CN116676066A - Self-healing polyurethane artificial turf back adhesive and preparation method thereof - Google Patents
Self-healing polyurethane artificial turf back adhesive and preparation method thereof Download PDFInfo
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- CN116676066A CN116676066A CN202310646735.0A CN202310646735A CN116676066A CN 116676066 A CN116676066 A CN 116676066A CN 202310646735 A CN202310646735 A CN 202310646735A CN 116676066 A CN116676066 A CN 116676066A
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- dihydric alcohol
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 46
- 239000000853 adhesive Substances 0.000 title claims abstract description 45
- 239000004814 polyurethane Substances 0.000 title claims abstract description 42
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 150000004985 diamines Chemical class 0.000 claims abstract description 13
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 238000003756 stirring Methods 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 16
- 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 16
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 16
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 15
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052786 argon Inorganic materials 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000004821 distillation Methods 0.000 claims description 6
- 238000001035 drying Methods 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
- 238000005406 washing Methods 0.000 claims description 6
- 239000009261 D 400 Substances 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 5
- -1 2,2' - [ dithio-bis (2, 1-ethylenedioxy) ] diethanol Chemical compound 0.000 claims description 4
- BJYNFUDMWCCZFC-UHFFFAOYSA-N 2-[(2-chloro-2-oxoethyl)disulfanyl]acetyl chloride Chemical compound ClC(=O)CSSCC(Cl)=O BJYNFUDMWCCZFC-UHFFFAOYSA-N 0.000 claims description 4
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 4
- 239000003292 glue Substances 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 229940043375 1,5-pentanediol Drugs 0.000 claims description 2
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 claims description 2
- KBRZQWPJGGMUJZ-UHFFFAOYSA-N 3-[(4-chloro-4-oxobutan-2-yl)disulfanyl]butanoyl chloride Chemical compound ClC(=O)CC(C)SSC(C)CC(Cl)=O KBRZQWPJGGMUJZ-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000004806 packaging method and process Methods 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims 3
- VSWMPZHJMCIQIC-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol Chemical compound OCSSCO VSWMPZHJMCIQIC-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 abstract description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 abstract description 2
- 238000004100 electronic packaging Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000010008 shearing Methods 0.000 abstract description 2
- 238000004132 cross linking Methods 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 239000008204 material by function Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 5
- 238000001723 curing Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
-
- 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
- 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
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C13/00—Pavings or foundations specially adapted for playgrounds or sports grounds; Drainage, irrigation or heating of sports grounds
- E01C13/08—Surfaces simulating grass ; Grass-grown sports grounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The application provides a self-healing polyurethane artificial turf back adhesive and a preparation method thereof, and mainly relates to the technical field of high-molecular functional materials and application thereof. The application takes dihydric alcohol containing disulfide bond and amide bond as reversible covalent bond source, diamine and dihydric alcohol as soft segment, non-aryl diisocyanate and trimethylolpropane trimethacrylate (TMPTMA) as hard segment to obtain the polyurethane adhesive with the functional cross-linking structure. The application introduces functional disulfide bond, amide bond and ureido group into polyurethane adhesive, and has high self-repairing property, high cohesiveness, high toughness and high shearing property. The polyurethane back adhesive has good adhesive property and excellent self-repairing property, has certain advantages in the fields of electronic packaging and textile fiber adhesion, and can be used for manufacturing artificial lawns.
Description
Technical Field
The application mainly relates to the technical field of self-repairing adhesives, in particular to a self-healing polyurethane artificial turf back adhesive and a preparation method thereof.
Background
The self-repairing polyurethane adhesive is widely paid attention to by people because of the multifunctional advantages of repairability, high toughness and the like, and has great progress in the fields of electronic packaging, substrate adhesion, automobile assembly, road pavement and the like. However, the conventional self-repairing adhesive has the problems that the use of flexible conductive gel has high curing temperature, short service life, contradiction between environment-friendly performance and physical performance, poor compatibility with a base material and the like, and the adhesive has the current situation that the toughness and the shear strength are difficult to balance, so that the practical application of the adhesive is limited to a certain extent.
In recent years, the advantages of high strength, high corrosion resistance, high abrasion resistance, self-repairing property, protection of the surface of a coating from ultraviolet radiation, and the like, based on a crosslinked network of urea-based hydrogen bonds having high binding energy, are widely applied in the fields of biomedicine, electronic components, interface bonding, and the like. The disulfide bond is used as a relatively stable reversible covalent bond, can endow the structure with high flexibility and good mechanical properties, and is widely applied to the fields of self-healing and detachable recovery of polyurethane adhesives.
The traditional single-component polyurethane adhesive has the problems of poor repair performance, poor heat resistance, low weather resistance, poor ageing resistance, incapability of being exposed outdoors for a long time, poor water resistance and alkali resistance and the like.
Disclosure of Invention
In order to solve the defects of the prior art, the application provides a novel preparation method of self-healing polyurethane back adhesive applied to an artificial lawn, wherein the application takes dihydric alcohol containing amide bonds and disulfide bonds or dihydric alcohol containing disulfide bonds as a polyurethane soft segment, takes non-aryl isocyanate as a hard segment, and adds a crosslinking agent of trimethylol propane trimethacrylate (TMPTMA) and trimethylol propane (TMP) to prepare the bi-component polyurethane adhesive which has high self-healing property, toughness, high shear strength, excellent heat resistance and aging resistance and better compatibility with artificial grass yarns and base cloth.
The application aims to achieve the aim, and the aim is achieved by the following technical scheme:
the self-healing polyurethane artificial turf back adhesive comprises a polyurethane adhesive, wherein the polyurethane adhesive comprises two components, namely a component A and a component B:
the component A comprises dihydric alcohol containing amide bond and disulfide bond, dihydric alcohol containing disulfide bond, non-aryl diisocyanate, catalyst dibutyl tin dilaurate and organic solvent a; wherein the molar ratio of diol to diisocyanate is 1.0:1.5 to 4.0, the total mass ratio of the organic solvent a to the dihydric alcohol and the diisocyanate is 2 to 10:1, a step of;
preferably, the molar ratio of the dihydric alcohol containing the amide bond and the disulfide bond to isophorone diisocyanate is 1.0:2.0, the total mass ratio of the organic solvent a to the dihydric alcohol and the diisocyanate is 4.0:1.0;
further, the dihydric alcohol containing disulfide bond is one of 1,1' -dithio-bi-methanol, 2-hydroxyethyl disulfide, 1' -dithio-bi (2-propanol) and 2,2' - [ dithio-bi (2, 1-ethylenedioxy) ] bi-ethanol;
the component B comprises diamine, dihydric alcohol, diisocyanate, catalyst dibutyltin dilaurate and an organic solvent B; wherein the molar ratio of diamine to glycol is 1.0:0.5 to 2.0, the molar ratio of the former two to diisocyanate being 1.0:1.5 to 4.0, the total mass ratio of the organic solvent b to the diamine, the dihydric alcohol and the diisocyanate is 2 to 10:1, a step of;
preferably, the molar ratio of diamine to glycol is 1.0:1.0, the molar ratio of the first two to diisocyanate being 1.0:2.0, the total mass ratio of the organic solvent a to the dihydric alcohol and the diisocyanate is 5.0:1.0;
further, the non-aryl diisocyanate is isophorone diisocyanate or hexamethylene diisocyanate;
further, the diamine is any one of polyetheramine D-230 and polyetheramine D-2000, polyetheramine D-400 and polyetheramine D-2000 mixture, and the mole ratio of polyetheramine D-230 to polyetheramine D-2000 is 1.0:0.5 to 10.0, wherein the mol ratio of the polyetheramine D-400 to the polyetheramine D-2000 is 1.0:0.5 to 20.0;
further, the dihydric alcohol is one of polyvinyl alcohol with Mw of 47000, 67000 and 89000 and polytetrafluoro dihydric alcohol (PTMEG-650, PTMEG-1000, PTMEG-2000 and PTMEG-3000);
the preparation process of the polyurethane back adhesive comprises a component A, a component B, a cross-linking agent and an organic solvent c, wherein the cross-linking agent comprises trimethylolpropane trimethacrylate and trimethylolpropane, and the mixing mole ratio of the component A to the component B is 1.0:0.2 to 5.0, the molar ratio of the former two to the crosslinking agent being 1.0:0.05 to 0.5, and the total mass ratio of the organic solvent c to the component A, the component B and the cross-linking agent is 1 to 5:1, a step of;
preferably, the molar ratio of component a to component B is 1.0:0.75, the molar ratio of the first two to the crosslinking agent being 1.0:0.25, the total mass ratio of the organic solvent c to the component A, the component B and the crosslinking agent is 3.0:1.0;
the organic solvent a, the organic solvent b and the organic solvent c are the same and are one or a mixture of more than one of tetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone;
the synthesis process of dihydric alcohol containing amide bond and disulfide bond specifically comprises the following steps:
s1: dispersing the monomer C and the acid binding agent D in the organic solvent D, and continuously stirring;
s2: dispersing the monomer E in an organic solvent d;
s3: placing the solution obtained in the step S2 into a constant pressure dropping funnel, dropwise adding the solution obtained in the step S1 into the solution, stirring at a low temperature in a nitrogen atmosphere;
s4: after the reaction is finished, washing and drying in a vacuum oven to obtain a product F;
s5: dispersing the monomer G in an organic solvent d, adding potassium carbonate, and continuously stirring;
s6: adding the product F and potassium iodide into the solution of S5, heating and refluxing in an oil bath, and stirring vigorously;
s7: cooling, precipitating, recrystallizing, and drying in a vacuum oven to obtain dihydric alcohol containing amide bonds and disulfide bonds;
further, in the step S1, the monomer C is 3-chloropropylamine, the acid-binding agent is any one of pyridine and triethylamine, the solvent D is any one of anhydrous tetrahydrofuran, dichloromethane, ethanol and N, N-dimethylformamide, the mass fraction of the acid-binding agent D is 0.05-0.5wt%, and the organic solvent D is 60-110 mL;
further, in the step S2, the monomer E is 2,2' -dithiodiacetyl chloride, 3- (2-chlorocarbonyl-ethyldisulfonyl) -propionyl chloride, 4' -dithiodibutyryl chloride or 3,3' -dithiodibutyryl chloride, and the molar ratio of the monomer C to the monomer E is 3.0-5.0: 1.0, wherein the organic solvent d is 50-80 mL;
further, the monomer F in the step S4 is a monomer containing an amide bond and a disulfide bond which is blocked by a chlorine atom;
further, in the step S5, the monomer G is one of 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol and p-hydroxyphenol, and the molar ratio of the product F to the monomer G is 1.0:2.0 to 4.0, wherein the molar ratio of the potassium carbonate to the monomer G is 2.0 to 4.0:1.0, wherein the organic solvent d is 80-160 mL;
further, the mass fraction of the potassium iodide in the step S6 is 0.02-0.1 wt%;
further, the reaction equation of the monomer containing amide bond and disulfide bond is prepared by taking the monomer C as chloropropylamine, the acid binding agent as triethylamine and the monomer E as 2,2' -dithiodiacetyl chloride:
further, taking the amide bond-containing disulfide bond-containing monomer as an example, the monomer G is 1, 3-propanediol, and the reaction equation for preparing the amide bond-containing disulfide bond-containing diol is:
further, the stirring time in the step S1 is 20-90 min;
further, the low-temperature stirring temperature in the step S3 is-30-10 ℃, the stirring time is 24-72 h, and the washing process is to wash water and the used solvent for 2-3 times;
further, the vacuum drying temperature in the steps S3 and S7 is 55-70 ℃ and the time is 18-36 h;
further, the continuous stirring time in the step S5 is 30-90 min;
further, the heating temperature in the step S6 is 90-115 ℃, and the stirring time is 20-30 hours;
further, the precipitation mode in the step S7 is precipitation in crushed ice, and recrystallization is carried out to obtain n-hexane, cyclohexane, ethanol and water in a volume ratio of 1:1 any one of solvents;
the synthesis process of the component A and the component B comprises the following specific steps:
(1) At the temperature higher than room temperature, dissolving dihydric alcohol containing amide bond and disulfide bond or dihydric alcohol containing disulfide bond, non-aryl diisocyanate and catalyst dibutyl tin dilaurate in an organic solvent a, heating in a gradient way, continuously stirring, protecting by argon, finishing the reaction, and distilling under reduced pressure to obtain a component A;
(2) At the temperature higher than room temperature, diamine, dihydric alcohol, non-aryl diisocyanate and catalyst dibutyl tin dilaurate are dissolved in an organic solvent B, the temperature is raised in a gradient way, continuous stirring and argon protection are carried out, the reaction is completed, and reduced pressure distillation is carried out to obtain a component B;
(3) And (3) dissolving the component A, the component B and the cross-linking agent in the organic solvent c at the temperature higher than the room temperature, heating in a gradient way, continuously stirring, stopping the reaction, distilling under reduced pressure to obtain the self-repairable polyurethane adhesive, and directly packaging by a glue filling machine.
Further, the temperature range higher than room temperature in the steps (1), (2) and (3) is 60-110 ℃, the gradient heating temperature rate is 5 ℃/min and the temperature fluctuation range is not more than 30 ℃, the consumption of the organic solvent is 50-120 mL, and the reduced pressure distillation temperature is 40-120 ℃;
further, the continuous stirring mode in the steps (1), (2) and (3) is mechanical stirring, the stirring speed is 200-1000 rpm, and the stirring time is 10-24 h;
further, the adding amount of the catalyst dibutyl tin dilaurate in the step (1) is 0.1-1 wt%, and the adding amount of the catalyst dibutyl tin dilaurate in the step (2) is 0.02-0.2 wt%;
the application mode of the self-healing polyurethane adhesive in the artificial turf field is as follows:
coating the encapsulated polyurethane adhesive prepared by the synthesis method of claim 4 on the surface of a base fabric, placing small clusters of artificial grass filaments above the base fabric, and curing to obtain an artificial lawn;
further, the coating mode is dispensing type, and the rubber tube is continuously and uniformly extruded on the surface of the base fabric;
further, the curing mode is two methods of heating curing and moisture curing, wherein the first method is to heat and cure in a hot melt adhesive mode, and the second method is to cure the unblocked isocyanate by contacting with moisture in the air;
furthermore, the moisture curing is applied to the primary molding process of the artificial turf, and the subsequent detachable secondary molding needs to use a heat curing mode.
Compared with the prior art, the application has the beneficial effects that:
the application provides a synthesis method of dihydric alcohol containing amide bond and disulfide bond, which is mainly used for purifying dihydric alcohol to obtain dihydric alcohol with high purity (more than 97 percent), improves the content of dynamic covalent bond, and can be applied to the preparation of self-repairing polyurethane adhesive.
The application provides a preparation method of a bi-component polyurethane adhesive combining reversible dynamic covalent bonds and ureido hydrogen bonds, which uses non-aryl diisocyanate as a hard segment structure, uses dihydric alcohol and diamine as a soft segment structure, uses trimethylolpropane trimethacrylate and trimethylolpropane as cross-linking agents to construct self-repairing polyurethane back adhesive, has high tensile property (780%), high self-repairing property (91%), and shearing strength (7.71N/mm < 2 >) and is beneficial to the research of the detachable artificial lawn, and the service life of the artificial lawn is prolonged;
the application utilizes the mode of introducing moisture to cure by using redundant isocyanate groups, reduces the manufacturing cost of the artificial turf, and is friendly to the environment.
Drawings
FIG. 1 is a morphology of the polyurethane adhesive prepared in example 1;
fig. 2 shows the self-healing mechanical property test (one set of plot 1, plot5, one set of plot 3, plot 4 and plot 2) of the polyurethane adhesive prepared in example 2.
Detailed Description
The application will be further described with reference to the accompanying drawings and specific embodiments. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Further, it will be understood that various changes and modifications may be made by those skilled in the art after reading the teachings of the application, and equivalents thereof fall within the scope of the application as defined by the claims.
Example 1
Preparation of component A: oil bath at 70℃12.1g (0.05 mol) of 2,2' - [ dithiobis (2, 1-ethylenedioxy) ] diethanol, 26.7g (0.04 mol) of isophorone diisocyanate and 0.6g of dibutyltin dilaurate were dissolved in 60mL of anhydrous DMF, stirred at 70℃for 2h, stirred at 80℃for 12h, argon-protected, the reaction was complete and distilled under reduced pressure at 100℃to give 29.5g of component A;
preparation of component B: 10.0g of a mixture of polyetheramine D-400 and polyetheramine D-2000 (molar ratio 1.0:1.0), 15.0g of PTMEG-1000, 20.0g of isophorone diisocyanate and 0.2g of dibutyltin dilaurate were dissolved in 80mL of anhydrous DMF at 60℃with stirring for 2h at 60℃with stirring for 12h at 80℃under argon protection, and the reaction was completed with distillation under reduced pressure at 100℃to give 32.9g of component B;
the preparation process of the polyurethane adhesive comprises the following steps: at the temperature of 60 ℃ in an oil bath, 20g of component A, 20g of component B and 15g of trimethylolpropane trimethacrylate are dissolved in 80mL of anhydrous DMF, stirred for 2 hours at the temperature of 60 ℃, stirred for 2 hours at the temperature of 80 ℃, and protected by argon at the temperature of 90 ℃ for 16 hours, and the reaction is completed, distilled under reduced pressure at the temperature of 100 ℃, and directly packaged by a glue filling machine, thus obtaining about 32.0g of polyurethane adhesive.
Example 2
Preparation of dihydric alcohol containing amide bond and disulfide bond: 18.712g (0.2 mol) of 3-chloropropylamine and 2.04g (0.2 mol) of acid-binding agent triethylamine are dispersed in 80mL of anhydrous DMF (dimethyl formamide) which is an organic solvent, and the mixture is placed in a three-neck flask and stirred for 50min; dispersing 10.96g (0.05 mol) of 2,2' -dithiodiacetyl chloride in 60mL of anhydrous DMF, and placing the solution into a constant pressure dropping funnel to be dropped into the solution when the temperature is minus 10 ℃ under the nitrogen atmosphere for 1.5h; stopping the experiment when the reaction is carried out for 36 hours, dripping the solution into 100mL of distilled water for washing, adding the solution into DMF for washing twice after the suction filtration is finished, and drying the solution for 24 hours at the temperature of 60 ℃ in a vacuum drying oven after the suction filtration to obtain 15.2g of light yellow product with the yield of 91.2%; 9.012g (0.1 mol) of 1, 4-butanediol are dispersed in anhydrous DMF as an organic solvent, 13.8g (0.1 mol) of potassium carbonate are added, and the mixture is magnetically stirred for 50min; 15.2g (0.045 mol) of the product and 0.03g (0.18 mmol) of potassium iodide are weighed and added into the solution, and the mixture is stirred for 1h at 60 ℃, 1h at 80 ℃ and 22h at 105 ℃, and condensed and refluxed; dripping the obtained solution into ice water for precipitation, filtering, recrystallizing with n-hexane, filtering, and drying in a vacuum oven at 60 ℃ for 24 hours to obtain 13.6g of dihydric alcohol containing amide bonds and disulfide bonds;
preparation of component A: oil bath at 60 deg.C, 8.8g (0.02 mol) of dihydric alcohol containing amide bond and disulfide bond, 8.9g (0.04 mol) of isophorone diisocyanate and 0.3g of dibutyltin dilaurate are dissolved in 50mL of anhydrous DMF, stirred at 60 deg.C for 2h, stirred at 70 deg.C for 12h under argon protection, the reaction is completed, and distilled under reduced pressure at 90 deg.C to obtain 10.6g of component A;
preparation of component B: oil bath at 60℃, 4.0g of a mixture of polyetheramine D-230 and polyetheramine D-2000 (molar ratio 1.0:2.0), 10.0g of PTMEG-1000, 15.0g of isophorone diisocyanate and 0.1g of dibutyltin dilaurate were dissolved in 60mL of anhydrous DMF, stirred at 60℃ for 2h, stirred at 70℃ for 12h, argon-protected, the reaction was completed, and distilled under reduced pressure at 90℃ to give 16.67g of component B;
the preparation process of the polyurethane adhesive comprises the following steps: 10g of component A, 15g of component B and 10g of trimethylolpropane trimethacrylate are dissolved in 80mL of anhydrous DMF at 60 ℃ in an oil bath, stirred for 3h at 60 ℃, stirred for 15h at 80 ℃, under the protection of argon, the reaction is completed, the reduced pressure distillation at 90 ℃ is carried out, and the polyurethane adhesive of about 24.0g is obtained after direct encapsulation by a glue filling machine.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present application, and are not limiting; although the application has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present application.
Claims (9)
1. The self-healing polyurethane artificial turf back adhesive comprises a polyurethane adhesive and is characterized in that: the polyurethane adhesive comprises two components, namely a component A and a component B;
the component A comprises dihydric alcohol containing amide bond and disulfide bond, dihydric alcohol containing disulfide bond, non-aryl diisocyanate, catalyst dibutyl tin dilaurate and organic solvent a; wherein the molar ratio of diol to diisocyanate is 1.0:1.5 to 4.0, the total mass ratio of the organic solvent a to the dihydric alcohol and the diisocyanate is 2 to 10:1, a step of;
the component B comprises diamine, dihydric alcohol, diisocyanate, catalyst dibutyltin dilaurate and an organic solvent B; wherein the molar ratio of diamine to glycol is 1.0:0.5 to 2.0, the molar ratio of the former two to diisocyanate being 1.0:1.5 to 4.0, the total mass ratio of the organic solvent b to the diamine, the dihydric alcohol and the diisocyanate is 2 to 10:1, a step of;
the preparation process of the polyurethane back adhesive comprises a component A, a component B, a cross-linking agent and an organic solvent c, wherein the cross-linking agent comprises trimethylolpropane trimethacrylate and trimethylolpropane, and the mixing mole ratio of the component A to the component B is 1.0:0.2 to 5.0, the molar ratio of the former two to the crosslinking agent being 1.0:0.05 to 0.5, and the total mass ratio of the organic solvent c to the component A, the component B and the cross-linking agent is 1 to 5:1, a step of;
the organic solvent a, the organic solvent b and the organic solvent c are the same and are one or a mixture of a plurality of tetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide and N-methylpyrrolidone.
2. The self-healing polyurethane artificial turf back adhesive according to claim 1, wherein: the non-aryl diisocyanate is isophorone diisocyanate or hexamethylene diisocyanate.
3. The method for preparing the self-healing polyurethane artificial turf back adhesive, which is disclosed in claim 1, is characterized in that: the preparation process of the dihydric alcohol containing the amide bond and the disulfide bond specifically comprises the following steps:
s1: dispersing the monomer C and the acid binding agent D in the organic solvent D, and continuously stirring;
s2: dispersing the monomer E in an organic solvent d;
s3: placing the solution obtained in the step S2 into a constant pressure dropping funnel, dropwise adding the solution obtained in the step S1 into the solution, stirring at a low temperature in a nitrogen atmosphere;
s4: after the reaction is finished, washing and drying in a vacuum oven to obtain a product F;
s5: dispersing the monomer G in an organic solvent d, adding potassium carbonate, and continuously stirring;
s6: adding the product F and potassium iodide into the solution of S5, heating and refluxing in an oil bath, and stirring vigorously;
s7: cooling, precipitating, recrystallizing, and drying in a vacuum oven to obtain dihydric alcohol containing amide bonds and disulfide bonds;
the monomer C in the step S1 is 3-chloropropylamine, the acid-binding agent is any one of pyridine and triethylamine, the solvent D is any one of anhydrous tetrahydrofuran, dichloromethane, ethanol and N, N-dimethylformamide, the mass fraction of the acid-binding agent D is 0.05-0.5wt%, and the organic solvent D is 60-110 mL;
the monomer E in the step S2 is 2,2' -dithiodiacetyl chloride, 3- (2-chlorocarbonyl-ethyldisulfonyl) -propionyl chloride, 4' -dithiodibutyryl chloride and 3,3' -dithiodibutyryl chloride, and the molar ratio of the monomer C to the monomer E is 3.0-5.0: 1.0, wherein the organic solvent d is 50-80 mL;
step S4, the monomer F is a chlorine atom end capped amide bond-containing and disulfide bond-containing monomer;
the monomer G in the step S5 is one of 1, 3-propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol and p-hydroxyphenol, and the molar ratio of the product F to the monomer G is 1.0:2.0 to 4.0, wherein the molar ratio of the potassium carbonate to the monomer G is 2.0 to 4.0:1.0, wherein the organic solvent d is 80-160 mL;
and the mass fraction of the potassium iodide in the step S6 is 0.02-0.1 wt%.
4. The method for preparing the self-healing polyurethane artificial turf back adhesive according to claim 3, wherein the method comprises the following steps: the synthesis process of the component A and the component B comprises the following specific steps:
(1) At the temperature higher than room temperature, dissolving dihydric alcohol containing amide bond and disulfide bond or dihydric alcohol containing disulfide bond, non-aryl diisocyanate and catalyst dibutyl tin dilaurate in an organic solvent a, heating in a gradient way, continuously stirring, protecting by argon, finishing the reaction, and distilling under reduced pressure to obtain a component A;
(2) At the temperature higher than room temperature, diamine, dihydric alcohol, non-aryl diisocyanate and catalyst dibutyl tin dilaurate are dissolved in an organic solvent B, the temperature is raised in a gradient way, continuous stirring and argon protection are carried out, the reaction is completed, and reduced pressure distillation is carried out to obtain a component B;
(3) And (3) dissolving the component A, the component B and the cross-linking agent in the organic solvent c at the temperature higher than the room temperature, heating in a gradient way, continuously stirring, stopping the reaction, distilling under reduced pressure to obtain the self-repairable polyurethane adhesive, and directly packaging by a glue filling machine.
5. The self-healing polyurethane artificial turf back adhesive according to claim 1, wherein: the dihydric alcohol containing disulfide bond is one of 1,1' -dithio-dimethanol, 2-hydroxyethyl disulfide, 1' -dithio-bis (2-propanol) and 2,2' - [ dithio-bis (2, 1-ethylenedioxy) ] diethanol.
6. The self-healing polyurethane artificial turf back adhesive according to claim 1, wherein: the diamine is any one of polyetheramine D-230 and polyetheramine D-2000, polyetheramine D-400 and polyetheramine D-2000 mixture, and the mole ratio of polyetheramine D-230 to polyetheramine D-2000 is 1.0:0.5 to 10.0, wherein the mol ratio of the polyetheramine D-400 to the polyetheramine D-2000 is 1.0:0.5 to 20.0.
7. The self-healing polyurethane artificial turf back adhesive according to claim 1, wherein: the dihydric alcohol is one of polyvinyl alcohol with Mw of 47000, 67000 and 89000 and polytetrafluoro dihydric alcohol (PTMEG-650, PTMEG-1000, PTMEG-2000 and PTMEG-3000).
8. The method for preparing the self-healing polyurethane artificial turf back adhesive according to claim 3, wherein the method comprises the following steps: the stirring time of the step S1 is 20-90 min, the low-temperature stirring temperature of the step S3 is-30-10 ℃, the stirring time is 24-72 h, the washing process is that water and used solvents are washed for 2-3 times, the vacuum drying temperature of the steps S3 and S7 is 55-70 ℃, the time is 18-36 h, the continuous stirring time of the step S5 is 30-90 min, the heating temperature of the step S6 is 90-115 ℃, the stirring time is 20-30 h, the precipitation mode of the step S7 is that the precipitate is carried out in crushed ice, and the recrystallization is that the volume ratio of n-hexane, cyclohexane, ethanol and water is 1:1 solvent.
9. The method for preparing the self-healing polyurethane artificial turf back adhesive, which is disclosed in claim 4, is characterized in that: the temperature range higher than room temperature in the steps (1), (2) and (3) is 60-110 ℃, the gradient heating temperature rate is 5 ℃/min and the temperature fluctuation range is not more than 30 ℃, the organic solvent dosage is 50-120 mL, the reduced pressure distillation temperature is 40-120 ℃, the continuous stirring mode in the steps (1), (2) and (3) is mechanical stirring, the stirring rate is 200-1000 r/min, the stirring time is 10-24 h, the catalyst dibutyl tin dilaurate in the step (1) is 0.1-1 wt% and the catalyst dibutyl tin dilaurate in the step (2) is 0.02-0.2 wt%.
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