CN105733490B - A kind of cement concrete pavement gap-filling glue of moisturecuring self-crosslinking - Google Patents
A kind of cement concrete pavement gap-filling glue of moisturecuring self-crosslinking Download PDFInfo
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- CN105733490B CN105733490B CN201610175923.XA CN201610175923A CN105733490B CN 105733490 B CN105733490 B CN 105733490B CN 201610175923 A CN201610175923 A CN 201610175923A CN 105733490 B CN105733490 B CN 105733490B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C11/00—Details of pavings
- E01C11/02—Arrangement or construction of joints; Methods of making joints; Packing for joints
- E01C11/04—Arrangement or construction of joints; Methods of making joints; Packing for joints for cement concrete paving
- E01C11/10—Packing of plastic or elastic materials, e.g. wood, resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
Abstract
The present invention relates to a kind of Joint Sealants for Cemcent Concrete Pavement of moisturecuring self-crosslinking, isocyanate group crosslinking curing is substituted with silicone hydroxyl, which is one-component, and when use only needs to extrude, component in the gap-filling glue will be reacted with the water in air, crosslinking curing；The gap-filling glue is the new polyurethane performed polymer synthesized by polyether polyol, isocyanates, terminal hydroxy group organosilicon, the dissaving polymer of methoxy group, catalyst, crosslinking agent and pigment etc.；While the use problem of present invention crosslinking agent MOCA afraid of water and carcinogenic when overcoming traditional gap-filling glue construction operation, the characteristics such as good caking property, anti-embeddability and resistance to ag(e)ing are still maintained, it is a kind of long shelf-life, compare environmentally friendly, can solve very well because the uncertain factor such as weather influences the new polyurethane gap-filling glue of cement pavement joint filling operation progress.
Description
The present invention relates to cement pavement pointing field, more particularly to a kind of organosilicon containing hyperbranched polyamine -ester
Modified polyurethane gap-filling glue, and the preparation method of the organic silicon modified polyurethane gap-filling glue.
Background technology
At present the most common cement pavement gap-filling glue in China be based on polyurethane sealant, it with its excellent watertight,
Air-tightness, high resiliency, caking property and durable, weatherability etc., can be for a long time through Tensile, compression and vibration, and cohesive force is strong, can be through
Expanded with heat and contract with cold by seam crossing and stretch repeatedly, compress the advantages that facilitating without destroyed and construction method, be widely used in water
Cement concrete road surface, is improved the quality of cement concrete pavement, while service life of road surface is effectively extended.
Polyurethane sealant is polymerized by isocyanates and polyether polyol, usually there is one-component and two-component two
Kind.Contain the highly polar group such as-NCO and-OH in polyurethane filling material molecular structure, reaction can form tough bullet after curing
Property tack coat.Polyurethane sealant has the characteristics that oil resistant, wear-resisting, vibration resistance, endurance, high-low temperature resistant at the same time.It is existing to have
Method of the machine silicon modified polyurethane gap-filling glue by introducing silicone segments into molecule, the introducing of silicon oxygen bond solve traditional
The shortcomings of polyurethane filling material weatherability is poor, and under long-term sunlight, easy dusting turns yellow, service life shortening.
But either traditional polyurethane sealant or it is organic-silicon-modified after polyurethane sealant be all to depend on-NCO
Crosslinking, and-NCO is easy to and active hydrogen reaction, in the presence of having water, this isocyanate terminated polyurethane prepolymer is known from experience curing and is released
Carbon dioxide is released, glue-line is blistered, this has seriously affected the service life of polyurethane filling material, especially influences it
Construction under misty rain weather condition.In addition, isocyanate terminated polyurethane sealant uses the double o-chloranilines of methine（MOCA）
As crosslinking agent, it is to have carcinogenesis to human body which, which is identified,.
At present, in the world on the one hand some developed countries are directed to studying a kind of new crosslinking agent, it is intended to substitute MOCA；
On the other hand it is also dedicated to study a kind of waterproof polyurethane sealant.Thus it is necessary to research and develop a kind of new substitution tradition
Isocyanate terminated crosslinking curing pointing, while again be not required MOCA as crosslinking agent.
The presentation of dissaving polymer space structure is spherical, has more regular structure, substantial amounts of active group is contained in end
The features such as group, its highly branched structure impart dissaving polymer high reaction activity, low viscosity, therefore can be by super
The functional end-group of branched polymer is modified so as to obtain the modified ultra-branching polymer of differential responses demand.Hyperbranched poly at present
Compound all embodies huge application value in fields such as coating, adhesive, biomaterial, drug carriers.
The content of the invention
In order to solve the problems, such as that the isocyanate terminated base polyurethane prepolymer for use as of tradition is afraid of water, the present invention provides a kind of moisturecuring certainly
Crosslinking, and there is good high-low temperature resistant, caking property, ageing-resistant, and have good anti-embeddability and elastomeric water
Cement concrete pavement joint sealing material.
Present invention also offers the preparation method containing hyperbranched organic silicon modified polyurethane gap-filling glue.
The cement concrete pavement pointing, the preparation process of its base polyurethane prepolymer for use as are as follows：
Polyether polyol is added in the reaction vessel of dry cleansing.Under the vacuum of -0.092MP or so, open
Circulating condensing water, opens stirring, control temperature at 90 DEG C or so, dehydration until on condenser it is substantially anhydrous out when, be cooled to 50
℃.Under nitrogen protection, MDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature prevents that implode is anti-at 50 DEG C or so
The generation answered, is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure reaction 2h.Then to body
The hydroxyl-terminated injecting two methyl siloxane that molecular weight is 1000 is added dropwise in system, after reacting 3h, closes nitrogen intake valve, opens vacuum system
System, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression dehydration 2-3h, is then shut off true
Empty set is united, and opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
Existing industrial production polyurethane sealant is generally adopted by prepolymer method, with isocyanates and polyether polyols
Alcohol reacts to obtain isocyanate-terminated base polyurethane prepolymer for use as, but-NCO can so cause glue-line easily with active hydrogen reaction
Blistering, shortens the service life of gap-filling glue, this has resulted in the difficulty in the construction of misty rain weather.It is contemplated that use Si-OH
The base polyurethane prepolymer for use as of end-blocking, under conditions of methoxyl group makees crosslinking agent, adds catalyst, just can be with so in the presence of having water
Water reacts, and crosslinking curing, thoroughly solves the problems, such as that its is afraid of water.
The base polyurethane prepolymer for use as blocked first by adjusting the dosage synthesizing isocyanate base of polyether polyol and MDI, then
The poly- of silicone hydroxyl end-blocking is synthesized by the content of-NCO in measure system and the dosage of the hydroxyl-terminated injecting two methyl siloxane added
Urethane performed polymer, this base polyurethane prepolymer for use as are the Si-OH by end with occurring under the collective effect of crosslinking agent and catalyst
Crosslinking curing.
Using some performances of dissaving polymer, as dissolubility is good, viscosity is low, and end carries substantial amounts of active group
It can be used for modification and obtain the group that we want.Building-up process is simple, it is not necessary to and separating-purifying, production cost is low, therefore this
Invention is wanted to synthesize crosslinking agent of the dissaving polymer as this product that a large amount of methoxyl groups are contained in a kind of end.
The preparation of dissaving polymer：
（1）Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth is connected with 100 respectively
DEG C thermometer and dropping funel, to three-necked flask among be passed through nitrogen, open magnetic stirring apparatus so that diethanol amine and methanol fill
Divide miscible.Then methyl acrylate is added in dropping funel, is slowly added drop-wise among flask, after being added dropwise, water-bath
40 DEG C, insulation reaction 6h are heated to, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes
Methanol is removed, obtains AB2Type monomer, reaction equation are as follows：
（2）Trimethylolpropane is added in above-mentioned system and is passed through nitrogen as catalyst as core molecule, p-methyl benzenesulfonic acid
Gas, stirs to solid under the atmosphere of nitrogen protection and is all completely dissolved, be then warming up to 85 DEG C, insulation reaction 24h, reactional equation
Formula is as follows：
The hydroxyl value that synthesized dissaving polymer is determined by using acetic acid pyridine circumfluence method is 396-566mgKOH/
g.From the point of view of the measure of hydroxyl value, substantial amounts of hydroxyl is contained in synthesized dissaving polymer end.
Add 3- isocyanate group propyl trimethoxy silicanes into above-mentioned reaction system, maintain the temperature at 85 DEG C or so, protect
The dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in temperature reaction 6h, vacuum distillation, after reaction structural formula
It is as follows
The hydroxyl value that synthesized dissaving polymer is determined by using acetic acid pyridine circumfluence method is 9-31mgKOH/g.
From the point of view of the measure of hydroxyl value, the synthesized substantial amounts of hydroxyl in dissaving polymer end has disappeared, and illustrates our modification ratio
It is relatively successful.
The performance test of the Joint Sealants for Cemcent Concrete Pavement of the present invention
Obtained product is extruded, in atmosphere after full cross-linked curing, is tested for the property, its surface drying time in 7h,
Needle penetration is 3.8mm, elastic restoration ratio 78%, tensile strength 0.66MPa, adhesion strength 0.48MPa, and elongation at break is
432%, 80 DEG C of * 168h of high temperature do not trickle, and -40 DEG C of * 168h of low temperature are not broken.Cement pavement because the four seasons alternately change, the temperature difference compared with
Greatly, cement sheeting can produce the cold drawn phenomenon of hot pressing, therefore carry out the cold drawn experiment of hot pressing to the gap-filling glue at -30 DEG C and 20 DEG C,
Experiment proves that the pointing not only can be in 100% time progress, and displacement remains to reach 50% requirement over numerous cycles,
And adhesion strength can reach 0.33MPa, reach national standard.
The beneficial effects of the invention are as follows：
This of the present invention is overcoming traditional gap-filling glue afraid of water containing hyperbranched organic silicon modified polyurethane pointing
On the premise of, can directly it be reacted with water, moisturecuring self-crosslinking, and the product is single-component product, when use is directly extruded to water
It is easy to use in mud seam gap, and to environment non-hazardous, safety and environmental protection.The pointing is still kept on this basis
The characteristic such as good resistant of high or low temperature, anti-embeddability and caking property, is a kind of service life length, cost low new joint filling material
Material, has good market prospects.
Embodiment
That specific implementation method of the present invention is more stated in detail below, it is therefore intended that illustrate the present invention design and
Feature, it is not intended to limit the scope of the present invention.Any equivalent change or modification in accordance with the spirit of the invention,
It should be covered by the protection scope of the present invention.
The cement pavement pointing of the present invention is described in more detail below, its object is to illustrate the present invention
Design and feature, it is not intended to limit the scope of the present invention.The equivalent change that all Spirit Essences according to the present invention are made
Change or modify, should be covered by the protection scope of the present invention.
Embodiment one
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）6.7g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 3g（2）The dissaving polymer of middle synthesis, and the following filler of 35g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Embodiment two
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）2.2g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 3g（2）The dissaving polymer of middle synthesis, and the following filler of 35g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Embodiment three
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）1.0g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 3g（2）The dissaving polymer of middle synthesis, and the following filler of 35g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Example IV
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）2.2g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 5g（2）The dissaving polymer of middle synthesis, and the following filler of 35g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Embodiment five
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）2.2g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 2g（2）The dissaving polymer of middle synthesis, and the following filler of 35g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Embodiment six
（1）Precise 16g（0.15mol）Diethanol amine, 13g（0.15mol）Methyl acrylate and 75ml methanol, first
Diethanol amine and methanol are added in the three-necked flask with magnetic stirring apparatus, flask mouth be connected with respectively 100 DEG C of thermometers and
Dropping funel, is passed through nitrogen to three-necked flask, opens magnetic stirring apparatus so that diethanol amine and methanol are fully miscible in the middle.And
Methyl acrylate is added in dropping funel afterwards, is slowly added drop-wise among flask, after being added dropwise, heating water bath is warming up to
40 DEG C, insulation reaction 6h, then the product that reaction obtains is transferred among Rotary Evaporators, vacuum distillation removes methanol, obtains
To AB2Type monomer.
（2）6.7g is added in above-mentioned system（0.05mol）As core molecule, add mass fraction is trimethylolpropane
0.5% p-methyl benzenesulfonic acid is passed through nitrogen as catalyst, under the atmosphere of nitrogen protection stirring be all completely dissolved to solid, and
After be warming up to 85 DEG C, insulation reaction 24h, into reaction system plus 60g（0.3mol）3- isocyanate group propyl trimethoxy silicon
Alkane, at 85 DEG C, insulation reaction 6h, the dissaving polymer that a large amount of methoxyl groups are contained in end has just been prepared in vacuum distillation.
（3）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（4）Take 3g（2）The dissaving polymer of middle synthesis, and the following filler of 25g altogether, talcum powder, lightweight carbonic acid
Calcium, aerosil, pigment, plasticizer, catalyst are added to what reaction terminated（3）In, at a certain temperature, high-speed stirred
Uniformly, nitrogen intake valve is then shut off, opens vacuum system, maintains temperature at 85 DEG C（±2℃）It is left with vacuum -0.092MP
Under conditions of the right side, decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（5）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Comparison example
（1）It is 2000 by 15g molecular weight, hydroxyl value is 54-57mgOH/g polyoxypropyleneglycols, and 10g molecular weight is 3000,
Hydroxyl value is added in the reaction vessel of dry cleansing for 56-58mgOH/g polypropylene oxide triols.In the true of -0.092MP or so
Under reciprocal of duty cycle, circulating condensing water is opened, opens stirring, control temperature is at 90 DEG C or so, and dehydration is until substantially anhydrous on condenser come out
When, it is cooled to 50 DEG C.Under nitrogen protection, 6.9gMDI is slowly added dropwise into above-mentioned system, stringent controlling reaction temperature is at 50 DEG C
Left and right prevents the generation that implode is reacted, and is added dropwise in 30min, is then to slowly warm up to 85 DEG C（±2℃）, polymerization under atmospheric pressure is anti-
Answer 2h.Then the hydroxyl-terminated injecting two methyl siloxane that 17.5g molecular weight is 1000 is added dropwise into system, after reacting 3h, closes nitrogen
Gas intake valve, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so, decompression
2-3h is dehydrated, is then shut off vacuum system, opens nitrogen intake valve, system is recovered normal pressure.It is cooled to 70 DEG C.
（2）Take the following filler of 35g altogether, talcum powder, precipitated calcium carbonate, aerosil, pigment, plasticizer, urge
Agent and methyltrimethoxysilane are added to what reaction terminated（1）In, at a certain temperature, high-speed stirred is uniform, Ran Houguan
Nitrogen intake valve is closed, opens vacuum system, maintains temperature at 85 DEG C（±2℃）With under conditions of vacuum -0.092MP or so,
Decompression dehydration 2-3h, then recovers normal pressure, closes vacuum system, is packed with extruder discharging.
（3）In use, opening packaging, directly filler extrusion is filled into the gap of cement concrete pavement, is filled out
Stitch the water in the end group and air in material self-crosslinking can cure at normal temperatures.
Performance detection
The polyurethane filling material of examples detailed above is tested for the property, it is as shown in the table for its result：
| Elongation at break % | Tensile strength MPa | Adhesion strength MPa | Needle penetration mm | Hot pressing-cold drawn circulation MPa | 80 DEG C of high temperature resistant | Low temperature resistant -40 DEG C | |
| Embodiment one | 415 | 1.03 | 0.6 | 2.6 | 0.54 | Do not trickle | It is not broken |
| Embodiment two | 468 | 0.88 | 0.58 | 3.4 | 0.53 | Do not trickle | It is not broken |
| Embodiment three | 422 | 0.79 | 0.45 | 4.2 | 0.42 | Do not trickle | It is not broken |
| Example IV | 433 | 0.81 | 0.62 | 3.0 | 0.45 | Do not trickle | It is not broken |
| Embodiment five | 437 | 0.76 | 0.55 | 3.7 | 0.42 | Do not trickle | It is not broken |
| Embodiment six | 483 | 0.83 | 0.54 | 4.4 | 0.38 | Do not trickle | It is not broken |
| Comparison example | 432 | 0.66 | 0.48 | 3.8 | 0.43 | Do not trickle | It is not broken |
Note：Above testing standard uses JT/T 589-2004.
It can be seen that tensile strength, elongation at break, the bonding of product after addition dissaving polymer by data in table
The performances such as intensity are improved, and institute's test performance result is above requirements of the national standard, and based on the increase of various fillers, its
Cost solves the shortcomings that conventional urethane gap-filling glue is afraid of water also below market product, and this product need to only squeeze when in use
Go out to expose the product in air, it is reacted with the water in air, crosslinking curing is easy to use.Illustrate present invention conjunction
Into containing hyperbranched organic silicon modified polyurethane gap-filling glue be it is a kind of preferably novel environment friendly pointing.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention and from the limit of embodiment
System, it is other it is any without departing from the present invention Spirit Essences with made under principle change, modification, combine, replacement, simplification should be
Equivalence replacement mode, is included within protection scope of the present invention.
Claims (9)
1. a kind of Joint Sealants for Cemcent Concrete Pavement of moisturecuring self-crosslinking, it is characterized in that one-component, the product is more by polyethers
First alcohol and isocyanate polymeric obtain base polyurethane prepolymer for use as, then react with hydroxyl-terminated injecting two methyl siloxane to obtain silicone hydroxyl end-blocking
Base polyurethane prepolymer for use as, then contain with end a large amount of methoxyl groups dissaving polymer be crosslinked under the conditions of having existing for water it is solid
Change, the end of the dissaving polymer is methoxyl group；
The hydroxy number of isocyanate group and polyether polyol ratio is 2.2:1；
Isocyanate group number ratio after hydroxyl-terminated injecting two methyl siloxane terminal hydroxyl and preliminary polymerization is 1.8:1；
The weight ratio for holding the dissaving polymer of silicone hydroxyl base polyurethane prepolymer for use as and methoxy group is 20:1.
2. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that end silicone hydroxyl polyurethane prepolymer
The weight ratio of body, crosslinking agent and filler is 20:1:7, filler is talcum powder, precipitated calcium carbonate, aerosil, pigment, increasing
Mould one or more of agent, catalyst.
3. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that crosslinking agent is synthesized first
The dissaving polymer of epoxide end-blocking.
4. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that the hydroxyl value of polyether polyol is
54-58mgKOH/g。
5. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that the dissaving polymer of synthesis
Its end group is methoxyl group.
6. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that dissaving polymer is to pass through
What following methods were prepared：
16g diethanol amine, 13g methyl acrylates are reacted to obtain AB2Type monomer, adds 2.2g trimethylolpropanes as core point
Son, adds the p-methyl benzenesulfonic acid that mass fraction is 0.5% and obtains Hyperbranched Polymer with Terminal Hydroxyl as catalyst reaction, then uses 60g
3- isocyanate group propyl trimethoxy silicane is modified Hyperbranched Polymer with Terminal Hydroxyl to obtain end methoxyl group hyperbranched poly
Compound.
7. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that water is directly extruded during use
In the gap of road face, silicone hydroxyl blocks in product base polyurethane prepolymer for use as and methoxyl group can be very under the conditions of having existing for water
Fast crosslinking curing, the process is simple and easy to operate, and Environmental Safety.
8. Joint Sealants for Cemcent Concrete Pavement according to claim 6, it is characterised in that trimethylolpropane is different with 3-
Cyanic acid ester group propyl trimethoxy silicane molar ratio is 1:3、1:9 or 1:21.
9. Joint Sealants for Cemcent Concrete Pavement according to claim 1, it is characterised in that dissaving polymer is as friendship
Join agent in use, the 2%-5% for the base polyurethane prepolymer for use as that dosage blocks for silicone hydroxyl.
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| EP3601399A1 (en) * | 2017-03-29 | 2020-02-05 | Sika Technology AG | Water-based composition having improved mechanical properties |
| CN107200849B (en) * | 2017-05-17 | 2020-06-09 | 江苏超力建材科技有限公司 | Water-based interface agent for cement highway joint and preparation method and application thereof |
| CN108384024A (en) * | 2018-03-19 | 2018-08-10 | 济南大学 | A kind of preparation improving self-adhesive asphalt waterproof coiled material adhesive property hyperbranched resin |
| CN111218876B (en) * | 2018-11-27 | 2021-07-16 | 长春市市政工程设计研究院 | Cement concrete pavement wet assembling process with three-dimensional embedding and extruding joint |
| CN110257001A (en) * | 2019-07-15 | 2019-09-20 | 江苏盛世海新材料科技有限公司 | A kind of flexibility joint trimming agent |
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| CN103408924A (en) * | 2013-07-10 | 2013-11-27 | 万铜岭 | Pavement joint sealing material |
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| JP2011111481A (en) * | 2009-11-25 | 2011-06-09 | Asahi Kasei Homes Co | One-pack type moisture curable sealing material composition and method of improving antibacterial properties and mildew resistance of coating film topcoated on outer wall joint by using the same |
| CN102604368A (en) * | 2012-03-02 | 2012-07-25 | 济南大学 | NCO replaced crosslinking cured joint filling material for concrete pavement |
| CN202766943U (en) * | 2012-09-24 | 2013-03-06 | 河南万里路桥集团有限公司 | Filling and sealing structure for cement concrete pavement slit |
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