CN105330864B - Organo-silicon compound and its preparation method and application - Google Patents

Organo-silicon compound and its preparation method and application Download PDF

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CN105330864B
CN105330864B CN201510718569.6A CN201510718569A CN105330864B CN 105330864 B CN105330864 B CN 105330864B CN 201510718569 A CN201510718569 A CN 201510718569A CN 105330864 B CN105330864 B CN 105330864B
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monomer
catalyst
organosilicon compound
silicon compound
preparation
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CN105330864A (en
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刘海峰
李天龙
杨番
王柱
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Institute of Industry Technology Guangzhou of CAS
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Silicon Polymers (AREA)

Abstract

The present invention relates to a kind of organo-silicon compound and its preparation method and application.The organo-silicon compound have the general structure as shown in formula (I), wherein R1, R2Respectively optionally from-CH=CH2,-H；A:b:c:x:z=(0-7): (0-3): (0-3): (1-5): (1-5), and a and c are not 0 simultaneously.The organo-silicon compound, by active site concentrated setting in the middle part of compound molecule, water repellent effect can be preferably played compared with the prior art, while also there is the excellent compatibility with substrate, when being applied to preparation has waterproofing function material, good durability and water repellency can get.

Description

Organosilicon compounds, process for their preparation and their use
Technical Field
The invention relates to the field of organic synthesis, in particular to an organic silicon compound and a preparation method and application thereof.
Background
The basic structural unit of the organosilicon compound is composed of silicon-oxygen links, and the side chains are connected with other various organic groups through silicon atoms. Therefore, the structure of the organic silicon product contains both organic groups and inorganic structures, and the special composition and molecular structure enable the organic silicon product to integrate the characteristics of organic matters and the functions of inorganic matters, and the intermolecular action force of the organic silicon product is much weaker than that of hydrocarbon, so that the organic silicon product has lower viscosity, lower surface tension, lower surface energy and higher film forming capability than hydrocarbon with the same molecular weight. The low surface tension and low surface energy make it hydrophobic to some extent and the price is relatively cheap, thus becoming a hot research point in the field of water repellency.
The prior art discloses a method for waterproof, damp-proof and mildew-proof protection of building materials, ancient buildings and paper by adopting hydrogen-containing silicone oil. However, most of the currently reported organosilicon compounds are mature industrial products, and due to the limitations of the structure (few functional groups, low surface energy, etc.), the organosilicon compounds have poor compatibility with substrates (such as textiles, building materials, etc.), and thus have unsatisfactory water repellency and durability.
Disclosure of Invention
Based on this, there is a need to provide an organosilicon compound.
An organosilicon compound having the structural features shown in formula (I):
wherein R is1，R2Each independently selected from-CH ═ CH2，-H；
a: b: c: x: z ═ 0-7: (0-3): (0-3): (1-5): (1-5), and a and c are not 0 at the same time.
In one of the embodiments, the first and second electrodes are,
(1)c＝0，R1optionally selected from-CH ═ CH2，-H；
a: b: x: z ═ (0.5-7): (0.5-3): (1-5): (1-5); or,
(2)b＝c＝0，R1optionally selected from-CH ═ CH2，-H；
a: x: z ═ (0.5-3): (1.5-5): (1.5-5); or,
(3)R1，R2each independently selected from-CH ═ CH2，-H；
(a + c): b: x: z ═ (0.5-3): (0.5-2): (2.5-5): (2.5-5), and a ≠ 0, c ≠ 0.
In one embodiment, the organosilicon compound has a viscosity of 20 to 10000cst (25 ℃).
The invention also provides a preparation method of the organic silicon compound, which is prepared from the following raw materials in parts by mole:
wherein the monomer A is methyl cyclosiloxane; the monomer B is tetravinyl tetramethyl cyclo tetrasiloxane and/or tetramethyl cyclo tetrasiloxane,
the preparation method comprises the following steps:
pre-mixing 30-70 parts by mole of monomer A and 5-30 parts by mole of monomer B, reacting for 1-3h at 60-150 ℃ under the catalysis of a catalyst, adding the rest of monomer A, continuing to react for 1-6h, and adding an end capping agent for end capping treatment to obtain the organic silicon compound; or,
reacting 5-30 molar parts of monomer B for 1-3h at 60-150 ℃ under the catalysis of a catalyst, adding 100 molar parts of monomer A into the system, continuing to react for 1-6h, and adding an end capping agent for end capping to obtain the organic silicon compound; or,
reacting 5-20 molar parts of monomer A at 60-150 ℃ for 0.5-1h under the catalysis of a catalyst, adding 5-30 molar parts of monomer B, reacting for 0.5-1h, adding the residual monomer A into the system, continuing to react for 1-6h, and adding an end capping agent for end capping to obtain the organic silicon compound.
In one embodiment, the methylcyclosiloxane is octamethylcyclotetrasiloxane and/or hexamethylcyclotrisiloxane.
In one embodiment, the end-capping agent comprises one or more of hexamethyldisiloxane, tetramethyldivinyldisiloxane, polydimethoxysilane end-capping agent, trimethylchlorosilane.
In one embodiment, the catalyst is an acid catalyst or a base catalyst.
In one embodiment, the capping treatment time is 0.5 to 2 hours.
The invention also provides application of the organic silicon compound in preparing a material with a water-repellent function.
The principle and advantages of the invention are as follows:
according to the invention, a large number of experimental research results are integrated, the water repellent function of the organic silicon compound is determined by the distribution condition of active sites in the structure of the compound, and in the prior art, when the organic silicon compound is prepared, all polymerization monomers are synchronously added for polymerization, the active sites in the prepared compound are often irregularly distributed, so that the water repellent material is prepared by crosslinking, and the activity of the dimethyl polysiloxane group with the waterproof function is greatly limited and cannot be freely unfolded, thereby influencing the water repellent function of the material.
Based on the discovery, the invention prepares a series of organosilicon compounds with active sites positioned in the middle of the compounds by reasonably controlling the adding amount and sequence of the monomer (monomer A) providing a polydimethylsiloxane segment and the monomer (monomer B) providing the active sites (preferably vinyl and hydrogen groups), the active sites of the compounds with the structure are intensively arranged in the middle of a silicone oil molecule, the two ends of the compounds are free polydimethylsiloxane segments, after the active groups are crosslinked, the free segments can still freely stretch, a better water repellent effect is exerted, and meanwhile, the organosilicon compounds have excellent compatibility with a substrate, and when the organosilicon compounds are actually applied to the preparation of materials with water repellent function, the organosilicon compounds can obtain good durability and water repellent property.
Compared with the prior art, the invention has the following beneficial effects:
the organic silicon compound has the advantages that the active sites are intensively arranged in the middle of the compound molecules, so that the water repellent effect can be better exerted compared with the prior art, meanwhile, the organic silicon compound has excellent compatibility with a substrate, and when the organic silicon compound is actually applied to preparation of a material with a water repellent function, good durability and water repellency can be obtained.
The preparation method of the organic silicon compound has simple steps, is easy to control and is convenient for industrial application.
Detailed Description
The organosilicon compounds according to the invention, their preparation and their use are described in more detail below with reference to specific examples.
In the embodiment of the invention:
a1: octamethylcyclotetrasiloxane, CAS: 556-67-2;
a2: hexamethylcyclotrisiloxane, CAS: 541-05-9;
b1: tetravinyltetramethylcyclotetrasiloxane, CAS: 2554-06-5;
b2: tetramethylcyclotetrasiloxane, CAS: 2370-88-9.
Example 1
Premixing 30 molar parts of A1 and 30 molar parts of B2, reacting for 1 hour at 120 ℃ under the catalysis of 1 molar part of concentrated sulfuric acid catalyst, adding 70 molar parts of A1 into the system, continuing to react for 3 hours, adding 2 molar parts of hexamethyldisiloxane, reacting and end-capping for 0.5 hour, neutralizing by using an aqueous solution of sodium hydroxide, and finishing the preparation process, wherein functional groups in a reaction product are concentrated in the middle of chain segments of molecules, and the structure can be expressed as:
wherein R is1is-H, R3Is CH3，R4Is CH3(ii) a a: b: x: z is 1:1:1.1:1.1 and its viscosity is 50 cst.
Comparative example 1
Mixing 100 molar parts of A1 and 30 molar parts of B2, reacting for 4 hours at 120 ℃ under the catalysis of 1 molar part of concentrated sulfuric acid catalyst, adding hexamethyldisiloxane for reaction and end-capping for 0.5 hour, and neutralizing by using an aqueous solution of sodium hydroxide to finish the preparation process, wherein functional groups of a reaction product are randomly dispersed in molecules.
And (3) performance comparison:
100 parts of the product obtained in example 1 are mixed with vinyl trimethoxy silane in a stoichiometric ratio and reacted for 24 hours at 80 ℃ in Karstedt's catalyst (0.01 part) to obtain silicone oil of a graft coupling agent, which is marked as a water repellent 1.
100 parts of the product obtained in comparative example 1 and vinyl trimethoxy silane in stoichiometric ratio are mixed and reacted for 24 hours at 80 ℃ in Karstedt catalyst (the using amount is 0.01 part) to obtain silicone oil of the graft coupling agent, which is marked as a water repellent agent 2.
(1) Water repellency test
Dissolving with chloroform to obtain water repellent active liquid with mass fraction of 1%, treating cotton cloth, soaking in two bundles, oven drying at 120 deg.C for 2min, shaping at 160 deg.C for 1min, standing for 4h, and testing water repellency (AATCC 22-2005). The score of example 1 is 90 points, while the score of comparative example 1 is 70 points, the difference is significant.
After the concrete is treated in the same manner, example 1 is not soaked with water after being soaked for 24 hours, and the water repellent effect is remarkable, while comparative example 1 is soaked after being soaked for 24 hours.
(2) Durability test
Washing the cotton cloth subjected to water repellency treatment at 45 ℃ for 15min by using the concentration of 3% of washing powder, washing, drying, and repeating the washing for three times to test the water repellency, wherein the score of the cotton cloth subjected to water repellency treatment is 85 minutes in example 1, and the score of the cotton cloth subjected to water repellency treatment is 65 in comparative example 1.
Example 2
Reacting 20 molar parts of B2 for 1 hour at 60 ℃ under the catalysis of 1 molar part of concentrated sulfuric acid catalyst, adding 100 molar parts of A1 into the system, continuing to react for 3 hours, adding 2 molar parts of tetramethyl divinyl disiloxane, reacting and end-capping for 0.5 hour, and neutralizing by using an aqueous solution of sodium hydroxide to finish the preparation process, wherein functional groups in the reaction product are concentrated in the middle of chain segments of molecules, and the structure can be expressed as:
wherein R is1is-H, R3Is CH ═ CH2，R4Is CH ═ CH2(ii) a a: x: z is 2:5:5 and its viscosity is 500 cst.
AATCC22-2005 scored 95 after grafting the coupling agent according to the water repellency test method of example 1; the durability test score is 90.
Example 3
Reacting 5 molar parts of A1 for 1 hour at 150 ℃ under the catalysis of 0.01 molar part of concentrated sulfuric acid catalyst, adding 20 molar parts of B2 into the system, continuing to react for 1 hour, adding 0.5 molar part of catalyst, adding 95 molar parts of A1, continuing to react for 2 hours, adding 0.5 molar part of singly-terminated polydimethoxysilane end-capping agent (MDM), treating for 0.5 hour, neutralizing by using sodium hydroxide aqueous solution, and finishing the preparation process, wherein the structure of the reaction product can be represented as follows:
wherein R is1And R2is-H; (a + c): b: x: z is 2.1: 0.53: 5:5, a is not equal to 0, c is not equal to 0, and the viscosity is 800 cst.
AATCC22-2005 scored 95 after grafting the coupling agent according to the water repellency test method of example 1; the durability test score was 85.
Example 4
Premixing 30 molar parts of A2 and 20 molar parts of B1, reacting for 3 hours at 60 ℃ under the catalysis of 10 molar parts of Amberlyst-15 catalyst, adding 70 molar parts of A2 into the system, continuing to react for 6 hours, adding 0.2 molar part of hexamethyldisiloxane, reacting and blocking for 0.5 hour, filtering to remove the catalyst, and removing a small amount of unreacted monomer under reduced pressure to finish the preparation process, wherein the structure of the reaction product can be represented as follows:
wherein R is1is-CH ═ CH2，R3Is CH3，R4Is CH3(ii) a a: b: x: z is 3:2:3.5:3.5, the viscosity is 600, and functional groups are concentrated in the middle of the chain segment of the molecule after the coupling agent is grafted.
100 parts of the product obtained in example 4 is mixed with vinyl trimethoxy silane with equal stoichiometric ratio, and the mixture reacts for 24 hours at 80 ℃ in Karstedt catalyst (the using amount is 0.01 part) to obtain silicone oil of a graft coupling agent, wherein the AATCC22-2005 score is 90; the durability test score was 85.
Example 5
Reacting 20 molar parts of B1 for 1 hour at 60 ℃ under the catalysis of 1 molar part of a potassium hydroxide aqueous solution catalyst, adding 100 molar parts of A2 into the system, continuing to react for 3 hours, adding 0.01 molar part of tetramethyl divinyl disiloxane, reacting for end capping for 0.5 hour, neutralizing by using a sulfuric acid aqueous solution, and finishing the preparation process, wherein the structure of a reaction product can be represented as:
wherein R is1is-CH ═ CH2，R3is-CH ═ CH2，R4is-CH ═ CH2(ii) a a: x: z ═ 1:1.9:1.9, viscosity 10000cst, functional groups concentrated in the middle of the segment of the molecule.
AATCC22-2005 scored 90 after grafting the coupling agent according to the water repellency test method of example 1; the durability test score was 85.
Example 6
20 molar parts of A2 in 5 molar parts of SO4 2-/ZrO2Catalysts (catalyst preparation methods see "based on SO4 2-/ZrO2The design of the hybrid catalyst and the application thereof in biodiesel synthesis, doctor thesis of northeast university, 2011, li wei) reacts for 1h under the catalysis of 100 ℃, then 20 mol parts of B1 are added into the system, 0.5 mol part of the catalyst is supplemented to continue the reaction for 1h, 80 mol parts of A2 is added to continue the reaction for 2h, 1 mol part of single-end-capped polydimethoxysilane end-capping agent (MDM) is added to treat for 0.5h, the catalyst is filtered out, the preparation process is completed, and the structure of the reaction product can be expressed as follows:
wherein R is1And R2is-CH ═ CH2，R3、R4Is oligomeric polydimethylsiloxane; (a + c): b: x: and z is 1.3: 1: 2.7: 2.7 and a ≠ 0, c ≠ 0, with a viscosity of 300 cst.
AATCC22-2005 scored 95 after grafting the coupling agent according to the water repellency test method of example 4; the durability test score was 85.
Example 7
Premixing 30 molar parts of A2 and 5 molar parts of B2, reacting for 1 hour at 120 ℃ under the catalysis of 1 molar part of concentrated sulfuric acid catalyst, adding 70 molar parts of A2 into the system, continuing to react for 3 hours, adding 0.7 molar part of hexamethyldisiloxane, reacting and end-capping for 0.5 hour, neutralizing by using an aqueous solution of sodium hydroxide, and finishing the preparation process, wherein functional groups in a reaction product are concentrated in the middle of a chain segment of a molecule, and the structure can be expressed as:
wherein R is1is-H, R3Is CH3，R4Is CH3(ii) a a: b: x: z is 0.71:3:5:5 and its viscosity is 300 cst.
AATCC22-2005 scored 85 after grafting coupling agent according to the water repellency test method of example 1; the durability test scores 80.
Example 8
Reacting 5 molar parts of B1 for 1 hour at 60 ℃ under the catalysis of 1 molar part of sodium hydroxide catalyst, adding 100 molar parts of A2 into the system, continuing to react for 3 hours, adding 0.1 molar part of tetramethyl divinyl disiloxane, reacting and end-capping for 0.5 hour, neutralizing by using sulfuric acid aqueous solution, and finishing the preparation process, wherein functional groups in the reaction product are concentrated in the middle of chain segments of molecules, and the structure can be expressed as:
wherein R is1is-CH ═ CH2，R3is-CH ═ CH2，R4is-CH ═ CH2(ii) a a: x: z is 0.67: 5:5, its viscosity is 9000 cst.
AATCC22-2005 scored 90 after grafting coupling agent according to the water repellency test method of example 4; the durability test score was 85.
Example 9
Reacting 20 molar parts of A2 for 1 hour at 150 ℃ under the catalysis of 0.01 molar part of concentrated sulfuric acid catalyst, adding 5 molar parts of B1 into the system, continuing the reaction for 1 hour without adding 0.5 molar part of catalyst, adding 80 molar parts of A2 for continuing the reaction for 2 hours, adding 2 molar parts of singly-terminated polydimethoxysilane end-capping reagent (MDM) for treating for 0.5 hour, and neutralizing by using sodium hydroxide aqueous solution to finish the preparation process, wherein the structure of the reaction product can be represented as follows:
wherein R is1And R2is-CH ═ CH2，R3、R4Oligomeric poly (dimethoxysilane); (a + c): b: x: z is 1.58: 0.53: 5:5, a is not equal to 0, c is not equal to 0, and the viscosity is 90 cst.
AATCC22-2005 scored 95 after grafting the coupling agent according to the water repellency test method of example 4; the durability test score is 90.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.

Claims (7)

1. An organosilicon compound having the structural features shown in formula (I):
wherein,
R1，R2each independently selected from-CH ═ CH2，-H；
(a + c): b: x: z ═ (0.5-3): (0.5-2): (2.5-5): (2.5-5), and a is not equal to 0, and c is not equal to 0;
R3，R4are independently selected from CH3、CH＝CH2Oligomeric polydimethylsiloxanes.
2. The organosilicon compound of claim 1 having a viscosity of from 20 to 10000 cst.
3. The process for producing an organosilicon compound according to claim 1 or 2, which comprises the following steps in parts by mole:
wherein the monomer A is methyl cyclosiloxane; the monomer B is tetravinyl tetramethylcyclotetrasiloxane and/or tetramethylcyclotetrasiloxane, and the end-capping agent comprises one or more of hexamethyldisiloxane, tetramethyldivinyldisiloxane, polydimethoxysilane end-capping agent and trimethylchlorosilane;
the preparation method comprises the following steps:
reacting 5-20 molar parts of monomer A for 0.5-1h at 60-150 ℃ under the catalysis of a catalyst, adding 5-30 molar parts of monomer B, reacting for 0.5-1h, adding the residual monomer A into the system, continuing to react for 1-6h, and adding an end capping agent for end capping to obtain the organic silicon compound.
4. The method for producing an organosilicon compound according to claim 3, wherein the methylcyclosiloxane is octamethylcyclotetrasiloxane and/or hexamethylcyclotrisiloxane.
5. The method for producing an organosilicon compound according to claim 3 or 4, wherein the catalyst is an acid catalyst or a base catalyst.
6. The method of producing an organosilicon compound according to claim 3 or 4, wherein the time of the end-capping treatment is 0.5 to 2 hours.
7. Use of the organosilicon compound according to claim 1 for the production of materials having a water-repellent function.
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