JPH07508546A - Surfactants derived from polyoxyalkylenes and substituted succinic anhydrides - 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] Surfactants derived from polyoxyalkylenes and substituted succinic anhydrides The present invention relates to surfactants, and in particular to novel surfactants based on substituted succinic acid derivatives. Concerning active agents and specific end uses of these surfactants.

In recent years, there has been a demand for highly biodegradable materials to replace well-established surfactants. It was growing. However, it has occupied an important position in the market for several decades. In fact, it is very difficult to devise another material to replace one material with superior performance.

European Patent No. 0107199 discloses C8-C1a alkyl(kenyl) substituted succinic acid and Concerning polyoxyalkylene glycol hemiesters of their salts. these The material is an anionic surfactant that develops specific utility at acidic pH and has hard water resistance. recorded as a drug.

The present invention particularly relates to C14-C22 alkyl (kenyl) groups and/or any Compounds derivable from alkenyl succinic anhydride having substituents of or other functional groups are Based on the discovery that it provides materials with significantly and surprisingly different properties, In particular, the said compound is an unexpected compound that has shown good performance at elevated temperatures, especially in aqueous systems. It functions well as a non-ionic surfactant with clear cloud point characteristics and is resistant to alkaline conditions. The surfactants of the present invention also exhibit good biodegradation properties under these conditions. .

Therefore, the present invention provides the following formula (I) or (II); Y, A1. OC, (HR)C,C( )IRl), CO, A, (C, H,,,0),, R'' (I) [in the formula R and R1 one is a C6-CZZ alkenyl or alkyl group, and the other is hydrogen; A is 10- or -NR4- (where R4 is hydrogen or C2-C6 alkyl, especially methyl or ethyl group); n is 2 to 100 (L, or when n is an average value may be a non-integer); m is 2 or 3 (and can vary with the polyoxyalkylene chain); R2 is hydrogen or a C1-C6 alkyl group; A1 is 10-, -0- or -NR 4- (However, R4 is hydrogen or 61-C are also alkyl groups, especially methyl or ethyl groups) and thus when A1 is 10- Y is a cation, especially Hl and an alkyl metal cation, especially sodium or potassium Cations or ammonium ions (particularly NH, amine ammonium or alkanolamine (ammonium ion); When Al is 10- or -NR4-, Y is a C1-C6 alkyl group (R3) or is the following formula (C+sH2+-0), , R2 (where m, n and R2 are individually as described above) is the basis of However, when A is 10- or At is 10-, the groups R, R' and any group R2 and The total number of carbon atoms in R3 is at least 13, preferably from 13 to 50.] Or Y, A1. OC, ()IR)C1C(HRI),■,A,(-shiO)I , C, H2, five ω, (dish C, C (dish) ω, A’Y (II) (In the formula, n, m and each R, R1, A, A' and Y are individually as described above (and ; p is 2 or 3).

For convenience of definition, the free acid form of the compounds of formulas (I) and (II) is defined as Y as the H+ cation. Defined by Of course this definition.

relative to the ionized form of the free acid that typically exists at relatively alkaline pH. It includes both the non-ionized form that typically exists at acidic pH.

In general formula (I), A and A1 are both -0-1 both -NR4- especially -NH - or A is -NR4- especially -NH- and Al is preferably 10- and therefore the following particular subgroups of compounds of formula (I) form a particular embodiment of the invention: (See below for R and R1).

(Ia) Y,”’OOC, (I(R)C,C(HR’),COO,(C-Hz -0), , R2 [where m, n and R2 are as described above for formula (I)] ; Y is a cation as described above for formula (I); one of R and R1 is C1 4-C22 especially C14-C20 alkenyl or alkyl group, the other being hydrogen ] (Ib) Y, 0.0C, (HR) C, C (HR'), C0,0, (Cm R2,0), , R2 [wherein m, n and R2 are as described above for formula (I) Yes; Y is a C1-C6 alkyl group as described above for formula (I) or a group of the following formula (C, , R2,, O), , R''; R and R1 are as described above for formula (I). However, in particular, one of R and R1 is C14 to C22, especially C14 to C2o. , alkenyl or alkyl group, and the other is hydrogen] (Ic) Y, 0. OC, (HR)C,C(HRS,CO,NH,(C,R2, 0),,R2 [wherein Y, m, n and R2 are as described above for formula (I) ; R and R1 are as described above for formula (I), but in particular one of R and R1 is C14 to C22, especially C14 to C2°.

is an alkenyl or alkyl group, and the other is hydrogen] (Id) R'', (C- H,,0),,Suba)C(HR)C,C(HR'),CO,NH,(C,82, 0), ,R” [wherein each m, n and R2 are individually as described above for formula (I)] R and R1 are as described above for formula (I), but in particular R and R One of 1 is a C14-C22, especially C14-C2゜, alkenyl or alkyl group and the other is hydrogen].

The compound of general formula (II) has a di(substituted succinyl) group in the polyoxyalkylene moiety. 0 Usually, each group A and AI and Y are the same group. 0 both groups A are 10- or -NR4- especially -NH-, and both groups A1 are 10 - and Y is preferably a cation.

Similarly, the alkyl(kenyl) groups in the groups R and R1 are usually the same group.

When Y is a cation in formulas (I) and (II), H+, alkali metal cations or ammonium cations, especially NH4”, amine ammonium cations For example, tetramethylammonium or alkanolamine ammonium ions. For example, HO, CH2C) (2, NH, + is preferable; Y is C1 to C6 a in particular methyl, ethyl or (straight-chain or branched) butyl groups. be.

In formulas (1) and (II), the group R2 is H or methyl, ethyl, Preferably a propyl or butyl (including branched propyl and butyl) group When R2 is H, the product tends to be relatively more hydrophilic; When 2 is an alkyl group, it tends to be relatively less hydrophilic. group R2 The choice of is determined by the overall desired properties of the compound.

The compounds of the present invention are residues of ethylene glycol and/or propylene glycol. at least one polyoxyalkylene chain formed from Polioki A sialkylene chain is a monomer of ethylene glycol or propylene glycol residues. Polymer chain or ethylene glycol residue and propylene glycol residue It can be a block or random copolymer chain containing both. more than one In compounds containing polyoxyalkylene chains, the chains may be the same or different. It's okay to stay.

In formulas (I) (including Ia, Ib and Ic) and (II), groups (C, R With particular reference to polyoxyalkylene chains defined as 2,,0), The chain length of this group, or the value of the parameter n, is chosen to give the desired properties to the intended product. Sea urchins are commonly selected. Typically, polyoxyalkyi special table Sen7-50854G (4) When the ethylene chain is a polyethylene glycol chain, it is usually 3 to 50, especially 3 to 50. 35 For example, it has 10 to 35 ethylene glycol residues, and When it is a xypropylene chain, usually 10 to 50, more preferably 12 to 2 There are 0 propylene glycol residues. polyoxyalkylene series The chain is a block or run of ethylene glycol and propylene glycol residues. In the case of dumb copolymers, the selected chain length typically corresponds to the above range, but Mathematically, the distribution of ethylene glycol residues and propylene glycol residues in the chain is We will respond accordingly. Of course, the numerical value of the repeat length of polyoxyalkylene chain is an average value. It is. As is common with surfactants containing polyoxyalkylene chains, The longer the chain and the higher the proportion of ethylene glycol residues, the more the product In the compound of formula (II), which is more hydrophilic, the polyoxyalkylene chain If m is constant along , then p is usually the same as m.

Among the compounds of the invention, the groups R and R1 are C14-C2□, especially C14-C2□, Compounds which are very particularly C14-C2□, alkenyl or alkyl groups are particularly desired. Similarly, compounds in which the group R or R1 is an alkenyl group are those in which the group R or R1 is an alkenyl group. More preferred than compounds in which the group R or R1 is an alkenyl group, especially CI4 Compounds that are ˜C20 alkenyl groups form a particular embodiment of the invention.

Compounds of the invention, especially in which the groups R and R1 are CI4-C22 alkenyl or alkyl groups Compounds having the length of the chain R or R1, especially when this chain is an alkenyl chain, are has a completely unexpected property in that the cloud point tends to rise as the . Chain lengths longer than C14 often attract particular attention to the CI2-C14 linkage step For example, for compounds with a chain length of C1□, the cloud point tends to recede somewhat. This tendency for the cloud point to often remain significantly above the cloud point at The results show an increase in water solubility of the compound with increasing chain length, which is completely unexpected. Yes, contrary to conventional experience with surfactants.

However, at longer chain lengths the compounds are less effective wetting agents. This is consistent with an increase in the hydrophobicity of the group R/R1. formula;% formula% In a series of compounds (where n and R2 are as shown below); The cloud point ("C) for compounds in which R or R1 groups are in the range 10 to 18 is: It is like; C atoms in the group R/R' 8 12 14 16 18 R2=CH3, n near-3 770-8152-5351-52R2:H, r+-8<5 43 56.5 -　-[Compounds in this table (provided that R2=H and the chain length of R/R1 is 12 or less ) is not a compound of the invention.] The inventors are unable to explain this behavior. As far as the inventors know, this is unique among surfactants.

In aqueous systems, surfactants are usually most effective at or near their cloud point. In some respects it is actually quite important. A higher cloud point means a relatively higher temperature. Materials that are likely to remain active are shown, and surfactants are suitably maintained at super ambient temperatures. ambient) Often used at 1X degrees, longer chain lengths provide increased oil solubility and thus the cloud point behavior is better at higher working temperatures for better oil solubility. This indicates that they appear to be related. This is a very useful combination of be. This effect is more pronounced for compounds in which the groups R and R1 are alkenyl groups. In particular, compounds in which the group R or R1 is an alkyl group are more complex than the corresponding alkenyl compounds. This is because they generally have a lower cloud point.

The compound of formula (1) (where A1 is 10'' and Y is H+) is an alkenyl Or alkyl succinic anhydride according to the following formula; % formula % (wherein A, m, n and R2 are as described above) can be formed. The anhydride and polyalkylene glycol, polyalkylene gelico reaction between glycol monoalkyl ether or the corresponding amine derivative. by contacting the amine derivative with anikenyl or alkyl succinic anhydride. One reaction that can easily be carried out without or with a catalyst is typically below 200°C and Zero reactants that occur at temperatures even below 100°C are usually at least approximately stoichiometric. It is used in quantity. Further purification is usually necessary, especially when using stoichiometric amounts. It is not believed to be necessary, but can be done if desired.

The product is typically a mixture of isomers corresponding to the two anhydride ring opening reactions. a It is believed that the lekenyl or alkyl chain exerts a small steric effect on the isomer ratio. The inventors have discovered that the ratio of the isomers is typically about 60:40, with the predominant isomer Is the body a nucleophilic attack at an anhydride carbonyl group distant from an alkenyl group or an alkyl group? arises from

Compounds of the invention in which Y is another cation can be prepared by salt formation from the free acid (Y=H”). It can be formed by When Y is an alkali metal or ammonium cation, a salt The formation of the corresponding base e.g. an alkali metal e.g. sodium or potassium, hydroxide or alkanolamines such as carbonates, ammonia or ethanolamine. This method is simple due to the reaction with the first amine.

Compounds of the present invention in which A] is other than -〇-, that is, Y is other than a cation, are free acids or It can be formed by the following reaction.

Typically, further reactions are carried out by producing esters, especially 01-C6 or polyalkylene By producing esters with glycol alkyl ether alcohols. In general Long chain esters and corresponding amides can be combined with the corresponding alcohol (YOH’) or Amine (YNH2) (However, Y is Special Table Sen7-508546 (5) as mentioned above. esters with short-chain alcohols by transesterification or amidation In particular, it can be formed from methyl or ethyl esters. Esterification of free acids is a conventional The process is carried out using an acid catalyst which can be, for example, sulfuric acid, toluenesulfonic acid or phosphoric acid. be able to. Phosphoric acid is particularly useful. This is because after neutralization, phosphoric acid is This is because it can be a useful component of detergent compositions containing surfactants.

Compounds of formula Ia, Ib, Ic and Id can thus be formed as follows; Ia Polyoxyalkylene of the following formula i HO, (C, R2,,0), , R'' Reacting Recall or its derivatives with CI4~C22I4 succinic anhydride Let the following formula; %formula% and reacted with an alkaline material (if Y is other than H).

Ib In particular, the compound of formula (I) where Y is H is combined with a low molecular weight alcohol, especially methanol. , ethanol or butanol, followed by alcohol YO if necessary. Transesterification with H gives the required product.

Ic Aminopolyexy of the following formula i H2N, (C,,,R2,,0),,,R'' Reacting alkylene glycol or its derivatives with alkyl(kenyl)succinic anhydride Then the following formula; %formula%) and react it with an alkaline material (if Y is other than H) .

Id Following formula; 1(2N, (CiH2-0), , aminopolyoxyalkyl of R2 By reacting lene glycol or its derivatives with alk(enyl)succinic anhydride, formula; %formula% compound, followed by escaping with a low molecular weight alcohol, particularly methanol or ethanol. Tellification followed by amidation reaction with amine YN)+2 yields the desired product.

Compounds of formula (II) in which Y is H+ contain 2 moles of alk(enyl)succinic anhydride. 1 mole of the following formula; %formula% (wherein m, n, p and each A are as individually communicated) It can be formed by

Y is another cation or C1-C6 alkyl group (R3) or the following formula (CmH zmO), , R2 (wherein m, n and R2 are individually as described above) Compounds of formula (I) can be formed as described above for compounds of formula (I).

The compounds of the invention can be formed by other methods, such as from anhydrides to lower alcohols. can be reacted with polyalkylene glycol, and the resulting half ester can be reacted with polyalkylene glycol. or polyalkylene glycol alkyl ether; can be condensed with alkylene oxide and endcapped with another lower alcohol if desired. You can The chain length of polyalkylene glycol is polyalkylene with a narrow molecular weight range. By using glycol or polyalkylene glycol alkyl ether However, the latter method gives a wide chain length distribution.

Alkenyl succinic anhydride combines maleic anhydride with 6 to 22 carbon atoms, especially 14 to 22 carbon atoms. Excess amount of elementary olefin, for example, 50-200% excess amount and 150-400°C, The reaction is preferably carried out at a temperature preferably between 180 and 250°C, followed by e.g. It can be produced by removing excess olefin by distillation under vacuum.

Catalysts are not necessary but preferable to the presence of antioxidants, these anhydrides It is a knowledgeable industrial material. In the alkenyl succinic anhydride produced as described above, di The heavy bond is usually in the 2-position of the alkenyl substituent.

To form products in which the group R or R1 is an alkyl group, the unsaturated product is hydrogenated. or preferably by hydrogenating the intermediate alkenyl succinic anhydride. succinic anhydride can be obtained. Typically, hydrogenation is performed using Raney nickel or P over a hydrogenation catalyst such as a d/C catalyst, at a temperature of 15 to 100°C or from 0 to 200 bar. Absolute pressure can be used and a solvent may be present if desired, e.g. The hydrogenation reaction on kenyl succinic anhydride is carried out e.g. It can be carried out at 20°C using a wt% Pd/C catalyst.

Desirably, the R, R1 alkyl or alkenyl group of the compound of the present invention is a straight chain, If the chain is not linear, at most two in total and preferably only one The entire molecule, which should have an average of branched chains, should contain all the alkyls and It is preferred to contain a total of no more than 3 branches in the alkenyl and alkenyl groups.

The product is low odor, easy to form, and contains polyalkylene glycols and polyalkylene glycols. Kylene glycol alkyl ethers or their amine derivatives can be easily transported. Therefore, if these are used as reactants, it is necessary to use them from alkylene oxide manufacturing plants. Can be formed remotely.

The compounds of the invention develop emulsifying properties and wetting and dispersing abilities. These compounds include , oil-in-water emulsions and crude oils for metal working fluids based on semi-dissolved oils and synthetics Softeners for transportation and fuel systems, human (skin) care; household cleaning compositions e.g. Rinse: Dispersion in paints or organic and inorganic powders (e.g. fillers and pigments) and agricultural chemicals. Pharmaceutical preparations (e.g. pesticides); so-called industrial and public cleaning products (e.g. For example, it is used as a wetting agent in transportation film removal and bottle washing.

Specific end uses for the surfactants of this invention include wool scouring and acrylamide or the like. Inversion agents are used in the production of various products. These uses are detailed below. It is described in

When sheared from a sheep, the wool fleece contains a variety of substances in addition to wool fibers, including wool wax. Contains the following substances. Wool Poem Sen7-508546 (6) Wax is a complex mixture of fatty substances secreted by the sheep's skin onto the wool. sheep Waxing is typically carried out at moderately elevated temperatures such as 40-80°C, especially 50-70°C. The wool can be used as a textile by washing it with an aqueous mixture containing a surfactant. Removed from wool before use.

This method is called wool scouring.The tests of the inventor have shown that it is within the scope of the present invention. Surfactants are used to scouring very fine fiber wool, such as merino wool. even at times, especially when retaining their activity well even after numerous scouring cycles. It is a very effective surfactant for wool scouring, and the wool is difficult to scouring. Ru.

This is because the proportion of wool fat is relatively high and the fibers have a high surface area to process. It is from. The specific selection of compounds within the invention for this end use is Depending on the operating conditions, the compound of formula (Ia) above may be used, especially when m is 2 and n is 2. ~25, especially 3 to 10, and R2 is a C1-C6 alkyl group, especially a methyl group. The inventors have found that compounds that are particularly effective. Surfactants in this application is typically used at a concentration of 0.1 to 5, especially 0.2 to 1.5 g-R-'.

The present invention therefore relates to compounds of formula (I) or (1,I) as described above, particularly compounds of formula (Ia) as described above. In particular, m is 2, the number is 3 to 1O, and R2 is a C1 to C6 alkyl group, especially a methyl group. washing wax-containing wool with an aqueous mixture containing an amount of a compound that is Consisting of One aspect of the present invention includes a method of treating wool to remove wool wax. Also encompasses the use of such compounds of the invention as surfactants for wool scouring.

The production of polymers such as polyacrylamide requires the production of polymers in an aqueous phase, in which the polymer It is usually carried out by the emulsion polymerization method, in which the polymers are concentrated in soluble materials. polyacrylic It is well known that amides can give aqueous solutions with high viscosities even at low concentrations; are the basis for their use as thickeners and viscosity improvers in aqueous systems. If the liquid phase is a continuous phase, it quickly becomes very viscous, making it difficult to stir and recover the product. This will cause problems. To avoid this problem, stabilize water-in-oil emulsions. Including the emulsifier to make the water-in-oil emulsion, the aqueous phase is in the Tsutomuura continuous phase. It is a dispersed phase. The viscosity of the oil phase does not increase during polymerization like the aqueous phase, because This is because the body remains in the aqueous phase. However, polymers are typically At this point the emulsion must be inverted to provide an aqueous continuous phase. No. This is typically done by diluting a water-in-oil emulsion with water. Now. Typically, surfactants that promote such inversion are added to a water-in-oil emulsion before dilution with water. Add to the mixture. Tests conducted by the inventors have shown that the compounds of the present invention It is an effective reversal agent for such emulsions. Compounds within the invention for this end use of formula (Ia), although the particular choice depends on the particular operating conditions. Compounds in which m is 2, n is 8 to 25, especially 10 to 15, and R2 is H or C1 ~C6 alkyl groups, especially methyl, ethyl, propyl or butyl groups, are particularly preferred. The present inventors have found that this method is effective.

The amount of surfactant used to invert such emulsions will depend on the emulsion characteristics. It depends on the proportion of the aqueous phase dispersed in the aqueous phase and the concentration of the polymer in the aqueous phase. General Amounts of water-in-oil emulsions ranging from 1 to 5% are typical.

Therefore, the present invention provides compounds of formulas (1) and (II) in a water-in-oil emulsion. In particular, compounds of the formula (Ia), in particular m is 2 and n is 8 to 25, especially 10 to 15; Maybe R2 is H or a C,-C6 alkyl group, especially methyl, ethyl, propyl or butyl the water-in-oil emulsion is subsequently diluted with water. A water-in-oil emulsion inversion containing polyacrylamide in the aqueous phase consisting of The present invention also includes a polyacrylamide water-in-oil emulsion reversing agent. This includes the use of the compounds of the invention as.

The following examples describe the preparation and properties of the compounds of the invention and their end uses. The present invention is illustrated in detail to illustrate the versatility and uses of the compounds of the present invention. All parts and percentages are Unless otherwise specified, parts and percentages are by weight.

X Yuri Kasa Cloud point (CP) Measured according to ASTM D 2024-65. The result is in °C.

Wetness (Wtg) Draves wetness skein test (ASTMD 2) 281-58); results are seconds (s) [or minutes (+n) - slow About arrogant humectants].

Foam height PH) Ross Miles foam height 60°C ASTM D 117 It was evaluated from 3 to 53; the results are in mm.

Surface tension (ST) Surface tension was measured on a 0.1% w/w solution by the drop method at 23°C; The result is mN, m-', AmN1m-' = 1 dyne, cm-').

Mu SEI~5E24 Alkenyl succinic anhydride and polyethylene glycol ( PEG), alkyl polyethylene glycol ether or amine derivative of the invention by reacting a stoichiometric mixture and heating the mixture to about 100°C. Various compounds were formed. Measured by infrared spectroscopy and/or acid value of the mixture Samples were taken every 30 minutes until the reaction was complete as specified.

The corresponding sodium salt is prepared by adding NaOH solution to the acid product until the pH rises to 9. The sodium salt formed by 9 is then isolated by extrusion or dissolved in water. It was used as a solution.

The corresponding methyl ester was formed by addition of sulfuric acid and methanol. methanol The capacity is fixed for 2 to 12 hours Special Table 1,7-50854G (7) Distilled sodium bicarbonate is then added during the reaction in such a proportion that the The sulfuric acid was neutralized and the product was filtered. Different lower alcohol esters are the corresponding method It was formed by

Comparative substances with similar structures were also prepared using the general method described above, except for substituting appropriate raw materials. Prepared. These comparative examples are identified by the prefix "C" before the number.

Various properties of the compounds were determined and the results are given in Table 2 below. For further illustration Commercially available nonylphenol ethoxylate (1 mole of phenol) Table 2 with reference symbol "NPE" be included in

The basic properties of compound SEI are as follows: Surface tension (0.1% w/w solution) (Dripping method at 23℃) mN, +n-' 28.4 Pour point ('C)-15 Viscosity (CI) S/25°C) 165 foam height) 0 minutes 5 minutes (Ross Miles at 60°C) 7.5 3 density (g-crn-31 at 23°C, 006 wetness (Drabesu seconds) 10.5 seconds Cloud point ('C) 40-53 -Table-1- Integer values for 20 may be approximate values; this table for compounds of formula (II) The value of n'' is n+p (where p=m) in formula (II) as described above.

, AE1 to AE4 , AEl-ri1-- Semi-aqueous cleaning, for example, involves cleaning metal parts with a solvent followed by a rinsing process with water. terpene-derived solvents are often used in this application, with surfactant A sexing agent can be added to facilitate removal of solvent from the parts being cleaned during the water rinse process. Wear. Such surfactants or rinse aids meet two standards as they are known: First, the surfactant must have good solvent removal. Moreover, it must be soluble in the cleaning solvent.Secondly, the surfactant must be soluble in the solvent and water. should not be used to stabilize mixtures with prevent effective separation of compounds. I), Substances A and B below are semi-aqueous cleaning formulas It possesses desirable surfactant properties to make it a useful rinse aid in formulations. these is also soluble in terpene solvents. Surprisingly, these surfactants A faster and more effective solvent compared to other surfactants commonly used for this application Tests have shown that it exhibits separation between water and water.

The following experimental data illustrates this effect. 0.6% surfactant and 9.4% The mixture of terpene solvent and 98% water was mixed in a graduated cylinder five times. This was manufactured from The mixture was allowed to stand at room temperature for 20 hours.

During this period, periodic evaluations of the degree of phase separation were carried out, and the following table records the results obtained. Ru.

Surfactant Appearance after 20 hours Commentary None. Both phases are clear. After 0.5 hours, complete separation of CIO alcohol, 3 EO oil phase and Both water and water phases are turbid. Separation is incomplete even after 2α hours. Complete separation means 10% of the total volume. 90% oil phase and 90% water phase.

, AEl- 10 20g samples of wool were mixed with 0.1 wt/w of surfactant in water (IQ) at 60°C. % solution was successfully washed in the same water bath. Residual grease in the last sample to be washed extracting the base with an organic solvent, typically dichloromethane or chloroform. It was measured from The results are explained in the following table: Product Residual Grease (%) “SYNPERONIC” NF2 (Korea) 1.71 “Syn Peronic "87K (") 2.16SE1 1.24 U commercially available CI3~cis alcohol alkoxylate umbrella commercially available Nonylphenol ethoxylate, available as Containing 4% by weight of KCΩ (to simulate salt accumulation during repeated use of the scouring solution) Another test of wool scouring with a surfactant loading of 0.5 g-Ω-1 in the aqueous scouring solution. was carried out using fine merino wool (fibers with a diameter of approximately 20 μm).

The scouring was operated at 65°C in the scouring detergent bowl and at 50°C in the rinse bowl.

Reuse the scouring solution multiple times and record the weight percentage of wool wax remaining on the wool after each treatment. The results are recorded and shown in Table 3 below. The SEL product was mixed with four other scouring surfactants. compared; gn Product name Supplier Characteristics C4 Rizapol BD20 ICI Australia Biodegradable wool scouring agent C5 Riza Pono, BD30 ICI Australia Biodegradable Wool Scouring Agent Table 3 Results The results show that the compounds of the present invention function well as wool scouring agents and, in particular, Even in processing wool, which is known to be difficult to scouring, current scouring agents shows good retention of performance when compared with

, AL! - Bo 1 Aku 1 Lua q゛ Emulsion anti-( Commercially available under the trade name “HYPERMER” 2296 By heating to about 40°C using a polymeric surfactant as the primary emulsifier. The following mixture was polymerized.

Acrylamide 135.0g Acrylic acid 5!1.0g Desalinated water 179.0g Hydrocarbon solvent (Isovar L) 168.6g Sodium hydroxide up to pH 6 Ethylenediaminetetraacetic acid (EDTA) (5%) 5.2g azobisisobutyro Nitrile (AIBN) 0.4g Main emulsifier 8-12g Add 3% of each of the following surfactants to a sample of polymer emulsion as an inverting agent: and the mixture was allowed to stand for 2-3 days. A sample of the emulsion is then taken and water A 1% formulation was formed. The viscosity was measured after stirring for 2 minutes. Then stirring was continued. The viscosity was measured again after 15 minutes. The measured viscosity is as follows; viscosity (mPa, s) 2 minutes later 15 minutes later “Synperonic” NF2 12000 26000SE1111500 26 000 SE19 24000 24500 C3 aggregated - These results indicate that 5EII is a common reversal agent "Synperonic" N Compound C3 is equivalent to F2, 5E19 is better, and compound C3 as a reversal agent. It didn't work effectively.

Submission of translation of written amendment (Article 184-8 of the Patent Law) December 26, 1994

Claims (12)

[Claims] 1. The following formula (I) or (II); Y. A1. O.C. (HR)C. C (HR1). C.O. A. (CmH2mO)n. R2(I) [In the formula, one of R and R1 is a C6-C22 alkenyl or alkyl group and the other is hydrogen; A is -O- or -NR4- (wherein R4 is hydrogen or a C1-C6 alkyl group) And; n is 2 to 100; m is 2 or 3 (and can vary with the polyoxyalkylene chain); R2 is hydrogen or a C1-C6 alkyl group; A1 is -O-, -O- or -NR 4- (wherein R4 is hydrogen or a C1-C6 alkyl group); thus A1 When is -O-, Y is a cation; and When A1 is -O- or -NR4-, Y is a C1-C6 alkyl group (R3) or is the following formula (CmH2mO)n. R2 (however, m, n and R2 are individually as described above) is the basis of However, when A is -O- or A1 is -O-, the groups R, R1 and any group R2 and the total number of carbon atoms in R3 is at least 13; or Y. A1. O.C. (HR)C. C (HR1). C.O. A. (CmH2mO)n. CpH2p. A. C.O. (HR1)C. C(HR)CO. A1Y(II) [In the formula, n, m and each R, R1, A, A1 and Y are individually as described above; and p is 2 or 3). 2. One of R and R1 is a C14-C22 alkenyl or alkyl group, and the other The compound according to claim 1, wherein is hydrogen. 3. The following formula (Ia); (Ia)Y. -OOC, (HR)C. C (HR1). COO. (CmH2mO) n. R2 [wherein m, n and R2 are as defined in claim 1; Y is one of R and R1 is a C14-C22 alkenyl or alkyl group. The compound according to claim 1, wherein the other is hydrogen. 4. The following formula (Ib); (Ib)Y. OOC. (HR)C. C (HR1). COO. (CmH2mO)n ．． R2 [wherein R, R1, m, n and R2 are as defined in claim 1; Y is a C1-C6 alkyl group or the following formula (CmH2O)n. R2 (however, m, n and R 2 is individually as defined in claim 1). A compound according to claim 1. 5. The following formula (Ic); (Ic)Y. -OOC. (HR)C. C (HR1). C.O. N.H. (CmH2m O) n. R2 [wherein R, R1, m, n and R2 are as defined in claim 1] and Y is a cation]. 6. The following formula (Id); (Id)R2. (CmH2mO)n. N.H. O.C. (HR)C. C (HR1). C.O. N.H. (CmH2mO)n. R2 [wherein R and R1 and each of m, n and R2 is individually as defined in claim 1. 1. The compound described in 1. 7. One of R and R1 is a C14-C22 alkenyl group, and the other is hydrogen A compound according to any one of claims 4 to 6. 8. n is 2; If p exists, it is 2; n is 3 to 50 and Y is a cation, i.e. H+, an alkali metal cation or an ammonium cation; Alternatively, it is a methyl, ethyl or butyl group according to any one of claims 1 to 8. Compound. 9. Wool containing wool wax is prepared by formula (I) as described in any one of claims 1 to 8. ) or (II) in an effective amount. , a method of treating wool to remove wool wax. 10. The compound has the formula (Ia) (where m is 2, n is 3 to 10, and R2 is C1 The method according to claim 9, wherein the compound is a C6 alkyl group. 11. Formula (I) as defined in any of claims 1 to 8 in a water-in-oil emulsion ) or (II), followed by dilution of the water-in-oil emulsion with water. In oil containing polyacrylamide in the aqueous phase, How to invert a water emulsion. 12. The compound has the formula (Ia) (where m is 2, n is 8 to 25, and R2 is H or C 12. The method according to claim 11, wherein the compound is a 1-C6 alkyl group.