Khan-Rhoday, Chester Sea H. 2.2, J.A. Day, Hiewuit Hall 29, England

Claims (11)

[Claims] 1. A detergent composition suitable for cleaning fibers or hard surfaces, comprising a nonionic glycolipid surfactant which is an aldobionamide. 2. Aldionamide has the structural formula: ANR ₁
R ₂ [wherein A is a sugar moiety which is an aldobionic acid except that it does not contain an OH group extending from the carbonyl group of a normal aldobionic acid; NR ₁ R ₂ is a hydroxyl group if it is a normal aldobionic acid Bound to a certain position; R ₁
And R ₂ may be the same or different and are selected from the group consisting of hydrogen, aliphatic hydrocarbons, aromatic residues, cycloaliphatic residues, amino acid esters, ether amines and mixtures thereof. However, R ₁ and R ₂ do not become hydrogen at the same time. ] The composition of Claim 1 characterized by having. 3. R of the aldobionamide is hydrogen,
The composition according to claim 2, wherein R ₁ is an alkyl group having 8 to 24 carbon atoms. 4. The composition according to claim 2, wherein A of the aldobionamide is a disaccharide residue forming a compound that is aldobionic acid except OH. 5. The aldobionamide has the following structural formula: [In the formula, R ₁ and R ₂ may be the same or different, and each of hydrogen, aliphatic hydrocarbon, aromatic residue, alicyclic residue,
It is selected from the group consisting of amino acid esters, ether amines and mixtures thereof. However, R ₁ and R ₂
Do not become hydrogen at the same time. ] The composition according to claim 2, which is lactobionamide. 6. The aldobionamide has the following structural formula: [In the formula, R ₁ and R ₂ may be the same or different, and each of hydrogen, aliphatic hydrocarbon, aromatic residue, alicyclic residue,
It is selected from the group consisting of amino acid esters, ether amines and mixtures thereof. However, R ₁ and R ₂
Do not become hydrogen at the same time. ] The composition according to claim 2, which is a maltobionamide. 7. A co-selection selected from fatty acid soaps, anionic non-soap surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants and zwitterionic surfactants. The composition according to claim 1, which comprises a surfactant. 8. Composition according to claim 7, characterized in that the synergistic surfactant is an ethoxylated alcohol nonionic surfactant. 9. The following (1) to (7) (wt%): (1) 5 to 70% containing an aldobionamide surfactant
(2) 0 to 50% builder; (3) 0 to 40% electrolyte; (4) 0.01 to 5% enzyme; (5) 0.1 to 15% enzyme stabilizer. (6) 0 to 20% of a phase control agent; (7) A liquid detergent composition containing the remaining water and a small amount of a substance.
The composition according to. 10. The following (1) to (7) (% by weight): (1) 5 to 40% containing an aldobionamide surfactant
(2) 0-60% builder; (3) 0-30% electrolyte; (4) 0-30% sulfate; (5) 0-20% bleaching system; (6) 0 ~ 4% enzyme; (7) a powder detergent composition comprising a small amount of 100% and water.
The composition according to. 11. The following (a) to (e) (% by weight): (a) 0.01 to 65% anionic surfactant; (b) 0.1 to 50% aldobionamide surfactant. Agent; (c) 0-8% foaming promoter; (d) 0-10% hydrotrope; (e) Light duty liquid detergent composition containing 100% small amount of substance and water. The composition according to claim 1, characterized in that