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2-Bromo-2,2-difluoroacetone acetone fork protection monoglyceride, water-based polyurethane and preparation method

A technology of acetonylidene acetate and difluoroacetate, applied in the field of printing and dyeing auxiliaries, can solve the problems of easy water absorption, poor flame retardancy, yellowing of textiles, etc.

Active Publication Date: 2022-04-22
HANGZHOU TRANSFAR FINE CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing water-based polyurethane generally has defects such as easy water absorption and moisture regain, poor flame retardancy, etc.
[0003] As Chinese patent CN101545207A discloses a kind of anti-pilling finishing agent for pure cotton knitted fabrics and its preparation method, add melamine, isophor heating, stirring in container, drop and dissolve isophor diisocyanate with isopropanol Mix the solution, then add catalyst, heat and mix evenly, after cooling, add isopropanol, end-capping agent, accelerator and water to fully react, then heat up to normal temperature, continue to stir to obtain water-based polyurethane, directly used as anti-pilling agent, which is not easy to use Textile yellowing, environmental friendliness and other advantages; but the prepared water-based polyurethane still has the problems of easy water absorption and poor flame retardancy

Method used

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  • 2-Bromo-2,2-difluoroacetone acetone fork protection monoglyceride, water-based polyurethane and preparation method
  • 2-Bromo-2,2-difluoroacetone acetone fork protection monoglyceride, water-based polyurethane and preparation method
  • 2-Bromo-2,2-difluoroacetone acetone fork protection monoglyceride, water-based polyurethane and preparation method

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preparation example Construction

[0029] The present invention provides a preparation method for 2-bromo-2,2-difluoroacetate protected acetonylidene monoglyceride described in the scheme, comprising the following steps: condensing 2-bromo-2,2-difluoroacetate, Glycerol and a basic catalyst are mixed for transesterification to obtain 2-bromo-2,2-difluoroacetate acetonylidene-protected monoglycerides having the structure described in formula I;

[0030] The molar ratio of the 2-bromo-2,2-difluoroacetate to acetonide is 1:1-5.

[0031] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known in the art.

[0032] In the present invention, the 2-bromo-2,2-difluoroacetate is preferably methyl 2-bromo-2,2-difluoroacetate or ethyl 2-bromo-2,2-difluoroacetate. The basic catalyst preferably includes one or more of hydroxide, carbonate, bicarbonate, sodium hydride and sodium alkoxide, more preferably includes alkali metal hydroxide, alkali metal carbonate...

Embodiment 1

[0070] Add 203 grams of ethyl 2-bromo-2,2-difluoroacetate, 260 grams of acetonide, and 3.2 grams of sodium methoxide to a 1L reaction vessel equipped with a thermometer, a reflux condenser, a water separator, and a stirrer at 115 After reacting at ℃ for 12 hours, the resulting reaction product was subjected to vacuum distillation to collect fractions under the condition of 104-106℃ / 25mmHg to obtain 2-bromo-2,2-difluoroacetate-protected acetonylidene monoglycerol with the structure shown in formula I The ester was 285.5 grams, the yield was 98.8%, and the purity was 99.5%.

[0071]

[0072] Carry out NMR analysis to the 2-bromo-2,2-difluoroacetate acetonylidene protected monoglycerides prepared in Example 1, the results are as follows Figure 1 ~ Figure 2 shown, where figure 1 is the H NMR spectrum, figure 2 It is NMR fluorine spectrum. Depend on Figure 1 ~ Figure 2 It can be seen that the acetonylidene-protected 2-bromo-2,2-difluoroacetate monoglyceride prepared in Ex...

Embodiment 2

[0077] Add 189 grams of 2-bromo-2,2-methyl difluoroacetate, 260 grams of acetonide, and 1.89 grams of potassium hydroxide in a 1L reaction vessel equipped with a thermometer, reflux condenser, water separator and stirrer. Reaction at 125°C for 8 hours, and then the obtained reaction product was subjected to vacuum distillation to collect fractions under the condition of 104-106°C / 25mmHg to obtain 283.3 grams of 2-bromo-2,2-difluoroacetonylidene-protected monoglyceride. The yield is 98.0%, and the purity is 99.5%.

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Abstract

The invention provides a 2-bromo-2,2-difluoroacetate protected monoglyceride, water-based polyurethane and their preparation methods, and relates to the technical field of printing and dyeing auxiliaries. The 2-bromo-2,2-difluoroacetate-protected monoglyceride can be used as a modified monomer to prepare water-based polyurethane, and the 2-bromo-2,2-difluoroacetate-protected glycerin The substituent at the C2 position of the monoester is two fluorine atoms and one bromine atom. When used in the preparation of waterborne polyurethane, fluorine and bromine groups are introduced into the structure of the waterborne polyurethane, and the obtained waterborne polyurethane has good moisture resistance and flame retardancy.

Description

technical field [0001] The invention relates to the technical field of printing and dyeing auxiliaries, in particular to a 2-bromo-2,2-difluoroacetonylidene-protected monoglyceride, water-based polyurethane and a preparation method. Background technique [0002] Printing and dyeing auxiliaries can endow fabrics with different styles and functions, and play an irreplaceable role in the textile field. Water-based polyurethane (PU) uses water as the medium, is safe and non-combustible, and has no pollution. It retains the excellent properties of traditional solvent-based polyurethanes, such as giving fabrics excellent softness, fullness, good elasticity, smoothness, and good hand feeling. Antistatic, etc., so it is an ideal printing and dyeing auxiliaries. However, the existing water-based polyurethane generally has defects such as easy water absorption and moisture regain, poor flame retardancy and the like. [0003] As Chinese patent CN101545207A discloses a kind of pure co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/24C08G18/32D06P1/52
CPCC07D317/24C08G18/3812D06P1/5285C07D317/22C08G2170/80C09J175/04C08G18/227C08G18/0823C08G18/4825C08G18/7621C08G18/8054C08G18/721C08G18/10C08G18/6692C08G18/3206B01J23/04B01J31/0201B01J31/04B01J31/121B01J2531/12B01J2531/13C08G18/222C08G18/3802
Inventor 王胜鹏陈八斤徐伟明宋金星章鹏飞王小君于本成黄又举杨小波
Owner HANGZHOU TRANSFAR FINE CHEM CO LTD