CN105330864A - Organic silicon compound and preparation method and application thereof - Google Patents
Organic silicon compound and preparation method and application thereof Download PDFInfo
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- CN105330864A CN105330864A CN201510718569.6A CN201510718569A CN105330864A CN 105330864 A CN105330864 A CN 105330864A CN 201510718569 A CN201510718569 A CN 201510718569A CN 105330864 A CN105330864 A CN 105330864A
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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
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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
-
- 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
Abstract
The invention relates to an organic silicon compound and a preparation method and application thereof. The organic silicon compound has the structural general formula as the formula (I) (please see the formula in the specification), wherein R1 and R2 are respectively selected from -CH=CH2, and-H, a:b:c:x:z is equal to (0-7):(0-3):(0-3):(1-5):(1-5), and a and c cannot be zero at the same time. According to the organic silicon compound, active sites are arranged in the molecular middle of chemical compounds in a concentrated mode, the water-repellency effect can be better played compared with the prior art, meanwhile, and the organic silicon compound has excellent compatibility with base materials. When the organic silicon compound is actually used for preparing materials with the water-repellent function, and good durability and good water repellency can be acquired.
Description
Technical field
The present invention relates to organic synthesis field, particularly relate to a kind of silicoorganic compound and its preparation method and application.
Background technology
The basic structural unit of silicoorganic compound is made up of silicon-oxygen chain link, and side chain is then connected by the various organic group of Siliciumatom and other.Therefore, both containing " organic group " in the structure of organosilicon product, again containing " inorganic structure ", this special composition and molecular structure make it integrate the function of organic characteristic and inorganics, and its intermolecular reactive force is much more weak than hydrocarbon polymer, therefore low than the hydrocarbon viscosity of same molecular weight, surface tension is weak, surface energy is little, and film forming ability is strong.This low surface tension and low surface energy make it have certain hydrophobic performance, and its price is relatively cheap, thus become the study hotspot refusing water field gradually.
Prior art just openly adopts containing hydrogen silicone oil to be used for the method for waterproof mildew-resistant of the waterproof of building materials, ancient building waterproof, protection against the tide, mildew-resistant protection and paper.But report the industrial goods that the silicoorganic compound used mostly are ripe at present, because this body structure still has some limitations (functional group is few, surface energy is low), poor with the consistency of base material (such as textiles, material of construction etc.), cause water repellency, weather resistance not ideal enough.
Summary of the invention
Based on this, be necessary to provide a kind of silicoorganic compound.
There are the silicoorganic compound such as formula constitutional features (I) Suo Shi:
Wherein, R
1, R
2optional from-CH=CH respectively
2,-H;
A:b:c:x:z=(0-7): (0-3): (0-3): (1-5): (1-5), and be 0 when a with c is different.
Wherein in an embodiment,
(1) c=0, R
1optional from-CH=CH
2,-H;
A:b:x:z=(0.5-7): (0.5-3): (1-5): (1-5); Or,
(2) b=c=0, R
1optional from-CH=CH
2,-H;
A:x:z=(0.5-3): (1.5-5): (1.5-5); Or,
(3) R
1, R
2optional from-CH=CH respectively
2,-H;
(a+c): b:x:z=(0.5-3): (0.5-2): (2.5-5): (2.5-5), and a ≠ 0, c ≠ 0.
Wherein in an embodiment, the viscosity of these silicoorganic compound is 20-10000cst (25 DEG C).
The present invention also provides the preparation method of described silicoorganic compound, in molfraction, is prepared from by following raw material:
Wherein, described monomer A is methyl cyclosiloxane; Monomers B is tetravinyl tetramethyl-ring tetrasiloxane and/or tetramethyl-ring tetrasiloxane,
Preparation method comprises the steps:
30-70 molar part monomer A and 5-30 molar part monomers B are pre-mixed, under catalyst, 60-150 DEG C of reaction 1-3h, adds remaining monomer A, continues reaction 1-6h, adds end-capping reagent and carry out termination process, obtain described silicoorganic compound; Or,
By 5-30 molar part monomers B 60-150 DEG C of reaction 1-3h under catalyst, then 100 molar part monomer A are added in system, continue reaction 1-6h, add end-capping reagent and carry out termination process, obtain described silicoorganic compound; Or,
By 60-150 DEG C of reaction 0.5-1h under 5-20 molar part monomer A catalyst, again 5-30 molar part monomers B is added, after reaction 0.5-1h, remaining monomer A is added in system, continue reaction 1-6h, add end-capping reagent and carry out termination process, obtain described silicoorganic compound.
Wherein in an embodiment, described methyl cyclosiloxane is octamethylcyclotetrasiloxane and/or hexamethyl cyclotrisiloxane.
Wherein in an embodiment, described end-capping reagent comprise in hexamethyldisiloxane, tetramethyl divinyl disiloxane, poly-dimethoxysilane closure agent, trimethylchlorosilane one or more.
Wherein in an embodiment, described catalyzer is acid catalyst or alkaline catalysts.
Wherein in an embodiment, the time of described termination process is 0.5-2h.
The present invention also provides described silicoorganic compound preparing the application had in the material of waterproofing function.
Principle of the present invention and advantage as follows:
The experimental studies results discovery that the present invention is comprehensively a large amount of, the quality key of the waterproofing function of silicoorganic compound depends on the distribution situation of avtive spot in compound structure, and prior art is when preparing silicoorganic compound, synchronously add each polymerization single polymerization monomer to be polymerized, in the compound prepared, avtive spot is often in irregular distribution, be cross-linked thus and prepare waterproofing function material, its polydimethylsiloxane group activity with water-proof function is subject to larger restriction, freely can not unfold, thus affect the performance of material waterproofing function.
Based on this discovery, the present invention provides the monomer of polydimethylsiloxane group section (monomer A) by conservative control and provides the add-on of monomer (monomers B) and the order of avtive spot (be preferably vinyl and hydrogen base), prepare the silicoorganic compound that a series of avtive spot is positioned at compound medium position, there is the compound activity site concentrated setting of this structure in the middle part of silicone molecule, two ends are PolydimethylsiloxaneChain Chain sections freely, after active group generation is crosslinked, free segment still can freely be unfolded, play and refuse water effect preferably, also have excellent in consistency that is base material simultaneously, when being applied to preparation and there is waterproofing function material, good weather resistance and water repellency can be obtained.
Compared with prior art, the present invention has following beneficial effect:
Silicoorganic compound of the present invention, by the middle part of avtive spot concentrated setting in compound molecule, can comparatively prior art better play and refuse water effect, also have excellent in consistency that is base material simultaneously, when being applied to preparation and there is waterproofing function material, good weather resistance and water repellency can be obtained.
The preparation method of silicoorganic compound of the present invention, step is simple, is easy to control, and is convenient to industrial applications.
Embodiment
Below in conjunction with specific embodiment, silicoorganic compound of the present invention and its preparation method and application are described in further detail.
In embodiments of the present invention:
A1: octamethylcyclotetrasiloxane, 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 reaction 1h under 1 molar part concentrated sulfuric acid catalyst catalysis, again 70 molar part A1 are added in system, continue reaction 3h, add 2 molar part hexamethyldisiloxane reaction termination process 0.5h, use aqueous sodium hydroxide solution neutralization, complete preparation process, now in reaction product, functional group concentrates in the middle part of the segment of molecule, and structure can be expressed as:
Wherein, R
1for-H, R
3for CH
3, R
4for CH
3; A:b:x:z=1:1:1.1:1.1, its viscosity is 50cst.
Comparative example 1
100 molar part A1 are mixed with 30 molar part B2,120 DEG C of reaction 4h under 1 molar part concentrated sulfuric acid catalyst catalysis, add hexamethyldisiloxane reaction termination process 0.5h, use aqueous sodium hydroxide solution neutralization, complete preparation process, reaction product functional group random dispersion is in molecule.
Performance comparison:
By 100 parts of embodiment 1 products therefroms with etc. the vinyltrimethoxy silane of stoichiometric ratio mix, at Karstedt catalyzer (consumption is 0.01 part) 80 DEG C reaction 24h, obtain the silicone oil of By Grafting-coupling Agent, be labeled as water repllents 1.
By 100 parts of comparative example 1 products therefroms with etc. the vinyltrimethoxy silane of stoichiometric ratio mix, at Karstedt catalyzer (consumption is 0.01 part) 80 degrees Celsius reaction 24h, obtain the silicone oil of By Grafting-coupling Agent, be labeled as water repllents 2.
(1) water measure of merit is refused
Dissolve with chloroform, be prepared into the water repllents active liquid of massfraction 1%, process cotton, two leachings two are pricked, and dry 2min for 120 DEG C, 160 DEG C of sizing 1min, after placing 4h, and test water repellency (AATCC22-2005).Embodiment 1 must be divided into 90 points, and comparative example 1 must be divided into 70 points, significant difference.
After processing concrete in the same way, embodiment 1 water after immersion 24h does not infiltrate, and refuse water Be very effective, and comparative example 1 infiltrates after immersion 24h.
(2) durability test
With 3% washing powder concentration, refuse the cotton after water treatment in 45 DEG C of washing 15min post-flush totally by above-mentioned, dry, water effect is refused in test afterwards in triplicate, and embodiment 1 must be divided into 85 points, and comparative example 1 must be divided into 65.
Embodiment 2
By 20 molar part B2,60 DEG C of reaction 1h under 1 molar part concentrated sulfuric acid catalyst catalysis, again 100 molar part A1 are added in system, continue reaction 3h, add 2 molar part tetramethyl divinyl disiloxane reaction termination process 0.5h, use aqueous sodium hydroxide solution neutralizes, complete preparation process, now in reaction product, functional group concentrates in the middle part of the segment of molecule, and structure can be expressed as:
Wherein, R
1for-H, R
3for CH=CH
2, R
4for CH=CH
2; A:x:z=2:5:5, its viscosity is 500cst.
Water effect testing method is refused, AATCC22-2005 score 95 after By Grafting-coupling Agent according to embodiment 1; Durability test score 90.
Embodiment 3
By 5 molar part A1,150 DEG C of reaction 1h under 0.01 molar part concentrated sulfuric acid catalyst catalysis, again 20 molar part B2 are added in system, continue reaction 1h, add 95 molar part A1 after adding catalyzer 0.5 molar part and continue reaction 2h, the poly-dimethoxysilane closure agent (MDM) adding 0.5 molar part list end-blocking processes 0.5h, use aqueous sodium hydroxide solution neutralizes, and complete preparation process, now reaction product structure can be expressed as:
Wherein, R
1and R
2for-H; (a+c): b:x:z=2.1:0.53:5:5, and a ≠ 0, c ≠ 0, its viscosity is 800cst.
Water effect testing method is refused, AATCC22-2005 score 95 after By Grafting-coupling Agent according to embodiment 1; Durability test score 85.
Embodiment 4
30 molar part A2 and 20 molar part B1 are pre-mixed, 60 DEG C of reaction 3h under 10 molar part Amberlyst-15 catalysts, again 70 molar part A2 are added in system, continue reaction 6h, add 0.2 molar part hexamethyldisiloxane reaction termination process 0.5h, removed by filtration catalyzer, a small amount of unreacted monomer of removed under reduced pressure, complete preparation process, now reaction product structure can be expressed as:
Wherein, R
1for-CH=CH
2, R
3for CH
3, R
4for CH
3; A:b:x:z=3:2:3.5:3.5, its viscosity is 600, and after By Grafting-coupling Agent, functional group concentrates in the middle part of the segment of molecule.
By 100 parts of embodiment 4 products therefroms with etc. the vinyltrimethoxy silane of stoichiometric ratio mix, at Karstedt catalyzer (consumption is 0.01 part) 80 degrees Celsius reaction 24h, obtain the silicone oil of By Grafting-coupling Agent, AATCC22-2005 score 90; Durability test score 85.
Embodiment 5
By 20 molar part B1,60 DEG C of reaction 1h under 1 molar part potassium hydroxide aqueous solution catalyst, again 100 molar part A2 are added in system, continue reaction 3h, add 0.01 molar part tetramethyl divinyl disiloxane reaction termination process 0.5h, use aqueous sulfuric acid neutralizes, complete preparation process, now reaction product structure can be expressed as:
Wherein, R
1for-CH=CH
2, R
3for-CH=CH
2, R
4for-CH=CH
2; A:x:z=1:1.9:1.9, its viscosity is 10000cst, and functional group concentrates in the middle part of the segment of molecule.
Water effect testing method is refused, AATCC22-2005 score 90 after By Grafting-coupling Agent according to embodiment 1; Durability test score 85.
Embodiment 6
By 20 molar part A2 at 5 molar part SO
4 2-/ ZrO
2(method for preparing catalyst is see " based on SO for catalyzer
4 2-/ ZrO
2hybrid catalyst design and biofuel synthesis in application ", Northeast Normal University's Ph D dissertation, 2011, Li Wei) the lower 100 DEG C of reaction 1h of catalysis, then 20 molar part B1 are added in system, add catalyzer 0.5 molar part and continue reaction 1h, add 80 molar part A2 and continue reaction 2h, the poly-dimethoxysilane closure agent (MDM) adding 1 molar part list end-blocking processes 0.5h, filtration catalizer, complete preparation process, now reaction product structure can be expressed as:
Wherein, R
1and R
2for-CH=CH
2, R
3, R
4for oligomerization polydimethylsiloxane; (a+c): b:x:z=1.3:1:2.7:2.7, and a ≠ 0, c ≠ 0, its viscosity is 300cst.
Water effect testing method is refused, AATCC22-2005 score 95 after By Grafting-coupling Agent according to embodiment 4; Durability test score 85.
Embodiment 7
30 molar part A2 and 5 molar part B2 are pre-mixed, 120 DEG C of reaction 1h under 1 molar part concentrated sulfuric acid catalyst catalysis, again 70 molar part A2 are added in system, continue reaction 3h, add 0.7 molar part hexamethyldisiloxane reaction termination process 0.5h, use aqueous sodium hydroxide solution neutralization, complete preparation process, now in reaction product, functional group concentrates in the middle part of the segment of molecule, and structure can be expressed as:
Wherein, R
1for-H, R
3for CH
3, R
4for CH
3; A:b:x:z=0.71:3:5:5, its viscosity is 300cst.
Water effect testing method is refused, AATCC22-2005 score 85 after By Grafting-coupling Agent according to embodiment 1; Durability test score 80.
Embodiment 8
By 5 molar part B1,60 DEG C of reaction 1h under 1 molar part sodium hydroxide catalyst catalysis, again 100 molar part A2 are added in system, continue reaction 3h, add 0.1 molar part tetramethyl divinyl disiloxane reaction termination process 0.5h, use aqueous sulfuric acid neutralizes, complete preparation process, now in reaction product, functional group concentrates in the middle part of the segment of molecule, and structure can be expressed as:
Wherein, R
1for-CH=CH
2, R
3for-CH=CH
2, R
4for-CH=CH
2; A:x:z=0.67:5:5, its viscosity is 9000cst.
Water effect testing method is refused, AATCC22-2005 score 90 after By Grafting-coupling Agent according to embodiment 4; Durability test score 85.
Embodiment 9
By 20 molar part A2,150 DEG C of reaction 1h under 0.01 molar part concentrated sulfuric acid catalyst catalysis, again 5 molar part B1 are added in system, do not add catalyzer 0.5 molar part and continue reaction 1h, add 80 molar part A2 and continue reaction 2h, the poly-dimethoxysilane closure agent (MDM) adding 2 molar part list end-blockings processes 0.5h, use aqueous sodium hydroxide solution neutralizes, and complete preparation process, now reaction product structure can be expressed as:
Wherein, R
1and R
2for-CH=CH
2, R
3, R
4for oligomerization gathers dimethoxysilane; (a+c): b:x:z=1.58:0.53:5:5, and a ≠ 0, c ≠ 0, its viscosity is 90cst.
Water effect testing method is refused, AATCC22-2005 score 95 after By Grafting-coupling Agent according to embodiment 4; Durability test score 90.
Each technical characteristic of the above embodiment can combine arbitrarily, for making description succinct, the all possible combination of each technical characteristic in above-described embodiment is not all described, but, as long as the combination of these technical characteristics does not exist contradiction, be all considered to be the scope that this specification sheets is recorded.
The above embodiment only have expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be construed as limiting the scope of the patent.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (9)
1. there are the silicoorganic compound such as formula constitutional features (I) Suo Shi:
Wherein, R
1, R
2optional from-CH=CH respectively
2,-H;
A:b:c:x:z=(0-7): (0-3): (0-3): (1-5): (1-5), and be 0 when a with c is different.
2. silicoorganic compound according to claim 1, is characterized in that,
(1) c=0, R
1optional from-CH=CH
2,-H;
A:b:x:z=(0.5-7): (0.5-3): (1-5): (1-5); Or,
(2) b=c=0, R
1optional from-CH=CH
2,-H;
A:x:z=(0.5-3): (1.5-5): (1.5-5); Or,
(3) R
1, R
2optional from-CH=CH respectively
2,-H;
(a+c): b:x:z=(0.5-3): (0.5-2): (2.5-5): (2.5-5), and a ≠ 0, c ≠ 0.
3. silicoorganic compound according to claim 1 and 2, is characterized in that, the viscosity of these silicoorganic compound is 20-10000cst.
4. the preparation method of the silicoorganic compound described in any one of claim 1-3, is characterized in that, in molfraction, is prepared from by following raw material:
Wherein, described monomer A is methyl cyclosiloxane; Monomers B is tetravinyl tetramethyl-ring tetrasiloxane and/or tetramethyl-ring tetrasiloxane,
Preparation method comprises the steps:
30-70 molar part monomer A and 5-30 molar part monomers B are pre-mixed, under catalyst, 60-150 DEG C of reaction 1-3h, adds remaining monomer A, continues reaction 1-6h, adds end-capping reagent and carry out termination process, obtain described silicoorganic compound; Or,
By 5-30 molar part monomers B 60-150 DEG C of reaction 1-3h under catalyst, then 100 molar part monomer A are added in system, continue reaction 1-6h, add end-capping reagent and carry out termination process, obtain described silicoorganic compound; Or,
By 60-150 DEG C of reaction 0.5-1h under 5-20 molar part monomer A catalyst, again 5-30 molar part monomers B is added, after reaction 0.5-1h, remaining monomer A is added in system, continue reaction 1-6h, add end-capping reagent and carry out termination process, obtain described silicoorganic compound.
5. the preparation method of silicoorganic compound according to claim 4, is characterized in that, described methyl cyclosiloxane is octamethylcyclotetrasiloxane and/or hexamethyl cyclotrisiloxane.
6. the preparation method of the silicoorganic compound according to claim 4 or 5, it is characterized in that, described end-capping reagent comprise in hexamethyldisiloxane, tetramethyl divinyl disiloxane, poly-dimethoxysilane closure agent, trimethylchlorosilane one or more.
7. the preparation method of the silicoorganic compound according to claim 4 or 5, is characterized in that, described catalyzer is acid catalyst or alkaline catalysts.
8. the preparation method of the silicoorganic compound according to claim 4 or 5, is characterized in that, the time of described termination process is 0.5-2h.
9. the silicoorganic compound described in claim 1 or 2 are preparing the application had in the material of waterproofing function.
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| CN110591099A (en) * | 2019-08-05 | 2019-12-20 | 广州中国科学院工业技术研究院 | Polysiloxane block polymer and application thereof |
| CN110760066A (en) * | 2018-07-26 | 2020-02-07 | 东莞市博君来胶粘材料科技有限公司 | Base oil of low-oil-separation heat-conducting silicone grease and synthesis process thereof |
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