CN104277225B - Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof - Google Patents
Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof Download PDFInfo
- Publication number
- CN104277225B CN104277225B CN201410525647.6A CN201410525647A CN104277225B CN 104277225 B CN104277225 B CN 104277225B CN 201410525647 A CN201410525647 A CN 201410525647A CN 104277225 B CN104277225 B CN 104277225B
- Authority
- CN
- China
- Prior art keywords
- preparation
- oet
- organic
- organic silicon
- coefficient
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Silicon Polymers (AREA)
Abstract
The invention discloses an organic silicon resin capable of promoting sliding-resistant coefficient, as well as a preparation method and applications thereof. The preparation method comprises the following steps: 1) reacting silane monomer II with an organic silicon monomer III in an organic solvent and water mixed solvent under the action of a catalyst, wherein the catalyst is an ionic liquid; and 2) reacting the materials obtained during reaction with epichlorohydrin for 0.5 hours-2 hours under the temperature condition of 30DEG C-50DEG C, to obtain the organic silicon resin. The organic silicon resin capable of promoting the sliding-resistant coefficient has the significant characteristics of being simple in synthetic technology, mild in reaction conditions, high in yield, and easy for realization of industrialization, and the used catalyst is green, environment-friendly and pollution-free; the obtained organic silicon resin capable of promoting sliding-resistant coefficient can effectively improve the sliding-resistant coefficient property of a mixed material and promote the sliding-resistant performance of a pavement.
Description
Technical field
The present invention relates to a kind of organic siliconresin of lifting coefficient of sliding resistance, its preparation method and its application, belong to road surface dimension
Protector for collar domain.
Background technology
Mist sealing as highway early prevention maintenance most efficient method, in 2004 year " Second China Nationals
Highway science and technology innovates Forum " on, using it as maintenance new technique, promote in the whole nation.The bituminous paving being widely used at present
Preventive maintenance measure has: mist sealing, crack filling, slurry seal, micro-surfacing treating, screening seal coat, hot-mix asphalt mixture are thin
Layer cover etc..Wherein, mist sealing is promoted at home as one of highway early prevention maintenance most efficient method.It
It is by the material of the flow-likes such as emulsified asphalt, modified emulsifying asphalt or asphalt pavement curing agent, be sprayed at Colophonium through spraying machinery
On road surface, and then reach closing road surface hole, stablize discrete aggregate, repair the aging preventive maintenance purpose in road surface.
Organic siliconresin is mainly used in organic silicon insulating varnish, organosilicon coating, silicone plasties and silicone adhesive at present
A few big class such as agent, for the research of road mist sealing seldom, only Wuhan University of Technology Wu Shao roc seminar reports relevant organosilicon
Resin is used for mist sealing, but presence can reduce the defect of road surface coefficient of sliding resistance.And solve organosilicon mist sealing band at present
Carry out coefficient of sliding resistance deficiency problem mainly to be lifted by adding fine sand and rubber powder, not fundamentally from silicone resin material
Start with, traditional organic siliconresin condensation reaction makees catalyst using acid or alkali simultaneously, and it is substantially former that catalyst does not meet Green Chemistry
Then.
Content of the invention
It is an object of the invention to provide a kind of organic siliconresin of lifting coefficient of sliding resistance, its preparation method and its application, with
Overcome organic siliconresin in prior art can reduce the defect of road surface coefficient of sliding resistance for mist sealing presence, and prior art
Middle machine silicones are condensed used catalyst defect not environmentally.
For solving above-mentioned technical problem, the invention of this reality adopts the following technical scheme that
A kind of preparation method of the organic siliconresin of lifting coefficient of sliding resistance, including following steps connected in order:
Step 1) silane monomer ii and organic silicon monomer iii is mixed in the presence of catalyst, in organic solvent and water
React in bonding solvent, wherein, catalyst is ionic liquid, and reaction temperature is 40 DEG C～80 DEG C, and the response time is little for 2 hours～5
When, the mol ratio of silane monomer ii and organic silicon monomer iii is (1:6)～(1:12)；
Step 2) by step 1) material of reaction gained with epoxychloropropane under conditions of temperature is 30 DEG C～50 DEG C, instead
Answer 0.5 hour～2 hours, obtain final product；Wherein, silane monomer ii and the mol ratio of epoxychloropropane are (1:1)～(2:1)；
The structural formula of silane monomer ii is:
In formula, r1、r2And r3It is alkyl, alkoxyl or phenyl；
The structural formula of organic silicon monomer iii is:
In formula, r4For alkyl.
Applicant it has been investigated that, the organic siliconresin of above-mentioned gained carries special silicon atom center and epoxy radicals, significantly
Improve road antiskid performance.
Preferably, the quality consumption of ionic liquid be step 1) reaction system gross mass 0.2%～0.8%.So can protect
The reaction efficiency of card reaction, ensures the antiskid performance of products obtained therefrom simultaneously.
Preferably, ionic-liquid catalyst is n- methylimidazolium hydrogen sulphate sodium, n- N-methyl-2-2-pyrrolidone N sodium bisulfate, 1-
Methyl -3- (3- sulfonic group propyl group) imidazoles potassium acid sulfate, 1- methyl -3- (4- sulfonic group butyl) imidazoles sodium bisulfate, n- (3- sulphur
Acidic group propyl group) pyridine sodium bisulfate or n- (4- sulfonic group butyl) pyridine potassium acid sulfate.So can further improve reaction efficiency.
Preferably, in formula, r1、r2And r3It is ch3, oet, ph, et, butyl or c2h3.Further preferably, in formula, r1
=r2=r3=ch3；r1=r2=ch3、r3=oet；r1=ch3、r2=r3=oet；r1=r2=r3=ph；r1=r2=ph, r3
=oet；r1=ph, r2=r3=oet；r1=r2=r3=et；r1=r2=et, r3=oet；r1=et, r2=r3=oet；r1
=butyl, r2=r3=oet；r1=c2h3、r2=r3=oet.The antiskid performance of products obtained therefrom so can be further ensured that.
Preferably, in formula, r4 is et, butyl or me.So can further ensure the antiskid performance of products obtained therefrom.
Above-mentioned et is ethyl, and ph is phenyl, and butyl is the tert-butyl group, and me is methyl.
Above-mentioned steps (1) are as follows with the concrete reaction equation of (2):
R in formula1、r2And r3With the r in formula1、r2And r3There is identical implication, r in formula4With the r in formula4Tool
There are identical meanings.
Preferably, organic solvent be dimethyl sulfoxide, n, n- dimethylformamide, dioxane, acetonitrile, normal octane, methanol,
Isopropanol, ethanol, toluene, methanol, oxolane, ethyl acetate, normal hexane, hexamethylene, chloroform, dichloromethane or pyridine, mix
In bonding solvent, organic volume and the volume ratio of water are 1/4～4/1.Reaction process so can be further speeded up, improve product yield.
The organosilicon tree of the lifting coefficient of sliding resistance prepared by the preparation method of organic siliconresin of above-mentioned lifting coefficient of sliding resistance
The number-average molecular weight of fat is 3000～6000.
The application of the organic siliconresin of above-mentioned lifting coefficient of sliding resistance, unit square area spread quantity is 0.1～0.5kg, opens
Put traffic time 0.5～2h.
The NM technology of the present invention is prior art.
One distinguishing feature of preparation method that the present invention lifts the organic siliconresin of coefficient of sliding resistance is that synthesis technique is simple, anti-
Answer that mild condition, yield are higher, be easily achieved industrialization, used catalyst green pollution-free；Gained lifts coefficient of sliding resistance
Organic siliconresin can effectively improve coefficient of sliding resistance performance and the lifting pavement skid resistance condition of compound, and properties are equal
Meet the technical specification of Ministry of Communications's formulation.
Specific embodiment
For a better understanding of the present invention, it is further elucidated with present disclosure with reference to embodiment, but the present invention
Content is not limited solely to the following examples.
In following examples, molecular weight is measured by gpc, and mobile phase is chloroform.
The method of the performance detection of organosilicon mist sealing is with reference to " mist sealing construction technology guide ".
Infiltration coefficient is with reference to " standard specification for construction and acceptance of highway asphalt pavement " (People's Republic of China's industry standard, jtgf40-
2004).
Embodiment 1
Trimethylethoxysilane, the positive silicic acid of 15.9g (0.06mol) of 1.2g (0.01mol) is added in there-necked flask
Four formicesters, 0.7gn- methylimidazolium hydrogen sulphate sodium, the ethanol of 20ml and the deionized water of 20ml, are heated to 40 DEG C of reaction 2h and obtain
Intermediate product, is cooled to 30 DEG C, at 30 DEG C to there-necked flask in drip 0.55g (0.006mol) epoxychloropropane, after dripping
Reaction 1.5h obtains the epoxy silicone resin that molecular weight is 3572.Organic siliconresin will be prepared and be uniformly sprayed onto road surface, spray
The amount of spilling is 0.3kg/m2, measure pavement performance after 0.6h, performance is shown in Table one, reference sample is that the bs290 of wacker company is organic
Silicones sample.
Table one, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 4.49 | 4.51 | -- |
| Coefficient of friction/bpn | 70 | 106 | 42 | ≥45 |
| Density/g/cm3 | 2.54 | 2.67 | 2.61 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 77.2 | 75.6 | ≥75 |
| Penetration depth/mm | -- | 5.9 | 4.5 | ≥5 |
| Adhesion strength/mpa | -- | 0.68 | 0.57 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.64 | 0.59 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 27 | 39 | ≤50 |
Embodiment 2
Dimethyldiethoxysilane, the positive silicon of 25.0g (0.12mol) of 1.5g (0.01mol) is added in there-necked flask
The deionized water of sour tetrem fat, the methanol of 0.28gn- N-methyl-2-2-pyrrolidone N sodium bisulfate 30ml and 10ml, is heated to 60 DEG C
Reaction 5h obtains intermediate product, is cooled to 50 DEG C, to the epoxy chloropropionate of Deca 0.74g in there-necked flask (0.008mol) at 50 DEG C
Alkane, after dripping, reaction 0.5h obtains the epoxy silicone resin that molecular weight is 3214.Organic siliconresin will be prepared uniformly spray
It is spread across road surface, fountain height is 0.2kg/m2, measure pavement performance after 1h, performance is shown in Table two, reference sample is wacker company
Bs290 organic siliconresin sample.
Table two, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 4.37 | 4.46 | -- |
| Coefficient of friction/bpn | 70 | 81 | 47 | ≥45 |
| Density/g/cm3 | 2.54 | 2.65 | 2.62 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 75.5 | 73.6 | ≥75 |
| Penetration depth/mm | -- | 6.1 | 5.3 | ≥5 |
| Adhesion strength/mpa | -- | 0.62 | 0.53 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.72 | 0.64 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 31 | 42 | ≤50 |
Embodiment 3
MTES, the positive silicic acid of 25.6g (0.08mol) of 1.8g (0.01mol) is added in there-necked flask
Four fourth fat, 0.13g1- methyl -3- (the 3- sulfonic group propyl group) isopropanol of imidazoles potassium acid sulfate 8ml and the deionized water of 32ml, plus
Heat obtains intermediate product to 80 DEG C of reaction 4h, is cooled to 40 DEG C, to Deca 0.31g in there-necked flask (0.0033mol) at 40 DEG C
Epoxychloropropane.After dripping, reaction 1h obtains the epoxy silicone resin that molecular weight is 3864, will prepare organosilicon tree
Fat is uniformly sprayed onto road surface, and fountain height is 0.4kg/m2, measure pavement performance after 1.5h, performance is shown in Table three, and reference sample is
The bs290 organic siliconresin sample of wacker company.
Table three, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 4.12 | 4.23 | -- |
| Coefficient of friction/bpn | 70 | 112 | 32 | ≥45 |
| Density/g/cm3 | 2.54 | 2.71 | 2.69 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 78.3 | 76.2 | ≥75 |
| Penetration depth/mm | -- | 6.4 | 5.7 | ≥5 |
| Adhesion strength/mpa | -- | 0.67 | 0.58 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.66 | 0.57 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 28 | 36 | ≤50 |
Embodiment 4
Phenyl triethoxysilane, the positive silicic acid of 15.6g (0.075mol) of 2.0g (0.01mol) is added in there-necked flask
Tetrem fat, 0.41gn- (4- sulfonic group butyl) pyridine potassium acid sulfate, the chloroform of 32ml and the deionized water of 8ml, are heated to 50 DEG C
Reaction 3h obtains intermediate product, is cooled to 45 DEG C, to the epoxy chlorine of Deca 0.23g in there-necked flask (0.0025mol) at 45 DEG C
Propane, obtains, after reaction 40min, the epoxy silicone resin that molecular weight is 5721 after dripping.Organic siliconresin will be prepared equal
Even be sprayed onto road surface, after 1h fountain height be 0.5kg/m2, measure pavement performance, performance is shown in Table four, reference sample is that wacker is public
The bs290 organic siliconresin sample of department.
Table four, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 4.33 | 4.46 | -- |
| Coefficient of friction/bpn | 70 | 137 | 21 | ≥45 |
| Density/g/cm3 | 2.54 | 2.78 | 2.74 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 79.6 | 78.1 | ≥75 |
| Penetration depth/mm | -- | 5.8 | 5.1 | ≥5 |
| Adhesion strength/mpa | -- | 0.61 | 0.60 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.58 | 0.52 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 29 | 30 | ≤50 |
Embodiment 5
Ethyl triethoxysilane, the positive silicic acid of 14.6g (0.07mol) of 1.9g (0.01mol) is added in there-necked flask
Tetrem fat, 0.36g1- methyl -3- (4- sulfonic group butyl) imidazoles sodium bisulfate, the acetonitrile of 25ml and the deionized water of 15ml, plus
Heat obtains intermediate product to 45 DEG C of reaction 4.5h, is warmed up to 50 DEG C, to Deca 0.18g in there-necked flask (0.002mol) at 50 DEG C
Epoxychloropropane, after dripping reaction 100min after obtain the epoxy silicone resin that molecular weight is 5562.To prepare
Machine silicones are uniformly sprayed onto road surface, and fountain height is 0.1kg/m2, measure pavement performance after 1.2h, performance is shown in Table five, with reference to examination
Sample is the bs290 organic siliconresin sample of wacker company.
Table five, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 6.02 | 6.23 | -- |
| Coefficient of friction/bpn | 70 | 145 | 64 | ≥45 |
| Density/g/cm3 | 2.54 | 2.53 | 2.52 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 75.3 | 73.8 | ≥75 |
| Penetration depth/mm | -- | 6.3 | 5.7 | ≥5 |
| Adhesion strength/mpa | -- | 0.54 | 0.52 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.69 | 0.71 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 47 | 52 | ≤50 |
Embodiment 6
VTES, the positive silicon of 17.7g (0.085mol) of 1.9g (0.01mol) is added in there-necked flask
Sour tetrem fat, 0.2gn- (3- sulfonic group propyl group) pyridine sodium bisulfate, the oxolane of 15ml and the deionized water of 25ml, heating
Obtain intermediate product to 45 DEG C of reaction 3.5h, to the epoxy chloropropionate of Deca 0.1g in there-necked flask (0.00105mol) at 45 DEG C
Alkane, obtains, after reaction 70min, the epoxy silicone resin that molecular weight is 4658 after dripping.Organic siliconresin will be prepared uniform
It is sprayed onto road surface, fountain height is 0.4kg/m2, measure pavement performance after 0.8h, performance is shown in Table six, reference sample is that wacker is public
The bs290 organic siliconresin sample of department.
Table six, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 3.98 | 4.23 | -- |
| Coefficient of friction/bpn | 70 | 76 | 32 | ≥45 |
| Density/g/cm3 | 2.54 | 2.71 | 2.69 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 78.4 | 76.2 | ≥75 |
| Penetration depth/mm | -- | 5.7 | 5.7 | ≥5 |
| Adhesion strength/mpa | -- | 0.65 | 0.58 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.59 | 0.57 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 35.5 | 36 | ≤50 |
Embodiment 7
Triphenyl Ethoxysilane, the positive silicic acid of 21.9g (0.085mol) of 3.0g (0.01mol) is added in there-necked flask
Tetrem fat, 0.44gn- methylimidazolium hydrogen sulphate sodium, the pyridine of 10ml and the deionized water of 30ml, are heated to 75 DEG C of reaction 2.5h
Obtain intermediate product, cool to 35 DEG C, to the epoxychloropropane of Deca 0.11g in there-necked flask (0.00115mol) at 35 DEG C,
Obtain, after reaction 110min, the epoxy silicone resin that molecular weight is 4133 after dripping.Organic siliconresin will be prepared uniformly spray
It is spread across road surface, fountain height is 0.3kg/m2, measure pavement performance after 0.8h, performance is shown in Table seven, reference sample is wacker company
Bs290 organic siliconresin sample.
Table seven, the pavement performance of organic resin
| Experimental project | Prevailing roadway | Organic siliconresin | wacker | Technical requirements |
| Voidage/% | 4.85 | 4.44 | 4.51 | -- |
| Coefficient of friction/bpn | 70 | 142 | 42 | ≥45 |
| Density/g/cm3 | 2.54 | 2.63 | 2.61 | -- |
| Freeze-thaw split strength ratio/% | 52.6 | 76.1 | 75.6 | ≥75 |
| Penetration depth/mm | -- | 5.0 | 4.5 | ≥5 |
| Adhesion strength/mpa | -- | 0.58 | 0.57 | ≥0.5 |
| Construction depth/mm | 0.78 | 0.60 | 0.59 | ≥0.55 |
| Infiltration coefficient ml/min | -- | 38 | 39 | ≤50 |
Claims (9)
1. a kind of preparation method of the organic siliconresin of lifting coefficient of sliding resistance it is characterised in that: include following step connected in order
Rapid:
Step 1) silane monomer ii and organic silicon monomer iii is molten in the presence of catalyst, in the mixing of organic solvent and water
React in agent, wherein, catalyst is ionic liquid, and reaction temperature is 40 DEG C～80 DEG C, and the response time is 2 hours～5 hours, silicon
The mol ratio of alkane monomer ii and organic silicon monomer iii is (1:6)～(1:12)；
Step 2) by step 1) material of reaction gained with epoxychloropropane under conditions of temperature is 30 DEG C～50 DEG C, reaction
0.5 hour～2 hours, obtain final product；Wherein, silane monomer ii and the mol ratio of epoxychloropropane are (1:1)～(2:1)；
The structural formula of silane monomer ii is:
In formula, r1、r2And r3It is alkyl or phenyl；
The structural formula of organic silicon monomer iii is:
In formula, r4For alkyl.
2. preparation method as claimed in claim 1 it is characterised in that: the quality consumption of ionic liquid be step 1) reaction system
The 0.2%～0.8% of gross mass.
3. preparation method as claimed in claim 1 or 2 it is characterised in that: ionic-liquid catalyst be n- Methylimidazole. sulphuric acid
Hydrogen sodium, n- N-methyl-2-2-pyrrolidone N sodium bisulfate, 1- methyl -3- (3- sulfonic group propyl group) imidazoles potassium acid sulfate, 1- methyl -3-
(4- sulfonic group butyl) imidazoles sodium bisulfate, n- (3- sulfonic group propyl group) pyridine sodium bisulfate or n- (4- sulfonic group butyl) pyridine
Potassium acid sulfate.
4. preparation method as claimed in claim 1 or 2 it is characterised in that: in formula, r1、r2And r3It is ch3、oet、ph、
Et, butyl or c2h3.
5. preparation method as claimed in claim 4 it is characterised in that: in formula, r1=r2=r3=ch3；r1=r2=ch3、r3
=oet；r1=ch3、r2=r3=oet；r1=r2=r3=ph；r1=r2=ph, r3=oet；r1=ph, r2=r3=oet；r1
=r2=r3=et；r1=r2=et, r3=oet；r1=et, r2=r3=oet；r1=butyl, r2=r3=oet；r1=c2h3、
r2=r3=oet.
6. preparation method as claimed in claim 1 or 2 it is characterised in that: in formula, r4 be et, butyl or me.
7. preparation method as claimed in claim 1 or 2 it is characterised in that: organic solvent be dimethyl sulfoxide, n, n- dimethyl
Methanamide, dioxane, acetonitrile, normal octane, methanol, isopropanol, ethanol, toluene, methanol, oxolane, ethyl acetate, just oneself
Alkane, hexamethylene, chloroform, dichloromethane or pyridine, in mixed solvent, organic volume and the volume ratio of water are 1/4～4/1.
8. the lifting prepared by the preparation method of organic siliconresin lifting coefficient of sliding resistance described in claim 1-7 any one resists
The organic siliconresin of sliding coefficient it is characterised in that: its number-average molecular weight is 3000～6000.
9. described in claim 8 lifting coefficient of sliding resistance organic siliconresin application it is characterised in that: for road mist envelope
Layer, unit square area spread quantity is 0.1～0.5kg, open to traffic time 0.5～2h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410525647.6A CN104277225B (en) | 2014-10-08 | 2014-10-08 | Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410525647.6A CN104277225B (en) | 2014-10-08 | 2014-10-08 | Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104277225A CN104277225A (en) | 2015-01-14 |
| CN104277225B true CN104277225B (en) | 2017-01-25 |
Family
ID=52252607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410525647.6A Active CN104277225B (en) | 2014-10-08 | 2014-10-08 | Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104277225B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968363A (en) * | 2016-05-17 | 2016-09-28 | 江苏中路新材料科技发展有限公司 | Organic silicon resin capable of improving water damage resistance of roads as well as preparation method and application of organic silicon resin |
| CN109762514B (en) * | 2019-01-30 | 2021-09-17 | 广东思密达科技有限公司 | Preparation method of environment-friendly silicone sealant |
| CN114672246A (en) * | 2022-04-29 | 2022-06-28 | 东风商用车有限公司 | Friction-increasing layer solution for preventing coated rivet from being distorted, and preparation, coating and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354013A (en) * | 1980-01-22 | 1982-10-12 | Toshiba Silicone Co., Ltd. | Process for preparing epoxy-modified silicone resins |
| US5115069A (en) * | 1989-03-29 | 1992-05-19 | Toshiba Silicone Co., Ltd. | Glycidoxy group-containing organosilicon compound |
| CN1683467A (en) * | 2005-03-03 | 2005-10-19 | 武汉理工大学 | Water-proof and oil-repelling agent of colorless organic silicon resin for asphalt road surface |
| CN101555352A (en) * | 2009-04-22 | 2009-10-14 | 武汉理工大学 | A new maintenance material of pavement crack, preparation and application thereof |
| CN102153315A (en) * | 2010-12-27 | 2011-08-17 | 湖北环宇化工有限公司 | Preventive maintenance material for asphalt pavement |
| CN102690418A (en) * | 2012-05-25 | 2012-09-26 | 上海富朗化工科技发展有限公司 | Organosilicon modified epoxy resin and preparation method thereof |
| JP2014047207A (en) * | 2012-09-04 | 2014-03-17 | Shin Etsu Chem Co Ltd | Novel organic silicon compound and its manufacturing method |
-
2014
- 2014-10-08 CN CN201410525647.6A patent/CN104277225B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354013A (en) * | 1980-01-22 | 1982-10-12 | Toshiba Silicone Co., Ltd. | Process for preparing epoxy-modified silicone resins |
| US5115069A (en) * | 1989-03-29 | 1992-05-19 | Toshiba Silicone Co., Ltd. | Glycidoxy group-containing organosilicon compound |
| CN1683467A (en) * | 2005-03-03 | 2005-10-19 | 武汉理工大学 | Water-proof and oil-repelling agent of colorless organic silicon resin for asphalt road surface |
| CN101555352A (en) * | 2009-04-22 | 2009-10-14 | 武汉理工大学 | A new maintenance material of pavement crack, preparation and application thereof |
| CN102153315A (en) * | 2010-12-27 | 2011-08-17 | 湖北环宇化工有限公司 | Preventive maintenance material for asphalt pavement |
| CN102690418A (en) * | 2012-05-25 | 2012-09-26 | 上海富朗化工科技发展有限公司 | Organosilicon modified epoxy resin and preparation method thereof |
| JP2014047207A (en) * | 2012-09-04 | 2014-03-17 | Shin Etsu Chem Co Ltd | Novel organic silicon compound and its manufacturing method |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104277225A (en) | 2015-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103946299B (en) | Rubber composition and pneumatic tire | |
| KR100376362B1 (en) | Epoxy polysiloxane polymer coating composition and method for making same | |
| CN104277225B (en) | Organic silicon resin capable of promoting sliding-resistant coefficient, as well as preparation method and applications thereof | |
| CN105623503B (en) | A kind of silicon rubber hydrophobic coating for insulator and preparation method thereof | |
| CN103917590B (en) | Rubber combination and studless tire | |
| CN108070269A (en) | A kind of epoxy-modified emulsified asphalt mist containing sand sealing material and its preparation method and application | |
| CN106519913B (en) | Improve the method for epoxy resin primary coat compound cementability and the epoxy resin primary coat compound of high cementitiousness | |
| CN110903661B (en) | U-pave special modified asphalt and preparation method and application method thereof | |
| CN109824903B (en) | High-refractive-index boron-containing organic silicon tackifier and preparation method thereof | |
| CN103755964B (en) | Polysiloxane tackifying resin and preparation method thereof | |
| CN104529262A (en) | Resin-grouted water-permeable pavement material and preparation method thereof | |
| CN104530967A (en) | Reactive organosilicon waterproofing agent as well as preparation method and application thereof | |
| CN107674636A (en) | A kind of preparation of the organosilicon sealant of α aminosilane coupling agent modifyings | |
| CN102757733B (en) | Preparation method of tackifying processing agent | |
| CN105542169A (en) | Preparation method for alkoxy functionalized polysiloxane | |
| CN106810573A (en) | One kind is combined silane coupled adhesion promoters and preparation method thereof | |
| CN114163884A (en) | Waterproof anti-slip coating special for outer wall and preparation method and application thereof | |
| CN110128984A (en) | Red green dry-hang glue of one kind and preparation method thereof | |
| CN103601392B (en) | Long-chain alkyl polyamine Series of Asphalt antistripping agent and preparation method thereof | |
| CN106519238A (en) | Synthetic method for macromolecule silane coupling agent | |
| CN103880022A (en) | Inorganic polymer material, method for forming same, and inorganic polymer coating film formed thereby | |
| CN105238226B (en) | Non-solvent epoxy Shamian Island non-skip terrace | |
| JP4937597B2 (en) | Method for painting decorative surface and decorative laminate | |
| CN104559758A (en) | Bottom coating liquid for silane modified polyether sealant and preparation method thereof | |
| CN107641466A (en) | A kind of organosilicon solvent-free dip varnish and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP02 | Change in the address of a patent holder | ||
| CP02 | Change in the address of a patent holder |
Address after: 210008 No. 12, Beijing West Road, Gulou District, Nanjing City, Jiangsu Province Co-patentee after: Nanjing Bote Building Materials Co., Ltd. Patentee after: Jiangsu Subute New Materials Co., Ltd. Address before: 211103 No. 118 Liquan Road, Jiangning District, Nanjing City, Jiangsu Province Co-patentee before: Nanjing Bote Building Materials Co., Ltd. Patentee before: Jiangsu Subute New Materials Co., Ltd. |