Novel polycarbonate-based polymer capable of controlling biodegradation rate by various methods including biodegradation off-on, and application thereof

Abstract

The present disclosure relates to a novel polycarbonate-based polymer capable of controlling the biodegradation rate by various methods including biodegradation OFF-ON, and an application thereof. The polycarbonate-based polymer according to an embodiment of the present disclosure can be applied as a drug carrier, a moisture superabsorbent biodegradable material, an environmentally friendly biodegradable material, and the like. Additionally, the hydrophobic polycarbonate-based polymer according to an embodiment of the present disclosure can block (OFF) the biodegradation of a biodegradable material with a hydrolysis mechanism until a desired time point and trigger (ON) the biodegradation at a desired time point, so that the biodegradable OFF-ON material containing the hydrophobic polycarbonate-based polymer can be applied to drug delivery, biodegradable medical devices for human transplantation, biodegradable devices for environmental monitoring, bioplastics, transient electronics, and the like.

Description

Novel polycarbonate polymers capable of controlling biodegradation rates through various methods including biodegradation off-on and their applications

[0001] The present disclosure relates to a novel polycarbonate polymer capable of controlling the biodegradation rate by various methods including biodegradation off-on and its applications.

[0002] Biodegradable materials are being applied not only in the pharmaceutical field, but also in various fields such as packaging materials, automotive parts, electrical and electronic components, and construction materials. Among biodegradable materials, the annual production of bioplastics is expected to increase nearly threefold, from 2.22 million tons in 2022 to 6.3 million tons in 2028. In particular, polylactide (PLA) and polyhydroxyalkanoate (PHA) polymers, which are biodegradable bioplastics vulnerable to hydrolysis and used for human or environmental protection, are expected to account for 24.6% of the market in 2022 and nearly half, 46.8%, in 2028. Recently, with the global environmental pollution issue emerging, research on biodegradable materials has become increasingly active.

[0003] These biodegradable materials need to extend their biodegradation for a desired period by blocking biodegradation until the point where degradation is necessary. Most biodegradable materials currently in use utilize hydrolysis as their biodegradation mechanism, which can extend their service life by blocking moisture infiltration. However, current methods for inhibiting moisture infiltration, such as metal thin-film coating, are non-biodegradable, creating a contradiction between the biodegradable material and the means to extend its life. Furthermore, while modifying the chemical properties of biodegradable materials is a means of extending their lifespan, this approach can only control the rate of biodegradation, making it difficult to control the timing of biodegradation.

[0004] [Prior Art Literature]

[0005] [Patent Document]

[0006] (Patent Document 0001) Republic of Korea Patent No. 10-0994150 (May 13, 2004)

[0007] The main purpose of the present disclosure is to provide a novel polycarbonate polymer having a structure and a biodegradable off-on material capable of controlling the biodegradation time using the same.

[0008] In order to achieve the above purpose, the present disclosure provides a polycarbonate polymer comprising a repeating unit represented by the following chemical formula 1, wherein the polycarbonate polymer is R by artificial stimulation. 1 A novel polycarbonate polymer is provided, wherein the hydroxyl group is recovered by detachment.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1, R 1 A chain-like (C3-C40) alkyl group; a branched (C3-C40) alkyl group; a (C3-C40) cycloalkyl group; a (C3-C40) heterocycloalkyl group; a (C3-C40) alkenyl group; a (C3-C40) alkynyl group; a (C1-C40) heteroalkyl group; a (C6-C40) aryl group; a (C3-C40) heteroaryl group; a (C6-C40) aryl (C1-C40) alkyl group; a (C2-C40) alkyl (C6-C40) aryl group; -Si(R 2 )(R 3 )(R 4 ) silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 acyl group; or -S(=O)2R 9 may be sulfonic acid; R 2 Inland R 4 are each independently hydrogen, (C1-C40)alkyl group or (C6-C40)aryl group, and R 2 Inland R4 At least one of them may be a (C1-C40) alkyl group or a (C6-C40) aryl group, and R 5 Inland R 9 may each independently be a (C1-C40)alkyl group, a (C3-C40)alkenyl group, a (C3-C40)alkynyl group, a (C3-C40)cycloalkyl group, a (C3-C40)heterocycloalkyl group, a (C6-C40)aryl group, a (C3-C40)heteroaryl group, a (C6-C40)aryl(C1-C40)alkyl group, a (C1-C40)alkyl(C6-C40)aryl group, or a substituent derived from a hydrophilic polymer, and * represents a bonding site.

[0012] The polycarbonate polymer according to an example of the present disclosure may be a hydrophobic polycarbonate polymer.

[0013] According to an example of the present disclosure, the polycarbonate polymer is a hydrolysis-resistant polycarbonate polymer, and R 1 This chain-like (C3-C40) alkyl group; branched (C3-C40) alkyl group; (C3-C40) cycloalkyl group; (C3-C40) heterocycloalkyl group; (C3-C40) alkenyl group; (C3-C40) alkynyl group; (C1-C40) heteroalkyl group; (C6-C40) aryl group; (C3-C40) heteroaryl group; (C6-C40) aryl (C1-C40) alkyl group; or (C2-C40) alkyl (C6-C40) aryl group.

[0014] The R according to an example of the present disclosure 1 A chain-like (C3-C20) alkyl group; a branched (C3-C20) alkyl group; a (C3-C20) cycloalkyl group; a (C3-C20) heterocycloalkyl group; a (C1-C20) alkoxy (C1-C20) alkyl group; a (C3-C20) alkenyl group; -Si(R 2 )(R 3 )(R 4 ) silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 acyl group; or -S(=O)2R9 may be sulfonic acid; R 2 Inland R 4 Each of can be independently a (C1-C20) alkyl group or a (C6-C20) aryl group, and R 5 Inland R 9 may each independently be a (C1-C20)alkyl group, a (C3-C20)alkenyl group, a (C3-C20)alkynyl group, a (C3-C20)cycloalkyl group, a (C3-C20)heterocycloalkyl group, a (C6-C20)aryl group, a (C3-C20)heteroaryl group, a (C6-C20)aryl(C1-C20)alkyl group, or a (C1-C20)alkyl(C6-C20)aryl group.

[0015] The R according to an example of the present disclosure 5 Inland R 9 Each may be independently any one selected from the group consisting of a (C1-C20) alkyl group, a (C3-C20) cycloalkyl group, a (C3-C20) heterocycloalkyl group, a substituent represented by the following chemical formula 3, and a substituent represented by the following chemical formula 4.

[0016] [Chemical Formula 3]

[0017]

[0018] [Chemical Formula 4]

[0019]

[0020] R 11 Inland R 13 may each independently be a (C1-C7) alkyl group, and a to c may each independently be an integer selected from 0 to 3.

[0021] According to an example of the present disclosure, the hydrophobic polycarbonate polymer may be grafted with a hydrophilic brush.

[0022] The hydrophilic brush according to an example of the present disclosure comprises a (C1-200)alkyl(C4-10)heteroalkylsulfobetaine containing a zwitterion, a (C1-200)alkyl((C4-10)heteroalkylsulfobetaine)2, a branched (C2-200)alkyl(C4-10)heteroalkylsulfobetaine, a (C1-200)alkyl(C4-10)heteroalkylcarboxybetaine, a (C1-200)alkyl((C4-10)heteroalkylcarboxybetaine)2, a branched (C2-200)alkyl(C4-10)heteroalkylcarboxybetaine, a (C1-200)alkyl(C4-10)heteroalkylphosphobetaine, (C1-200)alkyl((C4-10)heteroalkylcarphosphobetaine)2, branched (C2-200)alkyl(C4-10)heteroalkylphosphobetaine, or a combination thereof.

[0023] The number average molecular weight (M) of the hydrophobic polycarbonate polymer according to an example of the present disclosure n ) can be from 10,000 to 1,000,000 g / mol.

[0024] The melting point of the hydrophobic polycarbonate polymer according to an example of the present disclosure may be 43 to 50°C.

[0025] According to an example of the present disclosure, the polycarbonate polymer is a hydrophilic polycarbonate polymer, and R in the chemical formula 1 1 Silver -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 acyl group; or -S(=O)2R 9 It can be a sulfonyl group, and R 5 Inland R 9 Each of may independently be a substituent derived from a hydrophilic polymer.

[0026] According to an example of the present disclosure, the hydrophilic polymer is (CH2CH2O) 1-40 Ethylene glycol; ((CH2CH2O) 1-40 )2-Diethylene glycol; branched (CH2CH2O) 1-40Ethylene glycol; (C1-40) alkyl (C4-10) heteroalkyl sulfobetaine; (C1-40) alkyl ((C4-10) heteroalkyl sulfobetaine)2; branched (C1-40) alkyl (C4-10) heteroalkyl sulfobetaine; (C1-40) alkyl (C4-10) heteroalkyl carboxybetaine; (C1-40) alkyl ((C4-10) heteroalkyl carboxybetaine)2; branched (C1-40) alkyl (C4-10) heteroalkyl carboxybetaine; (C1-40) alkyl ((C4-10) heteroalkyl phosphobetaine; (C1-40) alkyl ((C4-10) heteroalkyl phosphobetaine)2; Branched (C1-40) alkyl (C4-10) heteroalkyl phosphobetaine; (CH2COH) 1~40 Vinyl alcohol; ((CH2COH) 1~40 )2-Divinyl alcohol; branched (CH2COH) 1~40 Vinyl alcohol; (CH2COOH) 1-40 Acrylic acid; ((CH2COOH) 1-40 )2-Diacrylic acid; branched (CH2COOH) 1-40 Acrylic acid; (CH2COOM) 1-40 Acrylate; ((CH2COOM) 1-40 )2 diacrylate; branched (CH2COOM) 1-40 Acrylic acid salt; (CH2C(CH3)(C(=O0H)) 1-40 Methacrylic acid; ((CH2C(CH3)(C(=O0H)) 1-40 )2-dimethacrylic acid; branched (CH2C(CH3)(C(=O0H)) 1-40 Methacrylic acid; (CH2C(CH3)(C(=O0M)) 1-40 Methacrylate; ((CH2C(CH3)(C(=O0M)) 1-40 )2-dimethacrylate; branched (CH2C(CH3)(C(=O0M)) 1-40 Methacrylate; (CH2C(CH3)(C(=O)OH)) 1-40 2-propylacrylic acid; ((CH2C(CH3)(C(=O)OH)) 1-40 )2-di-2-propylacrylic acid; branched (CH2C(CH3)(C(=O)OH)) 1-40 2-propylacrylic acid; (CH2C(CH3)(C(=O)OM)) 1-402-propyl acrylate; (((CH2C(CH3)(C(=O)OM)) 1-40 )2di2-propyl acrylate; branched (CH2C(CH3)(C(=O)OM)) 1-40 2-propyl acrylate; (CH2CH(C(=O)NH2) 1-40 Acrylamide; ((CH2CH(C(=O)NH2) 1-40 )2 diacrylamide; branched (CH2CH(C(=O)NH2) 1-40 Acrylamide; (CH2CH(C(=O)NH(CH(CH3)2))) 1-40 N-isopropylacrylamide; ((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )2-diN-isopropylacrylamide; branched (CH2CH(C(=O)NH(CH(CH3)2))) 1-40 N-isopropylacrylamide; (CH2CH(C(=ONHCH2CH2OH))) 1-40 Hydroxyethylmethacrylamide; ((CH2CH(C(=ONHCH2CH2OH))) 1-40 )2-dihydroxyethylmethacrylamide; branched (CH2CH(C(=ONHCH2CH2OH))) 1-40 Hydroxyethylmethacrylamide; (CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 2-Hydroxypropylmethacrylamide; ((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40) Di-2-hydroxypropylmethacrylamide; branched (CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 2-Hydroxypropylmethacrylamide; (CH2C(-OSO3M)) 1-40 Vinyl sulfate salt; ((CH2C(-OSO3M)) 1-40 )2-divinyl sulfate salt; branched (CH2C(-OSO3M)) 1-40 Vinyl sulfate salt; (CH2-4-C6H6SO3H) 1-40 4-styrenesulfonic acid; ((CH2-4-C6H6SO3H) 1-40 )2-di-4-styrenesulfonic acid; branched (CH2-4-C6H6SO3H) 1-404-styrenesulfonic acid; (CH2-4-C6H6SO3NH4) 1-40 4-Styrenesulfonate ammonium salt; ((CH2-4-C6H6SO3NH4) 1-40 )2di4-styrenesulfonate ammonium salt; branched (CH2-4-C6H6SO3NH4) 1-40 4-styrenesulfonate ammonium salt; (CH2C6H6SO3M) 1-40 4-styrenesulfonate salt; ((CH2C6H6SO3M) 1-40 )2di-4-styrenesulfonate salt; branched (CH2C6H6SO3M) 1-40 4-styrenesulfonate salt; (CHCH2NH2) 1-40 Alkylamine; ((CHCH2NH2) 1-40 )2-dialkylamine; branched (CHCH2NH2) 1-40 Alkylamine; (CHCH2NH2·HCl) 1-40 Alkylamine hydrochloride; ((CHCH2NH2·HCl) 1-40 )2-Dialkylamine hydrochloride; branched (CHCH2NH2·HCl) 1-40 Alkylamine hydrochloride; (CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 Ethyleneimine; ((CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )2-diethyleneimine; (CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 Ethyleneimine hydrochloride; ((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )2-Diethyleneimine hydrochloride; (CH2SO3M) 1-40 Vinyl sulfonate; ((CH2SO3M) 1-40 )2-Divinylsulfonate; branched (CH2SO3M) 1-40 Vinyl sulfonate; (CH2CHC(=O)NH2)) 1-40 Acrylamide; ((CH2CHC(=O)NH2))1-40 )2 diacrylamide; branched (CH2CHC(=O)NH2)) 1-40 Acrylamide (CH2CH(C(=O)NHCH(CH3)2)) 1-40 N-isopropylacrylamide; ((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )2-diN-isopropylacrylamide; branched (CH2CH(C(=O)NHCH(CH3)2)) 1-40 N-isopropylacrylamide; (CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Tetramethylpyrrolidium chloride; ((CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )2-ditetramethylpyrrolidium chloride; branched (CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Tetramethylpyrrolidium chloride; SiH2(CH2CH2O) 1-40 Silyl ethylene glycol; branched SiH2((CH2CH2O) 1-40 )silylethylene glycol; SiH((CH2CH2O) 1-40 )2-silyldi(ethylene glycol); Si((CH2CH2O) 1-40 )3-silyltri(ethylene glycol); SiH2(CH2COH) 1~40 Silyl vinyl alcohol; branched SiH2O(CH2COH) 1~40 Silyl vinyl alcohol; SiH((CH2COH) 1~40 )2-silyldi(vinyl alcohol); Si((CH2COH) 1~40 )3-silyltri(vinyl alcohol); SiH2(CH2COOH) 1-40 Silyl acrylate; branched SiH2(CH2COOH) 1-40 Silyl acrylate; SiH((CH2COOH) 1-40 )2-silyldi(acrylic acid); Si((CH2COOH) 1-40 )2-silyltri(acrylic acid); SiH2(CH2COOM) 1-40Silyl acrylate; branched SiH2(CH2COOM) 1-40 Silyl acrylate; SiH((CH2COOM) 1-40 )2-silyldi(acrylate); Si((CH2COOM) 1-40 )3-silyltri(acrylate); SiH2(CH2C(CH3)(C(=O0H)) 1-40 Silylmethacrylic acid; branched SiH2(CH2C(CH3)(C(=O0H)) 1-40 Silylmethacrylic acid; SiH((CH2C(CH3)(C(=O0H)) 1-40 )2-silyldi(methacrylic acid); Si((CH2C(CH3)(C(=O0H)) 1-40 )3-silyltri(methacrylic acid); SiH2(CH2C(CH3)(C(=O0M)) 1-40 Silyl methacrylate; branched SiH2(CH2C(CH3)(C(=O0M)) 1-40 Silyl methacrylate; SiH((CH2C(CH3)(C(=O0M)) 1-40 )2-silyldi(methacrylate); Si((CH2C(CH3)(C(=O0M)) 1-40 )3-silyltri(methacrylate); SiH2(CH2C(CH3)(C(=O)OH)) 1-40 Silyl-2-propylacrylic acid; branched SiH2(CH2C(CH3)(C(=O)OH)) 1-40 Silyl-2-propylacrylic acid; SiH((CH2C(CH3)(C(=O)OH)) 1-40 )2-silyldi(2-propylacrylic acid); Si((CH2C(CH3)(C(=O)OH)) 1-40 )3-silyltri(2-propylacrylic acid); SiH2(CH2C(CH3)(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; branched SiH2(CH2C(CH3)(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; SiH(((CH2C(CH3)(C(=O)OM)) 1-40) )2-silyldi(2-propylacrylate); Si(((CH2C(CH3)(C(=O)OM)) 1-40) )2-silyltri(2-propylacrylate); SiH2(CH2CH(C(=O)NH2) 1-40Silyl acrylamide; branched SiH2(CH2CH(C(=O)NH2) 1-40 Silyl acrylamide; SiH((CH2CH(C(=O)NH2) 1-40 )2-silyldi(acrylamide); Si((CH2CH(C(=O)NH2) 1-40 )3-silyltri(acrylamide); SiH2(CH2CH(C(=O)NH(CH(CH3)2))) 1-40 Silyl N-isopropylacrylamide; branched SiH2O(CH2CH(C(=O)NH(CH(CH3)2))) 1-40 Silyl N-isopropylacrylamide; SiH((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )2-silyldi(N-isopropylacrylamide); Si((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )3-silyltri(N-isopropylacrylamide); SiH2(CH2CH(C(=ONHCH2CH2OH))) 1-40 Silylhydroxyethylmethacrylamide; branched SiH2(CH2CH(C(=ONHCH2CH2OH))) 1-40 Silylhydroxyethylmethacrylamide; SiH((CH2CH(C(=ONHCH2CH2OH))) 1-40 )2-silyldi(hydroxyethylmethacrylamide); SiH((CH2CH(C(=ONHCH2CH2OH))) 1-40 )3-silyltri(hydroxyethylmethacrylamide); SiH2(CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 Silyl 2-hydroxypropylmethacrylamide; branched SiH2(CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 Silyl 2-hydroxypropylmethacrylamide; SiH((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 )2-silyldi(2-hydroxypropylmethacrylamide); Si((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 )3-silyltri(2-hydroxypropylmethacrylamide); SiH2(CH2C(-OSO3M)) 1-40 Silyl vinyl sulfate salt; branched SiH2(CH2C(-OSO3M))1-40 Silyl vinyl sulfate salt; SiH((CH2C(-OSO3M)) 1-40 )2-silyldi(vinyl sulfate salt); SiH((CH2C(-OSO3M)) 1-40 )3-silyltri(vinyl sulfate salt); SiH2(CH2-4-C6H6SO3H) 1-40 Silyl 4-styrenesulfonic acid; branched SiH2(CH2-4-C6H6SO3H) 1-40 Silyl 4-styrenesulfonic acid; SiH((CH2-4-C6H6SO3H) 1-40 )2-silyldi(4-styrenesulfonic acid); SiH((CH2-4-C6H6SO3H) 1-40 )3-silyltri(4-styrenesulfonic acid); SiH2(CH2-4-C6H6SO3NH4) 1-40 Silyl 4-styrenesulfonate ammonium salt; branched SiH2(CH2-4-C6H6SO3NH4) 1-40 Silyl 4-styrenesulfonate ammonium salt; SiH((CH2-4-C6H6SO3NH4) 1-40 )2-silyldi(4-styrenesulfonate ammonium salt); SiH((CH2-4-C6H6SO3NH4) 1-40 )3-silyltri(4-styrenesulfonate ammonium salt); SiH2(CH2C6H6SO3M) 1-40 Silyl 4-styrenesulfonate salt; branched SiH2(CH2C6H6SO3M) 1-40 Silyl 4-styrenesulfonate salt; SiH((CH2C6H6SO3M) 1-40 )2-silyldi(4-styrenesulfonate salt); SiH((CH2C6H6SO3M) 1-40 )3-silyltri(4-styrenesulfonate salt); SiH2(CHCH2NH2) 1-40 Silylalkylamine; branched SiH2(CHCH2NH2) 1-40 Silylalkylamine; SiH((CHCH2NH2) 1-40 )2-silyldi(alkylamine); SiH((CHCH2NH2) 1-40 )3-silyltri(alkylamine); SiH2(CHCH2NH2·HCl) 1-40 Silylalkylamine hydrochloride; branched SiH2(CHCH2NH2·HCl) 1-40 Silylalkylamine hydrochloride; SiH((CHCH2NH2·HCl) 1-40)2-silyldi(alkylamine hydrochloride); SiH((CHCH2NH2·HCl) 1-40 )3-silyltri(alkylamine hydrochloride); SiH2(CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 Silylethyleneimine; SiH((CH2N(CH2CH2N) 1-2 or SiH2O(CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )2-silyldi(ethyleneimine); Si((CH2N(CH2CH2N) 1-2 or SiH2O(CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )3-silyltri(ethyleneimine); SiH2(CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 Silylethyleneimine·hydrochloric acid; SiH((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )2-silyldi(ethyleneimine·hydrochloric acid); Si((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )3-silyltri(ethyleneimine·hydrochloric acid); SiH2(CH2SO3M) 1-40 Silyl vinyl sulfonate; branched SiH2(CH2SO3M) 1-40 Silyldivinylsulfonate; SiH((CH2SO3M) 1-40 )2-silyldi(vinylsulfonate); Si((CH2SO3M) 1-40 )3-silyltri(vinylsulfonate); SiH2(CH2CHC(=O)NH2)) 1-40 Silyl acrylamide; branched SiH2(CH2CHC(=O)NH2)) 1-40 Silyldiacrylamide; SiH((CH2CHC(=O)NH2)) 1-40 )2-silyldi(acrylamide); Si((CH2CHC(=O)NH2)) 1-40)3-silyltri(acrylamide); SiH2(CH2CH(C(=O)NHCH(CH3)2)) 1-40 Silyl N-isopropylacrylamide; branched SiH2(CH2CH(C(=O)NHCH(CH3)2)) 1-40 Silyl N-isopropylacrylamide; SiH((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )2-silyldi(N-isopropylacrylamide); Si((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )3silyltri(N-isopropylacrylamide); SiH2(CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Silyltetramethylpyrrolidium chloride; branched SiH2(CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Silyltetramethylpyrrolidium chloride; SiH((CH2(cyclic SiH2OCHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )2silyldi(tetramethylpyrrolidium chloride); and Si((CH2(cyclic SiH2OCHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )3silyltri(tetramethylpyrrolidium chloride); may be any one selected from the group consisting of.

[0027] In addition, the present disclosure provides a biodegradable composition comprising the hydrophobic polycarbonate polymer.

[0028] The biodegradable composition according to one example of the present disclosure may further comprise at least one selected from the group consisting of a remote triggering pyrogen, an enzyme, and a catalyst.

[0029] The remote triggering heat source according to an example of the present disclosure may include at least one selected from the group consisting of an infrared absorbing dye, magnetic particles, and an electric element.

[0030] In addition, the present disclosure provides a biodegradable material for moisture blocking, prepared from the biodegradable composition.

[0031] Additionally, the present disclosure provides a hydrolysis-resistant biodegradable material prepared from the biodegradable composition.

[0032] In addition, the present disclosure provides a biodegradable off-on material comprising the above-described moisture-blocking biodegradable material; and the above-described hydrolysis-resistant biodegradable material.

[0033] The biodegradable off-on material according to one example of the present disclosure may further include one or more biodegradable trigger layers.

[0034] In addition, the present disclosure provides a biodegradation off-on method, including a step of forming a moisture barrier layer on all or part of the surface of a hydrolysis mechanism biodegradable material, and then forming a hydrolysis resistant layer on all or part of the surface of the moisture barrier layer to turn off the biodegradability of the hydrolysis mechanism biodegradable material; and a step of applying an artificial stimulus to at least one selected from the group consisting of the moisture barrier layer and the hydrolysis resistant layer to turn on the biodegradability of the hydrolysis mechanism biodegradable material.

[0035] According to an example of the present disclosure, the artificial stimulus may be at least one selected from the group consisting of electromagnetic wave energy, thermal energy, ultrasonic energy, enzymes, and catalysts.

[0036] According to an example of the present disclosure, the step of turning off the biodegradability may be to form the moisture barrier layer on all or part of the surface of the hydrolysis mechanism biodegradable material, then form the biodegradation trigger layer on all or part of the surface of the moisture barrier layer, and then form the hydrolysis resistance layer on all or part of the surface of the biodegradation trigger layer.

[0037] The step of turning on biodegradability according to an example of the present disclosure may be to apply an artificial stimulus to the biodegradation trigger layer.

[0038] Polycarbonate polymers according to an example of the present disclosure can change the hydrolysis resistance, melting point, water permeation resistance, hydrolysis rate, and decomposition characteristics by lipolytic enzymes by changing the chemical structure of specific regions.

[0039] A polycarbonate polymer according to an example of the present disclosure may be applied as a protective outer covering material for materials susceptible to hydrolysis, a drug delivery vehicle, a moisture-absorbing biodegradable material, and an environmentally friendly biodegradable material.

[0040] By utilizing a hydrophobic polycarbonate polymer according to an example of the present disclosure, biodegradation of a hydrolysis mechanism biodegradable material can be blocked (off) until a desired time and triggered (on) at a desired time.

[0041] Biodegradable off-on materials comprising hydrophobic polycarbonate polymers according to an example of the present disclosure may be applied to drug delivery, biodegradable medical devices for human implantation, biodegradable devices for environmental monitoring, bioplastics, and transient electronics.

[0042] Figure 1 is a schematic diagram of a biodegradable off-on material according to an example of the present disclosure.

[0043] Figure 2 is an experimental result confirming whether a polycarbonate polymer is biodegradable off-on according to an example of the present disclosure.

[0044] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.

[0045] As used herein, the singular forms may be intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0046] Throughout this specification, the terms "comprises," "includes," "contains," or "has" a component, unless specifically stated to the contrary, do not exclude other components, but rather may include other components, and do not exclude additional unrecited elements, materials, or processes.

[0047] The numerical ranges used herein include the lower and upper limits and all values ​​within that range, increments logically derived from the shape and width of the defined range, all doubly defined values, and all possible combinations of the upper and lower limits of numerical ranges defined in different shapes. Unless otherwise specified herein, values ​​outside the defined range that may arise due to experimental error or rounding of values ​​are also included in the defined numerical range.

[0048] Unless otherwise specified herein, “about” may be considered a value within 30%, 25%, 20%, 15%, 10% or 5% of the stated value.

[0049] The term "biodegradable off-on material" as used herein refers to a material that can block (off) biodegradation of a biodegradable material until a desired time and induce (on) biodegradation of a biodegradable material at a desired time.

[0050] The term "substituted" in this specification may mean that all or part of the hydrogens connected to carbons contained in the compound are replaced with another element or substituent, and "unsubstituted" may mean that all of the hydrogens connected to carbons contained in the compound are not replaced.

[0051] Terms commonly used in this specification may be used with the same meaning unless otherwise defined.

[0052] Below, the present disclosure will be described in detail. However, this is merely exemplary and the present disclosure is not limited to the specific embodiments described as examples.

[0053] The present disclosure provides a polycarbonate polymer comprising a repeating unit represented by the following chemical formula 1, wherein the polycarbonate polymer is R-type by an external stimulus. 1 A novel polycarbonate polymer is provided, wherein the hydroxyl group is recovered by detachment.

[0054] [Chemical Formula 1]

[0055]

[0056] In the above chemical formula 1, R 1 A chain-like (C3-C40) alkyl group excluding a benzyl group, a (C1-C2) alkyl group, a 3-[(2-hydroxyethyl)thiol] propyl group, and an allyl group; a branched (C3-C40) alkyl group; a (C3-C40) cycloalkyl group; a (C3-C40) heterocycloalkyl group; a (C3-C40) alkenyl group; a (C3-C40) alkynyl group; a (C1-C40) heteroalkyl group; a (C6-C40) aryl group; a (C3-C40) heteroaryl group; a (C6-C40) aryl (C1-C40) alkyl group; a (C2-C40) alkyl (C6-C40) aryl group; -Si(R 2 )(R 3 )(R 4 ) silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR8 acyl group; or -S(=O)2R 9 may be sulfonic acid; R 2 Inland R 4 are each independently hydrogen, (C1-C40)alkyl group or (C6-C40)aryl group, and R 2 Inland R 4 At least one of them may be a (C1-C40) alkyl group or a (C6-C40) aryl group, and R 5 Inland R 9 are each independently a (C1-C40) alkyl group, a (C3-C40) alkenyl group, a (C3-C40) alkynyl group, a (C3-C40) cycloalkyl group, a (C3-C40) heterocycloalkyl group, a (C6-C40) aryl group, a (C3-C40) heteroaryl group, a (C6-C40) aryl(C1-C40) alkyl group, a (C1-C40) alkyl(C6-C40) aryl group, or a substituent derived from a hydrophilic polymer, and * is a bonding site. R 1 When this is satisfied, the polycarbonate polymer can recover hydroxyl groups even by a mild reaction rather than a hydrogenation reaction that proceeds in the presence of a catalyst.

[0057] In one example of the present disclosure, the (C3-C40)heterocycloalkyl group may be substituted or unsubstituted, and as a specific example, the substituted or unsubstituted (C3-C40)heterocycloalkyl group may be represented by the following chemical formula 2.

[0058] [Chemical Formula 2]

[0059]

[0060] The above unsubstituted (C3-C40)heterocycloalkyl group may be such that X1 is -0- or -S-. The above substituted (C3-C40)heterocycloalkyl group may be such that X1 is -0- or -S-, and X 1From other carbons, an alkene group (-C=C), an alkyne group (-C≡C), a halide group (-X), an alcohol group (-OH), a thiol group (-SH), an amine group (-NH2), an amide group (-CONH), an aldehyde group (-CHO), a carboxyl group (-COOH), an azide group (-C≡N), a (C1-C8)alkoxy group (-OR), a (C6-C20)aryl group, a (C3-C20)heteroaryl group, or a (C6-C20)aryl(C1-C10)alkyl group may be connected to a (C1-C7)alkyl group.

[0061] In one example of the present disclosure, the artificial stimulus may be at least one selected from the group consisting of electromagnetic wave energy, thermal energy, ultrasonic energy, enzymes, and catalysts.

[0062] In one example of the present disclosure, the enzyme may be at least one selected from the group consisting of lipase, phospholipase, cholesterol esterase, magnesium-dependent lipase, and fatty acid hydrolase, but is not limited thereto.

[0063] In one example of the present disclosure, the catalyst may be beta cyclodextrin, but is not limited thereto as long as it can perform the same or similar function.

[0064] In one example of the present disclosure, the polycarbonate polymer may be a hydrophobic polycarbonate polymer.

[0065] In one example of the present disclosure, the polycarbonate polymer is a hydrolysis-resistant polycarbonate polymer, and R 1 The above polycarbonate polymer is R 1This chain-like (C3-C40) alkyl group; branched (C3-C40) alkyl group; (C3-C40) cycloalkyl group; (C3-C40) heterocycloalkyl group; (C3-C40) alkenyl group; (C3-C40) alkynyl group; (C1-C40) heteroalkyl group; (C6-C40) aryl group; (C3-C40) heteroaryl group; (C6-C40) aryl (C1-C40) alkyl group; or (C2-C40) alkyl (C6-C40) aryl group may be selected. When this is satisfied, the hydrolysis resistance may be particularly strong.

[0066] In one example of the present disclosure, in the hydrophobic polycarbonate polymer, R in the chemical formula 1 1 A chain-like (C3-C20) alkyl group; a branched (C3-C20) alkyl group; a (C3-C20) cycloalkyl group; a (C3-C20) heterocycloalkyl group; a (C1-C20) alkoxy (C1-C20) alkyl group; a (C3-C20) alkenyl group; -Si(R 2 )(R 3 )(R 4 ) silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 acyl group; or -S(=O)2R 9 may be sulfonic acid; R 2 Inland R 4 Each of can be independently a (C1-C20) alkyl group or a (C6-C20) aryl group, and R 5 Inland R 9 may each independently be a (C1-C20)alkyl group, a (C3-C20)alkenyl group, a (C3-C20)alkynyl group, a (C3-C20)cycloalkyl group, a (C3-C20)heterocycloalkyl group, a (C6-C20)aryl group, a (C3-C20)heteroaryl group, a (C6-C20)aryl(C1-C20)alkyl group, or a (C1-C20)alkyl(C6-C20)aryl group.

[0067] In one example of the present disclosure, in the hydrophobic polycarbonate polymer, R in the chemical formula 1 5 Inland R9 Each may be independently any one selected from the group consisting of a (C1-C20) alkyl group, a (C3-C20) cycloalkyl group, a (C3-C20) heterocycloalkyl group, a substituent represented by the following chemical formula 3, and a substituent represented by the following chemical formula 4.

[0068] [Chemical Formula 3]

[0069]

[0070] [Chemical Formula 4]

[0071]

[0072] R 11 Inland R 13 may each independently be a (C1-C7) alkyl group, and a to c may each independently be an integer selected from 0 to 3.

[0073] In one example of the present disclosure, the hydrophobic polycarbonate polymer may be grafted with a hydrophilic brush. When this is satisfied, the hydrophobic polycarbonate polymer can be prevented from decomposing before a desired time point under conditions similar to those in an in vivo environment where lipolytic enzymes are present.

[0074] In one example of the present disclosure, the hydrophilic brush comprises a (C1-200)alkyl(C4-10)heteroalkylsulfobetaine containing a zwitterion, a (C1-200)alkyl((C4-10)heteroalkylsulfobetaine)2, a branched (C2-200)alkyl(C4-10)heteroalkylsulfobetaine, a (C1-200)alkyl(C4-10)heteroalkylcarboxybetaine, a (C1-200)alkyl((C4-10)heteroalkylcarboxybetaine)2, a branched (C2-200)alkyl(C4-10)heteroalkylcarboxybetaine, a (C1-200)alkyl(C4-10)heteroalkylphosphobetaine, (C1-200)alkyl((C4-10)heteroalkylcarphosphobetaine)2, branched (C2-200)alkyl(C4-10)heteroalkylphosphobetaine, or a combination thereof.

[0075] In one example of the present disclosure, the number average molecular weight (M) of the hydrophobic polycarbonate polymer n ) may be 10,000 to 1,000,000 g / mol, specifically 15,000 to 800,000 g / mol, but is not limited thereto as long as the purpose of the present disclosure can be achieved.

[0076] In one example of the present disclosure, the melting point of the hydrophobic polycarbonate polymer may be 43 to 50°C. When this is satisfied, the polymer can be converted into a liquid phase by heat without exhibiting human toxicity.

[0077] In one example of the present disclosure, the polycarbonate polymer is a hydrophilic polycarbonate polymer, and R in the chemical formula 1 1 Silver -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 acyl group; or -S(=O)2R 9 It can be a sulfonyl group, and R 5 Inland R 9 Each of may independently be a substituent derived from a hydrophilic polymer.

[0078] In one example of the present disclosure, the hydrophilic polymer is (CH2CH2O) 1-40 Ethylene glycol; ((CH2CH2O) 1-40 )2-Diethylene glycol; branched (CH2CH2O) 1-40Ethylene glycol; (C1-40) alkyl (C4-10) heteroalkyl sulfobetaine; (C1-40) alkyl ((C4-10) heteroalkyl sulfobetaine)2; branched (C1-40) alkyl (C4-10) heteroalkyl sulfobetaine; (C1-40) alkyl (C4-10) heteroalkyl carboxybetaine; (C1-40) alkyl ((C4-10) heteroalkyl carboxybetaine)2; branched (C1-40) alkyl (C4-10) heteroalkyl carboxybetaine; (C1-40) alkyl ((C4-10) heteroalkyl phosphobetaine; (C1-40) alkyl ((C4-10) heteroalkyl phosphobetaine)2; Branched (C1-40) alkyl (C4-10) heteroalkyl phosphobetaine; (CH2COH) 1~40 Vinyl alcohol; ((CH2COH) 1~40 )2-Divinyl alcohol; branched (CH2COH) 1~40 Vinyl alcohol; (CH2COOH) 1-40 Acrylic acid; ((CH2COOH) 1-40 )2-Diacrylic acid; branched (CH2COOH) 1-40 Acrylic acid; (CH2COOM) 1-40 Acrylate; ((CH2COOM) 1-40 )2 diacrylate; branched (CH2COOM) 1-40 Acrylic acid salt; (CH2C(CH3)(C(=O0H)) 1-40 Methacrylic acid; ((CH2C(CH3)(C(=O0H)) 1-40 )2-dimethacrylic acid; branched (CH2C(CH3)(C(=O0H)) 1-40 Methacrylic acid; (CH2C(CH3)(C(=O0M)) 1-40 Methacrylate; ((CH2C(CH3)(C(=O0M)) 1-40 )2-dimethacrylate; branched (CH2C(CH3)(C(=O0M)) 1-40 Methacrylate; (CH2C(CH3)(C(=O)OH)) 1-40 2-propylacrylic acid; ((CH2C(CH3)(C(=O)OH)) 1-40 )2-di-2-propylacrylic acid; branched (CH2C(CH3)(C(=O)OH)) 1-40 2-propylacrylic acid; (CH2C(CH3)(C(=O)OM)) 1-402-propyl acrylate; (((CH2C(CH3)(C(=O)OM)) 1-40 )2di2-propyl acrylate; branched (CH2C(CH3)(C(=O)OM)) 1-40 2-propyl acrylate; (CH2CH(C(=O)NH2) 1-40 Acrylamide; ((CH2CH(C(=O)NH2) 1-40 )2 diacrylamide; branched (CH2CH(C(=O)NH2) 1-40 Acrylamide; (CH2CH(C(=O)NH(CH(CH3)2))) 1-40 N-isopropylacrylamide; ((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )2-diN-isopropylacrylamide; branched (CH2CH(C(=O)NH(CH(CH3)2))) 1-40 N-isopropylacrylamide; (CH2CH(C(=ONHCH2CH2OH))) 1-40 Hydroxyethylmethacrylamide; ((CH2CH(C(=ONHCH2CH2OH))) 1-40 )2-dihydroxyethylmethacrylamide; branched (CH2CH(C(=ONHCH2CH2OH))) 1-40 Hydroxyethylmethacrylamide; (CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 2-Hydroxypropylmethacrylamide; ((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40) Di-2-hydroxypropylmethacrylamide; branched (CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 2-Hydroxypropylmethacrylamide; (CH2C(-OSO3M)) 1-40 Vinyl sulfate salt; ((CH2C(-OSO3M)) 1-40 )2-divinyl sulfate salt; branched (CH2C(-OSO3M)) 1-40 Vinyl sulfate salt; (CH2-4-C6H6SO3H) 1-40 4-styrenesulfonic acid; ((CH2-4-C6H6SO3H) 1-40 )2-di-4-styrenesulfonic acid; branched (CH2-4-C6H6SO3H) 1-404-styrenesulfonic acid; (CH2-4-C6H6SO3NH4) 1-40 4-Styrenesulfonate ammonium salt; ((CH2-4-C6H6SO3NH4) 1-40 )2di4-styrenesulfonate ammonium salt; branched (CH2-4-C6H6SO3NH4) 1-40 4-styrenesulfonate ammonium salt; (CH2C6H6SO3M) 1-40 4-styrenesulfonate salt; ((CH2C6H6SO3M) 1-40 )2di-4-styrenesulfonate salt; branched (CH2C6H6SO3M) 1-40 4-styrenesulfonate salt; (CHCH2NH2) 1-40 Alkylamine; ((CHCH2NH2) 1-40 )2-dialkylamine; branched (CHCH2NH2) 1-40 Alkylamine; (CHCH2NH2·HCl) 1-40 Alkylamine hydrochloride; ((CHCH2NH2·HCl) 1-40 )2-Dialkylamine hydrochloride; branched (CHCH2NH2·HCl) 1-40 Alkylamine hydrochloride; (CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 Ethyleneimine; ((CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )2-diethyleneimine; (CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 Ethyleneimine hydrochloride; ((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )2-Diethyleneimine hydrochloride; (CH2SO3M) 1-40 Vinyl sulfonate; ((CH2SO3M) 1-40 )2-Divinylsulfonate; branched (CH2SO3M) 1-40 Vinyl sulfonate; (CH2CHC(=O)NH2)) 1-40 Acrylamide; ((CH2CHC(=O)NH2))1-40 )2 diacrylamide; branched (CH2CHC(=O)NH2)) 1-40 Acrylamide (CH2CH(C(=O)NHCH(CH3)2)) 1-40 N-isopropylacrylamide; ((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )2-diN-isopropylacrylamide; branched (CH2CH(C(=O)NHCH(CH3)2)) 1-40 N-isopropylacrylamide; (CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Tetramethylpyrrolidium chloride; ((CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )2-ditetramethylpyrrolidium chloride; branched (CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Tetramethylpyrrolidium chloride; SiH2(CH2CH2O) 1-40 Silyl ethylene glycol; branched SiH2((CH2CH2O) 1-40 )silylethylene glycol; SiH((CH2CH2O) 1-40 )2-silyldi(ethylene glycol); Si((CH2CH2O) 1-40 )3-silyltri(ethylene glycol); SiH2(CH2COH) 1~40 Silyl vinyl alcohol; branched SiH2O(CH2COH) 1~40 Silyl vinyl alcohol; SiH((CH2COH) 1~40 )2-silyldi(vinyl alcohol); Si((CH2COH) 1~40 )3-silyltri(vinyl alcohol); SiH2(CH2COOH) 1-40 Silyl acrylate; branched SiH2(CH2COOH) 1-40 Silyl acrylate; SiH((CH2COOH) 1-40 )2-silyldi(acrylic acid); Si((CH2COOH) 1-40 )2-silyltri(acrylic acid); SiH2(CH2COOM) 1-40Silyl acrylate; branched SiH2(CH2COOM) 1-40 Silyl acrylate; SiH((CH2COOM) 1-40 )2-silyldi(acrylate); Si((CH2COOM) 1-40 )3-silyltri(acrylate); SiH2(CH2C(CH3)(C(=O0H)) 1-40 Silylmethacrylic acid; branched SiH2(CH2C(CH3)(C(=O0H)) 1-40 Silylmethacrylic acid; SiH((CH2C(CH3)(C(=O0H)) 1-40 )2-silyldi(methacrylic acid); Si((CH2C(CH3)(C(=O0H)) 1-40 )3-silyltri(methacrylic acid); SiH2(CH2C(CH3)(C(=O0M)) 1-40 Silyl methacrylate; branched SiH2(CH2C(CH3)(C(=O0M)) 1-40 Silyl methacrylate; SiH((CH2C(CH3)(C(=O0M)) 1-40 )2-silyldi(methacrylate); Si((CH2C(CH3)(C(=O0M)) 1-40 )3-silyltri(methacrylate); SiH2(CH2C(CH3)(C(=O)OH)) 1-40 Silyl-2-propylacrylic acid; branched SiH2(CH2C(CH3)(C(=O)OH)) 1-40 Silyl-2-propylacrylic acid; SiH((CH2C(CH3)(C(=O)OH)) 1-40 )2-silyldi(2-propylacrylic acid); Si((CH2C(CH3)(C(=O)OH)) 1-40 )3-silyltri(2-propylacrylic acid); SiH2(CH2C(CH3)(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; branched SiH2(CH2C(CH3)(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; SiH(((CH2C(CH3)(C(=O)OM)) 1-40) )2-silyldi(2-propylacrylate); Si(((CH2C(CH3)(C(=O)OM)) 1-40) )2-silyltri(2-propylacrylate); SiH2(CH2CH(C(=O)NH2) 1-40Silyl acrylamide; branched SiH2(CH2CH(C(=O)NH2) 1-40 Silyl acrylamide; SiH((CH2CH(C(=O)NH2) 1-40 )2-silyldi(acrylamide); Si((CH2CH(C(=O)NH2) 1-40 )3-silyltri(acrylamide); SiH2(CH2CH(C(=O)NH(CH(CH3)2))) 1-40 Silyl N-isopropylacrylamide; branched SiH2O(CH2CH(C(=O)NH(CH(CH3)2))) 1-40 Silyl N-isopropylacrylamide; SiH((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )2-silyldi(N-isopropylacrylamide); Si((CH2CH(C(=O)NH(CH(CH3)2))) 1-40 )3-silyltri(N-isopropylacrylamide); SiH2(CH2CH(C(=ONHCH2CH2OH))) 1-40 Silylhydroxyethylmethacrylamide; branched SiH2(CH2CH(C(=ONHCH2CH2OH))) 1-40 Silylhydroxyethylmethacrylamide; SiH((CH2CH(C(=ONHCH2CH2OH))) 1-40 )2-silyldi(hydroxyethylmethacrylamide); SiH((CH2CH(C(=ONHCH2CH2OH))) 1-40 )3-silyltri(hydroxyethylmethacrylamide); SiH2(CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 Silyl 2-hydroxypropylmethacrylamide; branched SiH2(CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 Silyl 2-hydroxypropylmethacrylamide; SiH((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 )2-silyldi(2-hydroxypropylmethacrylamide); Si((CH2CH(C(=ONHCH2CH(OH)CH3))) 1-40 )3-silyltri(2-hydroxypropylmethacrylamide); SiH2(CH2C(-OSO3M)) 1-40 Silyl vinyl sulfate salt; branched SiH2(CH2C(-OSO3M))1-40 Silyl vinyl sulfate salt; SiH((CH2C(-OSO3M)) 1-40 )2-silyldi(vinyl sulfate salt); SiH((CH2C(-OSO3M)) 1-40 )3-silyltri(vinyl sulfate salt); SiH2(CH2-4-C6H6SO3H) 1-40 Silyl 4-styrenesulfonic acid; branched SiH2(CH2-4-C6H6SO3H) 1-40 Silyl 4-styrenesulfonic acid; SiH((CH2-4-C6H6SO3H) 1-40 )2-silyldi(4-styrenesulfonic acid); SiH((CH2-4-C6H6SO3H) 1-40 )3-silyltri(4-styrenesulfonic acid); SiH2(CH2-4-C6H6SO3NH4) 1-40 Silyl 4-styrenesulfonate ammonium salt; branched SiH2(CH2-4-C6H6SO3NH4) 1-40 Silyl 4-styrenesulfonate ammonium salt; SiH((CH2-4-C6H6SO3NH4) 1-40 )2-silyldi(4-styrenesulfonate ammonium salt); SiH((CH2-4-C6H6SO3NH4) 1-40 )3-silyltri(4-styrenesulfonate ammonium salt); SiH2(CH2C6H6SO3M) 1-40 Silyl 4-styrenesulfonate salt; branched SiH2(CH2C6H6SO3M) 1-40 Silyl 4-styrenesulfonate salt; SiH((CH2C6H6SO3M) 1-40 )2-silyldi(4-styrenesulfonate salt); SiH((CH2C6H6SO3M) 1-40 )3-silyltri(4-styrenesulfonate salt); SiH2(CHCH2NH2) 1-40 Silylalkylamine; branched SiH2(CHCH2NH2) 1-40 Silylalkylamine; SiH((CHCH2NH2) 1-40 )2-silyldi(alkylamine); SiH((CHCH2NH2) 1-40 )3-silyltri(alkylamine); SiH2(CHCH2NH2·HCl) 1-40 Silylalkylamine hydrochloride; branched SiH2(CHCH2NH2·HCl) 1-40 Silylalkylamine hydrochloride; SiH((CHCH2NH2·HCl) 1-40)2-silyldi(alkylamine hydrochloride); SiH((CHCH2NH2·HCl) 1-40 )3-silyltri(alkylamine hydrochloride); SiH2(CH2N(CH2CH2N) 1-2 or (CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 Silylethyleneimine; SiH((CH2N(CH2CH2N) 1-2 or SiH2O(CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )2-silyldi(ethyleneimine); Si((CH2N(CH2CH2N) 1-2 or SiH2O(CH2CH2N(CH2CH2NH2)2)CH2CH2NHCH2) 1-40 )3-silyltri(ethyleneimine); SiH2(CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 Silylethyleneimine·hydrochloric acid; SiH((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )2-silyldi(ethyleneimine·hydrochloric acid); Si((CH2N(CH2CH2N·HCl) 1-2 or (CH2CH2N(CH2CH2NH2·HCl)2)CH2CH2NHCH2) 1-40 )3-silyltri(ethyleneimine·hydrochloric acid); SiH2(CH2SO3M) 1-40 Silyl vinyl sulfonate; branched SiH2(CH2SO3M) 1-40 Silyldivinylsulfonate; SiH((CH2SO3M) 1-40 )2-silyldi(vinylsulfonate); Si((CH2SO3M) 1-40 )3-silyltri(vinylsulfonate); SiH2(CH2CHC(=O)NH2)) 1-40 Silyl acrylamide; branched SiH2(CH2CHC(=O)NH2)) 1-40 Silyldiacrylamide; SiH((CH2CHC(=O)NH2)) 1-40 )2-silyldi(acrylamide); Si((CH2CHC(=O)NH2)) 1-40)3-silyltri(acrylamide); SiH2(CH2CH(C(=O)NHCH(CH3)2)) 1-40 Silyl N-isopropylacrylamide; branched SiH2(CH2CH(C(=O)NHCH(CH3)2)) 1-40 Silyl N-isopropylacrylamide; SiH((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )2-silyldi(N-isopropylacrylamide); Si((CH2CH(C(=O)NHCH(CH3)2)) 1-40 )3silyltri(N-isopropylacrylamide); SiH2(CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Silyltetramethylpyrrolidium chloride; branched SiH2(CH2(cyclic CHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 Silyltetramethylpyrrolidium chloride; SiH((CH2(cyclic SiH2OCHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )2silyldi(tetramethylpyrrolidium chloride); and Si((CH2(cyclic SiH2OCHCH2N + (CH3)2CH2CH·Cl - )CH2) 1-40 )3silyltri(tetramethylpyrrolidium chloride); may be any one selected from the group consisting of.

[0079] In one example of the present disclosure, the polycarbonate polymer may be a polymerization of a polycarbonate monomer represented by the following chemical formula 5.

[0080] [Chemical Formula 5]

[0081]

[0082] In the above chemical formula 5, R 1 is the same as the definition in the above chemical formula 1.

[0083] In addition, the present disclosure provides a biodegradable composition comprising the hydrophobic polycarbonate polymer.

[0084] In one example of the present disclosure, the biodegradable composition may further comprise one or more selected from the group consisting of a remote triggering pyrogen, an enzyme, and a catalyst.

[0085] In one example of the present disclosure, the remote triggering heat source may include at least one selected from the group consisting of an infrared absorbing dye, a magnetic particle, and an electrical element.

[0086] Additionally, the present disclosure provides a biodegradable material for moisture blocking, manufactured from the biodegradable composition. The biodegradable material for moisture blocking has an excellent moisture penetration blocking effect, thereby preventing external moisture from penetrating into the interior.

[0087] Additionally, the present disclosure provides a hydrolysis-resistant biodegradable material manufactured from the biodegradable composition. The hydrolysis-resistant biodegradable material exhibits particularly excellent hydrolysis resistance and thus may not be hydrolyzed in the human body or in everyday environments.

[0088] In addition, the present disclosure provides a biodegradable off-on material comprising the above-described moisture-blocking biodegradable material; and the above-described hydrolysis-resistant biodegradable material. Specifically, the biodegradable off-on material may be composed of the above-described hydrolysis-resistant biodegradable material surrounding the above-described moisture-blocking biodegradable material, but is not limited thereto as long as the purpose of the present disclosure can be achieved.

[0089] In one example of the present disclosure, the biodegradable off-on material may further include one or more biodegradation trigger layers between the moisture-blocking biodegradable material and the hydrolysis-resistant biodegradable material.

[0090] In one example of the present disclosure, the biodegradable trigger layer may be manufactured from the biodegradable composition.

[0091] In one example of the present disclosure, the biodegradation trigger layer may include a biodegradation trigger material blocking layer and a biodegradation trigger material containing layer.

[0092] In one example of the present disclosure, the biodegradation triggering material-containing layer may include an enzyme, a catalyst, or a combination thereof, and may include one or more remotely triggered heat sources selected from the group consisting of infrared absorbing dyes, magnetic particles, and electrical elements. When this is satisfied, heat can be remotely induced at a desired time to transfer the biodegradation triggering material-containing layer into a liquid phase, thereby activating the enzyme, catalyst, or a combination thereof. The activated enzyme, etc., can decompose the hydrolysis-resistant biodegradable material.

[0093] The above biodegradation triggering material blocking layer can prevent the hydrolysis-resistant biodegradable material from being decomposed before an enzyme or the like is activated by blocking direct contact between the biodegradation triggering material-containing layer and the hydrolysis-resistant biodegradable material.

[0094] In one example of the present disclosure, the melting points of the polycarbonate polymers included in the biodegradation triggering material-containing layer and the biodegradation triggering material-blocking layer may each independently be 43 to 50°C. In this case, the melting point of the polycarbonate polymer included in the moisture-blocking biodegradable material may be a lower limit of 55°C or higher, 60°C or higher, and an upper limit of 70°C or lower. When this is satisfied, the biodegradable material for moisture blocking may be prevented from being decomposed by enzymes or the like activated by the biodegradation triggering layer being converted to a liquid phase by heat generation.

[0095] In addition, the present disclosure provides a biodegradation off-on method, including a step of forming a moisture barrier layer on all or part of the surface of a hydrolysis mechanism biodegradable material, and then forming a hydrolysis resistant layer on all or part of the surface of the moisture barrier layer to turn off the biodegradability of the hydrolysis mechanism biodegradable material; and a step of applying an artificial stimulus to at least one selected from the group consisting of the moisture barrier layer and the hydrolysis resistant layer to turn on the biodegradability of the hydrolysis mechanism biodegradable material.

[0096] The description of polycarbonate polymers and the like can be equally applied to the description of biodegradable off-on methods to the extent of overlap.

[0097] The step of turning off the biodegradability is a step of turning off the biodegradability by forming a moisture barrier layer on the surface of the hydrolysis mechanism biodegradable material, and then forming a hydrolysis resistant layer on the surface of the moisture barrier layer to prevent the hydrolysis mechanism biodegradable material from being exposed to moisture.

[0098] In one example of the present disclosure, the step of turning off the biodegradability may be to form the moisture barrier layer on all or part of the surface of the hydrolysis mechanism biodegradable material, then form the biodegradation trigger layer on all or part of the surface of the moisture barrier layer, and then form the hydrolysis resistance layer on all or part of the surface of the biodegradation trigger layer.

[0099] The step of turning on the biodegradability is a step of turning on the biodegradability by applying an artificial stimulus to the moisture barrier layer and / or the hydrolysis resistant layer at a desired time to biodegrade the moisture barrier layer and / or the hydrolysis resistant layer, thereby allowing the biodegradable material of the hydrolysis mechanism to be exposed to moisture.

[0100] In one example of the present disclosure, the step of turning on the biodegradability may be applying an artificial stimulus to the biodegradation trigger layer.

[0101] In one example of the present disclosure, the artificial stimulus may be at least one selected from electromagnetic wave energy, thermal energy, ultrasonic energy, enzymes, and catalysts. When the artificial stimulus is applied to the moisture-blocking outer shell, the R contained in the hydrophobic polycarbonate polymer 1 This detachment allows the hydroxyl group to be restored.

[0102] Specifically, the hydrophobic polycarbonate polymer included in the hydrolysis-resistant layer can be converted into a polycarbonate polymer (Poly(5-hydroxy-trimethylene-carbonate), PHTMC) containing a hydroxyl group as shown in the following formula 1 by an external stimulus.

[0103] [Formula 1]

[0104]

[0105] More specifically, the above equation 1 can be expressed as the following equation 2.

[0106] [Formula 2]

[0107]

[0108] The above PHTMC can be rapidly biodegraded under moist conditions by an intramolecular cyclization reaction involving the oxygen of the hydroxyl group and the carbonyl carbon.

[0109] Hereinafter, the above-described implementation examples will be described in more detail through examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0110]

[0111] Example 1

[0112] (1) Monomer production

[0113]

[0114] 1) Step 1

[0115] 2 g (1 eq) of 1,3-dibromopropane-2-ol was dissolved in 50 mL of tetrahydrofuran (THF) in a round-bottomed flask, and 0.25 g (0.1 eq) of pyridium p-toluenesulfonate (PPTS) and 1.68 g (2 eq) of 3,4-dihydro-2H-pyran (DHP) were added, and the mixture was stirred at room temperature for 3 hours. Afterwards, dichloromethane (DCM) and distilled water were used for extraction, and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by column chromatography (EA:Hx=1:9) to obtain compound (A)-1.

[0116] 2) Step 2

[0117] 4 g (1 eq) of the above compound (A)-1 was dissolved in 40 mL of acrylonitrile (ACN) in a round-bottom flask, and then 11.4 g (3 eq) of tetrabutylammonium acetate (Bu4NOAc), 0.923 (0.2 eq) of tetrabutylammonium iodide (Bu4NI), and 0.345 g (0.2 eq) of potassium carbonate (K2CO3) were added and stirred at room temperature overnight. The resulting solid was filtered and extracted with DCM and water. The organic layer was dried over MgSO4, filtered, and concentrated. Thereafter, the residue was purified by column chromatography (EA:Hx=2:8) to obtain compound (A)-2.

[0118] 3) Step 3

[0119] 1.5 g (1 eq) of the above compound (A)-2 was dissolved in 25 mL of ammonia solution (2.0 M in methanol) in a round-bottom flask and stirred overnight at room temperature. Thereafter, the mixture was purified by column chromatography (ether 100%) without extraction to obtain compound (A)-3.

[0120] 4) Step 4

[0121] 1 g (1 eq) of the above compound (A)-3 and 1.23 g (2 eq) of ethyl chloroformate were dissolved in 15 mL of THF in a 2-neck round-bottom flask under nitrogen conditions, and then 1.15 g (2 eq) of triethylamine (TEA) was added over 0.5 h at 0°C. After warming to room temperature, the mixture was stirred for 2 h, extracted with DCM and water, and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was then purified by column chromatography (ether:DCM=2:1) ​​and recrystallized with ether to obtain compound (A), a polycarbonate monomer.

[0122]

[0123] (2) Polycarbonate polymerization

[0124]

[0125] 1 g (1e q) of the above compound (A) and 0.024 g (0.04 eq) of dimethylaminopyridine (DMAP), an initiator, were placed in a round-bottom flask and stirred overnight at 120°C. The resulting polymer was dissolved in chloroform and precipitated in 100 mL of methanol, and the precipitated polymer was washed again with ether. Number-average molecular weight (M n ) A polycarbonate polymer having a molecular weight of 19300 g / mol was obtained.

[0126]

[0127] Example 2

[0128] (1) Monomer production

[0129]

[0130] 1) Step 1

[0131] In a round-bottom flask, 15 g (1 eq) of trilaurin was dissolved in 76 ml of absolute ethanol, and then 15 g of Lipozyme TL IM (substrate-enzyme ratio, 0.5 w / w) was added and stirred at 35°C for 17 hours. The mixture was filtered twice through a glass filter to remove the enzyme, concentrated, and then purified by flash column chromatography (Hexane:Acetone) to obtain 2-monoacryl glycerol.

[0132] 2) Step 2

[0133] 3 g (1 eq) of 2-monoacryl glycerol obtained above and 2.37 g (2 eq) of ethyl chloroformate were dissolved in 404 ml of THF in a 2-neck round-bottom flask under nitrogen conditions, and 2.21 g (2 eq) of triethylamine (TEA) was added over 0.5 h at 0°C. After warming to room temperature, the mixture was stirred overnight, extracted with DCM and water, and the organic layer was dried over MgSO4, filtered, and concentrated. It was then recrystallized with diethyl ether to obtain HTME-FAE, a polycarbonate monomer.

[0134]

[0135] (2) Polycarbonate polymerization

[0136] 1 g (1 eq) of HTMC-laurate was dissolved in 8 ml of anhydrous toluene, and then 38 mg (0.1 eq) of anhydrous benzyl alcohol and 83 mg (0.1 eq) of diphenyl phosphate (DPP) were dissolved in 3 ml and 415 μl of anhydrous toluene, respectively. Benzyl alcohol and DPP stock solutions were added to a round-bottom flask and stirred at 500 rpm for 30 min at 25°C. The HTMC-laurate stock solution was then added and stirred at 500 rpm for 48 h. Afterwards, AmberLyst A21 was added to neutralize the mixture, followed by filtration and concentration. The resulting mixture was purified using an α-alumina pad and dichloromethane (DCM) to obtain PHTMC-laurate. All reactions were performed in a glove box under a nitrogen atmosphere with dehydrated nitrogen.

[0137]

[0138] Example 3

[0139]

[0140] In a round-bottom flask, 2 g (1 eq) of 3,4-Dihydro-2H-pyran-2-methanol was dissolved in 16 ml of dichloromethane (DCM), and 4.66 g (2 eq) of Benzyl isocyanate was added, followed by 0.18 g (0.1 eq) of triethylamine (TEA) and stirred at 25°C for 1 hour. Thereafter, extraction was performed using DCM and distilled water, and the organic layer was dried over MgSO4, filtered and concentrated, with the exception that the same procedure as in Example 1 was performed to obtain the monomer and polymer as follows.

[0141]

[0142]

[0143] Experimental Example 4: Confirmation of biodegradation off-on

[0144] To confirm whether the polycarbonate polymer of the present disclosure is biodegradable off-on, an experiment was conducted and the results are shown in Fig. 2.

[0145] Specifically, the experiment was conducted by placing the polycarbonate polymer synthesized in Example 1 in a pH 7.4 phosphate buffered saline solution and observing the change in the shape of the polymer after 1 hour, then adding beta-cyclodextrin (β-CD), a catalyst with almost no human toxicity, to the PBS solution containing the polymer, and observing the change in the shape of the polymer over time.

[0146] As can be seen in Fig. 2, the polymer according to Example 1 of the present disclosure did not undergo hydrolysis (biodegradation off) because it did not change its shape at all when exposed to moisture. However, when a catalyst corresponding to an artificial stimulus was added, it was confirmed that complete decomposition occurred over time while forming bubbles (biodegradation on). Specifically, by confirming the decomposition pattern while forming bubbles, it was confirmed that R was formed by water and β-CD. 1 As the tetrahydropyranyl group is removed, a hydroxyl group is formed within the polymer, which is then decomposed into glycerol, which is completely non-toxic to the human body, while forming carbon dioxide through an intramolecular cyclization reaction.

[0147] Combining the results of Examples 1, 2, and 4, a biodegradation off-on mechanism as shown in Fig. 1 can be proposed.

[0148]

[0149] Although the above has been described with reference to embodiments, these are merely examples and do not limit the present disclosure. Those skilled in the art to which the present disclosure pertains will appreciate that various modifications and applications not exemplified above are possible without departing from the essential characteristics of the present embodiments. For example, each component specifically shown in the embodiments can be modified and implemented. In addition, differences related to such modifications and applications should be construed as being included within the scope of the present disclosure as defined in the appended claims.

Claims

1. A polycarbonate polymer comprising a repeating unit represented by the following chemical formula 1, The above polycarbonate polymer is R by artificial stimulation. 1 A novel polycarbonate polymer in which the hydroxyl group is recovered by detachment: [Chemical Formula 1] In the above chemical formula 1, R 1 A chain-shaped (C3-C40) alkyl group; a branched (C3-C40) alkyl group; a (C3-C40) cycloalkyl group; a (C3-C40) heterocycloalkyl group; a (C3-C40) alkenyl group; a (C3-C40) alkynyl group; a (C1-C40) heteroalkyl group; a (C6-C40) aryl group; a (C3-C40) heteroaryl group; a (C6-C40) aryl (C1-C40) alkyl group; a (C2-C40) alkyl (C6-C40) aryl group; -Si(R 2 )(R 3 )(R 4 ) is a silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 In acyl group; or -S(=O) 2 R 9 In sulfonyl group; and, R 2 Inland R 4 are each independently hydrogen, (C1-C40) alkyl group or (C6-C40) aryl group, R 2 Inland R 4 At least one of them is a (C1-C40) alkyl group or a (C6-C40) aryl group, R 5 Inland R 9 are each independently a (C1-C40) alkyl group, a (C3-C40) alkenyl group, a (C3-C40) alkynyl group, a (C3-C40) cycloalkyl group, a (C3-C40) heterocycloalkyl group, a (C6-C40) aryl group, a (C3-C40) heteroaryl group, a (C6-C40) aryl(C1-C40) alkyl group, a (C1-C40) alkyl(C6-C40) aryl group or a substituent derived from a hydrophilic polymer, * is the binding site.

2. In paragraph 1, The above polycarbonate polymer is a novel polycarbonate polymer, which is a hydrophobic polycarbonate polymer.

3. In paragraph 2, The above polycarbonate polymer is, It is a hydrolysis-resistant polycarbonate polymer, and R 1 A novel polycarbonate polymer, which is a chain-shaped (C3-C40) alkyl group; a branched (C3-C40) alkyl group; a (C3-C40) cycloalkyl group; a (C3-C40) heterocycloalkyl group; a (C3-C40) alkenyl group; a (C3-C40) alkynyl group; a (C1-C40) heteroalkyl group; a (C6-C40) aryl group; a (C3-C40) heteroaryl group; a (C6-C40) aryl (C1-C40) alkyl group; or a (C2-C40) alkyl (C6-C40) aryl group.

4. In paragraph 2, Above R 1 Silver chain (C3-C20) alkyl group; branched (C3-C20) alkyl group; (C3-C20) cycloalkyl group; (C3-C20) heterocycloalkyl group; (C1-C20) alkoxy (C1-C20) alkyl group; (C3-C20) alkenyl group; -Si(R 2 )(R 3 )(R 4 ) is a silyl group; -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 In acyl group; or -S(=O) 2 R 9 In sulfonyl group; and, R 2 Inland R 4 are each independently a (C1-C20) alkyl group or a (C6-C20) aryl group, R 5 Inland R 9 A novel polycarbonate polymer, wherein each independently represents a (C1-C20) alkyl group, a (C3-C20) alkenyl group, a (C3-C20) alkynyl group, a (C3-C20) cycloalkyl group, a (C3-C20) heterocycloalkyl group, a (C6-C20) aryl group, a (C3-C20) heteroaryl group, a (C6-C20) aryl(C1-C20) alkyl group or a (C1-C20) alkyl(C6-C20) aryl group.

5. In paragraph 2, Above R 5 Inland R 9 A novel polycarbonate polymer, wherein each independently represents one selected from the group consisting of a (C1-C20) alkyl group, a (C3-C20) cycloalkyl group, a (C3-C20) heterocycloalkyl group, a substituent represented by the following chemical formula 3, and a substituent represented by the following chemical formula 4: [Chemical Formula 3] [Chemical Formula 4] R 11 Inland R 13 are each independently a (C1-C7) alkyl group; a to c are each independently integers selected from 0 to 3.

6. In paragraph 3, A novel polycarbonate polymer, wherein the polycarbonate polymer is grafted with a hydrophilic brush.

7. In paragraph 6, The above hydrophilic brush, (C1-200) alkyl (C4-10) heteroalkyl sulfobetaine containing zwitterion, (C1-200) alkyl ((C4-10) heteroalkyl sulfobetaine) 2 , branched (C2-200) alkyl (C4-10) heteroalkyl sulfo betaine, (C1-200) alkyl (C4-10) heteroalkyl carboxy betaine, (C1-200) alkyl ((C4-10) heteroalkyl carboxy betaine) 2 , branched (C2-200) alkyl (C4-10) heteroalkyl carboxybetaine, (C1-200) alkyl (C4-10) heteroalkyl phosphobetaine, (C1-200) alkyl ((C4-10) heteroalkyl phosphobetaine) 2 , a novel polycarbonate polymer, which is a branched (C2-200) alkyl (C4-10) heteroalkyl phosphobetaine or a combination thereof.

8. In paragraph 2, The number average molecular weight (M) of the above hydrophobic polycarbonate polymer n ) is a novel polycarbonate polymer having a molecular weight of 10,000 to 1,000,000 g / mol.

9. In paragraph 2, The above hydrophobic polycarbonate polymer is a novel polycarbonate polymer having a melting point of 43 to 50°C.

10. In paragraph 1, The above polycarbonate polymer is a hydrophilic polycarbonate polymer, In the above chemical formula 1, R 1 is -C(=O)R 5 , -C(=O)NHR 6 , -C(=O)NR 7 2 or -C(=O)OR 8 In acyl group; or -S(=O) 2 R 9 It is a sulfonyl group; R 5 Inland R 9 A novel polycarbonate polymer, each independently a substituent derived from a hydrophilic polymer.

11. In paragraph 10, The above hydrophilic polymer is (CH 2 CH 2 O) 1-40 Ethylene glycol; ((CH 2 CH 2 O) 1-40 ) 2 Diethylene glycol; branched (CH 2 CH 2 O) 1-40 Ethylene glycol; (C1-40) alkyl (C4-10) heteroalkyl sulfobetaine; (C1-40) alkyl ((C4-10) heteroalkyl sulfobetaine) 2 ; Branched (C1-40) alkyl (C4-10) heteroalkyl sulfo betaine; (C1-40) alkyl (C4-10) heteroalkyl carboxy betaine; (C1-40) alkyl ((C4-10) heteroalkyl carboxy betaine) 2 ; Branched (C1-40) alkyl (C4-10) heteroalkyl carboxybetaine; (C1-40) alkyl (C4-10) heteroalkyl phosphobetaine; (C1-40) alkyl ((C4-10) heteroalkyl phosphobetaine) 2 ; Branched (C1-40) alkyl (C4-10) heteroalkyl phosphobetaine; (CH 2 COH) 1~40 Vinyl alcohol; ((CH 2 COH) 1~40 ) 2 Divinyl alcohol; branched (CH 2 COH) 1~40 Vinyl alcohol; (CH 2 COOH) 1-40 Acrylic acid; ((CH 2 COOH) 1-40 ) 2 Diacrylic acid; branched (CH 2 COOH) 1-40 Acrylic acid; (CH 2 COOM) 1-40 Acrylic acid salt; ((CH 2 COOM) 1-40 ) 2 Diacrylate; branched (CH 2 COOM) 1-40 Acrylic acid salt; (CH 2 C(CH 3 )(C(=O0H)) 1-40 Methacrylic acid; ((CH 2 C(CH 3 )(C(=O0H)) 1-40 ) 2 Dimethacrylic acid; branched (CH 2 C(CH 3 )(C(=O0H)) 1-40 Methacrylic acid; (CH 2 C(CH 3 )(C(=O0M)) 1-40 Methacrylate; ((CH 2 C(CH 3 )(C(=O0M)) 1-40 ) 2 Dimethacrylate; branched (CH 2 C(CH 3 )(C(=O0M)) 1-40 Methacrylate; (CH 2 C(CH 3 )(C(=O)OH)) 1-40 2-Propyl acrylic acid; ((CH 2 C(CH 3 )(C(=O)OH)) 1-40 ) 2 Di-2-propylacrylic acid; branched (CH 2 C(CH 3 )(C(=O)OH)) 1-40 2-Propyl acrylic acid; (CH 2 C(CH 3 )(C(=O)OM)) 1-40 2-Propyl acrylate; (((CH 2 C(CH 3 )(C(=O)OM)) 1-40 ) 2 Di-2-propyl acrylate; branched (CH 2 C(CH 3 )(C(=O)OM)) 1-40 2-Propyl acrylate; (CH 2 CH(C(=O)NH 2 ) 1-40 Acrylamide; ((CH 2 CH(C(=O)NH 2 ) 1-40 ) 2 diacrylamide; branched (CH 2 CH(C(=O)NH 2 ) 1-40 Acrylamide; (CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 N-isopropylacrylamide; ((CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 ) 2 DiN-isopropylacrylamide; branched (CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 N-isopropylacrylamide; (CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 Hydroxyethylmethacrylamide; ((CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 ) 2 Dihydroxyethylmethacrylamide; branched (CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 Hydroxyethylmethacrylamide; (CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 2-Hydroxypropylmethacrylamide; ((CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40) Di-2-hydroxypropylmethacrylamide; branched (CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 2-Hydroxypropylmethacrylamide; (CH 2 C(-OSO 3 M)) 1-40 Vinyl sulfate salt; ((CH 2 C(-OSO 3 M)) 1-40 ) 2 Divinyl sulfate salt; branched (CH 2 C(-OSO 3 M)) 1-40 Vinyl sulfate salt; (CH 2 -4-C 6 H 6 SO 3 H) 1-40 4-Styrenesulfonic acid; ((CH 2 -4-C 6 H 6 SO 3 H) 1-40 ) 2 Di-4-styrenesulfonic acid; branched (CH 2 -4-C 6 H 6 SO 3 H) 1-40 4-Styrenesulfonic acid; (CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 4-Styrenesulfonate ammonium salt; ((CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 ) 2 Di-4-styrenesulfonate ammonium salt; branched (CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 4-Styrenesulfonate ammonium salt; (CH 2 C 6 H 6 SO 3 M) 1-40 4-Styrenesulfonate salt; ((CH 2 C 6 H 6 SO 3 M) 1-40 ) 2 Di-4-styrenesulfonate salt; branched (CH 2 C 6 H 6 SO 3 M) 1-40 4-Styrenesulfonate salt; (CHCH 2 NH 2 ) 1-40 Alkylamine; ((CHCH 2 NH 2 ) 1-40 ) 2 Dialkylamine; branched (CHCH 2 NH 2 ) 1-40 Alkylamine; (CHCH 2 NH 2 ·HCl) 1-40 Alkylamine hydrochloride; ((CHCH 2 NH 2 ·HCl) 1-40 ) 2 Dialkylamine hydrochloride; branched (CHCH 2 NH 2 ·HCl) 1-40 Alkylamine hydrochloride; (CH 2 N(CH 2 CH 2 N) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 )CH 2 CH 2 NHCH 2 ) 1-40 Ethyleneimine; ((CH 2 N(CH 2 CH 2 N) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 2 Diethyleneimine; (CH 2 N(CH 2 CH 2 N·HCl) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ·HCl) 2 )CH 2 CH 2 NHCH 2 ) 1-40 Ethyleneimine hydrochloride; ((CH 2 N(CH 2 CH 2 N·HCl) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ·HCl) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 2 Diethyleneimine hydrochloride; (CH 2 SO 3 M) 1-40 Vinyl sulfonate; ((CH 2 SO 3 M) 1-40 ) 2 Divinyl sulfonate; branched (CH 2 SO 3 M) 1-40 Vinyl sulfonate; (CH 2 CHC(=O)NH 2 )) 1-40 Acrylamide; ((CH 2 CHC(=O)NH 2 )) 1-40 ) 2 diacrylamide; branched (CH 2 CHC(=O)NH 2 )) 1-40 Acrylamide (CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 N-isopropylacrylamide; ((CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 ) 2 DiN-isopropylacrylamide; branched (CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 N-isopropylacrylamide; (CH 2 (cyclic CHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 Tetramethylpyrrolidium chloride; ((CH 2 (cyclic CHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 ) 2 Ditetramethylpyrrolidium chloride; branched (CH 2 (cyclic CHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 Tetramethylpyrrolidium chloride; SiH 2 (CH 2 CH 2 O) 1-40 Silyl ethylene glycol; branched SiH 2 ((CH 2 CH 2 O) 1-40 )silylethylene glycol; SiH((CH 2 CH 2 O) 1-40 ) 2 Silyldi(ethylene glycol); Si((CH 2 CH 2 O) 1-40 ) 3 Silyltri(ethylene glycol); SiH 2 (CH 2 COH) 1~40 Silyl vinyl alcohol; branched SiH 2 O(CH 2 COH) 1~40 Silyl vinyl alcohol; SiH((CH 2 COH) 1~40 ) 2 Silyldi(vinyl alcohol); Si((CH 2 COH) 1~40 ) 3 Silyltri(vinyl alcohol); SiH 2 (CH 2 COOH) 1-40 Silyl acrylate; branched SiH 2 (CH 2 COOH) 1-40 Silyl acrylate; SiH((CH 2 COOH) 1-40 ) 2 Silyldi(acrylic acid); Si((CH 2 COOH) 1-40 ) 2 Silyltri(acrylic acid); SiH 2 (CH 2 COOM) 1-40 Silyl acrylate; branched SiH 2 (CH 2 COOM) 1-40 Silyl acrylate; SiH((CH 2 COOM) 1-40 ) 2 Silyldi(acrylate); Si((CH 2 COOM) 1-40 ) 3 Silyltri(acrylate); SiH 2 (CH 2 C(CH 3 )(C(=O0H)) 1-40 Silylmethacrylic acid; branched SiH 2 (CH 2 C(CH 3 )(C(=O0H)) 1-40 Silylmethacrylic acid; SiH((CH 2 C(CH 3 )(C(=O0H)) 1-40 ) 2 Silyldi(methacrylic acid); Si((CH 2 C(CH 3 )(C(=O0H)) 1-40 ) 3 Silyltri(methacrylic acid); SiH 2 (CH 2 C(CH 3 )(C(=O0M)) 1-40 Silyl methacrylate; branched SiH 2 (CH 2 C(CH 3 )(C(=O0M)) 1-40 Silyl methacrylate; SiH((CH 2 C(CH 3 )(C(=O0M)) 1-40 ) 2 Silyldi(methacrylate); Si((CH 2 C(CH 3 )(C(=O0M)) 1-40 ) 3 Silyltri(methacrylate); SiH 2 (CH 2 C(CH 3 )(C(=O)OH)) 1-40 Silyl 2-propyl acrylate; branched SiH 2 (CH 2 C(CH 3 )(C(=O)OH)) 1-40 Silyl 2-propyl acrylic acid; SiH((CH 2 C(CH 3 )(C(=O)OH)) 1-40 ) 2 Silyldi(2-propylacrylic acid); Si((CH 2 C(CH 3 )(C(=O)OH)) 1-40 ) 3 Silyltri(2-propylacrylic acid); SiH 2 (CH 2 C(CH 3 )(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; branched SiH 2 (CH 2 C(CH 3 )(C(=O)OM)) 1-40 Silyl 2-propyl acrylate; SiH(((CH 2 C(CH 3 )(C(=O)OM)) 1-40) ) 2 Silyldi(2-propylacrylate); Si(((CH 2 C(CH 3 )(C(=O)OM)) 1-40) ) 2 Silyltri(2-propylacrylate); SiH 2 (CH 2 CH(C(=O)NH 2 ) 1-40 Silyl acrylamide; branched SiH 2 (CH 2 CH(C(=O)NH 2 ) 1-40 Silyl acrylamide; SiH((CH 2 CH(C(=O)NH 2 ) 1-40 ) 2 Silyldi(acrylamide); Si((CH 2 CH(C(=O)NH 2 ) 1-40 ) 3 Silyltri(acrylamide); SiH 2 (CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 Silyl N-isopropylacrylamide; branched SiH 2 O(CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 Silyl N-isopropylacrylamide; SiH((CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 ) 2 Silyldi(N-isopropylacrylamide); Si((CH 2 CH(C(=O)NH(CH(CH 3 ) 2 ))) 1-40 ) 3 Silyltri(N-isopropylacrylamide); SiH 2 (CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 Silylhydroxyethylmethacrylamide; branched SiH 2 (CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 Silylhydroxyethylmethacrylamide; SiH((CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 ) 2 Silyldi(hydroxyethylmethacrylamide); SiH((CH 2 CH(C(=ONHCH 2 CH 2 OH))) 1-40 ) 3 Silyltri(hydroxyethylmethacrylamide); SiH 2 (CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 Silyl 2-hydroxypropylmethacrylamide; branched SiH 2 (CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 Silyl 2-hydroxypropylmethacrylamide; SiH((CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 ) 2 Silyldi(2-hydroxypropylmethacrylamide); Si((CH 2 CH(C(=ONHCH 2 CH(OH)CH 3 ))) 1-40 ) 3 Silyltri(2-hydroxypropylmethacrylamide); SiH 2 (CH 2 C(-OSO 3 M)) 1-40 Silyl vinyl sulfate salt; branched SiH 2 (CH 2 C(-OSO 3 M)) 1-40 Silyl vinyl sulfate salt; SiH((CH 2 C(-OSO 3 M)) 1-40 ) 2 Silyldi(vinyl sulfate salt); SiH((CH 2 C(-OSO 3 M)) 1-40 ) 3 Silyltri(vinyl sulfate salt); SiH 2 (CH 2 -4-C 6 H 6 SO 3 H) 1-40 Silyl 4-styrenesulfonic acid; branched SiH 2 (CH 2 -4-C 6 H 6 SO 3 H) 1-40 Silyl 4-styrenesulfonic acid; SiH((CH 2 -4-C 6 H 6 SO 3 H) 1-40 ) 2 Silyldi(4-styrenesulfonic acid); SiH((CH 2 -4-C 6 H 6 SO 3 H) 1-40 ) 3 Silyltri(4-styrenesulfonic acid); SiH 2 (CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 Silyl 4-styrene sulfonate ammonium salt; branched SiH 2 (CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 Silyl 4-styrenesulfonate ammonium salt; SiH((CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 ) 2 Silyldi(4-styrenesulfonate ammonium salt); SiH((CH 2 -4-C 6 H 6 SO 3 NH 4 ) 1-40 ) 3 Silyltri(4-styrenesulfonate ammonium salt); SiH 2 (CH 2 C 6 H 6 SO 3 M) 1-40 Silyl 4-styrenesulfonate salt; branched SiH 2 (CH 2 C 6 H 6 SO 3 M) 1-40 Silyl 4-styrenesulfonate salt; SiH((CH 2 C 6 H 6 SO 3 M) 1-40 ) 2 Silyldi(4-styrenesulfonate salt); SiH((CH 2 C 6 H 6 SO 3 M) 1-40 ) 3 Silyltri(4-styrenesulfonate salt); SiH 2 (CHCH 2 NH 2 ) 1-40 Silylalkylamine; branched SiH 2 (CHCH 2 NH 2 ) 1-40 Silylalkylamine; SiH((CHCH 2 NH 2 ) 1-40 ) 2 Silyldi(alkylamine); SiH((CHCH 2 NH 2 ) 1-40 ) 3 Silyltri(alkylamine); SiH 2 (CHCH 2 NH 2 ·HCl) 1-40 Silylalkylamine hydrochloride; branched SiH 2 (CHCH 2 NH 2 ·HCl) 1-40 Silylalkylamine hydrochloride; SiH((CHCH 2 NH 2 ·HCl) 1-40 ) 2 Silyldi(alkylamine hydrochloride); SiH((CHCH 2 NH 2 ·HCl) 1-40 ) 3 Silyltri(alkylamine hydrochloride); SiH 2 (CH 2 N(CH 2 CH 2 N) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 )CH 2 CH 2 NHCH 2 ) 1-40 Silylethyleneimine; SiH((CH 2 N(CH 2 CH 2 N) 1-2 or SiH 2 O(CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 2 Silyldi(ethyleneimine); Si((CH 2 N(CH 2 CH 2 N) 1-2 or SiH 2 O(CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 3 Silyltri(ethyleneimine); SiH 2 (CH 2 N(CH 2 CH 2 N·HCl) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ·HCl) 2 )CH 2 CH 2 NHCH 2 ) 1-40 Silylethyleneimine hydrochloric acid; SiH((CH 2 N(CH 2 CH 2 N·HCl) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ·HCl) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 2 Silyldi(ethyleneimine hydrochloric acid); Si((CH 2 N(CH 2 CH 2 N·HCl) 1-2 Or (CH 2 CH 2 N(CH 2 CH 2 NH 2 ·HCl) 2 )CH 2 CH 2 NHCH 2 ) 1-40 ) 3 Silyltri(ethyleneimine hydrochloric acid); SiH 2 (CH 2 SO 3 M) 1-40 Silyl vinyl sulfonate; branched SiH 2 (CH 2 SO 3 M) 1-40 Silyl divinyl sulfonate; SiH((CH 2 SO 3 M) 1-40 ) 2 Silyldi(vinylsulfonate); Si((CH 2 SO 3 M) 1-40 ) 3 Silyltri(vinyl sulfonate); SiH 2 (CH 2 CHC(=O)NH 2 )) 1-40 Silyl acrylamide; branched SiH 2 (CH 2 CHC(=O)NH 2 )) 1-40 Silyl diacrylamide; SiH((CH 2 CHC(=O)NH 2 )) 1-40 ) 2 Silyldi(acrylamide); Si((CH 2 CHC(=O)NH 2 )) 1-40 ) 3 Silyltri(acrylamide); SiH 2 (CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 Silyl N-isopropylacrylamide; branched SiH 2 (CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 Silyl N-isopropylacrylamide; SiH((CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 ) 2 Silyldi(N-isopropylacrylamide); Si((CH 2 CH(C(=O)NHCH(CH 3 ) 2 )) 1-40 ) 3 Silyltri(N-isopropylacrylamide); SiH 2 (CH 2 (cyclic CHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 Silyltetramethylpyrrolidium chloride; branched SiH 2 (CH 2 (cyclic CHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 Silyltetramethylpyrrolidium chloride; SiH((CH 2 (cyclic SiH 2 OCHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 ) 2 Silyldi(tetramethylpyrrolidium chloride); and Si((CH 2 (cyclic SiH 2 OCHCH 2 N + (CH 3 ) 2 CH 2 CH·Cl - )CH 2 ) 1-40 ) 3 A novel polycarbonate polymer, wherein the polymer is selected from the group consisting of silyltri(tetramethylpyrrolidium chloride).

12. A biodegradable composition comprising a polycarbonate polymer selected from any one of claims 2 to 9.

13. In paragraph 12, The above biodegradable composition, A biodegradable composition further comprising at least one selected from the group consisting of a remote triggering pyrogen, an enzyme and a catalyst.

14. In paragraph 13, The above remote triggering pyrotechnic source is, A biodegradable composition comprising at least one selected from the group consisting of an infrared absorbing dye, magnetic particles and electric elements.

15. A biodegradable material for moisture blocking, manufactured from the biodegradable composition of Article 12.

16. A hydrolysis-resistant biodegradable material manufactured from the biodegradable composition of Article 12.

17. A biodegradable off-on material comprising a moisture-blocking biodegradable material of clause 15; and a hydrolysis-resistant biodegradable material of clause 16.

18. In paragraph 17, A biodegradable off-on material further comprising one or more biodegradable trigger layers.

19. A step of forming a moisture barrier layer on all or part of the surface of a hydrolysis mechanism biodegradable material, and then forming a hydrolysis-resistant layer on all or part of the surface of the moisture barrier layer to turn off the biodegradability of the hydrolysis mechanism biodegradable material; and A biodegradation off-on method, comprising: a step of turning on the biodegradability of the hydrolysis mechanism biodegradable material by applying an artificial stimulus to at least one selected from the group consisting of the moisture blocking layer and the hydrolysis resistant layer.

20. In paragraph 19, The above artificial stimulation is, A biodegradation off-on method, wherein at least one is selected from the group consisting of electromagnetic wave energy, thermal energy, ultrasonic energy, enzymes and catalysts.

21. In paragraph 19, The step of turning off the above biodegradability is: A biodegradation off-on method comprising: forming a moisture barrier layer on all or part of the surface of the hydrolysis mechanism biodegradable material; forming a biodegradation trigger layer on all or part of the surface of the moisture barrier layer; and forming a hydrolysis-resistant layer on all or part of the surface of the biodegradation trigger layer.

22. In paragraph 21, The step of turning on the above biodegradability is: A biodegradation off-on method that applies artificial stimulation to the above biodegradation trigger layer.

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