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A kind of unsaturated polyol and photocurable polyurethane prepared therefrom and their manufacture method

A polyol, unsaturated technology, applied in the field of photocuring, can solve the problems of photoinitiation efficiency, limited degree of crosslinking and curing, and few double bond molecules, so as to achieve the effect of enhancing initiation efficiency, enhancing energy transfer, and increasing curing rate

Active Publication Date: 2021-06-29
JIANGSU BIOSURF BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although Patent Document 4 introduces benzophenone into the side chain of polyurethane and uses hydroxy acrylate to end-block to prepare spontaneously curable polyurethane, the photoinitiated polyurethane structure has fewer molecules with double bonds per unit mass. Efficiency and degree of cross-linking and curing are still limited

Method used

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  • A kind of unsaturated polyol and photocurable polyurethane prepared therefrom and their manufacture method
  • A kind of unsaturated polyol and photocurable polyurethane prepared therefrom and their manufacture method
  • A kind of unsaturated polyol and photocurable polyurethane prepared therefrom and their manufacture method

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preparation example Construction

[0063] Further, the present invention provides a method for preparing the above-mentioned unsaturated polyol, which includes the following steps: 1) mixing hydroxyalkyl (meth)acrylate or hydroxyalkyl (meth)acrylamide and halogen Acetyl halide reaction synthesis to obtain an intermediate product containing halogen and unsaturated bonds; 2) reacting the intermediate product with an amino compound to obtain the unsaturated polyol.

[0064] Preferably, step 1) dissolve the hydroxyalkyl (meth)acrylate or hydroxyalkyl (meth)acrylamide in a solvent, add haloacetyl halide dropwise at low temperature, and react under the action of a catalyst to obtain an intermediate product. The hydroxyalkyl (meth)acrylate is selected from one or more of hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate; the hydroxyalkyl (meth)acrylamide is selected from One or more of N-methylolacrylamide, N-hydroxyethylacrylamide, N-hydroxypropylacrylamide; the haloacetyl halide is selected from any one o...

Embodiment

[0099] The following examples are given to illustrate the present invention, and those skilled in the art can understand that the examples are only exemplary descriptions, not exhaustive descriptions. The preparation examples are compound synthesis examples, and the chemical raw materials and reagents involved are all commercially available or synthesized according to published documents.

[0100] The double bond content and photosensitive group content are determined by 1 H NMR spectroscopy.

[0101] The degree of cross-linking (%) of the coating is measured by Soxhlet extraction method: take a certain mass of cured coating sample, cut it and extract it with a Soxhlet extractor at 120 ° C for 12 hours, vacuum dry and weigh after extraction, And calculate the coating crosslinking degree.

[0102] According to GB / T8808-1988, the peel strength (N / mm) of the polyurethane coating was tested.

preparation example 1

[0103] Preparation Example 1: Synthesis of Unsaturated Polyols

[0104] Hydroxyethyl acrylate (11.5 mL, 0.1 mol) was dissolved in dichloromethane, and bromoacetyl bromide (9.6 mL, 0.11 mol) was added dropwise to the solution at low temperature. The molar ratio of bromoacetyl bromide to hydroxy ethyl acrylate was 1.1:1, reacted under the action of sodium hydroxide (4g, 0.1mol) for 0.5h, raised the temperature to 30°C, and continued to react for 16h. After purification and drying, 2-(2-bromoacetoxy)ethyl acrylate ( 16.5 g, the yield was 70%); after that, 2-(2-bromoacetoxy) ethyl acrylate (11.8 g, 0.05 mol) and diethanolamine (6.3 g, 0.06 mol) were dissolved in dioxane , under the catalysis of triethylamine (6.1g, 0.06mol), reacted at 60°C for 5h, separated and purified, and dried to obtain 2-(N,N-dihydroxyethyl)-2-acetoxyethyl acrylate (10.2 g, 78% yield). For the NMR spectrum of the product, see figure 1 , 1 H NMR(δ / ppm):2.51(m,4H,CH 2 ),3.35(s,2H,CH 2 ),3.52(m,4H,CH 2 ...

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Abstract

The present invention relates to an unsaturated polyol, photocurable polyurethane prepared therefrom and their production method. The unsaturated polyol contains units of unsaturated double bonds and co-initiator tertiary amines, and the photocurable polyurethane is prepared from the polyols, the main chain contains tertiary amine groups, and the side chain has unsaturated double bond groups And photosensitive group unit, unsaturated double bond group: the content ratio of photosensitive group is (4-10): (8-25), described polyurethane can spontaneously polymerize under ultraviolet light irradiation, need not add photoinitiator And cross-linked solidification. The structure design of the polyurethane of the present invention is relatively flexible, and there are multiple crosslinking sites in the molecule. By adjusting the proportion of unsaturated polyols in the polymerized monomers and the unsaturated double bond groups of polyols containing photosensitive groups, it is possible to obtain Polyurethane coating with high efficiency and cross-linking cure and high peel strength.

Description

technical field [0001] The invention belongs to the technical field of photocuring, and more specifically, the invention relates to unsaturated polyols and photocurable polyurethanes prepared therefrom. Background technique [0002] Ultraviolet light curing technology is a process technology that takes into account both environmental and economic benefits. Compared with traditional curing technology, it has the characteristics of short curing time, simple equipment, excellent coating performance, and environmental friendliness. It is widely used in aerospace, electronics, etc. , medical and health and other fields have been widely used. Among them, as a typical representative of the application of this technology, UV-curable coatings such as photo-curable polyurethane have the characteristics of low energy consumption, fast curing speed, and excellent coating performance, so they have achieved rapid development. [0003] The formulation of UV-curable coatings is usually com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/32C08G18/10C08G18/12C08G18/66C08G18/48C09D175/14
CPCC08G18/10C08G18/12C08G18/4825C08G18/6674C09D175/14C08G18/3221C08G18/3819C08G18/3206
Inventor 徐亚骏
Owner JIANGSU BIOSURF BIOTECH CO LTD
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