CN115304740A - Dispersion-promoting high-stability polymer and preparation method thereof - Google Patents
Dispersion-promoting high-stability polymer and preparation method thereof Download PDFInfo
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- CN115304740A CN115304740A CN202210290987.XA CN202210290987A CN115304740A CN 115304740 A CN115304740 A CN 115304740A CN 202210290987 A CN202210290987 A CN 202210290987A CN 115304740 A CN115304740 A CN 115304740A
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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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3221—Polyhydroxy compounds hydroxylated esters of carboxylic acids other than higher fatty acids
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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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention relates to C08G18/72, in particular to a dispersion-promoting high-stability polymer and a preparation method thereof. The method comprises the following raw materials: according to mass percentage, 35-50 percent of polyol, 35-55 percent of polyisocyanate, 3-12 percent of epoxy compound with the number of phenyl groups being more than or equal to 2, 1-3 percent of monophenyl and/or aliphatic epoxy compound and 1-3 percent of anchoring agent. The polymer for promoting dispersion and having high stability provided by the invention has the advantages of good emulsification effect, high storage stability and the like.
Description
Technical Field
The invention relates to C08G18/72, in particular to a dispersion-promoting high-stability polymer and a preparation method thereof.
Background
Asphalt, hydrocarbon resin and the like are widely used in the technical fields of coatings, paints, rubbers and the like, but because asphalt, hydrocarbon resin and the like have high viscosity and are difficult to uniformly disperse in application, an emulsifier is frequently added in use.
In patent CN201711483417.8, a radiation-curable water-based fluorine-containing polyurethane acrylate surfactant, a preparation method and applications thereof are disclosed, wherein the surfactant can effectively reduce the surface tension of a system and improve the water resistance of a paint film by using monomethoxypolyethylene glycol and/or polyethylene glycol polypropylene glycol monobutyl ether, perfluoroalkyl alcohol, polyisocyanate-trimethylolpropane adduct and other substances.
Patent CN201711483417.8 discloses a radiation-curable waterborne fluorine-containing polyurethane acrylate surfactant, a preparation method and application thereof, wherein the surfactant is prepared by using short-chain fluoroalcohol, isophorone diisocyanate, organic bismuth catalyst and other substances through a specific synthesis process, and the target product yield is high and the performance is stable.
However, the emulsifier prepared in the prior art has poor stability and general emulsifying effect, and has limited effect when being applied to protective materials such as asphalt, hydrocarbon resin and the like.
Disclosure of Invention
In order to solve the above technical problems, a first aspect of the present invention provides a dispersion-promoting high-stability polymer comprising the following raw materials: according to the mass percentage, 35-50% of polyalcohol, 35-55% of polyisocyanate, 3-12% of epoxy compound with phenyl number more than or equal to 2, 1-3% of monophenyl and/or aliphatic epoxy compound and 1-3% of anchoring agent.
Preferably, the polyol has a functionality of 2 to 3.
Preferably, the polyol has an average molecular weight of 1500 to 3500.
Preferably, the polyol has a hydroxyl value of 45 to 65mgKOH/g.
Preferably, the polyol comprises a polyether polyol and/or a polyester polyol.
Further preferably, the polyol includes polyether polyol and polyester polyol. The mass ratio of the polyether polyol to the polyester polyol is (10-20): (5-12).
Preferably, the polyether polyol has a functionality of 2 and an average molecular weight of 2000.
Preferably, the polyester polyol has a functionality of 2 and an average molecular weight of 2200.
Preferably, the polyisocyanate includes isophorone isocyanate and dicyclohexylmethane diisocyanate. The mass ratio of the isophorone isocyanate to the dicyclohexylmethane diisocyanate is (5-7): (3-5).
Preferably, the epoxy equivalent of the epoxy compound having a phenyl group number of 2 or more is 170 to 200g/eq.
Preferably, the viscosity of the epoxy compound having a phenyl number of 2 or more at 25 ℃ is 8000 to 16000 mPas.
Preferably, the epoxy compound having a phenyl number of 2 or more includes a first epoxy compound and a second epoxy compound. The mass ratio of the first epoxy compound to the second epoxy compound is (5-8): (2-4).
Preferably, the epoxy compound having a phenyl number of 2 or more has an epoxy equivalent of 184 to 195g/eq and a viscosity of 10000 to 16000 mPas at 25 ℃.
Preferably, the epoxy compound having a phenyl number of 2 or more has an epoxy equivalent of 175 to 185g/eq and a viscosity at 25 ℃ of 8000 to 11000mPa · s.
Preferably, the monophenyl epoxy compound is at least one selected from the group consisting of diglycidyl phthalate, diglycidyl terephthalate, diglycidyl isophthalate, diglycidyl tetrahydrophthalate, and diglycidyl methyltetrahydrophthalate.
Further preferably, the monophenyl epoxy compound includes diglycidyl tetrahydrophthalate.
Preferably, the aliphatic epoxy compound is at least one selected from diglycidyl adipate and triglycidyl glycerol ether.
Preferably, the anchoring agent is an alkylamine compound having 8 to 20 carbon atoms.
More preferably, the alkylamine compound having 8 to 20 carbon atoms includes diethylenetriamine and ethylenediamine. The mass ratio of the diethylenetriamine to the ethylenediamine is (1-2): (2-4).
In a second aspect of the present invention, there is provided a method for preparing a dispersion-promoting high-stability polymer, comprising the steps of: heating the polyhydric alcohol in a reactor to 75-85 ℃, melting and stirring uniformly, heating to 115-125 ℃, vacuumizing, cooling to 75-85 ℃, adding polyisocyanate, reacting for 3-5h, adding an anchoring agent, continuing to react for 3-5h, adding a diphenyl epoxy compound, a monophenyl and/or aliphatic epoxy compound and a catalyst, reacting for 1-3h, and discharging to obtain the epoxy resin.
Has the beneficial effects that:
1) The polymer with high dispersion promotion and stability is prepared by the mutual reaction among substances such as polyalcohol, polyisocyanate, epoxy compound with the number of phenyl groups being more than or equal to 2, has the advantages of good emulsification effect, high storage stability and the like, and is particularly suitable for the emulsification and dispersion of hydrocarbon substances such as asphalt, petroleum resin and the like.
2) The invention discovers that the dispersion-promoting high-stability polymer prepared by only adopting polyether polyol is easy to generate foam and slow down the construction progress when being applied to asphalt and petroleum resin. According to the invention, by adopting a form of compounding polyether polyol and polyester polyol, a hydrophobic chain segment in a system is increased, and the foaming performance is reduced, meanwhile, the invention further defines the polyester polyol with the functionality of 2, the average molecular weight of 2200 and the hydroxyl value of 48-54mg/KOH, so that the hydrogen bond strength among carbamate groups is effectively increased, and the reduction of the emulsification effect is avoided, and the particle size of asphalt and petroleum resin is larger when the asphalt and petroleum resin are used.
2) According to the invention, the foaming property is reduced by compounding polyether polyol and polyester polyol, and the emulsifying effect is influenced, so that the penetration is reduced, the isophorone isocyanate and dicyclohexylmethane diisocyanate are compounded, and particularly the mass ratio of the isophorone isocyanate to the dicyclohexylmethane diisocyanate is (5-7): (3-5), the hydrophilic chain segment of the polymer particles with high dispersion promotion stability can be promoted to contact with the outside, so that the decrease of hydrophilicity caused by high content of dicyclohexylmethane diisocyanate is avoided, and the emulsification effect is reduced.
4) The invention further adopts a first epoxy resin with the epoxy equivalent of 184-195g/eq, the viscosity of 10000-16000 mPa.s at 25 ℃ and a second epoxy resin with the epoxy equivalent of 175-185g/eq and the viscosity of 8000-11000 mPa.s at 25 ℃ to compound, the epoxy resin reacts with residual isocyanate groups in the system, and the epoxy resin is coated in a polyurethane chain segment to form a stable crosslinking system, thereby improving the content of evaporation residues, avoiding the epoxy resin from settling and influencing the storage stability.
5) The monophenyl and/or aliphatic epoxy compound, the anchoring agent and other substances in the system are matched with each other, so that the prepared evaporation residue has the advantages of low content, small particle size after emulsification, high softening point and high ductility.
Detailed Description
Examples
Example 1
A dispersion-promoting high-stability polymer comprises the following raw materials: according to the mass percentage, 45.8 percent of polyol, 42 percent of polyisocyanate, 9 percent of epoxy compound with the number of phenyl groups being more than or equal to 2, 1.2 percent of mono-phenyl epoxy compound and 2 percent of anchoring agent.
The polyols include polyether polyols and polyester polyols. The mass ratio of the polyether polyol to the polyester polyol is 15:8.
the polyether polyol has the functionality of 2, the average molecular weight of 2000 and the hydroxyl value of 51-62mg/KOH, is polypropylene glycol, and has the types as follows: PPG2000, available from GmbH International trade, gmbH.
The functionality of the polyester polyol is 2, the average molecular weight is 2200, the hydroxyl value is 48-54mg/KOH, the polyester polyol is polybutylene adipate with the type number: p-2422TL, available from Nissan chemical industries, inc.
The polyisocyanate includes isophorone isocyanate and dicyclohexylmethane diisocyanate. The mass ratio of the isophorone isocyanate to the dicyclohexylmethane diisocyanate is 6:4.
the epoxy compound with the phenyl number being more than or equal to 2 comprises a first epoxy compound and a second epoxy compound. The mass ratio of the first epoxy compound to the second epoxy compound is 7:3.
the first epoxy compound has an epoxy equivalent of 184-195g/eq, a viscosity at 25 ℃ of 10000-16000mPa · s, type: the phoenix WSR618.
The epoxy equivalent of the epoxy compound with the phenyl number being more than or equal to 2 is 175-185g/eq, the viscosity at 25 ℃ is 8000-11000mPa & s, and the type is as follows: phoenix brand 0161.
The epoxy compounds with the phenyl number more than or equal to 2 are all purchased from Wanqing chemical technology Co.
The mono-phenyl epoxy compound comprises diglycidyl tetrahydrophthalate. The mono-phenyl epoxy compound is purchased from Hubei Xingsheng Hengshi science and technology Limited, model: TDE-711.
The anchoring agent comprises diethylenetriamine and ethylenediamine. The mass ratio of the diethylenetriamine to the ethylenediamine is 1.5:2.5.
a preparation method of a dispersion-promoting high-stability polymer comprises the following steps: heating the polyol in a reactor to 82 ℃, melting and stirring uniformly, heating to 120 ℃, vacuumizing, cooling to 82 ℃, adding polyisocyanate, reacting for 4 hours, adding the anchoring agent, continuing to react for 4 hours, adding the diphenyl epoxy compound, the monophenyl and/or aliphatic epoxy compound and the catalyst, reacting for 1.5 hours, and discharging to obtain the polyol.
The catalyst is dibutyltin dilaurate.
Example 2
The specific implementation mode of the polymer with dispersion promotion and high stability is the same as that in example 1, except that the mass ratio of the diethylenetriamine to the ethylenediamine is 2:4.
example 3
The specific implementation mode of the polymer with dispersion promotion and high stability is the same as that of example 1, except that the raw materials comprise 45% of polyol, 44% of polyisocyanate, 7% of epoxy compound with the number of phenyl groups being more than or equal to 2, 1.5% of mono-phenyl epoxy compound and 2.5% of anchoring agent.
Comparative example 1
A dispersion-promoting highly stable polymer, which is the same as in example 1, except that the mass ratio of the first epoxy compound to the second epoxy compound is 7:6.
comparative example 2
A dispersion-promoting, highly stable polymer, as embodied in example 1, is different in that the polyester polyol has a functionality of 2, an average molecular weight of 3000, a hydroxyl number of 35.5 to 39.5mg/KOH, type: p-2430, available from Nisshin chemical industries, inc.
Performance testing
The dispersion-promoting high-stability polymer and asphalt (the asphalt softening point (ring and ball method) prepared in the examples and the comparative examples is 75-90 ℃, the beta-resin content is more than or equal to 12wt%, the toluene insoluble content is 26-32wt%, the quinoline insoluble content is less than or equal to 10wt%, the beta-resin content is more than or equal to 12wt%, the coking value is more than or equal to 30%, and the polymer and asphalt are purchased from Hebei Weixiang chemical engineering Co., ltd.) and water in a mass ratio of 50:3:25, stir and mix well, and perform the following tests.
1. Residue on sieve test after emulsification: the content of residue on the sieve was tested in accordance with SH/T0099.2-1998% = mass after sieve/mass before sieve 100%;
2. and (4) testing the storage stability: the storage stability test was carried out in accordance with SH/T0099.5-1998, the stability being expressed as the degree of stability (difference between the solids content on the upper and lower sides of the emulsion);
3. and (3) testing dispersed particle size: testing by adopting laser particle size analysis;
4. and (3) testing an emulsification effect: the penetration test was carried out according to GB/T4508-2010.
Table 1 results of performance testing
Claims (10)
1. A dispersion-promoting high-stability polymer is characterized by comprising the following raw materials: according to the mass percentage, 35-50% of polyalcohol, 35-55% of polyisocyanate, 3-12% of epoxy compound with phenyl number more than or equal to 2, 1-3% of monophenyl and/or aliphatic epoxy compound and 1-3% of anchoring agent.
2. A dispersion promoting highly stable polymer as claimed in claim 1, wherein said polyol has a functionality of 2 to 3.
3. A dispersion promoting high stability polymer as claimed in claim 1, wherein said polyol has an average molecular weight of 1500 to 3500.
4. A dispersion promoting highly stable polymer as claimed in claim 1, wherein said polyol has a hydroxyl value of 45 to 65mgKOH/g.
5. A dispersion promoting high stability polymer as claimed in claim 1, wherein said polyol comprises polyether polyol and/or polyester polyol.
6. A dispersion-promoting high-stability polymer according to any one of claims 1 to 5, wherein said epoxy compound having a phenyl group number of 2 or more has an epoxy equivalent of 170 to 200g/eq.
7. A dispersion promoting highly stable polymer according to claim 1, wherein said epoxy compound having a phenyl number of not less than 2 has a viscosity of 8000 to 16000 mPas at 25 ℃.
8. A dispersion promoting high stability polymer according to any one of claims 1 to 5, wherein said monophenyl epoxy compound comprises at least one of diglycidyl phthalate, diglycidyl terephthalate, diglycidyl isophthalate, diglycidyl tetrahydrophthalate, diglycidyl methyltetrahydrophthalate.
9. A dispersion promoting high stability polymer according to any one of claims 1 to 5 wherein said anchoring agent is an alkylamine compound having 8 to 20 carbon atoms.
10. A process for preparing a dispersion-promoting high-stability polymer according to claim 1, comprising the steps of: heating the polyhydric alcohol in a reactor to 75-85 ℃, melting and stirring uniformly, heating to 115-125 ℃, vacuumizing, cooling to 75-85 ℃, adding polyisocyanate, reacting for 3-5h, adding an anchoring agent, continuing to react for 3-5h, adding a diphenyl epoxy compound, a monophenyl and/or aliphatic epoxy compound and a catalyst, reacting for 1-3h, and discharging to obtain the epoxy resin.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210290987.XA CN115304740A (en) | 2022-03-23 | 2022-03-23 | Dispersion-promoting high-stability polymer and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210290987.XA CN115304740A (en) | 2022-03-23 | 2022-03-23 | Dispersion-promoting high-stability polymer and preparation method thereof |
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| CN202210290987.XA Withdrawn CN115304740A (en) | 2022-03-23 | 2022-03-23 | Dispersion-promoting high-stability polymer and preparation method thereof |
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| CN (1) | CN115304740A (en) |
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- 2022-03-23 CN CN202210290987.XA patent/CN115304740A/en not_active Withdrawn
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