HK1134281A - Urea-, glycerate-and, hydroxyamide-headed hydrocarbon chain lytotropic phases forming surfactants - Google Patents

Description

Urea, glycerate and hydroxylamine headed hydrocarbon chain lyotropic phase forming surfactants

The present invention is a divisional application of the invention patent application having the filing date of 2003, 9/4, application No. 03824437.3, entitled "surfactant for lyotropic phase formation of hydrocarbon chain having a head group of urea, glycerate and hydroxylamine".

Technical Field

The present invention relates to novel surfactants and to novel surfactants capable of forming inverse lyotropic liquid crystalline phases in aqueous solutions.

Background

Surfactants are amphiphilic compounds that contain a polar region, whether charged or uncharged, and a hydrocarbon or fluorocarbon non-polar region. In linear surfactants, the hydrophilic polar and hydrophobic non-polar regions are generally defined as head and tail groups, respectively.

Due to the amphiphilic nature of these materials, the head group is usually bound to some polar solvent such as water, while the tail group is bound to a hydrophobic substance such as the hydrocarbon tail of an oil, or other surfactant molecule. Thus, in mixtures of surfactants with water and other ingredients, the surfactants are usually present at the interface of the hydrophilic and hydrophobic regions, as this is a positively favourable environment. This surface activity has led to the discovery that these hydrophilic compounds can be used as surfactants and have a shrinking effect.

The addition of water to the surface-active substance can incorporate water molecules into the substance structure, and the water molecules are attached to the head group. The addition of water to the smoothing surfactant increases the fluidity of the hydrophilic regions of the mixture, thereby allowing the natural structure of the surfactant molecules to determine the orientation and spatial orientation of the molecules at the interface. This arrangement is commonly referred to as "bending" because the interface will bend toward the water or oil phase portion depending on the relative volumes of the head and tail portions of the molecule and the relative volumes of water and surfactant. The addition of a greater amount of water to the surfactant can change the average curvature within the system, thereby allowing a particular geometry to be achieved when an equilibrium system is reached. In equilibrium, these particular geometries are often defined as "mesophases", "lyotropic phases" or simply "phases".

The disordered combination of surfactant moieties in an ordered phase, ordered moieties, can produce classical liquid crystalline materials, and these phases are often referred to as liquid crystalline phases. In these phases, most crystalline solids exhibit disorder and surfactant molecules are able to move, unlike molecules within solid crystals. One therefore generally attributes these system types to liquid crystals. The liquid crystal phase formed in a mixed solution of an amphoteric compound and a solvent (usually water) is also referred to as "lyotropic liquid crystal phase".

In addition, if the mean curvature of the surfactant-solvent system is lipophilic, the mesophase is usually defined as the "continuous aqueous phase" and is considered to be the "normal" type phase. If the curvature is hydrophilic, the mesophase of the system is defined as the "continuous oil phase" and is considered to be the "reverse" or "inverse" type phase. If the curvature is represented as being in-between, the average curvature of the system approaches zero and the resulting phase assumes a lamellar structure, or a structure generally defined as a "bicontinuous phase" consisting of two intertwined, continuous hydrophilic and hydrophobic regions.

Examples of specific geometries that can be formed in the surfactant-solvent system are reverse micellar phase, reverse hexagonal phase, lamellar phase, reverse cubic phase, bicontinuous cubic phase, normal hexagonal phase and micellar phase. In these examples, micelles are formed because the hydrophobic regions formed by the head group binding to water and the tail group binding to other tail groups cause the surfactant molecules to self-assemble into aggregates. Normal micelles comprise a center formed by a hydrophobic tail surrounded by a head-based shell extending into the water molecule into which the head-based extends.

Further addition of water to the system dilutes the micelles, and depending on the solubility of the surfactant molecules in water, either too much or too little will result in polymer scission, forming monomeric surfactant molecules in water. The addition of water insoluble oils to the system will cause some of the oil to become embedded in (or dissolved in) the hydrophobic core of the micelle until the core is filled with the material. The subsequent addition of an oil to the system promotes the formation of a separate oil phase outside the micellar solution, and the system will be in a separate phase. Reverse micelles are very similar to normal micelles, except that the inner core of the reverse micelle contains water, linked to the head group, and the tail group extends into the continuous hydrocarbon phase region. Adding oil substance to dilute the discontinuous micelle, and adding water to expand the micelle until the water-solubility of the micelle inner core is exceeded, so that phase separation is generated. The micelles themselves may be spherical, rod-like or disk-like, depending on the molecular geometry of the surfactant, but when the micelle concentration is sufficiently low, the system appears isotropic.

When the system consists of an extremely high concentration long rod-shaped micelle aqueous solution, a hexagonal phase appears, and is wrapped by a hexagonal array. Also this system has a two-dimensional structure. This increases the viscosity of the system and the anisotropic birefringent structure can be observed by using a microscope with crossed polarizing filters. And, the inverted hexagonal phase is the continuous oil phase of the normal hexagonal phase with the aqueous core micelles located in a tightly packed hexagonal array.

The lamellar phase is composed of a laminated two-layer structure in which reversed monolayers of head groups are phase-separated by aqueous regions to form hydrophilic layers, and tail groups of these back-to-back hydrophilic layers are in intimate contact with each other to form hydrophobic layers. This phase is present when the hydrophobic and hydrophilic regions are nearly equal in volume within the surfactant molecular structure.

The cubic phase is composed of two main types, namely a bicontinuous phase and a micellar phase. The normal and inverse cubic phases are micellar phases and, like hexagonal phases, they consist of tightly packed spherical micelles located within a cubic array in which water and head or tail groups form the interior of the micelle. Generally these cubic phases are of high viscosity, but since they are composed of spherical micelles, these systems exhibit isotropy and hence no anisotropic structure is observed. When the geometry of the surfactant molecules is balanced, a bicontinuous phase state is formed, and the curvature of the system is zero at this time. This results in a so-called "infinite periodic lattice structure" in which the hydrophobic and hydrophilic regions intertwine but do not intersect one another. For the purposes of the present invention, the bicontinuous phase should be classified as "inverse lyotropic phase", "inverse lyotropic multiphase", or "inverse liquid crystalline phase".

In the ordered lyotropic phase, a certain ratio of water to surfactant is added. In addition, when the amount of water added to the surfactant is increased, there occurs a typical continuation of the mesophase and there occurs a reverse micelle phase, a reverse hexagonal phase, a lamellar phase, a reverse cubic phase, a bicontinuous cubic phase, a normal hexagonal phase and a micelle phase. It is important to realize that upon dilution of a particular surfactant, not all phases are observed, but the ordering of the phases can be maintained.

For some surfactants, geometric constraints may result in the failure to form a normal phase at all. In this case, the antisolvent or lamellar phase undergoes swelling when a certain amount of water is added, and when this amount of water is exceeded, water molecules will not be inserted into the surfactant molecules and phase separation will occur. The phase that appears in these cases is an equilibrium phase with excess water and is the "dilution has reached steady state". In these systems, it is theoretically possible to break the water-saturated lyotropic phase into a dispersion of particles in the colloidal size range.

In lamellar phases containing excess water, energy is imparted to the system to break the bilayer structure into segments whose "ends" can be connected to each other to form spherical bilayer particles, containing water inside the bilayer spheres. These particles are generally defined as vesicles. If the bilayer material is an oil such as diacylphosphatidylcholine, it is generally defined as a liposome. Depending on the amount of energy administered to the system and the method of manufacture, multilamellar vesicles and/or unilamellar vesicles can be formed in solution. These types of systems are very common and, depending on their membrane-like structure, can serve as carriers for many intracellular processes. However, not only can the formation of these structures be demonstrated by endogenous substances, but many synthetic surfactants with similar molecular structures can also form lamellar phases that can be stably diluted.

Less commonly, the surfactant forms a true inverse phase, such as a reverse hexagonal phase, or a cubic phase, which also allows for stable dilution. Similar to the diacyl phosphatidylcholine system, diacyl phosphatidylethanolamine with a certain diacyl chain length can also form an inverse hexagonal phase, and then stable dilution is carried out. It has been reported that glycolipids with two cellulosic lipid chains also form an inverted hexagonal phase in the presence of excess water. In these cases, the water-saturated phase inversion can be interrupted to form hexagonal phase particles that are stable in excess water, and these particles are defined as hexagonal structures.

It is less common that the surfactant forms a bicontinuous cubic phase that is stable in excess water. Glyceryl monooleate is one such surfactant, as is phytantriol. The water-saturated bulk phase dispersion may be dispersed by imparting energy to form a dispersion of particles that is stable in excess water. The particles in this case are defined as cubic structures.

It is noted that these dispersed particles, i.e. liposomes, hexagonal structures, cubic structures, are not thermodynamically stable and will gradually condense back over time to a bulk phase separated from the inverse phase and an excess of water. This phenomenon can be prevented in some cases by adding a surface stabilizer, so that the particles can be prevented from coagulating.

The formation of the normal phase by using a surfactant is many cases, and mainly includes detergency by dissolution of oil-containing soil or by surface modification of a substrate, lubrication, formation and stabilization of foam, emulsion stabilization, and wetting of powder for the convenience of production and improvement of dissolution rate.

The viscosity of the anti-lyotropic phase is generally very high, a property that makes these materials particularly useful in applications where immobilization of a particular agent is important. The phase behavior can be controlled by small changes in system composition or other variables such as temperature to obtain a low viscosity phase, a property that indicates that ingredients prepared from these types of surfactants are very useful. Surfactants capable of generating an anti-lyotropic phase can be used stably in excess water, especially in processes where dilutability is an important aspect. Also, the anti-lyotropic phase can be applied in the biomedical field, i.e. using the glycerol monooleate cubic phase to immobilize membrane proteins. However, for some systems, it is necessary to study membrane proteins that do not match the size of the cubic phase formed by glycerol monooleate. In addition, the range of operating temperatures for glycerol monooleate systems is limited, which limits the range of applications for such systems.

Disclosure of Invention

The present invention is based on the discovery of novel surfactants that form an anti-lyotropic phase in aqueous solution. Such lyotropic phases may be micellar phases, or various liquid crystalline phases such as inverse hexagonal phases, bicontinuous cubic phases. Basically, the formation of the anti-lyotropic phase is due to the structural function of the amphiphilic molecule. Especially amphiphilic molecules with relatively small polar head groups and wedge or cone-shaped tail groups in solution tend to form an anti-lyotropic phase in excess aqueous solution.

Accordingly, the present invention provides a compound containing, as a head group, a group consisting of any one of the following structures (I) to (V):

and the tail group is selected from the group consisting of a branched alkyl chain, a branched alkoxy chain or an alkenyl chain, wherein

In the structure (I)

R²is-H, -CH₂CH₂An OH group or other tail group, or a combination thereof,

R³and R⁴Is one or more selected from the following groups respectively: -H, -C (O) NH₂、-CH₂CH₂OH、-CH₂CH(OH)CH₂OH，

In the structure (II)

X is O, S or N, and the formula is,

t and u are each 0 or 1,

R⁵is-C (CH)₂OH)₂Alkyl, -CH (OH) CH₂OH (if the tail group is not oleyl), -CH₂COOH、-C(OH)₂CH₂OH、-CH(CH₂OH)₂、-CH₂(CHOH)₂CH₂OH、-CH₂C(O)NHC(O)NH₂，

In the structure (III)

R⁶is-H or-OH,

R⁷is-CH₂OH or-CH₂NHC(O)NH₂，

In the structure (IV)

R⁸is-H or alkyl

R⁹is-H or alkyl.

The tail group is preferably selected from:

wherein n is an integer of 2 to 6, a is an integer of 1 to 12, b is an integer of 0 to 10, d is an integer of 0 to 3, e is an integer of 1 to 12, w is an integer of 2 to 10, y is an integer of 1 to 10, and z is an integer of 2 to 10.

The present invention also provides a surfactant capable of forming an anti-lyotropic phase in an excess of aqueous solution, the surfactant comprising a head group selected from the group consisting of any of the following structures (I) to (V):

and the tail group is selected from the group consisting of a branched alkyl chain, a branched alkoxy chain or an alkenyl chain, wherein R is in the structure (I)²is-H, -CH₂CH₂An OH group or other tail group, or a combination thereof,

R³and R⁴Is one or more selected from the following groups respectively: -H, -C (O) NH₂、-CH₂CH₂OH、-CH₂CH(OH)CH₂OH，

In structure (II) X is O, S or N,

t and u are each 0 or 1,

R⁵is-C (CH)₂OH)₂Alkyl, -CH (OH) CH₂OH (if the tail group is not oleyl), -CH₂COOH、

-C(OH)₂CH₂OH、-CH(CH₂OH)₂、-CH₂(CHOH)₂CH₂OH、-CH₂C(O)NHC(O)NH₂，

In structure (III) R⁶is-H or-OH,

R⁷is-CH₂OH or-CH₂NHC(O)NH₂，

In structure (IV) R⁸is-H or alkyl

R⁹is-H or alkyl.

The tail group is preferably selected from:

wherein n is an integer of 2 to 6, a is an integer of 1 to 12, b is an integer of 0 to 10, d is an integer of 0 to 3, e is an integer of 1 to 12, w is an integer of 2 to 10, y is an integer of 1 to 10, and z is an integer of 2 to 10.

Under appropriate conditions, the surfactants of the present invention are capable of forming a thermodynamically stable, anti-lyotropic phase in excess water. The lyotropic phase formed is preferably selected from the group consisting of an inverse micellar phase, a bicontinuous cubic phase, an inverse mesogenic liquid crystal phase and an inverse hexagonal liquid crystal phase. The inverse lyotropic phase formed is preferably a bicontinuous cubic liquid crystal phase or an inverse hexagonal liquid crystal phase. These phases are characterized and confirmed in the field of liquid crystal phase morphology of surfactants.

The invention also provides a mixture comprising an anti-lyotropic phase formed from the surfactant of the invention. The anti-lyotropic phase may be present in the form of colloidally dispersed particles and, thus, the present invention provides a colloidal particle consisting of a micellar or liquid crystalline form of the anti-lyotropic phase formed by the surfactant of the present invention.

Detailed Description

The discovery of novel urea compounds prompted the present invention to enable the formation of an anti-lyotropic hexagonal phase in excess water at high temperatures. The present invention is also based on this finding and continues through the work in the present invention such that these phases can be formed also at low temperatures. The formation of reverse micellar phase, reverse hexagonal phase or cubic phase at low temperature allows the formation of solutions containing stable reversed phase state at ambient temperature, which can be applied in industrial production.

The invention synthesizes a plurality of urea, glycerate and hydroxylamine head-group surfactants and researches the behavior of the surfactants in aqueous solution. When a novel compound with different phase behaviors is screened, the melting point of the pure compound has a certain relation with the temperature range of the reverse phase of the pure compound formed in water. In particular, the lower the melting point of the pure compound, the lower the temperature at which the phase inversion forms. Those surfactants which form an anti-lyotropic phase in water at temperatures below 150 c are considered by the industry to be most suitable for use, although many surfactants and anti-lyotropic phases are not formed only in the optimum temperature range in the present invention.

In the present invention, both surfactants with any of the head groups given in table 1 were synthesized and demonstrated to have a particular morphology, and an anti-lyotropic phase was formed in excess water based on the data obtained from these synthetic surfactants.

TABLE 1

The surfactants of the present invention can be synthesized by known industrially available starting materials by employing known methods, or can be prepared using standard techniques of organic chemistry, and the resulting surfactants can be used to prepare the relevant compounds indicated in the literature.

For example, urea head-based surfactants can be prepared by first combining an amine and a selected tail group and then reacting with an alkylamine to form a derivative. Glycerol derivatives can be prepared by reacting the appropriate organic acid with glycerol as an alcohol; regiospecific associations can be made by protecting and deprotecting different alcohol groups to produce surfactants. Glycerate derivatives can be prepared by treating active glyceric acid with an alcohol containing the tail group of interest.

The above reaction may take place at different temperatures, depending on certain conditions such as the solvent used and the solubility of all reactants and intermediates. However, when the above reaction is employed, the reaction preferably occurs at a temperature in the range of 0 to 100 ℃ and the reaction at room temperature is more preferred. The time required for the above reaction also varies within a relatively wide range, and factors affecting their specific reaction time are the same as those described above. But the reaction will usually be completed in 5 minutes to 24 hours.

The product is isolated from the reaction mixture by conventional techniques such as precipitation, extraction with immiscible solvents at appropriate pH, evaporation, filtration, crystallization or by liquid chromatography on silica gel or the like. However, it is common practice to isolate the product using crystallization or silica gel liquid chromatography, and if desired, to continue further purification by reverse phase HPLC.

The precursor compounds can be prepared using methods known in the art. Other variations and modifications of the present invention using the synthetic routes described above will be apparent to those skilled in the art.

It is generally believed that the surfactants of the present invention are capable of forming cubic or inverted hexagonal phases in excess water by combining a relatively small polar head group with a wedge-shaped molecular structure tail group. Branched alkyl chains, for example with (3, 7, 11-trimethyl) -dodecane (hexahydrofarnesol) and (3, 7, 11, 15-tetramethyl) hexadecane (phytanol), appear to be particularly useful for the purposes of the present invention. Aliphatic chains containing one or more cis double bonds, such as oleyl or linoleyl chains, have also been found to be useful as a tail group.

The phase behavior of a selected compound was initially assessed by the "immersion" technique. The submersion technique refers to placing the compound between a cover slip and a microscope slide and adding water to the sample to form a sample water concentration gradient. The technique has been described in detail in the technical field relating to the determination of the type of lyotropic phase formed by a surfactant in an aqueous solution and the discrimination of the order of phases when increasing the water content, but the technical field of the technique in the determination of the water content at the phase boundary lacks details. If the experiment is carried out at elevated temperatures, the temperature range in which a particular lyotropic phase occurs can be determined. Phase behavior can be observed using an optical microscope under normal or cross-polarized light conditions. It will be apparent to those skilled in the art that the type of phase can be distinguished by the unique structure observed under cross-polarized light and the order of the phases observed through the sample. For the present invention, it is particularly useful to identify the type of phase that exists at the boundary under excess water conditions.

In addition to this basic screening method, there are two methods for characterizing phase boundaries by composition. The first method is to mix the surfactant and water in a known ratio, seal the mixture in an ampoule, and measure the phase or phases formed at equilibrium. The second method is to perform a soaking experiment while performing near infrared measurement of the water content at different points of the concentration gradient, which are related to the phase type.

Further structural evaluation of the hexagonal or cubic phase of the lyotropic phase can be performed using a small angle X-ray diffractometer (SAXS), or by observing the fractional structure by an optical microscope and an electron microscope, such as cryo-TEM (transmission electron microscope), nuclear magnetic resonance, or by measuring particle size dispersion using light scattering, or by differential scanning calorimetry, or by a combination of two or more of the above techniques. In most cases, structural assessment can be made of the total sample of the lyotropic phase and the colloidal dispersion of the total lyotropic phase.

The present invention relates to binary and pseudo-binary systems in which, in the case of binary systems, a surfactant is intermixed with a polar liquid such as water, while in the case of pseudo-binary systems, other water-soluble or oil-soluble components may be present. Ternary systems can also be obtained by adding a non-polar solvent to the surfactant-water mixture. It will be appreciated that the surfactants of the present invention may in some cases form the lyotropic phase of a two-phase system, whereas the lyotropic phase can only be formed in a three-phase system using existing surfactants.

Mixtures containing the lyotropic phase formed by the surfactants of the present invention may be prepared with water as the hydrophilic liquid. These mixtures may also contain additives such as, but not limited to, stabilizers, preservatives, colorants, buffers, cryoprotectants, viscosity modifiers, other surfactants described herein, and other functional additives.

Advantageously, the inverse phases diluted in excess aqueous solution have thermodynamic stabilities indicating that they can be dispersed, thereby forming colloidal particles of the anti-lyotropic phase. Colloidal particles containing a cubic phase or a hexagonal phase are sometimes also referred to as a cubic structure and a hexagonal structure, respectively. In these phases, the non-polar tail group of the surfactant comprises the inner hydrophobic domain of the anti-lyotropic phase, while the hydrophilic group is present at the interface between the hydrophobic domain and the inner and outer aqueous domains.

The mixtures of the present invention may be prepared by any suitable process. However, the process preferably includes a step of melting the surfactant, and if necessary, may include a step of homogenizing the melted surfactant in an aqueous medium. Alternatively, the mixture may be prepared by adding a liquid component to a molten substance, a liquid containing no solute or a liquefied surfactant.

The anti-lyotropic multiphase state may comprise a solute compound contained in the anti-lyotropic phase. In this case, the solute may be present within hydrophobic domains, hydrophilic domains, inverse interface domains, or dispersed between different regions by artificial or natural diffusion processes. If the solute is an amphipathic molecule, it may be present in one or more of these regions simultaneously. Importantly, it is a particular advantage that solutes can be loaded into different regions when using the surfactants of the present invention.

Such solvents include, but are not limited to, diagnostic agents, polymeric monomers, polymerization initiators, proteins and other polypeptides, oligonucleotides, denatured and non-denatured DNA, radiotherapeutic agents, sunscreen actives, transdermal agents, dermatological agents, transdermal active compounds, transmucosal active compounds, skin repair agents, wound treatment compounds, skin cleansers, degreasers, viscosity altering polymers, hair care actives, agrochemicals such as fungicides and insecticides, fertilizers and nutrients, vitamins and minerals, explosives or explosives and mixtures, mining materials, paper and cardboard surface coating materials.

In order for the compounds containing the anti-lyotropic phase to be industrially useful, the phase and the colloidal particles need to be preserved for a prolonged period of time at the storage temperature. By "stable" is meant that the anti-lyotropic phase does not undergo deleterious phase changes due to storage conditions or chemical degradation. Also, these phases must be kept in line with other processes to enhance stability, including gelation of the solidified or surrounding medium, freezing, freeze-drying or spray-drying. In addition, the reverse phase can be generated by adding a precursor solution containing surfactants and other mixtures such as hydrotropes to the aqueous phase, which is considered to be one approach to solving the stability problem. An additional consideration regarding phase stability is that the phase must be stable at the operating temperature. The working temperature is of course dependent on the use of the anti-lyotropic phase. For convenient storage, the lyotropic phase is preferably stable at room temperature.

In terms of stability, the use of surfactants with higher transition temperatures is particularly advantageous because solidification by lowering the temperature below the temperature at which the anti-lyotropic phase is produced can result in a restriction of the aqueous phase area and water-soluble solutes within the solid matrix. This solid matrix will make the system more stable. Upon heating to the transition temperature, the anti-lyotropic phase reforms, thus enabling the function and dispersion of the anti-lyotropic phase to be achieved in the application.

The anti-lyotropic phase in the present invention is preferably produced at a temperature in the range of-100 to 150 degrees celsius.

In the phase formed by the surfactants of the present invention, the bicontinuous cubic phase has a structure in which the bi-surfactant layer separates the internal aqueous phase region from the external aqueous phase region. The two-layer film is multiply folded and connected to each other. The hexagonal phase consists of rod-like micelles, encapsulated in a hexagonal array within a surfactant matrix. These structures have been well understood and described in literature relating to surfactant phase behavior.

The particular geometry of the surfactants described in the present invention determines the type of arrangement that the surfactant molecules adopt at the interface of the hydrophilic and hydrophobic regions and the resulting thermodynamically stable phase. There is some close relationship between the formation of lamellar phases and bicontinuous cubic phases, and as water content increases, the latter is usually observed as an intermediate phase between the former and some more hydrophilic water-rich phase. However, the surfactants of the present invention are less soluble in water and therefore do not convert to a more hydrophilic phase as the water content increases. Instead, the excess water is not able to enter the phase at all, but is in a separate region from the phase. Also, for the inverted hexagonal phase, there is no transition to a more hydrophilic phase because the water in the hexagonal phase undergoes only limited swelling, while the low solubility of the surfactant in water causes the excess water to additionally form an aqueous phase rather than transition to a more hydrophilic homogeneous system.

This gives the surfactant according to the invention the property that the antisolvent phase or bicontinuous cubic phase will be present in excess water and will not undergo a phase change process upon dilution.

Most of the surfactants described in the present invention can form an anti-lyotropic phase by natural contact with water at room temperature. Generally, as the temperature increases, the cubic phase or the inverse hexagonal phase begins to slowly dissolve and the fluidity within the phase state increases. After continued heating, the sample finally reaches a temperature at which all liquid crystal structures will be destroyed, resulting in an isotropic surfactant-rich phase and the generation of excess water. Generally the cubic or inverse hexagonal phase will typically reproduce after cooling and at the reproduced temperature of this cubic or inverse hexagonal phase the phase supercooling phenomenon is evident.

A problem with some liquid crystal phases is that the phase change occurs upon dilution of the solution. In many practical applications, it is desirable that the phase state remains stable, i.e. does not undergo a phase change upon dilution with a solvent. It has now been found that the liquid crystal phase formed by the surfactant according to the present invention does not undergo a phase change upon dilution with a solvent.

The phase prepared according to the invention exists in the following two basic forms, although it may be necessary to produce other forms depending on the application.

The first form is bulk inversion, in which the entire aqueous phase composition may or may not be incorporated into the anti-lyotropic phase. The bulk phase is prepared by simply mixing the surfactant component containing any desired solute with the aqueous phase component in a mixer, blender, jet mixer, homogenizer, or the like. The use of cosolvents, which are subsequently partially or completely removed by natural or vacuum evaporation, or by heating or other methods, will help to simplify the preparation of the full reverse phase. In addition, if desired, the solvent may be retained as part of the system. Temperature control can also be used to change the phase behavior of the mixture and thus its rheological properties to accelerate the mixing process.

The second form is the case where an excess of aqueous solution is added to the mixture. Because the full reverse phase remains stable upon dilution with excess water, it is possible to obtain reverse phase particles dispersed in aqueous solution.

Two basic methods can be used to disperse the anti-lyotropic phase in the aqueous phase, i.e., breaking up the homogeneous bulk phase or dispersing a surfactant in the water to generate a liquid crystal structure in situ. This fragmentation process is a bulk reverse phase preparation under sufficient aqueous phase conditions to form a substantially lyotropic phase free of excess water. Any solute may be selected for incorporation into the liquid crystal phase, either soluble in the hydrophobic surfactant component or soluble in the hydrophilic aqueous phase solution. The bulk phase is then added in reverse to the second aqueous phase solution, which may or may not differ from the aqueous phase used to form the preliminary lyotropic phase and the homogeneous mixture formed in the high energy mixer. Coarse dispersion is then carried out by means of a high-pressure homogenizer to further reduce the size of the dispersed particles. In use, the homogenization conditions may be self-defined to achieve the desired average particle size; average particle sizes on the submicron scale, typically less than 200 nm in diameter, can be obtained by this process. In some cases, temperature control of the process is also important, and can be controlled by a heat jacket device.

The particles of the anti-lyotropic phase may also be prepared in situ by licking surfactants, possibly dissolved in some suitable hydrotrope, into an aqueous solution under high shear mixing to form a coarse dispersion. In some cases, the selection of the hydrotrope helps to reduce the energy required to obtain stable coarse dispersion. The step of reducing the particle size may then be performed, in the same manner as described above. The quality of the dispersion and colloidal stability can be monitored by particle size analysis and observation of initial instability after storage over time under the conditions of interest.

In the present invention, the dispersion of the surfactant having a high melting point can be accomplished by the same method as described above, but special attention needs to be paid to the temperature control. For the dispersion of these surfactants, these surfactants need to protect the internal aqueous phase region of the particles at the appropriate temperature, but the use of these surfactants to release their contents at elevated temperatures is very important. Subsequent treatment of the mixture of the invention is required to make it applicable to the particular situation. For example, the mixture may be sterilized by an autoclave method, a sterile filtration method, or an ultraviolet irradiation method.

The colloidal particles or mixtures containing surfactants can be stabilized using a stabilizer. Various stabilizers commonly used in other colloidal systems to provide stabilization may also be used in the present invention. For example, poloxamers, alginates, pullulans and dextrans may be used to improve stability. The addition of the stabilizer preferably does not affect the final structure or physical properties of the particles or mixture. More importantly, the addition of the stabilizer does not alter the anti-lyotropic phase which is in contact with the excess water.

The mixture of the present invention can also be modified by adding additives to the aqueous medium without changing the basic structure of the particles, such as, but not limited to, glycerol, sucrose, phosphate buffer and appropriate concentrations of salts. The dispersed phase of the anti-lyotropic phase, including the bicontinuous phase, may be used in situations where large quantities of starting materials are present in an industrial process requiring pumping or handling, or in situations where very high surface areas are required such as in surface polymerization processes, or may be used as a reaction quenching agent.

The water-resistant nature of the phases formed by the surfactants of the present invention allows them to be used as water-resistant coatings or lubricants, which function to resist atmospheric and/or watery environments or to extend the useful life of such materials in such environments.

When used as a coating for paper and cardboard, it has a greater advantage than the currently used oil-based and wax-based coatings, or alternatively, it can be used as a carrier to carry the coating mixture more permanently. The dispersed phase of the present invention can be used by spraying, further adding to the advantages of these applications.

The formulation of explosives requires that organic solutions (as fuels) and aqueous solutions (containing water-soluble oxidizers) be able to be brought into intimate contact so that the use of these materials in explosive formulations in the mining industry is another use for these materials. This degree of contact is made more intimate with the use of the materials of the present invention than with currently used emulsifier formulations. The use of explosive agents often in particularly humid and humid environments is one aspect of the particular application of the materials of the present invention in the field of explosive agents.

Immobilization of enzymes and proteins within the structure of the anti-lyotropic phase is very useful because the internal environment of the anti-lyotropic phase can be controlled to reduce denaturation and degradation of solutes.

Wherein the reverse and disperse phases may also be used as biosensors, and the conversion mechanism may be detected by changes in the lyotropic phase in connection with binding to a target molecule or antigen. The small particle size and high dispersed phase surface area of these materials of the present invention make the present invention particularly attractive for use in polymerization, reaction control and crystallization control applications. In these applications, the ability to load reagents with different physicochemical properties into different phase regions is particularly important for these applications. As these materials of the invention are particularly useful for dispersing two or more reactants into different phase compartments, as well as for adding catalysts or promoters to the external aqueous solution. Alternatively, the catalyst may be added in a phase zone and the reactants then introduced via an external aqueous solution. In any event, this ability to act as a site for controlling the reaction or polymerization field makes the preparation of bulk lyotropic and disperse phases from these amphiphilic molecules very useful. The controlled crystallization of the material within the different phase partitions created by the present invention allows the sizing or restriction of the size and shape of the novel particles produced thereby.

The materials of the present invention may also be used in the field of cosmetics and hair and skin care products. Also, in these fields of application, a very important capacity to load reagents with different properties is obtained. The use of these materials in the present invention provides many potential advantages over the use of conventional materials for making creams, gels, foams, mousses, oil products, ointments and the like due to their good water resistance and potentially lower skin irritation. Similarly, the invention can be applied in the field of hair care, topical treatment against bacterial fungal infections and skin diseases such as psoriasis.

Since these materials can produce decomposition products with very low oral toxicity, they are also likely to be applied in the food field, such as emulsifiers, dispersants, jellies, jams and ice creams and cheese milk products. When these amphiphilic molecules are applied in a system as rheology and phase modifiers, they can achieve very interesting special rheological properties when added to water. Also, these materials can be used in vitamin and mineral supplement formulations and the like.

Best mode for carrying out the invention

The preferred embodiments of the present invention will be described by the following examples which are not intended to limit the scope of the present invention.

Example 1-1- (3, 7, 11, 15-tetramethyl-hexadecyl) -1- (2-hydroxyethyl) urea

Synthesis of

Chemical feature-element analysis

And (3) calculating the result: c71.82, H12.58, N7.28, O8.32 assay results: c71.48, H12.44, N6.81, O9.27

Chemical characterisation-NMR analysis

¹H NMR m, delta 0.78-0.93, 15H hexadecyl CH₃(ii) a m, delta 0.96-1.65, 24H hexadecyl CH₂+ hexadecyl CH; m, delta 3.15-3.27, 2H, CO₂-CH₂；t，δ3.39，J 4.85Hz，NHCH₂CH₂OH；t，δ3.76，J4.85Hz，NHCH₂CH₂OH；v br s，δ4.66 2H，N-H；v br s，δ5.351H，N-H

Physical Properties

The compound was a pale yellow oil at room temperature.

Lyotropic behavior

At 20 degrees celsius, the aqueous phase faced inward while a reverse hexagonal phase formed at the interface and continued to widen slowly over a sustained period of 20 minutes. Heating was continued and the hexagonal phase began to melt at 50.9 degrees celsius, turning into a flowable isotropic phase and the sample was fully isotropic when the temperature reached 58.1 degrees celsius. The flowable isotropic phase is maintained to a temperature of 100 degrees celsius. The sample was rapidly cooled and the hexagonal phase re-formed at 51.1 degrees celsius.

Example 2-1- (3, 7, 11, 15-tetramethyl-hexadecyl) -3- (2-hydroxyethyl) urea

Synthesis of

H₂Catalyst

Chemical feature-element analysis

And (3) calculating the result: c71.82, H12.58, N7.28, O8.32 assay results: c71.84, H12.77, N7.38, O8.01

Chemical characterisation-NMR analysis

¹H NMR m, delta 0.76-0.94, 15H hexadecyl CH₃(ii) a m, delta 0.94-1.60, 24H hexadecamethyl + hexadecCH groups; m, delta 3.03-3.23, 2H, CO₂-CH₂；t，δ3.30，J 4.7Hz，NHCH₂CH₂OH；t，δ3.66，J4.7Hz，NHCH₂CH₂OH；v br s，δ4.68 3H

Physical Properties

It is a colored oily substance at room temperature.

Lyotropic behavior

The surfactant can form a reverse hexagonal phase with water on an interface, and the temperature range of the surfactant is wide and the surfactant is completely dissolved from 8 ℃ to 58 ℃. Starting at 40.4 degrees centigrade, the inverse phase begins to melt slowly, forming an isotropic phase near the interface, which is more fluid and extends outward. The sample completely melted when the temperature reached 57.3 degrees celsius. Upon cooling to 44.1 degrees celsius, a reverse hexagonal phase recrystallizes.

Example 3-3, 7, 11, 15-tetramethyl-hexadecylurea

Synthesis of

Chemical feature-element analysis

And (3) calculating the result: c74.06, H13.02, N8.22, O4.70

And (3) analysis results: c73.79, H12.83, N8.11, O5.97

Chemical characterisation-NMR analysis

¹HNMRm, δ 0.78-0.93, 12H hexadecyl; m, delta 0.93-1.60, 24H hexadecamethyl + hexadecCH groups; m, delta 3.00-3.23, 2H, CO₂-CH₂；v br s，δ4.66，2H；v br s，δ5.35，1H。

Physical Properties

The compound can form thermotropic liquid crystal at room temperature, and is melted at 60.6-65.5 ℃.

Lyotropic behavior

At 25 degrees celsius, a reverse hexagonal phase forms along the interface of the surfactant and water with isotropic bands between these surfactants and surfactants that do not form a reverse hexagonal phase. When the temperature is maintained at 25 degrees celsius, the position of the phase separation interface with water cannot be moved. Fluidity can be observed on isotropic bands and the presence of small bubbles can be found within both mesophases. At 49.6 degrees celsius, the isotropic bands begin to replace the crystalline material and the process accelerates as the temperature increases. At temperatures up to 54.9 degrees celsius, the surfactant core appears isotropic. At 72.6 degrees celsius, the inverted hexagonal phase begins to melt into an isotropic liquid at the interface with water and melts completely at 82.1 degrees celsius.

Example 4-3, 7, 11-trimethyl-dodecyl Urea

Synthesis of

Chemical feature-element analysis

And (3) calculating the result: c71.06, H12.67, N10.36, O5.92

And (3) analysis results: c71.41, H12.38, N10.37, O5.84

Chemical characterisation-NMR analysis

¹H NMR m, delta 0.77-0.92, 12H dodecyl CH₃(ii) a m, delta 0.92-1.65, 17H dodecyl CH₂+ dodecyl CH; m, delta 3.15-3.27, 2H, CO₂-CH₂；v br s，δ4.662H，N-H；v br s，δ5.351H，N-H。

Physical Properties

A viscous intermediate liquid that is transparent at room temperature. The melting point of the liquid crystal is 61-62.5 ℃.

Lyotropic behavior

When water contacts the viscous oily surfactant at 30 ℃, the water enters the oil and a reversed hexagonal phase structure immediately appears on an interface in the oil, so that the water is prevented from entering the oil. The anti-lyotropic phase is clear and transparent at temperatures between 30 and 50 degrees celsius. At a temperature of 55 degrees celsius some dynamic effects appear at the interface with water, characterized by hexagonal phase fusion and regrowth. The melting and regrowth activities are obvious at the temperature of 60 ℃, and the reverse hexagonal phase is completely melted when the temperature is higher than 70 ℃.

Example 5 Octadecyl-9-Enyl 2, 3-dihydroxypropionate

Chemical feature-element analysis

And (3) calculating the result: c71.35, H10.55, O18.10

And (3) analysis results: c70.39, H10.92, O18.69

Chemical characterisation-NMR analysis

¹H NMR δ(CDCL₃) sl br t, δ 0.88, 3H, split 6.3Hz, oleylmethyl; m, delta 1.2-1.45, 22H oleylmethine; m, delta 1.55-1.75, 2H, CH₂CH₂CO₂；m，δ1.9-2.1，4H，CH₂CH＝CHCH₂；v br s^*，δ2.05-2.45，1H，OH；vbr s^*Delta 3.05-3.40, 1H, OH; dd, Δ 3.83, 1H, J-11.7Hz, glyceryl C3-H; dd, Δ 3.90, 1H, J-11.7Hz 3.3Hz, glyceryl C3-H; t, delta 4.22, 2H, J6.7Hz, oleyl CH₂O; dd, delta 4.26, 1H, J3.7 Hz 3.3Hz, glycerolA group C2-H; m, 2H, δ 5.3-5.4, CH ═ CH.^*In the passage of D₂After O treatment, the resonances at 2.2 and 3.2 disappeared.

Physical Properties

Partially crystalline wax at 23 degrees celsius. The viscosity decreased at 30 degrees celsius. The crystals melt at 30-35 ℃.

Lyotropic behavior

When the temperature is 30 ℃, after water is added, a large amount of water is absorbed in the surfactant. And an anti-lyotropic phase is formed at the interface with water, where an isotropic micellar cubic phase is formed as the temperature is maintained at 30 degrees celsius. When the temperature is raised from 30 to 55 degrees celsius, the cubic phase boundary moves towards the pure surfactant region. At 55-60 degrees celsius the isotropic cubic phase region gradually narrows and at 65 degrees celsius the hexagonal structure begins to melt. At 70 degrees celsius the isotropic phase disappeared and the hexagonal phase was found to melt further, after which the process continued until a mono-isotropic non-micellar liquid was formed at 80 degrees celsius. The process is reversible, lowering the temperature to 77 degrees celsius will cause the hexagonal structure to reappear, and the isotropic phase to form again at a temperature of 40 degrees celsius.

Example 6-2, 3-Dihydroxypropionic acid 3, 7, 11, 15-tetramethyl-hexadecanoate

Synthesis of

Chemical feature-element analysis

And (3) calculating the result: c71.45, H11.99, O16.55

And (3) analysis results: c70.78, H12.24, O16.98

Chemical characterisation-NMR analysis

¹H NMR m, delta 0.78-0.93, 15H hexadecyl CH₃(ii) a m, delta 0.93-1.80, 24H hexadecyl CH₂+ hexadecyl CH; dd, Δ 2.13, 1H, J8.5 Hz 4.6Hz, glyceryl C3-OH; d, delta 3.16, 1H, J4.6Hz, glyceryl C2-OH; ddd, Δ 3.83, 1H, J-11.4Hz 4.1Hz 8.5Hz, glyceryl C3-H; ddd, 1H, Δ 3.90, J-11.4Hz 3.4Hz 4.8Hz, glyceryl C3-H; ddd, Δ 4.27, 1H, J-4.6Hz 4.1Hz 3.4Hz, glyceryl C2-H; t, delta 4.22, 2H, J6.7Hz, CO₂-CH₂D₂M, delta 0.78-0.93, 15H hexadecyl CH after O treatment₃(ii) a m, delta 0.93-1.80, 24H hexadecyl CH₂+ hexadecyl CH; dd, Δ 3.83, 1H, J-11.4Hz 4.1, glyceryl C3-H; dd, 1H, delta 3.90, J-11.4Hz, 3.4 Hz; glyceryl C3-H; dd, Δ 4.27, 1H, J4.1 Hz 3.4Hz, glyceryl C2-H; t, delta 4.22, 2H, J6.7Hz, CO₂-CH₂The above resonances at 2.13 and 3.16 disappear.

Physical Properties

It was a pale yellow oily substance at room temperature.

Lyotropic behavior

At room temperature, an inverse hexagonal phase is naturally formed on the boundary of the surfactant and the excess water. After heating, the reverse hexagonal phase began to melt slowly around 40 degrees celsius and water was observed to enter the reverse lyotropic phase structure. When the temperature reached 48 degrees celsius, the entire sample appeared isotropic.

Example 7-3, 7, 11, 15-tetramethyl-hexadecanoic acid (1, 1-bis-hydroxymethyl-ethyl) amide

Synthesis of

Chemical characterisation-NMR

¹H NMR sl br d, Δ 0.84, 6H, split 6.3Hz, CH₃(ii) a d, delta 0.86, 6H, split 6.6Hz, CH₃(ii) a d, delta 0.94, 3H, split 6.2Hz, CH₃；m，δ0.97-1.42，21H，chainCH₂+CH；s，1.23，3H，CH₃CH-N；m，δ1.40-1.63，1H，C(3)-H；m，δ1.85-20.7，1.45H，CH₂-N；m，δ2.15-2.34，0.55H，CH₂-N；br s，δ3.47，2H，OH；d，δ3.60，2H，J 11.5Hz，CCH₂OH；d.δ3.74，2H，J11.5Hz，CCH₂OH；br s，δ6.02，1H，NH.

Physical Properties

A pale yellow viscous oil at room temperature with streaks of crystalline material.

Lyotropic behavior

At temperatures of 10-15 degrees celsius, the surfactant rapidly forms an isotropic phase at its interface with water, and a hexagonal phase exists between the phase and the unphased surfactant. When the samples were stored at 23 degrees celsius for 30 minutes, no change occurred at the surfactant to water interface and both regions expanded inward, indicating that they are anti-lyotropic. In some places water enters the oil and dendritic structures are observed along the water phase boundaries. The isotropic band regions were viscous and no flow within the phase was observed. The collected bubbles were non-spherical.

The hexagonal phase begins to melt at 25.5 degrees celsius and is fully isotropic at 26.7 degrees celsius. The hexagonal phase after melting forms a second isotropic phase. The boundaries are determined by refractive index changes. At 32.9 degrees celsius, fines are formed upon contact with water in the isotropic phase. After the sample was held at 32.9 degrees celsius for 20 minutes, the aforementioned hexagonal isotropic region diffused outward toward the water interface, reducing the viscous isotropic region area. At 34.4 degrees celsius the two isotropic phases transform into a single isotropic phase, which is more fluid. When the temperature was increased to 95 degrees celsius, the water in the isotropic phase separated into a similar aqueous phase.

Example 8-1- (2-hydroxyethyl) -3-cis-octadec-9-eneurea

Synthesis of

Chemical characterisation-NMR

¹H NMR sl br t, Δ 0.88, 3H, 6.4Hz cleavage, oleyl CH₃(ii) a m, delta 1.17-1.43, 22H, oleyl CH₂(ii) a m, delta 1.43-1.63, 2H, oleyl CH₂CH₂N；m，δ1.91-2.08，4H，CH₂CH＝CHCH₂(ii) a t, delta 3.19, 2H, J7.6 Hz, oleyl CH₂N; t, delta 3.36, 2H, J4.8 Hz, ethyl CH₂N; t, delta 3.72, 2H, J4.8 Hz, ethyl CH₂OH；m，δ5.25-5.43，1.75H，CH＝CH.

Physical Properties

White crystalline solid with melting point 80-84.7 ℃.

Lyotropic behavior

Upon heating, no interaction between the solid surfactant and water occurred until the temperature reached 59.5 degrees celsius, at which point contact with water began, and an isotropic phase was gradually formed. After the sample was held at 62 degrees celsius for 10 minutes, the isotropic band slowly broadened into the surfactant center. A jelly-like viscosity was observed at the edges of the interface, indicating the production of a high viscosity lyotropic phase. There is a slight difference in refractive index between the inner region (region 2) and the outer region (region 1) of the isotropic band. The outer area is stably enlarged inwards. There is no apparent fluidity in both isotropic regions; the ability to collect non-spherical bubbles means that these regions have a high viscosity. Upon reaching a temperature of 64.4 degrees celsius, a lamellar + isotropic zone (zone 3) and another isotropic phase (zone 4) appear adjacent to the residual surfactant and expand inwardly. The refractive index change illustrates this phenomenon. Flowability was observed in the inner isotropic phase indicating the formation of a non-tacky phase. When the temperature was raised to around 67 degrees celsius, the sample was completely isotropic with the lamellar phase transformed into an isotropic phase and gradually passed over the surfactant center. At 73 degrees celsius, the starting region 2 slowly expands, covering region 3 at 83 degrees celsius. The refractive index difference between regions 1 and 2 is maintained up to a high temperature (> 98 degrees celsius).

Example 9 cis-Octadecyl-9-ene biuret

Synthesis of

Chemical characterisation-NMR

¹H NMR sl br t, Δ 0.88, 3H, split 6.5Hz, oilAlkenyl CH₃(ii) a m, delta 1.17-1.43, 22H, oleyl CH₂；m，δ1.43-1.63，2H，CH₂CH₂N-；m，δ1.89-2.08，4H，CH₂CH＝CHCH₂(ii) a sl br dt, delta 3.22, 2H, J5.6 Hz 6.9Hz, oleyl CH₂N；m，δ5.23-5.44，2，CH＝CH.”

Physical Properties

White waxy solid, melting point 100-.

Lyotropic behavior

The solid crystalline surfactant did not change until the temperature reached 85 degrees celsius when heated, and when the temperature reached 85 degrees celsius, a hexagonal phase began to form at the interface. When the temperature was raised to 87 degrees celsius, a liquid isotropic phase began to form between the hexagonal phase and the crystalline material. The hexagonal phase melted at 107 degrees celsius.

Example 10 cis-Octaden-9-ene Urea

Synthesis of

Chemical characterisation-NMR

¹H NMR sl br t, Δ 0.883H split 6.5Hz, CH₃(ii) a m, delta 1.10-1.70, 24H, oleyl-CH₂；m δ1.89-2.12，4H，CH₂CH＝CHCH₂(ii) a t delta 3.14, 2H, split 7.0Hz, CH₂-NHCONH₂；v br s，δ3.3-4.3，3H，NHCONH₂；m，δ5.23-5.44，2H，CH＝CH.

Physical Properties

White waxy solid with melting point 68-83 ℃.

Lyotropic behavior

No change occurs upon contact with water until the temperature reaches 61 degrees celsius, at which time the reverse hexagonal phase begins to form. At 65 degrees celsius, a liquid isotropic phase began to form between the hexagonal phase and the solid urea. As the temperature is further increased, the solid urea begins to convert to a liquid isotropic phase, which in turn converts to a hexagonal phase. All materials eventually transformed into a hexagonal phase that melted at 110 degrees celsius.

Example 11 cis, cis-octadeca-9, 12-dieneurea

Synthesis of

Chemical characterisation-NMR

¹H NMR sl br t, Δ 0.89, 3H cleavage 6.5Hz, CH₃；m，δ1.15-1.63，20H，CH₂；m，δ1.93-2.17，4HCH₂-CH₂-C ═ C; sl br t, δ 2.78, 2H split 5.5Hz, C ═ C-CH₂-C ═ C; sl br t, delta 3.35, 2H, split 4.7Hz, oleyl-CH₂-NH；v br s，δ3.3-4.4，2.5H，-NHCONH₂；v br s，δ4.5-5.1，0.9H，NHCONH₂；m，δ5.22-5.42，4H，CH＝CH.

Physical Properties

White waxy solid with melting point 70-79 ℃.

Lyotropic behavior

No change occurs upon contact with water until the temperature reaches 53 degrees celsius, at which point the reverse hexagonal phase begins to form. At 59 degrees celsius, a liquid isotropic phase began to form between the hexagonal phase and the solid urea. As the temperature is further increased, the solid urea begins to convert to a liquid isotropic phase, which in turn converts to a hexagonal phase. The addition of moisture to the surfactant can accelerate the process. Solid urea melts at 80 degrees celsius and water is rapidly added to it, which converts all material into a hexagonal phase, which melts at 92-93 degrees celsius.

Example 12 formation of a viscous lyotropic phase by addition of Water to a surfactant

Useful surfactants can preferentially form a viscous lyotropic phase in the presence of excess water. The surfactant-generated lyotropic phase of excess water can be measured by a water immersion experiment in which a small amount of lipid material (typically 5mg) is placed between a glass microscope slide and a coverslip, water is introduced into the sample by capillary action, and the sample is maintained at 40 degrees celsius by incubation. Observation under cross-polarized light at 200 magnification allows the phase generated by the anisotropic structure to be identified or the absence of such a phase to be identified. Table 1 lists the surfactants tested and the lyotropic phase formed in the presence of excess water.

The amount of water entering the lyotropic phase is determined by preparing a 300mg sample of surfactant in excess water, first equilibrated at 40 degrees celsius, followed by determination of the water content in the lyotropic phase by fischer titration. These surfactant water complex test values are also listed in table 1. Values are given as the mean of three samples +/-standard deviation, unless otherwise indicated.

TABLE 1

Finally, other variations and modifications are possible with respect to the articles and methods described herein within the scope of the present invention.

Claims (18)

1. A compound comprising a head group of the following structure (I):

wherein: x is O, S or N, and the formula is,

t and u are each 0 or 1,

R⁵is-C (CH)₂OH)₂Alkyl, -CH (OH) CH₂OH、-CH₂CH(OH)CH₂OH (if the tail group is notIs oleyl), -C (OH)₂CH₂OH、-CH(CH₂OH)₂、-CH₂(CHOH)₂CH₂OH、-CH₂C(O)NHC(O)NH₂；

And the tail group is selected from:

wherein: n is an integer of 2 to 6, a is an integer of 1 to 12, b is an integer of 0 to 10, d is an integer of 0 to 3, e is an integer of 1 to 12, w is an integer of 2 to 10, y is an integer of 1 to 10, and z is an integer of 2 to 10.

2. The compound of claim 1, wherein: the tail group is selected from the group consisting of (3, 7, 11) -trimethyldodecane, (3, 7, 11, 15) -tetramethylhexadecane, or octadec-9-ene and octadec-9, 12-diene.

3. A compound according to claim 2, wherein: the head group is:

4. a compound according to claim 2, wherein: the head group is:

5. a surfactant capable of forming a lyotropic phase and of being stably present in an excess of polar solution, the surfactant comprising a head group of the following structure (I):

and the tail group is selected from the group consisting of a branched alkyl chain, a branched alkoxy chain, or an alkenyl chain, wherein:

x is O, S or N, and the formula is,

t and u are each 0 or 1,

R⁵is-C (CH)₂OH)₂Alkyl, -CH (OH) CH₂OH、-CH₂CH(OH)CH₂OH (if the tail group is not oleyl), -CH₂COOH、-C(OH)₂CH₂OH、-CH(CH₂OH)₂、-CH₂(CHOH)₂CH₂OH、-CH₂C(O)NHC(O)NH₂，

6. The surfactant according to claim 5, wherein: the tail group is selected from the following items:

wherein: n is an integer of 2 to 6, a is an integer of 1 to 12, b is an integer of 0 to 10, d is an integer of 0 to 3, e is an integer of 1 to 12, w is an integer of 2 to 10, y is an integer of 1 to 10, and z is an integer of 2 to 10.

7. The surfactant according to claim 6, wherein: the tail group is selected from the chain consisting of (3, 7, 11) -trimethyldodecane, (3, 7, 11, 15) -tetramethylhexadecane, or octadec-9-ene and octadec-9, 12-diene.

8. The surfactant of claim 7, wherein: the head group is:

9. the surfactant of claim 7, wherein: the head group is:

10. the surfactant of claim 7, wherein: a lyotropic phase is formed in excess water at a temperature of less than 150 degrees celsius.

11. The surfactant of claim 10, wherein: the lyotropic phase formed is a bicontinuous cubic liquid crystal phase.

12. The surfactant of claim 10, wherein: the lyotropic phase formed is an inverse hexagonal liquid crystal phase.

13. The surfactant of claim 10, wherein: the lyotropic phase formed does not convert to a more hydrophilic phase upon addition of excess water.

14. The surfactant of claim 10, wherein: addition of excess water to the lyotropic phase will form a phase separation zone.

15. The surfactant of claim 10, wherein: the lyotropic phase contains a solute contained within the lyotropic phase.

16. The surfactant of claim 15, wherein: one or more substances may be selected as solvents from the list consisting of diagnostic agents, polymeric monomers, polymerization initiators, proteins and other polypeptides, oligonucleotides, denatured and non-denatured DNA, radiotherapeutic agents, sunscreen actives, transdermal agents, dermatological agents, transdermal active compounds, transmucosal active compounds, skin repair agents, wound healing compounds, skin cleansers, degreasers, viscosity altering polymers, hair care actives, labile lipase compounds, agrochemicals, fertilizers and nutrients, vitamins and minerals, explosives or explosives and mixtures thereof, mining materials, or surface coating materials.

17. A mixture comprising a lyotropic phase formed from the surfactant of claim 5.

18. Colloidal particles consisting of a micellar or liquid crystalline lyotropic phase formed from the surfactant of claim 5.