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Coordination type boric acid ester coupler containing sulfur element and its preparing process

A technology of borate coupling agent and trialkyl borate, which is applied in the field of coordination type borate coupling agent and its preparation, can solve the problems of poor hydrolysis stability, achieve strong coupling effect, and simple production process , the effect of high hydrolytic stability

Inactive Publication Date: 2007-08-01
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with silane coupling agents, borate coupling agents have the advantages of simple preparation process, low cost, safety and non-toxicity, high thermal stability, etc., but their hydrolytic stability is poor, even a very small amount of moisture in the air can make boron Ester Hydrolysis Deterioration

Method used

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  • Coordination type boric acid ester coupler containing sulfur element and its preparing process
  • Coordination type boric acid ester coupler containing sulfur element and its preparing process
  • Coordination type boric acid ester coupler containing sulfur element and its preparing process

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preparation example Construction

[0021] The preparation of the coordination type borate coupling agent containing sulfur element is carried out in two steps. The first step is to react an equimolar trialkyl borate with mercaptoethanol to generate a borate compound containing a sulfur-boron coordination bond Removal of the alcohol by-product R during the reaction 1 OH, making the transesterification continue is one of the keys of the present invention. The reaction temperature should be slightly higher than the alcohol by-product R 1 The boiling point of OH is lower than that of the inert solvent xylene.

[0022] The sulfur-boron coordination bond is unstable. The second step of the present invention is to react the borate compound containing sulfur-boron coordination bond with fatty acid chloride to generate the borate coupling of sulfur-containing element with thioester bond and (carbonyl) oxygen-boron coordination agent, the reaction principle is

[0023]

[0024] It is one of the keys of the prese...

Embodiment 1

[0027] Using triethyl borate and acetyl chloride as raw materials to prepare the coordination type borate coupling agent containing sulfur elements:

[0028] 1) Weigh 0.1mol (14.58g) of triethyl borate, place it in a round-bottomed three-necked flask, add 277g of xylene, make a solution with a mass concentration of 5%, add 0.1mol (7.80g) of mercaptoethanol, stir, Heating to 80°C, reacting for 7 hours, during which the ethanol by-product was continuously distilled;

[0029] 2) Weigh 0.1mol (8.50g) of pyridine, add it into the solution obtained in step 1), cool to 0°C, stir vigorously and exhaust with nitrogen, add 0.1mol (7.85g) of acetyl chloride dropwise at a speed of 1ml / min, After the dropwise addition, continue to react for 1 h under stirring and exhaust conditions, filter to remove solid salt by-products, and distill under reduced pressure to remove low-boiling fractions to obtain a coordination borate coupling agent containing sulfur elements.

Embodiment 2

[0031] Using tri-n-propyl borate and propionyl chloride as raw materials to prepare the coordination type borate coupling agent containing sulfur elements:

[0032] 1) Weigh 0.1mol (18.78g) of tri-n-propyl borate, place it in a round-bottomed three-neck flask, add 75g of xylene to make a solution with a mass concentration of 20%, add 0.1mol (7.80g) of mercaptoethanol, and stir , heated to 100°C, and reacted for 3 hours, during which the by-product of propanol was continuously distilled;

[0033] 2) Weigh 0.15mol (12.75g) of pyridine, add it to the solution obtained in step 1), cool to 0°C, stir vigorously and exhaust with nitrogen, add 0.1mol (9.25g) propionyl chloride dropwise at a speed of 2ml / min, After the dropwise addition, continue to react for 3 hours under stirring and exhaust conditions, filter to remove solid salt by-products, and distill under reduced pressure to remove low-boiling fractions to obtain a coordination borate coupling agent containing sulfur elements. ...

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Abstract

The invention discloses a boric acid ester coupling agent of corrdination type containing sulfur and the method for preparing the same. The method comprises: putting boric acid trialkyl ester into dimethylbenzene to make solution of 5- 20% (mass concentration); adding dimethylbenzene with its molar weight the same to that of boric acid trialkyl ester; heating, reacting for 3-7 hours under stirring, distilling out alcohol side product; cooling; adding pyridine with its molar weight being 1- 1.5 times of that of boric acid trialkyl ester, stirring and ventlating nitrogen gas; dropping carboxylic acid chlorides with its molar weight being the same to that of boric acid trialkyl ester , stirring and discharging gas and reacting for 1- 3 hours; filtering to remove solid salt side product; vacuum distillating to remove light ends, and getting boric acid ester coupling agent of corrdination type containing sulfur. The invention is characterized by easy process, high productivity, and high thermal- stability and strong coupling effect of produced product. The product can replace the traditional coupling agent and be used in rubber containing white carbon black and calcium carbonate.

Description

technical field [0001] The invention relates to a coordination type borate coupling agent containing sulfur element and a preparation method thereof. Background technique [0002] Compared with carbon black, silica has obvious advantages in terms of tread rubber wear resistance, wet road traction and rolling resistance, and is used as the main reinforcement of the new generation of low rolling resistance and low fuel consumption "green tires" agent. [0003] The surface of silica particles contains a large number of silanol groups, which are easy to agglomerate during the rubber mixing process, so the reinforcement effect of silica without surface treatment is poor. In tire tread rubber, silica, especially highly dispersed precipitated silica, and sulfur-containing bifunctional silane coupling agents such as γ-mercaptopropyltrimethoxysilane, γ-thiocyanopropyltriethyl Combined use of oxysilane, bis(3-triethoxysilylpropyl) disulfide (TESPD) or bis(3-triethoxysilylpropyl) tet...

Claims

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Application Information

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IPC IPC(8): C07F5/04C08K5/55
Inventor 宋义虎郑强
Owner ZHEJIANG UNIV
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