CN110698965B - Epoxy resin modified polyurethane hyperbranched prepolymer and cement interface agent - Google Patents
Epoxy resin modified polyurethane hyperbranched prepolymer and cement interface agent Download PDFInfo
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- CN110698965B CN110698965B CN201911144270.9A CN201911144270A CN110698965B CN 110698965 B CN110698965 B CN 110698965B CN 201911144270 A CN201911144270 A CN 201911144270A CN 110698965 B CN110698965 B CN 110698965B
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- cement
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 57
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 51
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 51
- 239000004814 polyurethane Substances 0.000 title claims abstract description 43
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 43
- 239000004568 cement Substances 0.000 title claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
- 239000003292 glue Substances 0.000 claims abstract description 13
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 239000012948 isocyanate Substances 0.000 claims abstract description 11
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 8
- 229920000768 polyamine Polymers 0.000 claims abstract description 8
- 239000004970 Chain extender Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 238000007789 sealing Methods 0.000 claims abstract description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 5
- -1 N-diethylformamide Chemical compound 0.000 claims description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 4
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 4
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 claims description 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 3
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 238000002360 preparation method Methods 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 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
- 239000008096 xylene Substances 0.000 claims description 3
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 2
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- 229940035437 1,3-propanediol Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 230000007547 defect Effects 0.000 abstract description 4
- 229920005601 base polymer Polymers 0.000 abstract description 3
- 238000009736 wetting Methods 0.000 abstract description 2
- 229920005749 polyurethane resin Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 18
- 238000002156 mixing Methods 0.000 description 8
- 239000004567 concrete Substances 0.000 description 6
- 238000010276 construction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 229960001124 trientine Drugs 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 3
- 239000002344 surface layer Substances 0.000 description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000006253 efflorescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011150 reinforced concrete Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/58—Epoxy resins
-
- 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
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides a cement interface agent, which is prepared from the following components: the epoxy resin modified polyurethane hyperbranched prepolymer is prepared by heating and reacting epoxy resin, polyamine and a reaction solvent A to obtain an amino polymer; and the chain extender, the isocyanate monomer and the reaction solvent B are sequentially added into the reaction kettle and heated for reaction to obtain the polyurethane resin. The cement interface agent disclosed by the invention adopts the epoxy resin modified polyurethane hyperbranched prepolymer as a film-forming base polymer, so that the defect of poor water resistance of the traditional polyurethane interface agent is overcome; in addition, the interface agent provided by the invention has excellent cement wetting and bonding performances, and the prepared cement interface agent for the ballastless track caulking glue can be applied to the glue for the high-speed rail ballastless track caulking and can be widely applied to interface glue treatment for assembly type building sealing.
Description
Technical Field
The invention belongs to the field of high polymer materials, and particularly relates to an epoxy resin modified polyurethane hyperbranched prepolymer and a cement interface agent.
Background
After the high-speed development of more than ten years, the high-speed rail in China is built into a global maximum high-speed rail operation network, has the most advanced technology and experience of a high-speed rail complete system, and is reputed by the high-speed rail in China at home and abroad. The track construction is one of the most important basic constructions of high-speed rails, and railway tracks can be divided into ballasted tracks and ballastless tracks. Compared with the traditional ballast track, the ballastless track has the advantages of good smoothness, good stability, good durability and the like, and the ballastless track construction mode is mainly adopted for high-speed rails in China. In order to avoid the influence of outdoor thermal expansion and cold contraction, the ballastless track needs to be cut into segments, and after cutting, caulking glue needs to be filled in gaps so as to prevent reinforced concrete in the ballastless track from being corroded by rainwater, damaged by freezing and thawing and the like, thus prolonging the service life of track engineering and improving traffic safety.
Considering the influence of the surface characteristics of concrete and dust generated during cutting construction on the caulking glue bonding effect, the technical standard QCR 601-2017 railway ballastless track caulking material of China railway general company stipulates that an interface agent needs to be matched when the caulking glue is used. The interface agent essentially acts as a bridge between the concrete surface layer and the caulk surface layer, so the interface agent has the basic characteristics of strongly bonding the concrete surface layer and the caulk. In addition, the interface agent coating at the interface can effectively prevent the adverse effect of the concrete efflorescence phenomenon on the caulking glue adhesion. According to different film-forming resins, the currently commonly used concrete interface agents are mainly divided into two types, namely epoxy resin and polyurethane. Most epoxy resin interface agents are of a two-component type and have the characteristics of excellent adhesive property, good water resistance and the like, but the epoxy resin interface agents have the defect of high requirements on construction processes and equipment. The polyurethane interface agent is usually in a single-component form, and mainly takes isocyanate-terminated prepolymer as a film forming material, and solvent is added to improve the construction performance. However, the single-component polyurethane has the defects of poor water-resistant adhesion and the like.
The Chinese patent with application number of CN201410071904.3 discloses an epoxy modified polyurethane primer and a preparation method thereof, which mainly illustrate the compound mixing modification of two-component epoxy resin and mutual two-component polyurethane, and the curing mechanism is that the two-component epoxy resin and two-component polyurethane prepolymer react with respective corresponding curing agents to form a dual-curing body with an interpenetrating network structure.
Different from the prior art, the invention mainly explains that the hyperbranched oligomer obtained by the reaction of epoxy resin and polyamine participates in the polyurethane reaction and enters the main chain segment of the polyurethane prepolymer to achieve the goal of chemically modifying polyurethane, thereby forming a uniform solidified body. Aiming at the characteristics of poor water resistance of a single-component polyurethane interface agent and excellent water resistance of epoxy resin, the invention discloses an epoxy modified polyurethane hyperbranched compound as a base polymer and takes the epoxy modified polyurethane hyperbranched compound as a main component of the interface agent so as to prepare a cement interface agent for ballastless track caulking compound.
Disclosure of Invention
Based on the above, one of the objectives of the present invention is to provide a novel cement interface agent, wherein the hyperbranched polymer cured product introduced by the cement interface agent has a high crosslinking density and thus has good water resistance.
The technical scheme for achieving the purpose is as follows.
The cement interface agent is prepared from the following components in parts by weight:
the epoxy resin modified polyurethane hyperbranched prepolymer is prepared by the following method:
1) adding 10-20 parts by weight of epoxy resin, 5-10 parts by weight of polyamine and 20-40 parts by weight of reaction solvent A into a reaction kettle, and heating for reaction to obtain an amino polymer;
2) and sequentially adding 80-100 parts by weight of the amino polymer, 5-10 parts by weight of the chain extender, 10-20 parts by weight of the isocyanate monomer and 50-80 parts by weight of the reaction solvent B into a reaction kettle, and reacting at normal temperature to obtain the self-made epoxy resin modified polyurethane hyperbranched prepolymer.
In one embodiment, in step 1), the reaction conditions are: heating to 100 ℃ and 120 ℃, and stirring for 120min and 180 min.
In one embodiment, the epoxy resin is at least one of E-51 having an epoxy value of 0.48 to 0.54(100g/g), E44 having an epoxy value of 0.41 to 0.47(100 g/g).
In one embodiment, the polyamine is one or more of diethylenetriamine, triethylenetetramine and tetraethylenepentamine. Difunctional isocyanates can be reacted with the appropriate polyamines to form branched structures, and difunctional isocyanates can be reacted with polyamines to form chain structures.
In one embodiment, the reaction solvent a is at least one of N, N-dimethylformamide, N-diethylformamide, N-dimethylacetamide, N-diethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, and N-ethylpyrrolidone.
In one embodiment, the chain extender is one or more of 1, 4-butanediol, 1, 2-ethylene glycol, 1, 3-propylene glycol and 1, 6-hexanediol.
In one embodiment, the isocyanate monomer is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, and naphthalene diisocyanate.
In one embodiment, the reaction solvent B is one or more of butyl acetate, dimethyl carbonate, dichlorobutane, isophorone and No. 120 solvent oil.
In one embodiment, the diluting solvent is one or more of ethyl acetate, cyclohexane, n-hexane, acetone, butanone, methyl ethyl ketone, toluene and xylene.
In one embodiment, the silane coupling agent is one or more of 3-isocyanatopropyl trimethoxy siloxane, 3-isocyanatopropyl triethoxy siloxane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl triethoxy silane, 2- (3, 4-epoxycyclohexyl) ethyl trimethoxy silane and 2- (3, 4-epoxycyclohexyl) ethyl triethoxy silane.
In one embodiment, the curing catalyst is one or more of stannous octoate, dibutyltin dilaurate, dioctyltin dilaurate and dibutyltin diacetate.
The invention also aims to provide the epoxy resin modified polyurethane hyperbranched prepolymer.
The technical scheme for achieving the purpose is as follows.
An epoxy resin modified polyurethane hyperbranched prepolymer is prepared by the following method:
1) adding 10-20 parts by weight of epoxy resin, 5-10 parts by weight of diamine and 20-40 parts by weight of reaction solvent A into a reaction kettle provided with a condenser, and heating for reaction to obtain an amino polymer;
2) and sequentially adding 80-100 parts by weight of the amino polymer, 5-10 parts by weight of the chain extender, 10-20 parts by weight of the isocyanate monomer and 50-80 parts by weight of the reaction solvent B into a reaction kettle provided with a condenser, and reacting at normal temperature to obtain the self-made epoxy resin modified polyurethane hyperbranched prepolymer.
The invention also aims to provide application of the cement interface agent in preparation of a glue for caulking a high-speed rail ballastless track or an interface glue for sealing an assembly type building.
Compared with the prior art, the cement interface agent adopts the epoxy resin modified polyurethane hyperbranched prepolymer as a film-forming base polymer, and the hyperbranched polymer cured product has high crosslinking density, so that the defect of poor water resistance caused by low crosslinking density of the traditional polyurethane interface agent is overcome; in addition, the interface agent provided by the invention has excellent cement wetting and bonding performances, and the prepared cement interface agent for the ballastless track caulking glue can be applied to the glue for the high-speed rail ballastless track caulking and can be widely applied to interface glue treatment for assembly type building sealing.
Detailed Description
In order that the invention may be more readily understood, reference will now be made to the following more particular description of the invention, examples of which are set forth below. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. These embodiments are provided so that this disclosure will be thorough and complete. It is to be understood that the experimental procedures in the following examples, where specific conditions are not noted, are generally in accordance with conventional conditions, or with conditions recommended by the manufacturer. The various reagents used in the examples are commercially available.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
Example 1
The cement interface agent for the ballastless track caulking compound is prepared by the following method and raw materials:
(1) adding 10 parts by weight of epoxy resin E51 (epoxy value is 0.48-0.54(100g/g) in a reaction kettle with a condenser, the same as in the following example), 5 parts by weight of diethylenetriamine and 20 parts by weight of N, N-dimethylformamide into the reaction kettle, heating the mixture to 100 ℃, and stirring the mixture for 180min to react to obtain an amino polymer;
(2) sequentially adding 80 parts by weight of the amino polymer, 5 parts by weight of 1, 2-hexanediol, 10 parts by weight of toluene diisocyanate and 50 parts by weight of butyl acetate into a reaction kettle provided with a condenser, and stirring at normal temperature for 150min to react to obtain a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) uniformly mixing 100 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 50 parts by weight of ethyl acetate, 1 part by weight of 3-isocyanate propyl trimethoxy siloxane and 1 part by weight of stannous octoate to prepare the cement interface agent for the ballastless track caulking compound.
Example 2
The cement interface agent for the ballastless track caulking compound is prepared by the following method:
(1) adding 20 parts by weight of epoxy resin E44 (the epoxy value is 0.41-0.47(100g/g), the same as in the following example), 10 parts by weight of triethylene tetramine and 40 parts by weight of N, N-diethylformamide into a reaction kettle provided with a condenser, heating to 120 ℃, and stirring for 120min to react to obtain an amino polymer;
(2) sequentially adding 100 parts by weight of the amino polymer, 10 parts by weight of 1, 6-hexanediol, 20 parts by weight of diphenylmethane diisocyanate and 80 parts by weight of dimethyl carbonate into a reaction kettle provided with a condenser, and stirring at normal temperature for 100min to react to prepare a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) and uniformly mixing 120 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 70 parts by weight of cyclohexane, 10 parts by weight of 3-isocyanatopropyltriethoxysilane and 1 part by weight of dioctyltin dilaurate to obtain the cement interface agent for the ballastless track caulking compound.
Example 3
The cement interface agent for the ballastless track caulking compound is prepared by the following method:
(1) adding 10 parts by weight of epoxy resin E44, 10 parts by weight of epoxy resin E51, 10 parts by weight of tetraethylenepentamine and 30 parts by weight of N, N-dimethylacetamide into a reaction kettle provided with a condenser, heating to 110 ℃, and stirring for 150min to react to obtain an amino polymer;
(2) sequentially adding 90 parts by weight of the amino polymer, 8 parts by weight of 1, 4-butanediol, 15 parts by weight of isophorone diisocyanate and 65 parts by weight of dichlorobutane into a reaction kettle with a condenser, and stirring at normal temperature for 125min to react to obtain a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) and (3) uniformly mixing 105 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 60 parts by weight of n-hexane, 5 parts by weight of gamma- (2, 3-glycidoxy) propyl trimethoxy silane and 2.5 parts by weight of dibutyltin dilaurate to obtain the cement interface agent for the ballastless track caulking compound.
Example 4
The cement interface agent for the ballastless track caulking compound is prepared by the following method:
(1) adding 15 parts by weight of epoxy resin E44, 6 parts by weight of diethylenetriamine, 2 parts by weight of triethylene tetramine, 20 parts by weight of N, N-dimethylacetamide and 20 parts by weight of dimethyl sulfoxide into a reaction kettle provided with a condenser, heating to 115 ℃, and stirring for 170min to react to obtain an amino polymer;
(2) sequentially adding 95 parts by weight of the amino polymer, 6 parts by weight of 1, 3-propylene glycol, 11 parts by weight of hexamethylene diisocyanate and 70 parts by weight of isophorone into a reaction kettle with a condenser, and stirring at normal temperature for 120min to react to obtain a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) uniformly mixing 100 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 35 parts by weight of acetone, 30 parts by weight of butanone, 7 parts by weight of gamma- (2, 3-epoxypropoxy) propyltriethoxysilane and 2 parts by weight of dibutyltin diacetate to prepare the cement interface agent for the ballastless track caulking compound.
Example 5
The cement interface agent for the ballastless track caulking compound is prepared by the following method:
(1) adding 5 parts by weight of epoxy resin E44, 15 parts by weight of epoxy resin E51, 5 parts by weight of tetraethylenepentamine, 5 parts by weight of diethylenetriamine and 25 parts by weight of N-methylpyrrolidone into a reaction kettle provided with a condenser, heating to 105 ℃, and stirring for 140min to react to obtain an amino polymer;
(2) sequentially adding 88 parts by weight of the amino polymer, 7 parts by weight of 1, 3-propylene glycol, 3 parts by weight of 1, 6-hexanediol, 18 parts by weight of naphthalene diisocyanate and 66 parts by weight of No. 120 solvent oil into a reaction kettle provided with a condenser, and stirring at normal temperature for 135min to react to obtain a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) and uniformly mixing 115 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 55 parts by weight of methyl ethyl ketone, 8 parts by weight of 2- (3, 4-epoxy cyclohexane) ethyl trimethoxy silane and 1 part by weight of dibutyltin diacetate to prepare the cement interface agent for the ballastless track caulking compound.
Example 6
The cement interface agent for the ballastless track caulking compound is prepared by the following method:
(1) adding 12 parts by weight of epoxy resin E44, 8 parts by weight of epoxy resin E51, 8 parts by weight of triethylene tetramine, 22 parts by weight of N-methyl pyrrolidone and 13 parts by weight of N-ethyl pyrrolidone into a reaction kettle provided with a condenser, heating to 103 ℃, and stirring for 160min to react to obtain an amino polymer;
(2) sequentially adding 92 parts by weight of the amino polymer, 6 parts by weight of 1, 6-hexanediol, 10 parts by weight of hexamethylene diisocyanate and 73 parts by weight of dimethyl carbonate into a reaction kettle provided with a condenser, and stirring at normal temperature for 125min to react to prepare a self-made epoxy resin modified polyurethane hyperbranched prepolymer;
(3) and uniformly mixing 108 parts by weight of the self-made epoxy resin modified polyurethane hyperbranched prepolymer with 37 parts by weight of toluene, 30 parts by weight of xylene, 4 parts by weight of 2- (3, 4-epoxy cyclohexane) ethyl triethoxysilane and 1 part by weight of dibutyltin dilaurate to obtain the cement interface agent for the ballastless track caulking compound.
Comparative example 1
Polyurethane interfacial agent synthesized without epoxy modification:
(1) sequentially adding 20 parts by weight of ethylenediamine, 80 parts by weight of N, N-diethylformamide, 10 parts by weight of 1, 6-hexanediol, 20 parts by weight of diphenylmethane diisocyanate and 80 parts by weight of dimethyl carbonate into a reaction kettle provided with a condenser, and stirring at normal temperature for 100min to react to obtain a polyurethane prepolymer;
(2) and uniformly mixing 120 parts by weight of the polyurethane prepolymer with 70 parts by weight of cyclohexane, 10 parts by weight of 3-isocyanatopropyl triethoxy siloxane and 1 part by weight of dioctyltin dilaurate to obtain the cement interface agent for the ballastless track caulking compound.
The comprehensive performance test of the products of each embodiment is as follows:
the cement interface agent for the ballastless track caulking compound prepared in each embodiment adopts concrete (meeting the relevant provisions of GBT 13477.1-2002) as a test base material for shear strength, executes the relevant tests specified in the temporary technical conditions of TJ/GW 119-2013 ballastless track caulking material, and adds one test item of the retention rate of the bonding strength of bubble water 7d, namely, the ratio of the bonding strength before the bubble water to the bonding strength after the bubble water is adopted for representing. The test results of each example are shown in Table 1.
TABLE 1 test data
Wherein, the comparative example 1 is a self-made polyurethane interfacial agent which is not modified by epoxy and synthesized with polyfunctional groups in an ultrabranching way. From the above table, the bonding strength retention rate (55%) of the polyurethane interface agent without epoxy resin modification after being soaked in water for 7 days is obviously lower than that of the epoxy resin modified polyurethane interface agent disclosed by the invention after being soaked in water for 7 days, and the polyurethane interface agent modified by epoxy resin has the characteristic of improved water resistance. In addition, the rainy period in south China is long, the caulking interface of the ballastless track of the high-speed rail needs to be soaked in rainwater for a long time, and the polyurethane interface agent modified by the epoxy resin can be well suitable for outdoor extreme rainy and snowy weather.
The technical features of the above embodiments can be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the above embodiments are not described, however, as long as there is no contradiction between the combinations of the technical features, the scope of the present description should be considered as being described in the present specification.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. The cement interface agent is characterized by being prepared from the following components in parts by weight:
the epoxy resin modified polyurethane hyperbranched prepolymer is prepared by the following method:
1) adding 10-20 parts by weight of epoxy resin, 5-10 parts by weight of polyamine and 20-40 parts by weight of reaction solvent A into a reaction kettle, and heating for reaction to obtain an amino polymer;
2) and sequentially adding 80-100 parts by weight of the amino polymer, 5-10 parts by weight of the chain extender, 10-20 parts by weight of the isocyanate monomer and 50-80 parts by weight of the reaction solvent B into a reaction kettle, and reacting at normal temperature to obtain the epoxy resin modified polyurethane hyperbranched prepolymer.
2. The cement interface agent as claimed in claim 1, wherein the reaction conditions in step 1) are: heating to 100 ℃ and 120 ℃, and stirring for 120min and 180 min.
3. The cement interface agent as claimed in claim 1, wherein the epoxy resin is at least one of E-51 having an epoxy value of 0.48 to 0.54 and E44 having an epoxy value of 0.41 to 0.47.
4. The cement interface agent according to claim 1, wherein the polyamine is one or more of diethylenetriamine, triethylenetetramine and tetraethylenepentamine.
5. The cement interface agent according to claim 1, wherein the reaction solvent a is at least one of N, N-dimethylformamide, N-diethylformamide, N-dimethylacetamide, N-diethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, and N-ethylpyrrolidone; and/or the reaction solvent B is one or more of butyl acetate, dimethyl carbonate, dichlorobutane, isophorone and No. 120 solvent oil.
6. The cement interface agent as claimed in claim 1, wherein the chain extender is one or more of 1, 4-butanediol, 1, 2-ethanediol, 1, 3-propanediol and 1, 6-hexanediol.
7. The cement interface agent according to claim 1, wherein the isocyanate monomer is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, and naphthalene diisocyanate.
8. The cement interfacial agent according to any one of claims 1 to 7, wherein the diluent solvent is one or more of ethyl acetate, cyclohexane, n-hexane, acetone, butanone, methyl ethyl ketone, toluene and xylene; and/or
The silane coupling agent is one or more of 3-isocyanate propyl trimethoxy siloxane, 3-isocyanate propyl triethoxy siloxane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl triethoxy silane, 2- (3, 4-epoxycyclohexyl) ethyl trimethoxy silane and 2- (3, 4-epoxycyclohexyl) ethyl triethoxy silane; the curing catalyst is one or more of stannous octoate, dibutyltin dilaurate, dioctyltin dilaurate and dibutyltin diacetate.
9. The use of the cement interface agent as set forth in any one of claims 1 to 8 in the preparation of a glue for caulking a high-speed railway ballastless track or an interface glue for sealing a fabricated building.
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| CN109486457A (en) * | 2018-10-19 | 2019-03-19 | 长安大学 | A kind of high temperature resistant height glues high-strength and high ductility interlaminar bonding material and preparation method |
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| CN101358122A (en) * | 2007-07-30 | 2009-02-04 | 湖南神力实业有限公司 | One-component polyurethane adhesive from epoxy resin modification and preparation method thereof |
| CN103897140A (en) * | 2014-04-11 | 2014-07-02 | 合肥工业大学 | Epoxy resin modified polyurethane grouting and reinforcing material and preparation method thereof |
| CN105646812A (en) * | 2016-01-21 | 2016-06-08 | 苏州印丝特纺织数码科技有限公司 | Hyperbranched epoxy resin modified waterborne polyurethane emulsion and preparation method thereof |
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