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WO2001051530A1 - Agent antimicrobien faiblement irritant a masse moleculaire elevee - Google Patents

Agent antimicrobien faiblement irritant a masse moleculaire elevee Download PDF

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Publication number
WO2001051530A1
WO2001051530A1 PCT/JP2001/000167 JP0100167W WO0151530A1 WO 2001051530 A1 WO2001051530 A1 WO 2001051530A1 JP 0100167 W JP0100167 W JP 0100167W WO 0151530 A1 WO0151530 A1 WO 0151530A1
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WO
WIPO (PCT)
Prior art keywords
polymer
monomer
antibacterial
skin
poly
Prior art date
Application number
PCT/JP2001/000167
Other languages
English (en)
Japanese (ja)
Inventor
Isei Hisamitsu
Hodaka Ito
Masanori Uda
Tatsu Miyamoto
Takao Ishida
Masaharu Ikemori
Original Assignee
Fancl Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fancl Corporation filed Critical Fancl Corporation
Priority to JP2001551114A priority Critical patent/JP3786874B2/ja
Publication of WO2001051530A1 publication Critical patent/WO2001051530A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions

Definitions

  • the present invention relates to an antibacterial polymer, a method for producing the same, and an antibacterial agent, a skin external preparation or a detergent composition containing the antibacterial polymer.
  • an ultraviolet absorber a polymer obtained by polymerizing a monomer having an ultraviolet absorbing group into a polymer has been proposed (JP-A-3-22013, JP-A-6-73336). No. 9, Japanese Patent Application Laid-Open No. H10-231341, Japanese Patent Application Laid-Open No. H10-231468).
  • Antibacterial agents include those called antibacterial active polymers or polymer antibacterial agents that aim at low toxicity and low irritation, and polythion-type antibacterial agents have been studied in the past. No. 2, p87, 1995). However, the use of cationic antibacterial agents has been limited because the effects of the salts are lost due to the presence of salts.
  • Poly-P-vinylphenol has been reported as a nonionic antibacterial polymer (antibacterial and antifungal vol.8, No.9, pi, 1980). In thermal polymerization and radical polymerization), a large amount of monomer remains and skin irritation cannot be reduced. [Disclosure of the Invention]
  • An object of the present invention is to provide an antibacterial polymer having low skin permeability and low irritation, which is suitably blended in an antibacterial agent, an external preparation for skin, or a cleaning composition, and a method for producing the same. .
  • the present inventors have conducted intensive studies to solve the above problems, and as a result, synthesized a polymer having an antibacterial monomer as a polymerization component by controlling the molecular weight distribution, and obtained a residual monomer, and a dimer, The inventors have clarified that a material having low skin permeability and low irritation can be obtained by eliminating oligomers such as trimers to such an extent that they are not substantially contained, thereby completing the present invention.
  • the present invention is a polymer containing an antimicrobial monomer as a polymerization component and containing substantially no monomer or oligomer.
  • the antibacterial monomer has the general formula (I)
  • (Meth) acryloylamines represented by the formula:
  • (meth) atalyloylamines refers to acryloylamines and / or metaatalyloylamines.
  • the polymer of the present invention may be a polymer containing a copolymer component other than the antibacterial monomer, and a vinyl monomer is preferable as the copolymer component.
  • the polymer of the present invention is preferably produced by an anion polymerization method. Furthermore, the present invention also relates to an antibacterial agent, an external preparation for skin and a detergent composition containing the polymer.
  • the antibacterial polymer contains substantially no monomer or oligomer, skin irritation caused by permeation of the low-molecular antibacterial agent through the skin can be reduced.
  • the substantially free of monomer or oligomer one present invention the analysis results by the gel permeation click port Matogurafi one (GPC), although containing organic amount of monomer and oligomer refers to a 5 weight 0/0 or less, It is more desirable that monomers and oligomers are not detected by GPC.
  • the monomer constituting the polymer of the present invention is a compound having both a molecular structure having antibacterial activity and a polymerizable molecular structure.
  • Molecular structures having antibacterial activity include, for example, quaternary ammonium salts, biguanides, phosphonium salts, pyridinium salts, phenol, benzoic acid, 2-hydroxy-2,4,6-cycloheptatrienone, stipitatic acid, polyvalent Functional groups composed of alcohols and the like are included.
  • Examples of the polymerizable molecular structure include functional groups consisting of ethylene, propene, amino group, and carboxyl group. Can be.
  • n is an integer of 0 to 2 and X represents a hydrogen atom or a halogen atom.
  • the bonding position of the hydroxyalkyl group to the ethylene group is not limited, but it is preferable that the hydroxyl group is bonded to the para position.
  • a particularly preferred monomer is P-hydroxystyrene.
  • examples of the monomer include, for example, a compound represented by the general formula (II)
  • (Meth) acryloylamines can also be mentioned.
  • a polymer substantially free of monomers and oligomers can be produced, for example, by the following method.
  • Anion polymerization initiators include, for example, alkyllithium, metal naphthalene, Grignard reagents, dialkylmagnesium, metal alkoxides, pyridine, etc.Select an appropriate initiator in relation to physical properties such as the resonance stabilization energy of the monomer be able to.
  • the initiator is added to the reaction system in the entire amount at once.
  • the reaction temperature is desirably in the range of 150 to 0 ° C, particularly -100 ⁇ -40 ° C.
  • the anion polymerization is generally performed under a high vacuum called a break seal method, but can also be performed under an argon atmosphere or a nitrogen atmosphere.
  • the average molecular weight of the obtained polymer can be controlled by the amount of the initiator used and the reaction time.
  • the reaction is stopped by adding a compound having active hydrogen, for example, water or methanol.
  • the target polymer material is a peptide
  • it can be produced, for example, as follows using a peptide synthesizing apparatus which has been remarkably developed in recent years.
  • a resin to which the carboxyl group end of 9-fluorenylmethyloxycarbonyl (Fmoc) amino acid is bonded is packed into a column, the Fmoc protecting group is removed, and the amino group is released. Let it form (force ring).
  • a peptide having the target amino acid sequence is synthesized from the carboxyl terminal to the amino terminal. After the elongation of the peptide chain is completed, the target peptide is obtained by cleaving from the resin and then removing the protecting groups of the Fmoc and amino acid side chains.
  • the step of forming peptide bonds proceeds with a reaction yield of 99% or more, the final product is a mixture of impurities, and is purified by high-performance liquid chromatography (HPLC).
  • HPLC high-performance liquid chromatography
  • the molecular weight of the polymer of the present invention is not particularly limited, the number average molecular weight is preferably 1,000 or more, and particularly preferably 2,500 or more, in order to exhibit the effect of reducing skin irritation. From the viewpoint of reducing skin irritation, the higher the molecular weight, the better.
  • the molecular weight is preferably 100,000 or less, particularly 50,000 or less.
  • the molecular weight of the polymer of the present invention can be selected preferably from 1,000 to: L00,000, particularly preferably from 2,500 to 50,000.
  • the molecular weight distribution of the polymer of the present invention is preferably narrow.
  • Mw / Mn is preferably 1.4 or less, particularly 1.2 or less, and particularly preferably 1.15 or less.
  • the polymer of the present invention can contain one or more kinds of monomers, if necessary, as a copolymer component in the antibacterial monomer as long as the effects of the present invention are not impaired.
  • Copolymerizable monomers include, for example, hydroxyshethyl methacrylate, hydroxyshethyl acrylate, N, N-dimethylaminopropylacrylamide, N-bulpyrrolidone, N-isopropylamide, 2-meta Atariloyloxyethyl phosphorylcholine and the like.
  • the amount of the copolymer component other than the antibacterial monomer is 90% by weight or less, preferably 70% by weight or less.
  • the polymer of the present invention can be widely applied as a component with low skin irritation to cosmetics, detergents, pharmaceuticals, quasi-drugs, etc.
  • aqueous, solubilizing It can take a wide range of dosage forms such as system, emulsification system, powder system, oil system, gel system, ointment system, aerosol system, water-oil 2-layer system, water-oil-powder 3-layer system.
  • dosage forms such as system, emulsification system, powder system, oil system, gel system, ointment system, aerosol system, water-oil 2-layer system, water-oil-powder 3-layer system.
  • it if it is a basic cosmetic, it can be widely applied in the form of facial cleanser, lotion, milky lotion, cream, gel, essence (cosmetic), pack mask, shaving cosmetic, etc. It is.
  • it is a drug or a quasi-drug it can be widely applied to various ointments and the like.
  • the dosage form and form which the polymer of the present invention can take are not limited to these dosage forms and forms.
  • known base components are widely used and blended according to the desired dosage form and form as long as the desired effects of the present invention are not impaired by their blending. be able to.
  • natural animal and vegetable oils such as olive oil, avocado oil, rice oil, grape seed oil, macadamia nut oil, corn oil, rapeseed oil, castor oil, castor oil, coconut oil, sucrose, beef tallow, horse oil, egg yolk oil, etc.
  • Waxes such as jojoba oil, beeswax, candelilla wax, carnauba wax and lanolin; polybutene, squalane, Hydrocarbons such as liquid paraffin, paraffin, petrolatum; lauric acid, myristic acid, noremitic acid, stearic acid, behenic acid, oleic acid, isostearic acid, linoleic acid, linolenic acid, hydroxyxtearic acid, etc.
  • Waxes such as jojoba oil, beeswax, candelilla wax, carnauba wax and lanolin; polybutene, squalane, Hydrocarbons such as liquid paraffin, paraffin, petrolatum; lauric acid, myristic acid, noremitic acid, stearic acid, behenic acid, oleic acid, isostearic acid, linoleic acid, linolenic acid, hydroxyxtearic acid,
  • Fatty acids such as cetanol, stearyl alcohol, behenyl alcohol, octynoledodecanol, cholesterol and phytosterol; and higher alcohols; isonoel isononanoate, isosecetyl octanoate, octyldodecyl myristate, and no.
  • Esters such as isopropyl luminate, isocetyl stearate, and glyceryl tri-2-ethylhexanoate; silicone oils such as methylpolysiloxane, methylhydrogenpolysiloxane, pentasiloxane with decamethinole resin, and methylphenyl / repolysiloxane; Polyhydric alcohols such as ethylene glycol, glycerin, diglycerin, 1,3-butylene glycol, 1,2-pentanediol; saccharides such as sorbitanore, mannitol, glucose, maltitol; gum arabic, carrageenan, xanthan gum, guar gum, Water-soluble polymers such as carboxyvinyl polymer and alkyl-modified carboxyvinyl polymer; organic solvents such as ethanol; powders such as titanium dioxide, myric, talc, kaolin, and titanium dioxide-coated mica;
  • FIG. 1 shows an NMR spectrum of the poly (P-hydroxystyrene) obtained in Synthesis Example 1.
  • FIG. 2 shows a gel-permeation chromatograph of the poly (P-hydroxystyrene) obtained in Synthesis Example 1.
  • FIG. 3 shows a comparison of the molecular weight and molecular weight distribution of the poly (P-hydroxystyrene) obtained in Synthesis Example 1 and a commercially available poly (P-hydroxystyrene).
  • N-atalylitol tris (hydroxymethyl) aminomethane was dissolved in O.lmol of triethylamine, and a solution of 0.055 mol of trimethylchlorosilane in tetrahydrofuran was added at _45 ° C and reacted for 12 hours. After completion of the reaction, distilled water was added, and the mixture was vigorously shaken. After standing still, the aqueous phase was discarded. Thereafter, N-acrylonitrile (trimethylsilyloxymethyl) aminoaminomethane was obtained by distillation under reduced pressure.
  • the molecular weight and molecular weight distribution were measured by GPC (columns GPC806, 804,802 in series, manufactured by Shimadzu Corporation) (Fig. 2).
  • a polymer having a number average molecular weight of 2945, a weight average molecular weight of 3377, a molecular weight distribution of 1.15, a narrow molecular weight distribution, and no residual monomers, dimers, trimers, etc. was synthesized. .
  • the molecular weight distribution is shown in Fig. 3 in comparison with commercially available poly (P-hydroxystyrene).
  • C in Fig. 3 is the poly (P-hydroxystyrene) from this synthesis example
  • A is a commercial product A (Marcarinka I MS-1 manufactured by Maruzen Petrochemical Co., Ltd.)
  • B is a commercial product B (Maruzen Petrochemical) Marcalinka MS S-2).
  • a peak identified as a monomer, dimer, or trimer is not detected, whereas in a commercial product, a peak identified as a monomer, dimer, or trimer appears.
  • the poly (P-hydroxystyrene-hydroxyxethyl methacrylate) block polymer obtained in Synthesis Example 2 and the poly (N-acryloyl tris (hydroxymethyl) aminomethane) obtained in Synthesis Example 3 were also As in Synthesis Example 1, the structure was confirmed by 400 MHz ⁇ -NMR, the molecular weight and the molecular weight distribution were measured by GPC, and the polymer having a narrow molecular weight distribution and no residual monomer, dimer, trimer, etc. It was confirmed that was synthesized. Antibacterial measurement
  • the antibacterial activity of N-acryloyl tris (hydroxymethyl) aminomethane against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida and mold was evaluated by a challenge test method based on USP XXII.
  • Three-dimensional cultured skin model sandwiched between (LSE-Hi g h, Toyobo Co., Ltd.) a lateral second chamber one diffusion cell, phosphate buffered saline antimicrobial agent to the donor side, placed in phosphate buffered salt solution receiver side was.
  • the system was maintained at 37 ° C, and after a predetermined time, the donor side and the receiver side were sampled, the drug amount ratio between the donor side and the receiver side was measured by HPLC, and the transmittance was calculated (Table 2).
  • the polymer of the present invention contains substantially no monomer or oligomer, the antibacterial activity against various bacterial species is maintained in the same manner as the antibacterial low molecular weight compound or the antimicrobial monomer, and the antibacterial low molecular weight compound is obtained. Alternatively, it has a remarkable effect that skin penetration is significantly lower than that of antibacterial monomers, and the skin is excellent in safety. Therefore, the polymer of the present invention is extremely useful as an antibacterial agent, especially as an antibacterial agent and antiseptic for skin external preparations and cleaning compositions.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Oncology (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Communicable Diseases (AREA)
  • Environmental Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un polymère antimicrobien faiblement irritant à pénétration cutanée réduite. Ce polymère est ajouté à des préparations antimicrobiennes, à des préparations pour la peau à usage externe ou à des compositions détergentes, par exemple. Bien qu'il contienne un monomère antimicrobien, ledit polymère est sensiblement exempt de monomères ou d'oligomères. L'invention concerne également un procédé de production de ce polymère par polymérisation anionique, ainsi que des préparations antimicrobiennes, des préparations pour la peau à usage externe et des compositions détergentes contenant ce polymère.
PCT/JP2001/000167 2000-01-14 2001-01-12 Agent antimicrobien faiblement irritant a masse moleculaire elevee WO2001051530A1 (fr)

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Application Number Priority Date Filing Date Title
JP2001551114A JP3786874B2 (ja) 2000-01-14 2001-01-12 低刺激性高分子抗菌剤

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JP2000-5164 2000-01-14

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003014274A1 (fr) * 2001-08-02 2003-02-20 Creavis Gesellschaft Für Technologie Und Innovation Mbh Produit de nettoyage antimicrobien
WO2003068898A1 (fr) * 2002-02-12 2003-08-21 Creavis Gesellschaft Für Technologie Und Innovation Mbh Formulations pour le lavage et le nettoyage contenant des polymeres antimicrobiens
JP2009007362A (ja) * 2008-07-02 2009-01-15 Fancl Corp 水溶性高分子抗菌剤
JP2009051821A (ja) * 2008-06-30 2009-03-12 Fancl Corp 水溶性高分子抗菌剤
EP3378909A1 (fr) * 2017-03-24 2018-09-26 Seiko Epson Corporation Composition d'encre aqueuse pour liquide de matière colorante et impression à jet d'encre
EP3378910A1 (fr) * 2017-03-24 2018-09-26 Seiko Epson Corporation Composition d'encre aqueuse pour liquide de matière colorante et impression à jet d'encre
US10358645B2 (en) 2008-12-04 2019-07-23 Curna, Inc. Treatment of erythropoietin (EPO) related diseases by inhibition of natural antisense transcript to EPO

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62179508A (ja) * 1986-02-03 1987-08-06 Mitsui Toatsu Chem Inc 揮発性物質の除去方法
US4729834A (en) * 1984-05-07 1988-03-08 Mitsui Toatsu Chemicals, Inc. Method for adsorbing and desorbing
JPH03277608A (ja) * 1990-03-27 1991-12-09 Nippon Soda Co Ltd Ｐ―アルケニルフェノール系重合体の製造方法
JP2000229813A (ja) * 1999-02-05 2000-08-22 L'oreal Sa ポリ（ヒドロキシスチレン）及び脂肪相を含む化粧品組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4729834A (en) * 1984-05-07 1988-03-08 Mitsui Toatsu Chemicals, Inc. Method for adsorbing and desorbing
JPS62179508A (ja) * 1986-02-03 1987-08-06 Mitsui Toatsu Chem Inc 揮発性物質の除去方法
JPH03277608A (ja) * 1990-03-27 1991-12-09 Nippon Soda Co Ltd Ｐ―アルケニルフェノール系重合体の製造方法
JP2000229813A (ja) * 1999-02-05 2000-08-22 L'oreal Sa ポリ（ヒドロキシスチレン）及び脂肪相を含む化粧品組成物

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003014274A1 (fr) * 2001-08-02 2003-02-20 Creavis Gesellschaft Für Technologie Und Innovation Mbh Produit de nettoyage antimicrobien
WO2003068898A1 (fr) * 2002-02-12 2003-08-21 Creavis Gesellschaft Für Technologie Und Innovation Mbh Formulations pour le lavage et le nettoyage contenant des polymeres antimicrobiens
JP2009051821A (ja) * 2008-06-30 2009-03-12 Fancl Corp 水溶性高分子抗菌剤
JP2009007362A (ja) * 2008-07-02 2009-01-15 Fancl Corp 水溶性高分子抗菌剤
US10358645B2 (en) 2008-12-04 2019-07-23 Curna, Inc. Treatment of erythropoietin (EPO) related diseases by inhibition of natural antisense transcript to EPO
EP3378909A1 (fr) * 2017-03-24 2018-09-26 Seiko Epson Corporation Composition d'encre aqueuse pour liquide de matière colorante et impression à jet d'encre
EP3378910A1 (fr) * 2017-03-24 2018-09-26 Seiko Epson Corporation Composition d'encre aqueuse pour liquide de matière colorante et impression à jet d'encre
CN108624138A (zh) * 2017-03-24 2018-10-09 精工爱普生株式会社 喷墨记录用水性油墨组合物以及色料液
CN108624141A (zh) * 2017-03-24 2018-10-09 精工爱普生株式会社 喷墨记录用水性油墨组合物以及色料液
CN108624141B (zh) * 2017-03-24 2021-10-29 精工爱普生株式会社 喷墨记录用水性油墨组合物以及色料液

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JP3786874B2 (ja) 2006-06-14

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