CN113880874A - Preparation method of poly [ propoxypiperidinyl (methyl) siloxane ] compound - Google Patents

Preparation method of poly [ propoxypiperidinyl (methyl) siloxane ] compound Download PDF

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CN113880874A
CN113880874A CN202111223445.2A CN202111223445A CN113880874A CN 113880874 A CN113880874 A CN 113880874A CN 202111223445 A CN202111223445 A CN 202111223445A CN 113880874 A CN113880874 A CN 113880874A
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poly
catalyst
siloxane
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刘恩静
袁开锋
杨紫伟
胡新利
陈超
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Suqian Unitechem Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
    • C07F7/0878—Si-C bond
    • C07F7/0879—Hydrosilylation reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/02—Flame or fire retardant/resistant
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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Abstract

The invention relates to a preparation method of a poly [ propoxypiperidinyl (methyl) siloxane ] compound, which comprises the following steps: adding raw materials of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, poly (methylhydrogensiloxane) and a solvent into a reaction kettle, carrying out heat preservation reaction at 90-100 ℃, and carrying out negative pressure distillation after the reaction is finished to finally obtain a distillation product poly [ propoxypiperidyl (methyl) siloxane ] compound; and can obtain high-content products, thus being a more ideal process for realizing industrialization.

Description

Preparation method of poly [ propoxypiperidinyl (methyl) siloxane ] compound
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of a poly [ propoxypiperidinyl (methyl) siloxane ] compound.
Background
The content of organic silicon chemical research mainly comprises the formation of chemical bonds such as silicon-carbon bonds, silicon-hydrogen bonds, silicon-oxygen bonds, silicon-nitrogen bonds, silicon-silicon bonds and the like and the properties of corresponding substances. The formation of silicon-carbon bond plays a very important role in the organic silicon chemical research, because the combination of organic group mainly containing carbon and silicon element through the silicon-carbon bond endows the silicon element with the properties of organic compounds, so that the element widely existing in inorganic compounds has wide industrial application prospect. To date, there are two main methods of forming silicon-carbon bonds that have industrial application: the method is a Rochow direct synthesis method which takes silicon powder and halogenated hydrocarbon as raw materials; the second is hydrosilylation, which uses hydrogen-containing silane or siloxane and organic compound containing unsaturated bond as raw materials. The Rochow direct method is generally used for the synthesis of organosilicon monomers such as methyl halosilanes, phenyl halosilanes, etc., while the hydrosilylation method is widely used for the synthesis of downstream products of organosilicon, which can convert the organohalosilanes synthesized in the former into diverse products. It follows that hydrosilylation has an irreplaceable role in extending the silicone product chain. Platinum catalysts are most widely used in hydrosilylation reactions. The deep discussion of the catalytic mechanism of the platinum catalyst in the hydrosilylation reaction and the performance of various platinum catalysts has very important guiding significance for understanding and applying the hydrosilylation reaction.
As for the organosilicon flame retardant, polysiloxane is the most representative, and the silicone resin and the silicone oil are taken as main components. The polysiloxane is a polymer, can be well compatible with the polymer, improves the binding force of the polysiloxane and the polymer, and reduces the migration probability of the flame retardant component. When the organic silicon fire retardant is burnt, the-SiO-bond in the molecule can be converted into-Si-C-bond, and the-Si-C-bond and the generated carbide form a composite carbon layer. The composite carbon layer has the advantages of heat resistance, oxygen isolation and molten drop prevention, can seal high molecular material to prevent combustible gas from diffusing outwards, and can be added with organosilicon flame retardant into magnesium hydroxide (Mg (OH)2) Aluminum hydroxide (Al (OH)3) And the inorganic flame retardant is used for surface modification. The modified inorganic flame retardant has high dispersity, can be well compatible with a high molecular compound, has small addition amount and low mobility, and can reduce the influence on the mechanical property and other properties of the original base material.
At present, the methods for preparing poly [ propoxypiperidinyl (methyl) siloxane ] compound compounds are physical mixing methods and homogeneous synthesis methods.
For homogeneous synthesis:
the research on the catalytic mechanism of hydrosilylation reaction of Duzhongjun, Lifeng instrument and Deng Fengjie is advanced [ J ]. organosilicon material (6): 312-.
The research trends and the developments of three catalytic mechanisms (free radical addition mechanism), ion addition mechanism and coordination addition mechanism of hydrosilylation are reviewed, and the platinum catalytic mechanism (Chalk-Harrod mechanism, silicon-based migration, platinum colloid transition state mechanism, cobalt catalytic mechanism, rhodium catalytic mechanism, ruthenium catalytic mechanism, palladium catalytic mechanism, nickel catalytic mechanism and the like) in the coordination addition mechanism are emphatically introduced
Lijia, preparation of organosilicon modified acrylate waterproof coating and performance research [ D ]. Nanjing university of science and technology, 2005.
Hydroxysilicones are prepared by anionic ring-opening polymerization of octamethylcyclotetrasiloxane in the presence of hydroxide as catalyst, and hydroxide and Me are discussed3Catalytic efficiency of NOH. The hydroxyl silicone oil is condensed with methyl dichlorosilane in the presence of triethylamine to prepare the hydrogen-containing silicone oil. Active silicon hydrogen bonds in the hydrogen-containing silicone oil and a double bond in the allyl methacrylate are used for carrying out hydrosilylation reaction, and an organic silicon graft modified AMA monomer (Si-AMA) is synthesized. And the infrared spectrum is utilized to carry out structural characterization on the hydroxyl silicone oil, the hydrogen-containing silicone oil and the Si-AMA. Si-AMA, Methyl Methacrylate (MMA), Butyl Acrylate (BA), hydroxyethyl methacrylate (HEMA) and gamma-methacryloxypropyltrimethoxysilane (KH-570) are copolymerized into the organosilicon modified acrylate resin by adopting a traditional free radical solution polymerization method.
Currently, the hydrosilylation catalyst system commonly used in the industry is the Speier's catalyst (hexachloroplatinic acid solution), but the catalyst has limitations: firstly, the Pt homogeneous catalyst has poor separation and recycling performance; and secondly, when Si in the hydrogen-containing silane is connected with an electron donating functional group or an unsaturated bond is connected with a strong electron withdrawing group, effective addition can not be carried out. The synthesis of the existing method has certain problems, such as long reaction induction period, byproduct generation, poor stereoselectivity and the like.
Disclosure of Invention
In order to solve the problems of low compatibility and high mobility of the existing flame retardant and hindered amine light stabilizer with polymers, the invention provides a novel silicon-containing hindered amine structure and synthesizes the novel silicon-containing light stabilizer; the invention has good application prospect and economic benefit.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a poly [ propoxypiperidinyl (methyl) siloxane ] compound having the formula:
Figure 391033DEST_PATH_IMAGE001
；
wherein n is an integer of 1 to 4.
A preparation method of a poly [ propoxypiperidinyl (methyl) siloxane ] compound comprises the following synthetic process routes:
Figure DEST_PATH_IMAGE002
；
wherein n is an integer of 1 to 4.
As an improvement of the invention, the synthesis process comprises the following steps: mixing 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, a solvent, poly (methylhydrogensiloxane) and a catalyst, and then carrying out heat preservation reaction; after the reaction is finished, the reaction solution is distilled under negative pressure, and the poly [ propoxypiperidinyl (methyl) siloxane ] compound can be obtained.
As a modification of the invention, the molar ratio of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine to poly (methylhydrogensiloxane) is 1: 3 to 8.
As an improvement of the invention, the mass ratio of the solvent to the total mass of the 4-allyloxy-2, 2,6, 6-tetramethylpiperidine and the poly (methylhydrogensiloxane) is 1: 0.5 to 1.
According to an improvement of the invention, the mass ratio of the catalyst to the total mass of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, solvent and poly (methylhydrogensiloxane) is 0.0005-0.0015: 1.
as a modification of the invention, the solvent is one of toluene, xylene, dichloromethane, isopropanol and dioxane.
As an improvement of the invention, the catalyst is one of a platinum catalyst, a Wilkinson rhodium catalyst, a nickel catalyst, an organosilicon high molecular metal catalyst and a Karstedt catalyst.
As an improvement of the invention, the temperature of the heat preservation reaction is 90-100 ℃.
As an improvement of the invention, the heat preservation time is 8-12 hours.
As an improvement of the invention, the temperature of the negative pressure distillation is 85-105 ℃.
Due to the adoption of the technology, compared with the existing light stabilizer product, the light stabilizer has the following beneficial effects:
the novel composite flame retardant provided by the invention is used as a composite light stabilizer with light stability and flame retardance, and is non-toxic and harmless in preparation and production, mild in reaction conditions and high in yield. The silicon series flame retardant has no halogen, and has the advantages of high efficiency, low smoke, no pollution and the like.
Drawings
FIG. 1 is an infrared spectrum of a poly [ propoxypiperidinyl (methyl) siloxane ] compound obtained in example 1;
FIG. 2 is a HNMR map of the poly [ propoxypiperidyl (methyl) siloxane ] compound obtained in example 2.
Detailed Description
The present invention will be further illustrated with reference to the accompanying drawings and specific embodiments, which are to be understood as merely illustrative of the invention and not as limiting the scope of the invention.
Example 1
In a 500mL four-necked flask equipped with a thermometer, 16.8g (0.08 mol) of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, 89g (0.4 mol) of hydrogen-containing silicone oil, 125g of toluene, and 0.25g of platinum catalyst were charged. And (3) installing a stirrer and a condenser pipe, heating to 95 ℃ for heat preservation reaction, and reacting for 8 hours. Then cooling to room temperature, and carrying out reduced pressure rectification at the temperature of 85 ℃ to obtain a colorless transparent liquid product poly [ propoxypiperidinyl (methyl) siloxane ] compound.
The target product prepared in this example was detected by an infrared spectrometer, the infrared spectrum is shown in figure 1,
the infrared characteristic peak position is 2130cm-1Is a stretching vibration peak of Si-H, and in an infrared spectrogram of a sample, an absorption peak disappears, and simultaneously, the position of an infrared characteristic peak of Si-OH is 3690cm-1The peak of the product is 3690cm-1The position has no response peak, which indicates that all Si-H bonds in the raw materials participate in the reaction. 1166cm-1A C-O-C stretching vibration peak appears nearby, which indicates that the silicon-hydrogen bond participates in the reaction and does not disappear through hydrolysis.
Example 2
In a 500mL four-necked flask equipped with a thermometer, 20g (0.09 mol) of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, 89g (0.4 mol) of hydrogen-containing silicone oil, 125g of toluene, and 0.28g of platinum catalyst were charged. Installing a stirrer and a condenser pipe, heating to 100 ℃ for heat preservation reaction, and reacting for 12 hours. Then cooling to room temperature, and carrying out vacuum rectification at the temperature of 90 ℃ to obtain a colorless transparent liquid product poly [ propoxypiperidinyl (methyl) siloxane ] compound.
Detecting the target product prepared in the embodiment through nuclear magnetism, wherein an absorption peak of delta-0.12-0.3 ppm belongs to an Si-Me peak on siloxane; 1HNMR (400MHz, D2O): delta 3.62(m, 1H), delta 3.40 (t, 2H), delta 1.93 (m, 2H), delta 1.57 (m, 2H), delta 1.16 (s, 7H), delta 1.11 (s, 6H), delta 0.97 (t, 2H), delta 0.48 (t, 2H). The HNMR map is shown in FIG. 2.
Example 3
In a 500mL four-necked flask equipped with a thermometer, 25.2g (0.12 mol) of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, 133.5g (0.6 mol) of hydrogen-containing silicone oil, 200g of xylene, and 0.25g of Karstedt's catalyst were charged. And (3) installing a stirrer and a condenser pipe, heating to 95 ℃ for heat preservation reaction, and reacting for 10 hours. Then cooling to room temperature, and carrying out reduced pressure rectification at 105 ℃ to obtain a colorless transparent liquid product poly [ propoxypiperidinyl (methyl) siloxane ] compound.
Example 4
In a 1000mL four-necked flask equipped with a thermometer, 25.2g (0.12 mol) of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, 200.25g (0.9 mol) of hydrogen-containing silicone oil, 300g of xylene, and 0.3g of Karstedt's catalyst were charged. Installing a stirrer and a condenser pipe, heating to 100 ℃ for heat preservation reaction, and reacting for 12 hours. Then cooling to room temperature, and carrying out reduced pressure rectification at 105 ℃ to obtain a colorless transparent liquid product poly [ propoxypiperidinyl (methyl) siloxane ] compound.
Example 5
The comparative materials were a silicone resin and a silicone flame retardant poly [ propoxypiperidinyl (methyl) siloxane ] compound prepared in example 3 of the present invention. The silicone resin and the silicone flame retardant prepared in example 3 were uniformly mixed with the polypropylene master batch in proportions of 5 wt%, 10 wt%, 15 wt%, and 20wt%, respectively, and injection molded to prepare a polypropylene sample.
And (3) keeping the injection pressure at 30-50 Mpa by using nitrogen for 8s, and cooling for 25 s. The injection molding process temperature: the nozzle is used for heating at 195 deg.C, 185 deg.C, 180 deg.C, 25 deg.C and 25 deg.C. The tensile strength and the elongation at break retention are tested according to GB/T1040-96, and a universal testing machine is used for testing, and the testing speed is 20 mm/min. The test results are shown in tables 1 and 2.
According to the test results, the LOI value of the PP/silicone resin blending system is larger along with the increase of the adding amount of the silicone resin as the flame-retardant component. If the addition amount of the flame retardant component silicone resin is 20wt%, the LOI value of the PP/silicone resin blending system is increased to 23.6% from 17.5% of a pure PP polymeric material. In addition, when the limit oxygen fraction test is carried out on the mixed material, a molten drop phenomenon occurs, theoretically, the molecular weight of the synthesized organic silicon resin is small, or the chain segment of the polymerized organic silicon resin contains an active functional group (-OH), so that the thermal stability of the organic silicon resin is reduced, and the flame retardant property of the organic silicon resin is poor. As can be seen from the data in the silicone flame retardant table, the limiting oxygen index also gradually increased with increasing amounts of silicone flame retardant added. If 20% of organosilicon flame retardant is added, the LOI value of the flame-retardant polypropylene system is increased from 17.5% to 24.8%, which is increased by 29.4%. The heat stability is better, and the flame-retardant polypropylene has better effect. The data of the organic silicon resin and the organic silicon flame retardant are compared, and the flame retardant property of the organic silicon flame retardant is superior to that of the organic silicon resin with the corresponding composition.
TABLE 1 Silicone resin and PP blend formulations and oxygen index test results
Figure DEST_PATH_IMAGE003
TABLE 2 organosilicon flame retardant and PP blending formulation and oxygen index test results
Figure DEST_PATH_IMAGE004
The mechanical property test data (table 3) of the polypropylene mixed system before and after the addition of the flame retardant component can be seen: after the polypropylene base material is added with the organic silicon resin and the organic silicon flame retardant, the tensile property and the elongation at break are obviously reduced, and the larger the adding amount of the flame retardant component is, the more serious the tensile strength and the half-reduction of the elongation at break are. Compared with the elongation at break, the variation trend of the tensile strength is smaller in amplitude, and the variation of the elongation at break string is more obvious.
TABLE 3 tensile Properties test results of Silicone resin and Silicone flame retardant on PP
Figure DEST_PATH_IMAGE005
It should be noted that the above-mentioned contents only illustrate the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and it is obvious to those skilled in the art that several modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations fall within the protection scope of the claims of the present invention.

Claims (10)

1. A poly [ propoxypiperidinyl (methyl) siloxane ] compound having the following structural formula:
Figure DEST_PATH_IMAGE001
；
wherein n is an integer of 1 to 4.
2. A preparation method of a poly [ propoxypiperidinyl (methyl) siloxane ] compound is characterized in that the synthetic process route is as follows:
Figure 401484DEST_PATH_IMAGE002
；
wherein n is an integer of 1 to 4.
3. The method for preparing a poly [ propoxypiperidinyl (methyl) siloxane ] compound according to claim 2, comprising the steps of: mixing 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, a solvent, poly (methylhydrogensiloxane) and a catalyst, and then carrying out heat preservation reaction; after the reaction is finished, the reaction solution is distilled under negative pressure, and the poly [ propoxypiperidinyl (methyl) siloxane ] compound can be obtained.
4. The method of claim 3, wherein the molar ratio of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine to poly (methylhydrogensiloxane) is 1: 3 to 8.
5. The production method according to claim 3, wherein the mass ratio of the solvent to the total mass of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine and poly (methylhydrogensiloxane) is 1: 0.5 to 1.
6. The preparation method according to claim 3, wherein the mass ratio of the catalyst to the total mass of 4-allyloxy-2, 2,6, 6-tetramethylpiperidine, the solvent and poly (methylhydrogensiloxane) is 0.0005 to 0.0015: 1.
7. the method according to claim 3, wherein the solvent is one of toluene, xylene, methylene chloride, isopropyl alcohol, and dioxane.
8. The method according to claim 3, wherein the catalyst is one of a platinum catalyst, a Wilkinson rhodium catalyst, a nickel catalyst, a silicone high-molecular metal catalyst, and a Karstedt catalyst.
9. The preparation method according to claim 3, wherein the temperature of the heat preservation reaction is 90-100 ℃ and the heat preservation time is 8-12 hours.
10. The method according to claim 3, wherein the temperature of the negative pressure distillation is 85 to 105 ℃.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5514738A (en) * 1994-01-24 1996-05-07 Ciba-Geigy Corporation 1-hydrocarbyloxy-piperidine compounds containing silane groups for use as stabilizers for organic materials
US20020040145A1 (en) * 1999-02-25 2002-04-04 Galbo James P. Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith
US20030232910A1 (en) * 2002-06-05 2003-12-18 Mcdermott Phillip J. Thixotropic catalyst for condensation cure siloxane materials

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5514738A (en) * 1994-01-24 1996-05-07 Ciba-Geigy Corporation 1-hydrocarbyloxy-piperidine compounds containing silane groups for use as stabilizers for organic materials
US20020040145A1 (en) * 1999-02-25 2002-04-04 Galbo James P. Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith
US20030232910A1 (en) * 2002-06-05 2003-12-18 Mcdermott Phillip J. Thixotropic catalyst for condensation cure siloxane materials

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HOLGER FRIEDRICH ET AL: "Polymeric light stabilizers based on siloxanes", POLYMER DEGRADATION AND STABILITY, vol. 42, 31 December 1993 (1993-12-31), pages 127 - 144 *

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