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WO2017047886A1 - Composition adhésive à base de dérivé du catéchol et procédé de production de cette dernière - Google Patents

Composition adhésive à base de dérivé du catéchol et procédé de production de cette dernière Download PDF

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Publication number
WO2017047886A1
WO2017047886A1 PCT/KR2016/002771 KR2016002771W WO2017047886A1 WO 2017047886 A1 WO2017047886 A1 WO 2017047886A1 KR 2016002771 W KR2016002771 W KR 2016002771W WO 2017047886 A1 WO2017047886 A1 WO 2017047886A1
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Prior art keywords
formula
group
methacrylate
adhesive
adhesive composition
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Ceased
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PCT/KR2016/002771
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English (en)
Korean (ko)
Inventor
황동수
오명환
서덕규
이도훈
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POSTECH Academy Industry Foundation
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POSTECH Academy Industry Foundation
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Publication of WO2017047886A1 publication Critical patent/WO2017047886A1/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Definitions

  • the present invention relates to an adhesive composition based on a catechol derivative and a method for preparing the same, and more particularly, to an adhesive composition based on a catechol derivative and a preparation method including a hydroxyl protecting group and various functional groups.
  • tooth adhesion is largely divided into enamel and dentin adhesion.
  • Enamel is a very hard tissue consisting of 95% mineral, 1% organic and 4% moisture.
  • Enamel adhesion generally dissolves hydroxyapatite crystals by acid corrosion to expose enmel rods to the surface, and micromechanically bonds as the adhesive penetrates and hardens.
  • Teeth dentin is composed of 70% mineral, 20% organic, 10% moisture. Compared with enamel, it is characterized by a lot of organic and moisture.
  • Early dentin adhesives were hydrophobic and did not penetrate the smear layer of dentin well. This resulted in very low adhesive strength.
  • hydrophilic monomers such as 2-hydroxy methacrylate (HEMA), which allowed the adhesive to penetrate the dentin layer and tolerate in wet environments. .
  • HEMA 2-hydroxy methacrylate
  • DOPA 3,4-dihydroxyphenyl-L-alanine
  • tyrosine one of the amino acids in living organisms, and a precursor of dopamine and norepinephrine, which are signaling agents.
  • DOPA is a material that plays a key role in the adhesion protein of mussels, which are marine organisms. For this reason, adhesives containing DOPA can be considered suitable for use as dental adhesives.
  • an adhesive composition based on a catechol derivative including a hydroxyl protecting group and various functional groups is excellent in biocompatibility, economical, and shows excellent adhesive strength even under wet conditions.
  • the present invention has been completed.
  • the present invention is to provide an adhesive composition and a method of manufacturing the same.
  • the present invention is to provide a bone adhesive, comprising the adhesive composition.
  • the present invention is to provide a dental adhesive, comprising the adhesive composition.
  • the present invention is to provide an implant kit comprising the dental adhesive.
  • the present invention is a.
  • P is a hydroxyl protecting group
  • L1 or L2 are each independently hydrogen, hydroxyl group, C 1 to C 20 carboxyl group, C 1 to C 10 linear or branched alkyl group, C 1 to C 10 alkoxy group, acrylate group, methacrylate And pentanerythritol tetrakis (3-mercaptopropionate, PETMP).
  • the present invention comprises the step of photopolymerizing a mixture of the compound of Formula 1, the methacrylate monomer, a photoinitiator, an aromatic tertiary amine having an electron withdrawing group, an organic solvent, and a filler; comprising, preparing an adhesive composition Provide a method.
  • the present invention also provides a bone adhesive, comprising the adhesive composition.
  • the present invention also provides a dental adhesive comprising the adhesive composition.
  • the present invention also provides an implant kit comprising the dental adhesive.
  • the adhesive composition according to the present invention is prepared by including a hydroxyl protecting group and various functional groups based on the catechol derivative compound, thereby providing excellent biocompatibility, economical efficiency, and excellent adhesion strength even under wet conditions. There is an effect that can be used as the adhesive for the.
  • FIG. 1 is a view showing a scanning electron microscope (Scanning Electron Microscopy, SEM) image of the dental root canal filling sealer of (a) Examples 3-5 and (b) Comparative Example 3.
  • the present invention provides an adhesive composition comprising the compound of formula (1).
  • P is a hydroxyl protecting group
  • L1 or L2 are each independently hydrogen, hydroxyl group, C 1 to C 20 carboxyl group, C 1 to C 10 linear or branched alkyl group, C 1 to C 10 alkoxy group, acrylate group, methacrylate And pentanerythritol tetrakis (3-mercaptopropionate, PETMP).
  • hydroxyl protecting group means a functional group that protects the hydroxyl group from undesirable reactions during the synthetic procedure.
  • the hydroxyl protecting group may be silyl ether, methyl ether, C 1 -C 6 alkyl ether, tetrahydropyranyl or -SiR 1 R 2 R 3, etc., but is preferably -SiR 1 R 2 R 3 .
  • examples of the hydroxyl protecting group include methyl, ethyl, propyl, t-butyl, isopropyl, methoxymethyl (MOM), methylthiomethyl, t-butylthiomethyl, (phenyldimethylsilyl) methoxymethyl, benzyl Oxymethyl, p-ethoxybenzyloxymethyl, (4-methoxyphenoxy) methyl, guoacolmethyl, t-butoxymethyl, 4-pentenyloxymethyl, siloxymethyl, 2-methoxyethoxymethyl , 2,2,2-trichloroethoxymethyl, bis (2-chloro-ethoxy) methyl and 2- (trimethylsilyl) -ethoxymethyl), 1-ethoxyethyl, 1- (2, chloroethoxy ) Ethyl, 1-methyl-1-methoxyethyl, 1-methyl-1-benzyloxyethyl, 1-methyl-1-benzyloxy-2-fluoroethyl, 2,
  • examples of the -SiR 1 R 2 R 3 is trimethylsilyl, triethylsilyl, tri-isopropyl silyl, dimethyl-isopropyl silyl, diethyl isopropyl silyl, dimethyl silyl teksil, tert- butyldimethylsilyl, di -tert- Butylmethylsilyl, tert-butyldiphenylsilyl, tribenzylsilyl, tri-p-xylylsilyl, triphenylsilyl, diphenylmethylsilyl, tert-butyl (methoxy) diphenylsilyl and the like.
  • the silylation step can be performed according to standard methodologies known to those skilled in the art.
  • the compound of Formula 1 is preferably a catechol derivative based compound.
  • the catechol derivative is a compound containing a dihydroxy group, and can be coordinated with the metal. Specifically, eugenol, dopa (3,4-dihydroxyphenylalanine (DOPA), dopa quinone (Dopa o-quinone), topa (2,4,5-trihydroxyphenylalanine (TOPA), or topa quinone (Topa quinone) And the like.
  • the compound of Formula 1 is substituted with a hydroxyl group to the hydroxyl protecting group to solve the disadvantage of oxidative stability of catechol, and various crosslinking agents to increase the compatibility with other monomers and oligomers It is preferably a compound based on substituted catechol derivatives.
  • the compound of Formula 1 may be a catechol derivative compound protected with -SiR 1 R 2 R 3 represented by the following Formula 2, Formula 3, Formula 4, Formula 5 or Formula 6.
  • R 1, R 2 or R 3 are each independently hydrogen, a C 1 to C 10 straight or branched alkyl group, C 1 to C 10 alkoxy, C 6 to C 10 aryl group and C 6 to C 10 heteroaryl group It is any one selected from the group consisting of.
  • eugenol and HSiR 1 R 2 R 3 compounds are reacted under tris pentafluorophenyl borane (TPFPB) to silyl-protected catechol (SPC)
  • TPFPB pentafluorophenyl borane
  • SPC silyl-protected catechol
  • the compound of Formula 2 may be prepared by preparing a compound and reacting the SPC with pentaneerythritol tetrakis (3-mercaptopropionate) (PETMP).
  • PETMP includes four thiol groups, SPC may bind to 1-4.
  • 3,4-dihydroxyphenylacetic acid (3,4-Dihydroxyphenylacetic acid) or homovanillic acid (Homovanillic acid) and HSiR 1 R 2 R 3 compound tris pentafluorophenyl borane (tris Reaction under pentafluorophenyl borane (TPFPB) can be used to prepare silyl-protected catecholic acid (SPC acid) compounds.
  • TPFPB pentafluorophenyl borane
  • the compound of Chemical Formula 6 may be prepared by sequentially esterifying the SPC acid, 1,10-decanediol (1, 10-decandiol), and methacrylic acid (Methacrylic acid).
  • 3,4-dihydroxyphenylacetic acid (3,4-Dihydroxyphenylacetic acid) or homovanillic acid (Homovanillic acid) to 1,10-decanediol (1, 10-decandiol
  • methacrylic acid Methacrylic acid
  • HSiR 1 R 2 R 3 compound was added under tris pentafluorophenyl borane (TPFPB) as in Scheme 3 above to attach the hydroxyl protecting group of catechol. Reaction may yield a compound of Formula 6.
  • the compound of Formula 1 is preferably included in 1 to 20% by weight relative to the total weight of the adhesive composition.
  • the adhesive composition may further include a methacrylate-based polymer monomer, a photoinitiator, an aromatic tertiary amine having an electron withdrawing group, an organic solvent, and a filler.
  • the methacrylate-based polymer monomer may include a hydrophobic methacrylate functional group, low volatility and polymerization shrinkage, fast curing, moderate molecular weight, and high stability monomer.
  • a hydrophobic methacrylate functional group low volatility and polymerization shrinkage, fast curing, moderate molecular weight, and high stability monomer.
  • 2,2-bis- (4- (2-hydroxy-3-methacryloyloxypropoxy) phenyl) propane Bis-GMA
  • TEGDMA triethylene glycol dimethacrylate
  • EGDMA ethylene Glycol Dimethacrylate
  • the methacrylate-based polymer monomer may be a polymer monomer having low viscosity and excellent hydrophilicity.
  • the content of the methacrylate monomer is not particularly limited, but is preferably 10 to 99% by weight, more preferably 10 to 90% by weight based on the total weight of the composition. If the content of the monomer is 10% by weight or less, it is difficult to form the desired polymer and not easy to be mixed with the filler. On the contrary, if the content of the monomer is 99% by weight or more, it is not preferable because of lack of workability due to an increase in viscosity.
  • the initiator of the polymerization reaction may function in various ways, such as a cation formation mechanism, an anion formation mechanism, a radical formation mechanism, and the like, depending on the type of catalyst used in the polymerization reaction, and a double radical formation mechanism is most commonly used. According to these polymerization mechanisms, the polymerization reaction may be performed by a photopolymerization reaction, a chemical polymerization reaction, or the like, but is not limited thereto.
  • the photopolymerization reaction is carried out by a photoinitiator which is activated by visible or ultraviolet (UV) light to initiate the polymerization of the monomer
  • the photoinitiator is camphorquinone, benzyl, 2,3-pentanedione, benzyldimethylketal, benzyl diethyl Ketal, 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzolyl) phenylphosphine oxide, Dibenzoylphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) phenylphosphine oxide, tris (2,4-dimethinbenzoyl) phosphine oxide, tris (2-methoxybenzoyl) phosphine oxide, 2, 6-dimethoxybenzoyldiphenylpho
  • the chemical polymerization reaction is carried out by a peroxide compound, such as benzoyl peroxide (BPO), used together with an aromatic tertiary amine promoter having an electron withdrawing group to form radicals by heat to initiate polymerization.
  • a peroxide compound such as benzoyl peroxide (BPO)
  • BPO benzoyl peroxide
  • aromatic tertiary amine which has the said electron attracting group
  • 4-N, N- dimethylamino benzoate ethyl, 4-N, N- dimethylamino benzoate, 4-N, N- dimethylamino benzoic acid propyl, 4-N , N-dimethylaminobenzoic acid 2-butoxyethyl, 4-N, N-dimethylaminobenzoic acid 2- (methacryloyloxy) ethyl, 4-N, N-dimethylaminobenzophenone and the like can be used.
  • the organic solvent may be methanol, ethanol, 1-propanol, isopropyl alcohol, acetone, methyl ethyl ketone, 1,2-dimethoxyethane, 1,2-diethoxyethane, tetrahydrofuran, but is not limited thereto. It is not.
  • the filler may be an inorganic filler, an organic filler, a stabilizer, or the like.
  • the inorganic filler may be amorphous synthetic silica, crystalline natural silica, barium aluminum silicate, kaolin, talc, strontium aluminum silicate, and the like, and other acid reactive fillers, nano zirconia fillers, and the like, but is not limited thereto.
  • the inorganic filler is hydrophilic, the compatibility with the hydrophobic polymerization monomer is inferior, and thus the affinity with the polymerization monomer can be enhanced by including a binder component or by surface treating the inorganic filler with a silane coupling agent.
  • the organic filler is synthesized in the form of a powder after synthesis of a monomer constituting the matrix after polymerization or monomers compatible with the dental restorative composition by bulk polymerization, emulsion polymerization, suspension polymerization, etc., the average particle diameter of 0.001 to 1 ⁇ m What was granulated can be used.
  • an inorganic or organic filler may not be added, but instead the mechanical strength may be increased by increasing the curing molecular weight of the monomer.
  • the stabilizer may preferably be a phenolic or phosphate stabilizer.
  • the adhesive composition may further include a known compound such as polymerization inhibitor, antioxidant, colorant, fluorine additive.
  • the present invention comprises the step of photopolymerizing a mixture of the compound of Formula 1, methacrylate-based monomer, photoinitiator, aromatic tertiary amine having an electron withdrawing group, an organic solvent, and filler; It provides a manufacturing method.
  • the photopolymerization is preferably performed for 1 to 24 hours under visible light or UV irradiation.
  • the present invention also provides a bone adhesive, comprising the adhesive composition.
  • the bone adhesive can maintain the adhesion even in the presence of water, it can be used for adhesion in water.
  • the present invention also provides a dental adhesive comprising the adhesive composition.
  • the dental adhesive may adhere to one or more substrates selected from the group consisting of biomaterials, plastics, glass, metals, and polymer synthetic resins, and may be used for bonding or fixing the substrates.
  • the dental adhesive can be used in various formulations, for example in the form of liquid, cement, primer or root canal filling sealer.
  • the dental adhesive may be for the prevention or treatment of periodontal disease.
  • the present invention also provides an implant kit comprising the dental adhesive.
  • Dental adhesives according to the present invention not only have excellent biocompatibility, but also exhibit excellent adhesive strength in teeth and various restorations.
  • the first separated reaction mixture was subjected to column chromatography using silica / nucleic acid: ethyl acetate (90:10) to separate a pure substance, thereby obtaining a methacrylate silylated catechol derivative (Methacrylated SPC) as a product. Obtained.
  • the silylated catechol derivatives (SPC) and pentane erythritol tetrakis (3-mercaptopropionate) prepared in Example 1-1 (pentaerythritol tetrakis (3-mercaptopropionate), PETMP) were prepared using dimethoxy-2-phenylaceto.
  • PETMP-SPC was obtained by reaction under a phenone (dimethoxy-2-phenylacetophenon) catalyst in an equivalent ratio of 1: 1: 0.05.
  • methacryloyloxy-decyl-dihydrogen-phosphate methacryloyloxi-decyl-dihydrogen-phosphate, 10-MDP
  • a liquid dental adhesive 1 having a composition of Table 1 was prepared, including methacrylate-SPC (or PETMP-SPC) according to Example 1.
  • Example 3-1 the content of methacrylate-SPC (or PETMP-SPC) was reduced to 5 wt%, and methacryloyloxy-decyl-dihydrogen-phosphate (methacryloyloxi-decyl-dihydrogen-phosphate, A liquid dental adhesive 2 was prepared in the same manner as in Example 3-1, except that 2% by weight of 10-MDP) was added.
  • Cement-type dental adhesive 1 including the composition of Table 2 (first paste) and Table 3 (second paste) including PETMP-SPC according to Example 1 was prepared.
  • Example 3-3 the content of PETMP-SPC was reduced to 10% by weight, and that of methacryloyloxy-decyl-dihydrogen-phosphate (methacryloyloxi-decyl-dihydrogen-phosphate, 10-MDP) Cement-type dental adhesive 2 was prepared in the same manner as in Example 3-3, except that the content was added by 5% by weight.
  • methacryloyloxy-decyl-dihydrogen-phosphate methacryloyloxi-decyl-dihydrogen-phosphate, 10-MDP
  • the dental root canal filling sealer 1 including the composition of Table 4 (first paste) and Table 5 (second paste) including PETMP-SPC according to Example 1 was prepared.
  • Example 3-5 the content of PETMP-SPC was reduced to 10% by weight, and of methacryloyloxy-decyl-dihydrogen-phosphate (methacryloyloxi-decyl-dihydrogen-phosphate, 10-MDP)
  • methacryloyloxy-decyl-dihydrogen-phosphate methacryloyloxi-decyl-dihydrogen-phosphate, 10-MDP
  • a liquid dental adhesive was prepared in the same manner as in Example 3-1, except that 4-META was contained in 7 wt% instead of methacrylate-SPC (or PETMP-SPC) in Example 3-1.
  • Cement-type dental adhesive was prepared in the same manner as in Example 3-3, except that 15 wt% of 4-META was substituted for PETMP-SPC in Table 3 of Example 3-3.
  • Example 4 of Table 3-5 except for containing 15% by weight of 4-META instead of PETMP-SPC, a dental root canal filling sealer was prepared in the same manner as in Example 3-5.
  • Adhesive strength to the dental adhesive according to Examples 3-1 to 3-4 and Comparative Examples 1 to 2 were measured. First, the tooth was polished so that the dentin layer of the tooth was exposed, and the surface of the tooth was corroded by acid treatment with 35% phosphate gel for 10 seconds. Thereafter, after removing the moisture on the surface of the tooth, a dental adhesive was applied to a certain amount of teeth, and then the restorative was lifted to photopolymerize to prepare a test piece. The prepared test piece was placed in distilled water and stored at 35 ° C. for 24 hours, and then the adhesive strength was measured by moving the crosshead at a speed of 0.8 mm / min using a universal testing machine. Its adhesive strength measurement results are shown in Table 6.
  • the dental adhesive according to Examples 3-1 to 3-4 including the methacrylate-SPC (or PETMP-SPC) of the present invention is 4-META. It can be seen that more excellent adhesive strength compared to the adhesive according to Comparative Examples 1 to 2 included.
  • the liquid adhesive of Example 3-2 and the cemented adhesive of Examples 3-4 as the methacryloyloxy-decyl-dihydrogen-phosphate (10-MDP) was added, further improved adhesion Strength is shown.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Inorganic Chemistry (AREA)
  • Surgery (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dental Preparations (AREA)
  • Engineering & Computer Science (AREA)
  • Composite Materials (AREA)
  • Materials Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne une composition adhésive à base de dérivé du catéchol et un procédé de production de cette dernière, et plus spécifiquement, une composition adhésive à base de dérivé du catéchol comprenant un groupe protecteur de type hydroxyle et divers groupes fonctionnels, et un procédé de production de cette dernière. La composition adhésive, selon la présente invention, est produite de manière à être basée sur un composé dérivé du catéchol et afin de comprendre un groupe protecteur de type hydroxyle et divers groupes fonctionnels, et de ce fait possède une excellente biocompatibilité, est économique et présente une excellente force d'adhésion même en condition humide et, par conséquent, a comme effet d'être apte à être utilisée comme adhésif dentaire ou chirurgical.
PCT/KR2016/002771 2015-09-16 2016-03-18 Composition adhésive à base de dérivé du catéchol et procédé de production de cette dernière Ceased WO2017047886A1 (fr)

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KR10-2015-0130958 2015-09-16
KR1020150130958A KR101799003B1 (ko) 2015-09-16 2015-09-16 카테콜 유도체 기반의 접착성 조성물 및 이의 제조방법

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KR102189253B1 (ko) * 2018-07-13 2020-12-09 차의과학대학교 산학협력단 다중 카테콜기를 포함하는 광중합 고분자 및 양이온성 무기 입자를 포함하는 의료용 만능 접착제 조성물 및 이의 제조방법

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005056708A2 (fr) * 2003-12-09 2005-06-23 Spherics, Inc. Polymeres bioadhesifs a fonction catechol
WO2008134024A2 (fr) * 2007-04-25 2008-11-06 Dentsply International Inc. Ciment dentaire autocollant
WO2013180459A2 (fr) * 2012-05-31 2013-12-05 한국교통대학교 산학협력단 Copolymère à greffe catéchol, composition copolymère contenant le copolymère réticulé, composition de matrice adhésive fonctionnelle, et son procédé de préparation
WO2014118266A1 (fr) * 2013-01-31 2014-08-07 National University Of Ireland, Galway Adhésif polymère
WO2015017562A1 (fr) * 2013-07-30 2015-02-05 The Regents Of The University Of California Substances adhésives et procédés de fabrication et d'utilisation de celles-ci

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101836504B1 (ko) 2012-02-22 2018-04-19 현대자동차주식회사 흡기밸브

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005056708A2 (fr) * 2003-12-09 2005-06-23 Spherics, Inc. Polymeres bioadhesifs a fonction catechol
WO2008134024A2 (fr) * 2007-04-25 2008-11-06 Dentsply International Inc. Ciment dentaire autocollant
WO2013180459A2 (fr) * 2012-05-31 2013-12-05 한국교통대학교 산학협력단 Copolymère à greffe catéchol, composition copolymère contenant le copolymère réticulé, composition de matrice adhésive fonctionnelle, et son procédé de préparation
WO2014118266A1 (fr) * 2013-01-31 2014-08-07 National University Of Ireland, Galway Adhésif polymère
WO2015017562A1 (fr) * 2013-07-30 2015-02-05 The Regents Of The University Of California Substances adhésives et procédés de fabrication et d'utilisation de celles-ci

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