JP6378475B2 - Hydrophilic room temperature ionic liquid and its application - Google Patents

Description

  The present invention relates to ionic liquids, and more particularly to ionic liquids having hydrophilicity, particularly high water solubility, and their uses.

  Conventionally, as an ionic liquid, for example, an ionic liquid composed of an imidazolium-based cation or a quaternary ammonium cation as a cation and various anions is known, and in recent years, application to various applications is also studied. (Patent documents 1 to 3, Non-patent documents 1 and 2).

  For example, solvents for dissolving hydrogen bonding materials such as enzymes, peptides, proteins, nucleic acids, poorly soluble polysaccharides such as cellulose, and other biological materials, reaction solvents, protein refolding agents, visualization agents for electron microscopy, electrolytes In applications such as materials, antistatic agents, lubricating oils, etc., it is desirable that the liquid be fluid (liquid) in the environment of use, and the ionic liquid is required to have a melting point as low as possible. In a broad sense, an organic salt having a melting point of 100 ° C. or less is called an ionic liquid, but in particular, a liquid which is present at room temperature (25 ° C.) is called a room temperature ionic liquid. However, since the mechanism of the liquid expression of the ionic liquid has not been clearly elucidated, there are few cases where various organic salts can be synthesized even if they are liquid, in particular, liquid at room temperature.

  In addition, due to the nonvolatility and nonflammability of ionic liquids, and the recyclability, it is also expected to be used as a low environmental load type heat medium, but it is a liquid at room temperature and has a wide range of heat storage from high temperature to low temperature. It is desirable that they are non-volatile and have excellent heat resistance even at high temperatures, and have a low freezing point when used as a cooling system heat medium and exhibit fluidity even at low temperatures.

  Among such ionic liquids, ionic liquids having hydrophilicity, particularly high water solubility, are expected to enhance the possibilities of application as described above. For example, since the affinity is enhanced by the formation of hydrogen bonds with poorly soluble polysaccharides such as enzymes, peptides, proteins, nucleic acids and celluloses, enzyme dissolution solvents, peptide dissolution solvents, protein dissolution solvents (non-patent document 2), nucleic acids Application to dissolution solvents, dissolution solvents for poorly soluble polysaccharides such as cellulose, protein refolding agents, etc. has been studied. In addition, it is possible to enhance the solubility and dispersibility of inorganic compounds that are difficult to dissolve or disperse in common solvents and ionic liquids such as metals, metal chlorides, metal hydroxides, metal oxides, etc. For example, the reactivity can be enhanced.

  Also in various uses such as a reaction solvent, as the water-soluble protic polar solvent, a novel ionic liquid having a solvent effect and characteristics different from conventional ones is desired. In addition, when observing a biological sample using an ionic liquid as a visualization agent for an electron microscope, in order to obtain an image of the biological sample with high accuracy, a water-soluble ionic liquid is required to enhance affinity with the biological sample. It becomes.

  In addition, chemicals generally maintain their performance during the period of use, but after use they are also released to the environment in small amounts. Therefore, it is desirable to have the aptitude not to give an impact on the environment by being decomposed into carbon dioxide, water, biomass, etc. by enzyme reactions of microorganisms under natural environment such as underground or in water, especially in recent years The importance of environmental protection is increasing. Under these circumstances, ionic liquids are also desired to be readily biodegradable.

  The inventors of the present invention have developed a hydrophilic ionic liquid having a low melting point and enhanced water solubility by introducing a water-soluble functional group into a quaternary ammonium cation as one suitable for the above-mentioned requirements (patent document 4). Specifically, it is a hydrophilic ionic liquid composed of a quaternary ammonium cation having a water-soluble functional group such as an alkyl group and a hydroxyl group, and various anions.

  Also, an ionic liquid composed of an aliphatic quaternary ammonium cation composed of choline or a choline derivative and a carboxylate anion (Patent Document 5), the cation is a primary, secondary or tertiary ammonium containing a charged nitrogen atom Various ionic liquids (Patent Document 6) composed of ions and various anions are disclosed.

Revised 2007-083756 Unexamined-Japanese-Patent No. 2004-509945 JP 2007-126624 A JP 2012-031137 A JP, 2008-162899, A Japanese Patent Application Publication No. 2007-532525

J. Phys. Chem. B 2007, 111, 4807-4811 Chemical Communications, 2005, 4804-4806

  However, although conventional techniques such as the above patent documents disclose ionic liquids using various quaternary ammonium cations, they exhibit a strong correlation with water and exhibit high hydrophilicity, and also include biological substances. There is room for further improvement in the cation structure and the like in relation to the hydrogen bonding material. In addition, there is room for further improvement in the cationic structure which is likely to be liquid to which a wide range of anions can be applied. It is difficult to predict whether even relatively similar molecular structures can be obtained with sufficient properties such as high hydrophilicity, thermal stability and biodegradability, and it is difficult to obtain a low melting point, for example, at room temperature There are few cases where liquid products can be obtained.

  That is, in the structural design of the ionic liquid using the quaternary ammonium cation so far, the influence on the melting point, the high hydrophilicity, the biodegradability, etc. by the selection of the functional group or the characteristic group, especially the hydrogen bond which is difficult to dissolve or disperse Bio-materials such as poorly soluble polysaccharides like enzymes, peptides, proteins, nucleic acids and celluloses with acceptability and electron acceptability, inorganic compounds such as metals, metal chlorides, metal hydroxides and metal oxides, organic compounds etc. The influence on the correlation between the dispersion of the material of (1), the use for the dissolution solvent, etc. and the high hydrophilicity was not sufficiently known.

  The present invention has been made in view of the circumstances as described above, and it is an object of the present invention to provide a novel ionic liquid having a cationic structure which tends to be liquid and having high hydrophilicity, particularly high water solubility. There is.

  Moreover, in addition to the above, this invention makes it a subject to provide the novel ionic liquid which also has biodegradability.

  The present invention also relates to hydrogen bonding properties of enzymes, peptides, biomaterials such as proteins and nucleic acids, inorganic compounds, organic compounds, etc. which are liquid at room temperature, hydrophilic, particularly highly water soluble, and composed of amino acids. An object is to provide a solvent capable of dissolving or dispersing a material.

  The present invention also provides a protein refolding agent which is liquid at room temperature, is hydrophilic, particularly highly water-soluble, and can be used as a refolding solution of solubilized denatured protein by adding it to a buffer or the like. The problem is that.

  Further, the present invention has high heat storage properties in a wide range from high temperature to low temperature, is non-volatile even at high temperature and excellent in heat resistance, is liquid at room temperature, has low solidification point when used as a cooling system heat medium, and fluidity even at low temperature It is an object of the present invention to provide a heat medium which can further reduce the load on the environment.

  In order to solve the above problems, the hydrophilic room temperature ionic liquid of the present invention is a hydrophilic room temperature ionic liquid containing a cation and an anion, and the cation is a quaternary ammonium cation of the following formula (I) It is characterized by

(Wherein, R ¹ independently represents a linear or branched polyhydroxyalkyl group having 2 to 8 carbon atoms having two or more hydroxyl groups, and R ² independently represents a hydrogen atom or a straight chain having 1 to 5 carbon atoms Chain or branched monohydroxyalkyl group, n is an integer of 1 to 4)
The solvent for dissolving or dispersing the hydrogen bonding material of the present invention comprises the above-mentioned hydrophilic room temperature ionic liquid.

  The protein dissolving solvent of the present invention comprises the aforementioned hydrophilic room temperature ionic liquid.

  The nucleic acid dissolving solvent of the present invention comprises the hydrophilic room temperature ionic liquid described above.

  The protein refolding agent of the present invention comprises the hydrophilic room temperature ionic liquid described above.

  The heat medium of the present invention comprises the hydrophilic room temperature ionic liquid described above.

  According to the present invention, it has a cationic structure that tends to be liquid, is highly water soluble, has a specific correlation with hydrogen bonding materials such as biomaterials, and has high solubility and high dispersibility. A novel ionic liquid is provided which exhibits excellent properties as a protein refolding agent and a heat medium. Furthermore, novel ionic liquids having biodegradability are also provided.

  Hereinafter, the present invention will be described in detail.

  The hydrophilic room temperature ionic liquid of the present invention is a hydrophilic room temperature ionic liquid containing a cation and an anion, wherein the cation is a quaternary ammonium cation of the formula (I).

In formula (I), each R ¹ independently represents a linear or branched polyhydroxyalkyl group having 2 to 8 carbon atoms having 2 or more hydroxyl groups, and in particular, 3 to 8 carbon atoms having 2 to 6 hydroxyl groups. A linear polyhydroxyalkyl group or a branched polyhydroxyalkyl group represented by the following formula is preferable.

(Wherein, R ³ represents a hydrogen atom, a linear alkyl group of 1 to 3 carbon atoms, or a linear monohydroxyalkyl group of 1 to 3 carbon atoms)
Specific examples of the polyhydroxyalkyl group as R ¹ include dihydroxyethyl groups such as 1,2-dihydroxyethyl group; 1,2-dihydroxy-n-propyl group, 2,3-dihydroxy-n-propyl group and the like Dihydroxy-n-propyl group; dihydroxy-iso-propyl group such as 1,2-dihydroxy-iso-propyl group and 1,3-dihydroxy-iso-propyl group; trihydroxy-n-propyl group; trihydroxy-iso 1,2-Propyl group; 1,2-Dihydroxy-n-butyl group, 1,3-Dihydroxy-n-butyl group, 1,4-Dihydroxy-n-butyl group, 2,3-Dihydroxy-n-butyl group, 2, Dihydroxy-n-butyl group such as 4-dihydroxy-n-butyl group, 3,4-dihydroxy-n-butyl group; 1,2,3 trihydroxy-n-butyl group, 1,2,4 trihydroxy-n group Trihydroxy-n-butyl group such as -butyl group, 1,3,4 trihydroxy-n-butyl group, 2,3,4 trihydroxy-n-butyl group; Trahydroxy-n-butyl group; dihydroxy-iso-butyl group such as 1,2-dihydroxy-iso-butyl group, 1,3-dihydroxy-iso-butyl group, 2,3-dihydroxy-iso-butyl group; Tri Hydroxy-iso-butyl group; tetrahydroxy-iso-butyl group; 1,2-dihydroxy-sec-butyl group, 1,3-dihydroxy-sec-butyl group, 1,4-dihydroxy-sec-butyl group, 2, Dihydroxy-sec-butyl groups such as 3-dihydroxy-sec-butyl group, 2,4-dihydroxy-sec-butyl group, 3,4-dihydroxy-sec-butyl group; 1,2,3 trihydroxy-sec-butyl group Trihydroxy-sec-butyl group such as 1, 2, 4 trihydroxy-sec-butyl group, 1, 3, 4 trihydroxy-sec-butyl group, 2, 3, 4 trihydroxy-sec-butyl group; Tetrahydroxy-sec-butyl group; 1,3-dihydroxy-2-methyl-iso-propyl group, 1,3-dihydroxy-2-ethyl-iso-propyl group, 1,3-dihydroxy-2-methyl group Droxymethyl-iso-propyl group; di, tri, tetra or pentahydroxy-n-pentyl group; di, tri, tetra or pentahydroxy-n-hexyl group; di, tri, tetra or pentahydroxy-n-heptyl group Di, tri, tetra or pentahydroxy-n-octyl group; di, tri, tetra, penta or hexahydroxy-n-hexyl group; di, tri, tetra, penta, hexa or heptahydroxy-n- group And heptyl groups; di, tri, tetra, penta, hexa, hepta, octahydroxy-n-octyl groups and the like. Among them, 2,3-dihydroxy-n-propyl group, 1,3-dihydroxy-iso-propyl group, 1,3-dihydroxy-2-ethyl-iso-propyl group, 1,3-dihydroxy-2-hydroxymethyl-iso -Propyl group and pentahydroxy-n-hexyl group are more preferable.

  Having this polyhydroxyalkyl group makes it possible to have multiple hydrogen bonding sites and to be more hydrated with water molecules, and because there are two or more hydroxyl groups in one substituent, it is possible to use in the cation. The hydrophobicity by the alkyl group and the alkylene group is reduced, and the water solubility is improved. And by making the cation group have a large number of hydroxyl groups which are anionic and electron donating groups in the cation, the cationic property of the entire quaternary ammonium cation is weak, and the cation is sterically bulky, so the interaction with the anion is small. Become. Furthermore, since it has two or more hydroxyl groups, it does not easily repel or pack with adjacent anions, and the degree of crystallinity is low, and it tends to be liquid.

In formula (I), each R ² independently represents a hydrogen atom or a linear or branched monohydroxyalkyl group having 1 to 5 carbon atoms, and among them, those having 1 to 3 carbon atoms are preferable. Examples of the monohydroxyalkyl group include a hydroxymethyl group, a 2-hydroxyethyl group, a 3-hydroxy-n-propyl group, a 4-hydroxy-n-butyl group, a 5-hydroxy-n-pentyl group, and a 2-hydroxy- group. Examples thereof include iso-propyl group, 2-hydroxy-iso-butyl group, 3-hydroxy-sec-butyl group, 2-hydroxy-iso-pentyl group and the like. Among them, hydroxymethyl group, 2-hydroxyethyl group and 3-hydroxy-n-propyl group are preferable.

  In the hydrophilic room temperature ionic liquid of the present invention, the anion is not particularly limited, but it is, but not limited to, carboxylate anion, halide ion, sulfonic acid anion, alkyl sulfate anion, fluorine anion, inorganic acid anion, cyan anion, Alkyl phosphate anions, alkyl phosphonic acid anions, boron anions and the like can be mentioned.

  As a carboxylate anion, for example, a saturated aliphatic monocarboxylic acid anion, an unsaturated aliphatic monocarboxylic acid anion, a saturated hydroxy monocarboxylic acid anion, a saturated dicarboxylic acid anion, a saturated hydroxydi or tricarboxylic acid anion, an aromatic monocarboxylic acid Anions, saturated carbonyl monocarboxylic acid anions, alkyl ether carboxylic acid anions, halogen carboxylic acid anions and the like can be mentioned.

  The saturated aliphatic monocarboxylic acid anion preferably has 1 to 22 carbon atoms.

Among them, any saturated aliphatic monocarboxylic acid anion selected from HCOO ⁻ and CH ₃ (CH ₂ ) _p COO ⁻ (p represents an integer of 0 to 4), and a saturated aliphatic monocarboxylic acid having a branched chain. Anion is preferred. Specifically, for example, anions in which a proton is dissociated from formic acid, acetic acid, propionic acid, butyric acid, caproic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, isopalmitic acid, isostearic acid and the like can be mentioned.

  The unsaturated aliphatic monocarboxylic acid anion preferably has 3 to 22 carbon atoms.

Among them, R ¹ CH = CH (CH ₂ ) _r COO ⁻ (wherein R ¹ represents a hydrogen atom or CH ₃ (CH ₂ ) _q- (q represents an integer of 0 to 7)), and r represents 0 to 7 Preferred are unsaturated aliphatic monocarboxylic acid anions represented by the integers. Specifically, for example, anions in which a proton is dissociated from acrylic acid, methacrylic acid, crotonic acid, oleic acid, linoleic acid and the like can be mentioned.

  The saturated hydroxy monocarboxylic acid anion preferably has 2 to 22 carbon atoms, and more preferably 2 to 7 carbon atoms. The number of hydroxyl groups is preferably 1 to 4.

Among them, (R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3 and 3 R ² and 2 × s R ³ are each independently a hydrogen atom or The saturated hydroxy monocarboxylic acid anion which shows a hydroxyl group and the total number of a hydroxyl group is 1-2.) Is preferable. Specifically, for example, anions in which a proton is dissociated from glycolic acid, lactic acid (D form, L form) and the like can be mentioned. In addition, a saturated alicyclic hydroxymonocarboxylic acid anion having a cyclohexane ring skeleton is preferred. Specifically, for example, an anion in which a proton is dissociated from quinic acid (1,3,4,5-tetrahydroxycyclohexanecarboxylic acid) can be mentioned.

  The saturated dicarboxylic acid anion preferably has 2 to 22 carbon atoms, and more preferably 3 to 5 carbon atoms.

Among them, a saturated dicarboxylic acid anion represented by HOOC (CH ₂ ) _x COO ⁻ (x represents an integer of 1 to 3) is preferable. Specifically, for example, anions in which a proton is dissociated from malonic acid, succinic acid and the like can be mentioned.

  The saturated hydroxydi or tricarboxylic acid anion preferably has 4 to 22 carbon atoms. The number of hydroxyl groups is preferably 1 to 3.

Among them, HOOCC (R ⁴ R ⁵ ) C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represents a hydrogen atom, a hydroxyl group or a carboxyl group, and the hydroxyl group is a total of 1 The saturated hydroxydi or tricarboxylic acid anion represented by -2 and the carboxyl group is 0-1 in total) is preferable. Specifically, for example, anions in which a proton is dissociated from malic acid (D form, L form), tartaric acid (D form, L form), citric acid and the like can be mentioned.

  The aromatic monocarboxylic acid anion preferably has 6 to 20 carbon atoms.

  Among them, hydroxyaromatic monocarboxylic acid anions are preferable, and the number of hydroxyl groups is preferably 1 to 2. The hydroxy aromatic monocarboxylic acid anion has a phenyl ring skeleton, in particular, a structure in which a carboxylic acid anion and a hydroxyl group are directly bonded to a phenyl group, or a structure in which a carboxylic acid anion is bonded to a phenyl group via a hydroxymethylene group. Is preferred. Specifically, for example, anions in which a proton is dissociated from salicylic acid, p-hydroxybenzoic acid, mandelic acid and the like can be mentioned.

  The saturated carbonyl monocarboxylic acid anion preferably has 3 to 22 carbon atoms, and more preferably 3 to 5 carbon atoms. The number of carbonyl groups is preferably 1 to 2.

Among _{them, CH 3 ((CH 2)} t CO (CH 2) u) COO - (t and u is an integer of 0 to 2.) Preferably saturated carbonyl monocarboxylic acid anion represented by. Specifically, for example, an anion in which a proton is dissociated from pyruvic acid and the like can be mentioned.

  The alkyl ether carboxylic acid anion preferably has 2 to 22 carbon atoms, and more preferably 3 to 10 carbon atoms. The number of ether bonds is preferably 1 to 10.

Among them, alkyl ether carboxylate anions represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent an integer of 0 to 4) are preferable. Specifically, for example, anions in which a proton is dissociated from methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid and the like can be mentioned.

  The halogen carboxylate anion preferably has 2 to 22 carbon atoms. Specifically, for example, anions in which a proton is dissociated from fluorine-substituted halogen carboxylic acid such as trifluoroacetic acid, pentafluoropropionic acid and the like can be mentioned.

The halide ion, e.g., bromide ion (Br ^-), chloride ion (Cl ^{-) -} and the like is, iodide ion (I).

As a fluorine type anion, for example, trifluoroacetate ion (CF ₃ COO ⁻ ), trifluoromethanesulfonate ion (CF ₃ SO ₃ ⁻ ), bis (trifluoromethanesulfonyl) imide ion ((CF ₃ SO ₂ ) ₂ N ⁻ ) Hexafluorophosphate ion (PF ₆ ⁻ ), tetrafluoroborate ion (BF ₄ ⁻ ) fluorine anion (F ⁻ ), and the like.

Examples of the sulfonic acid-based anion, for example, methanesulfonate ion (CH ₃ SO ₃ ^-), ethanesulfonic acid ion ^{_{(CH 3 CH 2 SO 3 -}} ), p- toluenesulfonate ion (CH ₃ -C ₆ H ₄ - SO ₃ ⁻ ) and the like.

The inorganic acid anions such as sulfate ion (SO ₄ ^2-), nitrate ion (NO ₃ ^-), carbonate ions (CO ₃ ^2-), phosphate ion (H ₂ PO ₄ ^-) and the like.

Examples of the cyanide anion include dicyanamide ion (N (CN) ₂ ⁻ ), tricyanomethanide ion (C (CN) ₃ ⁻ ), thiocyanate ion (SCN ⁻ ) and the like.

  The hydrophilic room temperature ionic liquid of the present invention can be synthesized, for example, as follows.

  The hydrophilic room temperature ionic liquid of the present invention comprises mono-, di- or trialkanolamines corresponding to the quaternary ammonium cation of the formula (I) and organic or inorganic acids corresponding to the anion, and polar solvents such as water and acetonitrile. Let react in. Although the reaction temperature and the reaction time depend on the type of the raw material and the like, they can be carried out, for example, at room temperature for about 1 hour to 1 day. Thereafter, the solvent is distilled off under reduced pressure, and if necessary, purification is carried out to obtain the target hydrophilic room temperature ionic liquid as a liquid. In addition, when the reaction is carried out equimolarly and the reaction is completed, there is no need for a purification step, and the production process can be further simplified.

  Moreover, it can also synthesize | combine as follows. A mono-, di-, or trialkanolamine is reacted with an organic halogen compound such as polyhydroxyalkyl halide in a polar solvent such as water or acetonitrile to correspond to the structure of the quaternary ammonium cation of the formula (I) . The reaction temperature and the reaction time may be, for example, about 1 day at room temperature, although it depends on the kind of the raw material. Thereafter, the reaction product can be washed to obtain a compound consisting of a quaternary ammonium cation of formula (I) and a halide ion. Furthermore, anion exchange is carried out in the case of making the target anion from the halide ion. When anion exchange is performed, for example, the obtained reaction product is reacted in water with an organic acid or inorganic acid corresponding to the anion of the target compound. The reaction temperature and the reaction time may be, for example, about 1 day at room temperature, although it depends on the kind of the raw material. Alternatively, after using the strongly basic ion exchange resin or the like, after performing anion exchange to a hydroxide anion, the target hydrophilic room temperature ionic liquid is obtained by further anion exchange with an organic acid or inorganic acid corresponding to the anion of the target compound. You can get

  In the hydrophilic room temperature ionic liquid of the present invention, the cationic property of the entire quaternary ammonium cation is weak due to the presence of more hydroxyl groups which are anionic and electron donating groups in the cation, and the cation is sterically bulky. Because it is high, the interaction with the anion is reduced. Furthermore, since it has two or more hydroxyl groups, it repels with adjacent anions, is difficult to pack, has a low crystallinity, and tends to be liquid. Therefore, a wide range of anions can be applied.

  The hydrophilic room temperature ionic liquid of the present invention is liquid at room temperature (25 ° C.) and has a melting point of 0 ° C. or less, and even less than −5 ° C. In a broad sense, an organic salt having a melting point of 100 ° C. or less is called an ionic liquid, but in particular, a liquid which is present at room temperature (25 ° C.) is called a room temperature ionic liquid. Since room temperature ionic liquids have the flowability originally required for ionic liquids even near room temperature, they are expected to be developed for various applications.

  In addition, that an ionic liquid is a liquid here means the state which has fluidity | liquidity (For example, the thing without fluidity | liquidity like a gel is not included).

  The hydrophilic room temperature ionic liquid of the present invention has no substituent consisting of only a hydrophobic alkyl group as a cation, and is a cation of only a hydrogen atom capable of hydrogen bonding with a water molecule, a (poly) hydroxyalkyl group, It has multiple hydrogen bonding sites in one ionic liquid molecule and can be hydrated with more water molecules. In addition, since two or more hydroxyl groups exist in one substituent, the hydrophobicity due to the alkyl group and the alkylene group in the cation is reduced, so that the affinity with water is high and high water solubility can be exhibited. The hydrophilic room temperature ionic liquid of the present invention has a solubility in water at room temperature (25 ° C.) of 1200 g / 100 g water or more.

  The hydrophilic room temperature ionic liquid of the present invention has a high biodegradation rate, can reduce environmental load, and is excellent in environmental suitability. For example, the 28-day BOD degradation degree by the biodegradability test based on the OECD (economic cooperation development mechanism) test guideline 301 C method can be made 60% or more. Among the OECD Test Guideline 301, the OECD Test Guideline 301C method is a substance that is more than 60% degradable calculated from 28 days of biochemical oxygen demand (BOD) is an easily biodegradable substance, The aerobic water environment is rapidly decomposed, so it does not remain in the environment, and the environmental impact can be reduced.

  That is, a chemical substance is stable during use, but is often discharged into the environment after use, so it is desirable that the environmental load be small. For example, in the case of use under open conditions to the environment, it is desirable that the biodegradability be high and the environmental load be small. In recent years, environmental problems typified by industrial waste have become serious, and reducing waste is an important responsibility of companies. In this respect, highly biodegradable chemical substances are degraded by microorganisms without being incinerated after disposal, which leads to waste reduction. At present, biodegradability is focused on in the fields of plastics and lubricating oils, and new material development is being conducted. In the background as described above, the hydrophilic room temperature ionic liquid of the present invention is a raw material of quaternary ammonium cation, amine raw material used to correspond to anion, grasping the biodegradability of organic acid or inorganic acid, Degradability can be predicted for structural design, and as a result, a highly biodegradable ionic liquid can be obtained, as well as contributing to environmental load reduction.

  Furthermore, the hydrophilic room temperature ionic liquid of the present invention also has the properties possessed by ordinary ionic liquids such as non-volatility, thermal conductivity, non-combustibility, conductivity, etc. It also contributes to the reduction of environmental impact from its superiority.

  Since the hydrophilic room temperature ionic liquid of the present invention is liquid at room temperature and the like, and is hydrophilic, particularly highly water-soluble, and low in environmental impact type excellent also in biodegradability, these characteristics and structural features are obtained. Bio-materials such as enzymes, peptides, proteins, poorly soluble polysaccharides such as nucleic acids and cellulose, hydrogen bonding inorganic compounds including metal oxides, dispersion or dissolution solvents for materials such as organic compounds, protein It can be used in applications such as folding agents, reaction solvents, electron microscope visualizing agents, electrolyte materials, antistatic agents, lubricating oils, heat transfer media, solvents, pharmaceuticals and cosmetics, and is hydrophilic because it is water or polar It can also be used in combination with a solvent.

  The hydrophilic room temperature ionic liquid of the present invention takes advantage of the structural features of the cation, and has solubility and dispersibility of materials such as biomaterials, inorganic compounds, organic compounds and the like by hydrogen bond donating property, electron donating property and coordination property. Can increase the reactivity or increase the reactivity. In addition, the solubility and dispersibility in hydrogen bonding materials including hydrogen bond accepting materials are not only cations, but hydrogen and high electronegativity with high oxygen anion anions functional groups such as hydroxyl groups and carboxyl groups covalently bonded In addition, its effect is enhanced. That is, when there is no functional group such as a hydroxyl group or a carboxyl group in which only one of the anion or cation has hydrogen and oxygen having a high electronegativity covalently bonded, an enzyme or peptide composed of one amino acid molecule consisting of two amino acids Among the biopolymers such as protein and cellulose, hydrogen bonding with one molecule of biopolymer is possible, but hydrogen bonding with the other molecule is difficult. However, having both functional groups in both the cation and the anion enables hydrogen bonding with a stable structure in both of the biopolymer of the two molecules and the anion and the cation, and easily enters the matrix of the biopolymer.

  The solubility and dispersibility of the ionic liquid in the hydrogen bonding material is important for the hydrogen bonding between the ionic liquid and the hydrogen bonding material, and as one index to determine the degree of interaction by the hydrogen bonding, the ion It can be judged indirectly by the solubility of the ionic liquid in water due to the hydrogen bond between the liquid and the water molecule. That is, the very high solubility and dispersibility of the hydrophilic room temperature ionic liquid of the present invention in the hydrogen bonding material is also suggested from their high water solubility.

  The hydrophilic room temperature ionic liquid of the present invention has no substituent consisting of only a hydrophobic alkyl group as a cation, and is a cation of only a hydrogen atom capable of hydrogen bonding with a water molecule, a (poly) hydroxyalkyl group, Since it has multiple hydrogen bonding sites in one ionic liquid molecule, hydrogen bonding materials, in particular, hydrogen bond accepting functional groups containing elements 15, 16 and 17 such as nitrogen, oxygen and halogen having high electronegativity A material having a group (for example, a carbonyl group or an ether group) has high affinity, and thus it is useful, for example, for use as a storage solvent for a hydrogen-bonding biomaterial, a dissolution solvent, and the like.

  The hydrophilic room temperature ionic liquid of the present invention is, for example, an enzyme having a carbonyl group or an ether group, a peptide, a protein, a hydrogen, a hydrogen bond accepting functional group of a biological material such as poorly soluble polysaccharide such as nucleic acid or cellulose, etc. Together with the formation of bonds, the ionic liquid penetrates into the intricately intertwined structure of the biomaterial to break up the biomolecular structure, and the steric bulk of the polyhydroxyl group of the cation keeps the distance between the biopolymers constant. Since the interaction between biopolymers can be reduced, they are useful as highly soluble solvents, storage solvents, and protein refolding agents.

  The hydrophilic room temperature ionic liquid of the present invention can be stored for a long time without denaturing the protein even at room temperature, but generally, the storage solution in which the protein is dissolved is desirably stored at low temperature, 0 ° C. or less However, it is desirable to maintain the stability stably, and the hydrophilic room temperature ionic liquid of the present invention is useful because it has a melting point of less than -5 ° C.

  The hydrophilic room temperature ionic liquid of the present invention is an inorganic compound such as metal, metal chloride, metal hydroxide, metal oxide, etc. having hydrogen bond accepting ability and electron accepting ability which are difficult to dissolve and disperse in ordinary solvents and ionic liquids. Also for organic compounds, optical materials have an effect on dissolution, dispersion, and high reactivity by the hydroxyl group of the hydrogen bond donating property, electron donating property, and coordinating property of ionic liquid, and the high reactivity. , Electronic materials, dissolution of catalysts, dispersion solvents, reaction solvents and the like.

  The hydrophilic room temperature ionic liquid of the present invention may be used as an enzyme reaction solvent which has good affinity to the enzyme due to its hydrogen bond donating property, for example, and which can be reused as well as general organic reaction solvents. it can. In addition, it can be used as an organic reaction solvent having a hydrogen bond donor type catalyst function by the hydroxyl group in the polyhydroxyalkyl group of the quaternary ammonium cation.

  The solvent for dissolving or dispersing the hydrogen bonding material of the present invention includes the hydrophilic room temperature ionic liquid of the present invention, and when used as a solvent, the hydrophilic room temperature ionic liquid of the present invention may be used alone. It is also possible to use this in combination with other solvent components such as water and polar solvents, or to add additives.

  As a hydrogen bonding material to be a target of the solvent for dissolving or dispersing the hydrogen bonding material of the present invention, a material containing a hydrogen bond accepting element or functional group, particularly, a biomaterial, a material of an organic or inorganic compound, etc. Can be mentioned.

  Examples of biomaterials include enzymes, peptides, proteins, nucleic acids, poorly soluble polysaccharides such as cellulose, and the like.

  Among the solvents for dissolving or dispersing the hydrogen bonding material of the present invention, a protein dissolving solvent using a protein as a biomaterial is not particularly limited as a protein to be dissolved, but from the viewpoint of solution properties, for example, a carboxyl group And acidic proteins containing a large amount of amino acids (aspartate, glutamic acid, etc.), alkaline proteins containing a large number of amino acids (lysine, algin, histidine, etc.), and neutral proteins with well-balanced amino acids.

  The component includes simple proteins consisting only of amino acids, and complex proteins consisting of components other than amino acids. Simple proteins include albumin, casein, collagen, keratin, protamine, histone, etc. Complex proteins include glycoproteins (luteinizing hormone, follicle stimulating hormone, thyroid stimulating hormone, human chorionic gonadotropin, avidin, cadherin, proteoglycan, Mucins etc., Lipoproteins (Chylomicrons, LDL, HDL etc.), Nuclear Proteins (proteins of histones, telomerase, protamine etc.), chromoproteins (chlorophyll etc.), Metalloproteins (hemoglobin, Cytochrome C etc.), Phosphoproteins Casein in milk, vitellin in egg yolk etc. All enzymes are either of these proteins.

  Moreover, from the shape of the molecule, fibrous proteins (keratin, collagen etc.) and globular proteins (hemoglobin etc.), from the function, enzyme protein (enzyme), structural protein (collagen, keratin etc.), transport protein ( Hemoglobin, albumin, apolipoprotein, etc., storage proteins (ovalbumin in egg white, ferritin, hemosiderin, etc.), contractile proteins (actin, myosin, etc.), protective proteins (globulin, etc.), regulatory proteins (calmodulin, etc.).

  From molecular and intermolecular structure to primary structure (sequence of amino acids), secondary structure (α-helix, β-structure, random coil), tertiary structure (specific spatial arrangement), quaternary structure (hemoglobin, DNA polymerase, ionic Channel etc.).

  The molecular weight of the protein is not particularly limited, but 4,000 to 300,000 are considered.

  Among the solvents for dissolving or dispersing the hydrogen bonding material of the present invention, in the nucleic acid dissolving solvent using a nucleic acid as a biomaterial, examples of the nucleic acid to be dissolved include DNA, RNA and the like. These nucleic acids are known to be easily hydrolyzed in water by their degradative enzymes, and when using water as a solvent, it is necessary to dissolve them in water from which they have been removed. By using the nucleic acid lysing solvent of the present invention for storage of nucleic acids and storing it as a nucleic acid-containing solution, the nucleic acids can be stored under the environment where the nucleolytic enzyme is inactivated, and also nonvolatile and heat Since the stability is also high, the long-term stable storage of the nucleic acid can be easily achieved. Then, by using a nucleic acid lysing solvent for the reaction of nucleic acid, for example, by performing a chemical modification reaction of the nucleic acid in this solvent, a reaction using a reagent which could not be handled in water which is a conventional solvent, or in water It is possible to carry out a reaction that is difficult to progress in a wide temperature range.

  In the solvent for dissolving or dispersing the hydrogen bonding material of the present invention, as the material of the organic or inorganic compound to be dissolved or dispersed, those dissolved in the hydrophilic room temperature ionic liquid of the present invention as molecules, ions, etc. Examples of the fine particles include those dispersed in the hydrophilic room temperature ionic liquid of the present invention. For example, a compound or fine particle having a hydrogen bond accepting Group 15, 16 or 17 element as a constituent element of a molecule or functional group, a fine particle surface-modified with a functional group containing these elements, etc. may be mentioned. The particle size of the fine particles is not particularly limited, and examples thereof include particles with a particle size of 1 nm to 100 μm.

  The protein refolding agent of the present invention comprises the hydrophilic room temperature ionic liquid of the present invention alone or the hydrophilic room temperature ionic liquid of the present invention, for example, water, a buffer, and these and a polar solvent, if necessary, a denaturant or a reduction It is added to a mixture with additives such as agents and used as a refolding solution.

  Protein refolding is to restore from a protein which has been insolubilized or lost the conformation to a protein in the native state (activated state) of the conformation. For example, a protein which has been insolubilized or lost of higher-order structure is directly solubilized and refolded, as required, by adding a denaturing agent to the refolding solution containing the hydrophilic room temperature ionic liquid of the present invention described above. Alternatively, a protein which has been insolubilized or lost in higher-order structure may be solubilized by a general protein solubilizing agent by adding a denaturing agent as necessary, and the solubilization solution is made hydrophilic according to the above-mentioned present invention An active protein is obtained by dissolving in a refolding solution containing a room temperature ionic liquid to restore the conformation to the protein.

  In refolding, for example, in the method using a surfactant, if the action of the surfactant is too strong, the steric structure of the protein is broken, and if it is too weak, the protein can not be sufficiently solubilized and the compatibility between the surfactant and the protein is also a problem. Therefore, it is necessary to screen using a plurality of surfactants. In addition, it is not easy to release the surfactant from the protein. On the other hand, the hydrophilic room temperature ionic liquid of the present invention is highly soluble in various proteins, has no influence on the structure of the protein, has a long-term stability and is also simple as a protein solubilization and storage solvent It is useful.

  For various conditions in the solubilization step of the inclusion body and misfolded protein which are not dissolved unless a denaturing agent is used, and the refolding step, for example, JP-A-2011-500517 is referred to.

  That is, in the solubilization step, solubilization is carried out by using a buffer solution containing a denaturing agent such as guanidine hydrochloride and optionally a reducing agent. In the subsequent refolding step, the denatured protein solubilization solution is brought into contact with the refolding solution containing the protein refolding agent of the present invention by dilution, dialysis or the like to reduce the effect of the denaturing agent and refold. And regenerate their natural state to show their biological activity.

  When the hydrophilic room temperature ionic liquid of the present invention is used as a visualizing agent for an electron microscope used under heating conditions by electron beam irradiation, its high conductivity can prevent electrification of the sample observation surface by a simple means. . Furthermore, since it is highly water-soluble, has a relatively small molecular size, and has a flexible molecular structure, it has high permeability when applied to a biological sample by being well replaced with water in the biological sample, and the biological sample is Deformation such as shrinkage of the bulk shape and microstructure of the above is suppressed, and observation with high accuracy becomes possible.

  The hydrophilic room temperature ionic liquid of the present invention is used as a low environmental load type reaction solvent, electrolyte material, antistatic agent, lubricating oil, heat medium, etc. in view of its nonvolatility and safety derived from nonflammability and recyclability. However, target systems such as antifreeze, lubricating oil, and electrolyte materials, which are heating media in particular, are used in a wide temperature range from low temperature below freezing below 0 ° C to high temperature above 150 ° C, It is useful because low temperature liquid property and heat stability are required.

  The heat medium of the present invention contains the hydrophilic room temperature ionic liquid of the present invention, and depending on the conditions of use, water, alcohol solvents such as methanol and isopropyl alcohol, ketone solvents such as acetone and methyl ethyl ketone, ethyl acetate and the like. It can be used by mixing with ester solvents, ethylene glycol, polyethylene glycol, toluene, vegetable oil, animal oil, mineral oil and the like.

  Conventionally, in cooling systems such as internal combustion engines and fuel cells, glycols and the like are used as a base of heat medium such as coolant and antifreeze liquid, and heat medium and snow and ice particles are used to prevent freezing on the road surface or melt snow. Although water, ethylene glycol, chloride, acetate and the like are used as the base of the heat medium in the direct water melting and snow melting technology in which heat is exchanged in direct contact, according to the heat medium of the present invention, even under high temperature It is non-volatile and excellent in heat resistance, is liquid at room temperature, has a low freezing point when used as a cooling system heat medium, exhibits fluidity even at low temperatures, and can reduce environmental load. In particular, the heat medium of the present invention exhibits a high specific heat capacity as compared with the base used for the conventional heat medium as described above in a wide temperature range from a low temperature of -50 ° C to a high temperature near 100 ° C. , Show high heat storage. That is, since the hydrophilic room temperature ionic liquid of the present invention has a hydrogen atom or a hydroxyalkyl group as a cation, and a hydrogen bonding functional group such as a hydroxyl group or an ether group as an anion, hydrogen can be generated in the molecule and between molecules The specific heat capacity is increased due to the strong intermolecular and intramolecular interaction by forming a bond, and the heat storage property is high compared to the conventional compounds, which is suitable as a heat medium.

  The heat medium of the present invention can be used for a wide range of purposes as a fluid to transfer heat between an external heat source and the device in order to heat or cool the device to control it to the desired temperature. The heat medium of the present invention is used, for example, as a base for coolants and antifreezes of devices used at high temperatures such as internal combustion engines, fuel cells, heat pipes, motors, etc., and also to roads, runways, glass etc. It can be suitably used as an antifreezing agent or a snow melting agent by containing or spreading or spreading to water in the spraying or coating of water, or in a temporary circulation type toilet, household equipment (door, door, toilet, drainage trap, etc.). For example, in recent years, the temperature at the time of operation tends to be increased during operation due to the improvement of fuel efficiency and the reduction of harmful substances discharged. However, the temperature of coolant etc. also becomes high accordingly. In the background, the hydrophilic room temperature ionic liquid of the present invention is suitable as a base of heat transfer medium.

  The hydrophilic room temperature ionic liquid of the present invention, for example, when used as an electrolyte material, an antistatic agent, a lubricating oil, and a heat medium, in particular, a hydrogen bond donating property consisting only of (poly) hydroxyalkyl group, electron donating property and coordination An ionic liquid composed of a hydrophilic and hydrophilic quaternary ammonium cation, a hydrophobic long-chain monosaturated fatty acid anion, a long-chain unsaturated fatty acid anion, an aromatic carboxylic acid anion and the like can be used as a target medium (metal, Arrays or functions on the surface or interface of fibers, resins, water etc.) to improve affinity, compatibility, permeability, etc. or to activate or modify the medium to exert functions, which is useful. It is.

  It is widely known that an ionic liquid composed of a cation and an anion has conductivity, and is useful, for example, for modifying the surface of a medium such as antistatic.

  As described above, by using the hydrophilic room temperature ionic liquid of the present invention, it becomes possible to design a reaction having characteristics and functions of the ionic liquid and to create a material having a new function.

EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.
Example 1
The compound represented by the following formula was synthesized.

After reacting 2-amino-1,3-propanediol (2.50 g, 27.44 mmol) and formic acid (1.26 g, 27.44 mmol) in 50 ml of water at room temperature for 3 hours, the water is distilled off under reduced pressure and yellow I got a liquid. The obtained liquid was washed to obtain ammonium formate (3.76 g, 27.44 mmol) as a colorless and transparent liquid.
FT-IR (KBr): 3362cm -1: O-H stretching vibration 2954cm ^-1: C-H stretching vibration 1588cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.15-3.19 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.49-3.65 (m, 4H, HOC H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 8.30 (s, 1H, H COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 53.8 (HOCH 2 C H (N + H 3) CH 2 OH), δ 59.5 (HO C H 2 CH (N + H 3) C H 2 OH), δ 171.0 (H C OO ^-).
Examples 2 to 72
The compounds of Examples 2 to 72 shown in Tables 1 and 2 and Tables 4 to 11 were synthesized by the same synthesis method as in Example 1 and the compounding molar ratio described in Tables 4 to 11. Physical property values are shown below.
Example 2

FT-IR (KBr): 3370cm -1: O-H stretching vibration 2960cm ^-1: C-H stretching vibration 1561cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 1.84 (s, 3H, C H 3 COO -), δ 3.27-3.38 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.62-3.78 (m, 4H, HOC H 2 CH (N + H 3) C H 2 OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 23.3 (C H 3 COO -), δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + _{H 3) C H 2 OH)} , δ 181.4 (CH 3 C OO -).
Example 3

FT-IR (KBr): 3152cm -1: O-H stretching vibration 2921cm ^-1: C-H stretching vibration 1549cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 1.76 (s, 3 H, C ₃ H ₃ COO ⁻ ), δ 2.89-3.09 (m, 2 H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.47-3.68 (m, 5H, HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 3.86-3.90 (m, 1 H, HOCH ₂ (CH (CH OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 23.2 (C H 3 COO -), δ 41.6 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 62.6 (HO C _{H 2 (CH (OH))} 3 CH (OH) CH 2 NH 3 +), δ 68.9-70.8 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 181.4 ( CH ₃ C OO ^-).
Example 4

FT-IR (KBr): 3152cm -1: O-H stretching vibration 2921cm ^-1: C-H stretching vibration 1549cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.60-0.68 (m, 6H, NH 3 + C (CH 2 OH) 2 CH 2 C H 3, C H 3 CH 2 CH 2), δ 1.25-1.47 ( ^{_{m, 4H, NH 3 + C}} (CH 2 OH) 2 C H 2 CH 3, CH 3 C H 2 CH 2), δ 3.40 (t, 2H CH 3 CH 2 C H 2) δ 3.40 (s, 4H, _{^{NH 3 + C (C H 2}} OH) 2 CH 2 CH 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 6.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 13.2 (C H 3 CH 2 CH 2), δ 19.2 (CH 3 C H _{2 CH 2), δ 23.2 (} NH 3 + C (CH 2 OH) 2 C H 2 CH 3), δ 39.5 (CH 3 CH 2 C H 2), δ 60.7 (NH 3 + C (CH 2 OH) 2 _{CH 2 CH 3), δ 60.9} (NH 3 + C (C H 2 OH) 2 CH 2 CH 3), δ 183.7 (CH 3 CH 2 CH 2 C OO -).
Example 5

FT-IR (KBr): 3370cm -1: O-H stretching vibration 2960cm ^-1: C-H stretching vibration 1561cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.64-0.73 (m, 6H, NH 3 + C (CH 2 OH) 2 CH 2 C H 3, C H 3 CH 2 CH 2 CH 2), δ 1.04- _{1.10 (m, 4H, CH 3} CH 2 C H 2 C H 2), δ 1.31-1.51 (m, 4H, NH 3 + C (CH 2 OH) 2 C H 2 CH 3, CH 3 C H 2 CH 2 _{CH 2), δ 1.92-1.96 (t} , 2H C H 2 COO -), δ 3.44 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 6.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 13.3 (C H 3 CH 2 CH 2), δ 21.7 (CH 3 C H _{2 CH 2), δ 23.3 (} NH 3 + C (CH 2 OH) 2 C H 2 CH 3), δ 25.5 (CH 3 CH 2 CH 2 C H 2), δ 31.0 (CH 3 CH 2 C H 2 CH _{2), δ 37.5 (C H} 2 COO -), δ 60.6 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 60.7 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3 _{), δ 184.0 (CH 2 C} OO -).
Example 6

FT-IR (KBr): 3392cm -1: O-H stretching vibration 2929cm ^-1: C-H stretching vibration 1558cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.83-0.90 (m, 6H, C H 3 (CH 2) 8 CH ((CH 2) 6 C H 3) COO -), δ1.06-1.51 (m _{, 28H, CH 3 (C H} 2) 8 CH ((C H 2) 6 CH 3) COO -), δ 2.13-2.16 (m, 1H, CH 3 (CH 2) 8 C H ((CH 2) 6 ^{_{CH 3) COO -), δ}} 3.30-3.39 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.64-3.77 (m, 4H, HOC H 2 CH (N + H 3) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2), δ 22.7 (CH 3 C H-- 2 CH 2), δ 26.4 (C H 2 CH 2 CHCOO -), δ 30.0 ( _{CH 3 CH 2 CH 2 (C} H 2) 4 CH 2 CH 2 CH (CH 2 CH 2 (C H 2) 2 CH 2 CH 2 CH 3) COO -, CH 2 C H 2 CHCOO -), δ 31.9 ( _{CH 3 CH 2 C H 2)} , δ 37.7 (C HCOO -), δ 54.6 (HOCH 2 C H (N + H 3) CH 2 OH), δ 60.2 (HO C H 2 CH (N + H 3) C _{H 2 OH), δ 182.1 (} CH C OO -).
Example 7

FT-IR (KBr): 3120cm -1: O-H stretching vibration 2922cm ^-1: C-H stretching vibration 1543cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.84-0.94 (m, 9H, NH 3 + C (CH 2 OH) 2 CH 2 C H 3, C H 3 (CH 2) 8 CH ((CH 2) ₆ C H ₃ ) COO ⁻ ), δ 1.08−1.68 (m, 30 H, NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ , CH ₃ (C H ₂ ) ₈ CH ((C H ₂ ) ₆ ) ^{_{CH 3) COO -), δ}} 2.14-2.18 (m, 1H, CH 3 (CH 2) 8 C H ((CH 2) 6 CH 3) COO -), δ 3.58-3.67 (m, 4H, NH 3 + _{C (C H 2 OH) 2} CH 2 CH 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 7.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 14.1 (C H 3 CH 2), δ 22.7 (CH 3 C H-- ₂ CH ₂ ), δ 25.1 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ), δ 26.4 ( C H ₂ CH ₂ CHCOO ⁻ ), δ 30.0 (CH ₃ CH ₂ CH ₂ ( C H _{2) ) 4 CH 2 CH 2 CH (} CH 2 CH 2 (C H 2) 2 CH 2 CH 2 CH 3) COO -, CH 2 C H 2 CHCOO -), δ 31.9 (CH 3 CH 2 C H 2), δ ^{38.0 (C HCOO -), δ} 60.2 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 62.9 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3), δ 182.1 (CH C OO ^-).
Example 8

FT-IR (KBr): 3153cm -1: O-H stretching vibration 2922cm ^-1: C-H stretching vibration 1551cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.83-0.90 (m, 6H, C H 3 (CH 2) 8 CH ((CH 2) 6 C H 3) COO -), δ1.08-1.58 (m _{, 28H, CH 3 (C H} 2) 8 CH ((C H 2) 6 CH 3) COO -), δ 2.24-2.28 (m, 1H, CH 3 (CH 2) 8 C H ((CH 2) 6 CH ₃ ) COO ⁻ ), δ 3.67 (s, 6 H, NH ₃ ⁺ C (C H ₂ OH) ₃ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2), δ 22.7 (CH 3 C H-- 2 CH 2), δ 27.1 (C H 2 CH 2 CHCOO -), δ 30.0 ( _{CH 3 CH 2 CH 2 (C} H 2) 4 CH 2 CH 2 CH (CH 2 CH 2 (C H 2) 2 CH 2 CH 2 CH 3) COO -, CH 2 C H 2 CHCOO -), δ 31.9 ( _{CH 3 CH 2 C H 2)} , δ 37.2 (C HCOO -), δ 61.0 (NH 3 + C (CH 2 OH) 3), δ 61.5 (NH 3 + C (C H 2 OH) 3), δ 182.1 (CH C OO ^-).
Example 9

FT-IR (KBr): 3392cm -1: O-H stretching vibration 2929cm ^-1: C-H stretching vibration 1588cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.85 to 0.91 (m, 6 H , C H ₃ (CH ₂ ) ₈ CH ((CH ₂ ) ₆ C H ₃ ) COO ⁻ ), δ 1.12-1.59 (m, _{28H, CH 3 (C H 2} ) 8 CH ((C H 2) 6 CH 3) COO -), δ 2.14-2.18 (m, 1H, CH 3 (CH 2) 8 C H ((CH 2) 6 CH ^{_{3) COO -), δ 3.04-3.11}} (m, 2H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 3.63-3.84 (m, 5H, HOC H 2 (C H (OH) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 3.97-3.98 (m, 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.6 (C H 3 CH 2), δ 23.8 (CH 3 C H-- 2 CH 2), δ 27.8 (C H 2 CH 2 CHCOO -), δ 30.8 ( _{CH 3 CH 2 CH 2 (C} H 2) 4 CH 2 CH 2 CH (CH 2 CH 2 (C H 2) 2 CH 2 CH 2 CH 3) COO -, CH 2 C H 2 CHCOO -), δ 31.2 ( _{CH 3 CH 2 C H 2)} , δ 38.3 (C HCOO -), δ 43.3 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 64.7 (HO C H 2 (CH _{(OH)) 3 CH (OH} ) CH 2 NH 3 +), δ 71.0-72.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 183.2 (CH C OO - ).
Example 10

FT-IR (KBr): 3394 cm ^-1 : OH stretching vibration 2957 cm ^-1 : CH stretching vibration 1558 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.29-3.40 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.67-3.77 (m, 4H, HOC H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 5.96 (m, 1H, C H 2 CHCOO -), δ 6.22 (m, 1H, CH 2 C H COO -), δ 6.66 (m, 1H, C H 2 CHCOO ^- ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH), δ ^{_{127.7-132.7 (C H 2 C HCOO -}} ), δ 175.4 (CH 2 CH C OO -).
Example 11

FT-IR (KBr): 3362cm -1: O-H stretching vibration 2956cm ^-1: C-H stretching vibration 1559cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 1.68-1.70 (m, 3H, C H 3 CHCHCOO -), δ 3.29-3.34 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH) , δ 3.58-3.74 (m, 4H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH), δ 5.69-5. 75 (m, 1 H, CH ₃ CHC H COO ⁻ ), δ 6.49-6.53 (m, ^{_{1H, CH 3 C H CHCOO -}} ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 16.9 (C H 3 CHCHCOO -), δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + _{H 3) C H 2 OH)} , δ 127.2 (CH 3 CH C HCOO -), δ 141.2 (CH 3 C HCHCOO -), δ 175.9 (CH 3 CHCH C OO -).
Example 12

FT-IR (KBr): 3398 cm ^-1 : OH stretching vibration 2922 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.88 (t, 3H, C H 3 CH 2 CH 2), δ 1.27 (s, 20H, CH 3 (C H 2) 6 CH 2, (C H 2) ₄ CH ₂ CH ₂ COO ⁻ ), δ 1.53 (s, 2 H, C H ₂ CH ₂ COO ⁻ ), δ 1.96-2.01 (m, 4 H, C H ₂ CHCHC H ₂ ), δ _2. 16 (t, 2 H, CH ^{_{2 C H 2 COO -),}} δ 3.27-3.28 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.64-3.77 (m, 4H, HOC H 2 CH (N + H 3 ) C H ₂ OH), δ 5.32-5. 38 (m, 2 H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 CH 2), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 ( _{C H 2 CHCH C H 2)} , δ 29.3-29.9 (CH 3 CH 2 CH 2 (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H _{2), δ 37.5 (CH 2} C H 2 COO -), δ 54.6 (HOCH 2 C H (N + H 3) CH 2 OH), δ 60.2 (HO C H 2 CH (N + H 3) C H 2 OH), δ 129.7-130.0 (C H C H), δ 181.8 (C OO -).
Example 13

FT-IR (KBr): 3144cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1554cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.88 (t, 3H, C H 3 CH 2 CH 2), δ 1.27 (s, 20H, CH 3 (C H 2) 6 CH 2, (C H 2) ₄ CH ₂ CH ₂ COO ⁻ ), δ 1.57 (s, 2 H, C H ₂ CH ₂ COO ⁻ ), δ 1. 98-2.01 (m, 4 H, C H ₂ CHCHC H ₂ ), δ _2. 24 (s, 2 H, CH ₂ C H ₂ COO ⁻ ), δ 3.67 (s, 6 H, NH ₃ ⁺ C (C H ₂ OH) ₃ ), δ 5.32-5. 38 (m, 2 H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 CH 2), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 ( C H ₂ CHCH C H ₂ ), δ 29.3-29.8 (CH ₃ CH ₂ CH ₂ ( C H ₂ ) ₄ , ( C H ₂ ) ₄ CH ₂ CH ₂ COO ⁻ ), δ 31.9 (CH ₃ CH ₂ C H ₂ ), δ 32.6 (CH ₂ C H ₂ COO ⁻ ), δ 60.9 (NH ₃ ⁺ C (CH ₂ OH) ₃ ), δ 61.5 (NH ₃ ⁺ C ( C H ₂ OH) ₃ ), δ 129.7-130.0 (C H C H), δ 181.8 (C OO -).
Example 14

FT-IR (KBr): 3144cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1554cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.90 (t, 3H, C H 3 CH 2 CH 2), δ 1.30 (s, 20H, CH 3 (C H 2) 6 CH 2, (C H 2) ₄ CH ₂ CH ₂ COO ⁻ ), δ 1.57 (s, 2 H, C H ₂ CH ₂ COO ⁻ ), δ 2.00-2.04 (m, 4 H, C H ₂ CHCHC H ₂ ), δ _2. 17 (t, 2 H, CH ₂ C H ₂ COO ⁻ ), δ 3.06-3..14 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.65-3.84 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.98-4.01 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.6 (C H 3 CH 2 CH 2), δ 23.8 (CH 3 C H 2 CH 2), δ 27.6 (C H 2 CH 2 COO -), δ 28.3 ( _{C H 2 CHCH C H 2)} , δ 30.4-31.0 (CH 3 CH 2 CH 2 (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 33.1 (CH 3 CH 2 C H ₂ ), δ 38.8 (CH ₂ C H ₂ COO ⁻ ), δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 64.7 (HO C H ₂ (CH (OH (OH) ₂ ) )) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 70.7-72.9 (HOCH ₂ ( C H (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ), δ 130.9-130.9 ( C H C H H) ^{), δ 182.7 (C OO -} ).
Example 15

FT-IR (KBr): 3398 cm ^-1 : OH stretching vibration 2922 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.88 (t, 3H, C H 3 CH 2 CH 2), δ 1.24-1.30 (m, 14H, CH 3 (C H 2) 3 CH 2, (C H _{2) 4 CH 2 CH 2 COO} -), δ 1.51 (s, 2H, C H 2 CH 2 COO -), δ 1.96-2.01 (m, 4H, CH 2 C H 2 CH), δ 2.14 (t, 2H ^{_{, CH 2 C H 2 COO -}} ), δ 2.76 (t, 2H, CHC H 2 CH), δ 3.29 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.63-3.77 ( _{m, 4H, HOC H 2 CH} (N + H 3) C H 2 OH), δ 5.29-5.49 (m, 4H, C H C H).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 CH 2), δ 25.6 (CH C H 2 CH), δ 26.3 (C H ^{_{2 CH 2 COO -), δ}} 27.2 (CH 2 C H 2 CH), δ 29.4-31.5 (CH 3 CH 2 (C H 2) 2, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 _{(CH 3 CH 2 C H 2} ), δ 37.5 (CH 2 C H 2 COO -), δ 54.5 (HOCH 2 C H (N + H 3) CH 2 OH), δ 59.6 (HO C H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 127.9-130.2 (C H C H), δ 182.4 (C OO -).
Example 16

FT-IR (KBr): 3398 cm ^-1 : OH stretching vibration 2922 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.86-0.92 (m, 6H, NH 3 + C (CH 2 OH) 2 CH 2 C H 3, C H 3 CH 2 CH 2), δ 1.25-1.37 ( _{m, 14H, CH 3 (C} H 2) 3 CH 2, (C H 2) 4 CH 2 CH 2 COO -), δ 1.52 (s, 2H, C H 2 CH 2 COO -), δ 1.65 (m, ^{_{2H, NH 3 + C (CH}} 2 OH) 2 C H 2 CH 3), δ 2.02-2.15 (m, 4H, CH 2 C H 2 CH), δ 2.15 (t, 2H, CH 2 C H 2 COO - ), δ 2.76 (t, 2 H, CHC H ₂ CH), δ 3.57-3.64 (m, 4 H, NH ₃ ⁺ C (C H ₂ OH) ₂ CH ₂ CH ₃ ), δ 5.29-5.49 (m, 4 H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 7.2 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H _{2 CH 2), δ 24.4 (} NH 3 + C (CH 2 OH) 2 C H 2 CH 3), δ 25.6 (CH C H 2 CH), δ 26.5 (C H 2 CH 2 COO -), δ 27.2 ( _{CH 2 C H 2 CH),} δ 29.4-31.5 (CH 3 CH 2 (C H 2) 2, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H 2), δ 38.0 (CH ₂ C H ₂ COO ⁻ ), δ 60.6 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 61.8 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ) , δ 129.9-130.2 (C H C H ), δ 182.3 (C OO -).
Example 17

FT-IR (KBr): 3144cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1554cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.88 (t, 3 H, C H ₃ CH ₂ CH ₂ ), δ 1.25-1.37 (m, 14 H , CH ₃ (C H ₂ ) ₃ CH ₂ , (C H _{2) 4 CH 2 CH 2 COO} -), δ 1.53 (s, 2H, C H 2 CH 2 COO -), δ 2.02-2.07 (m, 4H, CH 2 C H 2 CH), δ 2.16 (t, 2H ^{_{, CH 2 C H 2 COO -}} ), δ 2.76 (t, 2H, CHC H 2 CH), δ 3.64 (s, 6H, NH 3 + C (C H 2 OH) 3), δ 5.28-5.39 (m, 4H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 CH 2), δ 25.6 (CH C H 2 CH), δ 26.5 (C H ^{_{2 CH 2 COO -), δ}} 27.2 (CH 2 C H 2 CH), δ 29.4-31.5 (CH 3 CH 2 (C H 2) 2, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 _{(CH 3 CH 2 C H 2} ), δ 37.5 (CH 2 C H 2 COO -), δ 60.6 (NH 3 + C (CH 2 OH) 3), δ 61.0 (NH 3 + C (C H 2 OH) _{3), δ 127.9-130.2 (C H} C H), δ 182.3 (C OO -).
Example 18

FT-IR (KBr): 3174 cm ^-1 : OH stretching vibration 2924 cm ^-1 : CH stretching vibration 1577 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.90 (t, 3H, C H 3 CH 2 CH 2), δ 1.30-1.40 (m, 14H, CH 3 (C H 2) 3 CH 2, (C H _{2) 4 CH 2 CH 2 COO} -), δ 1.61 (s, 2H, C H 2 CH 2 COO -), δ 2.05-2.08 (m, 4H, CH 2 C H 2 CH), δ 2.19 (t, 2H ^{_{, CH 2 C H 2 COO -}} ), δ 2.77 (t, 2H, CHC H 2 CH), δ 3.10-3.15 (m, 2H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 ^{+), δ 3.67-3.73 (m,} 5H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 NH 3 +), δ 3.79-4.00 (m, 1H, HOCH 2 (CH (OH) ) ₃ C H (OH) CH ₂ NH ₃ ⁺ ), δ 5.38-5.40 (m, 4H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 23.7 (CH 3 C H 2 CH 2), δ 26.6 (CH C H 2 CH), δ 27.7 (C H ^{_{2 CH 2 COO -), δ}} 28.3 (CH 2 C H 2 CH), δ 30.5-30.8 (CH 3 CH 2 (C H 2) 2, (C H 2) 4 CH 2 CH 2 COO -), δ 32.7 _{(CH 3 CH 2 C H 2} ), δ 39.0 (CH 2 C H 2 COO -), δ 43.3 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 64.7 (HO _{C H 2 (CH (OH)} ) 3 CH (OH) CH 2 NH 3 +), δ 70.8-72.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 129.1 −131.0 ( C H C H), δ 183.0 ( C OO ⁻ ).
Example 19

FT-IR (KBr): 3373cm -1: O-H stretching vibration 2954cm ^-1: C-H stretching vibration 1588cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.35-3.41 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.65-3.80 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH), δ 3.89 (s, 2H, HOC H ₂ COO ⁻ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.2 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH), δ ^{_{61.2 (HO C H 2 COO -}} ), δ 179.8 (HOCH 2 C OO -).
Example 20

FT-IR (KBr): 3167cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1573cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.94-3.13 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.51-3.72 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.82 (s, 2H, HOC H 2 COO -), δ 3.89-3.96 (m, 1H, HOCH 2 (CH ( OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.7 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 61.2 (HO C H ₂ COO ⁻ ), δ 62.6 (HO _{C H 2 (CH (OH)} ) 3 CH (OH) CH 2 NH 3 +), δ 68.9-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 179.9 (HOCH ₂ C OO ^-).
Example 21

FT-IR (KBr): 3231cm -1: O-H stretching vibration 2972cm ^-1: C-H stretching vibration 1571cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 1.17-1.24 (m, 3H, C H 3 CH (OH) COO -), δ 3.22-3.27 (m, 1H, CH 3 C H (OH) COO -) , δ 3.55-3.71 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 3.97-4.02 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 20.0 (C H 3 CH (OH) COO -), δ 53.9 (HOCH 2 C H (N + H 3) CH 2 OH), δ 59.3 (HO C H 2 _{^{CH (N + H 3) C}} H 2 OH), δ 68.4 (CH 3 C H (OH) COO -), δ 182.4 (CH 3 CH (OH) C OO -).
Example 22

FT-IR (KBr): 3231cm -1: O-H stretching vibration 2937cm ^-1: C-H stretching vibration 1571cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.77 to 0.81 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.17 to 1.24 (m, 3 H, C H ₃ CH ^{(OH) COO -), δ} 1.51-1.57 (m, 2H, NH 3 + C (CH 2 OH) 2 C H 2 CH 3), δ 3.52 (s, 4H, NH 3 + C (C H 2 OH) ₂ CH ₂ CH ₃ ), δ 3.94-3.99 (m, 1 H, CH ₃ C H (OH) COO ⁻ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 6.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 20.0 (C H 3 CH (OH) COO -), δ 23.5 (NH 3 _{^{+ C (CH 2 OH) 2}} C H 2 CH 3), δ 60.3 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 61.0 (NH 3 + C (C H 2 OH) 2 CH 2 CH ₃ ), δ 68.5 (CH ₃ C H (OH) COO ⁻ ), δ 182.4 (CH ₃ CH (OH) C OO ⁻ ).
Example 23

FT-IR (KBr): 3228cm -1: O-H stretching vibration 2935cm ^-1: C-H stretching vibration 1571cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 1.15-1.17 (m, 3H, C H 3 CH (OH) COO -), δ 3.53 (s, 6H, NH 3 + C (C H 2 OH) 3) , δ 3.91-4.11 (m, 1H, CH 3 C H (OH) COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 20.0 (C H 3 CH (OH) COO -), δ 59.8 (NH 3 + C (CH 2 OH) 3), δ 60.7 (NH 3 + C (C H _{2 OH) 3), δ 68.4} (CH 3 C H (OH) COO -), δ 182.4 (CH 3 CH (OH) C OO -).
Example 24

FT-IR (KBr): 3234cm -1: O-H stretching vibration 2926cm ^-1: C-H stretching vibration 1572cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 1.14 (m, 3H, C H 3 CH (OH) COO -), δ 2.83-3.02 (m, 2H, HOCH 2 (CH (OH)) 3 CH (OH ) C H ₂ NH ₃ ⁺ ), δ 3.45-3.66 (m, 5 H, HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 3.81-3.85 (m, 1 H, HOCH _{2 (CH (OH)) 3} C H (OH) CH 2 NH 3 +), δ 3.90-3.95 (m, 1H, CH 3 C H (OH) COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 20.1 (C H 3 CH (OH) COO -), δ 41.7 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ _{62.6 (HO C H 2 (CH} (OH)) 3 CH (OH) CH 2 NH 3 +), δ 68.4 (CH 3 C H (OH) COO -), δ 68.9-70.9 (HOCH 2 (C H (OH )) ₃ C H (OH) CH ₂ NH ₃ ⁺ ), δ 182.5 (CH ₃ CH (OH) C OO ⁻ ).
Example 25

FT-IR (KBr): 3394cm -1: O-H stretching vibration 2957cm ^-1: C-H stretching vibration 1716 cm ^-1: COOH stretching vibration 1584cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.29-3.40 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.67-3.77 (m, 6H, HOC H 2 CH (N _{^{+ H 3) C H 2 OH}} , HOOCC H 2 COO -).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.3 (HOOC C H ₂ COO ⁻ ), δ 54.1 (HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 58.6 (HO C H ₂ CH (N _{^{+ H 3) C H 2 OH}} ), δ 174.6 (HOO C CH 2 C OO -).
Example 26

FT-IR (KBr): 3388cm -1: O-H stretching vibration 2958cm ^-1: C-H stretching vibration 1714 cm ^-1: COOH stretching vibration 1558cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.42 (s, 4 H, HOOC H ₂ C H ₂ COO ⁻ ), δ 3.29-3.35 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH ), δ 3.58-3.74 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
¹³ C-NMR (D ₂ O 100 MHz): δ 31.3 (HOOC C H ₂ C H ₂ COO ⁻ ), δ 54.1 (HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 58.6 (HO C H _{2) ^{CH (N + H 3) C}} H 2 OH), δ 179.7 (HOO C CH 2 CH 2 C OO -).
Example 27

FT-IR (KBr): 3388cm -1: O-H stretching vibration 2922cm ^-1: C-H stretching vibration 1714 cm ^-1: COOH stretching vibration 1543 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.73-0.77 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.50-1.56 (m, 2 H, NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ), δ 2.33 (s, 4 H, HOOC H ₂ C H ₂ COO ⁻ ), δ 3.49-3.50 (m, 4 H, NH ₃ ⁺ C (C H ₂ OH) ₂ CH ₂ CH ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.2 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) _{, δ 31.4 (HOOC C H 2} C H 2 COO -), δ 60.5 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 63.3 (NH 3 + C (C H 2 OH) 2 CH 2 _{CH 3), δ 179.7 (HOO} C CH 2 CH 2 C OO -).
Example 28

FT-IR (KBr): 3177cm -1: O-H stretching vibration 2925cm ^-1: C-H stretching vibration 1709 cm ^-1: COOH stretching vibration 1551 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.42 (s, 4 H, HOOC H ₂ C H ₂ COO ⁻ ), δ 2.89-3.08 (m, 2 H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.46-3.67 (m, 5 H, HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 3.85-3.89 (m, 1 H, HOCH _{2 (CH (OH)) 3 C} H (OH) CH 2 NH 3 +).
¹³ C-NMR (D ₂ O 100 MHz): δ 31.2 (HOOC C H ₂ C H ₂ COO ⁻ ), δ 41.6 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.6 (HO 3 C ₂ H ₂ (CH (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 68.9-70.8 (HOCH ₂ ( C ₂ H (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ) _{, δ 179.6 (HOO C CH 2} CH 2 C OO -).
Example 29

FT-IR (KBr): 3375cm -1: O-H stretching vibration 2955cm ^-1: C-H stretching vibration 1717 cm ^-1: COOH stretching vibration 1576 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.52-2.76 (m, 2 H, HOOC H ₂ CH (OH) COO ⁻ ), δ 3.32-3. 38 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) _{CH 2 OH), δ 3.61-3.77 (} m, 4H, HOC H 2 CH (N + H 3) C H 2 OH), δ 4.29-4.32 (m, 1H, HOOCCH 2 C H (OH) COO -).
¹³ C-NMR (D ₂ O 100 MHz): δ 40.1 (HOOC C H ₂ CH (OH) COO ⁻ ), δ 54.1 (HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 58.6 (HO C H ₂ CH (N ⁺ H ₃ ) C H ₂ OH), δ 68.7 (HOOCCH ₂ C H (OH) COO ⁻ ), δ 176.4 (CH ₂ C OOH), δ 179.1 (C (OH) C OO ⁻ ).
Example 30

FT-IR (KBr): 3447cm -1: O-H stretching vibration 2956cm ^-1: C-H stretching vibration 1743cm ^-1: COOH stretching vibration 1515 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.37-3.43 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.66-3.81 (m, 4H, HOC H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 4.49 (s, 2H, HOOCC H (OH) C H (OH) COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.2 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH), δ 72.8 (HOOC C H (OH) C H (OH) COO -), δ 176.3 (HOO C CH (OH) CH (OH) C OO -).
Example 31

FT-IR (KBr): 3388cm -1: O-H stretching vibration 2955cm ^-1: C-H stretching vibration 1721 cm ^-1: COOH stretching vibration 1556cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.66-2.83 (m, 4 H, HOOC H ₂ C (OH) (COOH) C H ₂ COO ⁻ ), δ 3.32-3. 38 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 3.60-3.77 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
¹³ C-NMR (D ₂ O 100 MHz): δ 43.7 (HOOC C H ₂ C (OH) (COOH) C H ₂ COO ⁻ ), δ 54.1 (HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 58.6 (HO C H ₂ CH (N ⁺ H ₃ ) C H ₂ OH), δ 73.8 (HOOCCH ₂ C (OH) (COOH) CH ₂ COO ⁻ ), δ 174.7 (HOO C CH ₂ C (OH) ( ^{_{COOH) CH 2 C OO -)}} , δ 178.6 (HOOCCH 2 C (OH) (C OOH) CH 2 COO -).
Example 32

FT-IR (KBr): 3156cm -1: O-H stretching vibration 2940cm ^-1: C-H stretching vibration 1713 cm ^-1: COOH stretching vibration 1570cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.75-0.79 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.52-1.58 (m, 2 H, NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ), δ 2.57-2.75 (m, 4 H, HOOCC H ₂ C (OH) (COOH) C H ₂ COO ⁻ ), δ 3.52 (s, 4 H, NH ₃ ⁺ C (C H ₂ OH) ₂ CH ₂ CH ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.2 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) _{, δ 43.7 (HOOC C H 2} C (OH) (COOH) C H 2 COO -), δ 60.5 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 61.0 (NH 3 + C (C H ₂ OH) ₂ CH ₂ CH ₃ ), δ 73.8 (HOOCCH ₂ C (OH) (COOH) CH ₂ COO ⁻ ), δ 174.8 (HOO C CH ₂ C (OH) (COOH) CH ₂ C OO ⁻ ), _{δ 178.5 (HOOCCH 2 C (OH} ) (C OOH) CH 2 COO -).
Example 33

FT-IR (KBr): 3145cm -1: O-H stretching vibration 2946cm ^-1: C-H stretching vibration 1711cm ^-1: COOH stretching vibration 1572cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.58-2.75 (m, 4H, HOOCC H 2 C (OH) (COOH) C H 2 COO -), δ 3.57 (s, 6H, NH 3 + C (C H ₂ OH) ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 43.7 (HOOC C H ₂ C (OH) (COOH) C H ₂ COO ⁻ ), δ 59.2 (NH ₃ ⁺ C (CH ₂ OH) ₃ ), δ 61.4 (δ _{^{NH 3 + C (C H 2}} OH) 3), δ 73.8 (HOOCCH 2 C (OH) (COOH) CH 2 COO -), δ 174.8 (HOO C CH 2 C (OH) (COOH) CH 2 C OO - _{), δ 178.6 (HOOCCH 2 C} (OH) (C OOH) CH 2 COO -).
Example 34

FT-IR (KBr): 3226cm -1: O-H stretching vibration 2931cm ^-1: C-H stretching vibration 1711cm ^-1: COOH stretching vibration 1575cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.66-2.83 (m, 4H, HOOCC H 2 C (OH) (COOH) C H 2 COO -), δ 2.90-3.10 (m, 2H, HOCH 2 (CH _{(OH)) 3 CH (OH} ) C H 2 NH 3 +), δ 3.48-3.68 (m, 5H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 NH 3 +), δ 3.86 −3.90 (m, 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.7 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 43.6 (HOOC C H ₂ C (OH) (COOH) C ^{_{H 2 COO -), δ 62.6}} (HO C H 2 (CH (OH)) 3 CH (OH) CH 2 NH 3 +), δ 68.9-70.8 (HOCH 2 (C H (OH)) 3 C H (OH ) CH ₂ NH ₃ ⁺ ), δ 73.8 (HOOCCH ₂ C (OH) (COOH) CH ₂ COO ⁻ ), δ 174.6 (HOO C CH ₂ C (OH) (COOH) CH ₂ C OO ⁻ ), δ 178.6 ( _{HOOCCH 2 C (OH) (C} OOH) CH 2 COO -).
Example 35

FT-IR (KBr): 3370cm -1: O-H stretching vibration 2950cm ^-1: C-H stretching vibration 1592cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.28-3.33 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.57-3.72 (m, 4H, HOC H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 6.80-6.86 (m, 2H, C (OH) C H CH, C (COO -) CHC H CH), δ 7.35-7.39 (m, 1H, C H CHC ( OH)), δ 7.68-7.73 (m , 1H, C (COOH) C H CH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + H 3) C H 2 OH), δ 116.2 (C (OH) C HCH ), δ 118.0 (CH C (COO -) C (OH)), δ 119.3 (C (COO -) CH C HCH), δ 130.5 (C (COO -) C HCH), δ 133.9 (C HCHC (OH) ), δ 159.6 (C C (OH) C), δ 175.5 (C C OO -).
Example 36

FT-IR (KBr): 3248cm -1: O-H stretching vibration 2921cm ^-1: C-H stretching vibration 1570cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.87-3.05 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.46-3.66 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.87-3.90 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ), δ 6.72-6.78 (m, 2H , C (OH) C H CH, C (COO -) CHC H CH), δ 7.22-7.24 (m, 1H, C H CHC (OH)), δ 7.61-7.63 (m, 1 H, C (COOH) C H CH).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.7 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.6 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 69.0-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 116.2 (C (OH) C HCH), δ 117.9 ^{(CH C (COO -) C} (OH)), δ 119.3 (C (COO -) CH C HCH), δ 130.4 (C (COO -) C HCH), δ 133.9 (C HCHC (OH)), δ 159.5 (C C (OH) C) , δ 175.5 (C C OO -).
Example 37

FT-IR (KBr): 3341cm -1: O-H stretching vibration 2947cm ^-1: C-H stretching vibration 1577cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.29-3.35 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.59-3.75 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH), δ 7.31-7.35 (m, 5 H, (C H ) ₅ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + H 3) C H 2 OH), δ 75.0 (C H (OH) ( COO -), δ 127.1 ((CH) 2 C H (CH) 2), δ 128.2 (C HCHC C H (OH) (COO -)), δ 128.8 (C HCCH (OH ^{) (COO -)), δ} 140.6 (C CH (OH) (COO -)), δ 179.4 (C OO -).
Example 38

FT-IR (KBr): 3388cm -1: O-H stretching vibration 2955cm ^-1: C-H stretching vibration 1556cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.20 (m, 3 H, C ₃ H ₃ CO), δ 3.32-3. 38 (m, 1 H, HOCH ₂ C ₂ H (N ⁺ H ₃ ) CH ₂ OH), δ 3.60 -3.77 (m, 4H, HOC H 2 CH (N + H 3) C H 2 OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.6 (C H 3 CO), δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + H _{3) C H 2 OH),} δ 165.3 (CH 3 CO C OO -), δ 191.8 (CH 3 C OCOO -).
Example 39

FT-IR (KBr): 3156 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1570 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.75-0.79 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.52-1.58 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 2.20 (m, 3H, C H 3 CO), δ 3.52 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 6.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 14.6 (C H 3 CO), δ 23.2 (NH 3 + C (CH 2 _{OH) 2 C H 2 CH 3} ), δ 60.5 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 61.0 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3), δ ^{_{165.3 (CH 3 CO C OO -}} ), δ 191.8 (CH 3 C OCOO -).
Example 40

FT-IR (KBr): 3145cm -1: O-H stretching vibration 2946cm ^-1: C-H stretching vibration 1572cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.20 (m, 3H, C H 3 CO), δ 3.57 (s, 6H, NH 3 + C (C H 2 OH) 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.6 (C H 3 CO), δ 59.2 (NH 3 + C (CH 2 OH) 3), δ 61.4 (NH 3 + C (C H 2 OH) 3) _{, δ 165.3 (CH 3 CO C} OO -), δ 191.8 (CH 3 C OCOO -).
Example 41

FT-IR (KBr): 3371 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1582 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.23 (s, 3H, C H 3 OCH 2 COO -), δ 3.30-3.36 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH) , δ 3.60-3.76 (m, 6H, HOC H 2 CH (N + H 3) C H 2 OH, CH 3 OC H 2 COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 48.9 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.1 (C H 3 OCH 2 COO -), δ 58.6 (HO C H 2 CH ( _{^{N + H 3) C H 2}} OH), δ 71.1 (CH 3 O C H 2 COO -), δ 178.1 (CH 3 OCH 2 C OO -).
Example 42

FT-IR (KBr): 3148 cm ^-1 : OH stretching vibration 2928 cm ^-1 : CH stretching vibration 1574cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.16 (s, 3 H, C H ₃ OCH ₂ COO ⁻ ), δ 3.53 (s, 6 H, NH ₃ ⁺ C (C H ₂ OH) ₃ ), δ 3.67 ( _{s, 2H, HOCCH 3 OC H} 2 COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 48.8 (NH 3 + C (CH 2 OH) 3), δ 59.3 (C H 3 OCH 2 COO -), δ 61.3 (NH 3 + C (C H 2 OH ₃ ), δ 71.0 (CH ₃ O C H ₂ COO ⁻ ), δ 177.9 (CH ₃ OCH ₂ C OO ⁻ ).
Example 43

FT-IR (KBr): 3174 cm ^-1 : OH stretching vibration 2924 cm ^-1 : CH stretching vibration 1577 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.89-3.09 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.20 (s, 3H, C H ₃ OCH ₂ COO ⁻ ), δ 3.48-3.69 (m, 5 H, HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 3.72 (s, 2 H, CH ₃ OC H ₂ COO ⁻ ), δ 3.85-3.90 (m, 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 41.6 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 58.0 (C H 3 OCH 2 COO -), δ 62.6 ( HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ NH ₃ ⁺ ), δ 69.0-70.8 (HOCH ₂ ( C H (OH)) ₃ C H (OH) CH ₂ NH ₃ ⁺ ), δ 71.1 (CH ₃ O C H ₂ COO ⁻ ), δ 178.0 (CH ₃ OCH ₂ C OO ⁻ ).
Example 44

FT-IR (KBr): 3371 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1582 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.99 (s, 3H, C H 3 CH 2 OCH 2 COO -), δ 3.20-3.25 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.34-3.39 (q, 2H, CH 3 C H 2 OCH 2 COO -), δ 3.49-3.64 (m, 6H, HOC H 2 CH (N + H 3) C H 2 OH, CH 3 CH ₂ OC H ₂ COO ^{-).
_{13 C-NMR (D 2 O}} 100MHz): δ 14.0 (C H 3 CH 2 O), δ 54.0 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N _{^{+ H 3) C H 2 OH}} ), δ 66.4 (CH 3 C H 2 O), δ 69.1 (CH 3 CH 2 O C H 2 COO -), δ 178.1 (CH 3 CH 2 OCH 2 C OO -).
Example 45

FT-IR (KBr): 3156 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1570 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.75-0.79 (t, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 0.99 (t, 3 H, C H ₃ CH ₂ OCH ₂ COO ⁻ ), δ 1.45 to 1.47 (q, 2 H, NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ), δ 3.28 to 3.33 (q, 2 H, CH ₃ C H ₂ OCH ₂ COO ⁻ ) , δ 3.42 (s, 4 H, NH ₃ ⁺ C (C ₂ H ₂ OH) ₂ CH ₂ CH ₃ ), δ 3.63 (m, 2 H, CH ₃ CH ₂ OC H ₂ COO ⁻ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 6.3 (NH 3 + C (CH 2 OH) 2 CH 2 C H 3), δ 14.0 (C H 3 CH 2 O), δ 23.2 (NH 3 + C ( _{CH 2 OH) 2 C H 2} CH 3), δ 60.4 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 60.9 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3) _{, δ 66.4 (CH 3 C H} 2 O), δ 69.1 (CH 3 CH 2 O C H 2 COO -), δ 177.9 (CH 3 CH 2 OCH 2 C OO -).
Example 46

FT-IR (KBr): 3148 cm ^-1 : OH stretching vibration 2928 cm ^-1 : CH stretching vibration 1574cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.95 (t, 3H, C H 3 CH 2 OCH 2 COO -), δ 3.31-3.33 (q, 2H, CH 3 C H 2 OCH 2 COO -), δ _{3.48 (s, 6H, NH 3} + C (C H 2 OH) 3), δ 3.66 (s, 2H, CH 3 CH 2 OC H 2 COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.0 (C H 3 CH 2 O), δ 59.2 (NH 3 + C (CH 2 OH) 3), δ 61.3 (NH 3 + C (C H 2 OH) _{3), δ 66.4 (CH 3} C H 2 O), δ 69.1 (CH 3 CH 2 O C H 2 COO -), δ 178.1 (CH 3 CH 2 OCH 2 C OO -).
Example 47

FT-IR (KBr): 3174 cm ^-1 : OH stretching vibration 2924 cm ^-1 : CH stretching vibration 1577 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 1.06 (t, 3 H, C H ₃ CH ₂ OCH ₂ COO ⁻ ), δ 2.92-3. 11 (m, 2 H, HOCH ₂ (CH (OH)) ₃ CH (OH) ^{_{) C H 2 NH 3 +)}} , δ 3.41-3.46 (q, 2H, CH 3 C H 2 OCH 2 COO -), δ 3.49-3.69 (m, 5H, HOC H 2 (C H (OH)) 3 CH ^{_{(OH) CH 2 NH 3 +}} ), δ 3.78 (s, 2H, CH 3 CH 2 OC H 2 COO -), δ 3.88-3.95 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH ) CH ₂ NH ₃ ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.0 (C H 3 CH 2 O), δ 41.6 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 62.6 (HO _{C H 2 (CH (OH)} ) 3 CH (OH) CH 2 NH 3 +), δ 66.6 (CH 3 C H 2 O), δ 69.0-70.9 (HOCH 2 (C H (OH)) 3 C H ( ^{_{OH) CH 2 NH 3 +,}} CH 3 CH 2 O C H 2 COO -), δ 178.0 (CH 3 CH 2 OCH 2 C OO -).
Example 48

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration 1576 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.28-3.33 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.58-3.73 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH), δ ^{_{114.9-117.8 (C F 3 COO -)}} , δ 162.8-163.1 (CF 3 C OO -).
Example 49

FT-IR (KBr): 3267 cm ^-1 : OH stretching vibration 2926 cm ^-1 : CH stretching vibration 1671 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.86-3.05 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.48-3.69 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.84-3.89 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.8 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.6 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 69.4-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ 114.8-117.7 (C F 3 COO -), δ ^{_{162.7-163.4 (CF 3 C OO -)}} .
Example 50

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.33-3.46 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 3.69-3.84 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.2 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 51

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.75-0.79 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.39-1.44 (m, 2 H, NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ), δ 3.39-3.46 (m, 4 H, NH ₃ ⁺ C (C H ₂ OH) ₂ CH ₂ CH ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.6 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 24.6 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 57.8 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 62.8 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
Example 52

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.78-2.98 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.52-3.72 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.79-3.84 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
¹³ C-NMR (D ₂ O 100 MHz): δ 42.1 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.7 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 70.6-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +).
Example 53

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.30-3.36 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.60-3.76 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 54

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.72-0.76 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.48-1.54 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 3.48 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.4 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 48.9 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 60.8 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
Example 55

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.78-2.98 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.52-3.72 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.79-3.84 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
¹³ C-NMR (D ₂ O 100 MHz): δ 42.1 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.7 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 70.6-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +).
Example 56

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.75 (s, 3H, C H 3 SO 3 -), δ 3.35-3.41 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.64-3.80 (m, 4H, HOC H 2 CH (N + H 3) C H 2 OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 38.5 (C H 3 SO 3 -), δ 54.2 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N ⁺ H ₃ ) C H ₂ OH).
Example 57

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.82-0.86 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.59-1.65 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 2.70 (s, 3H, C H 3 SO 3 -), δ 3.59 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3 ).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.4 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) _{, δ 38.5 (C H 3 SO} 3 -), δ 60.6 (NH 3 + C (CH 2 OH) 2 CH 2 CH 3), δ 61.2 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3) .
Example 58

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.72 (s, 3H, C H 3 SO 3 -), δ 3.65 (s, 6H, NH 3 + C (C H 2 OH) 3).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 38.5 (C H 3 SO 3 -), δ 59.4 (NH 3 + C (CH 2 OH) 3), δ 61.4 (NH 3 + C (C H 2 OH) ₃ ).
Example 59

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.71 (s, 3H, C H 3 SO 3 -), δ 2.95-3.15 (m, 2H, HOCH 2 (CH (OH)) 3 CH (OH) C H ^{_{2 NH 3 +), δ 3.53-3.73}} (m, 5H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 NH 3 +), δ 3.90-3.96 (m, 1H, HOCH 2 (CH _{(OH)) 3 C H (} OH) CH 2 NH 3 +).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 38.5 (C H 3 SO 3 -), δ 41.7 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 3 +), δ 62.7 (HO _{C H 2 (CH (OH)} ) 3 CH (OH) CH 2 NH 3 +), δ 68.9-70.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +).
Example 60

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.28-3.32 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.59-3.75 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.0 (HOCH 2 C H (N + H 3) CH 2 OH), δ 59.1 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 61

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.74 to 0.78 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.42-1.48 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 3.45 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 24. 1 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 58.8 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 62.1 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
<Example 62>

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.51 (s, 6 H, NH ₃ ⁺ C (C H ₂ OH) ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 69.1 (NH ₃ ⁺ C (CH ₂ OH) ₃ ), δ 61.0 (NH ₃ ⁺ C ( C H ₂ OH) ₃ ).
Example 63

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.86-3.05 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.41-3.68 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.83-3.88 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.7 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.6 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 69.2-70.8 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +).
Example 64

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.33-3.38 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 3.61-3.77 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 65

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.72 (t, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.49-1.51 (m, 2 H, NH ₃ ⁺ C (CH _{2 OH) 2 C H 2 CH} 3), δ 3.47 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.2 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 48.9 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 61.1 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
Example 66

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.37-3.43 (m, 1H, HOCH 2 C H (N + H 3) CH 2 OH), δ 3.66-3.81 (m, 4H, HOC H 2 CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.2 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.7 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 67

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.81-0.85 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.59-1.65 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 3.59 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.3 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 60.5 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 61.2 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
<Example 68>

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.67 (s, 6 H, NH ₃ ⁺ C (C H ₂ OH) ₃ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 59.4 (NH ₃ ⁺ C (CH ₂ OH) ₃ ), δ 61.5 (NH ₃ ⁺ C ( C H ₂ OH) ₃ ).
Example 69

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 2.98-3.17 (m, 2H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.54-3.75 (m, 5H, _{HOC H 2 (C H (OH} )) 3 CH (OH) CH 2 NH 3 +), δ 3.94-3.98 (m, 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 NH 3 + ).
¹³ C-NMR (D ₂ O 100 MHz): δ 41.7 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 62.7 (HO C H ₂ (CH (OH)) ₃ CH ^{_{(OH) CH 2 NH 3 +}} ), δ 69.0-71.0 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +).
<Example 70>

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 3.33-3.39 (m, 1 H, HOCH ₂ C H (N ⁺ H ₃ ) CH ₂ OH), δ 3.62-3.78 (m, 4 H, HOC H ₂ CH (N ⁺ H ₃ ) C H ₂ OH).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 54.1 (HOCH 2 C H (N + H 3) CH 2 OH), δ 58.6 (HO C H 2 CH (N + H 3) C H 2 OH).
Example 71

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.60 (t, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.35-1.41 (m, 2 H, NH ₃ ⁺ C (CH 2 _{2 OH) 2 C H 2 CH} 3), δ 3.35 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.2 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.1 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) , δ 48.7 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 60.8 (NH ₃ ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ).
<Example 72>

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.91 to 0.94 (m, 3 H, NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.68 to 1.73 (m, 2 H, NH ₃ ⁺ C _{(CH 2 OH) 2 C H} 2 CH 3), δ 3.67 (s, 4H, NH 3 + C (C H 2 OH) 2 CH 2 CH 3).
¹³ C-NMR (D ₂ O 100 MHz): δ 6.5 (NH ₃ ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 23.4 (NH ₃ ⁺ C (CH ₂ OH) ₂ C H ₂ CH ₃ ) _{^{, δ 60.7 (NH 3 + C}} (CH 2 OH) 2 CH 2 CH 3), δ 61.3 (NH 3 + C (C H 2 OH) 2 CH 2 CH 3), δ 120.2 (N (C N) 2 - ).
Example 73
The compound represented by the following formula was synthesized.

2-amino-2-ethyl-1,3-propanediol (10.00 g, 83.92 mmol) and 3-chloro-1,2-propanediol (46.38 g, 419.60 mmol) in 1-propanol 500 ml After reacting for 48 hours under reflux, 1-propanol was distilled off under reduced pressure, THF was added to the obtained liquid, and the mixture was heated and washed to obtain a white powder. Sodium hydroxide is added to the obtained white powder, and after stirring at room temperature for 2 hours, ethanol is added and the precipitated crystals are filtered off, and the filtrate is evaporated under reduced pressure, and the obtained liquid is subjected to column chromatography The reaction mixture was purified by the above to obtain amine compound 1 (11.35 g, 58.74 mmol) described in Example 73 in Table 11.

After reacting amine compound 1 (2.50 g, 12.94 mmol) and oleic acid (3.65 g, 12.94 mmol) in 50 ml of water at room temperature for 3 hours, water was distilled off under reduced pressure to obtain a yellow liquid. The obtained liquid was washed to obtain ammonium oleate (6.16 g, 12.94 mmol) as a yellow liquid.
FT-IR (KBr): 3398 cm ^-1 : OH stretching vibration 2922 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.86-0.92 (m, 6H, NH 2 + C (CH 2 OH) 2 CH 2 C H 3, C H 3 CH 2 CH 2), δ 1.27 (s, _{20H, CH 3 (C H 2} ) 6 CH 2, (C H 2) 4 CH 2 CH 2 COO -), δ 1.44 (m, 2H, NH 2 + C (CH 2 OH) 2 C H 2 CH 3) , δ 1.53 (s, 2H, C H 2 CH 2 COO -), δ 1.96-2.01 (m, 4H, C H 2 CHCHC H 2), δ 2.16 (t, 2H, CH 2 C H 2 COO -), δ 2.78-2.96 (m, 2H, NH 2 + C H 2 CH (OH)), δ 3.61-3.78 (m, 6H, NH 2 + C (C H 2 OH) 2 CH 2 CH 3, NH 2 + CH _{2 CH (OH) C H 2} OH), δ 3.83-3.88 (m, 1H, NH 2 + CH 2 C H (OH)), δ 5.32-5.38 (m, 2H, C H C H).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 9.6 (NH 2 + C (CH 2 OH) 2 CH 2 C H 3), δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H _{2 CH 2), δ 24.6 (} NH 2 + C (CH 2 OH) 2 C H 2 CH 3), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 (C H 2 CHCH C H 2), δ _{29.3-29.9 (CH 3 CH 2 CH 2} (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H 2), δ 37.5 (CH 2 C H ^{_{2 COO -), δ 43.6 (}} NH 2 + C (CH 2 OH) 2 CH 2 CH 3), δ 45.8 (NH 2 + C H 2 CH (OH)), δ 60.2 (NH 2 + C (C H 2 OH) ₂ CH ₂ CH ₃ ), δ 62.8 (NH ₂ ⁺ CH ₂ CH (OH) C H ₂ OH), δ 71.1 (NH ₂ ⁺ CH ₂ C H (OH) C H ₂ OH), δ 129.7-130.0 (C H C H), δ 181.8 (C OO -).
Example 74
The compound represented by the following formula was synthesized.

After reacting D-glucamine (10.00 g, 55.19 mmol) and 3-chloro-1,2-propanediol (30.50 g, 275.95 mmol) in 500 ml of 1-propanol under reflux for 48 hours, 1- Propanol was distilled off under reduced pressure, THF was added to the obtained liquid, and the mixture was heated and washed to obtain a white powder. Sodium hydroxide is added to the obtained white powder, and after stirring at room temperature for 2 hours, ethanol is added and the precipitated crystals are filtered off, and the filtrate is evaporated under reduced pressure, and the obtained liquid is subjected to column chromatography The reaction mixture was purified by the above to obtain amine compound 2 (7.05 g, 27.60 mmol) described in Example 74 of Table 11.

After reacting amine compound 2 (2.50 g, 9.79 mmol) and oleic acid (2.76 g, 9.79 mmol) in 50 ml of water at room temperature for 3 hours, water was distilled off under reduced pressure to obtain a yellow liquid. The obtained liquid was washed to obtain ammonium oleate (5.26 g, 9.79 mmol) as a yellow liquid.
FT-IR (KBr): 3344cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1554cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.90 (t, 3H, C H 3 CH 2 CH 2), δ 1.30 (s, 20H, CH 3 (C H 2) 6 CH 2, (C H 2) ₄ CH ₂ CH ₂ COO ⁻ ), δ 1.57 (s, 2 H, C H ₂ CH ₂ COO ⁻ ), δ 2.00−2.04 (m, 4 H, C H ₂ CHCHC H ₂ ), δ _2. 16 (t, 2 H, CH ₂ C H ₂ COO ⁻ ), δ 3.00 to 3.23 (m, 4 H, HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ NH ₂ ⁺ , NH ₂ ⁺ C H ₂ CH (OH)), δ 3.51-3.74 (m, 7H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 NH 2 +, NH 2 + CH 2 CH (OH) C H 2 OH), δ 3.94-3.98 (m , 1 H, NH ₂ ⁺ CH ₂ C H (OH), δ 4.03-4.09 (m, 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ NH ₂ ⁺ ), δ 5.32-5. 38 (m , 2H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.6 (C H 3 CH 2 CH 2), δ 23.8 (CH 3 C H 2 CH 2), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 ( _{C H 2 CHCH C H 2)} , δ 30.4-31.0 (CH 3 CH 2 CH 2 (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H _{2), δ 37.5 (CH 2} C H 2 COO -), δ 43.2 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 NH 2 +), δ 45.8 (NH 2 + C H 2 CH ( OH)), δ 62.8 (NH ₂ ⁺ CH ₂ CH (OH) C H ₂ OH), δ 64.7 (HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ NH ₂ ⁺ ), δ 70.7 − _{72.9 (HOCH 2 (C H (} OH)) 3 C H (OH) CH 2 NH 3 +, NH 2 + CH 2 C H (OH) C H 2 OH), δ 130.0-130.9 (C H C H), δ 182.7 (C OO ^-).
Example 75
The compound represented by the following formula was synthesized.

Amine compound 2 (10.00 g, 39.17 mmol) and 3-chloro-1,2-propanediol (43.90 g, 397.14 mmol) described in Example 74 of Table 11 in 500 ml of 1-propanol: After reacting at 130 ° C. for 4 hours under pressure, 1-propanol was distilled off under reduced pressure, THF was added to the obtained liquid, and the mixture was heated and washed to obtain a white powder. Sodium hydroxide is added to the obtained white powder, and after stirring at room temperature for 2 hours, ethanol is added and the precipitated crystals are filtered off, and the filtrate is evaporated under reduced pressure, and the obtained liquid is subjected to column chromatography The white powder was obtained by purifying with.

  The white powder was reacted with 3-chloro-1,2-propanediol (21.65 g, 195.90 mmol) in 500 ml of acetonitrile under pressure at 130 ° C. for 4 hours, and then the acetonitrile was distilled off under reduced pressure. The solid was added with THF and heated and washed to obtain a pale yellow powder.

  Water was added to this pale yellow powder, and water was passed through the anion exchange resin to obtain amine compound 3 (4.13 g, 9.80 mmol) described in Example 75 in Table 11.

After reacting amine compound 3 (4.13 g, 9.80 mmol) and isostearic acid (2.79 g, 9.80 mmol) in 50 ml of water at room temperature for 3 hours, water was distilled off under reduced pressure to obtain a yellow liquid. The resulting liquid was washed to obtain quaternary ammonium isostearate (6.92 g, 9.80 mmol) as a yellow liquid.
FT-IR (KBr): 3324cm -1: O-H stretching vibration 2920cm ^-1: C-H stretching vibration 1555cm ^-1: COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.83-0.90 (m, 6H, C H 3 (CH 2) 8 CH ((CH 2) 6 C H 3) COO -), δ 1.06-1.51 (m, _{28H, CH 3 (C H 2} ) 8 CH ((C H 2) 6 CH 3) COO -), δ 2.13-2.16 (m, 1H, CH 3 (CH 2) 8 C H ((CH 2) 6 CH ^{_{3) COO -), δ 3.00-3.23}} (m, 8H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +, N + C H 2 CH (OH)), δ 3.51-3.74 ( m, 11 H , HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ N ⁺ _, N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 3.94-3.98 (m, 3 H, N ⁺ CH ₂ C H (OH), δ 4.03-4.09 (m 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ N ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2), δ 22.7 (CH 3 C H-- 2 CH 2), δ 26.4 (C H 2 CH 2 CHCOO -), δ 30.0 ( _{CH 3 CH 2 CH 2 (C} H 2) 4 CH 2 CH 2 CH (CH 2 CH 2 (C H 2) 2 CH 2 CH 2 CH 3) COO -, CH 2 C H 2 CHCOO -), δ 31.9 ( ^{_{CH 3 CH 2 C H 2 -}} ), δ 37.7 (C HCOO -), δ 43.2 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +), δ 45.8 (N + C H 2 CH (OH)), δ 62.8 (N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 64.7 (HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ N ⁺ ), δ 70.7-72.9 _{(HOCH 2 (C H (OH} )) 3 C H (OH) CH 2 N +, N + CH 2 C H (OH) C H 2 OH), δ 182.1 (CH C OO -).
Example 76
The compound represented by the following formula was synthesized.

Amine compound 1 (10.00 g, 51.75 mmol) and 3-chloro-1,2-propanediol (57.20 g, 517.50 mmol) described in Example 73 in Table 11 in 500 ml of 1-propanol: After reacting at 130 ° C. for 4 hours under pressure, 1-propanol was distilled off under reduced pressure, THF was added to the obtained liquid, and the mixture was heated and washed to obtain a white powder. Sodium hydroxide is added to the obtained white powder, and after stirring at room temperature for 2 hours, ethanol is added, and the precipitated crystals are separated by filtration, and the filtrate is evaporated under reduced pressure, and the obtained liquid is used as silica gel. By purification, a white powder was obtained.

  The white powder was reacted with 3-chloro-1,2-propanediol (17.16 g, 155.25 mmol) in 500 ml of acetonitrile under pressure at 130 ° C. for 4 hours, and then the acetonitrile was distilled off under reduced pressure. The solid was added with THF and heated and washed to obtain a pale yellow powder.

Water was added to this pale yellow powder, and water was passed through the anion exchange resin to obtain amine compound 4 (5.58 g, 15.53 mmol) described in Example 76 of Table 11. Amine compound 4 (5.58 g, 15.53 mmol) and oleic acid (4.39 g, 15.53 mmol) were reacted in 50 ml of water at room temperature for 3 hours, and water was distilled off under reduced pressure to obtain a yellow liquid. The obtained liquid was washed to obtain quaternary ammonium oleate (9.97 g, 15.53 mmol) as a yellow liquid.
FT-IR (KBr): 3350 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.86-0.92 (m, 6H, N + C (CH 2 OH) 2 CH 2 C H 3, C H 3 CH 2 CH 2), δ 1.27 (s, 20H _{, CH 3 (C H 2)} 6 CH 2, (C H 2) 4 CH 2 CH 2 COO -), δ 1.44 (m, 2H, N + C (CH 2 OH) 2 C H 2 CH 3), δ 1.53 (s, 2H, C H 2 CH 2 COO -), δ 1.96-2.01 (m, 4H, C H 2 CHCHC H 2), δ 2.16 (t, 2H, CH 2 C H 2 COO -), δ 2.78 −2.96 (m, 6H, N ⁺ C H ₂ CH (OH)), δ 3.61-3. 78 (m, 10 H , N ⁺ C (C H ₂ OH) ₂ CH ₂ CH _3, N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 3.83-3.88 (m, 3 H, N ⁺ CH ₂ C H (OH)), δ 5.32-5. 38 (m, 2 H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 9.6 (N + C (CH 2 OH) 2 CH 2 C H 3), δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 _{CH 2), δ 24.6 (N} + C (CH 2 OH) 2 C H 2 CH 3), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 (C H 2 CHCH C H 2), δ 29.3- _{29.9 (CH 3 CH 2 CH 2} (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H 2), δ 37.5 (CH 2 C H 2 COO ⁻ ), δ 43.6 (N ⁺ C (CH ₂ OH) ₂ CH ₂ CH ₃ ), δ 45.8 (N ⁺ C H ₂ CH (OH)), δ 60.2 (N ⁺ C ( C H ₂ OH) ₂ CH ₂ CH ₃ ), δ 62.8 (N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 71.1 (N ⁺ CH ₂ C H (OH) C H ₂ OH), δ 129.7-130.0 ( C H C H), δ 181.8 (C OO ^-).
Examples 77 to 83
The compounds of Examples 77, 79 to 83 shown in Table 3 and Tables 11 and 12 were synthesized by the same synthesis method as in Example 75, at the compounding molar ratio described in Tables 11 and 12. In addition, the compound of Example 78 shown in Table 3 and Table 11 was synthesized by the same synthesis method as in Example 76 and the compounding molar ratio described in Table 11. Physical property values are shown below.
<Example 77>

FT-IR (KBr): 3350 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.86-0.92 (m, 3H, C H 3 CH 2 CH 2), δ 1.27 (s, 20H, CH 3 (C H 2) 6 CH 2, (C H _{2) 4 CH 2 CH 2 COO} -), δ 1.53 (s, 2H, C H 2 CH 2 COO -), δ 1.96-2.01 (m, 4H, C H 2 CHCHC H 2), δ 2.16 (t, 2H ^{_{, CH 2 C H 2 COO -}} ), δ 3.00-3.23 (m, 8H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +, N + C H 2 CH (OH)), δ 3.51-3.74 (m, 11H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 N +, N + CH 2 CH (OH) C H 2 OH), δ 3.94-3.98 (m, 3H , N ⁺ CH ₂ C H (OH), δ 4.03-4.09 (m 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ N ⁺ ), δ 5.32-5. 38 (m, 2 H, C H C H ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 14.1 (C H 3 CH 2 CH 2), δ 22.7 (CH 3 C H 2 CH 2), δ 26.3 (C H 2 CH 2 COO -), δ 27.2 ( _{C H 2 CHCH C H 2)} , δ 29.3-29.9 (CH 3 CH 2 CH 2 (C H 2) 4, (C H 2) 4 CH 2 CH 2 COO -), δ 31.9 (CH 3 CH 2 C H ₂ ), δ 37.5 (CH ₂ C H ₂ COO ⁻ ), δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ N ⁺ ), δ 45.8 (N ⁺ C H ₂ CH (OH) ), δ 62.8 (N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 64.7 (HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ N ⁺ ), δ 70.7-72.9 (HOCH _{2) (C H (OH)) 3} C H (OH) CH 2 N +, N + CH 2 C H (OH) C H 2 OH), δ 129.7-130.0 (C H C H), δ 181.8 (C OO - ).
<Example 78>

FT-IR (KBr): 3231cm -1: O-H stretching vibration 2937cm ^-1: C-H stretching vibration 1571cm ^-1: COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 0.86 (m, 3 H, N ⁺ C (CH ₂ OH) ₂ CH ₂ C H ₃ ), δ 1.17-1.24 (m, 3 H, C H ₃ CH (OH) ^{COO -), δ 1.44 (m} , 2H, N + C (CH 2 OH) 2 C H 2 CH 3), δ 2.78-2.96 (m, 6H, N + C H 2 CH (OH)), δ 3.61- ^{3.78 (m, 10H, N +} C (C H 2 OH) 2 CH 2 CH 3, N + CH 2 CH (OH) C H 2 OH), δ 3.83-3.88 (m, 3H, N + CH 2 C H (OH)), δ 3.94-3.99 ( m, 1H, CH 3 C H (OH) COO -).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 9.6 (N + C (CH 2 OH) 2 CH 2 C H 3), δ 20.0 (C H 3 CH (OH) COO -), δ 24.6 (N + C _{(CH 2 OH) 2 C H} 2 CH 3), δ 43.6 (N + C (CH 2 OH) 2 CH 2 CH 3), δ 45.8 (N + C H 2 CH (OH)), δ 60.2 (N + _{C (C H 2 OH) 2} CH 2 CH 3), δ 62.8 (N + CH 2 CH (OH) C H 2 OH), δ 68.5 (CH 3 C H (OH) COO -), δ 71.1 (N + _{CH 2 C H (OH) C} H 2 OH), δ 182.4 (CH 3 CH (OH) C OO -).
<Example 79>

FT-IR (KBr): 3350 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 1.17 to 1.24 (m, 3 H, C H ₃ CH (OH) COO ⁻ ), δ 3.00 to 3.23 (m, 8 H, HOCH ₂ (CH (OH)) ₃ CH ^{_{(OH) C H 2 N +}} , N + C H 2 CH (OH)), δ 3.51-3.74 (m, 11H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 N +, N _{^{+ CH 2 CH (OH) C}} H 2 OH), δ 3.94-3.98 (m, 4H, N + CH 2 C H (OH), CH 3 C H (OH) COO -), δ 4.03-4.09 (m 1H , HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ N ⁺ ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ 20.0 (C H 3 CH (OH) COO -), δ 43.2 (HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +), δ 45.8 (N ⁺ C H ₂ CH (OH)), δ 62.8 (N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 64.7 (HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ N _{^{+), δ 68.5 (CH 3}} C H (OH) COO -), δ 70.7-72.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 N +, N + CH 2 C H (OH _{) C H 2 OH), δ} 182.4 (CH 3 CH (OH) C OO -).
<Example 80>

FT-IR (KBr): 3350 cm ^-1 : OH stretching vibration 2930 cm ^-1 : CH stretching vibration 1560 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 2.66-2.83 (m, 4H, HOOCC H 2 C (OH) (COOH) C H 2 COO - δ 3.00-3.23 (m, 8H, HOCH 2 (CH (OH _{)) 3 CH (OH) C} H 2 N +, N + C H 2 CH (OH)), δ 3.51-3.74 (m, 11H, HOC H 2 (C H (OH)) 3 CH (OH) CH 2 _{^{N +, N + CH 2 CH}} (OH) C H 2 OH), δ 3.94-3.98 (m, 3H, N + CH 2 C H (OH)), δ 4.03-4.09 (m 1H, HOCH 2 (CH ( OH)) ₃ C H (OH) CH ₂ N ⁺ ).
¹³ C-NMR (D ₂ O 100 MHz): δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ N ⁺ ), δ 43.7 (HOOC C H ₂ C (OH) (COOH) C H ^{_{2 COO -), δ 45.8 (}} N + C H 2 CH (OH)), δ 62.8 (N + CH 2 CH (OH) C H 2 OH), δ 64.7 (HO C H 2 (CH (OH)) 3 ^{_{CH (OH) CH 2 N +}} ), δ 70.7-72.9 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 N +, N + CH 2 C H (OH) CH 2 OH), δ _{73.8 (HOOCCH 2 C (OH)} (COOH) CH 2 COO -), δ 174.7 (HOO C CH 2 C (OH) (COOH) CH 2 C OO -), δ 178.6 (HOOCCH 2 C (OH) (C OOH ) CH ₂ COO ^-).
<Example 81>

FT-IR (KBr): 3370 cm ^-1 : OH stretching vibration 2950 cm ^-1 : CH stretching vibration 1592 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.00-3.23 (m, 8H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +, N + C H 2 CH (OH)), δ 3.51-3.74 (m, 11 H , HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ N ⁺ _, N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 3.94-3.98 (m, 3H, N ⁺ CH ₂ C H (OH)), δ 4.03-4.09 (m 1 H, HOCH ₂ (CH (OH)) ₃ C H (OH) CH ₂ N ⁺ ), δ 6.80-6.86 (m, 2H, C (OH) C H CH, C (COO -) CHC H CH), δ 7.35-7.39 (m, 1H, C H CHC (OH)), δ 7.68-7.73 (m, 1H, C (COOH) C H CH).
¹³ C-NMR (D ₂ O 100 MHz): δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ N ⁺ ), δ 45.8 (N ⁺ C H ₂ CH (OH)), δ 62.8 _{^{(N + CH 2 CH (OH}} ) C H 2 OH), δ 64.7 (HO C H 2 (CH (OH)) 3 CH (OH) CH 2 N +), δ 70.7-72.9 (HOCH 2 (C H ( _{OH)) 3 C H (OH} ) CH 2 N +, N + CH 2 C H (OH) CH 2 OH), δ 116.2 (C (OH) C HCH), δ 118.0 (CH C (COO -) C ( OH)), δ 119.3 (C (COO -) CH C HCH), δ 130.5 (C (COO -) C HCH), δ 133.9 (C HCHC (OH)), δ 159.6 (C C (OH) C), ^{δ 175.5 (C C OO -)} .
<Example 82>

FT-IR (KBr): 3371 cm ^-1 : OH stretching vibration 2940 cm ^-1 : CH stretching vibration 1582 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 0.99 (s, 3H, C H 3 CH 2 OCH 2 COO -), δ 3.00-3.23 (m, 8H, HOCH 2 (CH (OH)) 3 CH (OH ) C ₂ H ₂ N ⁺ , N ⁺ C ₂ H ₂ CH (OH)), δ 3.34-3.39 (q, 2 H, CH ₃ C H ₂ OCH ₂ COO ⁻ ), δ 3.49 (m, 2 H, CH ₃ CH ₂ OC H ₂ COO ⁻ ), δ 3.51-3.74 (m, 11 H , HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ N ⁺ _, N ⁺ CH ₂ CH (OH) C H ₂ OH), δ ^{3.94-3.98 (m, 3H, N +} CH 2 C H (OH)), δ 4.03-4.09 (m 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 N +).
¹³ C-NMR (D ₂ O 100 MHz): δ 14.0 (C H ₃ CH ₂ O), δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ N ⁺ ), δ 45.8 (N ⁺ C H ₂ CH (OH)), δ 62.8 (N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 64.7 (HO C H ₂ (CH (OH)) ₃ CH (OH) CH ₂ N ⁺ ), δ 66.4 (CH ₃ C H ₂ O), δ 69.1 (CH ₃ CH ₂ O C H ₂ COO ⁻ ), δ 70.7-72.9 (HOCH ₂ ( C H (OH)) ₃ C H (OH) CH ₂ N ^{+ _{, N + CH 2 C H (}} OH) CH 2 OH), δ 178.1 (CH 3 CH 2 OCH 2 C OO -).
Example 83

FT-IR (KBr): 3388 cm ^-1 : OH stretching vibration 2959 cm ^-1 : CH stretching vibration 1676 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ 3.00-3.23 (m, 8H, HOCH 2 (CH (OH)) 3 CH (OH) C H 2 N +, N + C H 2 CH (OH)), δ 3.51-3.74 (m, 11 H , HOC H ₂ (C H (OH)) ₃ CH (OH) CH ₂ N ⁺ _, N ⁺ CH ₂ CH (OH) C H ₂ OH), δ 3.94-3.98 (m, _{^{3H, N + CH 2 C H}} (OH)), δ 4.03-4.09 (m 1H, HOCH 2 (CH (OH)) 3 C H (OH) CH 2 N +).
¹³ C-NMR (D ₂ O 100 MHz): δ 43.2 (HOCH ₂ (CH (OH)) ₃ CH (OH) C H ₂ N ⁺ ), δ 45.8 (N ⁺ C H ₂ CH (OH)), δ 62.8 _{^{(N + CH 2 CH (OH}} ) C H 2 OH), δ 64.7 (HO C H 2 (CH (OH)) 3 CH (OH) CH 2 N +), δ 70.7-72.9 (HOCH 2 (C H ( _{OH)) 3 C H (OH} ) CH 2 N +, N + CH 2 C H (OH) CH 2 OH), δ 114.9-117.8 (C F 3 COO -), δ 162.8-163.1 (CF 3 C OO - ).
Examples 84 and 85
The compounds of Examples 84 and 85 shown in Tables 1 and 12 were synthesized by the same synthesis method as in Example 1 and the compounding molar ratio described in Table 12. Physical property values are shown below.
Example 84

FT-IR (KBr): 3248 cm ^-1 : OH stretching vibration 2951 cm ^-1 : CH stretching vibration 1578 cm ^-1 : COO ^- stretching vibration
_{^{1 H-NMR (D 2 O}} 400MHz): δ1.66-1.89 (m, 4H, C H 2 C (OH) (COO -)), δ3.35 (m, 1H, CH (OH) C H (OH ) CH (OH)), δ3.50 (s, 6H, H 3 N + C (C H 2 OH) 3), δ3.79-3.95 (m, 2H, CH 2 C H (OH) CH (OH) ).
_{^{13 C-NMR (D 2 O}} 100MHz): δ37.3 (C H 2 C (OH) (COO -)), δ40.6 (C H 2 C (OH) (COO -)), δ59.9 (H ₃ N ⁺ C ( C H ₂ OH) ₃ , δ 60.4 (H ₃ N ⁺ C (CH ₂ OH) ₃ ), δ 66.9 (CH ₂ C H (OH) CH (OH)), δ 70.3 _{(CH 2 C H (OH)} CH (OH)), δ75.1 (CH (OH) C H (OH) CH (OH)), δ76.9 (CH 2 C (OH) (COO -)), δ181 _{.3 (CH 2 C (OH)} (C OO -)).
<Example 85>

FT-IR (KBr): 3240 cm ^-1 : OH stretching vibration 2980 cm ^-1 : CH stretching vibration 1571 cm ^-1 : COO ^- stretching vibration
¹ H-NMR (D ₂ O 400 MHz): δ 1.71-1.94 (m, 4 H, C H ₂ C (OH) (COO ⁻ )), δ 2.88-3.08 (m, 2 H, HOCH ₂ (CH (OH (OH) )) ₃ CH (OH) C H ₂ NH ₃ ⁺ ), δ 3.42 (m, 1 H, CH (OH) C H (OH) CH (OH)), δ 3.50-3.71 (m, 5 H, HOC H _{2 (C H (OH))} 3 CH (OH) CH 2 NH 3 +), δ3.88 (m, 2H, CH 2 C H (OH) CH (OH)), δ4.00 (m, 1H, HOCH _{2 (CH (OH)) 3} C H (OH) CH 2 NH 3 +).
_{^{13 C-NMR (D 2 O}} 100MHz): δ37.3 (C H 2 C (OH) (COO -)), δ40.6 (C H 2 C (OH) (COO -)), δ41.7 (HOCH _{2 (CH (OH)) 3} CH (OH) C H 2 NH 3 +), δ62.6 (HO C H 2 (CH (OH)) 3 CH (OH) CH 2 NH 3 +), δ66.9 ( _{CH 2 C H (OH) CH} (OH)), δ69.3-70.7 (HOCH 2 (C H (OH)) 3 C H (OH) CH 2 NH 3 +), δ70.8 (CH 2 C H ( OH) CH (OH)), δ75.2 (CH (OH) C H (OH) CH (OH)), δ77.0 (CH 2 C (OH) (COO -)), δ181.4 (CH 2 C ^{(OH) (C OO -)} ).
<Comparative Examples 1 to 73, 85, 86>
The compounds of Comparative Examples 1 to 73, 85 and 86 shown in Tables 1 to 3 and Tables 13 to 20 below were synthesized. The compounds of Comparative Examples 1 to 56 of Tables 13 to 18 and Comparative Examples 85 and 86 of Table 20 were synthesized by the same synthesis method as in Example 1 at compounding molar ratios described in Tables 13 to 18 and 20.

  The compounds of Comparative Examples 57 and 58 in Table 18 were synthesized based on Examples 73 and 74 at compounding molar ratios described in Table 18.

The compounds of Comparative Examples 59 to 73 of Tables 18 to 20 were synthesized based on Examples 75 and 76 at the compounding molar ratio described in Tables 18 to 20.
Comparative Example 74
As the compound of Comparative Example 74 shown in Table 21 below, a reagent manufactured by Wako Pure Chemical Industries, Ltd. was used.
Comparative Examples 75 and 76
The compounds of Comparative Examples 75 and 76 shown in Table 21 below were synthesized according to the method described in Patent Document 4.
Comparative Examples 77 and 78
The compounds of Comparative Examples 77 and 78 shown in Table 22 below were synthesized in the same manner as in Example 1 using dimethylethanolamine or choline hydroxide and glycolic acid.
Comparative Example 79
The compound of Comparative Example 79 represented by the following formula was synthesized according to the method described in Non-patent Document 2 (mp 119 ° C.).

Comparative Example 80
In the compound of Comparative Example 80 represented by the following formula, an aqueous tetrabutylammonium bromide solution is passed through a column filled with an anion exchange resin, lactic acid is added to the obtained aqueous solution, and after stirring, the solvent is distilled off under reduced pressure, It synthesize | combined by washing | cleaning (mp110 degreeC).

Comparative Example 81
The compound of Comparative Example 81 represented by the following formula was synthesized according to the method described in Patent Document 4.

Comparative Example 82
The compound of Comparative Example 82 represented by the following formula was synthesized in the same manner as in Example 1 for triethanolamine and lactic acid.

Comparative Example 83
In the compound of Comparative Example 83 represented by the following formula, an aqueous solution of tetrabutylammonium bromide is passed through a column packed with an anion exchange resin, tartaric acid is added to the obtained aqueous solution, and after stirring, the solvent is distilled off under reduced pressure, It was synthesized by washing.

Comparative Example 84
The compound of Comparative Example 84 represented by the following formula was synthesized in the same manner as in Example 1 for triethanolamine and tartaric acid.

Comparative Example 96
The compounds of Comparative Example 96 shown in Table 24 and Table 27 were synthesized in the same manner as in Example 1 using triethanolamine and levulinic acid (mp 30 ° C.).

The following measurement and evaluation were performed using the above-mentioned Example and comparative example compound.
1. Properties at room temperature (25 ° C.) The compounds of Examples 1 to 83 and Comparative Examples 1 to 73, 85, 86 are added to a screw tube and dried under reduced pressure to be liquid as an anhydride at room temperature (25 ° C.) It was confirmed. In addition, the screw was tilted to observe the fluidity of the ionic liquid. Furthermore, the ionic liquid was allowed to stand in a low temperature incubator set at -5 ° C for 24 hours, and then allowed to stand at -10 ° C for 24 hours, and the properties (liquid, solid) were confirmed. The results are shown in Tables 1 to 20. “Liquid” in Tables 1 to 3 indicates that it is liquid at room temperature (25 ° C.), “solid” indicates that it is solid at room temperature (25 ° C.), and melting points (mp) in Tables 4 to 20 (° C.) is shown at less than −10 ° C. (<−10), −10 ° C. to less than −5 ° C. (−10 ≦ − <− 5), above 25 ° C. (25 <).

  As a result, the compounds of Examples 1 to 85 were liquid having fluidity.

  This is because the hydrophilic room temperature ionic liquid of the present invention has a larger number of hydroxyl groups which are anionic and electron donating groups in the cation, so that the cationicity of the entire quaternary ammonium cation is weak and sterically bulky. Because it is high, the interaction with the anion is reduced. In addition, the presence of two or more hydroxyl groups in a single substituent is considered to cause repulsion with an adjacent anion, making it difficult to pack, resulting in low crystallinity and a tendency to become liquid.

That is, the hydrophilic room temperature ionic liquid of the present invention has a cationic structure that tends to be liquid by using a polyhydroxyalkyl group as compared to the conventional ionic liquid using quaternary ammonium cation (for example, Patent Document 4). It has been found that the influence on the melting point by the choice of functional groups and characteristic groups in structural design and that a wide variety of anions can be applied.
2. Solubility in water The solubility in water was measured for the compounds of Examples 1-85 and Comparative Examples 74-76. The solubility in water was measured by the following method. Based on the moisture content measured by a differential thermal thermal simultaneous measurement device (TG / DTA), the ionic liquid and water are charged in the screw tube so as to obtain a predetermined concentration, and then after stirring for 30 minutes at 25 ° C. The solution was allowed to stand for 10 minutes, the solubility was visually confirmed, and the amount (g) of the ionic liquid dissolved in 100 g of water at 25 ° C. was defined as the solubility (g / 100 g water). The results are shown in Tables 4-12 and 21.

  As a result, while all of the ionic liquids of Comparative Example 74 and Comparative Examples 75 and 76, which are general hydrophilic ionic liquids, have a solubility in water of less than 600 g / 100 g water, all of the example compounds It melt | dissolved more than 1200g / 100g water.

  The hydrophilic room temperature ionic liquid of the present invention has no substituent consisting of only a hydrophobic alkyl group as a cation, and is a cation of only a hydrogen atom capable of hydrogen bonding with a water molecule, a (poly) hydroxyalkyl group, It has multiple hydrogen bonding sites in one ionic liquid molecule, and it can be hydrated with more water molecules. In addition, since the hydrophobicity due to the alkyl group and the alkylene group in the cation is reduced because two or more hydroxyl groups exist in one substituent, the affinity with water is high and the high water solubility is exhibited. it is conceivable that.

  That is, the hydrophilic room temperature ionic liquid of the present invention has high water solubility, and is expected to be developed for various applications.

3. Biodegradability Test The compounds of Examples 19, 20 and Comparative Examples 77, 78 shown in Table 22 were tested for biodegradability. The biodegradability test was conducted in accordance with the OECD Test Guideline 301C method. In this test, general activated sludge is used as a microorganism source, and each 300 ml of a standard test culture solution prepared is fed with a concentration of 30 mg / l of the microorganism source and 100 mg / l of a test substance, 25 ± 1 ° C., test For a period of 28 days, aniline was used as a standard substance. The biochemical oxygen demand (BOD) was measured using an Actac BOD sensor, and the decomposition rate (decomposition rate) was calculated from the calculated theoretical oxygen demand value. The results are shown in Table 22.

  As a result, compared with the compounds of Comparative Examples 77 and 78, the compounds of Examples 19 and 20 had a degradation rate of 100% in a short period of time, and the biodegradability rate was fast.

  That is, it is recognized that the cation has no substituent composed of only a hydrophobic alkyl group, but is a cation of only a hydrogen atom and a (poly) hydroxyalkyl group, and the cation structure has an influence on the biodegradable rate. The environmental load can be reduced and the environmental suitability is excellent.

4. Protein dissolution test
[Protein (cytochrome C) dissolution concentration]
The concentrations of dissolved proteins in the compounds of Examples shown in Table 23 and Table 24, Comparative Examples 79 to 81, 87 and Comparative Example 96 (solid at room temperature (25 ° C.), melting point 30 ° C.) were measured. A predetermined concentration of protein (cytochrome C Horse Heart molecular weight 12384) was added to the ionic liquid shown in Tables 23 and 24 at room temperature (25 ° C.), and after mixing, the dissolution of the protein was visually determined. The dissolution of the protein in each example was performed with the amount of water in the ionic liquid being about 7 to 12%. Since the compounds of Comparative Examples 79, 80 and 96 were solid at room temperature, the compounds of Comparative Examples 79, 80 and 96 were good against Cytochrome C, referring to the dissolution test method of Cytochrome C of Non Patent Literature (Chemical Communications, 2005, 4804-4806). It dissolved in water which is a solvent, and evaluated in 85% aqueous solution (Table 23, 24 protein (cytochrome C) dissolution concentration (1)). For the compounds of Examples 23, 24, 42, 43, 84, 85, and Comparative Examples 79 to 81, 96, the moisture content is kept constant (14% ± 0.5%), and the protein solubility is similarly measured again. did. The water content was measured by the Karl Fischer method. (Table 23, 24 protein (cytochrome C) dissolution concentration (2)). It was evaluated that the solution was transparent and homogeneous and the state of complete dissolution was ○, and the state in which the remaining of cytochrome C could be visually confirmed was x, and the results are shown in Tables 23 and 24.

  As a result, in Tables 23 and 24, since the dissolution concentration of protein (cytochrome C) 24 (1), the compounds of Comparative Examples 79 to 81 and 96 are each 40.0 mg / mL or less, and the compound of Comparative Example 80 is less than 37 mg / mL. On the other hand, all of the Example compounds showed a solubility of 50 mg / mL or more, and in particular, the compound of Example 34 showed a high solubility of 75 mg / mL or more.

  In the proteins (cytochrome C) dissolution concentrations (2) in Tables 23 and 24, even for the compounds of Examples 23, 24, 42, 43, 84, 85 and Comparative Examples 79 to 81, 96, the moisture content is constant. Similarly, when the protein solubility was re-measured, the protein solubility was slightly increased overall, but the order of solubility of the ionic liquid to protein was the same, and the tendency of solubility was common.

  In addition, the compound of Comparative Example 96 has lower solubility in cytochrome C than Examples 23, 24, 42, 43, 84, 85, and the monocarboxylate anion having a ketone group has a protein compared to other anions. The solubility tended to be low.

  That is, the cation of the hydrophilic room temperature ionic liquid of the present invention has a multipoint hydrogen bonding site composed of a hydrogen atom or a polyhydroxyalkyl group, and is a hydrogen bond accepting property by utilizing sterically bulky structural features It is considered that a stable structure, more hydrogen bonds were formed with cytochrome C, and the compound exhibited higher solubility than the comparative example compound.

  Furthermore, when an anion has a hydroxyl group or a carboxyl group or the like in which hydrogen and oxygen having high electronegativity are covalently bonded, a stable structure and hydrogen bond can be obtained by two molecules of cytochrome C and hydrogen bond sites of both anion and cation. It is thought that the solubility improves because the ionic liquid can enter the intermolecular structure of cytochrome C, keep the intermolecular distance of cytochrome C constant, and reduce the intermolecular interaction.

That is, it was shown that the hydrophilic room temperature ionic liquid of the present invention dissolves cytochrome C at a high concentration and is useful as an alkaline protein dissolving solvent.
Long-term stability
Regarding the compounds of Examples 23, 24, 42, 43, 84, 85 and Comparative Examples 79, 87, cytochrome C was dissolved in a sample in which the moisture content in the ionic liquid was constant (14% ± 0.5%), The structural change (denaturation) of the protein in the ionic liquid was confirmed by the following method. As Comparative Example 87, 50 mM phosphate buffer (prepared with 50 mM potassium dihydrogen phosphate and 50 mM dipotassium hydrogen phosphate), which is a general solvent for dissolving proteins, was used as a sample immediately after dissolving the protein as well. The same check was made.

First, the change in the amide absorption by IR spectrum was confirmed in detail, and the higher-order structure (turn, α-helix, random coil, β-sheet) of the protein upon dissolution was confirmed. The amide I region (16000-1700 cm ^-1 ) and the amide II region (1500-1600 cm ^-1 ) were measured using the ATR method with a Fourier transform infrared spectrophotometer (FT / IR-6100 Japan Spectroscopy), and cytochrome C was not detected. The peak was detected from the difference between the dissolved ionic liquid sample (blank) and the ionic liquid sample in which cytochrome C was dissolved.

Moreover, the active state (Fe ²⁺ : reduced type, Fe ³⁺ : oxidized type) of cytochrome C was confirmed by the absorption of the UV spectrum. A UV-visible spectrophotometer (V) immediately after diluting an ionic liquid sample in which cytochrome C is dissolved to 1% with 50 mM phosphate buffer (prepared with 50 mM potassium dihydrogen phosphate and 50 mM dipotassium hydrogen phosphate) at pH = 7.4. Measurement with a quartz cell having a light path width of 2 mm according to JASCO-550.

  The results are shown in Tables 23 and 24.

In the identification of amide absorption by IR spectrum, the higher-order structure of the protein at the time of dissolution is compared with the literature value (Chem. Commun 2005, 4804-4806 Biomacromolecules 2010, 11, 2944-2948, Protein Science Society Archive, 2, e 054 (2009)). It confirmed by contrast. An IR measurement of the powder of cytochrome C before dissolution shows absorption at 1645 cm ^-1 in the amide I region and 1537 cm ^{-1 in the} amide II region,
It was denatured into a random coil. Next, it was confirmed that cytochrome C (comparative example 87) in the phosphate buffer was not denatured (amide I region: 1653 cm ⁻¹ , amide II region: 1547 cm ⁻¹ ), and had an α-helix structure. Cytochrome C in the ionic liquid of Examples 23, 24, 42, 43, 84, 85 has a measurement result equivalent to that of the phosphate buffer (Amid I region: 1652-1655 cm ^-1 ,
In the amide II region: 1545-1549 cm ^-1 ), it was confirmed that none of them had the denatured structure but maintained the α-helix structure. That is, it was shown that the ionic liquids of Examples 23, 24, 42, 43, 84 and 85 exhibited the effect of refolding even under high concentration conditions and dissolved cytochrome C without being denatured.

Cytochrome C reversibly changes to Fe ²⁺ (reduced) and Fe ³⁺ (oxidized) during intracellular electron transfer, maintains the secondary structure in the active state, and reduces in UV spectrum absorption The type has peaks at 550 nm in the α band, 521 nm in the β band, and 415 nm in the γ band, and in the oxidized type, the α band and the β band do not have clear peaks and shift to a low wavelength around 396 nm in the γ band. In the inactivated state, denaturation occurs, and the peaks of the α band, β band and γ band disappear. Cytochrome C in the ionic liquid of Examples 23, 24, 42, 43, 84, 85 gives substantially the same peak as compared with the peak of the phosphate buffer of Comparative Example 87, and the α band, β band, γ A reduced type peak was shown in each of the bands. This confirms that the cytochrome C stored in the ionic liquid maintains the secondary structure in the reduced active state.

  Next, ionic liquid samples in which cytochrome C was dissolved at respective maximum concentrations were subjected to 0 ° C., 25 ° C. (Examples 23, 24, 42, 43, 84, 85, Comparative Examples 79, 87), 80 ° C. (Example 23) , 24 and Comparative Examples 79 and 87), and by the measurement similar to the above IR and UV spectra, it was confirmed whether or not the cytochrome C was structurally changed, ie, not denatured. The results are shown in Tables 23 and 24.

  In Comparative Example 87 in which phosphate buffer was used, denaturation was confirmed within 1 week at 0 ° C. and within 1 day at 25 ° C., while the samples of the example were 180 days at 0 ° C. and 90 days at 25 ° C. However, it was shown that there was no change in the numerical values of IR and UV, and no structural change. Favorable results were obtained at 80 ° C. as compared with Comparative Example 87 using a phosphate buffer. In Comparative Example 79, the structure could not be maintained for 1 day (24 hours) at 80 ° C., and the ionic liquid of Examples 23 and 24 was modified for 1 day (24 days), while it was denatured immediately after dissolution. It showed that it did not denature, and was superior to long-term stability like an ionic liquid like comparative example 79 for time).

  That is, the hydrophilic room temperature ionic liquid of the present invention was an excellent protein storage solvent which does not denature the protein for a long time under high concentration and room temperature conditions, and was further shown to be useful as a protein refolding agent .

[Protein (hemoglobin, albumin) dissolution concentration]
As a protein, in addition to the above-mentioned cytochrome C (alkaline), the solubility of the ionic liquid in hemoglobin (neutral) and albumin (acidic) was confirmed. With respect to the compounds of Examples 23, 24, 42, 43, 84, 85 and Comparative Examples 79, 80, hemoglobin and albumin are dissolved in a predetermined concentration in a sample having a constant moisture content (14% ± 0.5%), The concentration of dissolved protein was measured in the same manner as in the case of cytochrome c. The results are shown in Tables 25 and 26.

  As a result, the solubility of hemoglobin and albumin by the ionic liquid of the example was both higher than that of the comparative example, and high solubility was confirmed with the same tendency as the above-mentioned cytochrome C.

  That is, the hydrophilic room temperature ionic liquid of the present invention was shown to be useful as a neutral and acidic protein dissolving solvent.

5. DNA lysis test
[Method of extracting DNA]
Neutral detergent (anionic surfactant) (1.5 g) was dissolved in water (200 g) and mixed with chicken liver (47 g) in a mixer for 2 minutes. A 2 mol / l aqueous solution of NaOH (250 ml) was added thereto, and the mixture was lightly stirred and heated at 100 ° C. for 5 minutes. After heating, the temperature was returned to normal temperature, and centrifugation (3000 rpm, 15 minutes) was performed to recover the filtrate.

The collected filtrate was cooled to 0-5 ° C, and ethanol (500 ml) cooled to 0-5 ° C was gently added thereto. Thereafter, the mixed solution was kept at 0 to 5 ° C., and the precipitated DNA was recovered with a Pasteur pipette. The recovered DNA was lyophilized with liquid nitrogen and stored in a cold place.
[DNA lysis concentration]
For the compounds of Examples 20-24, 28, 30, 34, 43, 56, 58 and Comparative Examples 79, 80, 96 shown in Table 27, the concentration of dissolved DNA was measured. The ionic liquid of each example was measured for water content by the Karl Fischer method, and was prepared so that the water content was 14% ± 0.5%. In addition, since the compounds of Comparative Examples 79 and 96 were solid at room temperature, 14 with water which is a good solvent for DNA, 14 was referred to in reference to the dissolution test method of Cytochrome C of Non Patent Literature (Chemical Communications, 2005, 4804-4806). It melt | dissolved and evaluated so that it might become% +/- 0.5%. A predetermined concentration of DNA extracted by the above method was added to these compounds at room temperature (25 ° C.), and after mixing, the dissolution of DNA was visually determined. The solution was clear and homogeneous, and the state of complete dissolution was evaluated as ○, and the state in which the remaining DNA could be visually confirmed was evaluated as x. The results are shown in Table 27.

  As a result, all of the ionic liquids of Examples exhibited high solubility in DNA as compared with Comparative Examples. In addition, the compound of Comparative Example 96 has lower solubility in DNA than Examples 20-24, 28, 30, 34, 43, 56, 58, and the monocarboxylate anion having a ketone group is compared with other anions. The DNA had a tendency to be less soluble.

  The DNA maintains a double helix structure in the active state, and has a peak at around 260 nm in the absorption of the UV spectrum, but when denatured, the relative absorbance of the UV absorption of the DNA greatly increases. A peak representing the absorption of DNA in the ionic liquid solution is obtained at 258 nm from the difference between the 0.1 wt% DNA solution and the ionic liquid sample (blank) in which no DNA is dissolved in any of the example compounds shown in Table 27. It is a peak similar to the absorption (259 nm) of the dissolved (1 wt%) DNA, and it was confirmed that the DNA dissolved in the ionic liquid retains a double helix structure in an active state.

  Next, a solution of the DNA in the example compound at the highest concentration shown in Table 27 was stored at 0 ° C, 25 ° C and 80 ° C, diluted to 0.1 wt% with water, and similarly subjected to UV measurement (80 ° C The stored sample was measured by quenching at 25 ° C.), and the change in the double helix structure of the DNA, ie, whether it was denatured or not was confirmed. The UV absorption of the example samples stored at 0 ° C., 25 ° C. and 80 ° C. both have peaks at 258 nm, almost no increase in relative absorbance is seen, the DNA is not denatured, and the double helix structure is retained And was in an active state.

  That is, it was shown that the hydrophilic room temperature ionic liquid of the present invention is excellent in storage stability to DNA and is useful as a dissolution solvent for nucleic acid such as DNA.

6. Carbonyl group containing compound solubility test (solubility test of methyl ethyl ketone)
About the compound of each Example and comparative example 83 which are shown in Table 28, 0.5g of methyl ethyl ketone was added to 0.5g of each compound, it mixed for 10 minutes with a magnetic stirrer, and the dissolution state was confirmed visually. The results are shown in Table 28.

  As a result, all of the example compounds dissolved methyl ethyl ketone, but the comparative example 83 having no hydroxyl group in the cation was separated and insoluble.

  That is, the hydrophilic room temperature ionic liquid of the present invention has a structural feature in which the quaternary ammonium cation is composed of a cation having a hydrogen bond donating property, an electron donating property and a coordinating property hydrogen atom and a polyhydroxyalkyl group. It was considered that the affinity to methyl ethyl ketone having a hydrogen bond accepting carbonyl group was high and it was dissolved to be useful, and it was shown to be useful as a solvent for dissolving a hydrogen bondable material such as an organic compound.

7. Metal Oxide Dispersion Test For the compounds of Examples and Comparative Examples 82 to 84 shown in Table 29 and Table 30, 0.5 g of each compound and zirconium oxide (IV) (Wako Pure Chemical Industries, Ltd., reagent special grade, about 5 A dispersion state after mixing of 0.5 g of 1 to 30 .mu.m and 0.5 g with a rotation and revolution mixer (Shinky Co., Ltd., ARE-310) at 2000 rpm for 1 min.times.5 times was visually confirmed. A state where the zirconium oxide was dispersed and the dispersion had a low viscosity was evaluated as ◎, a state where the dispersion was dispersed but thickened was evaluated as ○, and a state where it was not dispersed and precipitated was evaluated as x. The results are shown in Table 29 and Table 30.

  As a result, in each of the example compounds, zirconium oxide was well dispersed, and a low viscosity dispersion liquid with good handling was obtained. On the other hand, in the compound of Comparative Example 83, zirconium oxide immediately settled and did not disperse. The compounds of Comparative Examples 82 and 84 were thickened although the zirconium oxide was dispersed.

  That is, the hydrophilic room temperature ionic liquid of the present invention is structurally composed of a quaternary ammonium cation, a cation having a polyhydroxyalkyl group having many hydrogen bond donating, electron donating and coordinating hydroxyl groups. It is considered that the affinity to hydrogen bond acceptability and electron acceptability with zirconium oxide is enhanced, and zirconium oxide is well dispersed, and it is useful as a solvent for dissolving or dispersing hydrogen bondable materials such as inorganic compounds. It was shown to be.

8. Specific Heat Capacity Measurement Test Specific heat capacity measurement was performed on the compounds of Examples 19 to 24, 33, 37, and 43 and Comparative Examples 74, 79 to 81, and 88 to 95 shown in Table 31. The specific heat capacity measurement test was measured according to JIS K 7123.

  The test used α-alumina as a reference material. Use a container made of aluminum for the measurement container and collect 15 mg of the sample or reference material, and weigh it precisely, and measure the heat flux differential scanning calorific value by DSC under the conditions of measurement temperature -90 to 90 ° C and heating rate 10 ° C / min. It measured. The specific heat capacity was calculated using the following equation. The results are shown in Table 31.

As a result, the comparative example compound is 2.22 J / g · ° C. at −50 ° C., 2.39 J / g · ° C. at −20 ° C., 2.37 J / g · ° C. at 0 ° C., 2.39 J / g · ° C. at 20 ° C. The compound of Example shows high specific heat capacity at any temperature compared with the compound of Comparative Example at a temperature of 2.62 J / g · ° C. and 2.63 J / g · ° C. or less at 80 ° C. showed that. The specific heat capacity of the example compound was significantly improved as compared with the ionic liquid of JP-A-2012-241018 among the compounds of the comparative examples.

  That is, since the hydrophilic room temperature ionic liquid of the present invention has a hydrogen atom or a hydroxyalkyl group as a cation, and a hydrogen bonding functional group such as a hydroxyl group or an ether group as an anion, hydrogen can be generated in the molecule and between molecules The specific heat capacity is increased due to the formation of a bond and strong interaction with molecules and intramolecules, which is considered to exhibit high heat storage property as compared with the comparative example compound, and the heat medium, further, for example, metal, etc. It has been shown to be highly effective in cooling the friction heat generated during processing and friction of the medium, and to be useful as a water-soluble lubricating oil because of its nonflammability, non-volatility and low environmental impact.

Claims (8)

A hydrophilic room temperature ionic liquid which is liquid at room temperature (25 ° C.) and contains a cation and an anion, wherein the cation and the anion are any combination of the following (1) to (9): Hydrophilic room temperature ionic liquids:
(1) The cation has the following formula:
R ¹ is a linear or branched polyhydroxyalkyl group having 2 to 8 carbon atoms having two or more hydroxyl groups, and a primary ammonium cation in which R ² is a hydrogen atom and n is 1 Yes, the anion is one of the following;
Saturated aliphatic monocarboxylic acid anion having a branched chain having 5 to 22 carbon atoms
Linoleate anion
(R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3; 3 R ² and 2 × s R ³ each independently represent a hydrogen atom or a hydroxyl group In the formula, the total number of hydroxyl groups is 1 to 2.) saturated hydroxy monocarboxylic acid anion represented by the formula : saturated hydroxy di or tri carboxylic acid anion having 4 to 6 carbon atoms and 1 to 3 hydroxy groups.
Alkyl ether carboxylate anion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent an integer of 1 to 4)
Methanesulfonate ion (CH ₃ SO ₃ ^-), or ethane sulfonic acid ion _{^{(CH 3 CH 2 SO 3 -}} )
BF ₄ ^-
NO ₃ ^-
(2) The cation is a primary ammonium cation having one 1,3-dihydroxy-iso-propyl group, and the anion is any of the following;
HCOO ^-
Saturated aliphatic monocarboxylic acid anion represented by CH ₃ (CH ₂ ) _p COO ⁻ (p represents an integer of 0 to 1). Saturated aliphatic monocarboxylic acid anion having a branched chain having 5 to 22 carbon atoms.
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 Unsaturated aliphatic monocarboxylic acid anion represented by
Linoleate anion
HOCH ₂ COO ⁻ or (R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3 and 3 R ² and 2 × s R ³ are each independently And the total number of hydroxyl groups is 1 to 2.) a saturated hydroxymonocarboxylic acid anion represented by
Saturated dicarboxylic acid anion represented by HOOC (CH ₂ ) _x COO ⁻ (x is an integer of 1 to 3). Malate anion, tartrate anion, or HOOCC (R ⁴ R ⁵ ) C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represent a hydrogen atom, a hydroxyl group or a carboxyl group, and a total of 1 to 2 hydroxyl groups and a total of 0 to 1 carboxyl groups). Saturated hydroxydi or tricarboxylic acid anion salicylic acid anion mandelic acid anion C3-C22 saturated carbonyl monocarboxylic acid anion
Alkyl ether carboxylic acid anion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent integers of 0 to 4) The proton is dissociated from trifluoroacetic acid or pentafluoropropionic acid Halogen carboxylic acid anion halide ion
Methanesulfonate ion (CH ₃ SO ₃ ^-), or ethane sulfonic acid ion _{^{(CH 3 CH 2 SO 3 -}} )
BF ₄ ^-
Sulfate ion (SO ₄ ^2-), nitrate ion _{^{(NO 3 -), (2-}} CO 3) carbonate ions, or phosphate ion (H ₂ PO ₄ ^-)
(3) The cation is a primary ammonium cation having one 1,3-dihydroxy-2-ethyl-iso-propyl group, and the anion is any of the following:
CH ₃ (CH ₂ ) _p COO ⁻ (p represents an integer of 2 to 4) Any saturated aliphatic monocarboxylic acid anion A saturated aliphatic monocarboxylic acid having a branched chain having 5 to 22 carbon atoms Anion
Linoleate anion
(R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3; 3 R ² and 2 × s R ³ each independently represent a hydrogen atom or a hydroxyl group And the total number of hydroxyl groups is 1 to 2.) saturated hydroxymonocarboxylic acid anion represented by
HOOC (CH _{2) 2} COO ^-
Malate anion, tartrate anion, or HOOCC (R ⁴ R ⁵ ) C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represent a hydrogen atom, a hydroxyl group or a carboxyl group Saturated hydroxydi or tricarboxylic acid anion represented by 1 to 2 hydroxyl groups in total and 0 to 1 carboxyl groups in total). Saturated carbonyl monocarboxylic acid anion having 3 to 22 carbon atoms.
Alkyl ether carboxylic acid anion halide ion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent an integer of 1 to 4)
Methanesulfonate ion (CH ₃ SO ₃ ^-), or ethane sulfonic acid ion _{^{(CH 3 CH 2 SO 3 -}} )
BF ₄ ^-
Sulfate ion (SO ₄ ^2-), nitrate ion _{^{(NO 3 -), (2-}} CO 3) carbonate ions, or phosphate ion (H ₂ PO ₄ ^-)
Dicyanamide ion _{^{(N (CN) 2 -)}} , tricyanopropene meth acetonide ions _{^{(C (CN) 3 -)}} , or thiocyanate ion (SCN ^-)
(4) The cation is a primary ammonium cation having one 1,3-dihydroxy-2-hydroxymethyl-iso-propyl group, and the anion is any of the following;
Saturated aliphatic monocarboxylic acid anion having a branched chain having 5 to 22 carbon atoms
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 Unsaturated aliphatic monocarboxylic acid anion represented by
Linoleate anion
(R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3; 3 R ² and 2 × s R ³ each independently represent a hydrogen atom or a hydroxyl group indicates the total number of hydroxyl groups is 1-2.) saturated hydroxy monocarboxylic acids represented by anion <br/> quinic acid anion emission <br/> malic acid anions, tartrate anions, or HOOCC, (R ⁴ R ⁵⁾ C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represent a hydrogen atom, a hydroxyl group or a carboxyl group, wherein the total number of hydroxyl groups is 1 to 2 and the number of carboxyl groups is 0 Saturated hydroxydi or tricarboxylic acid anion represented by (1) to 3) saturated carbonyl monocarboxylic acid anion having 3 to 22 carbon atoms
Alkyl ether carboxylate anion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent an integer of 0 to 4)
Methanesulfonate ion (CH ₃ SO ₃ ^-), or ethane sulfonic acid ion _{^{(CH 3 CH 2 SO 3 -}} )
BF ₄ ^-
NO ₃ ^-
(5) The cation is a primary ammonium cation having one pentahydroxy-n-hexyl group, and the anion is any of the following;
Saturated aliphatic monocarboxylic acid anion represented by CH ₃ (CH ₂ ) _p COO ⁻ (where p represents an integer of 0 to 1). Saturated aliphatic monocarboxylic acid anion having a branched chain having 5 to 22 carbon atoms.
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 Unsaturated aliphatic monocarboxylic acid anion represented by
Linoleate anion
HOCH ₂ COO ⁻ or (R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3 and 3 R ² and 2 × s R ³ are each independently Is a hydrogen atom or a hydroxyl group, and the total number of hydroxyl groups is 1 to 2.) a saturated hydroxymonocarboxylic acid anion quinic acid anion
HOOC (CH _{2) 2} COO ^-
Malate anion, tartrate anion, or HOOCC (R ⁴ R ⁵ ) C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represent a hydrogen atom, a hydroxyl group or a carboxyl group Saturated hydroxydi or tricarboxylic acid anion represented by 1 to 2 hydroxyl groups and 0 to 1 carboxyl groups.
Salicylic acid anion
Alkyl ether carboxylic acid anion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent integers of 0 to 4) The proton is dissociated from trifluoroacetic acid or pentafluoropropionic acid Halogen carboxylic acid anion
Br ^-
Methanesulfonate ion (CH ₃ SO ₃ ^-), or ethane sulfonic acid ion _{^{(CH 3 CH 2 SO 3 -}} )
BF ₄ ^-
NO ₃ ^-
(6) The cation has the following formula:
And R ¹ is a linear or branched polyhydroxyalkyl group having 2 to 8 carbon atoms having two or more hydroxyl groups, and a secondary ammonium cation in which R ² is a hydrogen atom and n is 2 Yes, the anion is:
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 shown. unsaturated aliphatic represented by) a monocarboxylic acid anion emission
(7) The cation has the following formula:
In expressed, R ¹ is a hydroxyl group are shown two or more having a straight-chain or branched polyhydroxyalkyl group having 2 to 8 carbon atoms or a quaternary ammonium cation and n is 4, A anion is, One of the following;
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 Unsaturated aliphatic monocarboxylic acid anion represented by
(R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3; 3 R ² and 2 × s R ³ each independently represent a hydrogen atom or a hydroxyl group And the total number of hydroxyl groups is 1 to 2.) saturated hydroxymonocarboxylic acid anion represented by
(8) The cation is a quaternary ammonium cation having one pentahydroxy-n-hexyl group and three 2,3-dihydroxy-n-propyl groups, and the anion is any of the following:
Saturated aliphatic monocarboxylic acid anion having a branched chain having 5 to 22 carbon atoms
R ¹ CH = CH (CH ₂ ) _r COO ⁻ (R ¹ is a hydrogen atom or CH ₃ (CH ₂ ) _q- (q is an integer of 0 to 7)), and r is an integer of 0 to 7 Unsaturated aliphatic monocarboxylic acid anion represented by
(R ² ) ₃ C (C (R ³ ) ₂ ) _s COO ⁻ (s represents an integer of 1 to 3; 3 R ² and 2 × s R ³ each independently represent a hydrogen atom or a hydroxyl group And the total number of hydroxyl groups is 1 to 2.) saturated hydroxymonocarboxylic acid anion represented by
HOOCC (R ⁴ R ⁵ ) C (R ⁶ R ⁷ ) C (R ⁸ R ⁹ ) COO ⁻ (R ^{4 to} R ⁹ each independently represent a hydrogen atom, a hydroxyl group or a carboxyl group, and the hydroxyl groups are a total of 1 to 2 The total number of carboxyl groups is 0 to 1.) Saturated hydroxydi or tricarboxylic acid anion having 6 to 20 carbon atoms, and 1 to 2 hydroxyaromatic monocarboxylic acid anions having hydroxyl groups
Alkyl ether carboxylic acid anion represented by CH ₃ (CH ₂ ) _v O (CH ₂ ) _w COO ⁻ (where v and w represent integers of 0 to 4) The proton is dissociated from trifluoroacetic acid or pentafluoropropionic acid Halogen carboxylic acid anion
(9) The cation has the following formula:
R ¹ is a linear or branched polyhydroxyalkyl group having 2 to 8 carbon atoms having two or more hydroxyl groups, and an ammonium cation in which R ² is a hydrogen atom and n is 1 to 4 The anion is a lactate anion.   A solvent for dissolving or dispersing a hydrogen bonding material, comprising the hydrophilic room temperature ionic liquid according to claim 1.   A solvent for dissolving or dispersing a hydrogen bonding organic compound material, comprising the hydrophilic room temperature ionic liquid according to claim 1.   A solvent for dissolving or dispersing a hydrogen bonding inorganic compound material comprising the hydrophilic room temperature ionic liquid according to claim 1.   A protein dissolving solvent comprising the hydrophilic room temperature ionic liquid according to claim 1.   A nucleic acid dissolving solvent comprising the hydrophilic room temperature ionic liquid according to claim 1.   A protein refolding agent comprising the hydrophilic room temperature ionic liquid according to claim 1.   A heat transfer medium comprising the hydrophilic room temperature ionic liquid according to claim 1.