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WO2007129747A1 - DÉRIVÉS DE L'ACIDE POLY-γ-GLUTAMIQUE C CONTENANT DE LA CYCLODEXTRINE - Google Patents

DÉRIVÉS DE L'ACIDE POLY-γ-GLUTAMIQUE C CONTENANT DE LA CYCLODEXTRINE Download PDF

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Publication number
WO2007129747A1
WO2007129747A1 PCT/JP2007/059626 JP2007059626W WO2007129747A1 WO 2007129747 A1 WO2007129747 A1 WO 2007129747A1 JP 2007059626 W JP2007059626 W JP 2007059626W WO 2007129747 A1 WO2007129747 A1 WO 2007129747A1
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Prior art keywords
pga
cyclodextrin
cyclodextrins
derivative
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PCT/JP2007/059626
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English (en)
Japanese (ja)
Inventor
Hiroshi Uyama
Yasushi Osanai
Moon-Hee Sung
Original Assignee
Osaka University
Genolac Bl Corporation
Bioleaders Corporation
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Filing date
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Application filed by Osaka University, Genolac Bl Corporation, Bioleaders Corporation filed Critical Osaka University
Publication of WO2007129747A1 publication Critical patent/WO2007129747A1/fr

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Classifications

    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations

Definitions

  • the present invention relates to a polyl -gnoretamic acid derivative containing cyclodextrins.
  • poly ( mono- mono-glutamic acid) having excellent biodegradability and biocompatibility and having moisture retention has attracted attention as a material for cosmetics and foods.
  • poly ⁇ -gnoretamic acid is also referred to as “PGA” in the present specification. Because PGA is the main component contained in the stickiness of natto, its safety is guaranteed by a long eating experience that is not only highly biocompatible. In addition, even if polymers having the same molecular weight are compared with each other, the PGA aqueous solution has low viscosity and has characteristics of being handled, easily, and industrially.
  • Patent Document 1 discloses a strain of the genus Bacillus that produces high molecular weight poly ⁇ -gnoretamic acid.
  • Patent Document 2 discloses poly-y-gnoretamic acid having an average molecular weight of 5, OOOkDa or more.
  • Patent Document 1 JP 2002-233391 A
  • Patent Document 2 International Publication WO2004-7593
  • the present invention is intended to further enhance the functionality of the PGA in consideration of the above-described conventional technology, and to provide a PGA derivative having high performance by introducing a special structure into the PGA. With the goal.
  • a cosmetic comprising the derivative according to item 1.
  • PGA derivative into which cyclodextrins are introduced can be obtained.
  • the inclusion ability can be expected to be improved.
  • cyclodextrins are known to have a three-dimensional structure like a bucket with a bottom.
  • a large number of hydrocarbons are present in the portion corresponding to the inside of the bucket and are hydrophobic
  • a large number of hydroxyl groups are present in the portion corresponding to the outside of the bucket and are hydrophilic.
  • cyclodextrins having such a special hydrophobic partial structure and hydrophilic partial structure are introduced into PGA having very high hydrophilicity, so that the disadvantage due to the high hydrophilicity of PGA. Is resolved.
  • cyclodextrins are known to be able to stabilize various unstable physiologically active substances (prostaglandins and the like). That is, it can be stabilized by inclusion of a substance that is unstable to light, ultraviolet rays or heat, or a substance that is easily oxidized or hydrolyzed with cyclodextrins.
  • Cyclodextrins can mask unpleasant odor, unpleasant taste, and the like by inclusion. For this reason, it can be used for various fragrances and foods. [0019] Cyclodextrins can be solubilized by inclusion of a substance that is hardly soluble in a solvent (for example, water).
  • a solvent for example, water
  • PGA derivative having both of these effects specific to cyclodextrins is provided.
  • Poly ⁇ -glutamic acid is a compound obtained by polymerization reaction of the amino group of D, L-glutamic acid and the force ruboxyl group at the ⁇ position.
  • PGA can also be used in the present invention as a salt thereof.
  • a sodium salt of PGA can be suitably used.
  • the molecular weight of PGA is not particularly limited. However, from the viewpoint of physical properties, the weight average molecular weight is preferably 10,000 or more, more preferably 100,000 or more. More preferably, it is 500,000 or more, and more preferably 1 million or more, particularly preferably 1.5 million or more, particularly preferably 2 million or more. In addition, the weight average molecular weight is preferably 13 million or less, more preferably 10 million or less in view of difficulty in synthesis.
  • Patent Document 1 Japanese Unexamined Patent Application Publication No. 2002-233391 describes PGA having a weight average molecular weight of about 13 million, and this PGA can be suitably used in the present invention.
  • the PGA used in the present invention can be produced by any known production method. For example, the method described in Patent Document 1 above can be used.
  • the PGA is a completely different compound from ⁇ -polyglutamic acid.
  • ⁇ -polyglutamic acid the ⁇ -carboxyl group is polycondensed with an amino group to form the main chain of the polymer.
  • Alpha polyglutamic acid does not exist in nature and can be obtained by chemical synthesis. Since glutamic acid has two carboxyl groups, branching occurs when polymerizing chemically. It is extremely difficult to synthesize a polymer that does not contain a branch that has a very high possibility of being produced, and even if it can be synthesized, it is extremely difficult to use it industrially because of its high cost. Therefore, ⁇ -polyglutamic acid is commercially available as a reagent and is used for various researches. Currently, it is hardly used industrially.
  • PGA gamma-polyglutamic acid
  • PGA is a carboxyl group position ⁇ constituting the main chain of the amino groups and polycondensing polymer.
  • PGA is a natural polymer contained in the stringing component of natto and is synthesized by an enzyme with high substrate specificity, so that its molecular structure is linear.
  • PGA has been confirmed to be highly safe based on its long dietary experience (natto).
  • different the polyglutamic acid ⁇ type is completely different substances of a type shed in the same polyglutamic acid, reactivity Ya properties and functions at all.
  • cyclodextrins are compounds in which a plurality of glucoses are bonded to form a large cyclic structure.
  • 6, 7 or 8 gnolecose forms a cyclic structure ( ⁇ , ⁇ -cyclodextrin).
  • One or more of the hydroxyl groups of cyclodextrin may be substituted with a substituent (for example, a lower acyl group).
  • a substituent for example, a lower acyl group.
  • the lower acyl group include a linear or branched alkyl carbonyl group.
  • the lower acylol group preferably has 6 or less carbon atoms, more preferably 4 or less.
  • the lower acyl group has 1 or more carbon atoms, and in one embodiment, 2 or more carbon atoms. Specific examples include a acetyl group and a propionyl group.
  • the method for synthesizing the compound of the present invention is not particularly limited, but in a preferred embodiment, PGA into which cyclodextrins are introduced is obtained by reacting PGA with cyclodextrins in the presence of an ester catalyst. It is done.
  • the number of moles of cyclodextrins used is appropriately selected according to the desired amount to be introduced to PGA. In general, 0.1% or more is preferred, 1% or more is more preferred, and 3% or more is more preferred, based on the number of moles of side chain carboxyl groups of PGA before the reaction5. / 0 or more is more preferable 10. / 0 or more is particularly preferable. 150% or more
  • the lower limit is preferably 100% or less, and more preferably 70% or less. More preferably 50% or less. In one embodiment, it may be 40% or less, and in another embodiment, it may be 30% or less.
  • the amount of CD in the obtained PGA derivative is smaller than the amount of cyclodextrins used. It is preferable to determine the amount of cyclodextrins used in the reaction, taking into account the decrease in the amount of CD.
  • a solvent for the reaction between cyclodextrins and PGA for example, water can be used.
  • the reaction between cyclodextrins and PGA can be performed using a condensing agent known to be usable for the reaction between carboxylic acid and alcohol. Although it is possible to carry out the reaction without using a condensing agent, it is extremely preferable to use a condensing agent from the viewpoint of reaction efficiency. Since the reaction in the production method of the present invention is preferably performed in an aqueous solvent, the condensing agent is preferably a water-soluble condensing agent. Examples of the water-soluble condensing agent include water-soluble carbodiimide, triazine-type dehydrating condensing agent, and the like, preferably water-soluble carbohydride.
  • condensing agent used in the production method of the present invention include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC) which is a water-soluble carbopositimide.
  • EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
  • the amount of the condensing agent (eg, EDC) used is preferably 1 mol or more, preferably 2 mol or more, per mol of cyclodextrins 2.5 mol or more.
  • the power is preferable. Further, it is preferably 10 mol or less, more preferably 8 mol or less, more preferably 6 mol or less, per 1 mol of cyclodextrins.
  • the reaction can also be carried out using an active auxiliary together with a condensing agent.
  • An activity auxiliary agent increases the activity of the condensing agent.
  • the water-soluble carpositimide active aid include N-hydroxysuccinimide (NHS).
  • the amount of active aid used Is preferably a force of 0.1 mol or more per mol of the condensing agent, preferably 0.1 mol or more, more preferably 0.5 mol or more. Further, it is preferably 10 mol or less, more preferably 5 mol or less, and further preferably 3 mol or less, per 1 mol of the condensing agent.
  • NHS is used as the activity aid, it is preferable to use about 0.
  • a catalyst for the reaction of cyclodextrins with PGA a catalyst known to be usable for the reaction of carboxylic acid and alcohol can be used as necessary.
  • a catalyst known to be usable for the reaction of carboxylic acid and alcohol can be used as necessary.
  • the usage-amount of a catalyst it can set suitably according to the kind and performance of each catalyst.
  • the temperature during the reaction is not particularly limited. It may be warmed at room temperature. However, if the temperature is too low, the reaction takes a very long time, so it is preferable to carry out the reaction at room temperature or above room temperature. Specifically, the temperature is preferably 10 ° C or higher, more preferably 15 ° C or higher, and further preferably 20 ° C or higher. Further, it is preferably 100 ° C. or lower, more preferably 50 ° C. or lower. If it is too high, the PGA is prone to degradation. Therefore, it is preferable to carry out at around room temperature.
  • the reaction time is preferably 30 minutes or more, more preferably 1 hour or more, further preferably 2 hours or more, and, more preferably, 6 hours or more. Especially preferred is 12 hours or more. However, in order to shorten the overall length of the process, it is preferably 7 days or less, more preferably 4 days or less, and even more preferably 2 days or less.
  • EDC activates a carboxyl group under conditions of weakly acidic to basic pH, and the active intermediate reacts with an amino group or a hydroxyl group to form an amide bond or an ester bond.
  • Examples of the use of EDC are described in Biomaterials 17 765-773 (1996) and journal of Applied Polymer Science 90 747-753 (2003).
  • the reaction can be carried out efficiently.
  • the pH during the reaction is preferably 6 or more, more preferably 7 or more. Further, it is preferably 11 or less, more preferably 10 or less.
  • reaction After the reaction is completed, neutralize as necessary, remaining reaction materials (condensation agent, active assistant, etc.) ) Removal, solvent removal and purification, etc., the derivative of the present invention is obtained.
  • an alkali such as sodium hydroxide, potassium hydroxide, sodium bicarbonate or arginine can be used.
  • the cyclodextrins are preferably directly bonded to the side chain force of the PGA ruboxyxyl group. If necessary, the cyclodextrins are bonded to the carboxyxyl group of the PGA via a linker. Moyore.
  • the linker any low-molecular compound having a functional group capable of binding to a hydroxyl group of cyclodextrin and a functional group capable of binding to a carboxyl group of PGA can be used.
  • the molecular weight of such a low molecular weight compound is preferably 500 or less, more preferably 300 or less. Moreover, it is preferable that it is 50 or more.
  • the main chain of the linker is preferably an alkylene group.
  • linker for example, a functional group that can be bonded to a hydroxyl group of cyclodextrin on a lower alkylene (for example, alkylene having 1 to 5 carbon atoms) and a functional group that can be bonded to a carboxyl group of PGA. Any compound having can be preferably used.
  • the derivative obtained by the above-described method has a structure in which cyclodextrins are covalently bonded to some of the side chain carboxyl groups of PGA by ester bonds.
  • the number of moles of cyclodextrins to be introduced can be controlled by adjusting the blending amount and reaction time when the cyclodextrins are reacted with PGA.
  • the number of moles of cyclodextrins to be introduced can be appropriately designed according to the application. 0.001% or more is preferable with respect to the number of moles of the side chain carboxy group of PGA before the reaction, and 0.1 Q / o or more is more preferable1. / 0 or more is more preferable 3% or more is particularly preferable.
  • it is preferably 80% or less, more preferably 60% or less, and still more preferably 40% or less. In one embodiment, 20. It can also be less than / o, and in another embodiment, 10. It may be less than / o. If the amount to be introduced is too small, introduce cyclodextrins. Effects are difficult to obtain. If too much is introduced, the resulting PGA derivative may lose its PGA performance.
  • the glucose unit constituting the cyclodextrin has a secondary hydroxyl group at the 2nd and 3rd positions and a primary hydroxyl group at the 6th position.
  • the primary hydroxyl group at the 6-position reacts with the side chain carboxyl group of PGA.
  • the PGA derivative has one end of the linker bonded to a part of the side chain carboxyl group of PGA, and the other end of the linker is a hydroxyl group of cyclodextrins. It has a structure bonded to.
  • the bond between the side chain carboxyl group of PGA and the linker may be an ester bond or another bond (for example, an amide bond).
  • any bond may be adopted for the bond between the linker and the hydroxyl group of the cyclodextrins.
  • the derivatives of the present invention are expected to be applied in a wide range of fields.
  • the hydrophilicity is controlled while maintaining the biocompatibility of PGA, and the action effect unique to cyclodextrin is added, so it is used as various materials in various fields such as pharmaceuticals, cosmetics and foods. It becomes possible.
  • the force of the present invention has the disadvantage that it is difficult to mix the hydrophobic material even if it is mixed, and the derivative of the present invention does not have such a disadvantage.
  • Hydrophobic materials can be easily mixed. The resulting mixture is stable without separation for a long time. For this reason, it is very advantageous when it is desired to mix hydrophobic materials (eg lipoic acid, austaxanthin, vitamin E, etc.).
  • hydrophobic materials eg lipoic acid, austaxanthin, vitamin E, etc.
  • hydrophobic materials eg lipoic acid, austaxanthin, vitamin E, etc.
  • a composition comprising a PGA-CD derivative and a hydrophobic functional material (lipoic acid, astaxanthin, vitamin E, etc.). This composition can be widely used in applications such as cosmetics (for example, cosmetics), foods, and pharmaceuticals, and is industrially useful.
  • the cosmetic refers to any conventionally known cosmetic, and includes cosmetics.
  • skin care cosmetics such as lotions, emulsions, creams, foundations, eye shadows, lipsticks, hair cosmetics, emollient creams, emollient lotions, foundations.
  • the cosmetic of the present invention contains the PGA-CD derivative.
  • the content of the PGA-CD derivative is not particularly limited, but is preferably 1% by weight or more, more preferably 10% by weight or more, and further preferably 20% by weight or more of the cosmetic. In the embodiment, it is 30% by weight or more, and may be 40% by weight or more or 50% by weight or more as required. Further, it is preferably 99% by weight or less, more preferably 95% by weight or less, and in one embodiment, 90% by weight or less, and 80% by weight or less or 70% by weight or less as required. It can also be.
  • the cosmetic of the present invention contains a hydrophobic functional material in addition to the PGA-CD derivative.
  • the hydrophobic functional material include lipoic acid, wastaxanthin and vitamin E.
  • the content of the hydrophobic functional material in the cosmetic is preferably 0.01% by weight or more, more preferably 0.1% by weight or more, and further preferably 1% by weight or more. In one embodiment, it is 3% by weight or more, and can be 5% by weight or more or 10% by weight or more as required. Further, it is preferably 50% by weight or less, more preferably 40% by weight or less, and in one embodiment, 30% by weight or less, and 20% by weight or less or 15% by weight or less as required. It can also be.
  • the cosmetic may be substantially composed of the PGA-CD derivative and the hydrophobic functional material, but if necessary, components other than the PGA_CD derivative and the hydrophobic functional material may be added. It may be added. It is possible to add various ingredients conventionally used in cosmetics to the cosmetics of the present invention. Specifically, various types such as solvents (for example, water, ethanol, etc.), colorants (for example, organic pigments, inorganic pigments, etc.), thickeners, surfactants, fragrances, ultraviolet absorbers, antioxidants, etc. Additives can be added.
  • solvents for example, water, ethanol, etc.
  • colorants for example, organic pigments, inorganic pigments, etc.
  • thickeners for example, surfactants, fragrances, ultraviolet absorbers, antioxidants, etc.
  • Additives can be added.
  • PGA sodium salt (PGANa) having a molecular weight of about 2 million was obtained. This was used in the following experiment.
  • a PGANa salt solution (0.45 lg) corresponding to 3 mmol as a glutamic acid monomer was dissolved in 70 mL of deionized water to prepare a PGANa salt aqueous solution.
  • a PGANa salt aqueous solution To this aqueous solution, -cyclodextrin (i3-CD) 0.3 mmol (0.341 g) was added and dissolved, then N-hydroxysuccinic acid imide (NHS) O. 9 mmol (0. 104 g) was prepared, and then 1 The reaction was started by adding 0.99 mmol (0.172 g) of ethyl 3- (3 dimethylaminopropyl) -carposimide hydrochloride (EDC).
  • EDC dimethylaminopropyl
  • the amount of / 3 cyclodextrin (/ 3—CD) used is 0.6 mmol (0.681 g), and the amount of N-hydroxysuccinimide (NHS) is 1.8 mmol (0.207 g).
  • the experiment was performed in the same manner as in Example 1 except that the amount of 1-ethyl_3_ (3-dimethylaminopropyl) -carbodiimide hydrochloride (EDC) was 1.8 mmol (0.346 g).
  • EDC 1-ethyl_3_ (3-dimethylaminopropyl) -carbodiimide hydrochloride
  • the yield based on the amount of PGA and j3-cyclodextrin used was 38%.
  • the ⁇ CD introduction rate was 6.4%.
  • the amount of; 3-cyclodextrin (i3-CD) used is 0.9 mmol (l. 022g), and the amount of N-hydroxysuccinimide (NHS) is 0.7 mmol (0.311g).
  • the experiment was conducted in the same manner as in Example 1 except that the amount of 1-ethyl-3- (3 dimethylaminopropyl) carpositimide hydrochloride (EDC) was changed to 2.7 mmol (0.518 g). As a result, the yield was 38% based on the amount of PGA and cyclodextrin used (based on the theoretical yield assuming that all cyclodextrin used was charged to the charged PGA).
  • the ⁇ CD introduction rate was 9 ⁇ 6%.
  • Example 1 PGA (Acid form) was used instead of PGANa.
  • Hi-cyclodextrin (Hi-CD) is used instead of ⁇ -cyclodextrin (/ 3-CD)
  • the experiment was conducted in the same manner as in Example 4 except that the amount of material used was changed as shown in the following table. As a result, derivatives having different introduction rates were obtained.
  • the following table shows the results
  • Example 4 The same as in Example 4 except that ⁇ -cyclodextrin ( ⁇ -CD) was used instead of ⁇ -cyclodextrin (j3-CD), and the amount of materials used was changed as shown in the table below. Test was carried out. As a result, derivatives having different introduction rates were obtained. The following table shows the results
  • the experiment was performed in the same manner as in Example 4 except that the amount of the solvent was 7 ml and PGA 1.3 mmol, NHS 1.2 mmol, and EDCl 2 mmol were used.
  • the experiment was performed in the same manner as in Example 7 except that the amount of the solvent was 7 ml, and PGA 1.3 mmol, NHS 1.2 mmol, and EDCl 2 mmol were used.
  • the mixture was stirred with TUBE MIXER for 1 minute x 5 times (total 5 minutes), and the absorbance and transmittance at 600 nm were measured.
  • a quartz cell was used, and the reference was distilled water. Absorbance and transmittance were measured respectively.
  • Example 13 increased the transmittance by 13%.
  • Example 14 In Example 13 above, the experiment was performed using the sample of Example 11 under the following conditions.
  • Example 14 The results of Example 14 and Comparative Example 2 are shown in the following table.
  • Example 1 compared to Comparative Example 2
  • Example 13 the experiment was performed using the Sampnore of Example 12 under the following conditions.
  • Example 15 The results of Example 15 and Comparative Example 3 are shown in the following table. Compared to Comparative Example 3, Example 1
  • CD VE ⁇ -CD VE permeability Sample Solvent 0D 600
  • the PGA-CD derivative of the present invention has a low water-soluble, hydrophobic functional material (lipoic acid, austaxanthin, vitamin E, etc.) and a cyclodextrin (CD) function that can include a fragrance. It is a new material that combines functions (humidity retention, anti-aging, etc.). For this reason, it becomes easy to introduce hydrophobic functional materials (lipoic acid, austaxanthin, vitamin E, etc.) having low water solubility into products such as cosmetics having moisture retention based on the function of PGA.
  • hydrophobic functional materials lipoic acid, austaxanthin, vitamin E, etc.
  • the PGA-CD derivative of the present invention can be widely used in cosmetics, foods, pharmaceuticals and the like.
  • PGA derivatives into which cyclodextrins are introduced are provided. This makes it possible to include various biological materials (for example, pharmaceuticals) in various applications of nanotechnology to produce various effects.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Polyamides (AREA)

Abstract

L'invention porte sur un dérivé de l'acide poly-γ-glutamique (PGA) dans lequel de la cyclodextrine a été introduite. La cyclodextrine est de préférence liée à environ 1 à 30% du groupe carbonyle de la chaîne latérale du PGA. Il est ainsi possible de conférer au PGA des propriétés inhérentes de la cyclodextrine (par exemple: stabilisation d'une substance instable, masquage d'une odeur déplaisante, masquage d'un gout désagréable, etc.). On peut donc utiliser ce dérivé dans différentes applications dont les biotechnologies.
PCT/JP2007/059626 2006-05-09 2007-05-09 DÉRIVÉS DE L'ACIDE POLY-γ-GLUTAMIQUE C CONTENANT DE LA CYCLODEXTRINE WO2007129747A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021181573A (ja) * 2017-03-02 2021-11-25 国立大学法人大阪大学 ホスト基含有重合性単量体、高分子材料及びその製造方法、並びに、包接化合物及びその製造方法

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JP6507426B2 (ja) * 2016-12-14 2019-05-08 三重県 ポリ−γ−グルタミン酸のリン酸誘導体及びその製造方法
CN113087895B (zh) * 2021-03-18 2022-08-23 黄河三角洲京博化工研究院有限公司 一种高分子量化妆品级聚谷氨酸的制备方法

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Publication number Priority date Publication date Assignee Title
JPH0692870A (ja) * 1992-09-16 1994-04-05 Meiji Seika Kaisha Ltd 薬物担体用高分子および徐放性制ガン剤
JP2000290370A (ja) * 1999-04-07 2000-10-17 Dainippon Ink & Chem Inc 吸水性材料
JP2002128899A (ja) * 2000-10-27 2002-05-09 Kanagawa Prefecture 生分解性を有する吸水性高分子

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0692870A (ja) * 1992-09-16 1994-04-05 Meiji Seika Kaisha Ltd 薬物担体用高分子および徐放性制ガン剤
JP2000290370A (ja) * 1999-04-07 2000-10-17 Dainippon Ink & Chem Inc 吸水性材料
JP2002128899A (ja) * 2000-10-27 2002-05-09 Kanagawa Prefecture 生分解性を有する吸水性高分子

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021181573A (ja) * 2017-03-02 2021-11-25 国立大学法人大阪大学 ホスト基含有重合性単量体、高分子材料及びその製造方法、並びに、包接化合物及びその製造方法
US12054571B2 (en) 2017-03-02 2024-08-06 Osaka University Host-group-containing polymerizable monomer, polymer material, method for producing same, and clathrate compound and method for producing same

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