CS227598B1 - Organo-silicon esters and method of preparing same - Google Patents

Description

The invention relates to organosilicon esters and a process for their preparation from phenyltrichlorosilane, glycols, polyglycols, aliphatic dicarboxylic acids and monovalent alcohols.

Typically, organosilicon esters are prepared using solvents and hydrogen chloride acceptors. The use of solvents entails costly removal and the bases used as hydrogen chloride acceptors produce bulky amounts of hydrochloride, again leading to the necessity of using solvents because of the stirrability of the reaction mixture. New types of esters have now been found and a new process eliminating these disadvantageous synthesis conditions has been developed.

The esters obtained have relatively high viscosities at higher temperatures, excellent viscosity dependence and low pour point. They can be used for the preparation of oils, greases and plasticizers.

Organosilicate esters of the formula I ^R10

c.h,

I ^{6 5}

Si I

STEED_

-0A-CO (CH2 ₎ to 10

-WHAT

C, H, ₍ 6.55

-0A- Si -OR / 1 /

OR 1 to 3 wherein A and / -CH ₂ -CH ₂ -O) to 5 or

-CH-CH-O

I ²

CH _n to 5 and R (to R ₄ denote an alkyl group having 8 to 14 carbon atoms) formed by the reaction of dicarboxylic aliphatic acids with ethylene glycol, polyethylene glycols, propylene glycol, polypropylene glycols, and phenyl227598 trichlorosilane and monovalent alcohols according to the invention said dicarboxylic acids with said glycols, the resulting reaction mixture is reacted with phenyltrichlorosilane and said alcohols while the temperature is raised from room temperature to 160 ° C, then nitrogen is added to the reaction mixture at 90 to 120 ° C to reduce the hydrogen chloride content, then the reaction mixture is treated with a saturated solution of sodium hydroxide in the above alcohol and the volatiles are distilled off.

The examples below illustrate embodiments of the invention.

Example 1

In a 1 L flask equipped with a vacuum distillation water separator, 202 g of sebacic acid, 300 g of triethylene glycol, 50 ml of toluene were introduced and esterified to a temperature of up to 160 ° C in a known manner to obtain 36 ml of reaction water. The obtained diester was placed in a 2.51 Keller four-necked flask at 70-110 ° C equipped with a stirrer, thermometer, reflux condenser, admission funnel, heating bath, and manometer drain. 260 g of 2-ethylhexanol were added to the diester, and then 422 g of phenyltrichlorosilane and finally 380 g of 2-ethylhexanole were added over 1 hour while stirring and heating the flask. The charge was controlled according to the pressure of the escaping hydrochloric acid and the temperature was raised to rise to 110-120 ° C in the flask. Nitrogen was then introduced into the bottom of the flask and the acid content of the flask was reduced to a acid value of 0.12 mg KOH / g with stirring under nitrogen for 30 to 60 min. A calculated amount of a saturated solution of sodium hydroxide in 2-ethylhexanol was then added to the flask with stirring. The contents of the flask were then transferred to a distillation vacuum apparatus and the volatiles were distilled off at 2000 Pa to a boiling point of 205 ° C. After cooling, the distillation residue was filtered through paper to obtain 953 g of a clear, yellow-brown ester with an acid number of 0.08 mg KOH / g, n _D ²⁵ = 1.4791, a flash point of 228 ° C, a burning temperature of 260 ° C, a freezing point. -44 ° C

Claims (2)

SUBJECT 1. Organosilicate esters of the general formula a viscosity at ²⁰⁰ ° C . _r , 8.24 mm ² . s ^-1 150 [deg.] C 14.09 mm ² . s “ ¹ Mp 100 ° C 33.46 mm ² . s ^_1 Deň: 32 ° C 137 mm ² . s' ¹ -15 ° C 13,720 mm ² . s ^_1 , viscosity index 214, moisture content at 80% relative humidity at 20 ° C for 90 h, 0.37 wt. Example 2 The procedure and apparatus of Example 1 were worked up 384 g of tripropylene glycol 146 g of adipic acid. 422 g phenyltrichlorosilane> ‘580 g 2-ethylhexanol. After distillation at a pressure of 2700 Pa to a boiling point of 179 ° C, 960 g of a clear yellow-brown ester with an acid number of 0.10 mg KOH / g, n _D ²⁵ = 1.4802, a flash point of 198 ° C, a combustion temperature of 247 ° C were obtained. , pour point -26 ° C, viscosity at 200 ° C 12.98 mm ² , s ^-1 150 ° C 26.17 mm ² , s ¹ 100 ° C 83.54 mm ² , s ^-1 50 ° C 530 ^mm2. s' ^1, a viscosity index of 175, moisture absorption at 80% relative humidity at 20 ° C for 90 h 0.33% by weight. Example 3 In an analogous manner to Example 1, the ester was synthesized 230 g dodecanedioic acid 300 g triethylene glycol 422 g of phenyltrichlorosilane 595 g of 2-ethylhexanol. After distillation at a pressure of 2600 Pa to a boiling point of 225 ° C, 1,076 g of a clear light brown ester with an acid number of 0.08, n _D ²⁵ = 1.4757, a flash point of 229 ° C, a combustion temperature of 256 ° C, a freezing point were obtained. -40 ° C, viscosity at 200 ° C 4,45 mm ² , s “ ¹ 150 ° C 7.84 mm ² , s “ ¹ 100 ° C 15.92 mm ² , s “ ¹ 50 ° C 63.58 mm ² , s ¹ -20 ° C 6720 mm ² s ^-1 viscosity index 186. OF THE INVENTION ^R 1 ° C, H, I ^{5 6} Si I 0R " -OA-CO (CH) -CO ^Z 4 to 10 where A = (-CH ₂ -CH ₂ -O) 1 to 5 C ₆ ^H 5 -0A- Si -0R. 1 to 3 or. OR-CH-CH-O I ² L_ ^CH3 1 to 5 (1) and R 1 to R ₄ denote an alkyl group having 8 to 14 carbon atoms. 2. A process for the preparation of esters of the formula I according to claim 1 by reacting dicarboxylic aliphatic acids with ethylene glycol, polyethylene glycols, propylene glycol, polypropylene glycols and further with phenyltrichlorosilane and monovalent alcohols, characterized in that after reaction of said dicarboxylic acids with said glycols with phenyltrichlorosilane and the alcohols, raising the temperature from room temperature to 160 ° C, then nitrogen is added to the reaction mixture at 90 to 120 ° C to reduce the hydrogen chloride content, and the reaction mixture is treated with a saturated sodium hydroxide solution as described above. alcohol, and the volatiles are distilled off.