Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
  • A61K31/365—Lactones
  • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
  • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
  • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
  • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
  • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/41—Amines
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
  • A61K8/73—Polysaccharides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P17/00—Drugs for dermatological disorders
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
  • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
  • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
  • C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
  • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
  • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
  • C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
  • C07C59/08—Lactic acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/235—Saturated compounds containing more than one carboxyl group
  • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
  • C07C59/255—Tartaric acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C59/235—Saturated compounds containing more than one carboxyl group
  • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
  • C07C59/265—Citric acid
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/10—Esters; Ether-esters
  • C08K5/101—Esters; Ether-esters of monocarboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L101/00—Compositions of unspecified macromolecular compounds
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  • C09K3/00—Materials not provided for elsewhere

Definitions

• the present invention relates to compositions suitable for gel-forming or thickening properties.
• Gels are used in biomedical fields such as cosmetics, conductive materials, thickeners, biomaterials, medical sensors, drug delivery systems, and cell culture substrates, and are expected to further improve their functionality.
• Conventional gels include a gel composed of 1-butyl-3-methylimidazolium chloride, xanthan gum, and water (Patent Document 1), a gel using gelatin (Patent Document 2), polyacrylic acid, glycerin, and water.
• Patent Document 3 A gel (Patent Document 3) and the like consisting of
• a gel using a polysaccharide and an ammonium salt such as that disclosed in Patent Document 1
• a gel using a polysaccharide and an ammonium salt can be easily and inexpensively produced as a stable hydrogel without washing with an organic solvent or the like.
• compositions suitable for gel forming or thickening properties with improved usability in practical use.
• Gels are expected to be applied to materials such as biomaterials, cosmetics, conductive materials, medical sensors, drug delivery systems, cell culture substrates, etc. in the field of living organisms. In the field of industrial materials, it is expected to be applied to materials such as industrial sensors, adhesives, thickeners, electrodes, and conductive materials.
• composition of the present invention contains the following components (A) and (B), a polymer compound and water as additive components, At least one of component (A) and component (B) has a hydrogen-bonding functional group.
• composition of the present invention contains water, a polymer compound, and at least one of component (A) and component (B) having a hydrogen-bonding functional group, and is excellent in gel-forming or thickening properties, water retention, It has excellent electrical conductivity, stabilizing effect on biomaterials including enzymes, solubility and release of active ingredients, and thixotropy.
• composition of the present invention comprises water, a polymer compound, and the components (A) and (B), wherein at least one of component (A) and component (B) has a hydrogen-bonding functional group. have.
• the skeleton of the amine compound of component (A) is not particularly limited. , oxazoline, thiazoline, morpholine, guanidine, pyrimidine, piperazine, triazine, quinoline, indole, quinoxaline, isoxazoline, and other cyclic amines and various amino acids, among which amines and amino acids are preferred. In addition, these may contain substituents described in the section [Substituents] below.
• amino acids examples include, but are not limited to, glycine, alanine, glutamic acid, arginine, asparagine, aspartic acid, isoleucine, glutamine, histidine, cysteine, leucine, lysine, proline, phenylalanine, threonine, serine, tryptophan, tyrosine, and methionine.
• valine valine, sarcosine, aminobutyric acid, methylleucine, aminocaprylic acid, aminohexanoic acid, aminocapric acid, aminolauric acid, aminomyristic acid, aminopalmitic acid, aminostearic acid, norvaline, aminovaleric acid, aminoisobutyric acid, thyroxine, Creatine, ornithine, opine, theanine, tricolamine, kainate, domoic acid, ibotenic acid, acromelic acid, cystine, hydroxyproline, hydroxylysine, thyroxine, phosphoserine, desmosine, beta-alanine, citrulline, creatine, trimethylglycine, cystathionine, methylhistidine , anserine, carnosine, aminoadipic acid, omitin and the like.
• the ammonium compounds include salts of the above amine compounds and quaternary amine compounds.
• Component (A) preferably has a hydrogen-bonding functional group.
• the hydrogen-bonding functional group in component (A) is not particularly limited, but examples thereof include oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, hydrogen atoms directly bonded to nitrogen, and the like.
• oxygen-containing groups include, but are not limited to, hydroxyl groups, carbonyl groups, ether groups, ester groups, aldehyde groups, carboxyl groups, carboxylate groups, urea groups, urethane groups, amide groups, oxazole groups, morpholine groups, carbamine groups.
• An acid group, a carbamate group, and the like can be mentioned. Among these, a hydroxyl group and a carboxy group are preferred, and a hydroxyl group is more preferred.
• the nitrogen-containing group is not particularly limited, but includes, for example, an amino group, a nitro group, and the like.
• Hydrogen-bonding functional groups in component (A) include hydroxyl, carboxy, carboxylate, ester, ether, and alkoxy groups from the viewpoint of affinity for coordination and bonding to water and polymer compounds. , hydrogen atoms directly bonded to nitrogen are preferred. Among these, a hydroxyl group, a carboxy group, a carboxylate group, an ether group, an alkoxy group, and a hydrogen atom directly bonded to nitrogen are more preferable, and a hydroxyl group, a carboxy group, a carboxylate group, and a hydrogen atom directly bonded to nitrogen are more preferable.
• a hydrogen atom directly bonded to a hydroxyl group, a carboxy group, or nitrogen is particularly preferred, and a hydrogen atom directly bonded to a hydroxyl group or nitrogen is most preferred.
• a preferred example of the substituent having a hydrogen-bonding functional group is a hydrocarbon group having a hydrogen-bonding functional group.
• substituents having a hydrogen-bonding functional group include a hydrocarbon group containing a hydroxy group (hydroxy hydrocarbon group), a hydrocarbon group containing a carboxy group (carboxy hydrocarbon group), and a hydrocarbon group containing a hydroxy group and a carboxy group.
• Examples include a hydrogen group (hydroxycarboxy hydrocarbon group), a hydrocarbon group containing a carboxylate group, a hydrocarbon group containing an ester group, a hydrocarbon group containing an ether group, a hydrocarbon group containing an alkoxy group, and the like. Among these, a hydroxy hydrocarbon group is preferred.
• the hydrocarbon group includes a saturated or unsaturated aliphatic hydrocarbon group, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, etc., and a hydrocarbon group combining them. Common hydrocarbon groups can be used as these hydrocarbon groups. Among the above hydrocarbon groups, saturated aliphatic hydrocarbon groups are preferred. Examples of the hydrocarbon group include those described in the section [Hydrocarbon group] below.
• the hydroxy hydrocarbon group has one or more hydroxyl groups, and the hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 12 carbon atoms. 1 to 6 linear or branched chains, and the hydrocarbon moiety may contain an oxygen atom.
• the carboxy hydrocarbon group has one or more carboxy groups, and the hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, particularly preferably carbon atoms. It is linear or branched with numbers 1 to 6, and the hydrocarbon portion may contain an oxygen atom.
• the hydroxycarboxy hydrocarbon group has one or more hydroxyl groups and one or more carboxy groups, and the hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, It is particularly preferably linear or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon group containing the carboxylate group has one or more carboxylate groups, and each hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, and still more preferably 1 to 1 carbon atoms. 12, particularly preferably straight or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon group containing an ester group has one or more ester groups, and each hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, It is particularly preferably linear or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon group containing an ether group has one or more ether groups, and each hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, It is particularly preferably linear or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon group containing the above alkoxy group has one or more alkoxy groups, and each hydrocarbon moiety preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, It is particularly preferably linear or branched having 1 to 6 carbon atoms, and the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon portion contains an oxygen atom
• the oxygen atom forms, for example, an ether bond, a carbonyl group, an ester bond, an amide bond, a urea bond, or a urethane bond with the hydrocarbon portion.
• the hydrocarbon moiety contains an oxygen atom means that the hydrocarbon moiety is interrupted by a group that may also contain a heteroatom such as a nitrogen atom as an atomic group containing an oxygen atom, or the group is Including at the ends or when a hydrogen atom is substituted in the group.
• hydroxy hydrocarbon group a saturated or unsaturated aliphatic hydrocarbon group having one or more hydroxy groups, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a hydrocarbon combination thereof groups.
• the number of hydroxyl groups in the hydroxy hydrocarbon group is preferably 2 or more, more preferably 3 or more.
• a hydroxy saturated aliphatic hydrocarbon group is preferable, a saturated aliphatic hydrocarbon group having one hydroxy group (monohydroxyalkyl group, etc.), a saturated aliphatic hydrocarbon group having two or more hydroxy groups (polyhydroxyalkyl group, etc.) ), a saturated aliphatic hydrocarbon group having 3 or more hydroxy groups (polyhydroxyalkyl group, etc.) is preferable, a saturated aliphatic hydrocarbon group having 2 or more hydroxy groups (polyhydroxyalkyl group, etc.), 3 hydroxy groups more preferably saturated aliphatic hydrocarbon groups having 3 or more hydroxy groups (polyhydroxyalkyl groups, etc.), more preferably saturated aliphatic hydrocarbon groups having 3 or more hydroxy groups (polyhydroxyalkyl groups, etc.), these are hydrocarbon moieties may contain the above oxygen-containing groups.
• the saturated aliphatic hydrocarbon group having one hydroxy group is not particularly limited, and examples thereof include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropane- 1-yl group, 2-hydroxypropan-1-yl group, 3-hydroxypropan-1-yl group, 1-hydroxypropan-2-yl group, 2-hydroxypropan-2-yl group, 2-hydroxymethylpropane -2-yl group, 2-hydroxyethylpropan-2-yl group, 1-hydroxybutan-1-yl group, 2-hydroxybutan-1-yl group, 3-hydroxybutan-1-yl group, 4-hydroxy butan-1-yl group, 1-hydroxy-2-methylpropan-1-yl group, 2-hydroxy-2-methylpropan-1-yl group, 3-hydroxy-2-methylpropan-1-yl group, 1 -hydroxybutan-2-yl group, 2-hydroxybutan-2-yl group, 3-hydroxybutan-2-yl group, 4-hydroxy
• the saturated aliphatic hydrocarbon group having two or more hydroxy groups is not particularly limited, and examples thereof include di-, tri-, tetra-, penta-, hexa-, hepta-, and octahydroxyalkyl groups. be done.
• dihydroxyethyl groups such as 1,2-dihydroxyethyl group; 1,2-dihydroxypropan-1-yl group, 2,3-dihydroxypropan-1-yl group dihydroxypropan-1-yl group; 1,2-dihydroxypropan-2-yl group, dihydroxypropan-2-yl group such as 1,3-dihydroxypropan-2-yl group; trihydroxypropan-1-yl group; trihydroxypropan-2-yl group; trihydroxypropan-1-yl group; trihydroxypropan-1-yl group; trihydroxypropan-2-yl group; 1,2-dihydroxybutan-1-yl group, 1,3-dihydroxybutan-1-yl group , 1,4-dihydroxybutan-1-yl group, 2,3-dihydroxybutan-1-yl group, 2,4-dihydroxybutan-1-yl group, 3,4-dihydroxybutan-1-yl group, etc.
• dihydroxyethyl groups such as 1,2-dihydroxyethyl group; 1,2-
• dihydroxybutan-1-yl group 1,2,3 trihydroxybutan-1-yl group, 1,2,4 trihydroxybutan-1-yl group, 1,3,4 trihydroxybutan-1-yl group, trihydroxybutan-1-yl group such as 2,3,4 trihydroxybutan-1-yl group; tetrahydroxybutan-1-yl group; 1,2-dihydroxy-2-methylpropan-1-yl group, 1 , 3-dihydroxy-2-methylpropan-1-yl group, dihydroxy-2-methylpropan-1-yl group such as 2,3-dihydroxy-2-methylpropan-1-yl group; trihydroxy-2-methyl Propan-1-yl group; Tetrahydroxy-2-methylpropan-1-yl group; 1,2-dihydroxybutan-2-yl group, 1,3-dihydroxybutan-2-yl group, 1,4-dihydroxybutane -2-yl group, 2,3-dihydroxybutan-2-yl group, 2,4-dihydroxybutan-2-yl group, 3,4-dihydroxy
• the polyhydroxy saturated aliphatic hydrocarbon group preferably has 2 to 8 hydroxyl groups, more preferably 2 to 6 hydroxyl groups.
• the alkyl group preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, and 1 to 6 carbon atoms. is particularly preferred.
• a branched polyhydroxy saturated aliphatic hydrocarbon group represented by the following formula is exemplified as a preferable one.
• R 7 is a hydrogen atom, a linear alkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms), or a linear alkyl group having 1 to 8 carbon atoms (preferably 1 to 4 carbon atoms) indicates a hydroxyalkyl group.
• the group of the above formula is not particularly limited, but examples include 1,2-dihydroxypropan-1-yl group, 2,3-dihydroxypropan-1-yl group, 1,2-dihydroxypropan-2-yl group, 1,3-dihydroxypropan-2-yl group, trihydroxypropan-1-yl group, trihydroxypropan-2-yl group, trihydroxypropan-1-yl group, trihydroxypropan-2-yl group, 1, 2-dihydroxybutan-1-yl group, 1,3-dihydroxybutan-1-yl group, 1,4-dihydroxybutan-1-yl group, 2,3-dihydroxybutan-1-yl group, 2,4- Dihydroxybutan-1-yl group, 3,4-dihydroxybutan-1-yl group, 1,2,3-trihydroxybutan-1-yl group, 1,2,4-trihydroxybutan-1-yl group 1,3 ,4-trihydroxybutan-1-yl group, 2,3,4-trihydroxybutan-1-yl group, tetrahydroxybutan
• 2,3-dihydroxypropan-1-yl group, 1,3-dihydroxypropan-2-yl group, 1,3-dihydroxy-2-ethylpropane-2- yl group, 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group, and pentahydroxyhexan-1-yl group are preferred, and 1,3-dihydroxy-2-hydroxymethylpropan-2-yl group is more preferred.
• a saturated or unsaturated aliphatic hydrocarbon group having one or more carboxy groups, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a hydrocarbon combination thereof groups.
• a monocarboxyalkyl group and a polycarboxyalkyl group, in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferred, and specific examples thereof include the mono-, di-, tri-, Examples thereof include tetra-, penta-, hexa-, hepta- or octahydroxyalkyl groups in which the hydroxyl group is substituted with a carboxy group (the alkyl moiety may contain an oxygen atom).
• Monocarboxy saturated aliphatic hydrocarbon groups and polycarboxy saturated aliphatic hydrocarbon groups preferably have 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, and even more preferably 1 to 12 carbon atoms. , and those having 1 to 6 carbon atoms are particularly preferred.
• the hydroxycarboxy hydrocarbon group includes saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups each having one or more hydroxy groups and one or more carboxyl groups, and also and a hydrocarbon group in which Among them, those in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferable, and are not particularly limited. Examples thereof include alkyl groups in which a portion of the hydroxyl group is substituted with a carboxy group (the alkyl moiety may contain an oxygen atom).
• the hydroxycarboxy saturated aliphatic hydrocarbon group preferably has 1 to 22 carbon atoms, more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, and 1 to 6 carbon atoms. Especially preferred.
• hydrocarbon group containing an ester group examples include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups having one or more ester groups, and combinations thereof. and hydrocarbon groups. Among them, those in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferred, and are not particularly limited. is mentioned.
• a hydrocarbon group containing an ester group preferably has 1 to 22 carbon atoms.
• the hydrocarbon group containing an ether group includes a saturated or unsaturated aliphatic hydrocarbon group having one or more ether groups, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a combination thereof. and hydrocarbon groups.
• hydrocarbon groups those in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferred and not particularly limited, but examples thereof include those in which an alkyl group having 2 to 22 carbon atoms is interrupted by an oxygen atom. .
• the hydrocarbon group containing the alkoxy group includes a saturated or unsaturated aliphatic hydrocarbon group having one or more alkoxy groups, a saturated or unsaturated alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a combination thereof. and hydrocarbon groups.
• hydrocarbon groups those in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferable and not particularly limited, but an alkyl ether group is bonded to the base end of an alkyl group having a total of 1 to 22 carbon atoms, or Examples thereof include those in which hydrogen atoms of hydrocarbon groups are substituted with alkyl ether groups.
• hydrocarbon group containing a carboxylate group examples include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, and aromatic hydrocarbon groups having one or more carboxylate groups. and a hydrocarbon group in which Among them, those in which the hydrocarbon group is a saturated aliphatic hydrocarbon group (such as an alkyl group) are preferred, and are not particularly limited. Examples include those in which a hydrogen atom of a hydrocarbon group is substituted with a carboxylate group.
• substituents other than hydrogen-bonding functional groups in component (A) and cations derived from component (A) include organic groups.
• the organic group essentially has a carbon atom and may additionally contain at least one selected from a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a halogen atom.
• the atomic group contained in the organic group is not particularly limited, examples thereof include hydrocarbon groups, heterocyclic groups, and substituents described in the section [Substituents] below.
• the substituents described in the "Substituents" column below replace the hydrogen atoms of the hydrocarbon group, interrupt the hydrocarbon group, are included at the base end of the hydrocarbon group, or are combined with the aromatic hydrocarbon group.
• Groups forming condensed rings are also included.
• the number of carbon atoms in the organic group is not particularly limited, it is preferably 1 to 8, more preferably 1 to 6, and even more preferably 1 to 4 in terms of affinity with water and polymer compounds.
• the hydrocarbon group is not particularly limited, and examples include saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof.
• a hydrocarbon group etc. are mentioned.
• it may be monovalent or polyvalent, and examples of monovalent saturated or unsaturated aliphatic hydrocarbon groups include, but are not limited to, linear or branched alkyl groups, alkenyl groups and alkynyl groups. etc.
• Alkyl groups include linear or branched chains, but are not particularly limited.
• Alkenyl groups include linear or branched chains, and are not particularly limited, but examples include vinyl, prop-1-en-1-yl, allyl, isopropenyl, but-1-en-1-yl. group, but-2-en-1-yl group, but-3-en-1-yl group, 2-methylprop-2-en-1-yl group, 1-methylprop-2-en-1-yl group, pent-1-en-1-yl group, pent-2-en-1-yl group, pent-3-en-1-yl group, pent-4-en-1-yl group, 3-methylbut-2- En-1-yl group, 3-methylbut-3-en-1-yl group, hex-1-en-1-yl group, hex-2-en-1-yl group, hex-3-en-1- yl group, hex-4-en-1-yl group, hex-5-en-1-yl group, 4-methylpent-3-en-1-yl group, 4-methylpent-3-en-1-yl group,
• Alkynyl groups include straight or branched chains, and are not particularly limited and include, but are not limited to, ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn- 1-yl group, but-3-yn-1-yl group, 1-methylprop-2-yn-1-yl group, pent-1-yn-1-yl group, pent-4-yn-1-yl group , hex-1-yn-1-yl group, hex-5-yn-1-yl group, hept-1-yn-1-yl group, hept-6-yn-1-yl group, octa-1-yne -1-yl group, octa-7-yn-1-yl group, non-1-yn-1-yl group, non-8-yn-1-yl group, deca-1-yn-1-yl group, Dec-9-yn-1-yl group, undec-1-yn-1-y
• the saturated or unsaturated alicyclic hydrocarbon group is preferably a saturated alicyclic hydrocarbon group and is not particularly limited.
• monovalent groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo A heptyl group, a cyclooctyl group, and a group containing an alicyclic residue such as those residues are included.
• the aromatic hydrocarbon group is not particularly limited, but includes, for example, a phenyl group, a naphthalene group, an anthracene group, and groups containing aromatic ring residues such as residues thereof.
• a condensed ring may be formed together with the substituents described in [Substituent] below.
• Examples of monovalent aromatic hydrocarbon groups include, but are not limited to, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5 -dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,5-trimethylphenyl group, 2,4,6-trimethylphenyl group, 4-ethylphenyl group, 4-propyl phenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-tert-butylphenyl group, 4-pentylphenyl group, 4-tert-pentylphenyl group, 2,4-bis(4-tert-pentyl)phenyl group, 1,1,3,3-tetramethylbutylphenyl group, 2-methyl-5-tert-butylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 4-hepty
• divalent hydrocarbon groups examples include groups obtained by removing one hydrogen atom from the above groups.
• substituents examples include, but are not limited to, hydrocarbon groups, oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and halogens. Substituents also include groups to which these substituents are bonded.
• hydrocarbon group examples include those listed in the above [hydrocarbon group].
• oxygen-containing groups include, but are not limited to, hydroxyl groups, alkoxy groups, acetoxy groups, acetyl groups, aldehyde groups, carboxyl groups, carboxylate groups, urea groups, urethane groups, amide groups, imide groups, ether groups, carbonyl group, ester group, oxazole group, morpholine group, carbamate group, carbamoyl group, polyoxyethylene group, tocopheryl group, chroman group, dihydropyran group, glyceryl group, glyceryl ether group and the like.
• nitrogen-containing groups include, but are not limited to, cyano groups, cyanato groups, isocyanate groups, nitro groups, nitroalkyl groups, amide groups, urea groups, urethane groups, imide groups, carbodiimide groups, azo groups, pyridine groups, imidazole group, primary amino group, secondary amino group, tertiary amino group, quaternary ammonium group, aminoalkyl group and the like.
• sulfur-containing groups include, but are not limited to, sulfuric acid group, sulfonyl group, sulfonic acid group, mercapto group, thioether group, thiocarbonyl group, thiourea group, thiocarboxy group, thiocarboxylate group, dithiocarboxy group, Dithiocarboxylate group, sulfate ester, thiophene group, thiazole group, thiol group, sulfo group, sulfide group, disulfide group, thioester group, thioamide group, thiocarbamate group, dithiocarbamate group and esters thereof.
• Examples of phosphorus-containing groups include, but are not limited to, phosphoric acid group, phosphorous acid group, phosphonic acid group, phosphinic acid group, phosphonous acid group, phosphinic acid group, pyrophosphate group, phosphate ester group, Phosphate ester group, phosphonate ester group, pyrophosphate group, ester group thereof and the like.
• Halogen includes fluorine, chlorine, bromine, and iodine.
• Examples of the organic group include hydrocarbon groups that may have a substituent and whose hydrocarbon portion may contain an oxygen atom.
• hydrocarbon group the contents described in the above [Hydrocarbon group] column are referred to.
• the hydrocarbon group is preferably an aliphatic hydrocarbon group, more preferably a saturated aliphatic hydrocarbon group (such as an alkyl group).
• the saturated aliphatic hydrocarbon group preferably has 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms, from the viewpoint of affinity with water.
• the hydrocarbon group may have a substituent, and the substituent is not particularly limited, but includes, for example, those described in the above [Substituent] column.
• substituents those having an oxygen-containing group are preferred, and among these, a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, an ether group, and an alkoxy group are preferred.
• hydroxyl group, carboxy group, carboxylate group, ether group, and alkoxy group are more preferable, hydroxyl group, carboxy group, and carboxylate group are more preferable, hydroxyl group and carboxylate group are particularly preferable, and hydroxyl group is particularly preferable.
• the hydrocarbon moiety may contain an oxygen atom.
• the hydrocarbon moiety contains the oxygen-containing group described above, for example, an ether bond, a carbonyl group, a hydroxyl group, a carboxylate group, an ester bond, an amide bond, a urea Forms or contains a bond or a urethane bond. Therefore, in the present invention, "the hydrocarbon moiety contains an oxygen atom” means that the hydrocarbon moiety is interrupted by a group that may also contain a heteroatom such as a nitrogen atom as an atomic group containing an oxygen atom, or the group is Including at the ends or when a hydrogen atom is substituted in the group.
• Component (A) has at least one hydrogen-bonding functional group (hydroxyl and carboxy It is one of preferred embodiments to have a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) having a hydroxyl group is more preferable).
• one or more of the moieties (atoms contained in the basic skeleton chemical structure, such as nitrogen moieties and carbon moieties that form a ring together with nitrogen) to which functional groups can be introduced in component (A) are hydrogen It is preferably substituted with a hydrocarbon group having a bonding functional group, and if there are other sites, they are each independently a hydrogen atom or a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group). preferably substituted with an organic group such as a hydrogen group). It is also preferred that the site is composed only of hydrogen atoms directly bonded to nitrogen.
• the amine of component (A) is an amine composed only of a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) having a hydrogen-bonding functional group and a hydrogen atom directly bonded to nitrogen; Hydrocarbon groups having hydrogen-bonding functional groups (more preferably saturated aliphatic hydrocarbon groups) and amines composed only of hydrocarbon groups (more preferably saturated aliphatic hydrocarbon groups), having hydrogen-bonding functional groups Amines composed only of hydrocarbon groups (more preferably saturated aliphatic hydrocarbon groups), amines composed only of hydrogen atoms are preferred, and hydrocarbon groups having hydrogen-bonding functional groups (more preferably saturated aliphatic hydrocarbon groups) are preferred.
• Hydrogen groups (more preferably saturated aliphatic hydrocarbon groups) and amines composed only of hydrogen atoms directly bonded to nitrogen, hydrocarbon groups having hydrogen-bonding functional groups (more preferably saturated aliphatic hydrocarbon groups) and An amine composed only of a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) is more preferable, and a hydrocarbon group having a hydrogen-bonding functional group (more preferably a saturated aliphatic hydrocarbon group) and a direct bond to nitrogen Amines composed only of hydrogen atoms are particularly preferred.
• the hydrogen-bonding functional group is preferably a hydroxyl group.
• the amine of component (A) has 3 hydroxyl groups.
• component (A) has a monohydroxyalkyl group
• triethanolamine and diethanolamine are preferred, and triethanolamine is particularly preferred.
• component (A) is specified in the Standards for Quasi-drug Ingredients (Quasi-drugs Ingredients), Standards for Quasi-drug Additives, Japanese Pharmacopoeia (Japanese Pharmacopoeia), Japanese Pharmacopoeia Drugs It is preferable to use compounds listed in the Standards for Quasi-Drugs (Regulations), Pharmaceutical Additives Standards (Medicine Additives), and Food Additives Standards (Food Additives) as raw materials (for example, acids and bases).
• Such compounds include, but are not limited to, monoethanolamine, diethanolamine, triethanolamine, 2-amino-2-hydroxymethyl-1,3-propanediol, 2-amino-2-methyl-1- Propanol, 2-amino-2-methyl-1,3-propanediol, monoisopropanolamine, diisopropanolamine, triisopropanolamine, 2-acetamidoethanolamine, N-lauryldiethanolamine, dimethyloctadecylamine are preferred, from the viewpoint of low odor.
• 2-amino-2-hydroxymethyl-1,3-propanediol 2-amino-2-methyl-1,3-propanediol are more preferable, and 2-amino-2-hydroxymethyl-1,3-propane Diols are more preferred.
• the cations derived from component (A) are preferably those in which a cationic residue such as a hydrogen atom is bound to the above amine compound. ) may be derived from
• the residue in the component (B) refers to an uncharged atom or atomic group (group), a cationic residue having a charge that becomes a cation, and an anionic residue that becomes an anion.
• the anion is not particularly limited, but examples include hydroxide anions, halogen anions, sulfur anions, phosphorus anions, cyanide anions, and boron anions. , fluorine-based anions, nitrogen oxide-based anions, carboxylic acid-based anions, and the like, and among these, hydroxide anions are preferred.
• component (A) is preferably an amine compound represented by the following formula (I).
• each R 1 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom.
• each R 2 is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms
• m represents an integer of 0 to 3.
• m is preferably an integer of 1-3.
• R 2 are preferably hydrogen atoms.
• R 1 is preferably a linear or branched hydroxy hydrocarbon group having 1 to 22 carbon atoms in the hydrocarbon moiety.
• the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon.
• At least one of R 1 preferably has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
• At least one of R 1 preferably has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
• At least one of R 1 has one or more hydroxyl groups
• the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms
• the hydrocarbon in the hydrocarbon moiety is a saturated aliphatic hydrocarbon. It is preferably a hydrogen hydroxy hydrocarbon group.
• R 1 is a hydroxyalkyl group having one or more hydroxyl groups, a branched hydrocarbon moiety having 3 to 6 carbon atoms, and the hydrocarbon moiety being an alkyl group; is a hydrogen atom and m is an integer of 1 in one preferred embodiment.
• R 1 is a hydroxyalkyl group having one hydroxyl group, a linear hydrocarbon moiety having 1 to 6 carbon atoms, the hydrocarbon moiety being an alkyl group, and m being an integer of 3. It is one of preferred embodiments.
• a combination of at least one of the above preferred examples shown in formula (I) can be a more preferred embodiment.
• component (A) is an ammonium compound
• said component (A) is preferably an ammonium compound represented by the following formula (II).
• each R 3 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom.
• each R 4 is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms
• n represents an integer of 0 to 4
• X ⁇ represents an anion.
• n is preferably an integer of 1-4.
• R 4 are preferably hydrogen atoms.
• R 3 is preferably a linear or branched hydroxy hydrocarbon group having 1 to 22 carbon atoms in the hydrocarbon moiety.
• the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon.
• At least one of R 3 preferably has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
• At least one of R 3 preferably has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
• At least one of R 3 has one or more hydroxyl groups
• the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms
• the hydrocarbon in the hydrocarbon moiety is a saturated aliphatic hydrocarbon. It is preferably a hydrogen hydroxy hydrocarbon group.
• the anion represented by X ⁇ is preferably a hydroxide ion.
• R 3 is a hydroxyalkyl group having one or more hydroxyl groups, a branched hydrocarbon moiety having 3 to 6 carbon atoms, and the hydrocarbon moiety being an alkyl group; is a hydrogen atom and n is an integer of 1 in one preferred embodiment.
• R 3 is a hydroxyalkyl group having one hydroxyl group, a straight-chain hydrocarbon moiety having 1 to 6 carbon atoms, the hydrocarbon moiety being an alkyl group, and n being an integer of 3. It is one of preferred embodiments.
• ammonium salt formed by component (A) and component (B) is also one preferred embodiment of the composition of the present invention.
• an ammonium salt formed by a cation derived from the component (A), which may have a cationic residue of the component (B), and an anion derived from the anionic residue of the component (B). contains.
• the residue in the component (B) refers to an uncharged atom or atomic group (group), a cationic residue having a charge that becomes a cation, and an anionic residue that becomes an anion.
• the acid of component (B) or a salt thereof has a cationic residue and an anionic residue.
• the cationic residue is a hydrogen atom or a group (atomic group) that combines with the nitrogen atom of component (A) to form a hydrogen-bonding functional group or an organic group.
• the acid of component (B) is a compound composed of protonated hydrogen and an anionic residue.
• the cation is preferably an ammonium cation.
• ammonium salts include organic cations or NH 4 + having a nitrogen atom as the ion center, and anions.
• organic cations and organic anions include organic cations and organic anions.
• organic is meant to include carbon and hydrogen as elements.
• the cations derived from the component (A) are not particularly limited, but examples include ammonium cations (NH 4 + , primary ammonium cations, secondary ammonium cations, tertiary ammonium cations), imidazolium cations, pyridinium cations, pyrrolidinium cations, cation, piperidinium cation, pyrrolinium cation, pyrazinium cation, triazolium cation, isoquinolinium cation, oxazolinium cation, thiazolinium cation, morpholinium cation, guanidinium cation, pyrimidinium cation cations derived from cyclic amines such as nium cations, piperazinium cations, triazinium cations, quinolinium cations, indolinium cations, quinoxalinium cations, isoxazolium cations, and cati
• ammonium cation imidazolium cation, pyridinium cation, pyrrolidinium cation, piperidinium cation, and morpholinium cation are preferred, and ammonium cation is more preferred.
• the cation of the ammonium salt formed by the component (A) and the component (B) is preferably a cation represented by the following formula (III). Moreover, when the component (A) is an ammonium compound, its cation is also preferably a cation represented by the following formula (III).
• each R 5 independently has one or more hydroxyl groups, the hydrocarbon moiety is linear or branched with 1 to 22 carbon atoms, and the hydrocarbon moiety contains an oxygen atom.
• each R 6 is independently a hydrogen atom or an organic group having 1 to 22 carbon atoms, and o represents an integer of 0 to 4.
• o is preferably an integer of 1-4.
• R 6 are preferably hydrogen atoms.
• R 5 is preferably a hydroxy hydrocarbon group.
• the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon.
• At least one of R 5 has one hydroxyl group, and the hydrocarbon in the hydrocarbon moiety is preferably a hydroxy hydrocarbon group of saturated aliphatic hydrocarbon.
• At least one of R 5 preferably has two or more hydroxyl groups, and the hydrocarbon in the hydrocarbon moiety is preferably a saturated aliphatic hydrocarbon hydroxy hydrocarbon group.
• At least one of R 5 has one or more hydroxyl groups
• the hydrocarbon moiety is a branched chain having 3 to 22 carbon atoms
• the hydrocarbon in the hydrocarbon moiety is a saturated aliphatic hydrocarbon. It is preferably a hydrogen hydroxy hydrocarbon group.
• R 6 of the cation represented by the formula (III) is a hydrogen atom
• the proton corresponding to the hydrogen atom is preferably derived from the component (B).
• R 5 is a hydroxyalkyl group having one or more hydroxyl groups, a branched hydrocarbon moiety having 3 to 6 carbon atoms, and the hydrocarbon moiety being an alkyl group; is a hydrogen atom and o is an integer of 1 in one preferred embodiment.
• R 5 is a hydroxyalkyl group having one hydroxyl group, a linear hydrocarbon moiety having 1 to 6 carbon atoms, the hydrocarbon moiety being an alkyl group, and o being an integer of 3. It is one of preferred embodiments.
• a combination of at least one of the above preferred examples shown in formula (III) can be a more preferred embodiment.
• the cation derived from component (A) (the cation of the ammonium compound of component (A)) has the effects of the present invention, namely gel formation, thickening effect, water retention, electrical conductivity, and stability to biomaterials such as enzymes. From the viewpoints of synergizing effect, solubility and releasability of active ingredients, and thixotropy, it is preferable to have a hydrocarbon group having one or more hydrogen-bonding functional groups (more preferably a saturated aliphatic hydrocarbon group). one of.
• the cation derived from the component (A) (the cation of the ammonium compound of the component (A)) into which a functional group can be introduced (such as a nitrogen site or a carbon site that forms a ring together with nitrogen) becomes a basic skeleton.
• atoms contained in the chemical structure one or more of which is preferably substituted with a hydrocarbon group having a hydrogen-bonding functional group. It is preferably present or substituted with an organic group such as a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group). It is also preferred that the site is composed only of hydrogen atoms directly bonded to nitrogen.
• the cation derived from component (A) is a hydrocarbon group having a hydrogen-bonding functional group (more preferably a saturated aliphatic hydrocarbon group) and nitrogen A cation composed only of hydrogen atoms directly bonded to, a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) having a hydrogen-bonding functional group, and a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) only A cation composed of, a cation composed only of a hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) having a hydrogen-bonding functional group, a cation composed only of hydrogen atoms is preferable, and a hydrogen-bonding functional group A hydrocarbon group (more preferably a saturated aliphatic hydrocarbon group) with a cation composed only of hydrogen atoms directly bonded to nitrogen, a hydrocarbon group with a hydrogen-bonding functional group (more
• the cation represented by the formula (III) is obtained by bonding a cationic residue such as a hydrogen atom to the amine of the component (A), and the cationic residue such as a hydrogen atom is derived from the component (B). is a preferred embodiment.
• the total carbon number of the hydrocarbon groups (such as alkyl groups) in component (A), formulas (I), (II), and (III) is 1 to 12. is preferred, 1 to 8 are more preferred, 1 to 6 are even more preferred, and 1 to 4 are particularly preferred.
• the acid of component (B) or a salt thereof has a cationic residue and an anionic residue.
• the cationic residue is a hydrogen atom or a group (atomic group) that combines with the nitrogen atom of component (A) to form a hydrogen-bonding functional group or an organic group.
• the hydrogen-bonding functional group in component (B) may be one possessed by an anionic residue, or may be hydrogen that becomes a proton in an acid.
• at least the anionic residue has a hydrogen-bonding functional group.
• the component (B) acid is a compound composed of protonated hydrogen and an anionic residue (e.g., the anion shown below), as well as a Lewis acid in a salt-forming reaction with component (A).
• Acid-acting compounds are not excluded, for example, halogenated hydrocarbons, dialkylsulfuric acids, dialkylcarbonates, alkylsulfonic acids, which may have the above substituents (preferably oxygen-containing groups) on the hydrocarbon moiety , phosphate alkyl esters, and the like.
• the acid of component (B) is a compound composed of protonated hydrogen and an anionic residue.
• the anion derived from the anionic residue of component (B) is not particularly limited, but examples include halogen anions, sulfur anions, phosphorus anions, cyanide anions, boron anions, fluorine anions, Nitrogen oxide-based anions, carboxylic acid-based anions, and the like are included. These may be used individually by 1 type, and may be used in combination of 2 or more type. Among these, halogen-based anions, sulfur-based anions, phosphorus-based anions, boron-based anions, fluorine-based anions, nitrogen oxide-based anions, and carboxylic acid-based anions are preferable. Acid anions are more preferred, and carboxylate anions are even more preferred.
• the anionic residue of component (B) preferably has a hydrogen-bonding functional group, and examples of the hydrogen-bonding functional group include the aforementioned hydrogen-bonding functional groups.
• a carboxylate group, an ether group and an alkoxy group are preferred, and a hydroxyl group is more preferred.
• halogen-based anions are not particularly limited, but include, for example, fluorine ions, chloride ions, bromide ions, iodine ions, fluorine-based anions, and the like.
• the sulfur-based anion is not particularly limited. p-toluenesulfonate anion, 2,4,6-trimethylbenzenesulfonate anion, styrenesulfonate anion, 3-sulfopropyl methacrylate anion, 3-sulfopropyl acrylate anion, etc.), sulfate anion, hydrogen sulfate anion, alkyl Sulfate anions (eg, methylsulfate anion, ethylsulfate anion, butylsulfate anion, octylsulfate anion, 2-(2-methoxyethoxy)ethylsulfate anion, etc.) and the like.
• alkyl Sulfate anions eg, methylsulfate anion, ethylsulfate anion, butylsulfate anion, octylsulfate anion, 2-(2-me
• Examples of the phosphorus-based anion include, but are not limited to, phosphate anion, hydrogen phosphate anion, dihydrogen phosphate anion, phosphonate anion, hydrogen phosphonate anion, dihydrogen phosphonate anion, phosphinate anion, hydrogen Phosphinate anions, alkyl phosphate anions (e.g. dimethyl phosphate anion, diethyl phosphate anion, dipropyl phosphate anion, dibutyl phosphate anion, etc.), alkyl phosphonate anions (e.g.
• methyl phosphonate anions ethyl phosphonate anions anion, propylphosphonate anion, butylphosphonate anion, methylmethylphosphonate anion, etc.
• alkylphosphinate anion hexaalkylphosphate anion and the like.
• the cyan anion is not particularly limited, but includes, for example, tetracyanoborate anion, dicyanamide anion, thiocyanate anion, isothiocyanate anion, and the like.
• the boron-based anion is not particularly limited, but includes, for example, a tetraalkylborate anion such as a tetrafluoroborate anion, a bisoxalateborate anion, and a tetraphenylborate anion.
• a tetraalkylborate anion such as a tetrafluoroborate anion, a bisoxalateborate anion, and a tetraphenylborate anion.
• the fluorine-based anion is not particularly limited. ) imide, bis(heptafluoropropanesulfonyl)imide anion, bis(nonafluorobutylsulfonyl)imide, etc.), perfluoroalkylsulfonate anion (e.g., trifluoromethanesulfonate anion, pentafluoroethanesulfonate anion, heptafluoropropanesulfonate phosphate anion, nonaflate anion, perfluorooctanesulfonate anion, etc.), fluorophosphate anion (e.g., hexafluorophosphate anion, tri(pentafluoroethyl)trifluorophosphate anion, etc.), tris (perfluoroalkylsulfonyl ) methide anion (e.g., tris(trifluoromethanesulfony
• the nitrogen oxide anion is not particularly limited, but includes, for example, nitrate anion and nitrite anion.
• the carboxylate anion is an organic acid anion having at least one carboxylate anion (—COO ⁇ ) in the molecule, and includes an oxygen-containing group, a nitrogen-containing group, a sulfur-containing group, a phosphorus-containing group, and a hydrocarbon. You may have a group or the like.
• Carboxylic acid anions include, but are not limited to, saturated or unsaturated aliphatic hydrocarbon groups, saturated or unsaturated alicyclic hydrocarbon groups, aromatic hydrocarbon groups, etc., and hydrocarbons combining them.
• Anions having a group and a carboxylate anion include, for example, saturated aliphatic carboxylate anions, unsaturated aliphatic carboxylate anions, saturated or unsaturated alicyclic carboxylate anions, aromatic carboxylate anions, saturated aliphatic hydroxy Carboxylate anion, unsaturated aliphatic hydroxycarboxylate anion, saturated or unsaturated alicyclic hydroxycarboxylate anion, aromatic hydroxycarboxylate anion, carbonylcarboxylate anion, alkyl ether carboxylate anion, halogen carboxylate anion, amino acid anion etc. (The number of carbon atoms in the carboxylate anions listed below includes the carbon atoms in the carboxy group.).
• the saturated aliphatic carboxylate anion consists of a linear or branched saturated aliphatic hydrocarbon group and one or more carboxylate anions, may contain a carboxy group or a carboxylate group, and has 1 to 22 carbon atoms. is preferred.
• formic acid acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecyl acid, palmitic acid , margaric acid, stearic acid, arachidic acid, henicosyl acid, behenic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, 2-ethylhexanoic acid, isononanoic acid, isopalmitic acid, isostearic acid, oxalic acid, malonic acid,
• Examples include anions obtained by dissociating protons from succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and the like.
• the unsaturated aliphatic carboxylate anion consists of a linear or branched unsaturated aliphatic hydrocarbon group and one or more carboxylate anions, may contain a carboxy group or a carboxylate group, and has 3 carbon atoms. ⁇ 22 is preferred. Specifically, but not limited to, acrylic acid, methacrylic acid, crotonic acid, palmitoleic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, eleostearic acid, arachidonic acid, maleic acid, fumaric acid, etc. Anions in which protons are dissociated from are exemplified.
• the saturated or unsaturated alicyclic carboxylate anion consists of a saturated or unsaturated carbocyclic ring having no aromaticity and one or more carboxylate anions, may contain a carboxy group or a carboxylate group, and has a carbon number of 6 to 20 are preferred.
• a saturated alicyclic carboxylic acid anion having a cyclohexane ring skeleton is preferable, and specific examples include, but are not particularly limited to, anions in which protons are dissociated from cyclohexanecarboxylic acid and cyclohexanedicarboxylic acid.
• the aromatic carboxylate anion consists of a single ring or a plurality of aromatic rings and one or more carboxylate anions, may contain a carboxy group or a carboxylate group, and preferably has 6 to 20 carbon atoms.
• aromatic carboxylate anions having a benzene ring skeleton are preferred, and specific examples thereof include, but are not limited to, anions in which protons are dissociated from benzoic acid, cinnamic acid, phthalic acid, isophthalic acid, terephthalic acid, and the like. be done.
• the saturated aliphatic hydroxycarboxylic acid anion consists of a linear or branched saturated aliphatic hydrocarbon group, one or more carboxylic acid anions and one or more hydroxyl groups, and may include a carboxy group and a carboxylate group. Well, preferably 2 to 24 carbon atoms. Among them, saturated aliphatic hydroxycarboxylic acid anions having 2 to 7 carbon atoms and 1 to 4 hydroxyl groups are preferred. Specific examples include, but are not limited to, glycolic acid, lactic acid, tartronic acid, glyceric acid, hydroxyacetic acid, hydroxybutyric acid, 2-hydroxydecanoic acid, 3-hydroxydecanoic acid, 12-hydroxystearic acid, and dihydroxystearic acid. , cerebronic acid, malic acid, tartaric acid, citramaric acid, citric acid, isocitric acid, leucic acid, mevalonic acid, pantoic acid, and the like.
• the unsaturated aliphatic hydroxycarboxylate anion consists of a linear or branched unsaturated aliphatic sum hydrocarbon group, one or more carboxylate anions and one or more hydroxyl groups, a carboxy group, a carboxylate group and preferably has 3 to 22 carbon atoms.
• Specific examples include, but are not particularly limited to, anions obtained by dissociating protons from ricinoleic acid, ricinoleic acid, ricineraidic acid, and the like.
• the saturated or unsaturated alicyclic hydroxycarboxylate anion is composed of a saturated or unsaturated carbocyclic ring having no aromaticity, one or more carboxylate anions and one or more hydroxyl groups, and includes a carboxy group, a carboxylate It may contain a group, and preferably has 4 to 20 carbon atoms.
• a saturated alicyclic hydroxycarboxylic acid anion having a 6-membered ring skeleton having 1 to 4 hydroxyl groups is preferable.
• examples include hydroxycyclohexanecarboxylic acid, dihydroxycyclohexanecarboxylic acid, and quinic acid.
• the aromatic hydroxycarboxylic acid anion consists of a single ring or a plurality of rings having aromaticity, one or more carboxylic acid anions and one or more hydroxyl groups, and may contain a carboxy group and a carboxylate group. 6 to 20 are preferred.
• an aromatic carboxylic acid anion having a benzene ring skeleton having 1 to 3 hydroxyl groups is preferable, and specific examples thereof include, but are not limited to, salicylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxy Protons are released from methylbenzoic acid, vanillic acid, syringic acid, pyrotocatechuic acid, gentisic acid, orceric acid, mandelic acid, benzilic acid, atrolactinic acid, phloretic acid, coumaric acid, umberic acid, caffeic acid, ferulic acid, sinapic acid, etc. Dissociated anions are included.
• the carbonyl carboxylate anion is a carboxylate anion having 3 to 22 carbon atoms having a carbonyl group in the molecule, may contain a carboxy group and a carboxylate group, and has 1 to 2 carbonyl groups and has 3 to 2 carbon atoms.
• a carbonyl carboxylate anion of 7 is preferred.
• a carbonyl carboxylate anion represented by CH 3 ((CH 2 ) p CO(CH 2 ) q )COO - (p and q are integers of 0 to 2) is preferred. Specific examples thereof include, but are not particularly limited to, anions in which protons are dissociated from pyruvic acid or the like.
• the alkyl ether carboxylate anion is a carboxylate anion having 2 to 22 carbon atoms having an ether group in the molecule, including a polyoxyalkylene alkyl ether carboxylate anion, and may contain a carboxy group and a carboxylate group.
• C2-C12 alkyl carboxylate anions with ⁇ 2 ether groups are preferred, especially CH3 ( CH2 ) rO ( CH2 ) sCOO- ( r and s are integers from 0 to 4 ), and more preferably polyoxyethylene alkyl ether carboxylate anions.
• Alkyl ether carboxylate anions are not particularly limited, but include, for example, anions in which protons are dissociated from methoxyacetic acid, ethoxyacetic acid, methoxybutyric acid, ethoxybutyric acid, and the like.
• the halogen carboxylate anion is a carboxylate anion having 2 to 22 carbon atoms having a halogen atom in the molecule, and may contain a carboxy group or a carboxylate group, preferably a halogen carboxylate anion having 2 to 22 carbon atoms.
• a carboxylate anion having 2 to 22 carbon atoms preferably a halogen carboxylate anion having 2 to 22 carbon atoms.
• the amino acid anion is a carboxylate anion having 2 to 22 carbon atoms and having an amino group in the molecule, and may contain a carboxy group or a carboxylate group.
• Amino acid anions are preferred. Specifically, but not limited to, for example, glycine, alanine, glutamic acid, arginine, asparagine, aspartic acid, isoleucine, glutamine, histidine, cysteine, leucine, lysine, proline, phenylalanine, threonine, serine, tryptophan, tyrosine, methionine , valine, sarcosine, aminobutyric acid, methylleucine, aminocaprylic acid, aminohexanoic acid, aminocapric acid, aminolauric acid, aminomyristic acid, aminopalmitic acid, aminostearic acid, norvaline, aminovaleric acid, aminoisobutyric acid, thyroxine, Creatine,
• Salts of component (B) include salts of the above anions and cations (alkali metal cations, alkaline earth metal cations, ammonium cations, etc.).
• the amine or ammonium compound as component (A), the acid or its salt as component (B), and the ammonium salt formed by component (A) and component (B) may be used singly. More than one species may be used in combination.
• component (B) is a polybasic acid
• component (A) and component (B) may be blended so that the valence of component (A) is equivalent to that of component (B).
• the composition may be less than equivalent, or more than equivalent (when component (B) is a polybasic acid, it may be a partially neutralized salt or a completely neutralized salt).
• component (B) is a dibasic acid and component (A) has a valence of 1, the blending molar ratio of component (A) and component (B) should be 1:1 mol to 2:1 mol. can be done.
• Two or more kinds of components (A) may be used.
• component (A) has hydrogen-bonding functional groups, the effects of those hydrogen-bonding functional groups can be enhanced.
• component (A) and component (B) form an ammonium salt, two molecules of cations derived from component (A) can be introduced into one molecule of salt. The effect of the functional group can be further enhanced.
• component (A) and component (B) In order to improve gel formability, thickening effect, water retention, electrical conductivity, stabilizing effect on biomaterials such as enzymes, solubility and release of active ingredients, and thixotropy, component (A) and In the case of a mixture of component (B) or a salt of component (A) and component (B), either the cation or the anion of the salt of component (A) and component (B) or component (A) and component (B) One of them preferably has a hydrogen-bonding functional group, and both preferably have a hydrogen-bonding functional group.
• hydrogen-bonding functional groups for component (A) are those listed above, and hydrogen-bonding functional groups for component (B) include oxygen-containing groups, nitrogen-containing groups, sulfur-containing groups, phosphorus-containing groups, and the like. mentioned.
• element-containing groups a hydroxyl group, a carboxy group, a carboxylate group, an ester group, an ether group, an alkoxy group, a carbonyl group, an amino group, a sulfonyl group, a sulfate ester group, a phosphate group, and a phosphate ester group are preferred.
• a hydroxyl group preferably a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, an ether group, an alkoxy group, or a carbonyl group, more preferably a hydroxyl group, a carboxyl group, a carboxylate group, an ester group, an ether group, or an alkoxy group, and particularly preferably a hydroxyl group .
• composition of the present invention has a hydrogen-bonding functional group in at least one of component (A) and component (B), and it is one of preferred embodiments that this hydrogen-bonding functional group is a hydroxyl group.
• component (B) may be Compounds listed in the Pharmacopoeial Standards for Quasi-Drugs (Regulations), Pharmaceutical Additives Standards (Medicine Additives), and Food Additives Standards (Food Additives) are preferably used as raw materials, but are not particularly limited.
• acetic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, lactic acid, glycolic acid, succinic acid, citric acid, hydrochloric acid, fumaric acid, phosphoric acid, ascorbic acid, etc. is mentioned.
• Amino acids that can be used for component (A) and component (B) include glycine, alanine, arginine, aspartic acid, histidine, cysteine, proline, serine, tryptophan, tyrosine, methionine, aminobutyric acid, aminohexanoic acid, Cystine, glutamic acid, isoleucine, phenylalanine, threonine, tryptophan, methionine, valine, theanine and the like.
• composition of the present invention provides gel formability, thickening properties, water retention, electrical conductivity, stabilizing effect on biomaterials such as enzymes, solubility and release of active ingredients, and thixotropy.
• the mixture of component (A) and component (B) or the salt of component (A) and component (B) may be in an anhydrous state (anhydrous), and the moisture in the air may be It may be an absorbed hydrate.
• a hydrate refers to a compound that, when left in the air at 25°C, absorbs water and has a saturated moisture content. Compounds that do not absorb water when left in air at 25° C. are non-hydrated and anhydrous.
• the mixture of components (A) and (B) or the salt of (A) and (B) is an anhydride and/or hydrate that is liquid or solid at 25°C.
• it is preferably liquid at 25 ° C.
• the freezing point of the anhydride and / or hydrate is preferably less than 25 ° C., more preferably less than -5 ° C. It is preferred, and less than -10°C is more preferred.
• the composition of the present invention is mainly intended for a composition that is blended in an arbitrary step when manufacturing a desired composition.
• the composition of the present invention contains components (A) and (B), a polymer compound and water.
• “adding" components (A), (B), a polymer compound, and water means that components (A), (B), a polymer compound, and water are added until the final composition is prepared.
• Salts or salts formed with components (A), (B) or components (A), (B) or components (A), (B) and water using these and water as starting materials It includes the case where an aqueous solution is synthesized and the salt or salt solution is used as an additive, and the case where the salt or salt solution is optionally mixed with water and/or components such as a polymer compound to form a composition.
• the composition of the present invention may be a mixture (including a salt thereof) consisting only of components (A), (B), a polymer compound and water, and (A), (B) ( Alternatively, it may be a composition containing components other than (A) and (B)), a polymer compound and water.
• the composition of the present invention also primarily targets the desired final composition.
• the composition of the present invention includes the final composition produced by adding the component (A), the component (B), the polymer compound and water in any step thereof, and only using the composition of the present invention Instead, it may contain components (A), (B), a polymer compound, and water.
• the gel composition of the present invention is a gel-like composition among the compositions suitable for the above gel-forming or thickening properties.
• the thickened or to-be-thickened compositions of the present invention contain, among other compositions suitable for gel-forming or thickening properties as described above, components (A), (B) and polymeric compounds. Thickening is caused by the action of the component (A), the component (B), and the polymer compound added when preparing the composition thickened by the action or the intended thickened composition. possible compositions.
• the component (A), the component (B), the polymer compound and water it is preferable to heat and dissolve the component (A), the component (B), the polymer compound and water at, for example, 50° C. or higher, and then slowly cool to room temperature. , preferably 15 minutes or more, more preferably 30 minutes or more.
• the polymer compound used in the composition of the present invention is not particularly limited, but includes synthetic polymer compounds, semi-synthetic polymer compounds, natural polymer compounds, and the like.
• synthetic polymer compounds when the polymer compound has a hydrogen-bonding functional group, it can interact with water, the component (A) and/or the component (B), and the affinity increases, so the compound having a hydrogen-bonding functional group is preferred, and polymer compounds containing at least one selected from a hydroxyl group, a carbonyl group, a carboxy group, and a carboxylate group are particularly preferred.
• semi-synthetic polymer compounds and natural polymer compounds are preferred, and natural polymer compounds are more preferred. These may be used individually by 1 type, and may be used in combination of 2 or more type.
• Examples of synthetic polymer compounds include, but are not limited to, polyacrylic acid, vinyl acetate copolymer, maleic anhydride copolymer, polyvinyl alcohol, polyvinylpyrrolidone, polyethylene glycol, polyethylene oxide, and polyester. , polyacrylonitrile-based, polyamide-based, polyimide-based, polyamideimide-based, polymaleimide-based, polyurethane-based, polycarbonate-based, and polyarylate-based high molecular compounds.
• semisynthetic polymer compounds include, but are not limited to, cellulose derivatives (sodium carboxymethylcellulose, hydroxyethylcellulose, methylcellulose, ethylcellulose, nitrocellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, crystalline cellulose), sodium alginate, ester gum, Soluble starch etc. are mentioned.
• natural polymer compounds include, but are not limited to, polysaccharides, cellulose, nucleic acids or salts thereof, ribonucleic acids or salts thereof, water-soluble proteins (casein, collagen, gelatin, albumin, fibroin, elastin, keratin, sericin, etc.), hyaluronic acid or its salts, mucopolysaccharides (such as chondroitin sulfate), etc., and polysaccharides are particularly preferred.
• polysaccharides include, but are not limited to, xanthan gum, carrageenan, tamarind sea gum, gellan gum, guar gum, pectin, gum arabic, karaya gum, locust bean gum, daiutang gum, sodium alginate, agarose, hyaluronic acid, polygalactose.
• Natural polysaccharides such as uronic acid, carboxymethyl pullulan, carboxymethyl chitin, carboxymethyl chitosan, carboxymethyl mannan, carboxymethyl starch, carboxymethyl dextran, carboxyethyl cellulose, carboxy alkyl polysaccharides such as carboxymethyl pullulan, oxidized cellulose and oxidized starch and polysaccharides containing sulfate groups such as chondroitin sulfate, dermatan sulfate, heparin and heparan sulfate.
• polymer compounds having hydrogen-bonding functional groups are preferred, and water-soluble polymer compounds are more preferred.
• Such polymer compounds are preferably xanthan gum, carrageenan, gellan gum, guar gum, diutane gum and sodium alginate, more preferably xanthan gum, carrageenan, gellan gum, guar gum and diutane gum, and still more preferably xanthan gum and guar gum.
• compositions Compositions, Gel Compositions, and Thickened or To Thicken Compositions
• component (A), component (B), polymer compound, and water are blended in any ratio.
• the amount thereof is not particularly limited, for example, the total amount of component (A) and component (B) in the composition is preferably 90% by mass or less, and 50% by mass or less, from the viewpoint of being suitable for gel formation or thickening properties. is more preferable, 30% by mass or less is even more preferable, and 10% by mass or less is particularly preferable.
• the polymer compound in the composition is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more.
• composition of the present invention forms a gel through the interaction of component (A), component (B), water, and a polymer compound having hydrogen-bonding functional groups, and has a thickening effect.
• a polymer compound having a functional group such as a polysaccharide, is more likely to form a gel composition and is suitable for imparting a thickening effect and thixotropy.
• composition of the present invention forms a hydrogen bond with water by using the component (A) or the component (A) and the component (B) having a hydrogen-bonding functional group, and further by using a polymer compound. can be enhanced. Also, the interaction between the component (A) and the component (B) and the dense arrangement of the component (A) and the component (B) result in the development of electrical conductivity.
• the hydrogen-bonding functional group in component (A) or component (A) and component (B) further includes a hydrogen-bonding functional group when the polymer compound has a hydrogen-bonding functional group. interacts with enzymes and other biomaterials to stabilize them.
• composition of the present invention has good affinity between the composition and water, is suitable for gel formation, and has an excellent thickening effect. and both component (A) and component (B) preferably have a hydrogen-bonding functional group. On the other hand, it is preferable that the polymer compound has a hydrogen-bonding functional group. A composition that forms a gel has an excellent thickening effect.
• the composition of the present invention is excellent in that the viscosity decreases when a shearing force is applied, making it easy to apply to an object, and then the viscosity increases when the shearing force is not applied, making it difficult for dripping to occur on the application surface.
• component (A) or component (B) has a hydrogen-bonding functional group, and both component (A) and component (B) have a hydrogen-bonding functional group. It is preferable to have On the other hand, it is preferable that the polymer compound has a hydrogen-bonding functional group.
• composition of the present invention comprises an active ingredient made of an organic material or an inorganic material, in particular, hydrogen Excellent compatibility with active ingredients consisting of organic or inorganic materials with bonding functional groups (hydroxyl, carbonyl, carboxyl, carboxylate, amino, hydrogen atoms, etc.), and their solubility and dispersibility Furthermore, they are excellent in release properties and sustained release properties of their active ingredients.
• composition of the present invention is expected to have superior development in various uses.
• biomaterials such as water retention, conductivity, living organisms and enzymes
• examples include proteins, enzymes, amino acids and salts thereof, nucleic acids, antibodies / antigens, cells, (animals, plants, living tissues such as organs, biological and natural materials such as cellulose), solubility, dispersibility, release and sustained release, thickening and thixotropic properties of inorganic and organic materials , High specific heat, high thermal conductivity, lubricity, freezing point depression, boiling point elevation, vapor pressure depression, permeability, hydrophilicity, adsorptivity, reactivity, moisture retention, safety, etc.
• water retention / moisturizing agents for example, water retention / moisturizing agents, conductive materials, electrolyte materials, antistatic agents, biomaterial dissolution solvents, dispersion solvents, storage solvents and culture media, thickeners, organic materials or inorganic materials
• metals, metal oxides but not particularly limited, for example, silica, aluminum oxide (alumina), zirconia, titanium oxide, magnesium oxide, indium tin oxide (ITO), cobalt blue (CoO Al 2 O 3 ), antimony oxide, zinc oxide, cesium oxide, zirconium oxide, yttrium oxide, tungsten oxide, vanadium oxide, cadmium oxide, tantalum oxide, niobium oxide, tin oxide, bismuth oxide, cerium oxide, copper oxide, iron oxide, indium oxide , boron oxide, calcium oxide, barium oxide, thorium oxide, indium tin oxide, ferrite, etc.), carbon materials), dissolution solvents, dispersion solvents,
• each of the above preferred examples shown in formula (I), each of the above preferred examples shown in formula (II), and each of the above preferred examples shown in formula (III) are at least any of them. Any combination can be a more preferable embodiment based on the results of the examples. At least one combination of all of the above preferred examples shown in formulas (I) to (III) can be a more preferred embodiment based on the results of the examples.
• 2-Amino-2-hydroxymethyl-1,3-propanediol (Fuji Film Wako Pure Chemical Industries, Ltd.) and triethanolamine (Kanto Chemical Co., Ltd.) are used as the amine compound of component (A). Lactic acid, malic acid, and citric acid (Kanto Kagaku Co., Ltd.) are used as acids, and xanthan gum (Echo Gum T: manufactured by DSP Gokyo Food & Chemical) and carrageenan (Ceepigum FA: manufactured by DSP Gokyo Food & Chemical) are used as polymer compounds.
• gellan gum (Kelcogel: manufactured by Saneigen FFI), guar gum (SUPERGEL CSA 200/50: manufactured by Sankei), diutan gum (KELCO-VIS DG: manufactured by Sankei), the ammonium compound of component (A) Choline hydroxide (Tokyo Chemical Industry Co., Ltd.) was used as the solvent.
• guar gum SUPERGEL CSA 200/50: manufactured by Sankei
• diutan gum KELCO-VIS DG: manufactured by Sankei
• the ammonium compound of component (A) Choline hydroxide (Tokyo Chemical Industry Co., Ltd.) was used as the solvent.
• 1-butyl-3-methylimidazolium chloride (BMI-Cl) in Comparative Examples was manufactured by Tokyo Chemical Industry Co., Ltd., and glycerin was manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• composition was prepared by the following method (Tables 1A, B to 4A, B, Table 5).
• Tables 1A, B to 4A, B, Table 5 After mixing the component (A) and the component (B) described in Tables 1A, B to 4A, B, and Table 5 in water, the water is distilled off, and the resulting mixture or salt is a hydrate. and was liquid at 25°C.
• Examples 2 to 100 Compositions 2 to 100 Similarly, predetermined amounts of an amine compound (component (A)), an acid (component (B)), and a polymer compound listed in Tables 1A and B to Table 4A and B were prepared under the same conditions as in Example 1, Gel compositions 2 to 100 were obtained. In addition, each amine compound (component (A)), acid (component (B)) and water described in Examples 1 to 100 were premixed in the same amount as above to synthesize an ammonium salt, and then a polymer compound was added. It was confirmed that a gel composition was similarly obtained by adding, heating, stirring, dissolving, and cooling under the same conditions as in Example 1.
• compositions 102-106 Similarly, predetermined amounts of ammonium compound, acid, and polymer compound shown in Table 5 were prepared under the same conditions as in Example 101 to obtain gel compositions 102-106. Further, each ammonium compound, acid and water described in Examples 101 to 106 are premixed in the same charge amount as above, the polymer compound is added, and the mixture is heated and stirred under the same conditions as in Example 101, dissolved, and cooled. , confirmed that a gel-like composition was similarly obtained.
• Composition 107 1-butyl-3-methylimidazolium chloride 1.0 g (concentration in composition: 10% by mass), polymer compound xanthan gum 0.1 g (polymer compound concentration in composition: 1% by mass) and water 8 9 g was mixed, heated and stirred at 50° C. for 30 minutes to dissolve, and then cooled to room temperature over 60 minutes to obtain a gel composition 107 .
• Composition 108 1.0 g of glycerin (concentration in the composition: 10% by mass), 0.1 g of high molecular compound xanthan gum (concentration of high molecular compound in the composition: 1% by mass) and 8.9 g of water were mixed and heated at 50°C. After heating and stirring for 30 minutes for dissolution, the mixture was cooled to room temperature over 60 minutes to obtain a gel composition 108 .
• Composition 109 0.1 g of xanthan gum, which is a polymer compound (concentration of polymer compound in the composition: 1% by mass) and 9.9 g of water are mixed, heated and stirred at 50° C. for 30 minutes to dissolve, and then cooled to room temperature over 60 minutes. After cooling, a gel composition 109 was obtained.
• xanthan gum which is a polymer compound (concentration of polymer compound in the composition: 1% by mass) and 9.9 g of water are mixed, heated and stirred at 50° C. for 30 minutes to dissolve, and then cooled to room temperature over 60 minutes. After cooling, a gel composition 109 was obtained.
• the moisture content of the gel composition was measured with a Karl Fischer moisture meter, and 1.0 g of the sample was added to the screw tube without a lid, and the temperature and humidity were set to 40 ° C. and 40% RH. It was allowed to stand in a vessel (KCL-2000W manufactured by Tokyo Rikakikai Co., Ltd.) for 24 hours. The moisture content after 24 hours was measured (moisture content after test), and the water retention rate was calculated using the following formula to evaluate water retention (Table 6).
• B Moisture content after test (%)
• Moisture reduction rate (%) [(A (%) - B (%)) / A (%)] ⁇ 100
• Table 6 shows the moisture reduction rate.
• Compositions 20 to 24, 42, 66 and 93 (Examples 107 to 111 and 116 to 118) had a smaller water loss rate and better water retention than Compositions 107 to 109 (Comparative Examples 1 to 3).
• Composition 20 (Example 107) has higher moisturizing properties than Composition 107 (Comparative Example 1), and the hydrogen-bonding functional groups present in component (A) and/or component (B) in the composition according to the present invention was suggested to contribute to water retention.
• Composition 20 (Example 107) has better water retention than Composition 108 (Comparative Example 2) containing glycerin having a hydrogen-bonding functional group (hydroxyl group). It was confirmed that A) and component (B) (the ammonium salt formed from component (A) and component (B)) are effective in retaining water.
• ⁇ Hydrolytic enzyme activity measurement of urease> Urease activity was measured by quantifying the amount of ammonium ions produced from urea by the enzymatic reaction of urease by the indophenol method.
• a 1 mM substrate solution prepared by dissolving urea as a substrate in a pH 7.5 10 mM phosphate buffer
• 100 mL of a 1 mM substrate solution was placed in an Erlenmeyer flask and preheated at 30°C for about 30 minutes.
• the sample containing 0.5 mg of enzyme was added to the substrate solution and allowed to react at 30° C. for 60 minutes.
• a phenol solution (10 g of phenol and 50 mg of sodium pentacyanonitrosylferrate(III) were dissolved in ion-exchanged water, and then diluted to 1000 mL with ion-exchanged water to prepare).
• 2 mL and sodium hypochlorite solution (prepared by dissolving 5 g of sodium hydroxide and 8.4 mL of 5% sodium hypochlorite solution in ion-exchanged water, and then diluting to 1000 mL with ion-exchanged water). In addition, they were reacted for 20 minutes in a constant temperature bath at 37°C.
• the amount of ammonium ions produced was determined from the amount of indophenol obtained by measuring the absorbance at a wavelength of 635 nm (V-550: JASCO Corporation) of the reaction solution, and the urease activity was measured. Calculated. Ammonium ion was quantified using a calibration curve obtained by preparing an ammonium ion solution in the concentration range of 0.1 to 3.0 mM and quantifying by the indophenol method in the same manner as described above.
• Table 6 shows the enzyme activity retention rate.
• Compositions 20 to 24 (Examples 107 to 111) had a higher enzymatic activity retention rate and were superior in enzyme stabilizing effect than Compositions 107 to 109 (Comparative Examples 1 to 3).
• Composition 20 (Example 107) has a higher enzymatic activity retention rate than Composition 107 (Comparative Example 1), and the hydrogen-bonding functionality of component (A) and/or component (B) in the composition according to the present invention It was suggested that the groups contributed to the enzyme stabilizing effect.
• Composition 20 (Example 107) has better water retention than Composition 108 (Comparative Example 2) containing glycerin having a hydrogen-bonding functional group (hydroxyl group). It was confirmed that A) and component (B) (the ammonium salt formed from component (A) and component (B)) are effective in stabilizing the enzyme.
• the samples of gel compositions 20 to 24 are all viscous and have higher conductivity (lower surface resistivity) than composition 107 (Comparative Example 1). , it was confirmed that the antistatic effect is excellent. That is, the hydrogen-bonding functional groups in component (A) and/or component (B) in the composition according to the present invention, component (A) and component (B) (component (A) and component (B) It was suggested that the ammonium salt formed from ) is liquid at 25°C.
• composition according to the present invention has higher conductivity than the comparative example composition, it is suggested that the surface of the application object is uniformly coated, and other effects other than conductivity and antistatic effects It can be effectively applied to the target object.
• composition 111 (Comparative Example 4) 1-butyl-3-methylimidazolium chloride (BMI-Cl) 1.0 g, polymer compound xanthan gum 0.1 g (composition (BMI-Cl, polymer compound, water ), 8.9 g of water, and 0.1 g of ascorbic acid as an active ingredient (1% by mass of the composition (BMI-Cl, polymer compound, water)) were mixed. , at 50° C. for 30 minutes to dissolve the mixture, and then cooled to room temperature over 60 minutes to obtain a gel composition 111 containing an active ingredient.
• BMI-Cl 1-butyl-3-methylimidazolium chloride
• a Pierce vial (2 mL) was filled with a buffer (phosphate-buffered saline (PBS) solution), Lab Skin (Hoshino Laboratory Animal Breeding Co., Ltd.) was placed in the Pierce vial, and maintained at 32°C.
• a buffer phosphate-buffered saline (PBS) solution
• Lab Skin Hoshino Laboratory Animal Breeding Co., Ltd.
• 0.1 g of each of the gel compositions 110 and 111 described above was added to the surface of the lab skin (the amount of ascorbic acid in the added gel composition: 1.0 mg), and the mixture was heated at 32° C.
• compositions obtained by changing the order of addition of component (A), component (B), and polymer compound have the same thickening effect and thixotropy.
• the target product contained component (A), component (B), a polymer compound, and water, it had a thickening effect and thixotropy.
• the gel composition 112 (Comparative Example 5) did not become a gel even after standing for 60 minutes after the viscosity measurement, and did not exhibit thixotropy.
• none of the compositions 113 and 114 of Comparative Examples 6 and 7 were gelled, and a gel composition was not obtained.
• compositions 20, 66, and 93 as examples, 18 g of compositions 114, 115, 116, and 117 as comparative examples, and methyl ethyl ketone and 2 g of isopropanol as active ingredients were mixed and placed in a constant temperature bath at a temperature of 25°C and a humidity of 60% RH. placed. After 2.5 hours, 6 hours, 8 hours, and 24 hours, the weight of the composition in which the active ingredient was dissolved was measured, and the evaporation rate was calculated from the following formula.
• Evaporation rate formula [(G - H) / I x 100] - J
• G Weight (g) of the composition in which the active ingredient is dissolved before the test
• H Weight (g) of the composition in which the active ingredient was dissolved after each hour
• I Charged amount of active ingredient: 2 g
• J Evaporation rate of the composition after each time when the active ingredient is water
• Examples 119 to 121 had lower evaporation rates after 2.5 hours, 6 hours, 8 hours, and 24 hours than Comparative Examples 8 to 12. The sustained release of the substance was confirmed. Also, from Tables 10A and B, Examples 122 to 124 had lower evaporation rates after 2.5 hours, 6 hours, 8 hours, and 24 hours than Comparative Examples 13 to 17. confirmed the sustained release properties of the composition.

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