CN116897175A - 用于结构木材粘合的阻燃粘合剂组合物 - Google Patents
用于结构木材粘合的阻燃粘合剂组合物 Download PDFInfo
- Publication number
- CN116897175A CN116897175A CN202280016935.1A CN202280016935A CN116897175A CN 116897175 A CN116897175 A CN 116897175A CN 202280016935 A CN202280016935 A CN 202280016935A CN 116897175 A CN116897175 A CN 116897175A
- Authority
- CN
- China
- Prior art keywords
- adhesive composition
- flame retardant
- polyurethane prepolymer
- retardant adhesive
- och
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 101
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 98
- 239000000853 adhesive Substances 0.000 title claims abstract description 97
- 239000003063 flame retardant Substances 0.000 title claims abstract description 44
- 239000002023 wood Substances 0.000 title claims abstract description 40
- 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 title claims abstract description 34
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 40
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 229920005862 polyol Polymers 0.000 claims description 28
- 150000003077 polyols Chemical group 0.000 claims description 25
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 22
- 229910052698 phosphorus Inorganic materials 0.000 claims description 22
- 239000011574 phosphorus Substances 0.000 claims description 22
- 238000012360 testing method Methods 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 235000021317 phosphate Nutrition 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229920001451 polypropylene glycol Polymers 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- -1 fatty acid isocyanates Chemical class 0.000 description 23
- 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 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 229920000728 polyester Polymers 0.000 description 18
- 239000004814 polyurethane Substances 0.000 description 17
- 229920002635 polyurethane Polymers 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000011120 plywood Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 description 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- LTIKIBFTASQKMM-UHFFFAOYSA-N 1-[bis(4-isocyanatophenyl)methyl]-4-isocyanatobenzene Chemical compound C1=CC(N=C=O)=CC=C1C(C=1C=CC(=CC=1)N=C=O)C1=CC=C(N=C=O)C=C1 LTIKIBFTASQKMM-UHFFFAOYSA-N 0.000 description 2
- KIWZTXBGOICMJQ-UHFFFAOYSA-N 2,4-dimethyl-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CC1COP(C)(=O)O1 KIWZTXBGOICMJQ-UHFFFAOYSA-N 0.000 description 2
- ZXSBYAWLZRAJJY-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde phenol Chemical compound C1(O)=C(C(O)=CC=C1)C=O.OC1=CC=CC=C1 ZXSBYAWLZRAJJY-UHFFFAOYSA-N 0.000 description 2
- UXANWQXYIARNOV-UHFFFAOYSA-N 2-methyl-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CP1(=O)OCCO1 UXANWQXYIARNOV-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 239000004114 Ammonium polyphosphate Substances 0.000 description 2
- 241001070947 Fagus Species 0.000 description 2
- 235000010099 Fagus sylvatica Nutrition 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229920005863 Lupranol® Polymers 0.000 description 2
- 229920005881 Lupranol® 2074 Polymers 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000007706 flame test Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- MHYXPAGFFCSTCJ-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)(C)N=C=O)C(C(C)(N=C=O)C)=CC=C21 MHYXPAGFFCSTCJ-UHFFFAOYSA-N 0.000 description 1
- HUFIHLDYTVSJID-UHFFFAOYSA-N 1,3,5-tris(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC(CN=C=O)=CC(CN=C=O)=C1 HUFIHLDYTVSJID-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- LGLNTUFPPXPHKF-UHFFFAOYSA-N 1,4-diisocyanato-2,3,5,6-tetramethylbenzene Chemical compound CC1=C(C)C(N=C=O)=C(C)C(C)=C1N=C=O LGLNTUFPPXPHKF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 description 1
- MBVGJZDLUQNERS-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-imidazole-4,5-dicarbonitrile Chemical compound FC(F)(F)C1=NC(C#N)=C(C#N)N1 MBVGJZDLUQNERS-UHFFFAOYSA-N 0.000 description 1
- YCZPJMKKVQGGBF-UHFFFAOYSA-N 2-butyl-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCCCP1(=O)OCCO1 YCZPJMKKVQGGBF-UHFFFAOYSA-N 0.000 description 1
- WVFATINBRVAKSW-UHFFFAOYSA-N 2-ethyl-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCP1(=O)OCCO1 WVFATINBRVAKSW-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- VHRHPLFXCDSBAM-UHFFFAOYSA-N 2-propyl-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound CCCP1(=O)OCCO1 VHRHPLFXCDSBAM-UHFFFAOYSA-N 0.000 description 1
- AMUBKBXGFDIMDJ-UHFFFAOYSA-N 3-heptyl-1,2-bis(9-isocyanatononyl)-4-pentylcyclohexane Chemical compound CCCCCCCC1C(CCCCC)CCC(CCCCCCCCCN=C=O)C1CCCCCCCCCN=C=O AMUBKBXGFDIMDJ-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- QXUHBZADGFKYEF-UHFFFAOYSA-N 4,5-bis(hept-1-enyl)-3,6-bis(9-isocyanatononyl)cyclohexene Chemical compound CCCCCC=CC1C(CCCCCCCCCN=C=O)C=CC(CCCCCCCCCN=C=O)C1C=CCCCCC QXUHBZADGFKYEF-UHFFFAOYSA-N 0.000 description 1
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 1
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- KTQUPMJBODMHBB-UHFFFAOYSA-N CON(C1=CC=CC=C1)OC.N=C=O.N=C=O Chemical compound CON(C1=CC=CC=C1)OC.N=C=O.N=C=O KTQUPMJBODMHBB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000004825 One-part adhesive Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 210000001145 finger joint Anatomy 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- HANVTCGOAROXMV-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine;urea Chemical compound O=C.NC(N)=O.NC1=NC(N)=NC(N)=N1 HANVTCGOAROXMV-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- ZEZGGSVFZSKKQT-UHFFFAOYSA-N prop-1-ene;propyl dihydrogen phosphate Chemical compound CC=C.CCCOP(O)(O)=O ZEZGGSVFZSKKQT-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4812—Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—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
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5075—Polyethers having heteroatoms other than oxygen having phosphorus
- C08G18/5081—Polyethers having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/5084—Phosphate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
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
本发明涉及包含反应性聚氨酯预聚物的阻燃粘合剂组合物,特别是单组分阻燃粘合剂组合物,并涉及所述粘合剂组合物用于木质基材的结构粘合的用途。
Description
技术领域
本发明涉及包含反应性聚氨酯预聚物的阻燃粘合剂组合物,特别是单组分阻燃粘合剂组合物,并涉及所述粘合剂组合物用于木质基材的结构粘合的用途。
背景技术
木材粘合剂在当前的工业木结构中扮演着重要的角色。粘合剂可用于建造轻质坚固的结构,并用于缓和木材固有的保湿性带来的膨胀和收缩。工业木材粘合剂是为满足木材工业的需求而定制的,并且在不断发展。
粘合剂在受控条件下用于结构木产品的生产中。这些产品包括指接锯材、胶合木(glulam)、层压原木、交叉层压木材、胶合板和单板层积材。
用于粘合结构木材中的常见粘合剂包括酚基酚醛树脂(PF)、酚-间苯二酚-甲醛(PRF)、间苯二酚-甲醛粘合剂(RF)、氨基树脂基(三聚氰胺-脲-甲醛粘合剂(MUF))、湿固化聚氨酯粘合剂(PU或PUR)和乳液聚合物异氰酸酯粘合剂(EPI)。
其中,单组分聚氨酯粘合剂用于指接物(finger joint)、胶合木、层压原木和交叉层压木材的生产中。这种聚氨酯粘合剂还用于粘合单板层积板材层。这种聚氨酯粘合剂在粘合木质基材时当室温下暴露于水分时会固化并形成硬塑料粘合接头。
然而,聚氨酯粘合剂缺乏耐热性和耐火性,并且由于软化而迅速失去其强度,尽管它们在许多其它方面优于MUF和EPI基粘合剂。如果工程木产品内部的粘合剂在火灾中在高温下软化、分解和燃烧,即使木材部分的完整性保持相对完整,木产品结构也会失效。因此,未来要获得整体性能良好的粘合剂,必须提高用于木质结构中的聚氨酯粘合剂的耐火性能。
已经尝试通过引入液体阻燃剂作为添加剂来提高用于工程木材应用的聚氨酯粘合剂的耐火性。然而,这些阻燃剂或者是降低粘合强度的低分子量增塑剂,或者是由于火灾中产生的有毒气体而让人担忧的卤化阻燃剂。
聚氨酯粘合剂的耐火性也可以通过加入固体阻燃剂来提高,所述固体阻燃剂例如为三水合铝、多磷酸铵、三聚氰胺异氰脲酸酯、硼酸盐等。然而,固体阻燃剂具有破坏粘合剂的流变性能和储存稳定性的缺点,因为在相对低粘性的粘合剂体系中难以防止固体添加剂的沉积。
发明内容
鉴于现有技术中所描述的努力,本发明的目的在于提供一种阻燃的反应性聚氨酯预聚物和包含该预聚物的粘合剂组合物,其可用于粘合木质基材,并且具有改进的耐火性,而不损害粘合剂组合物的粘合性能、粘合耐久性和储存稳定性。
令人惊讶地发现,上述目的通过在结构木材粘合应用中使用包含具有二价膦酸酯或磷酸酯基团的反应性聚氨酯预聚物的阻燃粘合剂组合物而得以实现。
在第一方面,本发明因此涉及包含反应性聚氨酯预聚物的阻燃粘合剂组合物,所述反应性聚氨酯预聚物包含:
至少一个、优选两个或更多个异氰酸酯端基和
至少一个、优选两个或更多个二价膦酸酯或磷酸酯基团,
其中基于所述反应性聚氨酯预聚物的重量,所述反应性聚氨酯预聚物的磷含量大于0.3wt%且小于2.0wt%。
在另一方面,本发明涉及单组分、双组分或多组分聚氨酯粘合剂组合物,其包含根据本发明的反应性聚氨酯预聚物。
在又一方面,本发明涉及一种生产制品的方法,该方法包括将根据本发明的阻燃聚氨酯粘合剂组合物施用到第一基材的表面并将所述第一基材的表面连接到第二基材的表面的步骤,其中至少一个所述表面由木材制成,而且还涉及通过该方法获得的制品。
在又另一方面,本发明涉及根据本发明的阻燃粘合剂组合物或制品在结构粘合中的用途,优选在用于木质材料的结构粘合中的用途。
下面更详细地阐述主题的其它特征和方面。
本领域普通技术人员应当理解,本论述仅是对示例性实施方案的描述,而不旨在限制本发明的较宽方面。
本文中,“包括”或“包含”是指可以添加不影响最终结果的其它步骤和其它成分。该术语涵盖术语“由......组成”和“基本上由......组成”。
除非另有说明,本文中所示的分子量是指数均分子量(Mn)。分子量Mn可基于端基分析(根据DIN 53240-1:2013-06的羟基数或根据EN ISO 11909的NCO含量)或通过根据DIN55672-1:2007-08以THF作为洗脱剂的凝胶渗透色谱(GPC)来确定。除非另有说明,所列分子量是通过GPC测定的那些。重均分子量Mw也可以通过GPC测定,如前所述。
就成分而言,表述“至少一种”指的是成分的类型,而不是分子的绝对数量。“至少一种多元醇”因此意味着例如至少一种类型的多元醇,即可以使用一种类型的多元醇或多种不同多元醇的混合物。与重量数据一起,该表述指的是组合物/混合物中包含的指定类型的所有化合物,也就是说,该组合物不包含超过相应化合物的指定量的这种类型的任何其它化合物。
除非另外明确指出,与本文所述组合物一起列举的所有百分比均指相对于相关混合物的wt.%。
具体实施方式
根据本发明的阻燃粘合剂组合物包含具有至少一个、优选至少两个异氰酸酯端基和至少一个、优选至少两个二价膦酸酯或磷酸酯基团的反应性聚氨酯预聚物。令人惊讶的是,发明人已经发现,如果基于聚氨酯预聚物的重量,反应性聚氨酯预聚物的磷含量在大于0.3wt%且小于2.0wt%的范围内,如通过ICP-MS(电感耦合等离子体质谱)测量的,则包含所述反应性聚氨酯预聚物的粘合剂组合物可以获得改进的耐火性(阻燃性)以及良好的粘合性能、粘合耐久性、储存稳定性和耐热性。
在一个优选实施方案中,基于反应性聚氨酯预聚物的重量,反应性聚氨酯预聚物的磷含量为0.5至1.8wt%,优选为0.7至1.4wt%,特别是0.7至1.1wt%。这种较低量的在预聚物中所包含的磷含量还确保可以减少对来自含有阻燃粘合剂的产品的有机磷的环境担忧。
阻燃的反应性聚氨酯预聚物的结构可以是线性的、支化的或环状的。预聚物包含至少一个异氰酸酯端基、优选两个或更多个异氰酸酯端基。异氰酸酯端基可以与水分或者催化剂如胺或多元醇反应,以使预聚物作为粘合剂固化。在一个实施方案中,异氰酸酯端基是具有两个或更多个、优选三个或更多个异氰酸酯基团的多异氰酸酯的残基。
合适的单体二-或三异氰酸酯选自2,4-和2,6-甲苯二异氰酸酯和这些异构体的任意混合物(TDI)、4,4'-、2,4'-和2,2'-二苯基甲烷二异氰酸酯和这些异构体的任意混合物(MDI)、MDI和MDI同系物的混合物(聚合MDI或PMDI)、脲基甲酸酯改性的二苯基甲烷二异氰酸酯(MDI)、碳二亚胺改性的二苯基甲烷二异氰酸酯(MDI)、脲二酮(uretdione)改性的二苯基甲烷二异氰酸酯(MDI)、1,3-和1,4-亚苯基二异氰酸酯、2,3,5,6-四甲基-1,4-二异氰酸基苯、萘-1,5-二异氰酸酯(NDI)、3,3'-二甲基-4,4'-二异氰酸基联苯(TODI)、联甲氧基苯胺二异氰酸酯(DADI)、1,3,5-三-(异氰酸基甲基)苯、三-(4-异氰酸基苯基)甲烷和三-(4-异氰酸基苯基)硫代磷酸酯、1,4-四亚甲基二异氰酸酯、2-甲基五亚甲基-1,5-二异氰酸酯、1,6-六亚甲基二异氰酸酯(HDI)、2,2,4-和2,4,4-三甲基-1,6-六亚甲基二异氰酸酯(TMDI)、1,10-十亚甲基二异氰酸酯、1,12-十二亚甲基二异氰酸酯、赖氨酸和赖氨酸酯二异氰酸酯、环己烷-1,3-和-1,4-二异氰酸酯、1-甲基-2,4-和-2,6-二异氰酸基环己烷和这些异构体的任意混合物(HTDI或H6TDI)、1-异氰酸基-3,3,5-三甲基-5-异氰酸基甲基环己烷(异佛尔酮二异氰酸酯或IPDI)、全氢-2,4'-和-4,4'-二苯基甲烷二异氰酸酯(HMDI或H12MDI)、1,4-二异氰酸基-2,2,6-三甲基环己烷(TMCDI)、1,3-和1,4-双(异氰酸基甲基)环己烷、间-和对-苯二亚甲基二异氰酸酯(间-和对-XDI)、间-和对-四甲基-1,3-和-1,4-苯二亚甲基二异氰酸酯(间-和对-TMXDI)、双(1-异氰酸基-1-甲基乙基)萘、二聚-和三聚脂肪酸异氰酸酯,例如3,6-双(9-异氰酸基壬基)-4,5-二-(1-庚烯基)环己烯(二聚二异氰酸酯(dimeryl diisocyanate))和α,α,α',α',α″,α″-六甲基-1,3,5-均三甲基苯三异氰酸酯及它们的混合物。
原则上可以使用脂肪族、脂环族或芳香族异氰酸酯,但由于反应性,芳香族多异氰酸酯特别合适。优选的多异氰酸酯的实例是MDI或聚合MDI。
根据本发明,异氰酸酯基封端的聚氨酯预聚物在聚合物链中包含至少一个二价含磷的酯基。二价含磷的酯基团可以是单体的、低聚的或聚合的,并且是单-、双-或更高官能的氨基或羟基官能化的次膦酸酯、膦酸酯、磷酸酯的残基。
在一个实施方案中,二价含磷的酯基团是二价膦酸酯或磷酸酯基团,其各自独立地选自式(1)和(3)
其中n是0至10的平均链长,
R2为CH3、CH2CH3、CH2CH2CH3、CH2(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5、CH2-C6H5、OCH3、OCH2CH3、O(CH2)2CH3、OCH(CH3)2、O(CH2)3CH3、OCH2CH(CH3)2、OC(CH3)3、O-C6H5或O-CH2-C6H5,并且
R1是式(2)的部分,
其中k是1至5的平均链长,
R3和R4相同或不同,并且彼此独立地是H、CH3、CH2CH3、CH2CH2CH3、CH(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5或CH2-C6H5,并且优选是H、CH3、CH2CH3或CH2CH2CH3;
其中f是1至10的平均链长,
R6是CH3、CH2CH3、CH2CH2CH3、CH2(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5或CH2-C6H5;OCH3、OCH2CH3、O(CH2)2CH3、OCH(CH3)2、O(CH2)3CH3、OCH2CH(CH3)2、OC(CH3)3、O-C6H5或O-CH2-C6H5,并且
R5是单键、CH2、CH2CH2、CH2CH2CH2、CH(CH3)2、CH2(CH2)2CH2、CH2CH(CH3)2、C6H4、CH2-C6H4、C(CH3)2-C6H4。
在一个优选实施方案中,二价膦酸酯或磷酸酯基团是以下物质的残基:甲基膦酸乙二醇聚酯、乙基膦酸丙二醇聚酯、丙基膦酸乙二醇聚酯、丁基膦酸乙二醇聚酯、甲基膦酸丙二醇聚酯、乙基膦酸丙二醇聚酯、丙基膦酸丙二醇聚酯、丁基膦酸丙二醇聚酯、甲基磷酸乙二醇聚酯、乙基磷酸丙二醇聚酯、丙基磷酸乙二醇聚酯、丁基磷酸乙二醇聚酯、甲基磷酸丙二醇聚酯、乙基磷酸丙二醇聚酯、丙基磷酸丙二醇聚酯或丁基磷酸丙二醇聚酯。
反应性聚氨酯预聚物还可以包含至少一个不含磷的多元醇的二价残基。
用于制备预聚物的这种多元醇可以是通常用于聚氨酯合成的所有多元醇,例如聚酯多元醇、聚醚多元醇、聚酯醚多元醇、聚碳酸酯多元醇或者它们中两种或更多种的混合物。
聚醚多元醇可以由含有一个或多个伯醇或仲醇基团的多种醇进行制备。作为用于制备不含任何叔氨基的聚醚的引发剂,可以例如使用以下化合物或所述化合物的混合物:水、乙二醇、丙二醇、甘油、丁二醇、丁三醇、三羟甲基乙烷、季戊四醇、己二醇、3-羟基苯酚、己烯三醇、三羟甲基丙烷、辛二醇、新戊二醇、1,4-羟甲基环己烷、双(4-羟基苯基)二甲基甲烷、山梨醇,和芳香族多元醇,如氢醌或萘多元醇。优选使用乙二醇、丙二醇、甘油和三羟甲基丙烷,特别优选使用乙二醇和丙二醇,并且在特别优选的实施方案中,使用丙二醇。
作为用于制备上述聚醚的环状醚,可以使用环氧烷烃,例如环氧乙烷、环氧丙烷、环氧丁烷、环氧氯丙烷、氧化苯乙烯或四氢呋喃或者这些环氧烷烃的混合物。优选使用环氧丙烷、环氧乙烷或四氢呋喃或者它们的混合物。优选使用环氧丙烷或环氧乙烷或者它们的混合物。最特别地优选使用环氧丙烷。
聚酯多元醇可以例如通过使低分子量醇(特别是乙二醇、二甘醇、新戊二醇、己二醇、丁二醇、丙二醇、甘油或三羟甲基丙烷)与己内酯反应来制备。1,4-羟甲基环己烷、2-甲基-1,3-丙二醇、1,2,4-丁三醇、三甘醇、四甘醇、聚乙二醇、二丙二醇、聚丙二醇、二丁二醇和聚丁二醇也适合作为用于制备聚酯多元醇的多官能醇。
其它合适的聚酯多元醇可以通过缩聚来制备。具有不足量的二羧酸或三羧酸或者二羧酸或三羧酸的混合物、或者它们的反应性衍生物的二官能和/或三官能醇可以如此被缩合以形成聚酯多元醇。合适的二羧酸是例如:己二酸或琥珀酸或十二烷二酸及其具有不多于16个碳原子的高级同系物;以及不饱和二羧酸(如马来酸或富马酸)和芳香族二羧酸,特别是异构的苯二甲酸(如邻苯二甲酸、间苯二甲酸或对苯二甲酸)。合适的三羧酸是例如柠檬酸或偏苯三酸。上述酸可以单独使用或者作为它们中两种或更多种的混合物使用。特别合适的醇是己二醇、丁二醇、乙二醇、二甘醇、新戊二醇、3-羟基-2,2-二甲基丙基-3-羟基-2,2-二甲基丙酸酯或三羟甲基丙烷或者它们中两种或更多种的混合物。具有高分子量的聚酯多元醇包括例如:多官能的(优选二官能的)醇——任选与少量三官能的醇一起——和多官能的(优选二官能的)羧酸的反应产物。代替游离聚羧酸,相应的聚羧酸酐或相应的聚羧酸酯也可以(在可能的情况下)与醇(其优选具有1至3个碳原子)一起使用。聚羧酸可以是脂肪族的、脂环族的、芳香族的或杂环的,或者两者兼而有之。它们可以任选地被取代,例如被烷基、烯基、醚基或卤素取代。合适的聚羧酸是例如琥珀酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸、偏苯三酸、邻苯二甲酸酸酐、四氢邻苯二甲酸酸酐、六氢邻苯二甲酸酸酐、四氯邻苯二甲酸酸酐、内亚甲基四氢邻苯二甲酸酸酐、戊二酸酐、马来酸、马来酸酐、富马酸、二聚脂肪酸或三聚脂肪酸或者它们中两种或更多种的混合物。
也可以使用可由内酯(例如基于ε-己内酯的,其也被称为“聚己内酯”)或羟基羧酸(例如ω-羟基己酸)获得的聚酯。
然而,也可以使用油脂化学来源的聚酯多元醇。这种聚酯多元醇可以例如通过以下方式制备:脂肪混合物的环氧化甘油三酯的完全开环,该脂肪混合物包含至少部分烯烃不饱和的脂肪酸并具有一种或多种具有1至12个碳原子的醇;以及随后甘油三酯衍生物的部分酯交换以形成在烷基中具有1至12个碳原子的烷基酯多元醇。
聚碳酸酯多元醇可以例如通过使二醇(例如丙二醇、1,4-丁二醇或1,6-己二醇、二甘醇、三甘醇或四甘醇或者所述二醇的混合物)与碳酸二芳基酯(例如碳酸二苯酯)或碳酰氯反应而获得。
聚氨酯预聚物可以以已知的方式由上述多元醇与多异氰酸酯制备,所述多元醇包括非含磷的多元醇和具有至少一个、优选至少两个羟基的膦酸酯或磷酸酯。含有异氰酸酯基团的预聚物在此可以由多元醇和异氰酸酯制备。在EP-A951493、EP-A1341832、EP-A150444、EP-A1456265和WO 2005/097861中描述了其实例。
在一个实施方案中,阻燃的反应性聚氨酯预聚物可通过使包含以下的化合物反应而获得:
i)多异氰酸酯化合物;
ii)非含磷的多元醇;和
iii)具有至少两个羟基的膦酸酯或磷酸酯。
多异氰酸酯化合物可以是以上描述的那些,优选MDI或聚合MDI。
非含磷的多元醇可以是以上描述的那些,优选聚乙二醇、聚丙二醇或它们的组合。
用于合成预聚物的多元醇的分子量优选为100至20000g/mol,特别是330至4500g/mol。平均官能度可以在2至4.5的范围内。
具有至少两个羟基的膦酸酯或磷酸酯对应于其残基由上述式(1)和(3)表示的那些。
特别优选使用来自Clariant Corporation的市售可得产品Exolit OP 550、Exolit OP 560和Exolit OP 570。
在另一个实施方案中,阻燃的反应性聚氨酯预聚物可通过包括以下步骤的方法制备:
1)提供包含非含磷的多元醇和具有至少两个羟基的膦酸酯或磷酸酯的混合物;和
2)向该混合物中加入多异氰酸酯以获得聚氨酯预聚物。
相应的预聚物通常具有5至25wt.%、优选10至20wt.%的(根据Spielberger,DINEN ISO 11909:2007-05测定的)NCO含量,并且具有1至4、特别是2至3的平均NCO官能度。
预聚物的分子量(Mn)在300至20000g/mol的范围内,优选小于12000g/mol,特别是小于8000g/mol。
聚氨酯预聚物具有根据DIN EN ISO 2555:2000-01在23℃测定的1000至小于10000mPas、优选3500至9000mPas的相对较低的粘度。如果粘度超过上述范围,将难以容易地将预聚物与粘合剂组合物中的添加剂混合,并且粘合剂组合物不能被容易施用。
适合于本发明的粘合剂组合物可以是单组分、双组分或多组分粘合剂组合物,更优选是单组分粘合剂组合物。适合于本发明的聚氨酯粘合剂组合物的交联是基于预聚物中的反应性异氰酸酯基团与H-酸性官能团(例如OH基团、氨基或羧基)的反应的。替代性交联方法包括:NCO基团与来自所施用的粘合剂组合物、基材或环境的水分反应,形成尿素基团。这些交联反应是已知的,它们也可以同时进行。为了加速这种反应,可以在粘合剂中引入催化剂,例如胺、钛或锡催化剂。
在优选实施方案中,聚氨酯粘合剂组合物是单组分聚氨酯粘合剂组合物。这种粘合剂组合物可以包含至少一种NCO-封端的聚氨酯预聚物作为树脂组分,并通过NCO基团与来自所施用的粘合剂组合物、基材或环境的水分反应而固化。
基于粘合剂组合物的总重量,所描述的粘合剂组合物包含例如20至95wt.%、优选50至95wt.%、更优选70至90wt.%的量的上述预聚物。
根据本发明的粘合剂组合物还可以包含添加剂。另外的组分是例如阻燃剂、流平剂、填料、消泡剂、发泡催化剂、荧光增白剂、粘合促进剂、交联剂、颜料、稳定剂、流变改性剂和抗氧化剂。
例如,量不高于2%的已知金属有机和/或胺催化剂(例如,锡、铁、钛或铋的金属有机化合物,如羧酸的锡(II)盐或二烷基锡(IV)羧酸盐)适合作为催化剂。例如,抗氧化剂(例如,市售可得的空间位阻酚和/或硫醚和/或取代的苯并三唑,或HALS类型的空间位阻胺)被用作稳定剂。典型的粘合促进剂是例如乙烯/丙烯酰胺共聚单体、聚合异氰酸酯、反应性有机硅化合物或磷衍生物;含有可水解基团的硅烷也特别合适。同样可以含有少量颜料。总计,添加剂可以以不高于25wt.%的量包含在粘合剂中。
粘合剂组合物可以包含另外的阻燃剂以进一步增加固化的粘合剂的阻燃性。这种阻燃剂可以是本领域公知的含磷阻燃剂。
当本发明中的反应性聚氨酯预聚物具有足够的阻燃性时,不需要含有大量另外的阻燃剂作为粘合剂组合物中反应性聚氨酯预聚物的单独组分。
在一个实施方案中,粘合剂组合物包含按组合物重量计小于5重量%、优选小于1重量%、更优选小于0.1重量%的另外的阻燃剂。在特别实施方案中,阻燃粘合剂组合物不包含另外的阻燃剂。
粘合剂组合物在室温下储存稳定且为液体形式。术语“储存稳定”是指在制备粘合剂组合物并将其保持在室温下90天后目视观察不到相分离。
另一方面,本发明涉及粘合剂组合物的交联/固化产物。交联/固化产物可以通过将粘合剂组合物暴露于水分(对于单组分粘合剂体系而言)或者暴露于合适的多元醇或胺硬化剂(对于双组分粘合剂体系而言)来获得。
粘合剂组合物的交联/固化产物在UL 94燃烧试验(UL 94fire test)中在0.1mm厚度处没有显示出燃烧滴落(burning dripping)。
而且,粘合剂组合物的交联/固化产物显示出大于10MPa的拉伸搭接剪切强度,所述拉伸搭接剪切强度根据EN 302-1:2013在23℃下于重叠250mm2的山毛榉木材上测得。
此外,粘合剂组合物的交联/固化产物表现出根据DIN EN 17224:2019在220℃下测得的与实木相比不低于80%的木材顺纹剪切强度(block shear strength)。
在又一方面,本发明提供了一种用于生产制品的方法,该方法包括将聚氨酯粘合剂组合物施用到第一基材的表面并将所述第一基材的表面连接到第二基材的表面的步骤,其中至少一个所述表面由木材制成。这种基材用于结构木产品的生产中,例如指接锯材、胶合木、层压原木、交叉层压木材、胶合板和单板层积材的生产中。
结合以下实施例将更详细地解释本发明,这些实施例不应被理解为限制本发明的精神。
实施例
材料:
多异氰酸酯:
Desmodur VKS 5是商购自Covestro的二苯基甲烷-4,4'-二异氰酸酯(MDI)与异构体和高官能同系物的混合物。
Desmodur VLR 10是商购自Covestro的基于二苯基甲烷二异氰酸酯(MDI)的芳香族多异氰酸酯。
多元醇:
Lupranol 4002是商购自BASF的环氧乙烷改性的聚丙二醇。
Lupranol 2074是商购自BASF的聚丙二醇。
Desmophen V155是商购自Covestro的胺基三官能聚醚多元醇。
阻燃剂:
Exolit OP550是商购自Clariant的聚合磷酸酯二醇。
Celltech 60是商购自Cellular Technology的2,2-双(氯甲基)三亚甲基双(双(2-氯乙基)磷酸酯)。
Addiflam MHS是商购自CTF2000的涂有硅烷的多磷酸铵。
添加剂:
Efka 3740是商购自BASF的共聚丙烯酸酯基流平剂。
Byk 067A是商购自Byk Chemie的聚硅氧烷基消泡剂。
DMDEE是商购自Evonik的2,2’-二吗啉二乙醚催化剂。
Tinopal OB是商购自BASF的苯并噁唑基荧光增白剂。
试验方法
磷和氯含量:
聚氨酯预聚物中的磷和氯含量通过ICP-MS测量。
粘度:
聚氨酯预聚物的粘度根据DIN EN ISO 2555:2000-01使用Brookfield粘度计RVDV-II(6号转子(spindle),23℃,10pm)测量。
NCO含量:
聚氨酯预聚物的NCO含量根据Spielberger,DIN EN ISO 11909:2007-05测量。
外观:
聚氨酯预聚物的外观是在制备粘合剂组合物后90天目视观察在室温下是形成均匀的液体还是相分离。
结构粘合的木材部件的火焰试验:
样品由用单组分粘合剂组合物粘合的两块木质基材构成。上部基材为3.5x 4x4cm3,下部基材为1x 5x 5cm3。向下钻了一个孔至粘合层的顶部。样品由随后被切割的粘合板制备。在火焰试验之前,将样品在25℃/65%RH储存至少一周。在火焰试验中,将样品放入腔室中并固定在样品架中。充当上部木质元件的镇重物(weight)和防火保护的金属框架被放置在下部件上。组装时间为10min,并将样品以0.6N/mm2的压力压制过夜以进行固化。
将热电偶放入钻孔中用于测量连接处的温度。将第二热电偶放置在火焰顶部周围。将整个组件放置在燃烧器的顶部,并将燃烧器点燃。记录粘合失败的时间和温度。如果粘合失败的时间超过10min,则结果被评价为“合格”,否则其被评价为“不合格”。
UL 94燃烧试验:
对尺寸为12.7cm x 1.5cm且厚度为0.1mm的组装样品根据UL94燃烧试验进行评价。结果被评价为是否有燃烧液滴(burning drip)。
拉伸搭接剪切强度:
对用粘合剂组合物粘合并具有250mm2重叠面积的由山毛榉木材制成的样品根据EN 302-1:2013在23℃进行测试。
木材顺纹剪切强度:
对重叠面积为45x 50mm2的由欧洲云杉(尺寸为45mm x 50mm)制成的样品根据DINEN 17224:2019在220℃进行测试。将与实木相比的值归一化为100%。
预聚物和粘合剂组合物的实施例
在反应容器(1L,来自Juchheim)中,根据表1和2中的配方装入Desmodur V155、VKS5和VLR 10并在搅拌下加入其它成分。将混合物在70℃、真空下搅拌2小时。在达到目标NCO值后,将混合物冷却至室温以获得预聚物(实施例1至3和对比例1至5)。然后,使用高速混合器(来自Hauschild)以2500rpm将根据表3中的配方的添加剂和催化剂混合到预聚物中,以获得粘合剂组合物(AC 1至AC 8)。
阻燃NCO-封端预聚物的磷含量、粘度、NCO含量和外观的测试结果在表1和2中示出。
阻燃性、23℃时的拉伸搭接剪切强度和220℃时的木材顺纹剪切强度的测试结果在表3中示出。
表1.根据本发明的预聚物的配方(重量份数)和测试结果
组分 | 实施例1 | 实施例2 | 实施例3 |
Lupranol 4002 | 20.0 | 19.0 | 19.0 |
Lupranol 2074 | 16.72 | 15.72 | 15.3 |
Exolit OP550 | 4.20 | 6.70 | 8.05 |
Desmophen V155 | 0.25 | 0.25 | 0.25 |
Desmodur VKS 5 | 29.39 | 28.56 | 28.18 |
Desmodur VLR 10 | 29.39 | 29.56 | 28.18 |
P含量(wt%) | 0.70 | 1.10 | 1.40 |
23℃时的粘度(mPas) | 7500 | 6200 | 5800 |
NCO含量(%) | 16.2 | 15.8 | 16.1 |
外观 | 液体 | 液体 | 液体 |
表2.非根据本发明的预聚物的配方(重量份数)和测试结果
表3.粘合剂组合物的配方(重量份数)和测试结果
可以看出,在本发明实施例中制备的具有合适磷量的预聚物表现出阻燃性和作为用于木质材料的结构粘合的粘合剂组合物所需性能(如粘度、储存稳定性和拉伸强度和耐热性)的优异平衡。具有对比例1和2的预聚物的粘合剂组合物由于预聚物中掺入的磷的量较低或没有掺入磷而不能通过火焰试验。具有对比例3的预聚物的粘合剂组合物表现出较差的与木材基材的粘合强度。此外,鉴于粘合剂中存在氯,可能存在环境担忧。具有对比例4的预聚物的粘合剂组合物由于阻燃剂的沉积(segmentation)而出现相分离,因此不能被容易地施用。而且,当在220℃测试木材顺纹剪切强度时,具有来自聚合磷酸酯二醇的磷含量过高的对比例5的预聚物的粘合剂组合物表现出显著增加的粘度和较差的耐热性。
Claims (14)
1.阻燃粘合剂组合物,其包含反应性聚氨酯预聚物,所述反应性聚氨酯预聚物包含:
至少一个异氰酸酯端基和
至少一个二价膦酸酯或磷酸酯基团,
其中基于所述反应性聚氨酯预聚物的重量,所述反应性聚氨酯预聚物的磷含量大于0.3wt%且小于2.0wt%。
2.根据权利要求1所述的阻燃粘合剂组合物,其中所述膦酸酯或磷酸酯基团各自独立地选自式(1)和(3),
其中n是0至10的平均链长,
R2为CH3、CH2CH3、CH2CH2CH3、CH2(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5、CH2-C6H5、OCH3、OCH2CH3、O(CH2)2CH3、OCH(CH3)2、O(CH2)3CH3、OCH2CH(CH3)2、OC(CH3)3、O-C6H5或O-CH2-C6H5,并且
R1是式(2)的部分,
其中k是1至5的平均链长,
R3和R4相同或不同,并且彼此独立地是H、CH3、CH2CH3、CH2CH2CH3、CH(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5或CH2-C6H5,优选H、CH3、CH2CH3或CH2CH2CH3;
其中f是1至10的平均链长,
R6是CH3、CH2CH3、CH2CH2CH3、CH2(CH3)2、CH2(CH2)2CH3、CH2CH(CH3)2、C(CH3)3、C6H5或CH2-C6H5;OCH3、OCH2CH3、O(CH2)2CH3、OCH(CH3)2、O(CH2)3CH3、OCH2CH(CH3)2、OC(CH3)3、O-C6H5或O-CH2-C6H5,并且
R5是单键、CH2、CH2CH2、CH2CH2CH2、CH(CH3)2、CH2(CH2)2CH2、CH2CH(CH3)2、C6H4、CH2-C6H4或C(CH3)2-C6H4。
3.根据权利要求1或2所述的阻燃粘合剂组合物,其中基于所述聚氨酯预聚物的重量,所述聚氨酯预聚物的磷含量为0.5至1.8wt%,优选为0.7至1.4wt%,特别是0.7至1.1wt%。
4.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其中所述聚氨酯预聚物进一步包含至少一个不含磷的多元醇残基。
5.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其中所述聚氨酯预聚物的分子量为300至20000g/mol,优选小于12000g/mol,特别是小于8000g/mol。
6.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其中所述聚氨酯预聚物具有根据DIN EN ISO 2555:2000-01在23℃测定的1000至小于10000mPas、优选为3500至9000mPas的粘度。
7.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其中所述聚氨酯预聚物具有根据Spielberger,DIN EN ISO 11909:2007-05测定的5至25wt.%、优选10至20wt.%的NCO含量。
8.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其中所述聚氨酯预聚物是通过包含以下的组分反应获得的:
i)多异氰酸酯化合物,优选MDI或聚合MDI;
ii)非含磷的多元醇,优选聚丙二醇;以及
iii)具有至少一个羟基的膦酸酯或磷酸酯。
9.根据前述权利要求中任一项所述的阻燃粘合剂组合物,其是单组分、双组分或多组分粘合剂组合物。
10.根据前述权利要求中任一项所述的阻燃粘合剂组合物的固化或交联产物。
11.根据权利要求10所述的固化或交联产物,其中所述产物在UL 94燃烧试验中0.1mm厚度处没有显示出燃烧液滴。
12.根据权利要求10所述的固化或交联产物,其中所述产物表现出大于10MPa的根据EN302-1:2013测定的拉伸搭接剪切强度。
13.生产制品的方法,该方法包括以下步骤:将根据权利要求1至9中任一项所述的阻燃粘合剂组合物施用到第一基材的表面,并将所述第一基材的表面连接到第二基材的表面,其中至少一个所述表面由木材制成。
14.根据权利要求1至9中任一项所述的阻燃粘合剂组合物或根据权利要求12所述的制品在结构粘合中的用途,优选在用于木质材料的结构粘合中的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21159469 | 2021-02-26 | ||
EP21159469.2 | 2021-02-26 | ||
PCT/EP2022/051298 WO2022179772A1 (en) | 2021-02-26 | 2022-01-21 | Flame-retardant adhesive composition for structural wood bonding |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116897175A true CN116897175A (zh) | 2023-10-17 |
Family
ID=74797744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280016935.1A Pending CN116897175A (zh) | 2021-02-26 | 2022-01-21 | 用于结构木材粘合的阻燃粘合剂组合物 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20240150616A1 (zh) |
EP (1) | EP4298141A1 (zh) |
CN (1) | CN116897175A (zh) |
AU (1) | AU2022226294A1 (zh) |
CA (1) | CA3211161A1 (zh) |
WO (1) | WO2022179772A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116102709B (zh) * | 2023-02-23 | 2023-09-15 | 旭川化学(苏州)有限公司 | 一种用于轮胎实芯填充的聚氨酯组合料及其制备方法和应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3401129A1 (de) | 1984-01-14 | 1985-07-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung gemischter polyurethan-prepolymerer |
DE19700014A1 (de) | 1997-01-02 | 1998-07-09 | Henkel Kgaa | Monomerenarmes PU-Prepolymer |
DE10157488A1 (de) | 2000-12-15 | 2002-06-20 | Henkel Kgaa | Polyurethan-Prepolymere mit NCO-Gruppen und niedrigem Gehalt an monomeren Polyisocyanat |
KR20040068953A (ko) | 2001-12-18 | 2004-08-02 | 헨켈 코만디트게젤샤프트 아우프 악티엔 | 낮은 단량체 함량을 갖는 폴리우레탄 예비중합체의 제조방법 |
DE102004018048A1 (de) | 2004-04-08 | 2005-11-10 | Henkel Kgaa | Verfahren zur Herstellung von Polyurethan-Prepolymeren |
DE102013204550A1 (de) * | 2013-03-15 | 2014-09-18 | Evonik Industries Ag | Verwendung von Polyestern mit inhärentem Flammschutz in Kleb- und Dichtstoffen |
CN110105528B (zh) * | 2019-06-03 | 2021-03-16 | 河北科技大学 | 一种无卤阻燃胶及其制备方法 |
CN111808570B (zh) * | 2020-08-27 | 2020-12-04 | 格丽泰新材料科技(苏州)有限公司 | 一种双组份聚氨酯粘合剂及其应用 |
-
2022
- 2022-01-21 CA CA3211161A patent/CA3211161A1/en active Pending
- 2022-01-21 EP EP22701939.5A patent/EP4298141A1/en active Pending
- 2022-01-21 AU AU2022226294A patent/AU2022226294A1/en active Pending
- 2022-01-21 US US18/546,313 patent/US20240150616A1/en active Pending
- 2022-01-21 WO PCT/EP2022/051298 patent/WO2022179772A1/en active Application Filing
- 2022-01-21 CN CN202280016935.1A patent/CN116897175A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
EP4298141A1 (en) | 2024-01-03 |
CA3211161A1 (en) | 2022-09-01 |
WO2022179772A1 (en) | 2022-09-01 |
AU2022226294A1 (en) | 2023-10-12 |
US20240150616A1 (en) | 2024-05-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7199207B2 (en) | Neutral-coloured 1K polyurethane adhesive | |
US11407893B2 (en) | Two-component polyurethane composition with adjustable pot life | |
KR100830384B1 (ko) | 단량체가 없는 반응성 폴리우레탄을 위한 접착 촉진제 | |
JP6404330B2 (ja) | 2剤型ポリウレタン組成物 | |
US11091677B2 (en) | Reactive polyurethane hot melt adhesives containing fillers | |
US9840581B2 (en) | Use of polyesters having inherent flame protection in adhesives and sealants | |
JP2005511873A (ja) | モノマー含有量の少ないポリウレタン−プレポリマーの製造方法 | |
KR101709909B1 (ko) | 우수한 내열성을 갖는 반응성 폴리우레탄 핫멜트 접착제 및 이를 이용한 코팅 원단의 제조방법 | |
MX2007006037A (es) | Adhesivo de poliuretano de dos componentes. | |
JP2013543529A (ja) | ポリアクリレートおよびポリエステルから製造したポリウレタンホットメルト接着剤 | |
KR20230152784A (ko) | 폴리우레탄-기반 결합제 시스템 | |
JP2015110788A (ja) | 改良された耐加水分解性を有する反応性ホットメルト接着剤 | |
US8324299B2 (en) | Moisture-curable hot melt adhesive | |
CN116897175A (zh) | 用于结构木材粘合的阻燃粘合剂组合物 | |
WO2012058806A1 (en) | Two-component polyurethane adhesives with τηiχοtropic effect | |
CN110662781B (zh) | 基于聚氨酯的粘合剂体系 | |
JP2023519546A (ja) | 高度な疎水性及び調節可能なポットライフを有する二成分型ポリウレタン組成物 | |
KR102188218B1 (ko) | 내열성이 우수한 난연형 반응성 폴리우레탄 핫멜트 접착제 및 이를 이용한 코팅 원단의 제조방법 | |
JP2004143314A (ja) | ポリエステルポリエーテルポリオールおよびそれを用いたウレタンプレポリマー | |
KR20190045232A (ko) | 2k 폴리우레탄 접착제를 위한 플라스틱 접착 촉진 | |
JP2016121213A (ja) | 湿気硬化型ポリウレタンホットメルト樹脂組成物、接着剤、及び、積層体 | |
CN112601771B (zh) | 单组分热熔聚氨酯胶粘剂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |