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Silicon containing macromolecule photo-initiation agent, synthesis and uses thereof

A technology of photoinitiators and macromolecules, applied in chemical instruments and methods, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., can solve problems such as increased hazards and enhanced concentration of photolyzed products of photoinitiators , to achieve a good eliciting effect

Inactive Publication Date: 2008-07-16
上海长悦涂料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effects described by this patented inventor are that it introduces specific chemical structures onto certain types of material called siloxanes which enhance their ability to initiate curative reactions when exposed to light for creation of coatings, photosensitive printing plates, molded articles, prosthetic teeth, medical implants, and other applications such as 3D models. This results from adding more polar group(s) on these compounds than usual ones, resulting in better primers without requiring high concentrations (molar).

Problems solved by technology

Technological Problem: Current methods involve photosensitizing agents like benzene sulfonate esters, α - amino acids, dyes, quaternary salts, metal complexes, chelated therapeutic drugs, polyvinyl alcohol, polyglycerols, carboxylic acid derivatives, hydroxyacrylate groups, vinyl lactams, cyclohexane dimmers, epoxydimethanones, nitrogen bases, oxazolidone groupings, siloxanes, alkynaphthalenetides, alkaline earth metals, ion exchange resins, solvent systems containing volatile liquids, and other chemical compositions useful in various applications including coatings.

Method used

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  • Silicon containing macromolecule photo-initiation agent, synthesis and uses thereof
  • Silicon containing macromolecule photo-initiation agent, synthesis and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 1173-IPDI-Tego 2311 macromolecular photoinitiator

[0031] Add 17.76g (0.08mol) of IPDI (isophorone diisocyanate) and 400ml of ethyl acetate into a three-necked flask, start stirring and heating, when the temperature rises to 60°C, add 0.06g of catalyst dibutyltin dilaurate , and start to drop 13.36g (0.08mol) 1173 (hydroxyl dimethyl acetophenone), three hours later, take a sample, measure the isocyanic acid value, after reaching half of the initial value, stop the reaction, the ethyl acetate is rotated After removal from the evaporator, 1173-IPDI was obtained.

[0032] Add 50g (0.04mol) of Tego 2311 (DEGUSSA company) into a 1000ml three-neck flask, start magnetic stirring, and start heating. When the temperature rises to 75°C, start to drop 1173-IPDI15.56g ( 0.04mol), after six hours of reaction, the target product was obtained after the isocyanate group was determined to be completely reacted by infrared spectroscopy.

[0033] The product is identified ...

Embodiment 2

[0035] Synthesis of 184-TDI-Tego 2311 macromolecular photoinitiator

[0036] Add 13.92g (0.08mol) of TDI (toluene diisocyanate) and 350ml of toluene into a three-necked flask, start stirring and start heating, when the temperature rises to 60°C, add 0.06g of catalyst dibutyltin dilaurate, and start to drop 16.32g (0.08mol) 184 (1-benzoylcyclohexyl-1-alcohol), after three hours, take a sample, measure the isocyanic acid value, after reaching half of the initial value, after the solvent is removed by a rotary evaporator, obtain 184-TDI.

[0037] Add 50g (0.04mol) of Tego 2311 into a 1000ml three-necked flask, start magnetic stirring, and start heating. When the temperature rises to 75°C, start to add dropwise the

[0038] 184-TDI 15.12g (0.04mol), after six hours of reaction, the target product was obtained after the complete reaction of the isocyanate group was confirmed by infrared spectroscopy.

[0039] The product is identified by infrared spectrum and ultraviolet spectrum...

Embodiment 3

[0041] Synthesis of Benzophenone-HDI-550 Macromolecular Photoinitiator

[0042] Add 13.44g (0.08mol) of HDI (hexamethylene diisocyanate) and 400ml of tetrahydrofuran into a three-necked flask, start stirring and start heating, when the temperature rises to 60°C, add 0.06g of catalyst dibutyltin dilaurate, and Start to add 15.84g (0.08mol) of hydroxybenzophenone dropwise. After three hours, take a sample and measure the isocyanate value. After reaching half of the initial value, stop the reaction, and remove the solvent by a rotary evaporator to obtain 184-HDI.

[0043]Add 50g (0.04mol) of polydimethylsilane 550 (ACROS company) into a 1000ml three-necked flask, start magnetic stirring, and start heating. When the temperature rises to 60°C, start to drop the diphenyl Ketone-HDI 14.64g (0.04mol). After six hours of reaction, the target product was obtained after the isocyanate group was determined to be completely reacted by infrared spectroscopy.

[0044] The product is identif...

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Abstract

The invention relates to a Si-containing macromolecular photoinitiator and the synthesizing method and the uses belong to the photographic polymer material field. In a general formula of the photoinitiator being (I), I is the photoinitiator with hydroxyl, i.e. the hydroxyl-containing benzoin class, benzoin ethers, alkyl-acetophenones, alkyla-acetophenones, benzophenone type, thioxcanthone derivatives, coumarone class and camphorquinone compound; R1 is the alkyl of C1-C12, or the alkyl or aryl of C1-C12 substituted by N, O, S heteroatoms; R2 and R3 are alkyls of C1-C12, the alkyls of C1-C12 substituted by N, O, S heteroatoms, or alkoxyls of C1-C12; n is equal to 3 to 50. The synthesizing method obtains the compounds of isocyanate with photoinitiator by the reaction of the hydroxyl-containing micro-molecular photoinitiator with an isocyanate group of the diisocyanate, and allows the reaction of the photoinitiator-containing compounds of isocyanate with the hydroxyl-containing siloxane macromolecular compounds. The synthesizing method is used for initiating the free radical photopolymerization, improving the speed and efficiency of producing active species by photo sensitive decomposition and reducing the micro-molecular residue and biological toxicity of coatings.

Description

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Claims

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Application Information

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Owner 上海长悦涂料有限公司
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