Process for synthesizing acetate bicyclo guanidine and catalysis synthesis for poly-lactide and poly-serine morpholine diketone

The technology of a serine morpholinedione and a synthesis method, which is applied in the field of medical biodegradable materials, can solve problems such as hidden safety hazards and removal of tin-containing catalysts, and achieves the effects of low production cost, high product yield and high biosafety.

Active Publication Date: 2008-12-10
无锡南大绿色环境友好材料技术研究院有限公司
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Problems solved by technology

In recent years, the research of scientists from all over the world has fully proved that stannous octoate is cytotoxic. Since the tin-containing catalyst cannot

Method used

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  • Process for synthesizing acetate bicyclo guanidine and catalysis synthesis for poly-lactide and poly-serine morpholine diketone
  • Process for synthesizing acetate bicyclo guanidine and catalysis synthesis for poly-lactide and poly-serine morpholine diketone
  • Process for synthesizing acetate bicyclo guanidine and catalysis synthesis for poly-lactide and poly-serine morpholine diketone

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Embodiment 1

[0028] The preparation of embodiment 1 bicyclic guanidine acetate

[0029] Bicyclic guanidine (TBD) 0.5127g (3.69mmol) is placed in the reactor, after repeating vacuum-filling argon three times, add 3ml distilled water in the reactor under argon atmosphere, after the bicyclic guanidine dissolves completely under room temperature, add to Add 0.21 mL (3.69 mmol) of acetic acid into the reactor, and react at 80° C. for 9 hours. The reaction was stopped and cooled to room temperature, the water was distilled off under reduced pressure, and vacuum-dried for 24 hours to obtain bicyclic guanidine acetate as a white solid with a yield of 88.0% and a product purity of ≥98%.

Embodiment 2

[0030] The preparation of embodiment 2 bicyclic guanidine acetate

[0031] Bicyclic guanidine (TBD) 0.5026g (3.61mmol) is placed in reactor, after repeating vacuum-filling argon three times, under argon atmosphere, add 3ml distilled water in reactor, after the complete dissolving of bicyclic guanidine at room temperature, add to Add 0.20 mL (3.61 mmol) of acetic acid into the reactor, and react at 80° C. for 7 hours. The reaction was stopped and cooled to room temperature, the water was distilled off under reduced pressure, and vacuum-dried for 24 hours to obtain bicyclic guanidine acetate as a white solid with a yield of 90.5% and a product purity of ≥98%.

Embodiment 3

[0032] Example 3 Synthesis of poly-L-lactide catalyzed by bicyclic guanidine acetate (this example and the following reaction conditions for synthesizing polylactide are also applicable to polyserine morpholine dione, no further examples, the same below)

[0033] Weigh 1.000g (6.90mmol) of L-lactide and 0.0138g (0.0690mmol) of bicyclic guanidine acetate respectively and place them in a reaction kettle. React in the bath for 50min. After the reaction, dissolve the polymer with 3 mL of acetone, slowly drop it into distilled water to precipitate the polymer, remove the distilled water by filtration, and dry the obtained solid under vacuum at 40° C. for 24 hours. Yield: 87.09%, Mn=3.9×10 4 , PDI=1.15.

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Abstract

The invention relates to an acetate bicyclic guanidine, a synthesizing method thereof and a synthesis of a polylactide and a polyserine morpholine dione by catalysis. The acetate bicyclic guanidine has the above structure and is synthesized by a direct reaction of bicyclic guanidine and acetic acid in a catalyst-free aqueous solution. In the invention, the acetate bicyclic guanidine is adopted as a catalyst to catalyze a bulk activity of L-lactide (LLA), D,L-lactide (DLLA) or (3S)-3- benzyloxymethyl-6-methyl-morpholine dione (BMMD) to perform ring opening polymerization reaction , thereby synthesizing a poly L-lactide (PLLA) and a poly D,L-lactide (PDLLA) with a number average degree of polymerization of between 120 and 280 and narrow molecular weight distribution and polyserine morpholine dione with a number average degree of polymerization of between 120 and 150. PBMMD can be used for preparing a lactic acid-serine copolymer. The acetate bicyclic guanidine as the catalyst is a nonmetallic and nontoxic organic compound; the method has low production cost, simple process operation, no pollution, a high product yield of more than or equal to 95 percent and a high product purity of more than or equal to 98 percent; and a synthesized biodegradable polymer has high biological safety.

Description

【Technical field】 [0001] The invention belongs to the technical field of medical biodegradable materials, and relates to a catalytic synthesis method of medical biodegradable polymers. 【Background technique】 [0002] In recent years, with the rapid development of medicine and biomedical science, the demand for medical biodegradable materials with excellent biocompatibility and biosafety is increasing rapidly at home and abroad. The synthesis of biodegradable polymers (polylactic acid, polyglycolic acid, lactic acid amino acid copolymer, etc.) requires the use of catalysts, and the synthesis of commercial pharmaceutical degradation polymers uses stannous octoate (tin 2-ethylhexanoate) as a catalyst. In recent years, the research of scientists from all over the world has fully proved that stannous octoate is cytotoxic. Since the tin-containing catalyst cannot be completely removed from the polymer after polymerization, this kind of biodegradable polymer can be used as human me...

Claims

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Application Information

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IPC IPC(8): C07D487/04C08G63/87C08G63/08C08G69/44
Inventor 李弘焦洁平孔丽君徐杰
Owner 无锡南大绿色环境友好材料技术研究院有限公司
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