CN110452103A - Anthracene dimer compound and its preparation and use - Google Patents
Anthracene dimer compound and its preparation and use Download PDFInfo
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- CN110452103A CN110452103A CN201910823063.XA CN201910823063A CN110452103A CN 110452103 A CN110452103 A CN 110452103A CN 201910823063 A CN201910823063 A CN 201910823063A CN 110452103 A CN110452103 A CN 110452103A
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- performed polymer
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- 238000002360 preparation method Methods 0.000 title claims abstract description 48
- -1 Anthracene dimer compound Chemical class 0.000 title claims abstract description 32
- 230000001070 adhesive effect Effects 0.000 claims abstract description 55
- 239000000853 adhesive Substances 0.000 claims abstract description 50
- 239000004814 polyurethane Substances 0.000 claims abstract description 49
- 229920002635 polyurethane Polymers 0.000 claims abstract description 49
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 239000004970 Chain extender Substances 0.000 claims abstract description 24
- 239000003063 flame retardant Substances 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 239000000047 product Substances 0.000 claims description 27
- 230000003287 optical effect Effects 0.000 claims description 26
- 230000004044 response Effects 0.000 claims description 26
- 239000003960 organic solvent Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 17
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 11
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011256 inorganic filler Substances 0.000 claims description 8
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 4
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 239000000084 colloidal system Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 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 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000008439 repair process Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920000297 Rayon Polymers 0.000 description 5
- 150000008425 anthrones Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003292 glue Substances 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- HHDUMDVQUCBCEY-UHFFFAOYSA-N 4-[10,15,20-tris(4-carboxyphenyl)-21,23-dihydroporphyrin-5-yl]benzoic acid Chemical compound OC(=O)c1ccc(cc1)-c1c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc([nH]2)c(-c2ccc(cc2)C(O)=O)c2ccc(n2)c(-c2ccc(cc2)C(O)=O)c2ccc1[nH]2 HHDUMDVQUCBCEY-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 150000001454 anthracenes Chemical class 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000010008 shearing Methods 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 3
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical group O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 3
- 229940001007 aluminium phosphate Drugs 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- CWZPGMMKDANPKU-UHFFFAOYSA-L butyl-di(dodecanoyloxy)tin Chemical compound CCCC[Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O CWZPGMMKDANPKU-UHFFFAOYSA-L 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002917 oxazolidines Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000012970 tertiary amine catalyst Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000012974 tin catalyst Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- XJRAOMZCVTUHFI-UHFFFAOYSA-N isocyanic acid;methane Chemical compound C.N=C=O.N=C=O XJRAOMZCVTUHFI-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008263 repair mechanism Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000012781 shape memory material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QUBMWJKTLKIJNN-UHFFFAOYSA-B tin(4+);tetraphosphate Chemical compound [Sn+4].[Sn+4].[Sn+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QUBMWJKTLKIJNN-UHFFFAOYSA-B 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/92—Systems containing at least three condensed rings with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a kind of anthracene dimer compound and its preparation and uses.The structural formula of the anthracene dimer compound is as follows:
Description
Technical field
The invention belongs to adhesive technology fields, and in particular to a kind of anthracene dimer compound and its preparation and use.
Background technique
Adhesive for polyurethane is because it has many advantages, such as that bonding force is strong, initial adhesion force is big, lower temperature resistance outstanding, in automobile, wood
The fields such as work, packaging, building are commonly employed.It however during use, can not due to being often exposed in environment
Avoid can by collide, kinking, scraping, the external actions such as chemical attack and there is slight crack and defect.If we can be in gluing
The damage of agent early stage or slight crack are repaired, and for eliminating safe hidden trouble, the service life of delay product is all of great significance.
It in order to solve this problem, the use of the adhesive for polyurethane with self-healing function is one of most efficient method.
Polyurethane has proved to be the shape-memory material of achievable self-repair function.It usually, can according to the difference of repair mechanisms
It is divided into Intrinsical and repairs system and foreign aid's type reparation system.It is exhausted once foreign aid's type system has crosslinking agent, material will not
Has the shortcomings that self-repair function.And Intrinsical repairs system then and theoretically has unlimited reparation number.Wherein, in polyurethane sheet
In sign type repair materials, a hot spot for carrying out that thermal reversion selfreparing is research is reacted using Diels-Alder.However polyurethane
The actual use environment of adhesive constrains the utilization that adhesive for polyurethane is answered in hot repair.Multiple compared to hot repair, light reparation is to poly- ammonia
The requirement of ester adhesive use environment is low, easy to operate, is easy to the realization of repair process.
Then, often there is light repairing performance and hardness, adhesive property, anti-flammability in current light reparation adhesive for polyurethane
The problem of energy etc. cannot be taken into account.It would therefore be highly desirable to develop one kind can light reparation again not to its hardness, adhesive property, flame retardant property
Etc. the polyurethane adhesive having an impact.
Summary of the invention
Based on this, the main object of the present invention is to provide a kind of anthracene dimer compound.Using anthracene dimer compound as
The photoresponse performed polymer of photoresponse chain extender preparation is the polyurethane adhesive of raw material preparation, has good light repairing performance, and
It solidifies hardness, adhesive property, flame retardant property and is not negatively affected.
The purpose of the present invention is realized by following proposal:
The main object of the present invention is to provide a kind of anthracene dimer compound, and the structural formula of the compound is as follows:In formula, R is straight chain or branched alkyl.
R is the straight chained alkyl of C2-C6 in one of the embodiments,.
R is positive butane group in one of the embodiments,.
A further object of the invention is to provide a kind of preparation method of above-mentioned anthracene dimer compound, the preparation method packet
Include following steps:
(1) X-R-OH and dihydropyran are reacted under catalyst M, X is halogen；
(2) by anthrone in organic solvent a, reaction product obtained by step (1) is added, alkali is reacted；
(3) reaction product obtained by step (2) is dissolved in organic solvent b, ultraviolet light irradiation；
(4) step (3) products therefrom is dissolved in organic solvent c, catalyst n reaction is added.
In one of the embodiments, in step (1), the catalyst M is aluminium phosphate catalyst；The temperature of the reaction
It is 85-95 DEG C, the time of the reaction is 0.8-1.6h；In parts by weight, every 100 parts of X-R-OH needs 150-250 parts
Dihydropyran and 3-7 parts of catalyst M.
In one of the embodiments, in step (2), the organic solvent a is tetrahydrofuran, and the alkali is hydroxide
Sodium；The temperature of the reaction is 40-80 DEG C, and the time of reaction is 20-28h；In parts by weight, every 100 parts of anthrones need 250-
A, 15-25 parts of alkali of 350 parts of organic solvents and 110-140 parts of step (1) products.
In one of the embodiments, in step (3), the organic solvent b is ethyl acetate, and the time of the irradiation is
15-23h；In parts by weight, every 100 parts of steps (2) product needs 80-130 parts of organic solvent b.
In one of the embodiments, in step (4), the organic solvent c is methylene chloride, and the catalyst n is to have
Machine tin-phosphate catalyst；The temperature of the reaction is 40-55 DEG C, and the reaction time is 1.5-2.5h；Every 100 parts of steps
(3) products therefrom needs c and 0.5-2 parts of catalyst ns of 80-130 parts of organic solvents.
A further object of the invention is to provide purposes of the above-mentioned anthracene dimer compound of one kind as photoresponse chain extender.
A further object of the invention is to provide a kind of photoresponse performed polymer, in parts by weight, the photoresponse performed polymer
Preparing raw material includes: 100 parts of isocyanates, 1-10 parts of photoresponse chain extenders, 0.01-3 parts of catalyst；The photoresponse chain extender
For above-mentioned anthracene dimer compound.
In one of the embodiments, in parts by weight, the raw material for preparing of the photoresponse performed polymer includes: 100 parts different
Cyanate, 5-8 parts of photoresponse chain extenders, 0.1-0.5 parts of catalyst.
The isocyanates is the isocyanates that functional group is more than or equal to 2 in one of the embodiments,；The catalyst
For stannous octoate catalyst.
A further object of the invention is to provide a kind of preparation method of above-mentioned photoresponse performed polymer, the preparation method packet
It includes following steps: taking the isocyanates, photoresponse chain extender, catalyst, mix reaction.
The temperature of the reaction is 40-80 DEG C in one of the embodiments, and the time of the reaction is 1-5h；It is described
The method of mixing is using stirring.
A further object of the invention is to provide above-mentioned photoresponse performed polymer and is preparing the use in light selfreparing polyurethane adhesive
On the way.
A further object of the invention is to provide a kind of smooth selfreparing polyurethane adhesive, in parts by weight, the polyurethane adhesive
Preparing raw material includes: 80-160 parts of optical Response performed polymer, and 1-20 parts of fire retardant, 0.01-5 parts of catalyst, inorganic filler 50-
200 parts and deicer 1-8 parts；
The optical Response performed polymer is above-mentioned photoresponse performed polymer.
In one of the embodiments, in parts by weight, the raw material for preparing of the polyurethane adhesive includes: optical Response pre-polymerization
80-160 parts of body, 14-16 parts of fire retardant, 0.5-1.5 parts of catalyst, 60-90 parts and deicer 3-7 parts of inorganic filler.
The fire retardant is Halogen liquid flame retardant in one of the embodiments,.
In one of the embodiments, the catalyst be one of organic tin catalyst and tertiary amine catalyst or
Two kinds.
The inorganic filler is one of white carbon black, calcium carbonate, aluminium hydroxide and carbon black in one of the embodiments,
Or a variety of combination.
The deicer is one of the oxazolidine of monocycle and bicyclic oxazolidine or two in one of the embodiments,
Kind.
A further object of the invention is to provide a kind of preparation method of above-mentioned light selfreparing polyurethane adhesive, the preparation side
Method includes the following steps: to take the optical Response performed polymer, fire retardant, inorganic filler, deicer, mixes, the catalysis is added
Agent mixes, deaeration.
For the method for the mixing using stirring, the mixing is to carry out at normal temperature, described in one of the embodiments,
Deaeration is to vacuumize lower progress.
Compared with the existing technology, the invention has the following beneficial effects:
The present invention provides a kind of anthracene dimer compound, is prepared using the anthracene dimer compound as photoresponse chain extender
Photoresponse performed polymer is the polyurethane adhesive of raw material preparation, has good light repairing performance, and it solidifies hardness, caking property
Energy, flame retardant property are not negatively affected.
Specific embodiment
It to facilitate the understanding of the present invention, below will be to invention is more fully described.But the present invention can be to be permitted
Mostly different form is realized, however it is not limited to embodiment described herein.On the contrary, purpose of providing these embodiments is makes
It is more thorough and comprehensive to the understanding of the disclosure.
Unless otherwise defined, all technical and scientific terms used herein and belong to technical field of the invention
The normally understood meaning of technical staff is identical.Term as used herein in the specification of the present invention is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term as used herein "and/or" includes one or more phases
Any and all combinations of the listed item of pass.
The present embodiment provides a kind of anthracene dimer compound, the structural formula of the compound is as follows:
In formula, R is straight chain or branched alkyl.
It is in embodiment at one, R is the straight chained alkyl of C2-C6.
In a preferred embodiment, R is butane group.
The present embodiment carries out specific explanations explanation by taking normal butane base as an example.
The present embodiment also provides a kind of preparation method of above-mentioned anthracene dimer compound, and the preparation method includes as follows
Step:
(1) X-R-OH and dihydropyran are reacted under catalyst M, X is halogen.
(2) by anthrone in organic solvent a, reaction product obtained by step (1) is added, alkali is reacted；
(3) reaction product obtained by step (2) is dissolved in organic solvent b, ultraviolet light irradiation；
(4) step (3) products therefrom is dissolved in organic solvent c, catalyst n reaction is added.
In the step of the present embodiment (1), the catalyst M is aluminium phosphate catalyst；The temperature of the reaction is 85-95
DEG C, the time of the reaction is 0.8-1.6h；In parts by weight, every 100 parts of X-R-OH needs 150-250 parts of dihydropyran
With 3-7 parts of catalyst M.It is understood that after reaction, can be removed anti-to obtain the reaction product of higher yields
Answer the catalyst M and remaining dihydropyran in system.The method for removing catalyst M for example filters.Remove remaining dihydro
The method of pyrans such as vacuum rotary steam.By step (1), the hydroxyl of X-R-OH is protected, corresponding to obtain
Explanation will be explained in detail by taking the bromo- n-butyl alcohol of 4- as an example below.
In the step of the present embodiment (2), the organic solvent a is tetrahydrofuran, and the alkali is sodium hydroxide；The reaction
Temperature be 40-80 DEG C, time of reaction is 20-28h；In parts by weight, every 100 parts of anthrones need 250-350 parts it is organic molten
A, 15-25 parts of alkali of agent and 110-140 parts of step (1) products.It is understood that in order to obtain the reaction product of higher yields,
After reaction, catalyst (for example, by using the mode of filtering) in reaction system and organic solvent a can be removed (for example, by using rotation
Turn evaporation), it is then dissolved in chloroform, is washed with distilled water three times, then chloroformic solution is dried in vacuo.
In the step of the present embodiment (3), the organic solvent b is ethyl acetate, and the time of the irradiation is 15-23h；With
Parts by weight meter, every 100 parts of steps (2) product need 80-130 parts of organic solvent b.It is understood that higher in order to obtain
The reaction product of yield can remove organic solvent b (for example, by using rotary evaporation) in reaction system vacuum again after reaction
It is dry, finally obtain white product.By step (3), the product of anthracene dimeric structure is generated.
In the present embodiment step (4), the organic solvent c is methylene chloride, and the catalyst n is organotin-phosphate
Catalyst；The temperature of the reaction is 40-55 DEG C, and the reaction time is 1.5-2.5h；Every 100 parts of steps (3) products therefrom
Need c and 0.5-2 parts of catalyst ns of 80-130 parts of organic solvents.Organic solvent c is methylene chloride, reaction product obtained by step (3)
It needs to be added under the conditions of ice-water bath in organic solvent c.It is understood that in order to obtain the reaction product of higher yields,
After reaction, catalyst (for example, by using filtering), the organic solvent c that can be removed in reaction system (are steamed for example, by using rotation
Hair), it washs, vacuum drying.
The present embodiment also provides purposes of the above-mentioned anthracene dimer compound as photoresponse chain extender.
The present embodiment also provides a kind of photoresponse performed polymer, and in parts by weight, the photoresponse performed polymer prepares raw material
It include: 100 parts of isocyanates, 1-10 parts of photoresponse chain extenders, 0.01-3 parts of catalyst；The photoresponse chain extender is above-mentioned anthracene
Dimer compound.
In one embodiment, in parts by weight, the raw material for preparing of the photoresponse performed polymer includes: 100 parts of isocyanic acids
Ester, 5-8 parts of photoresponse chain extenders, 0.1-0.5 parts of catalyst.
In one embodiment, the isocyanates is the isocyanates that functional group is more than or equal to 2, for example, liquefaction hexichol
Methane diisocyanate (liquefied mdi), polymerization diphenylmethane diisocyanate, hexamethylene diisocyanate (HDI) and isophthalic
Diformazan based isocyanate (XDI) etc.；The catalyst is stannous octoate catalyst.
The present embodiment also provides a kind of preparation method of above-mentioned photoresponse performed polymer, and the preparation method includes following step
It is rapid: to take the isocyanates, photoresponse chain extender, catalyst, mix reaction.
In one embodiment, the temperature of the reaction is 40-80 DEG C, and the time of the reaction is 1-5h.It is understood that
, the mode of mixing includes but is not limited to stir.
At 40000-90000cps (25 DEG C), isocyanide acid content exists the viscosity of optical Response performed polymer provided in this embodiment
10-25%.
The present embodiment provides above-mentioned photoresponse performed polymers to prepare the purposes in light selfreparing polyurethane adhesive.
The present embodiment provides a kind of smooth selfreparing polyurethane adhesives, and in parts by weight, the polyurethane adhesive prepares raw material packet
It includes:
In one embodiment, in parts by weight, the raw material for preparing of the polyurethane adhesive includes:
In one embodiment, the fire retardant is selected from Halogen liquid flame retardant, and total addition level is optical Response pre-polymerization
The 1-20% of body total weight.
In one embodiment, the catalyst can be organic tin catalyst such as stannous octoate, two fourth of tin dilaurate
Ji Xi etc. or tertiary amine catalyst such as triethylene two press, triethanolamine etc..The additive amount of catalyst is that optical Response is pre-
The 0.01-5% of aggressiveness total weight.
The inorganic filler can be one of white carbon black, calcium carbonate, aluminium hydroxide or carbon black or a variety of mixing, inorganic to fill out
The total addition level of material accounts for the 50-200% of optical Response performed polymer total weight.
The deicer is liquid deicer, is monocycle or bicyclic oxazolidine.The additive amount of deicer is photoresponse
The 1-8% of property performed polymer total weight.
Smooth selfreparing polyurethane adhesive provided in this embodiment is single-component glue, and viscosity before curing is in 90000-
160000cps (25 DEG C), isocyanate group mass contg is in 1-5%.
The present embodiment provides a kind of preparation method of smooth selfreparing polyurethane adhesive, the preparation method includes the following steps:
The optical Response performed polymer, fire retardant, inorganic filler, deicer are taken, is mixed, the catalyst is added and mixes, deaeration.
In one embodiment, the method for the mixing is using stirring, and the mixing is to carry out at normal temperature, the deaeration
It is to carry out under vacuum.
Number involved in following embodiment refers both to parts by weight.
Agents useful for same can routinely be bought from market in following embodiment.
Embodiment 1: the preparation of anthracene dimer compound
The present embodiment provides a kind of anthracene dimer compounds and preparation method thereof.The following synthetic route of the preparation method into
Row:
The preparation method specifically includes the following steps:
Step 1: the bromo- n-butyl alcohol of 100 parts of 4- being added in 200 parts of dihydropyran, later 5 parts of aluminophosphate catalyst
Agent is stirred 1 hour in reflux unit at 90 DEG C.It is filtered to remove aluminium phosphate catalyst after completion of the reaction, filtrate decompression revolving is removed
Dihydropyran concentration is gone to obtain product, yield 95%.
Step 2: taking 100 parts of anthrones to be dissolved in 300 parts of tetrahydrofurans, add 20 parts of potassium hydroxide and step 1 synthetic product
It 120 parts, flows back lower 75 DEG C and stirs 24 hours.It filters after solution temperature is down to 25 DEG C after completion of the reaction, later rotates filtrate.
Product is dissolved in chloroform again, is washed with distilled water three times.Chloroformic solution is dried in vacuo 3 hours again, obtains yellow liquid, is produced
Rate is 92%.
Step 3: taking the product of 100 parts of steps 3 to be dissolved in 100 parts of ethyl acetate, irradiated at ultraviolet lamp (wavelength 365nm)
18 hours.Revolving removes ethyl acetate later, and vacuum drying obtains white product, yield 98%.
Step 4: the product stirring that 100 parts of steps 4 obtain being dissolved in 100 parts of methylene chloride in ice-water bath.Product dissolution
1 part of organotin-phosphate catalyst is added later, back flow reaction 2 hours at 45 DEG C.It filters, rotate later, washing, vacuum
It is dry to obtain anthracene dimer compound, yield 87%.
Product nucleus magnetic hydrogen spectrum (D2O): δ 2.29 (m), 3.31 (t), 3.78 (t), 6.98 (m), 7.14 (m), 7.18 (m)
ppm。
Product infrared spectrum: 3420,3077,2956,2770,1680,1495,1365,1160,1056,1036,784cm-1。
Embodiment 2: the preparation of optical Response performed polymer (A)
The ten thousand magnificent chemistry MDI-100LL model liquefied mdis for taking 100 parts, are added the anthracene dimer prepared in 5 parts of embodiments 1
0.1 part of stannous octoate catalyst is added in compound, accelerates to be stirred to react 2 hours at 50 DEG C, vacuum defoamation.
The viscosity of above-mentioned performed polymer is at 40000-50000cps (25 DEG C).
Embodiment 3: the preparation of optical Response performed polymer (B)
The ten thousand magnificent chemistry MDI-100LL model liquefied mdis for taking 100 parts, are added the anthracene dimer prepared in 8 parts of embodiments 1
0.1 part of stannous octoate catalyst is added in compound, accelerates to be stirred to react 2 hours at 50 DEG C, vacuum defoamation.
The viscosity of above-mentioned performed polymer is at 70000-90000cps (25 DEG C).
Example 4: the preparation of light selfreparing polyurethane adhesive (I)
100 parts of optical Response performed polymer (A), 15 parts of Qingdao connection is taken to beautify work TCPP model liquid flame retardants, 80 parts of hydrogen
Aluminium oxide and 5 parts of Anxiang Ai Lite Chemical Co., Ltd. monocycle oxazolidines, stirring at normal temperature 20 minutes.It is added later into reaction kettle
1 part of butyl tin dilaurate.High-speed stirred disperses 1 hour, vacuum defoamation under room temperature.It prepares raw material and is shown in Table 1.
The viscosity of above-mentioned polyurethane adhesive is at 120000-128000cps (25 DEG C).
Embodiment 5: the preparation of light selfreparing polyurethane adhesive (II)
100 parts of optical Response performed polymer (B), 15 parts of Qingdao connection is taken to beautify work TCPP model liquid flame retardants, 80 parts of hydrogen
Aluminium oxide and 5 parts of Anxiang Ai Lite Chemical Co., Ltd. monocycle oxazolidines, stirring at normal temperature 20 minutes.It is added later into reaction kettle
1 part of butyl tin dilaurate.High-speed stirred disperses 1 hour, vacuum defoamation under room temperature.It prepares raw material and is shown in Table 1.
The viscosity of above-mentioned polyurethane adhesive is at 137000-150000cps (25 DEG C).
Embodiment 6: the preparation of light selfreparing polyurethane adhesive (III)
150 parts of optical Response performed polymer (A), 15 parts of Qingdao connection is taken to beautify work TCPP model liquid flame retardants, 80 parts of hydrogen
Aluminium oxide and 5 parts of Anxiang Ai Lite Chemical Co., Ltd. monocycle oxazolidines, stirring at normal temperature 20 minutes.It is added later into reaction kettle
1 part of butyl tin dilaurate.High-speed stirred disperses 1 hour, vacuum defoamation under room temperature.It prepares raw material and is shown in Table 1.
The viscosity of above-mentioned polyurethane adhesive is at 140000-160000cps (25 DEG C).
Embodiment 7: light selfreparing polyurethane adhesive
The present embodiment provides a kind of smooth selfreparing polyurethane adhesives, include the following steps:
1, the preparation of anthracene dimer compound, the preparation method is the same as that of Example 1, relative to main in place of the variation of embodiment 1
Include:
In step (1), the temperature of reaction is 85 DEG C, and the time of reaction is 0.8h；In parts by weight, every 100 parts of 4- is bromo-
N-butyl alcohol needs 150 parts of dihydropyran and 3 parts of catalyst.
In step (2), the temperature of the reaction is 40 DEG C, and the time of reaction is 20h；In parts by weight, every 100 parts of anthrones
Need 250 parts of tetrahydrofurans, 15 parts of sodium hydroxides and 110 parts of step (1) products.
In step (3), the time of irradiation is 15h；In parts by weight, every 100 parts of steps (2) product needs 80 parts of acetic acid
Ethyl ester.
In step (4), the temperature of reaction is 40 DEG C, and the reaction time is 1.5h；Every 100 parts of steps (3) products therefrom
Need 80 parts of methylene chloride and 0.5 part of organotin-phosphate catalyst.
2, the preparation of optical Response performed polymer (C): taking 100 parts of HDI, and the optical Response prepared in 1 part of embodiment 1 is added
3 parts of stannous octoate catalyst is added in chain extender, accelerates to be stirred to react 1 hour at 40 DEG C, vacuum defoamation.
3, the preparation of light selfreparing polyurethane adhesive: raw material is prepared referring to table 1, preparation method is the same as embodiment 4.
Embodiment 8: light selfreparing polyurethane adhesive
The present embodiment provides a kind of smooth selfreparing polyurethane adhesives, include the following steps:
1, the preparation of anthracene dimer compound, the preparation method is the same as that of Example 1, relative to main in place of the variation of embodiment 1
Include:
In step (1), the temperature of reaction is 95 DEG C, and the time of reaction is 1.6h；In parts by weight, every 100 parts of 4- is bromo-
N-butyl alcohol needs 250 parts of dihydropyran and 7 parts of catalyst.
In step (2), the temperature of the reaction is 75 DEG C, and the time of reaction is 28h；In parts by weight, every 100 parts of anthrones
Need 350 parts of tetrahydrofurans, 25 parts of sodium hydroxides and 140 parts of step (1) products.
In step (3), the time of irradiation is 23h；In parts by weight, every 100 parts of steps (2) product needs 130 parts of second
Acetoacetic ester.
In step (4), the temperature of reaction is 55 DEG C, and the reaction time is 2.5h；Every 100 parts of steps (3) products therefrom
Need 130 parts of methylene chloride and 2 parts of organotin-phosphate catalysts.
2, the preparation of optical Response performed polymer (D): taking 100 parts of XDI, and the photoresponse prepared in 10 parts of embodiments 1 is added
Property chain extender, 0.01 part of stannous octoate catalyst is added, accelerates to be stirred to react 5 hours at 80 DEG C, vacuum defoamation.
3, the preparation of light selfreparing polyurethane adhesive: raw material is prepared referring to table 1, preparation method is the same as embodiment 4.
Table 1
Comparative example 1: the preparation of one-component polyurethane (IV)
This comparative example is the comparative example of embodiment 4, relative to the performed polymer in place of the essential difference of embodiment 4 including use
The preparation of difference, the performed polymer of this comparative example includes the following steps:
Take 100 parts of ten thousand magnificent chemistry MDI-100LL model liquefied mdis, the stannous octoate catalyst of 0.1 part of addition, 50 DEG C
Lower acceleration is stirred to react 2 hours, vacuum defoamation.
Take 100 parts of performed polymer, 15 parts of Qingdao connection beautification work TCPP model liquid flame retardants, 80 parts of aluminium hydroxides and 5 parts
Anxiang Ai Lite Chemical Co., Ltd. monocycle oxazolidine, stirring at normal temperature 20 minutes.1 part of two laurels are added into reaction kettle later
Acid butyl tin.High-speed stirred disperses 1 hour, vacuum defoamation under room temperature.
The viscosity of the polyurethane adhesive of this comparative example preparation is at 100000-110000cps (25 DEG C).
Performance test
Its performance is tested after solidifying 168 hours in above-described embodiment 4 to 8 and comparative example polyurethane adhesive, greenhouse, and specific method is such as
Under:
The method of hardness test are as follows: the pocket hardometer penetration hardness test method of GB/T 531-1999 rubber.
It is bonded force test method are as follows: GB/T 13936-1992 vulcanized rubber and metal adhesive tensile shear strength measurement side
Method.
Anti-flammability test method are as follows: GB/24267-2009 flame retardant sealant for building.
Shown in test result is as follows:
Table 2
| Embodiment | Color | Hardness (HD) | It is bonded aluminium sheet intensity (MPa) | Anti-flammability |
| Embodiment 4 | White | 52 | 7.8 | V-0 |
| Embodiment 5 | White | 54 | 8.2 | V-0 |
| Embodiment 6 | White | 54 | 8.7 | V-0 |
| Embodiment 7 | White | 50 | 7.3 | V-0 |
| Embodiment 8 | White | 56 | 8.4 | V-0 |
| Comparative example 1 | White | 52 | 8.0 | V-0 |
Optical Response test method is as follows:
Method one；The glue of above-described embodiment 4 and 1 greenhouse moisture-curable of comparative example after 168 hours is cut into 2mm thickness,
The rectangular blob of viscose of 20mm × 20mm.Blob of viscose is exposed under the ultraviolet light (100w) that wavelength is 254nm and is irradiated 20 minutes, Zhi Houqu
Part blob of viscose tests its hardness out；The part blob of viscose after irradiation is exposed 35 DEG C again again, wavelength is the ultraviolet light (100w) of 365nm
Lower irradiation 20 minutes, tests its hardness.
Method two；It is coated uniformly in transparent PC plate after above-described embodiment 4 and the glue of comparative example 1 are mixed, solidification 168
Hour.The good PC plate of adhesive curing is placed on 35 DEG C, 20 points in the environment irradiated under the ultraviolet light (100w) that wavelength is 254nm
Clock；Test piece after partial illumination later is again placed at 35 DEG C, irradiates 20 minutes under the ultraviolet light (100w) that wavelength is 365nm.
Each stage test piece is taken out respectively to be cut at room temperature by the test method of GB/T13936-1992 adhesive tensile shear strength
Shearing stress test.
Method one is shown in test result is as follows:
Table 3
Method two is shown in test result is as follows:
Table 4
Introducing optical Response chain extender as shown in Table 2 not will cause polyurethane adhesive hardness, adhesive property, flame retardant property etc.
Variation.And table 3 and table 4 then show introduce optical Response chain extender polyurethane adhesive under conditions of ultraviolet lighting, the physical property of glue
The great variety of generation.Specifically, under by 254nm ultraviolet light, the hardness of 4 polyurethane adhesive of embodiment and shearing are strong
Degree is substantially reduced, and compares 1 polyurethane adhesive of comparative example without introducing optical Response crosslinking agent in a short time under ultraviolet lighting
There is not apparent physical property variation.In order to further verify the light reparative potential of polyurethane adhesive, we are compared by 254nm purple
Lower and by 365nm irradiation the properties of sample of outer light irradiation, it is evident that the blob of viscose seen under the ultraviolet light of 365nm again
Hardness and shear strength close to before having restored.This is because reversible decomposition and bonding of the chain extender under different ultraviolet lights,
It is shown below:
After polyurethane adhesive carries out 254nm ultraviolet light when cured, chain extender structures are bonded again, anthracene dimerization
Body becomes two anthracenes, so as to cause polyurethane macromolecular main chain decomposition, and then under causing colloid hardness and shear strength rapid
Drop；When colloid is after the ultraviolet light of 365nm, anthryl group combines form anthracene dimer again, thus colloid hardness and
Shear strength is by being obviously improved.And 1 colloid of comparative example without optical Response chain extender does not have this characteristic then.In order to improve one
Prove this process, the colloid under different irradiations has been carried out infrared test by us, and test spectrogram is shown: ultraviolet by 254nm
After light irradiation, belong to the characteristic absorption peak (1674cm of anthracene dimer-1) disappear；And after again passing by 365nm ultraviolet light, anthracene
Characteristic absorption peak (the 1674cm of dimer-1) occur again.
In order to further verify light self-reparing capability, we are coated uniformly on transparent after mixing the glue of embodiment 4
In PC plate, solidify 168 hours.Shearing test is carried out, is cohesional failure after breaking.It is later that two pieces of PC plate bonding portion splicings are solid
Is carried out 254nm illumination 20 minutes after fixed, is again placed at 35 DEG C later, wavelength under the ultraviolet light (100w) of 365nm respectively according to
Penetrate 10 minutes, 20 minutes, 30 minutes, carry out shearing test after forty minutes, test result is as follows:
Table 5
| 365nm light application time (min) | 10 | 20 | 30 | 40 |
| Shear strength (MPa) | 0.8 | 1.6 | 3.5 | 4.1 |
It is above-mentioned experiments have shown that the polyurethane adhesive of preparation has optical Response, when colloid surface by external environment by breakage,
This colloid first can be subjected to 254nm irradiation, be bonded together to form new complete colloid again using 365nm irradiation, had
Potential light repair function.
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of anthracene dimer compound, which is characterized in that the structural formula of the compound is as follows:
In formula, R is straight chain or branched alkyl.
2. anthracene dimer compound according to claim 1, which is characterized in that R is the straight chained alkyl of C2-C6.
3. anthracene dimer compound according to claim 2, which is characterized in that R is positive butane group.
4. the preparation method of the described in any item anthracene dimer compounds of claims 1 to 3, which is characterized in that the preparation side
Method includes the following steps:
(1) X-R-OH and dihydropyran are reacted under catalyst M, X is halogen；
(2) by anthrone in organic solvent a, reaction product obtained by step (1) is added, alkali is reacted；
(3) reaction product obtained by step (2) is dissolved in organic solvent b, ultraviolet light irradiation；
(4) step (3) products therefrom is dissolved in organic solvent c, catalyst n reaction is added.
5. purposes of the described in any item anthracene dimer compounds of claims 1 to 3 as photoresponse chain extender.
6. a kind of photoresponse performed polymer, which is characterized in that in parts by weight, the raw material for preparing of the photoresponse performed polymer includes:
100 parts of isocyanates, 1-10 parts of photoresponse chain extenders and 0.01-3 parts of catalyst；The photoresponse chain extender is claim 1
To 3 described in any item anthracene dimer compounds.
7. the preparation method of photoresponse performed polymer as claimed in claim 6, which is characterized in that the preparation method includes following step
It is rapid: to take the isocyanates, photoresponse chain extender and catalyst, hybrid reaction.
8. photoresponse performed polymer as claimed in claim 6 is preparing the purposes in light selfreparing polyurethane adhesive.
9. a kind of smooth selfreparing polyurethane adhesive, which is characterized in that in parts by weight, the raw material for preparing of the polyurethane adhesive includes:
80-160 parts of optical Response performed polymer, 1-20 parts of fire retardant, 0.01-5 parts of catalyst, 50-200 parts of inorganic filler and deicer 1-
8 parts；The optical Response performed polymer is photoresponse performed polymer as claimed in claim 6.
10. the preparation method of smooth selfreparing polyurethane adhesive as claimed in claim 9, which is characterized in that the preparation method includes
Following steps: taking the optical Response performed polymer, fire retardant, inorganic filler, deicer, mixes, and the catalyst is added and mixes,
Deaeration.
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| CN113621340A (en) * | 2020-05-07 | 2021-11-09 | 北京化工大学 | Photo-reversible adhesive containing anthracene group and preparation method and application thereof |
| CN113621340B (en) * | 2020-05-07 | 2022-07-05 | 北京化工大学 | Photo-reversible adhesive containing anthracene group and preparation method and application thereof |
| WO2022009513A1 (en) * | 2020-07-08 | 2022-01-13 | 国立大学法人九州大学 | Adhesive material for easy disassembly, cured object, article, and disassembly method |
| JP7005089B1 (en) * | 2020-07-08 | 2022-01-21 | 国立大学法人九州大学 | Easy-to-disassemble adhesive materials, hardened materials, articles and dismantling methods |
| CN113337238A (en) * | 2021-03-24 | 2021-09-03 | 北京化工大学 | High-strength light reversible adhesive, preparation method and application |
| CN117210138A (en) * | 2023-10-10 | 2023-12-12 | 广东光固新材料有限公司 | Reusable acrylate adhesive |
| CN117210138B (en) * | 2023-10-10 | 2024-04-19 | 广东光固新材料有限公司 | Reusable acrylate adhesive |
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