An organic multi-hydrogen bond non-metallic catalyst for polymerization and its preparation method and application

Abstract

The present invention relates to an organic multiple hydrogen bond non-metal catalyst for polymerization and a preparation method and application thereof, and relates to the technical field of catalyst synthesis. The structure of the organic multiple hydrogen bond non-metal catalyst of the present invention is shown in formula (1) or formula (2). The preparation method of the organic multiple hydrogen bond non-metal catalyst of the present invention is to obtain a catalyst by subjecting a reaction raw material TA to a nucleophilic addition reaction with a compound K containing a cyanate group. The organic multiple hydrogen bond non-metal catalyst of the present invention has the characteristics of simple preparation, modular adjustment, high yield, etc. The organic multiple hydrogen bond non-metal catalyst of the present invention exhibits excellent catalytic activity in catalyzing the ring-opening polymerization of N-carboxyl intracyclic acid anhydride to obtain poly-polypeptide, the ring-opening polymerization of O-carboxyl intracyclic acid anhydride to obtain polyester, the ring-opening polymerization of β-butyrolactone to obtain polyester, the ring-opening polymerization of epoxide to obtain polyether, the ring-opening polymerization of cyclic thioether to obtain polythioether, the ring-opening copolymerization of oxirane and cyclic acid anhydride to obtain polyester, etc.

Description

Technical Field

[0001] The present invention relates to the technical field of catalyst synthesis, and in particular to an organic multiple hydrogen bond non-metal catalyst for polymerization, a preparation method and application thereof. Background Art

[0002] In recent years, organic catalysts have attracted much attention in the fields of organic chemistry, polymer chemistry and the preparation of polymer materials due to their advantages of simple synthesis, low price and low biological toxicity. Among them, hydrogen-bonded organic catalysts have been widely studied by many scholars around the world due to their high selectivity, strong controllability and easy structural adjustment. Hydrogen-bonded organic catalytic systems can catalyze the ring-opening polymerization of cyclic lactones, cyclic carbonates, and morpholine-2,5-dione, and the copolymerization of epoxides / cyclic anhydrides and epoxides / carbon oxysulfide to synthesize polyesters, polycarbonates, polyester amides and polythiocarbonates, thereby realizing the application of the resulting materials in packaging, drug delivery, tissue engineering, microelectronics processing and other fields.

[0003] The peptide synthesized by ring-opening polymerization of N-carboxylic anhydride is a protein mimetic with a wide range of biomedical applications. Due to its unique secondary structure, it has received increasing attention. In recent years, many outstanding works have reported highly active or highly selective metal or non-metal catalyst systems for the ring-opening polymerization of N-carboxylic anhydride to obtain peptides with clear structures. In 2016, Lu [Biomacromolecules 2016, 17, 891-896] reported the ring-opening polymerization of N-carboxylic anhydride catalyzed by trimethylsilylphenylthioester, and obtained peptides with controllable molecular weight and very narrow distribution, showing good selectivity. In 2019, Cheng [J.Am.Chem.Soc.2019, 141, 8680-8683] reported that the ring-opening polymerization of N-carboxylic anhydride in low-polarity solvents has a spiral-induced self-acceleration phenomenon, which can complete the complete conversion of monomers in a very short time to obtain high molecular weight peptides, showing high polymerization activity. However, the above-mentioned organic catalytic systems cannot take into account both the activity and controllability of polymerization.

[0004] Tao [Angew.Chem.Int.Ed.2021,60,6003-6012; Nature Synthesis 2022,1,815–823] reported in 2021 and 2022 respectively the anionic polymerization of O-carboxylic anhydride and cationic polymerization of vinyl ether monomers by anion-bonded catalysis, showing high polymerization activity and selectivity, and universal applicability. Due to the high activity of the terminal anion, the anionic ring-opening polymerization of N-carboxylic anhydride monomers usually has multiple side reactions and cannot obtain a polymer with a clear structure. Its anionic ring-opening polymerization has not yet been achieved. There is a strong anionic binding effect between hydrogen bond donor catalysts and anionic species. Therefore, organic catalysts with multiple hydrogen bonds are designed. Through multi-site interactions with anionic species, the anionic active species can be stabilized while retaining the polymerization activity, which is expected to achieve high activity and high selectivity Anionic ring-opening polymerization of N-carboxylic anhydride monomers. Therefore, how to design multi-hydrogen bond organic catalysts to achieve high activity and high selectivity in polymerization is the current research and development focus. Summary of the invention

[0005] The present invention aims to solve the technical problem that the existing organic catalytic system cannot simultaneously achieve high activity and high selectivity in polymerization, and provides an organic multi-hydrogen bond non-metal catalyst for polymerization, and a preparation method and application thereof. The organic multi-hydrogen bond non-metal catalyst of the present invention has the characteristics of simple preparation, modular adjustment, high yield, etc., and is combined with an initiator to catalyze the ring-opening polymerization of N-carboxyl cyclic anhydride to obtain poly-polypeptide, catalyze the ring-opening polymerization of O-carboxyl cyclic anhydride to obtain polyester, catalyze the ring-opening polymerization of β-butyrolactone to obtain polyester, catalyze the ring-opening polymerization of epoxide to obtain polyether, catalyze the ring-opening polymerization of cyclic thioether to obtain polythioether, catalyze the ring-opening copolymerization of alkylene oxide and cyclic anhydride to obtain polyester, and catalyze the copolymerization of epoxide and carbon dioxide to obtain aliphatic polycarbonate, and exhibits excellent catalytic activity.

[0006] In order to solve the above technical problems, the technical solutions of the present invention are as follows:

[0007] The present invention provides an organic multi-hydrogen bond non-metal catalyst for polymerization, the general structural formula of which is shown in Formula (1) or Formula (2):

[0008]

[0009] In formula (1), X1, X2, and X3 are each independently selected from oxygen or sulfur atoms:

[0010] In formula (1) to (2), l, m, and n are independently selected from integers of 0 to 50;

[0011] In formulas (1) to (2), R1 to R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aromatic, substituted or unsubstituted C3-C30 heterocyclic, and substituted or unsubstituted C5-C30 heteroaromatic groups;

[0012] When the above groups are substituted with substituents, the substituents are selected from one or more of halogen atoms, branched or straight-chain alkyl groups having 1 to 20 carbon atoms, branched or straight-chain alkoxy groups having 1 to 20 carbon atoms, branched or straight-chain cycloalkyl groups having 3 to 20 carbon atoms, aromatic groups having 6 to 20 carbon atoms, and heteroaromatic groups having 5 to 20 carbon atoms.

[0013] In the above technical solution, the substituent groups independently selected from R1-R6 also contain one or more of O, S, N, Si and P atoms.

[0014] In the above technical solution, the organic multiple hydrogen bond non-metal catalyst is selected from any one of the following structures:

[0015]

[0016]

[0017]

[0018] The present invention also provides a method for preparing an organic multiple hydrogen bond non-metal catalyst for polymerization, comprising the following steps:

[0019] The reaction raw material TA is subjected to a nucleophilic addition reaction with a compound K containing a cyanate group to obtain the organic multiple hydrogen bond non-metal catalyst;

[0020] The structure of the reaction raw material TA is as follows:

[0021]

[0022] N and H represent nitrogen and hydrogen atoms respectively;

[0023] Wherein, l, m, and n are independently selected from any integer between 0 and 50;

[0024] The structure of the compound K is selected from one of the following structural formulas:

[0025] R-NCS R-NCO R-NHCCOCOCOR7

[0026] Among them, N, C, S, O, and H represent nitrogen, carbon, sulfur, oxygen, and hydrogen atoms respectively;

[0027] R, R7 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aromatic, substituted or unsubstituted C3-C30 heterocyclic, and substituted or unsubstituted C5-C30 heteroaromatic groups;

[0028] When the above groups are substituted by substituents, the substituents are selected from one or more of halogen atoms, branched or straight-chain hydrocarbon groups having 1 to 20 carbon atoms, branched or straight-chain alkoxy groups having 1 to 20 carbon atoms, branched or straight-chain cycloalkyl groups having 3 to 20 carbon atoms, aromatic groups having 6 to 20 carbon atoms, and heteroaromatic groups having 5 to 20 carbon atoms.

[0029] In the above technical solution, the temperature of the nucleophilic addition reaction is 25-100° C., and the reaction time is 6-48 hours.

[0030] The present invention also provides an application of an organic multiple hydrogen-bonded non-metallic catalyst, which is used to catalyze the ring-opening polymerization of N-carboxyl cyclic acid anhydride to obtain polypeptides, catalyze the ring-opening polymerization of O-carboxyl cyclic acid anhydride to obtain polyesters, catalyze the ring-opening polymerization of β-butyrolactone to obtain polyesters, catalyze the ring-opening polymerization of epoxides to obtain polyethers, catalyze the ring-opening polymerization of cyclic thioethers to obtain polythioethers, catalyze the ring-opening copolymerization of alkylene oxides and cyclic acid anhydrides to obtain polyesters, or catalyze the copolymerization of epoxides and carbon dioxide to obtain aliphatic polycarbonates.

[0031] In the above technical solution, when the organic multi-hydrogen-bonded non-metal catalyst is used to catalyze the ring-opening polymerization of N-carboxyl intracyclic acid anhydride to obtain a polypolypeptide, the N-carboxyl intracyclic acid anhydride is selected from at least one of the following structures:

[0032]

[0033] The molar ratio of the N-carboxyl intracyclic acid anhydride, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 25-1000:0.7:1, and the polymerization temperature is 25°C.

[0034] In the above technical scheme, when the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of O-carboxyl intracyclic acid anhydride to obtain polyester, the molar ratio of the O-carboxyl intracyclic acid anhydride, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 20-1000:0.7:1, and the polymerization reaction temperature is 25-80°C.

[0035] In the above technical scheme, when the organic multiple hydrogen bond non-metal catalyst is used to catalyze the ring-opening polymerization of β-butyrolactone to obtain polyester, the molar ratio of the β-butyrolactone, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 100-500:1:0.5, and the polymerization reaction temperature is 60-100°C.

[0036] In the above technical scheme, when the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of epoxide to obtain polyether, the epoxide is at least one of ethylene oxide, propylene oxide, epichlorohydrin, butylene oxide, isobutylene oxide, cyclopentane oxide, 3,4-epoxytetrahydrofuran, cyclohexene oxide, 4-vinyl cyclohexene oxide, styrene oxide and limonene oxide; the molar ratio of the epoxide, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 100 to 10000:1:1, and the polymerization reaction temperature is -20 to 60°C;

[0037] When the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of cyclic sulfide to obtain polysulfide, the cyclic sulfide is at least one of ethylene sulfide, propylene sulfide, chloropropane sulfide, butylene sulfide, isobutylene sulfide, cyclopentane sulfide, 3,4-tetrahydrofuran sulfide, cyclohexyl sulfide, 4-vinyl cyclohexyl sulfide, styrene sulfide and limonene sulfide; the molar ratio of the cyclic sulfide, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 100 to 10000:1:1, and the polymerization reaction temperature is -20 to 60°C;

[0038] When the organic multiple hydrogen bond non-metal catalyst is used to catalyze the ring-opening copolymerization of alkylene oxide and cyclic acid anhydride to obtain polyester, the molar ratio of the cyclic acid anhydride, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 25-10000:0.7:1, and the temperature of the polymerization reaction is 25-90°C; when the organic multiple hydrogen bond non-metal catalyst is used to catalyze the copolymerization of epoxide and carbon dioxide to obtain aliphatic polycarbonate, the molar ratio of the epoxide, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 100-10000:0.7:1, and the temperature of the polymerization reaction is 25-90°C.

[0039] The beneficial effects of the present invention are:

[0040] The organic multiple hydrogen-bond non-metal catalyst of the present invention fully exerts the multiple hydrogen-bond effect in its molecule by covalently linking multiple sites. The catalyst of the present invention can be obtained quantitatively and efficiently, has the characteristics of simple preparation, modular adjustment, high yield, etc. The organic multiple hydrogen-bond non-metal catalyst can be used to catalyze the ring-opening polymerization of N-carboxyl intracyclic acid anhydride to obtain polypolypeptide, catalyze the ring-opening polymerization of O-carboxyl intracyclic acid anhydride to obtain polyester, catalyze the ring-opening polymerization of β-butyrolactone to obtain polyester, catalyze the ring-opening polymerization of epoxide to obtain polyether, catalyze the ring-opening polymerization of cyclic thioether to obtain polythioether, catalyze the ring-opening copolymerization of alkylene oxide and cyclic acid anhydride to obtain polyester, and catalyze the copolymerization of epoxide and carbon dioxide to obtain aliphatic polycarbonate, and has extremely high catalytic activity and excellent selectivity.

[0041] A very innovative point of the present invention is that the organic multiple hydrogen bond non-metal catalyst in the present invention catalyzes the ring-opening polymerization of N-carboxyl cyclic anhydride following the "living anion polymerization" mechanism, and a highly active anion at the end of the growing chain is obtained by an anion initiator. There is a dynamic and reversible anion binding effect between the organic multiple hydrogen bond non-metal catalyst and the anion at the end of the growing chain, which avoids the generation of highly alkaline species, and can ensure the growth activity while stabilizing the highly active anion, thereby achieving high activity and high selectivity of the polymerization. DETAILED DESCRIPTION

[0042] The present invention is specifically described below through specific embodiments:

[0043] Example 1: Synthesis of Catalyst 1:

[0044]

[0045] 3,5-bis(trifluoromethyl)phenyl isothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 1 with a yield of 90%. Catalyst 1: 1 H NMR (400MHz, DMSO-d6): δ10.16(s,3H),8.28(s,6H),8.10(s,3H),7.63(s,3H),3.74(b,6H),2.91(t,6H).

[0046] Example 2: Synthesis of Catalyst 2:

[0047]

[0048] 4-(Trifluoromethyl)phenyl isothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 2 with a yield of 90%. Catalyst 2: 1 H NMR (400MHz, DMSO-d6): δ9.95(s,3H),7.98(s,3H),7.78(d,6H),7.63(d,6H),3.68(b,6H),2.82(b,6H).

[0049] Example 3: Synthesis of Catalyst 3:

[0050]

[0051] 2-(Trifluoromethyl)phenyl isothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 3 with a yield of 90%. Catalyst 3: 1 H NMR (400MHz, DMSO-d6): δ9.16(s,3H),7.78(s,3H),7.67(m,6H),7.54(d,3H),7.45(t,3H),3.56(d,6H),2.70(t,6H).

[0052] Example 4: Synthesis of Catalyst 4:

[0053]

[0054] 3-(Trifluoromethyl)phenyl isothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 4 with a yield of 90%. Catalyst 4: 1 H NMR (400MHz, DMSO-d6): δ9.82(b,3H),7.97(s,6H),7.69(d,3H),7.52(t,3H),7.40(d,3H),3.65(b,6H),2.80(b,6H).

[0055] Example 5: Synthesis of Catalyst 5:

[0056]

[0057] Phenyl isothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 5 with a yield of 90%. Catalyst 5: 1 H NMR (400MHz, DMSO-d6): δ9.60(s,3H),7.63(s,3H),7.39(d,6H),7.31(t,6H),7.10(t,3H),3.59(b,6H),2.73(t,6H).

[0058] Example 6: Synthesis of Catalyst 13:

[0059]

[0060] 3,5-bis(trifluoromethyl)phenylisothiocyanate (3.3 eq) and 3 mL of dichloromethane were added to a 10 mL round-bottom flask. Triamine ethylenediamine (1.0 eq) was added dropwise at room temperature. The reaction progress was monitored by thin layer chromatography. After about 12 h, the reaction was completed to obtain a white solid, which was filtered and purified by washing with dichloromethane to obtain the target catalyst 13 with a yield of 90%. Catalyst 13: 1 HNMR (400MHz, DMSO-d6): δ9.31(s,3H),8.03(s,6H),7.43(s,3H),6.45(t,3H),3.30(s,6H),2.70(t,6H).

[0061] Example 7: Synthesis of Catalyst 21:

[0062]

[0063] To a 25 mL round-bottom flask, 3,5-bis(trifluoromethyl)aniline (1.0 eq) and 10 mL of methanol were added, followed by 3,4-dihydroxy-3-cyclobutene-1,2-dione (1.0 eq) and zinc trifluoromethanesulfonate. The mixture was refluxed at 65 °C for 36 h to obtain a light yellow solid. The solid was filtered, washed and purified with methanol, and the product was directly used for the next step.

[0064] Add 21-1 (3.3 eq) and 3 mL of methanol to a 10 mL round-bottom flask, add triamine ethylenediamine (1.0 eq) dropwise, and reflux at 65 ° C for 36 h to obtain a white solid, which is filtered and purified by washing with methanol to obtain the target catalyst 21 with a yield of 85%. Catalyst 21: 1 H NMR (400MHz, DMSO-d6): δ10.08(br,3H),8.92(s,6H),8.02(s,3H),6.60(t,3H),3.53(s,6H),2.81(t,6H).

[0065] The R groups in the corresponding formulas 1 and 2 in the above embodiments can also be replaced by other groups listed above, and can be prepared according to the above embodiments, which will not be listed one by one here.

[0066] Application Example 1: Catalytic N-carboxyl intracyclic acid anhydride ring-opening polymerization to obtain polypeptide

[0067] In the glove box, weigh or measure the catalyst and initiator PhSNa into the reaction bottle (the reaction bottle was evacuated, baked, cooled, and nitrogen-filled in advance, and the process was repeated three times), and then add L-glutamic acid N-carboxyl cyclic anhydride (GluNCA). After the reaction bottle is sealed, react at 25°C. After a certain period of polymerization, take the reaction solution to measure the nuclear magnetic resonance to characterize the conversion rate of the monomer and the selectivity of the product. After drying, the target polypeptide can be obtained. The molecular weight is determined by gel permeation chromatography (Waters2414), and the structure is determined by nuclear magnetic resonance spectroscopy (Bruker AV-500). The test results are shown in Table 1.

[0068] Application Example 2: Catalytic O-carboxyl ring anhydride ring opening to obtain polypeptide

[0069] In the glove box, weigh or measure the catalyst and initiator PhSNa into the reaction bottle (the reaction bottle was evacuated, baked, cooled, and nitrogen-filled in advance, and the process was repeated three times), and then add L-phenylalanine O-carboxyl ring anhydride (PheOCA). After the reaction bottle is sealed, react at 25°C. After a certain period of polymerization, take the reaction solution to measure the nuclear magnetic resonance to characterize the conversion rate of the monomer and the selectivity of the product. After drying, the target polyester can be obtained. The molecular weight is determined by gel permeation chromatography (Waters2414), and the structure is determined by nuclear magnetic resonance spectroscopy (Bruker AV-500). The test results are shown in Table 1.

[0070] Application Examples 3-6:

[0071] The reaction process is the same as that of Application Example 1. The differences between Application Examples 3-6 and Application Example 1 are shown in Table 1.

[0072] Table 1

[0073]

[0074] 1 Monomer types: L-benzyl glutamic acid N-carboxyl ring anhydride (Bn-GluNCA), L-phenylalanine N-carboxyl ring anhydride (PheNCA), L-benzyl serine N-carboxyl ring anhydride (Bn-SerNCA) PheOCA (L-phenylalanine O-carboxyl ring anhydride), propylene oxide (PO), phthalic anhydride (PA), cyclohexene oxide (CHO). 2 Initiator: sodium thiophenolate [PhSNa], sodium phenolate [PhONa], bis(triphenylphosphorane) chloride [PPNCl]. 3 The molar ratio of [monomer]:[catalyst]:[initiator]. 4 Mn: number average molecular weight, determined by gel permeation chromatography. 5 PDI: Molecular weight distribution, determined by gel permeation chromatography.

[0075] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.

Claims

1. A method for using an organic multi-hydrogen-bonded non-metallic catalyst to catalyze the ring-opening polymerization of N-carboxyl intracyclic acid anhydride to obtain a polypeptide, catalyze the ring-opening polymerization of O-carboxyl intracyclic acid anhydride to obtain a polyester, catalyze the ring-opening polymerization of β-butyrolactone to obtain a polyester, catalyze the ring-opening polymerization of epoxide to obtain a polyether, catalyze the ring-opening polymerization of cyclic thioether to obtain a polythioether, catalyze the ring-opening copolymerization of alkylene oxide and cyclic acid anhydride to obtain a polyester, or catalyze the copolymerization of epoxide and carbon dioxide to obtain an aliphatic polycarbonate, characterized in that: When the organic multiple hydrogen bond non-metal catalyst is used for catalytic polymerization, a highly active anion at the end of the growing chain is obtained through an anion initiator, and a dynamic and reversible anion binding effect exists between the organic multiple hydrogen bond non-metal catalyst and the anion at the end of the growing chain; The general structural formula of the organic multiple hydrogen bond non-metal catalyst is shown in Formula (1) or Formula (2): In formula (1), X1, X2, and X3 are each independently selected from oxygen or sulfur atoms: In formula (1) to (2), l, m, and n are independently selected from integers of 0 to 50; In formulas (1) to (2), R1-R6 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aromatic, substituted or unsubstituted C3-C30 heterocyclic, and substituted or unsubstituted C5-C30 heteroaromatic groups; the substituted groups independently selected from R1-R6 further contain one or more of O, S, N, Si and P atoms; When the above groups are substituted with substituents, the substituents are selected from one or more of halogen atoms, branched or straight-chain alkyl groups having 1 to 20 carbon atoms, branched or straight-chain alkoxy groups having 1 to 20 carbon atoms, branched or straight-chain cycloalkyl groups having 3 to 20 carbon atoms, aromatic groups having 6 to 20 carbon atoms, and heteroaromatic groups having 5 to 20 carbon atoms.

2. The method according to claim 1, characterized in that The organic multiple hydrogen bond non-metal catalyst is selected from any one of the following structures:

3. The method according to claim 1, characterized in that The method for preparing the organic multiple hydrogen bond non-metal catalyst comprises the following steps: The reaction raw material TA is subjected to a nucleophilic addition reaction with a compound K containing a cyanate group to obtain the organic multiple hydrogen bond non-metal catalyst; The structure of the reaction raw material TA is as follows: N and H represent nitrogen and hydrogen atoms respectively; Wherein, l, m, and n are independently selected from any integer between 0 and 50; The structure of the compound K is selected from one of the following structural formulas: R-NCSR-NCO R-NHCCOCOCOR7 Among them, N, C, S, O, and H represent nitrogen, carbon, sulfur, oxygen, and hydrogen atoms respectively; R and R7 are each independently selected from one or more combinations of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aromatic, substituted or unsubstituted C3-C30 heterocyclic, and substituted or unsubstituted C5-C30 heteroaromatic groups; When the above groups are substituted with substituents, the substituents are selected from one or more of halogen atoms, branched or straight-chain alkyl groups having 1 to 20 carbon atoms, branched or straight-chain alkoxy groups having 1 to 20 carbon atoms, branched or straight-chain cycloalkyl groups having 3 to 20 carbon atoms, aromatic groups having 6 to 20 carbon atoms, and heteroaromatic groups having 5 to 20 carbon atoms.

4. The method according to claim 3, characterized in that The temperature of the nucleophilic addition reaction is 25°C-100°C, and the reaction time is 6-48h.

5. The method according to claim 1, characterized in that When the organic multi-hydrogen-bonded non-metal catalyst is used to catalyze the ring-opening polymerization of N-carboxyl intracyclic acid anhydride to obtain a polypolypeptide, the N-carboxyl intracyclic acid anhydride is selected from at least one of the following structures: The molar ratio of the N-carboxyl intracyclic acid anhydride, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 25-1000:0.7:1, and the polymerization temperature is 25°C.

6. The method according to claim 1, characterized in that When the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of O-carboxyl intracyclic acid anhydride to obtain polyester, the molar ratio of the O-carboxyl intracyclic acid anhydride, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 20-1000:0.7:1, and the polymerization reaction temperature is 25-80°C.

7. The method according to claim 1, characterized in that When the organic multiple hydrogen bond non-metal catalyst is used to catalyze the ring-opening polymerization of β-butyrolactone to obtain polyester, the molar ratio of the β-butyrolactone, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 100-500:1:0.5, and the polymerization reaction temperature is 60-100°C.

8. The method according to claim 1, characterized in that: When the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of epoxide to obtain polyether, the epoxide is at least one of ethylene oxide, propylene oxide, epichlorohydrin, butylene oxide, isobutylene oxide, cyclopentane oxide, 3,4-epoxytetrahydrofuran, cyclohexene oxide, 4-vinyl cyclohexene oxide, styrene oxide and limonene oxide; the molar ratio of the epoxide, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 100 to 10000:1:1, and the polymerization reaction temperature is -20 to 60°C; When the organic multiple hydrogen-bonded non-metallic catalyst is used to catalyze the ring-opening polymerization of the cyclic sulfide to obtain the polysulfide, the cyclic sulfide is at least one of ethylene sulfide, propylene sulfide, chloropropane sulfide, butylene sulfide, isobutylene sulfide, cyclopentane sulfide, 3,4-tetrahydrofuran sulfide, cyclohexyl sulfide, 4-vinyl cyclohexyl sulfide, styrene sulfide and limonene sulfide; the molar ratio of the cyclic sulfide, the organic multiple hydrogen-bonded non-metallic catalyst and the added initiator is 100 to 10000:1:1, and the polymerization reaction temperature is -20 to 60°C; When the organic multi-hydrogen-bonded non-metallic catalyst is used to catalyze the polyester obtained by the ring-opening copolymerization of alkylene oxide and cyclic acid anhydride, the molar ratio of the cyclic acid anhydride, the organic multi-hydrogen-bonded non-metallic catalyst and the added initiator is 25-10000:0.7:1, and the polymerization temperature is 25-90°C; When the organic multiple hydrogen bond non-metal catalyst is used to catalyze the copolymerization of epoxide and carbon dioxide to obtain aliphatic polycarbonate, the molar ratio of the epoxide, the organic multiple hydrogen bond non-metal catalyst and the added initiator is 100-10000:0.7:1, and the polymerization temperature is 25-90°C.

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