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Urea-containing mercaptosilanes, process for preparation thereof and use thereof

A mercaptosilane, hydrocarbon-based technology, applied in chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, organic chemistry, etc., can solve problems such as poor processing characteristics, low network density, and poor wet-slip properties.

Active Publication Date: 2016-08-24
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Known disadvantages of uretaminomercaptosilanes are poor processing characteristics, low network density, poor wet skid properties and low dynamic stiffness

Method used

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  • Urea-containing mercaptosilanes, process for preparation thereof and use thereof
  • Urea-containing mercaptosilanes, process for preparation thereof and use thereof
  • Urea-containing mercaptosilanes, process for preparation thereof and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] Embodiment 1: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -Cl and KSAc preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S-CO-CH 3

[0166] At the beginning will (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -Cl (81.52 g, 0.25 mol, 1.00 equiv) was charged into ethanol (85 ml) in a 500 ml three-necked flask with a stirrer, reflux condenser and internal thermometer. Potassium thioacetate (28.48 g, 0.25 mol, 1.00 equiv) was added and the mixture was heated to reflux. After 3.5 hours reaction time, the mixture was cooled to room temperature and the suspension was filtered. The filtrate was freed of solvent on a rotary evaporator and dried under reduced pressure. (EtO) was obtained as a light brown solid 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S-CH 3Product (81.64 g, 89% of theory).

[0167] 1 H NMR (δ ppm ,500MHz,CDCl 3 ):0.64(2H,t),1.24(9H,t),1.61(2H,m),2.35(3H,s),3.01(2H,t),3.16(2H,t),3.34(2H,t) ,3.82(6H,q),4.5-7.0(2H,br);

...

Embodiment 2

[0169] Embodiment 2: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NH 2 、OCN-CH 2 CH 2 -Cl and KSAc preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S-CO-CH 3

[0170] 3-Aminopropyltriethoxysilane (132.82 g, 0.60 mol, 1.00 equiv) was initially charged to ethanol (300 ml) in a three-necked flask equipped with a precision glass stirrer, internal thermometer, dropwise Funnel and reflux condenser, and cooled to -78°C. 2-Chloroethyl isocyanate (63.34 g, 0.60 mol, 1.00 equiv) was added dropwise at -78°C to -68°C over 1.75 hours, then the mixture was heated to 50°C. Potassium thioacetate (68.53 g, 0.60 mol, 1.00 equiv) was added in five portions, and the mixture was heated to reflux. After 2.25 hours reaction time, the mixture was cooled to room temperature and the suspension was filtered. The filtrate was freed of solvent on a rotary evaporator and dried under reduced pressure. (EtO) was obtained as a waxy white solid 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S-CH 3...

Embodiment 3

[0173] Embodiment 3: by (EtO) 3 Si-CH 2 CH 2 CH 2 -NCO, HCl·H 2 N-CH 2 CH 2 -Cl and KSAc preparation (EtO) 3 Si-CH 2 CH 2 CH 2 -NH-CO-NH-CH 2 CH 2 -S-CH 3

[0174] 2-Chloroethylamine hydrochloride (73.86 g, 0.70 mol, 1.00 eq) was initially charged to ethanol (2.0 l) in a 4 l three-necked flask with precision glass stirrer, internal thermometer, drop Add a funnel and reflux condenser, and cool to -78°C, then add sodium ethoxide (226.83 g, 0.70 mol, 1.00 equiv, 21% in ethanol). 3-Isocyanatopropyl(triethoxysilane) (173.15 g, 0.70 mol, 1.00 equiv) was then added dropwise at -78°C to -65°C over 3 hours, and the mixture was then heated to 50°C . Potassium thioacetate (79.95 g, 0.70 mol, 1.00 equiv) was added in five portions and the mixture was heated to reflux. After 4 hours reaction time, the mixture was cooled to room temperature and the suspension was filtered. The filtrate was freed of solvent on a rotary evaporator and dried under reduced pressure. Obtained a...

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Abstract

The invention relates to urea-containing mercaptosilanes of the formula I which are prepared by reacting a halosilane of the formula II with compounds of the formula III in an alcohol.

Description

technical field [0001] The present invention relates to urea-mercapto-containing silane, its preparation method and its use. Background technique [0002] CAS 1082204-82-7, 1268617-33-9 and 104261-54-3 disclose compounds of the formula: [0003] [0004] Additionally, JP 2008279736 A discloses urea-containing silanes for coatings. [0005] DE 3424534 A1 discloses N,N'- and N,N',N'-substituted urea-containing silanes of the formula: [0006] [0007] The preparation is carried out by reacting amino compounds, halosilanes and alkali metal cyanates in an aprotic polar organic solvent such as DMF or DMSO. [0008] Additionally, JP 2002311574 discloses powder coatings comprising silanes of the formula: [0009] R 1 -S-R 2 -NH-C(O)-NH-R 3 -Si(R 4 ) m (OR 5 ) 3-m . [0010] WO 9955754 A1 discloses a photosensitive resin composition comprising an alkoxysilane of the formula: [0011] [(R 1 O) 3-a (R 2 ) a Si-R 3 -A-C(O)-B] m -X. [0012] Disadvantages of kno...

Claims

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Application Information

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IPC IPC(8): C07F7/18C08L9/06C08L7/00C08L9/00C08K13/02C08K5/548C08K3/36C08K3/22C08K5/09
CPCC07C275/00C07F7/10C07F7/1804C07F7/1872
Inventor C·勒本R·莫泽S·迈尔
Owner EVONIK OPERATIONS GMBH
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