WO2024142891A1 - Composition d'élastomère thermoplastique, et composition d'élastomère thermoplastique pour bouchon pour réceptacle médical - Google Patents

Composition d'élastomère thermoplastique, et composition d'élastomère thermoplastique pour bouchon pour réceptacle médical Download PDF

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WO2024142891A1
WO2024142891A1 PCT/JP2023/044279 JP2023044279W WO2024142891A1 WO 2024142891 A1 WO2024142891 A1 WO 2024142891A1 JP 2023044279 W JP2023044279 W JP 2023044279W WO 2024142891 A1 WO2024142891 A1 WO 2024142891A1
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mass
polymer
styrene
thermoplastic elastomer
elastomer composition
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PCT/JP2023/044279
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Japanese (ja)
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克匡 上松
悠 松本
憲昭 伊達
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アロン化成株式会社
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  • Patent Document 1 discloses a medical resin composition with improved leakage resistance and resealability, which is composed of (a) a block copolymer and/or a hydrogenated block copolymer consisting of at least two polymer blocks A mainly made of an aromatic vinyl compound having a specified Mw and at least one polymer block B mainly made of a conjugated diene, (b) a hydrogenated petroleum resin and/or a phenylene ether resin, (c) a peroxide decomposition type olefin resin, and (d) a non-aromatic rubber softener.
  • a thermoplastic elastomer composition comprising a styrene-based polymer (A), a softener (B), and an olefin-based polymer (C),
  • the styrene-based polymer (A) includes a polymer (A 1 ) which is a styrene-based block copolymer having a styrene-based polymer block (X 1 ) and a conjugated diene compound polymer block (Y 1 );
  • the conjugated diene compound polymer block (Y 1 ) constituting the polymer (A 1 ) has a ratio of structural units derived from 1,2-vinyl bonds of 50 mass % or more, the styrene-based polymer (A) accounts for 20 to 50 mass%, and the total amount of the styrene-based polymer (A), the softener (B), and the olefin-based polymer (C) is 75 to 99
  • the styrene polymer block (X 1 ) is a polymer block having a styrene monomer unit as a main constituent unit.
  • the styrene monomer unit is a constituent unit having styrene and/or a styrene derivative as a monomer.
  • examples of the styrene derivative include ⁇ -methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 1,3-dimethylstyrene, and p-tert-butylstyrene. These may be used alone or in combination of two or more.
  • the styrene-based polymer block (X 1 ) contains other structural units than the styrene-based monomer units
  • the monomers forming the other structural units are not limited, and examples thereof include acrylonitrile, methacrylic acid esters, etc. These may be used alone or in combination of two or more.
  • examples of the embodiment in which the polymer (A 1 ) is a linear polymer and the styrene polymer block (X 1 ) forms two molecular ends include "X 1 -Y 1 -X 1 ,”"X 1 -Y 1 -X 1 -Y 1 -X 1 ,” and "X 1 -Y 1 -X 1 -Y 1 -X 1 -Y 1 -X 1 ". That is, examples include various polymers commonly known as SBS for non-hydrogenated products and SEBS for hydrogenated products. These may be used alone or in combination of two or more.
  • each X 1 means a styrene-based polymer block (X 1 ) for convenience, and does not mean that each X 1 is the same styrene-based polymer block.
  • each X 1 may be the same or different. The same applies to each Y 1. Furthermore , the styrene-based polymer block (X 1 ) may be the same or different from the styrene-based polymer block (X 2 ) and the styrene-based polymer block (X 3 ) described later.
  • the conjugated diene compound monomer forming the conjugated diene compound polymer block (Y 1 ) contains at least a constituent unit derived from 1,3-butadiene. Furthermore, it is preferable that the conjugated diene compound polymer block (Y 1 ) is a polymer block having a 1,3-butadiene monomer unit as a main constituent unit.
  • the carbon-carbon double bond content can be measured by 1 H-NMR analysis using a nuclear magnetic resonance apparatus (such as INOVA AS600, manufactured by VARIAN).
  • the hydrogenated polymer (A 2 ) can also be called a hydrogenated polymer, a hydrogenated copolymer, a hydrogenated styrene-based polymer, or a hydrogenated styrene-based copolymer.
  • the inclusion of polymer (A 2 ) tends to improve the liquid leakage suppression performance and needle retention performance (needle retention time) compared to when polymer (A 2 ) is not included.
  • needle retention time needle retention time
  • the inclusion of polymer (A 2 ) tends to result in a smaller MFR, a larger tensile strength, a larger elongation at break, and a larger tear strength compared to when polymer (A 2 ) is not included or when it is included in a small amount. Therefore, it is considered that these properties contributed to the improvement.
  • the content ratio of the styrene-based monomer unit is in the above range, suitable flexibility, heat resistance, and mechanical strength can be obtained.
  • the content of the styrene-based monomer unit can be measured in the same manner as described for the polymer (A 1 ).
  • the Mw of the polymer (A 2 ) is not limited, but can be 50,000 to 500,000, further can be 70,000 to 400,000, and further can be 100,000 to 300,000.
  • the Mn of the polymer (A 2 ) is not limited, but can be 40,000 to 500,000, further can be 60,000 to 400,000, and further can be 80,000 to 280,000.
  • the Mw/Mn of the polymer (A 2 ) is not limited, but can be 1.00 to 1.30, further can be 1.03 to 1.17, and further can be 1.06 to 1.12. Within these ranges, a thermoplastic elastomer composition having excellent moldability and heat resistance can be easily obtained. Therefore, it is preferable because it is easy to mold and easy to utilize heating operations in sterilization treatment, etc.
  • the Mw (weight average molecular weight) and Mn (number average molecular weight) of the polymer (A 2 ) can be measured by gel permeation chromatography in the same manner as in the case of the polymer (A 1 ).
  • the polymer (A 2 ) may have a polar functional group such as a carboxyl group, a hydroxyl group, an acid anhydride group, an amino group, an epoxy group, etc. in the molecular chain and/or at the molecular end. These may be used alone or in combination of two or more kinds.
  • the styrene-based polymer block (X 2 ) is a polymer block having a styrene-based monomer unit as a main constituent unit.
  • the styrene-based monomer unit is a constituent unit having styrene and/or a styrene derivative as a monomer.
  • examples of the styrene derivative include ⁇ -methylstyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, 1,3-dimethylstyrene, and p-tert-butylstyrene. These may be used alone or in combination of two or more.
  • the proportion of units derived from styrene is not limited, but can be 50 mass % or more, further 80 mass % or more, further 90 mass % or more, further 95 mass % or more, and usually 100 mass % or less, based on the entire styrene-based polymer block (X 2 ).
  • the polymer (A 2 ) when the polymer (A 2 ) is a linear polymer, the polymer (A 2 ) has the same number of styrene-based polymer blocks (X 2 ) and conjugated diene compound polymer blocks (Y 2 ), or the number of styrene-based polymer blocks (X 2 ) is one more than the number of conjugated diene compound polymer blocks (Y 2 ), so that the styrene-based polymer block (X 2 ) can form at least one molecular end of the polymer (A 2 ).
  • Examples of embodiments in which the number of styrene polymer blocks (X 2 ) is one more than the number of conjugated diene compound polymer blocks (Y 2 ) include a structure "X 2 -Y 2 -X 2 -Y 2 -X 2 " having three styrene polymer blocks (X 2 ) and two conjugated diene compound polymer blocks (Y 2 ) and a structure "X 2 -Y 2 -X 2 -Y 2 -X 2 -Y 2 -X 2 " having four styrene polymer blocks (X 2 ) and three conjugated diene compound polymer blocks (Y 2 ).
  • examples of such polymers include various polymers commonly known as SBS for non-hydrogenated products and SEBS for hydrogenated products. These may be used alone or in combination of two or more. That is, when the styrene polymer block (X 2 ) constitutes at least one molecular end of the polymer (A 2 ), more than half of the blocks constituting the polymer (A 2 ) become the styrene polymer block (X 2 ).
  • each X 2 means a styrene-based polymer block (X 2 ) for convenience, but does not mean that each X 2 is the same styrene-based polymer block. In the polymer (A 2 ), each X 2 may be the same or different.
  • the styrene-based polymer block (X 2 ) may be the same or different from the above-mentioned styrene-based polymer block (X 1 ) and the below-mentioned styrene-based polymer block (X 3 ).
  • the conjugated diene compound polymer block (Y 2 ) is a polymer block having a conjugated diene compound monomer unit as a main constituent unit.
  • the conjugated diene compound monomer unit is a constituent unit having a conjugated diene and/or a conjugated diene derivative as a monomer.
  • examples of the conjugated diene include butadiene (1,3-butadiene, 1,2-butadiene), isoprene (2-methyl-1,3-butadiene), and 1,3-pentadiene. These may be used alone or in combination of two or more.
  • the conjugated diene compound monomer forming the conjugated diene compound polymer block (Y 2 ) contains at least a constituent unit derived from 1,3-butadiene. Furthermore, it is preferable that the conjugated diene compound polymer block (Y 2 ) is a polymer block having a 1,3-butadiene monomer unit as a main constituent unit.
  • the proportion of the conjugated diene compound monomer units constituting the conjugated diene compound polymer block (Y 2 ) is not limited, but can be 50 mass % or more, further 80 mass % or more, further 90 mass % or more, further 95 mass % or more, and usually 100 mass % or less, based on the entire conjugated diene compound polymer block ( Y 2 ).
  • the conjugated diene compound polymer block (Y 2 ) contains other structural units than the conjugated diene compound monomer units
  • the monomers forming the other structural units are not limited, and examples thereof include butylene, isobutylene, pentene, hexene, hexene 5-ethylidene-2-norbornene, 1,4-hexadiene, etc. These may be used alone or in combination of two or more.
  • the conjugated diene compound polymer block (Y 2 ) contains 1,3-butadiene monomer units derived from 1,3-butadiene.
  • the 1,3-butadiene monomer units may be 1,2-vinyl bonded units [i.e., -CH 2 -CH(CH ⁇ CH 2 )-] or 1,4-vinyl bonded units (including cis-1,4-bonds and trans-1,4-bonds) [i.e., -CH 2 -CH ⁇ CH-CH 2 -].
  • the ratio of the structural units derived from 1,2-vinyl bonds in the conjugated diene compound polymer block (Y 2 ) may be less than 50% by mass when the total units derived from 1,3-butadiene monomer are taken as 100% by mass, but is preferably 47% by mass or less, more preferably 43% by mass or less, even more preferably 38% by mass or less, and particularly preferably 35% by mass or less.
  • the lower limit is not limited and can be 0% by mass or more, for example, 5% by mass or more, 10% by mass or more, 15% by mass or more, or 20% by mass or more.
  • the polymer (A 3 ) is a block copolymer having a styrene-based polymer block (X 3 ) and a conjugated diene-based compound polymer block (Y 3 ). From the viewpoint of having the styrene-based polymer block (X 3 ), the polymer (A 3 ) can also be called a styrene-based polymer (A 3 ).
  • This polymer (A 3 ) may be a non-hydrogenated product, but is preferably a hydrogenated product from the viewpoint of heat resistance and mechanical strength. That is, it is preferably a hydrogenated styrene-based polymer.
  • the Mw of the polymer (A 3 ) is not limited, but can be 50,000 to 500,000, further 100,000 to 450,000, and further 200,000 to 350,000.
  • the Mn of the polymer (A 3 ) is not limited, but can be 40,000 to 500,000, further 80,000 to 450,000, and further 160,000 to 350,000.
  • the Mw/Mn of the polymer (A 3 ) is not limited, but can be 1.00 to 1.60, further 1.02 to 1.40, and further 1.05 to 1.30. Within these ranges, a thermoplastic elastomer composition having excellent moldability and heat resistance can be easily obtained. Therefore, it is preferable because it is easy to mold and easy to utilize heating operations in sterilization treatment and the like.
  • the Mw (mass average molecular weight) and Mn (number average molecular weight) of the polymer (A 3 ) can be measured by gel permeation chromatography in the same manner as in the case of the polymer (A 1 ).
  • the conjugated diene compound polymer block (Y 3 ) contains 1,3-butadiene monomer units derived from 1,3-butadiene.
  • the 1,3-butadiene monomer units may be 1,2-vinyl bonded units [i.e., -CH 2 -CH(CH ⁇ CH 2 )-] or 1,4-vinyl bonded units (including cis-1,4-bonds and trans-1,4-bonds) [i.e., -CH 2 -CH ⁇ CH-CH 2 -].
  • This content ratio can be 22% by mass or more, 25% by mass or more, 28% by mass or more, or 30% by mass or more. On the other hand, this content ratio can be 78% by mass or less, 75% by mass or less, 72% by mass or less, or 70% by mass.
  • the upper and lower limits mentioned above can be combinations of each other, for example, 22 to 78% by mass, 22 to 75% by mass, 25 to 75% by mass, 25 to 72% by mass, 28 to 72% by mass, 28 to 70% by mass, or 30 to 70% by mass. In each of the above ranges, there is a tendency for the leakage suppression performance to improve as the range narrows.
  • thermoplastic elastomer composition of the present invention contains the styrene-based polymer (A), the softener (B), and the olefin-based polymer (C). Among them, the styrene-based polymer (A) is as described above.
  • thermoplastic elastomer composition of the present invention contains a softener (B).
  • the softener (B) By containing the softener (B), the thermoplastic elastomer composition of the present invention can be softened and the moldability and elongation at break can be improved. This can provide a liquid leakage effect.
  • the type of the softener (B) is not limited, and mineral oil-based softeners, synthetic oil-based softeners, etc. may be used. These may be used alone or in combination of two or more kinds.
  • examples of the mineral oil-based softener include paraffinic oil (paraffin process oil, etc.), naphthenic oil (naphthenic process oil, etc.), liquid paraffin, mineral oil, white oil, etc. These may be used alone or in combination of two or more kinds.
  • the MFR (melt mass flow rate) of the olefin polymer (C) is not limited, but can be 0.5 to 30 g/10 min, and can also be 1 to 15 g/10 min. In this range, it is easy to obtain a thermoplastic elastomer composition with excellent moldability. Note that this MFR is a value at 230°C and a load of 21.2 N according to ASTM D1238.
  • thermoplastic elastomer composition of the present invention may contain other components in addition to the above-mentioned styrene polymer (A), softener (B) and olefin polymer (C).
  • other components include fillers, thermoplastic polymers other than the styrene polymer (A) and olefin polymer (C), colorants, pigments, antistatic agents, antibacterial agents, antifungal materials, flame retardants, flame retardant assistants, antioxidants, heat stabilizers, antiaging agents, light stabilizers, ultraviolet absorbers, antifogging agents, antiblocking agents, dispersants, lubricants, and other various additives. Any of these may be used alone or in combination. These may be used alone or in combination of two or more.
  • D50 is determined by measuring particle size distribution using a laser diffraction/scattering particle size distribution analyzer, and is measured as the particle size at 50% of the cumulative volume from the small particle size side.
  • a wet laser diffraction/scattering particle size distribution analyzer that can be used is the "SALD-200VER” model manufactured by Shimadzu Corporation.
  • the upper and lower limits can be any combination of the above, for example, 1 to 80 parts by mass, 2 to 80 parts by mass, 2 to 70 parts by mass, 5 to 70 parts by mass, 5 to 60 parts by mass, 7 to 60 parts by mass, 7 to 50 parts by mass, and 10 to 50 parts by mass.
  • styrene-based polymers (E) may be included. Furthermore, as the other styrene-based polymers (E), ⁇ -methylstyrene polymers and/or styrene- ⁇ -methylstyrene copolymers are preferred.
  • the proportion of ⁇ -methylstyrene-based monomer units is not limited, but is preferably 10% by mass or more, more preferably 20% by mass or more, even more preferably 30% by mass or more, particularly preferably 40% by mass or more, and especially preferably 50% by mass or more, relative to 100% by mass of the entire styrene- ⁇ -methylstyrene copolymer.
  • the other styrene-based polymer (E) has a lower molecular weight than the styrene-based polymer (A).
  • the styrene-based polymer may have an Mw of 1,000 to 30,000 and an Mn of 800 to 20,000, with the Mw being greater than the Mn.
  • the inclusion of such other styrene-based polymer (E) improves the moldability and elongation at break of the thermoplastic elastomer composition of the present invention, and improves the effect of suppressing liquid leakage.
  • These other styrene-based polymers can be referred to as tackifiers.
  • the softening point of the other styrene-based polymer (E) is not limited, but may be, for example, 80 to 200°C, or 90 to 180°C, or 100 to 160°C, as measured by ASTM E28.
  • the inclusion of such other styrene-based polymer (E) has the effect of improving the heat resistance of the thermoplastic elastomer composition of the present invention.
  • Such other styrene-based polymers (E) include, for example, the Crystallex (trade name) series manufactured by Eastman Chemical Company, the Endex (trade name) series manufactured by Eastman Chemical Company, the FTR (trade name) series manufactured by Mitsui Chemicals, Inc., the FMR (trade name) series manufactured by Mitsui Chemicals, Inc., Legit (trade name) manufactured by Sanyo Chemical Industries, Ltd., and Arfon (trade name) manufactured by Toagosei Co., Ltd.
  • styrene-based polymers (E) When other styrene-based polymers (E) are included, their content is not limited, and can be, for example, 0.1 to 50 parts by mass when the total amount of the styrene-based polymers (A) is 100 parts by mass. In this range, the effect of suppressing liquid leakage and needle retention can be improved.
  • the lower limit of the content of other styrene-based polymers (E) can be 0.5 parts by mass or more, further 1.0 parts by mass or more, further 1.5 parts by mass or more, and further 2.0 parts by mass or more.
  • the upper limit can be 45 parts by mass or less, further 35 parts by mass or less, further 25 parts by mass or less, and further 15 parts by mass or less.
  • the above upper and lower limit values can be each combination, for example, 0.5 to 45 parts by mass, further 1.0 to 35 parts by mass, 1.5 to 25 parts by mass, and 2.0 to 15 parts by mass.
  • thermoplastic elastomer composition of the present invention are not limited, but the A hardness is preferably 60 or less from the viewpoint of suppressing needle puncture resistance, and 10 or more from the viewpoint of obtaining high needle retention performance. This value can further be 10 to 50, 11 to 40, 12 to 38, 13 to 36, or 14 to 34. This A hardness is a value measured by the method of measurement in the examples described below.
  • the tensile strength of the thermoplastic elastomer composition of the present invention can be 1.0 to 15 MPa, 1.2 to 12 MPa, 1.5 to 7.0 MPa, 2.0 to 6.0 MPa, or 2.5 to 5.5 MPa. This tensile strength is a value measured by the method of measurement in the examples described below.
  • the breaking elongation of the thermoplastic elastomer composition of the present invention can be 500 to 1500%, 550 to 1300%, 600 to 1100%, 650 to 1000%, or 700 to 930%. This breaking elongation is a value measured by the method described in the examples below.
  • the tear strength of the thermoplastic elastomer composition of the present invention can be 5.0 to 30 MPa, 5.5 to 20 MPa, 6.0 to 17 MPa, 6.5 to 15 MPa, or 7.0 to 12.5 MPa. This tear strength is a value measured by the method of measurement in the examples described below.
  • thermoplastic elastomer composition of the present invention may be produced in any manner, and the process is not limited.
  • the composition may be produced by mixing the styrene polymer (A), the softener (B), the olefin polymer (C), and other components as required, using various types of heated kneaders, such as a single-screw extruder, a twin-screw extruder, a roll, a Banbury mixer, a Brabender, or a kneader.
  • the drug stopper of each infusion soft bag was set so that the exposed surface of the stopper was parallel to the horizontal surface of the test stand, and a 500g weight was attached to the medical metal needle, and the weight was set so as to hang down perpendicularly below the exposed surface of the stopper.
  • the liquid flow path of the medical metal needle was sealed during the test to prevent liquid leakage from the medical metal needle.
  • the test was performed indoors at a temperature of 23°C and a humidity of 50%. The time from the above insertion until the medical metal needle fell out was measured and recorded as the needle retention time (unit: "seconds"). The results are shown in Tables 1 to 3.
  • the content (mass%) of the polymer (A1) is in accordance with composition condition 3, and in the thermoplastic elastomer composition of the present invention, the content (mass%) is more than 20 mass% and 80 mass% or less.
  • Examples 1 to 5 are examples in which composition condition 1 is satisfied using polymer (A 1 ) and polymer (A 2 ), composition condition 2 is satisfied using a filler or other styrene-based polymer (E), and composition condition 3 is satisfied using a softener and an olefin-based polymer, and the liquid leakage suppression effect and needle retention performance are also good.
  • Comparative Example 1 which does not use polymer (A 1 ) and does not satisfy composition conditions 1 and 3, had poor liquid leakage suppression effect and needle retention performance.
  • Comparative Example 7 the affinity with the softener and olefin-based resin was insufficient, so a measurement sample could not be molded.
  • Comparative Example 2 which uses polymer (A 1 ) and polymer (A 2 ) but does not satisfy composition condition 2, had poor liquid leakage suppression effect and needle retention performance.
  • Example 6 is an example in which polymer ( A3 ) was used instead of polymer ( A2 ) in Example 2, and the liquid leakage suppression effect and needle retention performance were good.
  • Comparative Example 3 in which composition condition 2 was 100% by mass and Comparative Example 6 in which composition condition 2 was 62% by mass showed a liquid leakage rate of 100% and poor needle retention performance.
  • Comparative Examples 4 and 5 are compositions in which the softener component of Examples 2 and 6 is reduced, and do not satisfy composition condition 1. Since the A hardness is high, the needle retention performance is excellent, but the liquid leakage rate reaches 100%.
  • Examples 7 and 8 are examples in which polymer (A 3 ) was further used in comparison with Example 4, and compared with Example 4, the liquid leakage suppression effect was equivalent, and the needle retention performance was also superior.
  • Comparative Examples 9 and 10 are examples in which composition condition 3 was 20% by mass and 10% by mass, respectively, and did not satisfy the condition. Compared with Examples 7 and 8, the liquid leakage suppression effect was significantly reduced, and the needle retention performance was also inferior. In addition, Comparative Examples 11 and 12 satisfied composition conditions 1 and 3, but composition condition 2 was 100%, and compared with Examples 7 and 8, the liquid leakage suppression effect and needle retention performance were inferior.
  • thermoplastic elastomer composition of the present invention has excellent leakage prevention properties and needle retention performance, and can be particularly suitably used for stoppers of drug stoppers for medical containers that are involved in needle insertion operations.
  • thermoplastic elastomer composition of the present invention may be used for any purpose, but can be widely used in various medical products. That is, for example, it is suitable for use in stoppers for medical containers, various connecting tubes for infusion sets, etc.

Abstract

La composition d'élastomère thermoplastique de l'invention contient un polymère à base de styrène (A), un amollissant (B) et un polymère à base d'oléfine (C). (A) inclut un polymère （Ａ１） qui possède une séquence polymère à base de styrène（Ｘ１） et une séquence polymère de composé à base de diène conjugué （Ｙ１）. （Ｙ１）configurant （Ａ１） présente une proportion de liaison １，２－vinyle supérieure ou égale à 50% en masse. 20 à 50% en masse de (A) est contenu dans l'ensemble de la composition. Le total de (A), (B) et (C) est compris entre ７５ et ９９% en masse. Lorsque (A) représente 100% en masse, （Ａ１）représente plus de ２０% en masse et ８０% en masse ou moins.
PCT/JP2023/044279 2022-12-28 2023-12-11 Composition d'élastomère thermoplastique, et composition d'élastomère thermoplastique pour bouchon pour réceptacle médical WO2024142891A1 (fr)

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JP2022-212131 2022-12-28

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