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Vinyl amino acid (ester) polymer and preparation method thereof

An amino acid and vinyl technology, applied in the field of biofunctional polymer materials, can solve the problems of poor solubility and limited application range of polyamino acids

Active Publication Date: 2013-05-29
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The polyamino acids (esters) prepared by the condensation reaction of groups (amino and carboxyl groups) have poor solubility, only a few polyamino acids are soluble in water, most of them are hydrophobic, and there are not many that can be dissolved in general solvents. Applications are limited

Method used

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  • Vinyl amino acid (ester) polymer and preparation method thereof
  • Vinyl amino acid (ester) polymer and preparation method thereof
  • Vinyl amino acid (ester) polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Weigh 10 grams (37mmol) N-acetyl-L-tyrosine ethyl ester into 100mL acetone, add 54mmol K 2 CO 3 and 37 mmol of 6-bromo-1-hexene, under nitrogen protection, reacted at 50°C for 3 days to obtain 5.8 g of 1-hexenyl-N-acetyl-L-tyrosine ethyl ester.

[0042] 1 H NMR (CDCl 3 ): δ=6.93(d, 2H, 2HC=), 6.75(d, 2H, 2HC=), 5.95(d, 1H, NH), 5.80(m, 1H, HC=CH 2 ), 4.96 (m, 2H, HC=CH 2 ), 4.78(q, 1H, CH), 4.13(q, 2H, CH 2 ), 3.88(t, 2H, CH 2 ), 3.09 (dd, 1H, CH a -CH b ), 2.94 (dd, 1H, CH a -CH b ), 2.10 (m, 2H, CH 2 ), 1.96 (s, 3H, COCH 3 ), 1.75 (m, 2H, CH 2 ), 1.53 (m, 2H, CH 2 ), 1.22(t, 3H, CH 3 ).

[0043] Add 20mmol of 1-hexenyl-N-acetyl-L-tyrosine ethyl ester to 50mL of butyl acetate, then add 0.2mmol of initiator AIBN, under nitrogen protection, heat up to 60°C and react for 6 hours, and the reaction ends. The product was washed with ethanol and water and dried to obtain 4.2 g of poly-1-hexenyl-N-acetyl-L-tyrosine ethyl ester. m W =8.5×10 4 , The softening ...

Embodiment 2

[0046] Weigh 10 grams (37mmol) N-acetyl-L-tyrosine ethyl ester into 100mL acetone, add 54mmol K 2 CO 3 and 37 mmol of 8-bromo-1-octene, under nitrogen protection, reacted at 50°C for 3 days to obtain 5.8 g of 1-octenyl-N-acetyl-L-tyrosine ethyl ester.

[0047] 1 H NMR (CDCl 3 ): δ=6.93(d, 2H, 2HC=), 6.75(d, 2H, 2HC=), 5.95(d, 1H, NH), 5.80(m, 1H, HC=CH 2 ), 4.96 (m, 2H, HC=CH 2 ), 4.78(q, 1H, CH), 4.13(q, 2H, CH 2 ), 3.88(t, 2H, CH 2 ), 3.09 (dd, 1H, CH a -CH b ), 2.94 (dd, 1H, CH a -CH b ), 2.10 (m, 2H, CH 2 ), 1.96 (s, 3H, COCH 3 ), 1.75 (m, 2H, CH 2 ), 1.53-1.25 (m, 8H, CH 2 ), 1.22(t, 3H, CH 3 ).

[0048] Add 20mmol of 1-octenyl-N-acetyl-L-tyrosine ethyl ester to 50mL of nonyl acetate, then add 0.6mmol of initiator AIBN, under nitrogen protection, heat up to 65 degrees and react for 8 hours, and the reaction is completed. The product was washed with ethanol and water and dried to obtain 4.5 g of poly-1-octenyl-N-acetyl-L-tyrosine ethyl ester. m W =3.5×10 ...

Embodiment 3

[0051] Weigh 10 grams (37mmol) N-acetyl-L-tyrosine ethyl ester into 100mL acetone, add 54mmol K 2 CO 3 and 37 mmol of 4-bromo-1-butene, under nitrogen protection, reacted at 50°C for 3 days to obtain 4.8 g of 1-butenyl-N-acetyl-L-tyrosine ethyl ester.

[0052] 1 H NMR (CDCl 3 ): δ=6.93(d, 2H, 2HC=), 6.75(d, 2H, 2HC=), 5.95(d, 1H, NH), 5.80(m, 1H, HC=CH 2 ), 4.96 (m, 2H, HC=CH 2 ), 4.78(q, 1H, CH), 4.13(q, 2H, CH 2 ), 3.88(t, 2H, CH2 ), 3.09 (dd, 1H, CH a -CH b ), 2.94 (dd, 1H, CH a -CH b ), 2.10 (m, 2H, CH 2 ), 1.96 (s, 3H, COCH 3 ), 1.75 (m, 2H, CH 2 ), 1.22(t, 3H, CH 3 ).

[0053] Add 20mmol of 1-butenyl-N-acetyl-L-tyrosine ethyl ester to 100mL of toluene, then add 0.9mmol of initiator AIBN, protect with nitrogen, heat up to 65°C and react for 8 hours, and finish the reaction with ethanol The product was washed with water and dried to obtain 4.1 g of poly-1-butenyl-N-acetyl-L-tyrosine ethyl ester. m W =2.5×10 4 , The softening point is 80 degrees.

[0054] ...

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Abstract

The invention relates to a preparation method of a vinyl amino acid (ester) polymer and belongs to the field of high molecular materials. The method comprises the following steps of preparing the vinyl amino acid (ester) polymer and a vinyl amino acid (ester) copolymer and also preparing a copolymer of vinyl amino acid (ester) and other vinyl monomers under the protection of inert gases, in the presence of an initiator or a catalyst and by using the vinyl amino acid (ester) as a monomer. The preparation method and the process are simple in operation; and the product is applicable in the fieldof biological function high molecular materials or other fields. The method is an effective approach of high-efficiency utilization and high-value conversion of biomass resources and fossil resources.

Description

Technical field: [0001] The invention belongs to the field of biofunctional polymer materials, and in particular relates to a vinyl amino acid (ester), a vinyl amino acid polymer, a vinyl amino acid ester polymer or a vinyl amino acid (ester) copolymer and a preparation method of the polymer. Background technique: [0002] Various amino acids (esters), such as tyrosine, proline, lysine, cysteine, serine, threonine, etc., can be prepared from biomass. Polyamino acids can be synthesized from amino acids as monomers. Polyamino acid materials have good biocompatibility, and release small molecules during the degradation process as amino acids, which are non-toxic and easily absorbed and metabolized by the body. They are a type of biodegradable polymer materials. Surgical sutures, artificial skin, etc. have a wide range of applications. [0003] As far as we know, so far the preparation method of polyamino acid is obtained by the condensation reaction of groups (amino and carbo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F126/02C08F112/14C08F226/02C08F220/14C08F220/18C08F222/08C08F212/14C08F212/08C08F220/56C08F220/48C08F214/06C08F214/26C08F210/02C08F210/06C08F210/14C08F232/08
Inventor 黄启谷刘智张新莉黄海兵刘伟娇豆秀丽杨万泰
Owner BEIJING UNIV OF CHEM TECH