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Novel temperature-sensitive polymer and method for preparing novel temperature-sensitive polymer from L-lysine as renewable resource

A technology for temperature-sensitive polymers and renewable resources, which is applied in the field of polymers and can solve problems such as preparation and non-existence

Active Publication Date: 2014-08-27
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far there is no method for the preparation of thermosensitive polymer poly-N-vinyl-α-aminocaprolactam based on the renewable resource L-lysine

Method used

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  • Novel temperature-sensitive polymer and method for preparing novel temperature-sensitive polymer from L-lysine as renewable resource
  • Novel temperature-sensitive polymer and method for preparing novel temperature-sensitive polymer from L-lysine as renewable resource
  • Novel temperature-sensitive polymer and method for preparing novel temperature-sensitive polymer from L-lysine as renewable resource

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Preparation of L-lysine methyl ester dihydrochloride

[0058] Dry the 500ml single-necked flask, add 36.5gL-lysine monohydrochloride, add 500ml methanol, and add 45ml of benzoyl chloride dropwise under ice-water bath conditions. After the dropwise addition, continue the reaction at room temperature for 45 minutes, then placed in a 70°C oil bath and heated to reflux for 3 hours, then cooled at room temperature overnight, crystals precipitated, filtered, washed with ether, and dried in vacuum at 20°C for 12 hours to obtain L-lysine methyl ester dihydrochloride 29.2g, yield 80%.

[0059] Preparation of (S)-α-aminocaprolactam

[0060] Dry the 500ml three-necked flask, weigh 23.3g L-lysine methyl ester dihydrochloride, dissolve it in 320ml methanol, add dropwise 80mL methanol solution containing 10g sodium hydroxide at room temperature, react at room temperature for 24h, filter, spin The filtrate was dried and recrystallized to obtain 18.6 g of (S)-α-aminocaprolactam as a ...

Embodiment 2

[0071] Preparation of L-lysine methyl ester dihydrochloride

[0072] Dry the 500ml single-necked flask, add 36.5gL-lysine monohydrochloride, add 500ml of methanol, and add 43ml of thionyl chloride dropwise under ice-water bath conditions. After the dropwise addition, continue the reaction at room temperature for 30 Minutes, then placed in a 70°C oil bath and heated to reflux for 24 hours, then cooled at room temperature overnight, crystals precipitated, filtered, washed with ether, and vacuum-dried at 20°C for 12 hours to obtain L-lysine methyl ester dihydrochloride 33.6 g, yield 92%.

[0073] Preparation of (S)-α-aminocaprolactam

[0074] Dry the 500ml three-necked flask, weigh 23.3g L-lysine methyl ester dihydrochloride, dissolve it in 320ml methanol, add dropwise 80mL methanol solution containing 10g sodium hydroxide at room temperature, react at room temperature for 24h, filter, spin The filtrate was dried and recrystallized to obtain 18.2 g of (S)-α-aminocaprolactam as a ...

Embodiment 3

[0085] Preparation of L-lysine methyl ester dihydrochloride

[0086] Dry the 500ml single-necked flask, add 36.5gL-lysine monohydrochloride, add 500ml methanol, and add 42.8ml sulfonyl chloride dropwise under ice-water bath conditions. After the dropwise addition is completed, continue the reaction at room temperature for 30 minutes. Then placed in an oil bath at 100°C and heated to reflux for 3 hours, the system became clear and transparent, then cooled at room temperature overnight, crystals precipitated, filtered, washed with ether, and dried in vacuum at 20°C for 12 hours to obtain L-lysine methyl Ester dihydrochloride 31.8g, yield 87%.

[0087] Preparation of (S)-α-aminocaprolactam

[0088] Dry the 500ml three-neck flask, weigh 23.3g of L-lysine methyl ester dihydrochloride, dissolve it in 320ml of methanol, add 19mL of dry pyridine dropwise at room temperature, react at room temperature for 6h, filter, spin the filtrate, and recrystallize After that, 14 g of (S)-α-amin...

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Abstract

The invention provides a novel temperature-sensitive polymer and a method for preparing the novel temperature-sensitive polymer from L-lysine as a renewable resource, and belongs to the technical field of polymers. The novel temperature-sensitive polymer has a structure shown in the formula (VII). The novel temperature-sensitive polymer is prepared from a renewable resource L-lysine as an initial raw material. The novel temperature-sensitive polymer has an amide structure similar to the structure of poly(N-isopropylacrylamide). Through an ultraviolet spectrophotometer, polymer aqueous solution light transmittance variation with a temperature is determined so that it is showed that the polymer has good temperature sensibility. The invention also provides the method for preparing the novel temperature-sensitive polymer from L-lysine as a renewable resource. The method has simple processes and utilizes the cheap raw materials.

Description

technical field [0001] The invention relates to the technical field of polymers, in particular to a novel thermosensitive polymer and a method for preparing the novel thermosensitive polymer with renewable resource L-lysine. Background technique [0002] Thermosensitive polymers are smart materials that respond to temperature. A notable feature of thermosensitive polymers is that they have a low critical solution temperature (LCST) in aqueous solution. The so-called LCST refers to the lowest cloud point temperature. As the temperature changes, the dissolution state of the temperature-sensitive polymer will change near the critical point. The temperature is lower than the LCST, the polymer has good solubility in water, and the solution is transparent; when the temperature is higher than the LCST, the polymer will separate out of the water. As a classic temperature-sensitive polymer, although poly-N-isopropylacrylamide has been fully studied and has been widely used in bioma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F126/06C08F8/00
Inventor 陶友华陈霄宇王献红赖海旺
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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