Plasticizers and plastic products

A biodegradable plasticizer with a unique molecular structure enhances the properties of plastics like polylactic acid, improving durability and flexibility while accelerating decomposition, addressing the limitations of traditional additives and environmental concerns.

JP7796474B2Active Publication Date: 2026-01-09LARGAN MEDICAL CO LTD
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Patent Information

Application Number
JP2020194313
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2019-11-25
Filing Date
2020-11-24
Publication Date
2026-01-09
Estimated Expiration
2040-11-24

AI Technical Summary

Technical Problem

Biodegradable plastics like polylactic acid suffer from insufficient durability, heat resistance, impact resistance, flexibility, and airtightness, and have slow decomposition rates in general environments, limiting their applications and posing environmental risks.

Method used

Development of a biodegradable plasticizer with a specific molecular structure comprising amino acids, carboxyl groups, and branched structures with controlled carbon atom ratios, which can be grafted onto plastics to enhance texture, durability, and accelerate decomposition.

Benefits of technology

The plasticizer improves the properties of biodegradable plastics, making them durable, heat-resistant, flexible, and safe for the environment, while accelerating their decomposition, thus addressing the limitations of traditional additives.

✦ Generated by Eureka AI based on patent content.

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Patent Text Reader

Abstract

To provide a plasticizer.SOLUTION: A plasticizer having biodegradability, a molecule 100 of the plasticizer comprises: a central structure 110 comprising at least one benzene derivative and at least one amino acid; at least two connecting structures comprising a first connecting structure which is an amine functional group 121 that is connected to the center structure 110 and a second connecting structure which is a carboxylic acid functional group bonded to the center structure; and at least one branch structure 130 having a plurality of carbons and connected to at least one of the first and second connecting structures. Thus, with high biodegradability as an object, a plasticizer with high durability, heat resistance, impact resistance, flexibility, which is harmless to the human body and hard to release and has low cost is designed.SELECTED DRAWING: Figure 1
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Description

[Technical Field]

[0001] The present disclosure relates to plastic material additives, and in particular to biodegradable plasticizers. [Background technology]

[0002] To address environmental issues caused by plastic products, biodegradable plastics are currently being developed, such as polylactic acid (PLA), poly(butylene succinate) (PBS), and 1,4-butanediol adipate / 1,4-butanediol terephthalate copolymer (poly(butylene adipate-co-terephthalate) (PBAT)). However, the properties of these plastics are inferior to those of petrochemical plastics. For example, while polylactic acid has excellent rigidity and transparency, its durability, heat resistance, impact resistance, flexibility, and airtightness are insufficient, resulting in many limitations in its applications. Summary of the Invention [Problem to be solved by the invention]

[0003] In order to improve the properties, texture, and cost of biodegradable plastics, traditional degradable additives can be added to change the flexibility and durability of biodegradable plastics, but the effect of traditional additives in improving the properties of biodegradable plastics is still insufficient, and they are prone to release and costly, so traditional additives still have room for improvement. In addition, the decomposition conditions for biodegradable plastics are strict. For example, polylactic acid plastic products can be completely decomposed into carbon dioxide and water under certain environmental conditions and for a sufficient amount of time, and can be circulated into the natural environment without causing any harm, but it is very difficult to completely decompose polylactic acid plastic products naturally in a general environment. Therefore, the development of additives that can accelerate the decomposition rate and help biodegradable plastics to quickly decompose and enter the natural environment will become an important trend in the future. [Means for solving the problem]

[0004] According to the present disclosure, there is provided a biodegradable plasticizer, the plasticizer molecule comprising: a central structure including at least one amino acid, defined as a first linking structure, and a central structure including at least one amino acid, the central structure including at least one carboxyl group, defined as a second linking structure; and at least two branched structures having a plurality of carbon atoms, one of which is bonded to the first linking structure and the other of which is bonded to the second linking structure, the one of which is bonded to the amino group to form an amide bond, and the other of which is bonded to the carboxyl group to form an ester bond; The branched structure does not contain aromatic compounds, The present invention provides a plasticizer in which, where nNC is the number of carbon atoms in a branched structure that bond to an amino group and nOC is the number of carbon atoms in a branched structure that bond to a carboxy group, nNC and nOC for all of the branched structures satisfy the condition 0.20≦nNC / (nNC+nOC)≦0.80, where nNC and nOC are each zero or a positive integer, and nNC and nOC are not simultaneously zero. The number of carbon atoms in each of at least two branched structures is 5 to 20. Alternatively, according to the present disclosure, there is provided a biodegradable plasticizer, wherein the molecule of the plasticizer comprises a central structure including at least one amino acid, the central structure including at least one amino acid, and the second linking structure including at least one carboxyl group, the first linking structure being defined as a first linking structure, and at least two branched structures having a plurality of carbon atoms, the at least two branched structures being each bonded to the second linking structure and each bonded to the carboxyl group to form an ester bond. and the branched structure does not contain aromatic compounds. Provided is a plasticizer, wherein each of the at least two branched structures has 5 to 10 carbon atoms.

[0005] By researching and developing innovative molecular structures, we have developed a branched structure with multiple carbon atoms, which has a first linking structure (amino group or hydroxy group) and a second linking structure (carboxy group), and which has a benzene derivative and / or amino acid as the central structure. ConstructionWe have developed a biodegradable plasticizer that can be grafted onto the outside of plastics, improving their texture, making them suitable for a wide range of applications, and further accelerating their decomposition cycle. Furthermore, with the goal of achieving high biodegradability, we have designed a plasticizer that is durable, heat-resistant, impact-resistant, and flexible, yet is harmless to the human body, difficult to release, and inexpensive.

[0006] According to the present disclosure, there is provided a biodegradable plastic product comprising the above-mentioned plasticizer and a polyester plastic, wherein the polyester plastic is polylactic acid, polybutylene succinate, (1,4-butanediol adipate / 1,4-butanediol terephthalate) copolymer, or polyhydroxyalkanoate, and the plasticizer is mixed into the polyester plastic.

[0007] According to the present disclosure, there is provided another biodegradable plasticizer, wherein the molecule of the plasticizer contains at least one hydroxy group defined as a first linking structure and at least one carboxy group defined as a second linking structure, and the molecule comprises at least two benzene derivatives defined as a central structure and being 2-hydroxybenzoic acid, and branched structures having multiple carbon atoms, which are bonded to the benzene derivatives via the hydroxy group and the carboxy group of each benzene derivative and form ester bonds when bonded to the carboxy groups. The branched structure does not contain aromatic compounds, and the branched structure is bonded to the carboxyl group of the benzene derivative. Other plasticizers are provided. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 1 is a schematic diagram of a plasticizer molecular structure according to a first embodiment of the present disclosure. [Figure 2] FIG. 2 is a schematic diagram of a plasticizer molecular structure according to a second embodiment of the present disclosure. [Figure 3] FIG. 10 is a schematic diagram of a plasticizer molecular structure according to a third embodiment of the present disclosure. [Figure 4] FIG. 10 is a schematic diagram of a plasticizer molecular structure according to a fourth embodiment of the present disclosure. [Figure 5] FIG. 10 is a schematic diagram of a plasticizer molecular structure according to a fifth embodiment of the present disclosure. [Figure 6] FIG. 10 is a schematic diagram of a plasticizer molecular structure according to a sixth embodiment of the present disclosure. [Figure 7] FIG. 10 is a schematic diagram of a plasticizer molecular structure according to a seventh embodiment of the present disclosure. [Figure 8] FIG. 13 is a schematic diagram of a plasticizer molecular structure according to an eighth embodiment of the present disclosure. [Figure 9] FIG. 13 is a schematic diagram of a plasticizer molecular structure according to a ninth embodiment of the present disclosure. [Figure 10] FIG. 22 is a schematic diagram of a plasticizer molecular structure according to a tenth embodiment of the present disclosure. [Figure 11] FIG. 22 is a schematic diagram of a plasticizer molecular structure according to an eleventh embodiment of the present disclosure. [Figure 12] FIG. 22 is a schematic diagram of a plasticizer molecular structure according to a twelfth embodiment of the present disclosure. [Figure 13] FIG. 22 is a schematic diagram of a plasticizer molecular structure according to a thirteenth embodiment of the present disclosure. [Figure 14] FIG. 22 is a schematic diagram of a plasticizer molecular structure according to a fourteenth embodiment of the present disclosure. [Figure 15] FIG. 10 is a graph showing the results of biodegradation tests for the Comparative Example, the 29th Example, and the 30th Example. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present disclosure discloses a biodegradable plasticizer, the molecule of which comprises a central structure (amino acid or benzene derivative, hereinafter the same), at least two linking structures (amino group and carboxy group, or hydroxy group and carboxy group, hereinafter the same), and at least one branched structure. Construction The at least two linking structures are each connected to the core structure, and the branching structure is connected to at least one of the at least two linking structures. (Note that in this specification, "connect" is used as a synonym for "couple.")

[0010] The core structure includes at least one of a benzene derivative and at least one amino acid, where the benzene derivative helps maintain the biodegradability of the plasticizer, and the amino acid can be catabolized by living cells and helps improve the biodegradability of the plasticizer. Alternatively, the core structure may be a benzene derivative and further include an amino acid. Furthermore, the core structure may be an amino acid and include at least two amino acids, where the amino acid residues may be acidic, basic, hydrophilic, or hydrophobic, helping to adjust the properties of the plasticizer according to the nature of the amino acid residues.

[0011] The benzene derivative may be a compound having a similar structure, such as 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-hydroxybenzoic acid, 3-hydroxybenzoic acid, or 4-hydroxybenzoic acid.

[0012] Amino acids may be standard amino acids, essential amino acids that the human body cannot synthesize, modified amino acids (e.g., hydroxyproline, hydroxylysine, or thyroxine), or other non-standard amino acids (e.g., homocysteine, homoserine, or ornithine). The standard and essential amino acids are summarized in Table 1.

[0013] [Table 1]

[0014] The core structure may be glycerin (i.e., glycerol, propane-1,2,3-triol) or 2-(2-hydroxyethoxy)propan-1-ol.

[0015] The at least two connecting structures include a first connecting structure and a second connecting structure, and the first connecting structure is a mesh. of The second linking structure is a carboxyl group. Kishi It is a carboxyl group.

[0016] When the central structure is a benzene derivative, the amine in the benzene derivative of Group and Carbo Kishi The positions of the groups can be adjacent (ortho) or non-adjacent (meta or para).

[0017] Nettle of The group may be a functional group such as -NH2, -NHR, or -NR2. of The group may be a primary amine, a secondary amine, a tertiary amine, or a quaternary ammonium cation. of The hydroxyl group can be substituted from the hydroxyl group, and when the branched structure is connected to a hydroxyl group, the connection site can be decomposed by hydrolysis, which helps to improve the biodegradability of the plasticizer.

[0018] When the plasticizer molecule contains two linking structures, they are the first linking structure and the second linking structure, respectively. Alternatively, the plasticizer molecule may contain three linking structures, which are the first linking structure, the second linking structure, and the third linking structure, respectively. The third linking structure may be an amino acid residue, for example, the amino acid of a lysine residue. ofThe third linking structure may be a carboxyl functional group of the aspartic acid residue, or the third linking structure may be a carboxyl functional group of the aspartic acid residue. The plasticizer molecule may also include four linking structures, which are the first linking structure, the second linking structure, the third linking structure, and the fourth linking structure, respectively, and the third linking structure and the fourth linking structure are diamines of the arginine residue. of The functional groups may be the same or different, such as a group, etc. Furthermore, when the core structure contains multiple amino acids, the plasticizer molecule may have five or more linking structures.

[0019] The branched structure is a branch having multiple carbon atoms, and the number of carbon atoms in the branched structure may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, etc. Furthermore, the branched structure may have oxygen to form an ether functional group, and the number of oxygen atoms in the branched structure may be 1, 2, 3, 4, 5, 6, or 7, etc.

[0020] The branched structure may be a saturated fatty acid, the number of carbon atoms of which may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, or 36, such as acetic acid (lipid number C2:0), butyric acid (C4:0), caproic acid (C6:0), caprylic acid (C8:0), capric acid (C10:0), lauric acid (C12:0), lignoceric acid (C24:0), or hexatriacontylic acid (C36:0).

[0021] The branched structure may be an unsaturated fatty acid, which may have 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms and 1, 2, 3, 4, 5, or 6 double bonds, such as eicosenoic acid (paullinic acid, C20:1), eicosatrienoic acid (DGLA, C20:3), docosahexaenoic acid (DHA, C22:6), or tetradecenoic acid (C24:1).

[0022] The branched structure can be formed by sequential polymerization of ethylene glycol (ethylene glycol), polyethylene glycol (PEG), propylene glycol (propylene glycol), or polypropylene glycol (PPG) selected as the monomer. Furthermore, the monomer of the branched structure may be selected from the group consisting of ethylene glycol, polyethylene glycol, propylene glycol, and polypropylene glycol and polymerized. The branched structure formed by polymerization of the above-mentioned monomers can control the required molecular weight of the plasticizer and appropriately adjust the hydrophilicity and hydrophobicity of the plasticizer, thereby optimizing the properties of the plasticizer and improving the compatibility of the plasticizer when mixed with plastics.

[0023] The branched structures are connected to at least one of the first linking structure and the second linking structure, i.e., the core structure may be connected to the branched structures via the first linking structure and / or the second linking structure by methods such as esterification, dehydration, or peptidation.

[0024] The branched structure is of When the branched structure is connected to a carboxylic acid group, it forms an amide bond, which helps to improve the efficiency of the plasticizer to be degraded by enzymes, and further improves the biodegradability of the plasticizer. KishiWhen the branched structure is connected to a hydroxy group, it forms an ester bond. Furthermore, when the branched structure is connected to a hydroxy group, it forms an ether bond, and the ether bond can be decomposed by hydrolysis in certain environments, which helps to improve the biodegradability of the plasticizer.

[0025] The plasticizer may further include at least one polar functional group connected to the branched structure, and the polar functional group may be located in the middle or at the end of the branched structure. The polar functional group may also be a carboxyl group (-COOH), Hydroxy Group (-OH), amine of The plasticizer may have a polar functional group (-NH2) or a phosphate group (-PO(OH)2) as needed, and may have a carboxyl group, etc., to improve the hydrophilicity of the plasticizer and the affinity between the plasticizer and the plastic, and to facilitate mixing of the plasticizer with the plastic. Hydroxy Motoi, Ami of The carboxylic acid may contain at least two polar functional groups selected from the group consisting of a carboxylic acid group and a phosphate group.

[0026] Branched structure mesh of The number of carbon atoms connected to the group is nNC, and the branched structure Kishi The number of carbon atoms connected to the group is nOC, and satisfies the condition 0≦nNC / (nNC+nOC)≦1.00, where nNC and nOC are each zero or a positive integer, and nNC and nOC are not simultaneously zero. Furthermore, the following conditions may be satisfied: 0.01≦nNC / (nNC+nOC), nNC / (nNC+nOC)≦1.00, 0.05≦nNC / (nNC+nOC)≦0.95, 0.10≦nNC / (nNC+nOC)≦0.90, 0.15≦nNC / (nNC+nOC)≦0.80, 0.20≦nNC / (nNC+nOC)≦0.70, 0.25≦nNC / (nNC+nOC)≦0.60, 0.30≦nNC / (nNC+nOC)≦0.50, or 0.35≦nNC / (nNC+nOC)≦0.40.

[0027] Branched structure mesh of The number of oxygen atoms connected to the group is nNO, and the branched structure is KishiThe number of oxygen atoms connected to the hydroxyl group in the branched structure is nO'C, and the number of oxygen atoms connected to the hydroxyl group in the branched structure is nO'O. of The branched structures nOC, nOO, nO'C and nO'O are calculated from atoms other than the nitrogen atom of the group. Kishi nNC, nNO, nOC, nOO, nO'C, and nO'O do not include carbon or oxygen atoms of polar functional groups. nO'C is considered to be nOC in calculations, and nO'O is considered to be nOO in calculations.

[0028] The molecular weight of the plasticizer is MwP, 45 0≦ The larger the molecular weight of the plasticizer, the more difficult it is to pass through the cell membrane, which helps to prevent the plasticizer from directly passing through the cell membrane and entering the cell. Furthermore, MwP≦200 0、 47 5≦ MwP≦100 0、 50 0≦ MwP, 52 5≦ MwP, 55 0≦ MwP, or 60 0≦ MwP≦150 0 and The condition can be met.

[0029] The above-mentioned technical features of the plasticizer of the present disclosure can be combined and arranged to achieve corresponding effects.

[0030] The present disclosure also discloses another biodegradable plasticizer, the molecule of which comprises at least two core structures, at least two linking structures, and a branching structure. Each core structure is connected to at least one linking structure, and each linking structure is connected to a branching structure, i.e., all of the core structures are connected to the same branching structure. The detailed characteristics of the core structure, linking structure, and branching structure are the same as those of the plasticizer described above, and will not be repeated here.

[0031] The present disclosure also provides a biodegradable plastic product. The plastic product includes the above-described plasticizer and a polyester plastic (polyester resin). The polyester plastic may be polylactic acid, polybutylene succinate, 1,4-butanediol adipate / 1,4-butanediol terephthalate copolymer, or polyhydroxyalkanoate (PHA). The plasticizer is mixed into the polyester plastic. By selecting the type of polyester plastic, it is possible to ensure a highly compatible mixture of the plasticizer with the plastic, which helps improve the ductility of the plastic and reduce the possibility of plasticizer release. Furthermore, the polyhydroxyalkanoate may be polyhydroxybutyrate (PHB).

[0032] First Embodiment

[0033] Please refer to Figure 1, which is a structural schematic diagram of a plasticizer molecule 100 according to a first embodiment of the present disclosure. As can be seen from Figure 1, the plasticizer molecule 100 of the first embodiment includes a core structure 110, two linking structures, and a branched structure 130.

[0034] The core structure 110 is a benzene derivative.

[0035] The two connecting structures are the first connecting structure and the second connecting structure, respectively, and are connected to the central structure 110. The first connecting structure is a mesh. of Group 121, and the second linking structure is a carbo Kishi group (not shown).

[0036] The branched structure 130 is formed by polymerization of ethylene glycol or polyethylene glycol monomers and is bonded to the second linking structure and forms an ester bond 122'.

[0037] Second Embodiment

[0038] Please refer to Figure 2, which is a structural schematic diagram of a plasticizer molecule 200 according to a second embodiment of the present disclosure. As can be seen from Figure 2, the plasticizer molecule 200 of the second embodiment includes a central structure 210, two linking structures, a branched structure 230, and a polar functional group 260.

[0039] The core structure 210 is a benzene derivative.

[0040] The two connecting structures are the first connecting structure and the second connecting structure, respectively, and are connected to the central structure 210. The first connecting structure is a mesh. of Group 221, and the second linking structure is a carbo Kishi group (not shown).

[0041] The branched structure 230 is formed by polymerization of propylene glycol or polypropylene glycol monomers and is attached to the second linking structure and forms an ester bond 222'.

[0042] Polar functional groups 260 are attached to the branched structures 230 .

[0043] <Third embodiment>

[0044] Please refer to Figure 3, which is a structural schematic diagram of a plasticizer molecule 300 according to a third embodiment of the present disclosure. As can be seen from Figure 3, the plasticizer molecule 300 of the third embodiment includes a core structure 310, two linking structures and a branched structure 330.

[0045] The core structure 310 is a benzene derivative.

[0046] The two connecting structures are the first connecting structure and the second connecting structure, respectively, and are connected to the central structure 310. The first connecting structure is a mesh. of Group 321, and the second linking structure is a carbo Kishi group (not shown).

[0047] The branched structure 330 is formed by bonding a first short chain 331 and a second short chain 332, where the first short chain 331 is formed by polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 332 is formed by polymerization of propylene glycol or polypropylene glycol. The branched structure 330 is bonded to the second linking structure, forming an ester bond 322′.

[0048] <Fourth embodiment>

[0049] Please refer to Figure 4, which is a structural schematic diagram of a plasticizer molecule 400 according to a fourth embodiment of the present disclosure. As can be seen from Figure 4, the plasticizer molecule 400 of the fourth embodiment includes a core structure 410, two linking structures and a branched structure 430.

[0050] The core structure 410 is a benzene derivative.

[0051] The two connecting structures are the first connecting structure and the second connecting structure, respectively, and are connected to the central structure 410. The first connecting structure is a mesh. of group (not shown), and the second linking structure is a carboxyl group. Kishi It is base 422.

[0052] The branched structure 430 is a fatty acid and is attached to the first linking structure to form an amide bond 421'.

[0053] Fifth Embodiment

[0054] Please refer to Figure 5, which is a structural schematic diagram of a plasticizer molecule 500 according to a fifth embodiment of the present disclosure. As can be seen from Figure 5, the plasticizer molecule 500 of the fifth embodiment includes a central structure 510, two linking structures, two branched structures 530 and 540, and a polar functional group 560.

[0055] The core structure 510 is a benzene derivative.

[0056] The two connecting structures are a first connecting structure and a second connecting structure, and are respectively connected to the central structure 510. The first connecting structure is a mesh. of group (not shown), and the second linking structure is a carboxyl group. Kishi group (not shown).

[0057] The branched structure 530 is formed by bonding a first short chain 531 and a second short chain 532, the first short chain 531 being formed by polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 532 being formed by polymerization of propylene glycol or polypropylene glycol monomers, and the branched structure 530 is bonded to the second linking structure and forms an ester bond 522′.

[0058] The branched structure 540 is a fatty acid and is attached to the first linking structure and forms an amide bond 521'.

[0059] Polar functional groups 560 are attached to branched structures 530 .

[0060] Sixth Embodiment

[0061] Please refer to Figure 6, which is a structural schematic diagram of a plasticizer molecule 600 according to a sixth embodiment of the present disclosure. As can be seen from Figure 6, the plasticizer molecule 600 of the sixth embodiment includes a central structure 610, two linking structures, a branched structure 630, and a polar functional group 660.

[0062] The core structure 610 is an amino acid and includes residue 611 .

[0063] The two connecting structures are the first connecting structure and the second connecting structure, respectively, and are connected to the central structure 610. The first connecting structure is a mesh. of The second linking structure is a carbon atom. Kishi group (not shown).

[0064] The branched structure 630 is formed by polymerization of ethylene glycol or polyethylene glycol monomers and is bonded to a second linking structure and forms an ester bond 622'.

[0065] A polar functional group 660 is attached to the branched structure 630 .

[0066] Seventh Embodiment

[0067] Please refer to Fig. 7, which is a structural schematic diagram of a plasticizer molecule 700 according to a seventh embodiment of the present disclosure. As can be seen from Fig. 7, the plasticizer molecule 700 of the seventh embodiment includes a core structure 710, two linking structures and a branched structure 730.

[0068] The core structure 710 is an amino acid and includes residue 711 .

[0069] The two connecting structures are a first connecting structure and a second connecting structure, respectively, and are connected to the central structure 710. The first connecting structure is a mesh. of Group 721, and the second linking structure is a carbo Kishi group (not shown).

[0070] The branched structure 730 is formed by polymerization of propylene glycol or polypropylene glycol monomers and is bonded to a second linking structure and forms an ester bond 722'.

[0071] Eighth Embodiment

[0072] Please refer to Figure 8, which is a structural schematic diagram of a plasticizer molecule 800 according to an eighth embodiment of the present disclosure. As can be seen from Figure 8, the plasticizer molecule 800 of the eighth embodiment includes a core structure 810, two linking structures and a branched structure 830.

[0073] Core structure 810 is an amino acid and includes residue 811 .

[0074] The two connecting structures are a first connecting structure and a second connecting structure, respectively, and are connected to the central structure 810. The first connecting structure is a mesh. of The second linking structure is a carbon atom. Kishi group (not shown).

[0075] The branched structure 830 is formed by bonding a first short chain 831 and a second short chain 832, where the first short chain 831 is formed by polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 832 is formed by polymerization of propylene glycol or polypropylene glycol monomers, and the branched structure 830 is bonded to the second linking structure and forms an ester bond 822′.

[0076] Ninth Embodiment

[0077] Please refer to Figure 9, which is a structural schematic diagram of a plasticizer molecule 900 according to a ninth embodiment of the present disclosure. As can be seen from Figure 9, the plasticizer molecule 900 of the ninth embodiment includes a core structure 910, two linking structures and a branched structure 930.

[0078] Core structure 910 is an amino acid and includes residue 911.

[0079] The two connecting structures are a first connecting structure and a second connecting structure, respectively, and are connected to the central structure 910. The first connecting structure is a mesh. of group (not shown), and the second linking structure is a carboxyl group. Kishi It is base 922.

[0080] The branched structure 930 is a fatty acid and is attached to the first linking structure and forms an amide bond 921'.

[0081] Tenth Embodiment

[0082] Please refer to Figure 10, which is a structural schematic diagram of a plasticizer molecule 1000 according to a tenth embodiment of the present disclosure. As can be seen from Figure 10, the plasticizer molecule 1000 of the tenth embodiment includes a central structure 1010, two linking structures, two branched structures 1030 and 1040, and a polar functional group 1060.

[0083] The core structure 1010 is an amino acid and includes residue 1011.

[0084] The two connecting structures are a first connecting structure and a second connecting structure, respectively, and are connected to the central structure 1010. The first connecting structure is a mesh. of group (not shown), and the second linking structure is a carboxyl group. Kishi group (not shown).

[0085] The branched structure 1030 is formed by bonding a first short chain 1031 and a second short chain 1032, where the first short chain 1031 is formed by polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 1032 is formed by polymerization of propylene glycol or polypropylene glycol monomers, and the branched structure 1030 is bonded to the second linking structure and forms an ester bond 1022'.

[0086] The branching structure 1040 is a fatty acid and is attached to the first linking structure and forms an amide bond 1021'.

[0087] A polar functional group 1060 is attached to the branched structure 1030 .

[0088] Eleventh Embodiment

[0089] Please refer to Figure 11, which is a structural schematic diagram of a plasticizer molecule 1100 according to an eleventh embodiment of the present disclosure. As can be seen from Figure 11, the plasticizer molecule 1100 of the eleventh embodiment includes a central structure 1110, three linking structures, three branched structures 1130, 1140, and 1150, and a polar functional group 1160.

[0090] Core structure 1110 contains two amino acids, and each amino acid contains residues 1111 and 1112, respectively.

[0091] The three connecting structures are the first connecting structure, the second connecting structure, and the third connecting structure, and are respectively connected to the central structure 1110. The first connecting structure is a mesh. of group (not shown), and the second linking structure and the third linking structure are each a carbon atom. Kishi A third linking structure is attached to residue 1111.

[0092] Branched structure 1130 is formed by polymerization of ethylene glycol or polyethylene glycol monomers and is bonded to a second linking structure and forms an ester bond 1122'.

[0093] The branching structure 1140 is a fatty acid and is attached to the first linking structure and forms an amide bond 1121'.

[0094] The branched structure 1150 is formed by the bonding of a first short chain 1151 and a second short chain 1152, where the first short chain 1151 is formed by the polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 1152 is formed by the polymerization of propylene glycol or polypropylene glycol monomers, and the branched structure 1150 is bonded to a third linking structure and forms an ester bond 1123'.

[0095] A polar functional group 1160 is attached to the branched structure 1150 .

[0096] <Twelfth embodiment>

[0097] Please refer to Figure 12, which is a structural schematic diagram of a plasticizer molecule 1200 according to a twelfth embodiment of the present disclosure. As can be seen from Figure 12, the plasticizer molecule 1200 of the twelfth embodiment includes a core structure 1210, three linking structures, and three branched structures 1230, 1240, and 1250.

[0098] Core structure 1210 contains two amino acids, each of which contains residues 1211 and 1212, respectively.

[0099] The three connecting structures are respectively a first connecting structure, a second connecting structure, and a third connecting structure, and are respectively connected to the central structure 1210. The first connecting structure and the third connecting structure are respectively mesh-shaped. of group (not shown), and the second linking structure is a carboxyl group. Kishi A third linking structure is attached to residue 1212.

[0100] Branched structure 1230 is formed by polymerization of ethylene glycol or polyethylene glycol monomers and is bonded to a second linking structure and forms an ester bond 1222'.

[0101] The branching structure 1240 is a fatty acid and is attached to the first linking structure and forms an amide bond 1221'.

[0102] Branching structure 1250 is a fatty acid, which is attached to a third linking structure and forms an amide bond 1223'.

[0103] <Thirteenth embodiment>

[0104] Please refer to Figure 13, which is a structural schematic diagram of a plasticizer molecule 1300 according to a thirteenth embodiment of the present disclosure. As can be seen from Figure 13, the plasticizer molecule 1300 of the thirteenth embodiment includes a central structure 1310, four linking structures, three branched structures 1330, 1340, and 1350, and a polar functional group 1360.

[0105] Core structure 1310 comprises three amino acids, each of which comprises residues 1311, 1312, and 1313, respectively.

[0106] The four connecting structures are the first connecting structure, the second connecting structure, the third connecting structure, and the fourth connecting structure, and are respectively connected to the central structure 1310. The first connecting structure is a mesh. ofThe second linking structure and the third linking structure are each a carbon atom. Kishi The fourth linking structure is an amino group (not shown). of The third and fourth linking structures are attached to residues 1311 and 1313, respectively.

[0107] Branched structure 1330 is formed by polymerization of ethylene glycol or polyethylene glycol monomers and is bonded to a second linking structure and forms an ester bond 1322'.

[0108] The branched structure 1340 is formed by the bonding of a first short chain 1341 and a second short chain 1342, where the first short chain 1341 is formed by the polymerization of ethylene glycol or polyethylene glycol monomers, and the second short chain 1342 is formed by the polymerization of propylene glycol or polypropylene glycol monomers, and the branched structure 1340 is bonded to a third linking structure and forms an ester bond 1323′.

[0109] Branching structure 1350 is a fatty acid, which is attached to a fourth linking structure and forms an amide bond 1324'.

[0110] A polar functional group 1360 is attached to the branched structure 1330 .

[0111] <Fourteenth embodiment>

[0112] Please refer to Figure 14, which is a structural schematic diagram of a plasticizer molecule 1400 according to a fourteenth embodiment of the present disclosure. As can be seen from Figure 14, the plasticizer molecule 1400 of the fourteenth embodiment includes two core structures 1410a and 1410b, two linking structures, a branched structure 1430, and two polar functional groups 1460a and 1460b.

[0113] Each of the core structures 1410a, 1410b is a benzene derivative.

[0114] Each of the central structures 1410a, 1410b is connected to a corresponding linking structure, i.e., the central structure 1410a is connected to one of the linking structures, and the central structure 1410b is connected to the other linking structure. Kishi group (not shown).

[0115] Branched structure 1430 is formed by polymerization of ethylene glycol or polyethylene glycol monomers. Each core structure 1410a, 1410b is connected to branched structure 1430 by a linking structure, forming an ester bond 1420a, 1420b, respectively.

[0116] Each polar functional group 1460a, 1460b is bonded to a corresponding core structure 1410a, 1410b, respectively.

[0117] According to the above embodiment, a detailed description will be given below with specific examples.

[0118] In the first to eighth embodiments, of base, carbo Kishi The branched structures connected to the hydroxyl group and the hydroxyl group are numbered as SCA, SCC, and SCH, respectively, and the plasticizer molecule may contain multiple branched structures connected to the same functional group. For example, the first embodiment is an amino group. of When a group includes two branched structures connected to the group, the two branched structures are numbered as SCA1 and SCA2, respectively, and the numbering system for the other branched structures is the same and will not be repeated here.

[0119] [Table 2-1]

[0120] [Table 2-2]

[0121] [Table 2-3]

[0122] In the first to eighth embodiments, nNC SCA1 and nNO SCA1 represent the carbon number and oxygen number of the branched structure SCA1, respectively, and nNC SCA2 and nNO SCA2 represent the carbon number and oxygen number of the branched structure SCA2, respectively, and nOC SCC and nOO SCC represents the carbon number and oxygen number of the branched structure SCC. SCAl, SCAl and SC C are used only as markings to more clearly understand the meaning they represent, and do not affect the calculation of the carbon number and oxygen number in the claims for values ​​such as nNO, nNC, nOC and nOO, i.e., nNC SCA1 is considered to be nNC, and nNO SCA1 is considered to be nNO and nNC SCA2 is considered to be nNC, and nNO SCA2 is nNO and nOC SCC nOC and nOO SCC is set to nOO. The notation method in the table below is the same, so it will not be explained again.

[0123] [Table 3-1]

[0124] [Table 3-2]

[0125] [Table 3-3]

[0126] [Table 3-4]

[0127] [Table 4-1]

[0128] Table 4-2

[0129] Table 4-3

[0130] Table 5-1

[0131] Table 5-2

[0132] Table 5-3

[0133] Table 6-1

[0134] Table 6-2

[0135] Table 6-3

[0136] Table 6-4

[0137] Table 6-5

[0138] Table 6-6

[0139] Table 6-7

[0140] Table 6-8

[0141] Table 6-9

[0142] Table 7-1

[0143] Table 7-2

[0144] Table 7-3

[0145] Table 7-4

[0146] Table 7-5

[0147] Table 7-6

[0148] Table 7-7

[0149] Table 7-8

[0150] Table 7-9

[0151] Table 8-1

[0152] Table 8-2

[0153] Table 8-3

[0154] Table 8-4

[0155] Table 8-5

[0156] Table 8-6

[0157] Table 8-7

[0158] Table 8-8

[0159] Table 8-9

[0160] Table 9-1

[0161] Table 9-2

[0162] Table 9-3

[0163] Table 9-4

[0164] Table 9-5

[0165] Table 9-6

[0166] Table 9-7

[0167] Table 9-8

[0168] Table 9-9

[0169] Table 10-1

[0170] Table 10-2

[0171] Table 10-3

[0172] Table 10-4

[0173] Table 10-5

[0174] Table 10-6

[0175] Table 10-7

[0176] Table 10-8

[0177] Table 10-9

[0178] Table 11-1

[0179] Table 11-2

[0180] Table 11-3

[0181] Table 11-4

[0182] Table 11-5

[0183] Table 11-6

[0184] Table 11-7

[0185] Table 11-8

[0186] Table 11-9

[0187] Table 12-1

[0188] Table 12-2

[0189] Table 12-3

[0190] Table 12-4

[0191] Table 12-5

[0192] Table 12-6

[0193] Table 12-7

[0194] Table 12-8

[0195] Table 12-9

[0196] Table 13-1

[0197] Table 13-2

[0198] Table 13-3

[0199] Table 13-4

[0200] Table 13-5

[0201] Table 13-6

[0202] Table 13-7

[0203] Table 13-8

[0204] Table 13-9

[0205] Table 14-1

[0206] Table 14-2

[0207] Table 14-3

[0208] Table 14-4

[0209] Table 14-5

[0210] [Table 14-6]

[0211] [Table 14-7]

[0212] [Table 14-8]

[0213] [Table 14-9]

[0214] Please refer to Figure 15, which shows the results of the biodegradation test for the Comparative Example, Examples 29 and 30. Below, a biodegradation test (ASTM 5338) was conducted on plasticizers with different molecular structures, and the test subjects were the Comparative Example, Examples 29 and 30. The biodegradation rate (degree of degradation) of the test subjects over different days is shown in the table below.

[0215] [Table 15-1]

[0216] [Table 15-2]

[0217] [Table 15-3]

[0218] The present disclosure has developed a biodegradable plasticizer by researching and developing an innovative molecular structure, which has a first linking structure and a second linking structure, and which has a benzene derivative and / or amino acid as its central structure, with multi-carbon branched structures grafted to the outside. This improves the texture of plastics, makes it suitable for a wide range of applications, and further promotes the decomposition cycle. The plasticizer may contain polar functional groups to adjust the hydrophilicity and hydrophobicity of the plasticizer. Furthermore, with the goal of high biodegradability, the company has designed a plasticizer that has sufficient durability, heat resistance, impact resistance, and flexibility, is harmless to the human body, is difficult to release, and is low-cost.

[0219] Although the embodiments of the present disclosure have been disclosed as above, they are not intended to limit the present disclosure, and anyone skilled in the art can make various changes and modifications without departing from the spirit and scope of the present disclosure. Therefore, the scope of protection of the present disclosure is determined based on the content specified in the claims. [Explanation of symbols]

[0220] 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400: Molecule, 110, 210, 310, 410, 510, 610, 710, 810, 910, 1010, 1110, 1210, 1310, 1410a, 1410b: central structure, 611, 711, 811, 911, 1011, 1111, 1112, 1211, 1212, 1311, 1312, 1313: residue, 121, 221, 321, 621, 721, 821, 1321: Ami of basis, 421', 521', 921', 1021', 1121', 1221', 1223', 1324': amide bond, 422, 922: Carbo Kishi basis, 122', 222', 322', 522', 622', 722', 822', 1022', 1122', 1123', 1222', 1322', 1323', 1420a, 1420b: ester bond, 130, 230, 330, 430, 530, 540, 630, 730, 830, 930, 1030, 1040, 1130, 1140, 1150, 1230, 1240, 1250, 1330, 1340, 1350, 1430: Branched structure, 331, 531, 831, 1031, 1151, 1341: first short chain, 332, 532, 832, 1032, 1152, 1342: second short chain, 260, 560, 660, 1060, 1160, 1360, 1460a, 1460b: polar functional group.

Claims

1. A biodegradable plasticizer, the molecules of which are a core structure containing at least one amino acid, the core structure containing at least an amino group containing at least one amino acid defined as a first linking structure, and a carboxy group containing at least one amino acid defined as a second linking structure; at least two branched structures having multiple carbon atoms; Equipped with one of the at least two branched structures is bound to the first linking structure, the other of the at least two branched structures is bound to the second linking structure, one of the branched structures is bound to the amino group to form an amide bond, and the other of the branched structures is bound to the carboxy group to form an ester bond; The branched structure does not contain an aromatic compound, When the number of carbon atoms in the branched structure that is bonded to the amino group is nNC and the number of carbon atoms in the branched structure that is bonded to the carboxy group is nOC, For all of the branched structures, nNC and nOC satisfy the condition 0.20≦nNC / (nNC+nOC)≦0.80; nNC and nOC are zero or a positive integer, and nNC and nOC are not zero at the same time; A plasticizer in which the at least two branched structures each have 5 to 20 carbon atoms.

2. When the number of carbon atoms in the branched structure connected to the amino group is nNC and the number of carbon atoms in the branched structure connected to the carboxy group is nOC, The plasticizer according to claim 1, wherein nNC and nOC satisfy the condition 0.25≦nNC / (nNC+nOC)≦0.

60.

3. When the number of carbon atoms at which the branched structure is connected to the amino acid is nNC and the number of carbon atoms at which the branched structure is connected to the carboxy group is nOC, The plasticizer according to claim 2, wherein nNC and nOC satisfy the condition 0.30≦nNC / (nNC+nOC)≦0.

50.

4. The molecular weight of the plasticizer is MwP, The plasticizer according to claim 1, wherein MwP satisfies the condition 475≦MwP≦1000.

5. The plasticizer of claim 4, wherein the residue of the amino acid is acidic.

6. The plasticizer according to claim 5, wherein the amino acid is aspartic acid.

7. The plasticizer of claim 4 , wherein the core structure comprises at least two of the amino acids.

8. A biodegradable plasticizer, the molecules of which are a core structure containing at least one amino acid, the core structure containing at least an amino group containing at least one amino acid defined as a first linking structure, and a carboxy group containing at least one amino acid defined as a second linking structure; at least two branched structures having multiple carbon atoms; Equipped with the at least two branched structures are each bonded to the second linking structure and each bonded to the carboxy group to form an ester bond; The branched structure does not contain an aromatic compound, A plasticizer in which the at least two branched structures each have 5 to 10 carbon atoms.

9. The molecular weight of the plasticizer is MwP, The plasticizer according to claim 1, wherein MwP satisfies the condition 450≦MwP.

10. 2. The plasticizer of claim 1, further comprising at least one polar functional group attached to the branched structure, the polar functional group being a carboxy group, a hydroxy group, an amino group, or a phosphate group.

11. The plasticizer of claim 10, comprising at least two polar functional groups selected from the group consisting of a carboxy group, a hydroxy group, an amino group, and a phosphate group.

12. A biodegradable plastic product, The plasticizer of claim 1; a polyester plastic which is polylactic acid, polybutylene succinate, (1,4-butanediol adipate / 1,4-butanediol terephthalate) copolymer, or polyhydroxyalkanoate; Including, A plastic product in which the plasticizer is mixed with the polyester plastic.

13. A biodegradable plasticizer, the molecules of which are at least two benzene derivatives each containing at least one hydroxy group defined as a first linking structure and at least one carboxy group defined as a second linking structure, each of which is defined as a core structure and is 2-hydroxybenzoic acid; a branched structure having a plurality of carbon atoms, which is bonded to each of the benzene derivatives via the hydroxyl group and the carboxyl group of each of the benzene derivatives, and which forms an ester bond when bonded to each of the carboxyl groups; Equipped with A plasticizer in which the branched structure does not contain an aromatic compound and the branched structure binds to the carboxy group of the benzene derivative.

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