CN105330864B - Organo-silicon compound and its preparation method and application - Google Patents
Organo-silicon compound and its preparation method and application Download PDFInfo
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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
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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
- C08G77/06—Preparatory processes
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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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
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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
Technical field
The present invention relates to organic synthesis fields, more particularly to a kind of organo-silicon compound and its preparation method and application.
Background technique
The basic structural unit of organo-silicon compound is made of silicon-oxygen chain link, and side chain then passes through silicon atom and other
Various organic groups are connected.Therefore, not only contain " organic group " in the structure of organosilicon product, but also contain " inorganic structure ",
The function of characteristic and inorganic matter that this special composition and molecular structure make it integrate organic matter, and its intermolecular work
Firmly more much weaker than hydrocarbon therefore lower than the hydrocarbon viscosity of same molecular weight, surface tension is weak, surface energy
Small, film forming ability is strong.This low surface tension and low-surface-energy make it have certain hydrophobic performance, and its price is relatively just
Preferably, thus it is increasingly becoming the research hotspot in water repellent field.
The prior art is just disclosed using containing hydrogen silicone oil for the waterproofs of building materials, ancient architecture building waterproofing, moisture-proof, mould proof protection
And the mould proof method of waterproof of paper.But organo-silicon compound used in reporting at present are mostly mature industrial goods, due to
This body structure still has some limitations (functional group is few, surface energy is low), with substrate (such as textile, construction material etc.)
Compatibility is poor, causes water repellency, durability not ideal enough.
Summary of the invention
Based on this, it is necessary to provide a kind of organo-silicon compound.
Organo-silicon compound with the structure feature 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.
In one of the embodiments,
(1) c=0, R1Optionally from-CH=CH2,-H；
A:b:x:z=(0.5-7): (0.5-3): (1-5): (1-5)；Or,
(2) b=c=0, R1Optionally from-CH=CH2,-H；
A:x:z=(0.5-3): (1.5-5): (1.5-5)；Or,
(3)R1, R2Respectively optionally 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.
The viscosity of the organo-silicon compound is 20-10000cst (25 DEG C) in one of the embodiments,.
The present invention also provides the preparation methods of the organo-silicon compound, in terms of molfraction, are prepared by the following raw material
It forms:
Wherein, the monomer A is methyl cyclosiloxane；Monomer B is tetravinyl tetramethyl-ring tetrasiloxane and/or tetramethyl
Basic ring tetrasiloxane,
Preparation method includes the following steps:
30-70 molar part monomer A and 5-30 molar part monomer B is pre-mixed, under catalyst 60-150 DEG C it is anti-
1-3h is answered, remaining monomer A is added, the reaction was continued 1-6h is added end-capping reagent and carries out termination process to get the organosilicon compound
Object；Or,
By 5-30 molar part monomer B under catalyst 60-150 DEG C of reaction 1-3h, then 100 molar part monomer A are added
Enter in system, the reaction was continued 1-6h, end-capping reagent is added and carries out termination process to get the organo-silicon compound；Or,
Add by 60-150 DEG C of reaction 0.5-1h under 5-20 molar part monomer A catalyst, then by 5-30 molar part monomer B
Enter, reacts in remaining monomer A addition system, the reaction was continued 1-6h after 0.5-1h, end-capping reagent is added and carries out termination process, i.e.,
Obtain the organo-silicon compound.
The methyl cyclosiloxane is octamethylcy-clotetrasiloxane and/or pregnancy basic ring three in one of the embodiments,
Siloxanes.
The end-capping reagent includes hexamethyldisiloxane, two silicon oxygen of tetramethyl divinyl in one of the embodiments,
One of alkane, poly- dimethoxysilane closure agent, trim,ethylchlorosilane are a variety of.
The catalyst is acid catalyst or base catalyst in one of the embodiments,.
The time of the termination process is 0.5-2h in one of the embodiments,.
The present invention also provides application of the organo-silicon compound in the material that preparation has waterproofing function.
The principle of the present invention and advantage are as follows:
The comprehensive a large amount of experimental studies results discovery of the present invention, the fine or not key of the waterproofing function of organo-silicon compound depend on
The distribution situation of active site in compound structure, and the prior art is when preparing organo-silicon compound, it is synchronous that each gather is added
It closes monomer to be polymerize, active site is often in irregular distribution in the compound being prepared, and thus crosslinking, which is prepared, refuses
Water functional material, the polydimethylsiloxane group activity with water-proof function cannot freely be unfolded by larger limitation, from
And influence the performance of material waterproofing function.
Based on the discovery, the present invention by rationally control provide the monomer (monomer A) of polydimethylsiloxane group section with
And the additional amount and sequence of the monomer (monomer B) of active site (preferably vinyl and hydrogen-based) are provided, it is prepared a series of
Active site is located at the organo-silicon compound of compound medium position, with the structure compound activity site concentrated setting in
In the middle part of silicone molecule, both ends are free PolydimethylsiloxaneChain Chain sections, and after active group crosslinks, free segment still can
It is enough freely to unfold, preferable water repellent effect is played, while also there is the excellent compatibility with substrate, is being applied to prepare
When with waterproofing function material, good durability and water repellency can get.
Compared with prior art, the invention has the following advantages:
Organo-silicon compound of the present invention can relatively show by active site concentrated setting in the middle part of compound molecule
There is technology preferably to play water repellent effect, while also there is the excellent compatibility with substrate, has being applied to preparation
When waterproofing function material, good durability and water repellency can get.
The preparation method of organo-silicon compound of the present invention, step is simple, easily controllable, is convenient for industrial applications.
Specific embodiment
Organo-silicon compound of the invention and its preparation method and application are made below in conjunction with specific embodiment further detailed
Thin explanation.
In embodiments of the present invention:
A1: octamethylcy-clotetrasiloxane, CAS:556-67-2；
A2: hexamethyl cyclotrisiloxane, CAS:541-05-9；
B1: tetravinyl tetramethyl-ring tetrasiloxane, CAS:2554-06-5；
B2: tetramethyl-ring tetrasiloxane, CAS:2370-88-9.
Embodiment 1
30 molar part A1 and 30 molar part B2 are pre-mixed, 120 DEG C of reactions under the catalysis of 1 molar part concentrated sulfuric acid catalyst
1h, then by 70 molar part A1 addition systems, the reaction was continued 3h, 2 molar part hexamethyldisiloxane are added and react termination process
0.5h is neutralized using sodium hydrate aqueous solution, completes preparation process, and functional group concentrates on the chain of molecule in reaction product at this time
Section middle part, structure may be expressed as:
Wherein, R1For-H, R3For CH3, R4For CH3；A:b:x:z=1:1:1.1:1.1, viscosity 50cst.
Comparative example 1
100 molar part A1 are mixed with 30 molar part B2,120 DEG C of reaction 4h under the catalysis of 1 molar part concentrated sulfuric acid catalyst,
Hexamethyldisiloxane is added and reacts termination process 0.5h, is neutralized using sodium hydrate aqueous solution, completes preparation process, reaction produces
Object functional group random dispersion is in molecule.
Performance comparison:
By 100 parts of 1 products therefroms of embodiment with etc. the vinyltrimethoxysilanes of stoichiometric ratios mix,
80 DEG C of reactions of Karstedt catalyst (dosage is 0.01 part) for 24 hours, obtain the silicone oil of Grafting-coupling Agent, are labeled as water repellent 1.
By 100 parts of 1 products therefroms of comparative example with etc. the vinyltrimethoxysilanes of stoichiometric ratios mix,
80 degrees Celsius of reactions of Karstedt catalyst (dosage is 0.01 part) for 24 hours, obtain the silicone oil of Grafting-coupling Agent, are labeled as water repellent
2。
(1) water repellent measure of merit
It is dissolved with chloroform, is prepared into the water repellent activity liquid of mass fraction 1%, handle cotton, two leachings two are pricked, 120 DEG C of bakings
Dry 2min, 160 DEG C of sizing 1min after placing 4h, are tested water repellency (AATCC22-2005).Embodiment 1 is scored at 90 points, and
Comparative example 1 is scored at 70 points, significant difference.
After handling concrete in the same way, the water after impregnating for 24 hours of embodiment 1 does not infiltrate, water repellent significant effect, and right
Ratio 1 infiltrates afterwards for 24 hours in immersion.
(2) durability test
With 3% washing powder concentration, by above-mentioned water repellent, treated that cotton is rinsed well after 45 DEG C of washing 15min, drying,
Test water repellent effect afterwards in triplicate, embodiment 1 is scored at 85 points, and comparative example 1 is scored at 65.
Embodiment 2
By 20 molar part B2 1 molar part concentrated sulfuric acid catalyst catalysis under 60 DEG C of reaction 1h, then by 100 molar part A1 addition
In system, the reaction was continued 3h is added 2 molar part tetramethyl divinyl disiloxanes and reacts termination process 0.5h, uses hydrogen-oxygen
Change sodium water solution to neutralize, complete preparation process, functional group concentrates in the middle part of the segment of molecule in reaction product at this time, and structure can
It indicates are as follows:
Wherein, R1For-H, R3For CH=CH2, R4For CH=CH2；A:x:z=2:5:5, viscosity 500cst.
According to the water repellent effect testing method of embodiment 1, the AATCC22-2005 score 95 after Grafting-coupling Agent；Durability
Test score 90.
Embodiment 3
By 5 molar part A1 under the catalysis of 0.01 molar part concentrated sulfuric acid catalyst 150 DEG C of reaction 1h, then 20 molar part B2 are added
Enter in system, the reaction was continued 1h, is added after 0.5 molar part of catalyst and is added 95 molar part A1 the reaction was continued 2h, be added 0.5 mole
Poly- dimethoxysilane closure agent (MDM) the processing 0.5h that part singly blocks, is neutralized, prepared by completion using sodium hydrate aqueous solution
Journey, reaction product structure may be expressed as: at this time
Wherein, R1And R2For-H；(a+c): b:x:z=2.1:0.53:5:5, and a ≠ 0, c ≠ 0, viscosity 800cst.
According to the water repellent effect testing method of embodiment 1, the AATCC22-2005 score 95 after Grafting-coupling Agent；Durability
Test score 85.
Embodiment 4
30 molar part A2 and 20 molar part B1 are pre-mixed, 60 under 10 molar part Amberlyst-15 catalysts
DEG C reaction 3h, then by 70 molar part A2 addition systems, the reaction was continued 6h, the reaction of 0.2 molar part hexamethyldisiloxane is added
Termination process 0.5h is removed by filtration catalyst, and removed under reduced pressure on a small quantity react at this time and produce by unreacted monomer, completion preparation process
Object structure may be expressed as:
Wherein, R1For-CH=CH2, R3For CH3, R4For CH3；A:b:x:z=3:2:3.5:3.5, viscosity 600, through connecing
Functional group concentrates in the middle part of the segment of molecule after branch coupling agent.
By 100 parts of 4 products therefroms of embodiment with etc. the vinyltrimethoxysilanes of stoichiometric ratios mix,
80 degrees Celsius of reactions of Karstedt catalyst (dosage is 0.01 part) for 24 hours, obtain the silicone oil of Grafting-coupling Agent, AATCC22-2005
Score 90；Durability test score 85.
Embodiment 5
By 20 molar part B1 under 1 molar part potassium hydroxide aqueous solution catalyst 60 DEG C of reaction 1h, then by 100 moles
In part A2 addition system, the reaction was continued 3h, addition 0.01 molar part tetramethyl divinyl disiloxane reaction termination process
0.5h is neutralized using aqueous sulfuric acid, completes preparation process, reaction product structure may be expressed as: at this time
Wherein, R1For-CH=CH2, R3For-CH=CH2, R4For-CH=CH2；A:x:z=1:1.9:1.9, viscosity are
10000cst, functional group concentrate in the middle part of the segment of molecule.
According to the water repellent effect testing method of embodiment 1, the AATCC22-2005 score 90 after Grafting-coupling Agent；Durability
Test score 85.
Embodiment 6
By 20 molar part A2 in 5 molar part SO4 2-/ZrO2(method for preparing catalyst is referring to " based on SO for catalyst4 2-/ZrO2
Hybrid catalyst design and its biodiesel synthesis in application ", Northeast Normal University's doctoral thesis, 2011, Li Wei)
It is catalyzed lower 100 DEG C of reactions 1h, then 0.5 molar part of catalyst in 20 molar part B1 addition systems, will be added the reaction was continued 1h, is added
80 molar part A2 the reaction was continued 2h, the poly- dimethoxysilane closure agent (MDM) that 1 molar part list sealing end is added handle 0.5h, filter
Except catalyst, preparation process is completed, reaction product structure may be expressed as: at this time
Wherein, R1And R2For-CH=CH2, R3、R4For oligomerization dimethyl silicone polymer；(a+c): b:x:z=1.3:1:2.7:
2.7, and a ≠ 0, c ≠ 0, viscosity 300cst.
According to the water repellent effect testing method of embodiment 4, the AATCC22-2005 score 95 after Grafting-coupling Agent；Durability
Test score 85.
Embodiment 7
30 molar part A2 and 5 molar part B2 are pre-mixed, 120 DEG C of reactions under the catalysis of 1 molar part concentrated sulfuric acid catalyst
1h, then in 70 molar part A2 addition systems, the reaction was continued 3h is added at 0.7 molar part hexamethyldisiloxane reaction sealing end
0.5h is managed, is neutralized using sodium hydrate aqueous solution, completes preparation process, functional group concentrates on molecule in reaction product at this time
In the middle part of segment, structure be may be expressed as:
Wherein, R1For-H, R3For CH3, R4For CH3；A:b:x:z=0.71:3:5:5, viscosity 300cst.
According to the water repellent effect testing method of embodiment 1, the AATCC22-2005 score 85 after Grafting-coupling Agent；Durability
Test score 80.
Embodiment 8
By 5 molar part B1 under the catalysis of 1 molar part sodium hydroxide catalyst 60 DEG C of reaction 1h, then 100 molar part A2 are added
Enter in system, the reaction was continued 3h, addition 0.1 molar part tetramethyl divinyl disiloxane reaction termination process 0.5h, use
Aqueous sulfuric acid neutralizes, and completes preparation process, and functional group concentrates in the middle part of the segment of molecule in reaction product at this time, and structure can
It indicates are as follows:
Wherein, R1For-CH=CH2, R3For-CH=CH2, R4For-CH=CH2；A:x:z=0.67:5:5, viscosity are
9000cst。
According to the water repellent effect testing method of embodiment 4, the AATCC22-2005 score 90 after Grafting-coupling Agent；Durability
Test score 85.
Embodiment 9
By 20 molar part A2 under the catalysis of 0.01 molar part concentrated sulfuric acid catalyst 150 DEG C of reaction 1h, then 5 molar part B1 are added
Enter in system, be not added 0.5 molar part of catalyst the reaction was continued 1h, is added 80 molar part A2 the reaction was continued 2h, 2 molar part lists are added
The poly- dimethoxysilane closure agent (MDM) of sealing end handles 0.5h, is neutralized using sodium hydrate aqueous solution, completes preparation process,
Reaction product structure may be expressed as: at this time
Wherein, R1And R2For-CH=CH2, R3、R4For the poly- dimethoxysilane of oligomerization；(a+c): b:x:z=1.58:0.53:
5:5, and a ≠ 0, c ≠ 0, viscosity 90cst.
According to the water repellent effect testing method of embodiment 4, the AATCC22-2005 score 95 after Grafting-coupling Agent；Durability
Test score 90.
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (7)
1. the organo-silicon compound with the structure feature as shown in formula (I):
Wherein,
R1, R2Respectively optionally 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；
R3, R4Respectively optionally from CH3, CH=CH2, oligomerization dimethyl silicone polymer.
2. organo-silicon compound according to claim 1, which is characterized in that the viscosity of the organo-silicon compound is 20-
10000cst。
3. the preparation method of organo-silicon compound of any of claims 1 or 2, which is characterized in that in terms of molfraction, by as follows
Raw material is prepared:
Wherein, the monomer A is methyl cyclosiloxane；Monomer B is tetravinyl tetramethyl-ring tetrasiloxane and/or tetramethyl-ring
Tetrasiloxane, the end-capping reagent include hexamethyldisiloxane, tetramethyl divinyl disiloxane, poly- dimethoxysilane envelope
One of head agent, trim,ethylchlorosilane are a variety of；
Preparation method includes the following steps:
By 5-20 molar part monomer A under catalyst 60-150 DEG C of reaction 0.5-1h, then 5-30 molar part monomer B is added
Enter, reacts in remaining monomer A addition system, the reaction was continued 1-6h after 0.5-1h, end-capping reagent is added and carries out termination process, i.e.,
Obtain the organo-silicon compound.
4. the preparation method of organo-silicon compound according to claim 3, which is characterized in that the methyl cyclosiloxane is
Octamethylcy-clotetrasiloxane and/or hexamethyl cyclotrisiloxane.
5. the preparation method of organo-silicon compound according to claim 3 or 4, which is characterized in that the catalyst is acid
Catalyst or base catalyst.
6. the preparation method of organo-silicon compound according to claim 3 or 4, which is characterized in that the termination process
Time is 0.5-2h.
7. application of the organo-silicon compound described in claim 1 in the material that preparation has waterproofing function.
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