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KR-102964189-B1 - Method for manufacturing an organopolysiloxane having unsaturated groups

KR102964189B1KR 102964189 B1KR102964189 B1KR 102964189B1KR-102964189-B1

Abstract

The present invention relates to a method for producing an organopolysiloxane having unsaturated groups. In the first step, an organopolysiloxane (A) comprising a unit of the following chemical formula (I): provided that a+b≤3, and siloxane (A) is an organopolysiloxane (A) having at least one radical Q, Organopolysiloxane (B) containing units of the following chemical formula (II): (B), an organopolysiloxane where d+f≤3 An organopolysiloxane compound (C) optionally comprising at least one structural unit of the following chemical formula (III) per molecule: However, an organopolysiloxane compound (C) in which e+g≤2, Here, the radicals and indices of the chemical formula have the meanings specified in claim 1, and Basic catalyst (D) selected from the group of alkali metal hydroxides, alkali alcoholates and alkali metal siloxanolates Mix together. In the second step, the mixture obtained in the first step is reacted at a temperature of 80°C to 170°C, and In the third step, the reaction mixture obtained in the second step is neutralized using a carboxylic acid derivative (E) having at least four carbon atoms.

Inventors

  • 머젯 마르커스
  • 빈들 요한

Assignees

  • 와커 헤미 아게

Dates

Publication Date
20260512
Application Date
20210324

Claims (10)

  1. A method for manufacturing an organopolysiloxane having unsaturated groups, In the first stage Organopolysiloxane (A) containing units of the following chemical formula (I): Here, R may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and Q is an unsaturated hydrocarbon radical that may be the same or different and may include aromatic and/or aliphatic double bonds, and a is 0, 1, 2, or 3, and b is 0, 1, 2, or 3, and provided that a+b≤3, and siloxane (A) is an organopolysiloxane (A) having at least one radical Q, Organopolysiloxane (B) containing units of the following chemical formula (II): Here, R₂ may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and R1 is an alkyl radical having 1 to 4 carbon atoms that may be the same or different and may be substituted by a hydrogen atom or an oxygen atom, and d is 0, 1, 2, or 3, and f is 0, 1, 2, or 3, and (B), an organopolysiloxane where d+f≤3 Organopolysiloxane compound (C) comprising at least one structural unit of the following chemical formula (III) per molecule: Here, R3 may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and Q1 is an unsaturated hydrocarbon radical that may be the same or different and may include aromatic and/or aliphatic double bonds, and Y is a divalent to divalent organic radical having 1 to 30 carbon atoms and may include one or more oxygen atoms, and e is 0 or 1, and c is an integer from 1 to 11, and g is 0 or 1, and However, an organopolysiloxane compound (C) in which e+g≤2, and Basic catalyst (D) selected from the group of alkali metal hydroxides, alkali alcoholates and alkali metal siloxanolates The step of mixing them together, In the second stage A step of reacting the mixture obtained in the first step at a temperature of 80°C to 170°C and In the third stage A step of neutralizing the reaction mixture obtained in the second step using a carboxylic acid derivative (E) having at least four carbon atoms. A method including
  2. In paragraph 1, A method in which the above-mentioned organopolysiloxane (A) is used in an amount of 1.0 to 40 weight% based on the total weight of the organopolysiloxane compounds (A), (B), and (C).
  3. In paragraph 1, A method in which the above-mentioned organopolysiloxane (B) is used in an amount of 30 to 99 weight percent based on the total weight of the organopolysiloxane compounds (A), (B) and (C).
  4. In paragraph 1, Alkali metal hydroxide is used as a catalyst (D) in the method.
  5. In paragraph 1, The carboxylic acid derivative (E) used has at least 8 carbon atoms, method.
  6. In paragraph 1, The second step is performed at a pressure of 20 to 1100 hPa, a method.
  7. In paragraph 1, In the first stage Organopolysiloxane (A), organopolysiloxane (B), and organopolysiloxane compound (C) are initially filled at room temperature, catalyst (D) is metered at a temperature of 20°C to 90°C, and these are mixed together. In the second stage The mixture obtained in the first step is reacted at a temperature of 90°C to 150°C and a pressure of 20 to 1100 hPa, and In the third stage A method of neutralizing the reaction mixture obtained in the second step with component (E) at a temperature of 100°C to 160°C.
  8. In paragraph 1, A method in which, after the completion of the third step, the reaction mixture is post-treated by distillation, said distillation is performed at a temperature of 140°C to 170°C and a pressure of 1 to 50 hPa.
  9. In any one of paragraphs 1 through 8, A method in which the obtained product has a turbidity of 0 to 65 FTU.
  10. delete

Description

Method for manufacturing an organopolysiloxane having unsaturated groups The present invention relates to a method for producing an organopolysiloxane having an unsaturated group by base-catalyzed equilibration or condensation. The preparation of functional organopolysiloxanes through alkali-catalyzed equilibration is described in many publications and prior art. For example, catalysts such as alkali metals, ammonium and phosphonium hydroxides or sil(ox)anolates are known from, for example, J. Polym. Sci., Part C No. 16, 669-677 (1967); Makromol. Chem., Macromol. Symp. 6, 67-80 (1986); and Polym. Prepr. 29 (1), 123-125 (1988). EP 628589 B1 describes the use of strontium hydroxide or barium hydroxide with sodium borate or sodium phosphate. However, the method described herein has the disadvantage that the metal hydroxide must be neutralized with acid for inactivation at the end of the reaction. This causes undesirable turbidity and precipitates in the form of salt. EP-A 2055777 describes a multi-step method for producing an organopolysiloxane containing an aminoalkyl group. Herein, the basic catalyst may be inactivated with a long-chain carboxylic acid. The object of the present invention is to provide an advantageous method for producing an unsaturated organopolysiloxane. The object is achieved by the present invention. The present invention relates to a method for manufacturing an organopolysiloxane having unsaturated groups, wherein In the first stage Organopolysiloxane (A) containing units of the following chemical formula (I): In the above chemical formula (I), R may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and Q is an unsaturated hydrocarbon radical that may be the same or different and may include aromatic and/or aliphatic double bonds, and a is 0, 1, 2, or 3, preferably 1, 2, or 3, and b is 0, 1, 2, or 3, preferably 0 or 1, and provided that a+b≤3, and siloxane (A) is an organopolysiloxane (A) having at least one radical Q, Organopolysiloxane (B) containing units of the following chemical formula (II): In the above chemical formula (II), R₂ may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and R1 is an alkyl radical having 1 to 4 carbon atoms that may be the same or different and may be substituted by a hydrogen atom or an oxygen atom, and d is 0, 1, 2, or 3, preferably 2, and f is 0, 1, 2 or 3, preferably 0 or 1, and (B), an organopolysiloxane where d+f≤3 An organopolysiloxane compound (C) optionally comprising at least one structural unit of the following chemical formula (III) per molecule: In the above chemical formula (III), R3 may be the same or different, is a monovalent saturated hydrocarbon radical having 1 to 18 carbon atoms, and is optionally substituted with fluorine, chlorine, or bromine atoms, and Q1 is an unsaturated hydrocarbon radical that may be the same or different and may include aromatic and/or aliphatic double bonds, and Y is a divalent to divalent organic radical having 1 to 30 carbon atoms and may include one or more oxygen atoms, and e is 0 or 1, and c is an integer from 1 to 11, and g is 0 or 1, and However, an organopolysiloxane compound (C) in which e+g≤2, and Basic catalyst (D) selected from the group of alkali metal hydroxides, alkali alcoholates and alkali metal siloxanolates The step of mixing them together, In the second stage A step of reacting the mixture obtained in the first step at a temperature of 80°C to 170°C and In the third stage A step of neutralizing the reaction mixture obtained in the second step using a carboxylic acid derivative (E) having at least four carbon atoms. Includes In the context of the present invention, the term organopolysiloxane is intended to encompass polymeric, oligomeric, and also dimeric siloxanes. Examples of hydrocarbon radicals R, R2 and R3 are each independently alkyl radicals, e.g., methyl, ethyl, n-propyl, isopropyl, 1-n-butyl, 2-n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl radical, hexyl radical, e.g., n-hexyl radical, heptyl radical, e.g., n-heptyl radical, octyl radical, e.g., n-octyl radical, and isooctyl radical, e.g., 2,2,4-trimethylpentyl radical, nonyl radical, e.g., n-nonyl radical, decyl radical, e.g., n-decyl radical, dodecyl radical, e.g., n-dodecyl radical, and octadecyl radical, e.g., n-octadecyl radical; and cycloalkyl radicals, such as cyclopentyl, cyclohexyl, cycloheptyl, and methylcyclohexyl radicals. Examples of substituted radicals R, R2 and R3 are each independently haloalkyl radicals, e.g., 2,2,2,2',2'-hexafluoroisopropyl radical, 3,3,3-trifluoro-n-propyl radical, heptafluoroisopropyl radical, and haloaryl radicals, e.g., o-, m-, and p-chlorophenyl radicals. Preferably, radicals R, R2 and R3 are each independently mono