DE10229519A1 - Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten - Google Patents
Reaktive Polyurethane mit einem geringen Gehalt an monomeren DiisocyanatenInfo
- Publication number
- DE10229519A1 DE10229519A1 DE10229519A DE10229519A DE10229519A1 DE 10229519 A1 DE10229519 A1 DE 10229519A1 DE 10229519 A DE10229519 A DE 10229519A DE 10229519 A DE10229519 A DE 10229519A DE 10229519 A1 DE10229519 A1 DE 10229519A1
- Authority
- DE
- Germany
- Prior art keywords
- reactive
- diisocyanate
- mol
- mdi
- acid
- 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.)
- Withdrawn
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 88
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 84
- 125000005442 diisocyanate group Chemical group 0.000 title claims abstract description 72
- 150000002009 diols Chemical class 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000000178 monomer Substances 0.000 title abstract description 22
- 239000013466 adhesive and sealant Substances 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 47
- -1 B. tin-II-acetate Chemical class 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000853 adhesive Substances 0.000 claims description 22
- 230000001070 adhesive effect Effects 0.000 claims description 22
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000565 sealant Substances 0.000 claims description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 15
- 239000006260 foam Substances 0.000 claims description 14
- 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 10
- 239000004831 Hot glue Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 238000005266 casting Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000011135 tin Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052797 bismuth Inorganic materials 0.000 claims description 4
- 239000012939 laminating adhesive Substances 0.000 claims description 4
- 239000011133 lead Substances 0.000 claims description 4
- 150000002902 organometallic compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000009419 refurbishment Methods 0.000 claims description 4
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 3
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 claims description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 2
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical class CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 claims description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 abstract description 11
- 150000002513 isocyanates Chemical class 0.000 abstract description 10
- 238000012545 processing Methods 0.000 abstract description 8
- 238000000746 purification Methods 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 description 36
- 150000003077 polyols Chemical class 0.000 description 35
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000005056 polyisocyanate Substances 0.000 description 10
- 229920001228 polyisocyanate Polymers 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000004823 Reactive adhesive Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000004848 polyfunctional curative Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000007789 sealing Methods 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
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AUJDNBNEWGSLMQ-UHFFFAOYSA-N bis(3-methoxy-3-oxopropyl)tin Chemical compound COC(=O)CC[Sn]CCC(=O)OC AUJDNBNEWGSLMQ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical class O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- SIKLBQUNDVFDSP-UHFFFAOYSA-N n,n-diethyl-3-morpholin-4-ylpropan-1-amine Chemical compound CCN(CC)CCCN1CCOCC1 SIKLBQUNDVFDSP-UHFFFAOYSA-N 0.000 description 1
- WOVGPTWDVHNCLE-UHFFFAOYSA-N n,n-dimethyl-3-morpholin-4-ylpropan-1-amine Chemical compound CN(C)CCCN1CCOCC1 WOVGPTWDVHNCLE-UHFFFAOYSA-N 0.000 description 1
- BPJSFKWPIOFKPW-UHFFFAOYSA-N n-ethyl-3-morpholin-4-yl-n-(3-morpholin-4-ylpropyl)propan-1-amine Chemical compound C1COCCN1CCCN(CC)CCCN1CCOCC1 BPJSFKWPIOFKPW-UHFFFAOYSA-N 0.000 description 1
- UZSBXLQQPOUQKT-UHFFFAOYSA-N n-methyl-3-morpholin-4-yl-n-(3-morpholin-4-ylpropyl)propan-1-amine Chemical compound C1COCCN1CCCN(C)CCCN1CCOCC1 UZSBXLQQPOUQKT-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical class [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XATCWUIVPWOLDP-UHFFFAOYSA-N trioctyl(trioctylstannyloxy)stannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)O[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC XATCWUIVPWOLDP-UHFFFAOYSA-N 0.000 description 1
- XMHKTINRBAKEDS-UHFFFAOYSA-N trioctyltin Chemical compound CCCCCCCC[Sn](CCCCCCCC)CCCCCCCC XMHKTINRBAKEDS-UHFFFAOYSA-N 0.000 description 1
- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-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
- 239000003981 vehicle Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10229519A DE10229519A1 (de) | 2001-07-10 | 2002-07-02 | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10132571 | 2001-07-10 | ||
| DE10229519A DE10229519A1 (de) | 2001-07-10 | 2002-07-02 | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10229519A1 true DE10229519A1 (de) | 2003-01-30 |
Family
ID=7690688
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10229519A Withdrawn DE10229519A1 (de) | 2001-07-10 | 2002-07-02 | Reaktive Polyurethane mit einem geringen Gehalt an monomeren Diisocyanaten |
| DE50214182T Expired - Lifetime DE50214182D1 (de) | 2001-07-10 | 2002-07-03 | Reaktive polyurethane mit einem geringen gehalt an monomeren diisocyanaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50214182T Expired - Lifetime DE50214182D1 (de) | 2001-07-10 | 2002-07-03 | Reaktive polyurethane mit einem geringen gehalt an monomeren diisocyanaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20040162385A1 (https=) |
| EP (1) | EP1404733B1 (https=) |
| JP (2) | JP4317446B2 (https=) |
| AT (1) | ATE455810T1 (https=) |
| CA (1) | CA2453511C (https=) |
| DE (2) | DE10229519A1 (https=) |
| WO (1) | WO2003006521A1 (https=) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10260974A1 (de) * | 2002-12-24 | 2004-07-15 | Fischerwerke Artur Fischer Gmbh & Co. Kg | Spezialmörtel für Mehrkomponentensysteme |
| DE10358667A1 (de) * | 2003-12-12 | 2005-07-14 | Votteler Lackfabrik Gmbh & Co. Kg | Mittel zur Isoliergrundierung von Holz und Holzwerkstoffen und dessen Verwendung |
| DE102004018048A1 (de) * | 2004-04-08 | 2005-11-10 | Henkel Kgaa | Verfahren zur Herstellung von Polyurethan-Prepolymeren |
| DE102004057292A1 (de) * | 2004-11-26 | 2006-06-01 | Klebchemie, M.G. Becker Gmbh & Co Kg | Verfahren zur Herstellung von reaktiven Polyurethanzusammensetzungen |
| DE102008025793A1 (de) * | 2008-05-29 | 2009-12-03 | Henkel Ag & Co. Kgaa | Reaktive Klebstoffe mit sehr geringem Gehalt an monomeren Diisocyanaten |
| DE102008027914A1 (de) * | 2008-06-12 | 2009-12-17 | Henkel Ag & Co. Kgaa | Vernetzende 2K-Isocyanat-Zusammensetzungen |
| DE102009033637A1 (de) | 2009-07-17 | 2011-01-20 | Bayer Materialscience Ag | Prepolymere |
| US9637667B2 (en) | 2001-10-13 | 2017-05-02 | Henkel Ag & Co. Kgaa | Reactive polyurethane compositions with a low residual monomer content |
| EP3450476A1 (de) | 2017-08-31 | 2019-03-06 | Evonik Degussa GmbH | Reaktivklebstoffe mit niedrigem gehalt an monomerem diisocyanat |
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| DE10351530A1 (de) * | 2003-11-03 | 2005-06-16 | Basf Ag | Verfahren zur Herstellung von Isocyanatgruppen enthaltenden Prepolymeren |
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| EP1602676A1 (en) * | 2004-06-01 | 2005-12-07 | SOLVAY (Société Anonyme) | Catalytic compositions |
| DE102004035764A1 (de) * | 2004-07-23 | 2006-03-16 | Bayer Materialscience Ag | Niedrigviskose Polyurethan-Prepolymere auf Basis von 2,4'-MDI |
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| DE102005035000A1 (de) | 2005-07-22 | 2007-01-25 | Basf Ag | Isocyanatgruppen enthaltende Prepolymere |
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| CN101679575B (zh) * | 2007-11-28 | 2013-09-18 | 奎克化学（中国）有限公司 | 单组分、湿固化聚氨酯粘合剂 |
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| JP6620964B2 (ja) * | 2017-12-12 | 2019-12-18 | Dic株式会社 | 無溶剤型ラミネート接着剤、その硬化物、積層体及び包装体 |
| EP3947506A1 (en) * | 2019-03-28 | 2022-02-09 | Basf Se | Process for producing polyurethane-polyisocyanurate elastomers, sealing materials and adhesives having a long pot life |
| PL3990510T3 (pl) | 2019-06-25 | 2025-02-10 | H.B. Fuller Company | Utwardzalna wilgocią kompozycja poliuretanowego kleju topliwego o niskim poziomie monomeru diizocyjanianu |
| DE102020111278A1 (de) | 2020-04-24 | 2021-10-28 | Klebchemie M.G. Becker Gmbh & Co. Kg | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
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| KR102390345B1 (ko) * | 2020-11-10 | 2022-04-22 | 테사 소시에타스 유로파에아 | 잠재 반응성 접착 화합물을 제조하기 위한 제제 |
| DE102021127517A1 (de) | 2021-10-22 | 2023-04-27 | Klebchemie M.G. Becker GmbH & Co KG | Reaktive Heißschmelzklebstoffzusammensetzungen basierend auf alpha-Silan-terminierten organischen Polymeren |
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2002
- 2002-07-02 DE DE10229519A patent/DE10229519A1/de not_active Withdrawn
- 2002-07-03 JP JP2003512288A patent/JP4317446B2/ja not_active Expired - Fee Related
- 2002-07-03 AT AT02764621T patent/ATE455810T1/de not_active IP Right Cessation
- 2002-07-03 EP EP02764621A patent/EP1404733B1/de not_active Revoked
- 2002-07-03 WO PCT/EP2002/007344 patent/WO2003006521A1/de not_active Ceased
- 2002-07-03 DE DE50214182T patent/DE50214182D1/de not_active Expired - Lifetime
- 2002-07-03 CA CA2453511A patent/CA2453511C/en not_active Expired - Fee Related
-
2004
- 2004-01-12 US US10/755,702 patent/US20040162385A1/en not_active Abandoned
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2008
- 2008-09-04 JP JP2008227295A patent/JP5015098B2/ja not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9637667B2 (en) | 2001-10-13 | 2017-05-02 | Henkel Ag & Co. Kgaa | Reactive polyurethane compositions with a low residual monomer content |
| DE10260974A1 (de) * | 2002-12-24 | 2004-07-15 | Fischerwerke Artur Fischer Gmbh & Co. Kg | Spezialmörtel für Mehrkomponentensysteme |
| DE10358667A1 (de) * | 2003-12-12 | 2005-07-14 | Votteler Lackfabrik Gmbh & Co. Kg | Mittel zur Isoliergrundierung von Holz und Holzwerkstoffen und dessen Verwendung |
| DE102004018048A1 (de) * | 2004-04-08 | 2005-11-10 | Henkel Kgaa | Verfahren zur Herstellung von Polyurethan-Prepolymeren |
| DE102004057292A1 (de) * | 2004-11-26 | 2006-06-01 | Klebchemie, M.G. Becker Gmbh & Co Kg | Verfahren zur Herstellung von reaktiven Polyurethanzusammensetzungen |
| DE102008025793A1 (de) * | 2008-05-29 | 2009-12-03 | Henkel Ag & Co. Kgaa | Reaktive Klebstoffe mit sehr geringem Gehalt an monomeren Diisocyanaten |
| DE102008027914A1 (de) * | 2008-06-12 | 2009-12-17 | Henkel Ag & Co. Kgaa | Vernetzende 2K-Isocyanat-Zusammensetzungen |
| DE102009033637A1 (de) | 2009-07-17 | 2011-01-20 | Bayer Materialscience Ag | Prepolymere |
| US8729210B2 (en) | 2009-07-17 | 2014-05-20 | Bayer Materialscience Ag | Prepolymers based on di- or polyisocyanates and formamide-terminated low molecular weight compounds, processes for preparing the same and uses thereof |
| EP3450476A1 (de) | 2017-08-31 | 2019-03-06 | Evonik Degussa GmbH | Reaktivklebstoffe mit niedrigem gehalt an monomerem diisocyanat |
| WO2019043054A1 (de) | 2017-08-31 | 2019-03-07 | Evonik Degussa Gmbh | Reaktivklebstoffe mit niedrigem gehalt an monomerem diisocyanat |
| CN111295404A (zh) * | 2017-08-31 | 2020-06-16 | 赢创运营有限公司 | 具有低含量的单体二异氰酸酯的反应性粘合剂 |
| CN111295404B (zh) * | 2017-08-31 | 2022-02-01 | 赢创运营有限公司 | 具有低含量的单体二异氰酸酯的反应性粘合剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE455810T1 (de) | 2010-02-15 |
| EP1404733A1 (de) | 2004-04-07 |
| JP4317446B2 (ja) | 2009-08-19 |
| JP2004534132A (ja) | 2004-11-11 |
| CA2453511C (en) | 2010-12-21 |
| CA2453511A1 (en) | 2003-01-23 |
| JP5015098B2 (ja) | 2012-08-29 |
| JP2009019211A (ja) | 2009-01-29 |
| DE50214182D1 (de) | 2010-03-11 |
| EP1404733B1 (de) | 2010-01-20 |
| WO2003006521A1 (de) | 2003-01-23 |
| US20040162385A1 (en) | 2004-08-19 |
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