CN109337636A - A kind of one-component polyurethane sealant of rapid link and preparation method thereof - Google Patents
A kind of one-component polyurethane sealant of rapid link and preparation method thereof Download PDFInfo
- Publication number
- CN109337636A CN109337636A CN201811091267.0A CN201811091267A CN109337636A CN 109337636 A CN109337636 A CN 109337636A CN 201811091267 A CN201811091267 A CN 201811091267A CN 109337636 A CN109337636 A CN 109337636A
- Authority
- CN
- China
- Prior art keywords
- parts
- component polyurethane
- polyurethane sealant
- rapid link
- agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000004588 polyurethane sealant Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 229920005862 polyol Polymers 0.000 claims abstract description 44
- 150000003077 polyols Chemical class 0.000 claims abstract description 44
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- 239000012948 isocyanate Substances 0.000 claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 40
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 33
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 33
- 239000004014 plasticizer Substances 0.000 claims abstract description 33
- 229920000570 polyether Polymers 0.000 claims abstract description 33
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 32
- 239000004606 Fillers/Extenders Substances 0.000 claims abstract description 31
- 239000000945 filler Substances 0.000 claims abstract description 30
- 239000004611 light stabiliser Substances 0.000 claims abstract description 29
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 26
- -1 oxazole alkanes Chemical class 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 229940002612 prodrug Drugs 0.000 claims description 28
- 239000000651 prodrug Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 238000010792 warming Methods 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 14
- 229920001451 polypropylene glycol Polymers 0.000 claims description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 12
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 12
- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical group CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 claims description 11
- 239000005711 Benzoic acid Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- 235000010233 benzoic acid Nutrition 0.000 claims description 11
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 10
- 235000012424 soybean oil Nutrition 0.000 claims description 10
- 239000003549 soybean oil Substances 0.000 claims description 10
- 229920001610 polycaprolactone Polymers 0.000 claims description 9
- 239000004632 polycaprolactone Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 239000006229 carbon black Substances 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 8
- 238000006297 dehydration reaction Methods 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- YFRQBLYSYSHFLU-UHFFFAOYSA-N n-ethyl-n-[2-(hydroxyamino)ethyl]hydroxylamine Chemical compound CCN(O)CCNO YFRQBLYSYSHFLU-UHFFFAOYSA-N 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 8
- 239000004417 polycarbonate Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000005292 vacuum distillation Methods 0.000 claims description 8
- SIXWIUJQBBANGK-UHFFFAOYSA-N 4-(4-fluorophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(F)=CC=2)=C1N SIXWIUJQBBANGK-UHFFFAOYSA-N 0.000 claims description 7
- 239000005995 Aluminium silicate Substances 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 241000276489 Merlangius merlangus Species 0.000 claims description 7
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 7
- 235000012211 aluminium silicate Nutrition 0.000 claims description 7
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 7
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 7
- 239000012964 benzotriazole Substances 0.000 claims description 7
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical class C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 claims description 7
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 claims description 7
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 claims description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 7
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 7
- 229940088417 precipitated calcium carbonate Drugs 0.000 claims description 7
- 229960004889 salicylic acid Drugs 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 claims description 7
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 7
- 229960004365 benzoic acid Drugs 0.000 claims description 6
- 229960003424 phenylacetic acid Drugs 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 5
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 claims description 4
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 claims 2
- 235000013312 flour Nutrition 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000001723 curing Methods 0.000 abstract description 38
- 238000000034 method Methods 0.000 abstract description 5
- 238000004132 cross linking Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract description 2
- 238000013008 moisture curing Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 6
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 230000035939 shock Effects 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004591 urethane sealant Substances 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
- C09J175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G18/4829—Polyethers containing at least three hydroxy 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Sealing Material Composition (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses one-component polyurethane sealants of a kind of rapid link and preparation method thereof, it is made of following raw material: 15~36 parts of polyether polyol, 6~18 parts of polyester polyol, 5~15 parts of isocyanates, 15~28 parts of plasticizer, 0.2~1 part of deicer, 20~25 parts of filler, 2~10 parts of resin extender, 0.05~0.7 part of UV light stabilizing agent, 1~5 part of curing accelerator, 0.01~0.15 part and 0.01~0.4 part of catalyst of hydrolytic accelerating agent；Homemade oxazole alkanes curing accelerator is used in polyurethane sealant of the present invention, solves the problems, such as that traditional monocomponent moisture cure system curing rate is slow, bubble is easy in cross-linking process and bi-component alcamines curing system is complicated for operation, working life is short；And the viscosity of polyurethane sealant can be effectively reduced, reduce the dosage of volatile organic solvent, adapt to environmentally protective requirement.
Description
Technical field
The present invention relates to field of adhesive technology, the one-component polyurethane sealant of specifically a kind of rapid link and its
Preparation method.
Background technique
The mode that flow line production is generallyd use in modern automobile industry production, with the quickening of rhythm of production, it is desirable that
Vehicle can rapidly enter next process after installing glass, due to the urethane cures early strength that is bonded for glass compared with
Low, especially the curing rate of sealant is very slow under the conditions of low temperature and low humidity, therefore glass is easy when vehicle moves in a short time
Shake and generate abnormal sound, it is therefore desirable to the curing time of polyurethane sealant abundance to promote adhesive strength, but this
Sample operates the efficiency that will affect the entire production line.
It keeps out the wind according to the regulation of China " automotive safety glass standard GB9656-2003 " when shock accident occurs for vehicle
Glass has to remain on vehicle body, ensures that driver and conductor is not spilled over outside vehicle, the shearing of windshield joint sealant is strong at present
Scale standard is >=4.5MPa, and the criterion of some high-grade bus is above this value, and requirement of individual producers to shear strength is most
High person is even up to 6MPa or more.
To sum up, at present mono-component polyurethane joint sealant have the disadvantage that first is that, one-component polyurethane sealant according to
Rely the moisture-curable in air, the intensity for solidifying early stage is lower；It is cut second is that being stretched in the short time of one-component polyurethane sealant
Shearing stress is lower, and such as 3 hours tensile shear strengths are usually no more than 0.5MPa.
Summary of the invention
To solve the above problems, the object of the present invention is to provide a kind of one-component polyurethane sealant of rapid link and its
Preparation method.
The present invention to achieve the above object, is achieved through the following technical solutions:
A kind of one-component polyurethane sealant of rapid link is made of following raw material in parts by weight: polyether polyol
15~36 parts, 6~18 parts of polyester polyol, 5~15 parts of isocyanates, 15~28 parts of plasticizer, 0.2~1 part of deicer, filler
20~25 parts, 2~10 parts of resin extender, 0.05~0.7 part of UV light stabilizing agent, 1~5 part of curing accelerator, hydrolytic accelerating agent
0.01~0.15 part and 0.01~0.4 part of catalyst；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is more for the two degree of functionality polycaprolactone polyols or polycarbonate of molecular weight 1000~3000
First alcohol；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate
Or one or both of hexamethylene diisocyanate；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, O-phthalic
One or both of sour dinonyl, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite
Or one or both of talcum powder；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- just pungent
Oxygroup benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- dimethylbenzene
Base) in -2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates one
Kind or two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst be dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate,
One or both of diazabicylo, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
Alcamine compound and aldehyde compound, which are added in the reaction vessel containing chloroform, to be dissolved, and the temperature was then adjusted to 40~50 DEG C
Lower reaction 2~3 hours, vacuum distillation removing solvent, is cooled to 20~30 DEG C, obtains pro-drugs；Wherein alcamines
Conjunction object is 2- amino -2- ethyl -1,3- propane diol, 2- amino -1,3- propylene glycol, N, N'- dihydroxy ethyl ethylenediamine or N, N'-
Dihydroxy ethyl -1,3- propane diamine；The aldehyde compound is formaldehyde, benzaldehyde, acetaldehyde or propionic aldehyde；Alcamine compound and aldehydes
The molar ratio of compound is 1:2~4.
Preferably, alcamine compound N, N'- dihydroxy ethyl ethylenediamine or N, N'- dihydroxy ethyl -1,3- propane diamine；Institute
Stating aldehyde compound is acetaldehyde.
Preferably, the hydrolytic accelerating agent is benzoic acid.
Preferably, the plasticizer is epoxidized soybean oil or phenyl alkylsulf.
Preferably, the isocyanates is methyl diphenylene diisocyanate and toluene di-isocyanate(TDI) according to mass ratio 1:
1 ratio is mixed to get.
Preferably, in parts by weight, it is made of following raw material: 20~30 parts of polyether polyol, polyester polyol 10~15
Part, 6~10 parts of isocyanates, 15~20 parts of plasticizer, 0.4~0.8 part of deicer, 22~25 parts of filler, resin extender 4~8
Part, 0.1~0.5 part of UV light stabilizing agent, 3~5 parts of curing accelerator, 0.05~0.12 part of hydrolytic accelerating agent and catalyst 0.1
~0.3 part.
Preferably, the catalyst is dibutyl tin dilaurate.
The invention also includes a kind of preparation methods of the one-component polyurethane sealant of rapid link, including
Following steps:
1. in parts by weight, 15~36 parts of polyether polyol, 6~18 parts of polyester polyol are added in reaction kettle, heating
To 110~130 DEG C, vacuum dehydration 0.5~1 hour under conditions of vacuum degree is not less than 0.095MPa, 55~65 DEG C are cooled to,
5~15 parts of isocyanates are added, are warming up to 75~85 DEG C, keep reaction temperature between 80~90 DEG C, under nitrogen protection instead
It answers 3~5 hours, is cooled to 20~30 DEG C of dischargings, obtains performed polymer；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is more for the two degree of functionality polycaprolactone polyols or polycarbonate of molecular weight 1000~3000
First alcohol；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate
Or one or both of hexamethylene diisocyanate；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 15~28 parts of plasticizer, 0.2~1 part of water removal
Agent, 20~25 parts of fillers and 2~10 parts of resin extenders, are warming up to 60 ± 2 DEG C, keep cutting not less than 10m/s at this temperature
The condition of cutting speed degree, vacuum not less than 0.095MPa stirs 20~30 minutes, is cooled to 40 ± 2 DEG C, continues stirring 20 minutes, adds
Enter 0.05~0.7 part of UV light stabilizing agent, 1~5 part, 0.01~0.15 part hydrolytic accelerating agent of curing accelerator and 0.01~0.4
Part catalyst, is uniformly mixed under conditions of vacuum degree is not less than 0.095MPa, obtains the poly- ammonia of one pack system of rapid link
Ester sealant；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, O-phthalic
One or both of sour dinonyl, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite
Or one or both of talcum powder；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- just pungent
Oxygroup benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- dimethylbenzene
Base) in -2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates one
Kind or two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst be dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate,
One or both of diazabicylo, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine.
The present invention has the advantage that compared with prior art
Homemade oxazole alkanes curing accelerator is used in polyurethane sealant of the present invention, and it is wet solid to solve traditional one pack system
Change system curing rate is slow, bubble is easy in cross-linking process and bi-component alcamines curing system is complicated for operation, working life is short
Problem；And the viscosity of polyurethane sealant can be effectively reduced, reduce the dosage of volatile organic solvent, adapt to environmentally protective
It is required that；The oxazole alkanes curing accelerator that the present invention uses generate on each molecule after hydrolyzing 4 can and isocyanate group
The reactive hydrogen of group's reaction, can react, crosslinking points are more, crosslink density with the isocyanate groups in 4 polyurethane sealants
It is bigger, thus the cross-linked network structure finer and close than existing common oxazolidine hydrolysate is formed, it is poly- so as to increase sharply
The tensile shear strength of urethane sealant；
Curing accelerator and hydrolytic accelerating agent can be used cooperatively in polyurethane sealant of the present invention, and it is cured to play acceleration
Effect, the tensile shear strength of polyurethane sealant is improved rapidly in a short time, polyurethane sealant of the invention is being marked
Solidifying 3 hours shear strengths under the conditions of standard can reach 2MPa or more.
Specific embodiment
The object of the present invention is to provide one-component polyurethane sealant of a kind of rapid link and preparation method thereof, by with
Lower technical solution is realized:
A kind of one-component polyurethane sealant of rapid link is made of following raw material in parts by weight: polyether polyol
15~36 parts, 6~18 parts of polyester polyol, 5~15 parts of isocyanates, 15~28 parts of plasticizer, 0.2~1 part of deicer, filler
20~25 parts, 2~10 parts of resin extender, 0.05~0.7 part of UV light stabilizing agent, 1~5 part of curing accelerator, hydrolytic accelerating agent
0.01~0.15 part and 0.01~0.4 part of catalyst；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is more for the two degree of functionality polycaprolactone polyols or polycarbonate of molecular weight 1000~3000
First alcohol；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate
Or one or both of hexamethylene diisocyanate；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, O-phthalic
One or both of sour dinonyl, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite
Or one or both of talcum powder；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- just pungent
Oxygroup benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- dimethylbenzene
Base) in -2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates one
Kind or two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst be dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate,
One or both of diazabicylo, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
Alcamine compound and aldehyde compound, which are added in the reaction vessel containing chloroform, to be dissolved, and the temperature was then adjusted to 40~50 DEG C
Lower reaction 2~3 hours, vacuum distillation removing solvent, is cooled to 20~30 DEG C, obtains pro-drugs；Wherein alcamines
Conjunction object is 2- amino -2- ethyl -1,3- propane diol, 2- amino -1,3- propylene glycol, N, N'- dihydroxy ethyl ethylenediamine or N, N'-
Dihydroxy ethyl -1,3- propane diamine；The aldehyde compound is formaldehyde, benzaldehyde, acetaldehyde or propionic aldehyde；Alcamine compound and aldehydes
The molar ratio of compound is 1:2~4.
Preferably, alcamine compound N, N'- dihydroxy ethyl ethylenediamine or N, N'- dihydroxy ethyl -1,3- propane diamine；Institute
Stating aldehyde compound is acetaldehyde.
Preferably, the hydrolytic accelerating agent is benzoic acid；Currently preferred hydrolytic accelerating agent can and curing accelerator
It is used cooperatively, accelerates the curing rate of polyurethane sealant, improve crosslink density；
Preferably, the plasticizer is epoxidized soybean oil or phenyl alkylsulf；Currently preferred plasticizer is without neighbour
Phthalic acid ester substance, will not damage the producer and user, more meet safety and environmental protection requirement；
Preferably, the isocyanates is methyl diphenylene diisocyanate and toluene di-isocyanate(TDI) according to mass ratio 1:
1 ratio is mixed to get.
Preferably, in parts by weight, it is made of following raw material: 20~30 parts of polyether polyol, polyester polyol 10~15
Part, 6~10 parts of isocyanates, 15~20 parts of plasticizer, 0.4~0.8 part of deicer, 22~25 parts of filler, resin extender 4~8
Part, 0.1~0.5 part of UV light stabilizing agent, 3~5 parts of curing accelerator, 0.05~0.12 part of hydrolytic accelerating agent and catalyst 0.1
~0.3 part.
Preferably, the catalyst is dibutyl tin dilaurate.
The invention also includes a kind of preparation methods of the one-component polyurethane sealant of rapid link, including
Following steps:
1. in parts by weight, 15~36 parts of polyether polyol, 6~18 parts of polyester polyol are added in reaction kettle, heating
To 110~130 DEG C, vacuum dehydration 0.5~1 hour under conditions of vacuum degree is not less than 0.095MPa, 55~65 DEG C are cooled to,
5~15 parts of isocyanates are added, are warming up to 75~85 DEG C, keep reaction temperature between 80~90 DEG C, under nitrogen protection instead
It answers 3~5 hours, is cooled to 20~30 DEG C of dischargings, obtains performed polymer；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is more for the two degree of functionality polycaprolactone polyols or polycarbonate of molecular weight 1000~3000
First alcohol；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate
Or one or both of hexamethylene diisocyanate；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 15~28 parts of plasticizer, 0.2~1 part of water removal
Agent, 20~25 parts of fillers and 2~10 parts of resin extenders, are warming up to 60 ± 2 DEG C, keep cutting not less than 10m/s at this temperature
The condition of cutting speed degree, vacuum not less than 0.095MPa stirs 20~30 minutes, is cooled to 40 ± 2 DEG C, continues stirring 20 minutes, adds
Enter 0.05~0.7 part of UV light stabilizing agent, 1~5 part, 0.01~0.15 part hydrolytic accelerating agent of curing accelerator and 0.01~0.4
Part catalyst, is uniformly mixed under conditions of vacuum degree is not less than 0.095MPa, obtains the poly- ammonia of one pack system of rapid link
Ester sealant；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, O-phthalic
One or both of sour dinonyl, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite
Or one or both of talcum powder；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- just pungent
Oxygroup benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- dimethylbenzene
Base) in -2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates one
Kind or two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst be dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate,
One or both of diazabicylo, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine.
The synthesis mechanism of the pro-drugs of curing accelerator of the present invention is as follows:
Contain two in the homemade pro-drugs of the present invention it can be seen from the structural formula of above-mentioned pro-drugs
A oxazole ring, the pro-drugs of 1mol are reacted with water generates 4mol reactive hydrogen, can generate more crosslinking points, product is made to exist
Solidification initial stage forms higher crosslink density, and can accelerate this process under the auxiliary of hydrolytic accelerating agent, so that
Polyurethane sealant has excellent fast curing properties, can improve shear strength rapidly in a short time.
Below in conjunction with specific embodiment, the invention will be further described.
Three-functionality-degree polypropylene oxide ether, alias trihydroxy polyethers, is commonly called as glycerin polyether；Original used in the embodiment of the present invention
Expect that the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000 is provided by the big chemical industry in blue star east, model EP-330N.
Embodiment 1
A kind of one-component polyurethane sealant of rapid link, is made of following raw material: polyether polyol 15kg, polyester are more
First alcohol 6kg, isocyanates 5kg, plasticizer 15kg, deicer 0.2kg, filler 20kg, resin extender 2kg, UV light stabilizing agent
0.05kg, curing accelerator 1kg, hydrolytic accelerating agent 0.01kg and catalyst 0.01kg；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is two degree of functionality polycaprolactone polyols of molecular weight 1000~3000；
The isocyanates is methyl diphenylene diisocyanate；
The plasticizer is epoxidized soybean oil；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black；
The resin extender is polyamide；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole；
The hydrolytic accelerating agent is benzoic acid；
The catalyst is dibutyl tin dilaurate；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
1.19kg 2- amino -2- ethyl -1,3- propane diol and 0.6kg formaldehyde, which are added in the reaction vessel containing chloroform, to be dissolved,
The temperature was then adjusted to reacting 2 hours at 40 DEG C, vacuum distillation removing solvent is cooled to 20 DEG C, obtains pro-drugs.
Embodiment 2
A kind of one-component polyurethane sealant of rapid link, is made of following raw material: polyether polyol 36kg, polyester are more
First alcohol 18kg, isocyanates 15kg, plasticizer 28kg, deicer 1kg, filler 25kg, resin extender 10kg, UV light stabilizing agent
0.7kg, curing accelerator 5kg, hydrolytic accelerating agent 0.15kg and catalyst 0.4kg；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is two degree of functionality polycarbonate polyols of molecular weight 1000~3000；
The isocyanates is toluene di-isocyanate(TDI)；
The plasticizer is dipropylene glycol dibenzoate；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is gas-phase silica；
The resin extender is PVC paste resin；
The UV light stabilizing agent is 2-hydroxy-4-n-octoxybenzophenone；
The hydrolytic accelerating agent is salicylic acid；
The catalyst is dibutyltin dichloride；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
9.1kg 2- amino-1,3-propanediol and 42.4kg benzaldehyde, which are added in the reaction vessel containing chloroform, to be dissolved, by temperature
It is adjusted at 50 DEG C and reacts 3 hours, vacuum distillation removing solvent is cooled to 30 DEG C, obtains pro-drugs.
Embodiment 3
A kind of one-component polyurethane sealant of rapid link, is made of following raw material: polyether polyol 20kg, polyester are more
First alcohol 15kg, isocyanates 10kg, plasticizer 18kg, deicer 0.4kg, filler 22kg, resin extender 4kg, ultraviolet light stabilized
Agent 0.1kg, curing accelerator 3kg, hydrolytic accelerating agent 0.05kg and catalyst 0.1kg；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is two degree of functionality polycaprolactone polyols of molecular weight 1000~3000；
The isocyanates is that isophorone diisocyanate and hexamethylene diisocyanate are mixed according to mass ratio 1:1
It obtains；
The plasticizer is that diisooctyl phthalate and diisononyl phthalate are mixed according to mass ratio 1:2
It arrives；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is that precipitated calcium carbonate and kaolin are mixed to get according to mass ratio 5:6；
The resin extender is polyamide；
The UV light stabilizing agent is 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole and 2- [2,4-
Bis- (2,4- xylyl) -2- (cyanuro 1,3,5) 5- phenol octyloxies are mixed to get according to mass ratio 1:1；
The hydrolytic accelerating agent is benzene sulfonic acid；
The catalyst is that dibutyltin diacetate and diazabicylo are mixed to get according to mass ratio 1:1；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
2.96kg N, N'- dihydroxy ethyl ethylenediamine and 2.64kg acetaldehyde, which are added in the reaction vessel containing chloroform, to be dissolved, by temperature
It is adjusted at 42 DEG C and reacts 2.5 hours, vacuum distillation removing solvent is cooled to 28 DEG C, obtains pro-drugs.
Embodiment 4
A kind of one-component polyurethane sealant of rapid link, is made of following raw material: polyether polyol 30kg, polyester are more
First alcohol 15kg, isocyanates 10kg, plasticizer 20kg, deicer 0.8kg, filler 25kg, resin extender 8kg, ultraviolet light stabilized
Agent 0.5kg, curing accelerator 5kg, hydrolytic accelerating agent 0.12kg and catalyst 0.3kg；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is two degree of functionality polycarbonate polyols of molecular weight 1000~3000；
The isocyanates is that methyl diphenylene diisocyanate and hexamethylene diisocyanate are mixed according to mass ratio 1:1
Conjunction obtains；
The plasticizer is dioctyl phthalate；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is that powdered whiting and organobentonite are mixed to get according to 1:4；
The resin extender is PVC paste resin；
The UV light stabilizing agent is 2- [2,4- bis- (2,4- xylyls) -2- (cyanuro 1,3,5) 5- octyloxy benzene
Phenol；
The hydrolytic accelerating agent is acetic acid；
The catalyst is that double morpholine Anaesthetie Ethers and triethylamine are mixed to get according to mass ratio 1:1；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
3.24kg N, N'- dihydroxy ethyl -1,3- propane diamine and 2.90kg propionic aldehyde, which are added in the reaction vessel containing chloroform, to be dissolved,
The temperature was then adjusted to reacting 2 hours at 48 DEG C, vacuum distillation removing solvent is cooled to 25 DEG C, obtains pro-drugs.
Embodiment 5
A kind of one-component polyurethane sealant of rapid link, is made of following raw material: polyether polyol 25kg, polyester are more
First alcohol 14kg, isocyanates 8kg, plasticizer 18kg, deicer 0.6kg, filler 24kg, resin extender 6kg, UV light stabilizing agent
0.3kg, curing accelerator 4kg, hydrolytic accelerating agent 0.10kg and catalyst 0.2kg；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is two degree of functionality polycaprolactone polyols of molecular weight 1000~3000；
The isocyanates is hexamethylene diisocyanate；
The plasticizer is phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is that acetylene carbon black and talcum powder are mixed to get according to mass ratio 1:1；
The resin extender is PVC paste resin；
The UV light stabilizing agent is bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates；
The hydrolytic accelerating agent is benzoic acid；
The catalyst is that stannous octoate and double morpholine Anaesthetie Ethers are mixed to get according to mass ratio 1:1；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: will
2.22kg N, N'- dihydroxy ethyl ethylenediamine and 3.04kg propionic aldehyde, which are added in the reaction vessel containing chloroform, to be dissolved, by temperature
It is adjusted at 45 DEG C and reacts 2.5 hours, vacuum distillation removing solvent is cooled to 25 DEG C, obtains pro-drugs.
Embodiment 6
The preparation method of the one-component polyurethane sealant of rapid link described in embodiment 1, comprising the following steps:
1. 15kg polyether polyol, 6kg polyester polyol are added in reaction kettle, 110 DEG C are warming up to, it is not low in vacuum degree
Vacuum dehydration 0.5 hour under conditions of 0.095MPa is cooled to 55 DEG C, and 5kg isocyanates is added, and is warming up to 75 DEG C, keeps
Reaction temperature reacts 3 hours under nitrogen protection at 80 DEG C, is cooled to 20 DEG C of dischargings, obtains performed polymer；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 15kg plasticizer, 0.2kg deicer, 20kg
Filler and 2kg resin extender, are warming up to 58 DEG C, keep shear velocity, vacuum not less than 10m/s to be not less than at this temperature
The condition of 0.095MPa stirs 20 minutes, is cooled to 38 DEG C, continues stirring 20 minutes, and 0.05kg UV light stabilizing agent, 1kg is added
Curing accelerator, 0.01kg hydrolytic accelerating agent and 0.01kg catalyst stir under conditions of vacuum degree is not less than 0.095MPa
It is uniformly mixed, obtains the one-component polyurethane sealant of rapid link.
Embodiment 7
The preparation method of the one-component polyurethane sealant of rapid link as described in example 2, comprising the following steps:
1. by 36kg polyether polyol, 18kg polyester polyol be added reaction kettle in, be warming up to 130 DEG C, vacuum degree not
Lower than vacuum dehydration 1 hour under conditions of 0.095MPa, 65 DEG C are cooled to, 15kg isocyanates is added, is warming up to 85 DEG C, is kept
Reaction temperature reacts 5 hours under nitrogen protection at 90 DEG C, is cooled to 30 DEG C of dischargings, obtains performed polymer；
2. by step, 1. gained performed polymer is added in blender, is sequentially added 28kg plasticizer, 1kg deicer, 25kg and is filled out
Material and 10kg resin extender, are warming up to 62 DEG C, keep shear velocity, vacuum not less than 10m/s to be not less than at this temperature
The condition of 0.095MPa stirs 30 minutes, is cooled to 42 DEG C, continues stirring 20 minutes, and 0.7kg UV light stabilizing agent, 5kg is added
Curing accelerator, 0.15kg hydrolytic accelerating agent and 0.4kg catalyst, stirring is mixed under conditions of vacuum degree is not less than 0.095MPa
It closes uniformly, obtains the one-component polyurethane sealant of rapid link.
Embodiment 8
The preparation method of the one-component polyurethane sealant of rapid link described in embodiment 3, comprising the following steps:
1. by 20kg polyether polyol, 15kg polyester polyol be added reaction kettle in, be warming up to 115 DEG C, vacuum degree not
Lower than vacuum dehydration 45 minutes under conditions of 0.095MPa, 58 DEG C are cooled to, 10kg isocyanates is added, is warming up to 78 DEG C, is protected
Reaction temperature is held at 82 DEG C, is reacted 3.5 hours under nitrogen protection, is cooled to 24 DEG C of dischargings, obtains performed polymer；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 18kg plasticizer, 0.4kg deicer, 22kg
Filler and 4kg resin extender, are warming up to 60 DEG C, keep shear velocity, vacuum not less than 10m/s to be not less than at this temperature
The condition of 0.095MPa stirs 25 minutes, is cooled to 40 DEG C, continues stirring 20 minutes, and 0.1kg UV light stabilizing agent, 3kg is added
Curing accelerator, 0.05kg hydrolytic accelerating agent and 0.1kg catalyst, stirring is mixed under conditions of vacuum degree is not less than 0.095MPa
It closes uniformly, obtains the one-component polyurethane sealant of rapid link.
Embodiment 9
The preparation method of the one-component polyurethane sealant of rapid link as described in example 4, comprising the following steps:
1. by 30kg polyether polyol, 15kg polyester polyol be added reaction kettle in, be warming up to 125 DEG C, vacuum degree not
Lower than vacuum dehydration 50 minutes under conditions of 0.095MPa, 62 DEG C are cooled to, 10kg isocyanates is added, is warming up to 82 DEG C, is protected
Reaction temperature is held at 86 DEG C, is reacted 4 hours under nitrogen protection, is cooled to 28 DEG C of dischargings, obtains performed polymer；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 20kg plasticizer, 0.8kg deicer, 25kg
Filler and 8kg resin extender, are warming up to 61 DEG C, keep shear velocity, vacuum not less than 10m/s to be not less than at this temperature
The condition of 0.095MPa stirs 28 minutes, is cooled to 41 DEG C, continues stirring 20 minutes, and 0.5kg UV light stabilizing agent, 5kg is added
Curing accelerator, 0.12kg hydrolytic accelerating agent and 0.3kg catalyst, stirring is mixed under conditions of vacuum degree is not less than 0.095MPa
It closes uniformly, obtains the one-component polyurethane sealant of rapid link.
Embodiment 10
The preparation method of the one-component polyurethane sealant of rapid link described in embodiment 5, comprising the following steps:
1. by 25kg polyether polyol, 14kg polyester polyol be added reaction kettle in, be warming up to 120 DEG C, vacuum degree not
Lower than vacuum dehydration 1 hour under conditions of 0.095MPa, 60 DEG C are cooled to, 8kg isocyanates is added, is warming up to 80 DEG C, is kept
Reaction temperature reacts 4 hours under nitrogen protection between 85 DEG C, is cooled to 25 DEG C of dischargings, obtains performed polymer；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 18kg plasticizer, 0.6kg deicer, 24kg
Filler and 6kg resin extender, are warming up to 60 DEG C, keep shear velocity, vacuum not less than 10m/s to be not less than at this temperature
The condition of 0.095MPa stirs 20~30 minutes, is cooled to 40 DEG C, continues to stir 20 minutes, addition 0.3kg UV light stabilizing agent,
4kg curing accelerator, 0.10kg hydrolytic accelerating agent and 0.2kg catalyst stir under conditions of vacuum degree is not less than 0.095MPa
It mixes uniformly mixed, obtains the one-component polyurethane sealant of rapid link.
Mechanics properties testing:
Test piece (parallel 2 parts of preparation) is made in the gluing under standard laboratory temperature, and laboratory condition is according to GB/T 2941-
2006 execute, and test piece is tested respectively after placing 3 hours and placing 7 days.
Tensile strength and elongation at break are executed according to GB/T 528-2009；
Shear strength is executed according to GB/T 7124-2008, and test piece is to use the processed rigid metal sheet of silane coupling agent in advance；
Tearing strength is executed according to GB/T 529-2008,
Testing result is shown in Table 1.
The testing result statistical form of 1 embodiment 6~10 of table
It can be seen from the data of table 1 polyurethane sealant of the rapid link of the application can in a short time have compared with
High tensile shear strength has quick-setting performance.
Claims (8)
1. a kind of one-component polyurethane sealant of rapid link, it is characterised in that: in parts by weight, be made of following raw material:
15~36 parts of polyether polyol, 6~18 parts of polyester polyol, 5~15 parts of isocyanates, 15~28 parts of plasticizer, deicer 0.2
~1 part, 20~25 parts of filler, 2~10 parts of resin extender, 0.05~0.7 part of UV light stabilizing agent, 1~5 part of curing accelerator,
0.01~0.15 part and 0.01~0.4 part of catalyst of hydrolytic accelerating agent；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is the two degree of functionality polycaprolactone polyols or polycarbonate polyol of molecular weight 1000~3000；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate or six
One or both of methylene diisocyanate；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, phthalic acid two
One or both of different nonyl ester, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite or cunning
One or both of mountain flour；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- n-octyloxy
Benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- xylyls) -
One of 2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates or
Two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst is dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate, phenodiazine
One or both of miscellaneous two ring, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine；
The curing accelerator is pro-drugs；The pro-drugs are obtained according to following preparation step: by hydramine
Class compound and aldehyde compound, which are added in the reaction vessel containing chloroform, to be dissolved, and the temperature was then adjusted to anti-at 40~50 DEG C
It answers 2~3 hours, vacuum distillation removing solvent is cooled to 20~30 DEG C, obtains pro-drugs；Wherein alcamine compound
For 2- amino -2- ethyl -1,3- propane diol, 2- amino -1,3- propylene glycol, N, N'- dihydroxy ethyl ethylenediamine or N, N'- dihydroxy
Ethyl -1,3- propane diamine；The aldehyde compound is formaldehyde, benzaldehyde, acetaldehyde or propionic aldehyde；Alcamine compound and aldehydes chemical combination
The molar ratio of object is 1:2~4.
2. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: alcamines
Conjunction object is N, N'- dihydroxy ethyl ethylenediamine or N, N'- dihydroxy ethyl -1,3- propane diamine；The aldehyde compound is acetaldehyde.
3. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: the hydrolysis
Promotor is benzoic acid.
4. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: the plasticising
Agent is epoxidized soybean oil or phenyl alkylsulf.
5. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: the isocyanide
Acid esters is that methyl diphenylene diisocyanate and toluene di-isocyanate(TDI) are mixed to get according to the ratio of mass ratio 1:1.
6. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: with parts by weight
Meter, is made of following raw material: 20~30 parts of polyether polyol, 10~15 parts of polyester polyol, and 6~10 parts of isocyanates, plasticising
15~20 parts of agent, 0.4~0.8 part of deicer, 22~25 parts of filler, 4~8 parts of resin extender, UV light stabilizing agent 0.1~0.5
Part, 3~5 parts of curing accelerator, 0.05~0.12 part and 0.1~0.3 part of catalyst of hydrolytic accelerating agent.
7. a kind of one-component polyurethane sealant of rapid link according to claim 1, it is characterised in that: the catalysis
Agent is dibutyl tin dilaurate.
8. a kind of preparation method of the one-component polyurethane sealant of rapid link described in claim 1, it is characterised in that: packet
Include following steps:
1. in parts by weight, 15~36 parts of polyether polyol, 6~18 parts of polyester polyol are added in reaction kettle, it is warming up to 110
~130 DEG C, vacuum dehydration 0.5~1 hour under conditions of vacuum degree is not less than 0.095MPa, 55~65 DEG C are cooled to, is added 5
~15 parts of isocyanates are warming up to 75~85 DEG C, keep reaction temperature between 80~90 DEG C, react 3~5 under nitrogen protection
Hour, 20~30 DEG C of dischargings are cooled to, performed polymer is obtained；
Wherein polyether polyol is the three-functionality-degree polypropylene oxide ether of molecular weight 3000~6000；
The polyester polyol is the two degree of functionality polycaprolactone polyols or polycarbonate polyol of molecular weight 1000~3000；
The isocyanates is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone diisocyanate or six
One or both of methylene diisocyanate；
2. by step, 1. gained performed polymer is added in blender, sequentially adds 15~28 parts of plasticizer, 0.2~1 part of deicer, 20
~25 parts of fillers and 2~10 parts of resin extenders, are warming up to 60 ± 2 DEG C, keep the shearing speed not less than 10m/s at this temperature
The condition of degree, vacuum not less than 0.095MPa stirs 20~30 minutes, is cooled to 40 ± 2 DEG C, continues stirring 20 minutes, is added
0.05~0.7 part of UV light stabilizing agent, 1~5 part, 0.01~0.15 part hydrolytic accelerating agent of curing accelerator and 0.01~0.4 part
Catalyst is uniformly mixed under conditions of vacuum degree is not less than 0.095MPa, obtains the mono-component polyurethane of rapid link
Sealant；
The plasticizer is epoxidized soybean oil, dipropylene glycol dibenzoate, diisooctyl phthalate, phthalic acid two
One or both of different nonyl ester, dioctyl phthalate, BBP(Butyl Benzyl Phthalate or phenyl alkylsulf；
The deicer is p-Methyl benzenesulfonyl isocyanate；
The filler is acetylene carbon black, gas-phase silica, precipitated calcium carbonate, powdered whiting, kaolin, organobentonite or cunning
One or both of mountain flour；
The resin extender is polyamide or PVC paste resin；
The UV light stabilizing agent is 2- (2 '-hydroxyls -3 ', 5 '-diamyl phenyl) benzotriazole, 2- hydroxyl -4- n-octyloxy
Benzophenone, 2- (the tertiary base phenyl of bis- fourth of 2- hydroxyl -3,5-) -5- chlorinated benzotriazole, 2- [2,4- bis- (2,4- xylyls) -
One of 2- (cyanuro 1,3,5) 5- phenol octyloxy or bis- (1,2,2,6,6- pentamethyl -4- piperidyl) sebacates or
Two kinds；
The hydrolytic accelerating agent is benzoic acid, salicylic acid, benzene sulfonic acid or acetic acid；
The catalyst is dibutyl tin dilaurate, dibutyltin dichloride, dibutyltin diacetate, stannous octoate, phenodiazine
One or both of miscellaneous two ring, triethylene diamine, double morpholine Anaesthetie Ethers or triethylamine.
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| CN111087963A (en) * | 2019-12-27 | 2020-05-01 | 江苏乘鹰新材料股份有限公司 | Single-component solvent-free moisture-curing adhesive for compounding cigarette paperboard |
| CN111303827A (en) * | 2020-03-31 | 2020-06-19 | 烟台德邦科技有限公司 | UV-moisture dual-curing polyurethane sealant and preparation method thereof |
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| CN111808569A (en) * | 2020-07-24 | 2020-10-23 | 山东北方现代化学工业有限公司 | Damp and heat resistant high-strength single-component polyurethane primer-free adhesive sealant and preparation method thereof |
| CN111808569B (en) * | 2020-07-24 | 2021-11-23 | 山东北方现代化学工业有限公司 | Damp and heat resistant high-strength single-component polyurethane primer-free adhesive sealant and preparation method thereof |
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| EP4284887A4 (en) * | 2021-01-28 | 2024-11-27 | Henkel AG & Co. KGaA | Process of incorporating gelling and phase separation inhibitor into a filled polyurethane reactive hot melt adhesive |
| CN114058310B (en) * | 2021-11-08 | 2023-03-24 | 南京南溧新材料有限公司 | Bio-based MS adhesive and preparation method thereof |
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| CN114605953A (en) * | 2022-01-27 | 2022-06-10 | 北京东方雨虹防水技术股份有限公司 | Polyurethane sealant |
| CN114605953B (en) * | 2022-01-27 | 2024-04-23 | 北京东方雨虹防水技术股份有限公司 | Polyurethane sealant |
| CN115785850B (en) * | 2022-11-30 | 2024-05-28 | 成都硅宝科技股份有限公司 | Adhesion promoter, preparation method and application thereof, and waterproof adhesive single-component polyurethane sealant, and preparation method and application thereof |
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