CN114591480A - Polyureido polymer, preparation method thereof and polyurea-based low-temperature-resistant adhesive - Google Patents
Polyureido polymer, preparation method thereof and polyurea-based low-temperature-resistant adhesive Download PDFInfo
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- CN114591480A CN114591480A CN202210306505.5A CN202210306505A CN114591480A CN 114591480 A CN114591480 A CN 114591480A CN 202210306505 A CN202210306505 A CN 202210306505A CN 114591480 A CN114591480 A CN 114591480A
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- 229920002396 Polyurea Polymers 0.000 title claims abstract description 59
- 239000000853 adhesive Substances 0.000 title claims abstract description 40
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 40
- 229920000642 polymer Polymers 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000004985 diamines Chemical class 0.000 claims abstract description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- -1 2-aminopropyl Chemical group 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 12
- FIXBBOOKVFTUMJ-UHFFFAOYSA-N 1-(2-aminopropoxy)propan-2-amine Chemical compound CC(N)COCC(C)N FIXBBOOKVFTUMJ-UHFFFAOYSA-N 0.000 claims description 11
- 229920001451 polypropylene glycol Polymers 0.000 claims description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 229920001155 polypropylene Polymers 0.000 claims description 7
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 abstract 1
- 238000001035 drying Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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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
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
-
- 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
- C09J175/02—Polyureas
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The application provides a polyurea-based polymer, a preparation method thereof and a polyurea-based low-temperature-resistant adhesive. A method of preparing a polyurea-based polymer, comprising: and carrying out polymerization reaction on diisocyanate compounds and diamine by adopting a solution polymerization method to obtain the polyurea-based polymer. Polyurea-based polymers, obtainable using said preparation process. The low-temperature resistant polyurea-based adhesive comprises the polyurea-based polymer. The polyurea-based polymer and the polyurea-based low-temperature-resistant adhesive provided by the application have excellent bonding strength in a low-temperature environment, can realize reversible bonding and have high transparency.
Description
Technical Field
The application relates to the field of high polymer materials, in particular to a polyurea-based polymer, a preparation method thereof and a polyurea-based low-temperature-resistant adhesive.
Background
The low-temperature resistant adhesive is an adhesive which still keeps excellent bonding strength, toughness and fatigue resistance under a low-temperature environment. The device is widely applied to severe working environments such as aerospace, south and north poles, storage equipment of cryogenic liquid and the like. The traditional low temperature resistant adhesives are divided into modified epoxy resin adhesives, modified polyurethane adhesives, organic silicon adhesives and the like. With the increasing new demands brought by the growth of technology, the development of new low temperature resistant adhesives is becoming urgent and necessary.
Disclosure of Invention
The present application is directed to a polyurea-based polymer, a preparation method thereof, and a polyurea-based low temperature resistant adhesive, so as to solve the above problems.
In order to achieve the purpose, the following technical scheme is adopted in the application:
the present application also provides a method of preparing a polyurea-based polymer, comprising:
and carrying out polymerization reaction on diisocyanate compounds and diamine by adopting a solution polymerization method to obtain the polyurea-based polymer.
Preferably, the diisocyanate-based compound includes one or more of isophorone diisocyanate, hexamethylene diisocyanate, 4-dicyclohexylmethane diisocyanate, 2, 4-toluene diisocyanate, diphenylmethane diisocyanate, and p-phenylene diisocyanate.
Preferably, the diamine comprises one or more of polypropylene glycol bis (2-aminopropyl) ether, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol and 1, 3-bis (aminopropyl) tetramethyldisiloxane.
Preferably, the polypropylene glycol bis (2-aminopropyl) ether has a molecular weight of 230, 430, 2000 or 4000 and the O, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol (ED2003) has a molecular weight of 2000.
Preferably, the molar amount of the diisocyanate compound and the diamine is 1: 1.
preferably, the solvent used in the solution polymerization process comprises N-methylpyrrolidone.
Preferably, the temperature of the polymerization reaction is from 50 ℃ to 100 ℃.
The application also provides a polyurea-based polymer prepared by using the preparation method.
The application also provides a polyurea-based low-temperature-resistant adhesive, which comprises the polyurea-based polymer.
Preferably, the polyurea-based low temperature resistant adhesive further comprises a solvent, wherein the solvent comprises one or more of ethanol, N-methyl pyrrolidone and water.
Compared with the prior art, the beneficial effect of this application includes:
the preparation method of the polyurea-based polymer provided by the application obtains the polyurea-based polymer with soft and hard sections through the polymerization reaction of diamine and diisocyanate.
The polyurea-based polymer provided by the application has a bisamide structure with stable conjugation, and is one of the most stable chemical bonds, so that the low-temperature-resistant polyurea-based polymer with excellent performance is obtained; in addition, the low-temperature toughness can be optimized by changing the structure and the chain length of the raw materials.
The polyurea-based low-temperature-resistant adhesive provided by the application still keeps excellent adhesive strength at 60 ℃ below zero by utilizing the performance of the polyurea-based polymer; the base materials bonded by the adhesive can be kept intact without cracking in a liquid nitrogen environment; meanwhile, the adhesive has the advantages of high transparency, easiness in operation, low cost and the like.
Drawings
To more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are required to be used in the embodiments are briefly described below, and it should be understood that the following drawings only illustrate some embodiments of the present application and therefore should not be considered as limiting the scope of the present application.
FIG. 1 is a photograph of a polyurea-based low temperature resistant adhesive obtained in example 1 after bonding to a substrate and subjecting to liquid nitrogen low temperature treatment.
Detailed Description
The terms as used herein:
"prepared from … …" is synonymous with "comprising". The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
The conjunction "consisting of … …" excludes any unspecified elements, steps or components. If used in a claim, the phrase is intended to claim as closed, meaning that it does not contain materials other than those described, except for the conventional impurities associated therewith. When the phrase "consisting of … …" appears in a clause of the subject matter of the claims rather than immediately after the subject matter, it defines only the elements described in the clause; other elements are not excluded from the claims as a whole.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when the range "1 ~ 5" is disclosed, the ranges described should be construed to include the ranges "1 ~ 4", "1 ~ 3", "1 ~ 2 and 4 ~ 5", "1 ~ 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
In these examples, the parts and percentages are by mass unless otherwise indicated.
"part by mass" means a basic unit of measure indicating a mass ratio of a plurality of components, and 1 part may represent any unit mass, for example, 1g or 2.689 g. If we say that the part by mass of the component A is a part by mass and the part by mass of the component B is B part by mass, the ratio of the part by mass of the component A to the part by mass of the component B is a: b. alternatively, the mass of the A component is aK and the mass of the B component is bK (K is an arbitrary number, and represents a multiple factor). It is unmistakable that, unlike the parts by mass, the sum of the parts by mass of all the components is not limited to 100 parts.
"and/or" is used to indicate that one or both of the illustrated conditions may occur, e.g., a and/or B includes (a and B) and (a or B).
The present application provides a method for preparing a polyurea-based polymer, comprising:
and carrying out polymerization reaction on diisocyanate compounds and diamine by adopting a solution polymerization method to obtain the polyurea-based polymer.
In an alternative embodiment, the diisocyanate-based compound includes one or more of isophorone diisocyanate, hexamethylene diisocyanate, 4-dicyclohexylmethane diisocyanate, 2, 4-toluene diisocyanate, diphenylmethane diisocyanate, and p-phenylene diisocyanate.
In an alternative embodiment, the diamine comprises one or more of polypropylene glycol bis (2-aminopropyl) ether, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol and 1, 3-bis (aminopropyl) tetramethyldisiloxane.
In an alternative embodiment, the polypropylene glycol bis (2-aminopropyl) ether has a molecular weight of 230, 430, 2000 or 4000 and the O, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol has a molecular weight of 2000.
I.e., polypropylene glycol bis (2-aminopropyl) ether, satisfies Mw 230g/mol, D230; 430g/mol, D400; 2000g/mol, D2000 and 4000g/mol, D4000. ED2003, 2000g/mol was selected as O, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol.
In an alternative embodiment, the molar amount of the diisocyanate-based compound and the diamine is 1: 1.
in an alternative embodiment, the solvent used in the solution polymerization process comprises N-methylpyrrolidone.
In an alternative embodiment, the temperature of the polymerization reaction is from 50 ℃ to 100 ℃.
The application also relates to a polyurea-based polymer prepared by using the preparation method. The general structural formula is as follows:
Wherein R and R' vary depending on the selected starting materials, R is preferably
R' is preferably
i, m and p are natural numbers and are not 0 at the same time.
The application also provides a polyurea-based low-temperature-resistant adhesive, which comprises the polyurea-based polymer.
In an alternative embodiment, the polyurea-based low temperature resistant adhesive further comprises a solvent comprising one or more of ethanol, N-methyl pyrrolidone, and water.
Embodiments of the present application will be described in detail below with reference to specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present application and should not be construed as limiting the scope of the present application. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
First, the reaction equation for obtaining the polyurea-based polymer provided herein is illustrated as follows:
example 1
This example provides a polyurea-based polymer prepared as follows:
1.11g of isophorone diisocyanate was added to 4.45g N-methyl pyrrolidone to make a 20 wt% solution, which was designated as solution 1. 1.15g of polypropylene glycol bis (2-aminopropyl) ether (Mw 230g/mol) was added to 4.6g N-methylpyrrolidone to make a 20 wt% solution, which was designated as solution 2. Solution 2 was added dropwise to solution 1, and the solution after completion of the dropwise addition was reacted at 50 ℃ overnight. And drying the solvent in a drying oven at 100 ℃ after the reaction is finished to obtain a solid, namely the polyurea-based polymer.
The embodiment also provides a polyurea-based low-temperature-resistant adhesive, and the preparation method comprises the following steps:
and (3) preparing the obtained solid and ethanol into a 10 wt% solution to obtain the polyurea-based low-temperature-resistant adhesive. And dropwise adding the obtained solution onto two substrates, drying at 60 ℃ for two hours, pressing the two substrates together, and continuously drying at 80 ℃ for two hours to obtain a lap joint shear sample.
Example 2
This example provides a polyurea-based polymer prepared as follows:
1.11g of isophorone diisocyanate was added to 4.45g N-methyl pyrrolidone to make a 20 wt% solution, which was designated as solution 1.
1.13g of polypropylene glycol bis (2-aminopropyl) ether (Mw 230g/mol) and 0.20g of ED2003 were added to N-methylpyrrolidone to make a 20 wt% solution, which was designated as solution 2.
Solution 2 was added dropwise to solution 1, and the solution after completion of the dropwise addition was reacted at 50 ℃ overnight. And drying the solvent in a drying oven at 100 ℃ after the reaction is finished to obtain a solid, namely the polyurea-based polymer.
The embodiment also provides a polyurea-based low-temperature-resistant adhesive, and the preparation method comprises the following steps:
and (3) preparing the obtained solid and ethanol into a 10 wt% solution to obtain the polyurea-based low-temperature-resistant adhesive.
The obtained solution is dripped on two base materials, after being dried for two hours at the temperature of 60 ℃, the two base materials are pressed together and dried for two hours at the temperature of 80 ℃, and then a lap joint shearing sample is obtained.
Example 3
This example provides a polyurea-based polymer prepared as follows:
1.31g of 4,4 dicyclohexylmethane diisocyanate was added to 4.45g N-methylpyrrolidone to make a 20 wt% solution, which was designated as solution 1.
1.13g of polypropylene glycol bis (2-aminopropyl) ether (Mw 230g/mol) and 0.20g of ED2003 were added to N-methylpyrrolidone to make a 20 wt% solution, which was designated as solution 2.
Solution 2 was added dropwise to solution 1, and the solution after completion of the dropwise addition was reacted at 50 ℃ overnight. And drying the solvent in a drying oven at 100 ℃ after the reaction is finished to obtain a solid, namely the polyurea-based polymer.
The embodiment also provides a polyurea-based low-temperature-resistant adhesive, and the preparation method comprises the following steps:
and (3) preparing the obtained solid and ethanol into a 10 wt% solution to obtain the polyurea-based low-temperature-resistant adhesive.
The obtained solution is dripped on two base materials, after being dried for two hours at the temperature of 60 ℃, the two base materials are pressed together and dried for two hours at the temperature of 80 ℃, and then a lap joint shearing sample is obtained.
Example 4
This example provides a polyurea-based polymer prepared as follows:
1.11g of isophorone diisocyanate was added to 4.45g N-methyl pyrrolidone to make a 20 wt% solution, which was designated as solution 1.
2.00g of polypropylene glycol bis (2-aminopropyl) ether (Mw ═ 400) was added to N-methylpyrrolidone to make a 20 wt% solution, which was designated as solution 2.
Solution 2 was added dropwise to solution 1, and the solution after completion of the dropwise addition was reacted at 50 ℃ overnight. And drying the solvent in a drying oven at 100 ℃ after the reaction is finished to obtain a solid, namely the polyurea-based polymer.
The embodiment also provides a polyurea-based low-temperature-resistant adhesive, and the preparation method comprises the following steps:
and (3) preparing the obtained solid and ethanol into a 10 wt% solution to obtain the polyurea-based low-temperature-resistant adhesive.
The obtained solution is dripped on two base materials, after being dried for two hours at the temperature of 60 ℃, the two base materials are pressed together and dried for two hours at the temperature of 80 ℃, and then a lap joint shearing sample is obtained.
Comparative example 1
1.11g of isophorone diisocyanate was added to 4.45g N-methyl pyrrolidone to make a 20 wt% solution, which was designated as solution 1. 1.24g of 1, 3-bis (aminopropyl) tetramethyldisiloxane was added to 4.96g N-methylpyrrolidinone to make a 20 wt% solution, noted as solution 2. Solution 2 was added dropwise to solution 1, and the solution after completion of the dropwise addition was reacted at 50 ℃ overnight. After the reaction, the solvent was dried in an oven at 100 ℃ and the resulting solid was made into a 10 wt% solution with ethanol. The obtained solution is dripped on two base materials, after the two base materials are dried for two hours at the temperature of 60 ℃, the two base materials are pressed together, and the drying is continued for two hours at the temperature of 80 ℃, and then a lap joint shearing sample is obtained.
The samples obtained in example 1, example 2 and comparative example 1 were tested for their adhesive strength at room temperature and low temperature, and the results are shown in table 1 below:
TABLE 1 test results
As can be seen from table 1 above, the polyurea-based low temperature resistant adhesive provided by the present application has excellent adhesive strength under low temperature conditions. As shown in FIG. 1, it can be seen from FIG. 1 that the polyurea-based low temperature resistant adhesive provided by the present application can still maintain good adhesion performance after being treated with liquid nitrogen.
The adhesive obtained in comparative example 1 had an adhesive strength of 0 at low temperature because 1, 3-bis (aminopropyl) tetramethyldisiloxane as a diamine had insufficient interaction force between the functional group on the main chain and the surface of the substrate at low temperature and the volume of the polymer shrunk at low temperature, causing a significant decrease in adhesive strength due to interfacial stress.
Finally, it should be noted that: the above embodiments are only used for illustrating the technical solutions of the present application, and not for limiting the same; although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present application.
Moreover, those skilled in the art will appreciate that while some embodiments herein include some features included in other embodiments, rather than other features, combinations of features of different embodiments are meant to be within the scope of the application and form different embodiments. For example, in the claims above, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the application and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art that is already known to a person skilled in the art.
Claims (10)
1. A method of preparing a polyurea-based polymer, comprising:
and carrying out polymerization reaction on diisocyanate compounds and diamine by adopting a solution polymerization method to obtain the polyurea-based polymer.
2. The method according to claim 1, wherein the diisocyanate-based compound comprises one or more of isophorone diisocyanate, hexamethylene diisocyanate, 4-dicyclohexylmethane diisocyanate, 2, 4-toluene diisocyanate, diphenylmethane diisocyanate, and p-phenylene diisocyanate.
3. The method of claim 1, wherein the diamine comprises one or more of polypropylene glycol bis (2-aminopropyl) ether, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol, and 1, 3-bis (aminopropyl) tetramethyldisiloxane.
4. The method according to claim 3, wherein the molecular weight of the polypropylene glycol bis (2-aminopropyl) ether is 230, 430, 2000 or 4000, and the molecular weight of the O, O' -bis (2-aminopropyl) polypropylene glycol-block-polyethylene glycol is 2000.
5. The method according to claim 1, wherein the molar amount of the diisocyanate-based compound and the diamine is 1: 1.
6. the method according to claim 1, wherein the solvent used in the solution polymerization method comprises N-methylpyrrolidone.
7. The method according to any one of claims 1 to 6, wherein the temperature of the polymerization reaction is 50 ℃ to 100 ℃.
8. A polyurea-based polymer produced by the production method according to any one of claims 1 to 7.
9. A polyurea-based low temperature resistant adhesive comprising the polyurea-based polymer of claim 8.
10. The polyurea-based low temperature resistant adhesive of claim 9, further comprising a solvent comprising one or more of ethanol, N-methyl pyrrolidone, and water.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210306505.5A CN114591480A (en) | 2022-03-25 | 2022-03-25 | Polyureido polymer, preparation method thereof and polyurea-based low-temperature-resistant adhesive |
| PCT/CN2022/096691 WO2023178830A1 (en) | 2022-03-25 | 2022-06-01 | Polyurea-based polymer and preparation method therefor and polyurea-based low-temperature-resistant adhesive |
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| CN202210306505.5A CN114591480A (en) | 2022-03-25 | 2022-03-25 | Polyureido polymer, preparation method thereof and polyurea-based low-temperature-resistant adhesive |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023178830A1 (en) * | 2022-03-25 | 2023-09-28 | 香港中文大学（深圳） | Polyurea-based polymer and preparation method therefor and polyurea-based low-temperature-resistant adhesive |
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|---|---|---|---|---|
| EP0380236A2 (en) * | 1989-01-23 | 1990-08-01 | Minnesota Mining And Manufacturing Company | Organopolysiloxane-polyurea block copolymer and method for its production |
| JPH02300227A (en) * | 1989-05-15 | 1990-12-12 | Mitsui Toatsu Chem Inc | Production of polyurea elastomer molding |
| WO2000075210A1 (en) * | 1999-06-07 | 2000-12-14 | 3M Innovative Properties Company | Polyurea-based adhesives, articles therefrom, and methods of their preparation and use |
| CN1604949A (en) * | 2001-12-18 | 2005-04-06 | 3M创新有限公司 | Silicone pressure sensitive adhesives, articles and methods for preparing and using |
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| JP2018012778A (en) * | 2016-07-21 | 2018-01-25 | 荒川化学工業株式会社 | Binder for gravure printing ink and gravure printing ink composition |
| CN108250385A (en) * | 2018-02-09 | 2018-07-06 | 济南大学 | A kind of method that siliceous polyureas mono-dispersion microballoon is prepared by precipitation polymerization high yield |
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| DE10221047A1 (en) * | 2002-05-10 | 2003-11-27 | Degussa | Process for the solvent-free, continuous production of polyureas |
| CN109233204A (en) * | 2018-08-31 | 2019-01-18 | 周晓东 | A kind of preparation method of carbon-based composite wave-absorbing material |
| CN110982403A (en) * | 2019-12-25 | 2020-04-10 | 无锡阿科力科技股份有限公司 | Preparation method of polyurea coating modified by blocked polyetheramine |
| CN114591480A (en) * | 2022-03-25 | 2022-06-07 | 香港中文大学（深圳） | Polyureido polymer, preparation method thereof and polyurea-based low-temperature-resistant adhesive |
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2022
- 2022-03-25 CN CN202210306505.5A patent/CN114591480A/en active Pending
- 2022-06-01 WO PCT/CN2022/096691 patent/WO2023178830A1/en unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023178830A1 (en) * | 2022-03-25 | 2023-09-28 | 香港中文大学（深圳） | Polyurea-based polymer and preparation method therefor and polyurea-based low-temperature-resistant adhesive |
Also Published As
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| WO2023178830A1 (en) | 2023-09-28 |
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