WO2023181514A1 - Composition de résine antimicrobienne - Google Patents

Composition de résine antimicrobienne Download PDF

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Publication number
WO2023181514A1
WO2023181514A1 PCT/JP2022/045123 JP2022045123W WO2023181514A1 WO 2023181514 A1 WO2023181514 A1 WO 2023181514A1 JP 2022045123 W JP2022045123 W JP 2022045123W WO 2023181514 A1 WO2023181514 A1 WO 2023181514A1
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WO
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Prior art keywords
antibacterial
resin composition
resin
urethane resin
antibacterial agent
Prior art date
Application number
PCT/JP2022/045123
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English (en)
Japanese (ja)
Inventor
伸治 九鬼
健 野田
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三菱電機株式会社
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Publication of WO2023181514A1 publication Critical patent/WO2023181514A1/fr

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Classifications

    • 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
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • 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
    • C08K5/20—Carboxylic acid amides
    • 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
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • 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
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

Definitions

  • the present disclosure relates to an antibacterial resin composition.
  • Antibacterial processing methods include, for example, methods of kneading and dispersing antibacterial agents into resin and methods of applying antibacterial coating to the resin surface. Antibacterial agents are kneaded into resin during resin molding processes such as injection molding and extrusion molding. Because of this, a method of kneading and dispersing antibacterial agents into resin is often practiced.
  • Inorganic antibacterial agents include zeolite, silica gel, glass, calcium phosphate, etc. supported with metal ions such as silver, zinc, copper, etc.
  • Organic antibacterial agents include alcohol-based, thiazoline-based, imidazole-based, etc. can be mentioned respectively.
  • Inorganic antibacterial agents have good heat resistance and weather resistance for antibacterial agent-containing resin products, but they may reduce physical properties such as mechanical strength, and because they contain metal ions, discoloration of the resin or large quantities may occur. There are concerns about the impact of consumption on the ecosystem. Organic antibacterial agents do not reduce the mechanical strength of the product, but have drawbacks in heat resistance and weather resistance. Additionally, inorganic and organic antibacterial agents are expensive. Therefore, the use of materials not normally used for antibacterial purposes as antibacterial agents is being considered.
  • Patent Document 1 JP-A No. 2008-31092 discloses a resin molded article in which a hindered phenol derivative is blended into a resin as an antibacterial agent.
  • the resin molded product has excellent compatibility between the resin and antibacterial agent, moldability, thermal stability, safety, etc., so it is an antibacterial resin with excellent moldability, transparency, thermal stability, safety, etc. It is also stated that molded products and antibacterial articles will be provided.
  • Patent Document 2 JP-A-10-265585 discloses a resin molded product in which a hindered amine substance is blended as an antibacterial agent into a polyacetal resin. It is also described that the resin molded product has excellent antifungal and antibacterial properties while maintaining mechanical properties.
  • the urethane resin when a hindered amine-based substance is blended into a urethane resin, the urethane resin has the following properties: fluidity of the resin composition, moldability such as releasability from a mold, and surface properties such as scratch resistance. It is common to add a lubricant to improve this, but the antibacterial properties are inhibited due to the lubricant bleeding onto the resin surface, making it impossible to obtain sufficient antibacterial properties.
  • the present disclosure has been made in view of the above problems, and aims to provide an antibacterial resin composition that is a urethane resin containing a lubricant and has excellent antibacterial properties.
  • An antibacterial resin composition containing a urethane resin, a lubricant, and a hindered phenol derivative, a hindered amine derivative, and a benzotriazole derivative as antibacterial agents.
  • an antibacterial resin composition with excellent antibacterial properties in a urethane resin containing a lubricant.
  • the antibacterial resin composition of this embodiment includes a urethane resin, a lubricant, and as antibacterial agents a hindered phenol derivative (antibacterial agent A), a hindered amine derivative (antibacterial agent B), and a benzotriazole derivative (antibacterial agent C).
  • a hindered phenol derivative antioxidant
  • antibacterial agent B hindered amine derivative
  • antibacterial agent C benzotriazole derivative
  • the antibacterial resin composition of the present embodiment exhibits excellent antibacterial properties that are not affected by lubricants by containing the above-mentioned antibacterial agents A to C as antibacterial agents. Each component will be explained in detail below.
  • the antibacterial resin composition of this embodiment is made by dispersing a lubricant and an antibacterial agent in a urethane resin.
  • a urethane resin there are no particular limitations on the urethane resin, and examples thereof include thermoplastic urethane resins, thermosetting urethane resins, and the like. Examples of these resins include ether-based urethane resins, ester-based urethane resins, and carbonate-based urethane resins.From the viewpoint of superior environmental resistance such as water resistance and weather resistance, thermoplastic ether-based urethane resins are preferred. preferable. These urethane resins may be used alone or in an appropriate combination of two or more as a polymer blend.
  • the antibacterial resin composition of this embodiment contains a lubricant. Containing a lubricant improves the fluidity of the urethane resin and improves moldability.
  • the lubricant is not particularly limited and includes, for example, fatty acid ester, higher alcohol, polyhydric alcohol, glycerin ester, sorbitan ester, fatty acid, fatty acid amide, oil-based wax, etc., with fatty acid amide being preferred. This is because fatty acid amide does not have high compatibility with urethane resins, and by precipitating on the resin surface, it is possible to improve mold releasability, smoothen the surface of the molded product, and reduce friction. These lubricants may be used alone or in an appropriate combination of two or more.
  • the content of the lubricant in this embodiment is 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the urethane resin. If the content of the lubricant is less than 0.05 parts by weight, the antibacterial resin composition cannot improve its fluidity, moldability such as releasability from a mold, and surface properties such as scratch resistance. If the content of the lubricant exceeds 20 parts by weight, the fluidity of the antibacterial resin composition may become too good, and the moldability may deteriorate, such as the urethane resin dripping.
  • Antibacterial agent A contained in the antibacterial resin composition of this embodiment has a structure represented by the following chemical formula 1 in its molecule.
  • R is a hydrogen atom or an alkyl group.
  • Antibacterial agent A used in this embodiment known hindered phenol derivatives can be used.
  • Antibacterial agent A of the present embodiment includes a first hindered phenol derivative antibacterial agent (antibacterial agent A1) that has excellent compatibility with urethane resin, and a second hindered phenol derivative antibacterial agent that has excellent solubility in lubricants.
  • Antibacterial agents (antibacterial agents A2) can be broadly classified into two types, and contain at least one each of antibacterial agents A1 and antibacterial agents A2.
  • the antibacterial agent A1 includes (1) pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], (2) thiodiethylene bis[3-(3,5-di- tert-butyl-4-hydroxyphenyl)propionate], (3) N,N'-hexane-1,6-diylbis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionamide], (4) 2,4-dimethyl-6-(1-methylpentadecyl)phenol, (5) Calcium diethylbis[[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl] phosphonate], (6) ethylenebis(oxyethylene)bis[3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate], (7) hexamethylenebis[3-(3,5-di- tert
  • Antibacterial agent A2 includes (9) dibutylhydroxytoluene, (10) octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, (11) 3,3',3',5 , 5',5"-hexa-tert-butyl-a,a',a"-(mesitylene-2,4,6-tolyl)tri-p-cresol, (12) 4,6-bis(octylthiomethyl )-o-cresol, (13) 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H ,5H)-trione, (14) 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-xy,lyl)methyl]-1,3,5-triazine-2,4 , 6(1H,3H,5H)-trione, (15
  • (1) is preferred as the antibacterial agent A1 used in this embodiment, and (9) is preferred as the antibacterial agent A2. preferable.
  • Antibacterial agent B contained in the antibacterial resin composition of this embodiment has a structure represented by the following chemical formula 2 in its molecule.
  • R is a hydrogen atom, an alkyl group, or an ether group.
  • antioxidants can be used, including (1) bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate, (2 ) poly[ ⁇ 6-(1,1,3,3-tetramethylbutyl)amino-1,3,5-triazine-2,4-diyl ⁇ (2,2,6,6,-tetramethyl-4 -piperidyl)imino ⁇ hexamethylene ⁇ (2,2,6,6-tetramethyl-4-piperidyl)imino ⁇ ], (3) 1,2,3,4-butanetetracarboxylic acid and 2,2,6, Mixed esterified product of 6-tetramethyl-4-piperidinol and 3,9-bis(2-hydroxy-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5]undecane, (4) Tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)-1,2,3,4-butanetetrac
  • the antibacterial agent C contained in the antibacterial resin composition of this embodiment has a structure represented by the following chemical formula 3 in its molecule.
  • known benzotriazole derivatives can be used, including (1) 2-(2H-benzotriazol-2-yl)-4-(1,1, 3,3-tetramethylbutyl)phenol, (2) 2-(2H-benzotriazol-2-yl)-4-methylphenol, (3) 2-(2H-benzotriazol-2-yl)-4,6 -bis(1-methyl-1-phenylethyl)phenol, (4)2-(5-chloro-2H-benzotriazol-2-yl)-6-(1,1-dimethylethyl)-4-methylphenol, (5) 2,2-methylene-bis(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl))phenol, (6) Methyl 3-(3 -(2H-2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl)propionate and PEG300 reaction product, (7) 2-(2H-benzotriazol-2
  • Antibacterial agents A to C Antibacterial agents A and C are thought to exhibit antibacterial properties by denaturing enzyme proteins and inhibiting respiration, and antibacterial agent B is thought to exhibit antibacterial properties by destroying cell membranes and cell walls.
  • antibacterial agent A1 and antibacterial agent B have excellent compatibility with urethane resin, so they are thought to be difficult to precipitate on the surface of urethane resin, antibacterial agent A2 is easy to dissolve in lubricant, and antibacterial agent C is easy to bleed. There is a tendency.
  • antibacterial agent A2 and antibacterial agent C which are easily soluble in urethane resin, precipitate and collect on the surface of urethane resin, resulting in the above-mentioned antibacterial properties against bacteria. it seems to do. Therefore, it is preferable that at least one type of antibacterial agents A1, A2, B, and C is selected and added to the antibacterial resin composition of the present embodiment.
  • the total content of the antibacterial agents A1, A2, B and C in this embodiment is 0.2 to 20 parts by weight, preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the urethane resin. be.
  • the total content of antibacterial agents A1, A2, B and C is less than 0.2 parts by weight, sufficient antibacterial properties cannot be imparted to the antibacterial resin composition. If the total content of antibacterial agents A1, A2, B and C exceeds 20 parts by weight, it is not preferable because the physical properties of the antibacterial resin composition will deteriorate, and each antibacterial agent is more expensive than the resin. This is also unfavorable from a cost standpoint.
  • the content of each of the antibacterial agents A1, A2, B, and C in this embodiment is 0.05 to 5 parts by weight, preferably 0.12 to 2.0 parts by weight, based on 100 parts by weight of the urethane resin. 5 parts by weight.
  • the antibacterial resin composition of this embodiment may be used in a highly concentrated product, that is, in a masterbatch.
  • the total content of antibacterial agents A1, A2, B and C is preferably 1 to 70 parts by weight based on 100 parts by weight of the urethane resin. preferable. If the total content of antibacterial agents A1, A2, B and C is less than 1 part by weight, the dilution rate will be low when diluting with a resin to which no antibacterial agent is added, making it uneconomical.
  • each antibacterial agent may be insufficiently dissolved or dispersed when diluted with a diluent resin.
  • the antibacterial resin composition of the present embodiment is a masterbatch
  • the content of each of the antibacterial agents A1, A2, B, and C is 1 to 30 parts by weight based on 100 parts by weight of the urethane resin. It is more preferable.
  • the antibacterial resin composition of this embodiment may be used by further adding a conventional antibacterial agent.
  • Conventional antibacterial agents are broadly classified into inorganic and organic antibacterial agents. Examples of inorganic antibacterial agents include zeolite, silica gel, glass, calcium phosphate, etc. supported with metal ions such as silver, zinc, copper, etc., and organic antibacterial agents such as alcohol, thiazoline, and imidazole. There are various systems, etc. These conventional antibacterial agents may be used alone or in an appropriate combination of two or more.
  • the antibacterial resin composition of this embodiment may need to be colored, so it may contain a coloring agent as long as it does not impede the purpose of the present disclosure.
  • a coloring agent include organic pigments, inorganic pigments, extender pigments, and dyes. These colorants may be used alone or in an appropriate combination of two or more.
  • additives include flame retardants, ultraviolet absorbers, antioxidants, light stabilizers, antistatic agents, crosslinking agents, different resins, etc., as long as they do not impede the purpose of the present disclosure. can be mentioned. These additives may be used alone or in an appropriate combination of two or more.
  • inorganic, organic, metal, etc. fibrous or plate-like fillers, powdery fillers, etc. may be added. These may be used alone or in an appropriate combination of two or more.
  • the method for producing the antibacterial resin composition of this embodiment is not particularly limited, and known equipment and production methods that are generally used as conventional methods for producing resin compositions can be employed. For example, a predetermined amount of a lubricant, each antibacterial agent, and additives added as needed are mixed into a urethane resin and kneaded.
  • the kneading can be carried out by any physical blending method such as melt kneading, solvent cast blending, latex blending, and polymer complex.
  • kneading examples include a Banbury mixer, a kneader, a kneader-ruder, a single-screw extruder, and a multi-screw extruder.
  • the kneading temperature is not particularly limited, but is usually in the range of 150 to 250°C.
  • the antibacterial resin composition of this embodiment can be obtained. can get.
  • the antibacterial resin composition of this embodiment can be applied to all the applications in which urethane resins are normally used.
  • industrial parts ball joints, rollers, dust covers, packing, gears, hammers, grease covers, hoses, tubes, belt conveyors, handrails, etc.
  • sports and leisure parts sportsnow chains, sports shoes, ski boots, etc.
  • Various containers food containers, cosmetic containers, pharmaceutical containers, etc.
  • automobile parts vehicle interior parts, etc.
  • home appliances air conditioners, jet towels, refrigerators, etc.
  • electrical equipment parts switch buttons, etc.
  • stationery toys, furniture
  • furniture Examples include clothing storage products, etc.) and daily necessities (kitchenware, bath products, etc.).
  • examples include cosmetic containers, pharmaceutical containers, etc., design parts of home appliances, remote controls, switches, switch buttons of electrical equipment parts, handles of stationery such as ballpoint pens, and vehicle interior parts of automobile parts. Suitable for use in areas that are touched by human hands, such as buttons on inside handles and shift knobs, and handrails for escalators.
  • Examples 1 to 3 Comparative Examples 1 to 12> (Preparation of simulated antibacterial urethane resin sheet)
  • the urethane resin was mixed with each component in the proportions shown in Table 1, and kneaded for 2 minutes at 210°C using a small tabletop kneader (Xplore MC15, manufactured by DSM).
  • Antibacterial urethane resin sheets (hereinafter referred to as "resin sheets") of Examples 1 to 3 and Comparative Examples 1 to 12 were produced using Xplore IM12 (manufactured by Kogyo Co., Ltd.).
  • the basic conditions for injection molding were a cylinder temperature of 210° C., a mold temperature of 50° C., and an injection pressure of 7 MPa.
  • Urethane resin Thermoplastic polyether urethane (TPU) (manufactured by BASF, Elastolan 1190ATR)
  • Lubricant Fatty acid amide
  • Antibacterial agent A1 Pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]
  • Antibacterial agent A2 Dibutylhydroxytoluene
  • Antibacterial agent B Bis(2,2,6,6-tetramethyl-4-piperidyl) sebacate
  • Antibacterial agent C 2-(2H-benzotriazol-2-yl)-4-(1 ,1,3,3-tetramethylbutyl)phenol
  • Each of the above antibacterial urethane resin sheets (50 mm x 50 mm) was placed in a sterilized petri dish. 0.4 ml of a preculture solution with an adjusted number of viable bacteria was inoculated onto the sample surface, and the surface was covered with a polyethylene film (40 mm x 40 mm). After culturing at 35° C. for 24 hours, the bacteria were washed out with SCDLP medium, and the number of viable bacteria was determined by the pour plate method. The results are shown in Table 1.
  • a 1/20 (Staphylococcus aureus) diluted Nutrient Pros liquid medium is used for the nutrients in the inoculum solution, and the sample has an antibacterial activity value of 2.0 or more according to the calculation formula specified by JIS compared to a sample without additives.
  • a case of less than 2.0 was judged as "A” (antibacterial property), and a case of less than 2.0 was judged as "B” (no antibacterial property).
  • a material similar to the above-mentioned thermoplastic polyether urethane (TPU) was used as an additive-free sample.
  • TPU thermoplastic polyether urethane
  • Staphylococcus aureus NBRC 12732
  • the resin sheets in Examples 1 to 3 have antibacterial properties because they contain all of the antibacterial agents A1, A2, B, and C.
  • Comparative Example 1 does not have antibacterial properties because no antibacterial agent was added.
  • Comparative Examples 2 to 4, 6, and 7 contain antibacterial agents A to C independently, and therefore do not have antibacterial properties.
  • Comparative Example 5 has antibacterial properties, it does not contain a lubricant and therefore has poor moldability.
  • Comparative Examples 8 to 11 contain two or three types of antibacterial agents, but do not contain all antibacterial agents A1, A2, B, and C, and therefore do not have antibacterial properties.
  • Comparative Example 12 added a silver-based antibacterial agent, but did not have antibacterial properties due to the influence of the lubricant.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Selon la présente invention, une composition de résine antimicrobienne contient une résine d'uréthane, un lubrifiant et, en tant qu'agents antimicrobiens, un dérivé de phénol encombré, un dérivé d'amine encombré et un dérivé de benzotriazole.
PCT/JP2022/045123 2022-03-23 2022-12-07 Composition de résine antimicrobienne WO2023181514A1 (fr)

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JP2022-046574 2022-03-23
JP2022046574 2022-03-23

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WO2023181514A1 true WO2023181514A1 (fr) 2023-09-28

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010505719A (ja) * 2006-09-30 2010-02-25 北京仁▲創▼科技集▲団▼有限公司 複合透水性レンガ及び複合透水性レンガの表面層製造用混合材料
CN108586700A (zh) * 2018-05-15 2018-09-28 浙江华峰热塑性聚氨酯有限公司 不黄变可自愈合热塑性聚氨酯弹性体及其制备方法
CN109320901A (zh) * 2018-10-25 2019-02-12 上海奇彩塑胶原料有限公司 耐候耐磨增强型聚甲醛复合材料及其制备方法
WO2019069802A1 (fr) * 2017-10-05 2019-04-11 三井化学株式会社 Résine de polyuréthanne, article moulé, et procédé de production d'une résine de polyuréthanne
JP6888161B1 (ja) * 2020-10-02 2021-06-16 大日精化工業株式会社 ウレタンプレポリマー、湿気硬化型ウレタンホットメルト樹脂組成物、及び積層体。
JP2022038213A (ja) * 2020-08-26 2022-03-10 日東電工株式会社 部材加工方法
JP2022041901A (ja) * 2020-08-31 2022-03-11 住友化学株式会社 積層体及び表示装置

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010505719A (ja) * 2006-09-30 2010-02-25 北京仁▲創▼科技集▲団▼有限公司 複合透水性レンガ及び複合透水性レンガの表面層製造用混合材料
WO2019069802A1 (fr) * 2017-10-05 2019-04-11 三井化学株式会社 Résine de polyuréthanne, article moulé, et procédé de production d'une résine de polyuréthanne
CN108586700A (zh) * 2018-05-15 2018-09-28 浙江华峰热塑性聚氨酯有限公司 不黄变可自愈合热塑性聚氨酯弹性体及其制备方法
CN109320901A (zh) * 2018-10-25 2019-02-12 上海奇彩塑胶原料有限公司 耐候耐磨增强型聚甲醛复合材料及其制备方法
JP2022038213A (ja) * 2020-08-26 2022-03-10 日東電工株式会社 部材加工方法
JP2022041901A (ja) * 2020-08-31 2022-03-11 住友化学株式会社 積層体及び表示装置
JP6888161B1 (ja) * 2020-10-02 2021-06-16 大日精化工業株式会社 ウレタンプレポリマー、湿気硬化型ウレタンホットメルト樹脂組成物、及び積層体。

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