CA2285776C - Silane-modified polyurethane resins, a process for their preparation and their use as moisture-curable resins - Google Patents
Silane-modified polyurethane resins, a process for their preparation and their use as moisture-curable resins Download PDFInfo
- Publication number
- CA2285776C CA2285776C CA002285776A CA2285776A CA2285776C CA 2285776 C CA2285776 C CA 2285776C CA 002285776 A CA002285776 A CA 002285776A CA 2285776 A CA2285776 A CA 2285776A CA 2285776 C CA2285776 C CA 2285776C
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- CA
- Canada
- Prior art keywords
- groups
- carbon atoms
- moisture
- isocyanate
- isocyanate groups
- 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.)
- Expired - Fee Related
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- 229920005989 resin Polymers 0.000 title claims abstract description 54
- 239000011347 resin Substances 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 12
- 229920005749 polyurethane resin Polymers 0.000 title description 2
- 239000004432 silane-modified polyurethane Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229920005862 polyol Polymers 0.000 claims abstract description 29
- 150000003077 polyols Chemical class 0.000 claims abstract description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000012948 isocyanate Substances 0.000 claims abstract description 21
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 21
- 239000004202 carbamide Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 6
- 239000000853 adhesive Substances 0.000 claims abstract description 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 51
- 239000005056 polyisocyanate Substances 0.000 claims description 40
- 229920001228 polyisocyanate Polymers 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000007789 sealing Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 30
- 125000005442 diisocyanate group Chemical group 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- 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 12
- -1 silane aspartates Chemical class 0.000 description 11
- 239000005058 Isophorone diisocyanate Substances 0.000 description 10
- 229910000077 silane Inorganic materials 0.000 description 10
- 239000007858 starting material Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- SDWPESPHXGVUEL-DKWTVANSSA-N (2S)-2-aminobutanedioic acid silane Chemical compound [SiH4].N[C@@H](CC(O)=O)C(O)=O SDWPESPHXGVUEL-DKWTVANSSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-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
- 150000001412 amines Chemical class 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 3
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000004658 ketimines Chemical class 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000004705 aldimines Chemical class 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RHLWQEFHFQTKNT-UHFFFAOYSA-N (2z)-1-cyclooctyl-2-diazocyclooctane Chemical compound [N-]=[N+]=C1CCCCCCC1C1CCCCCCC1 RHLWQEFHFQTKNT-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
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- 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 1
- 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 description 1
- AFVMPODRAIDZQC-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)cyclopentane Chemical compound O=C=NCC1CCCC1N=C=O AFVMPODRAIDZQC-UHFFFAOYSA-N 0.000 description 1
- VLNDSAWYJSNKOU-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylcyclohexyl)methyl]-2-methylcyclohexane Chemical compound C1CC(N=C=O)C(C)CC1CC1CC(C)C(N=C=O)CC1 VLNDSAWYJSNKOU-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- YFBFAHMPVMWKIM-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CCCNC1CCCCC1 YFBFAHMPVMWKIM-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/809—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/172,750 | 1998-10-14 | ||
| US09/172,750 US6046270A (en) | 1998-10-14 | 1998-10-14 | Silane-modified polyurethane resins, a process for their preparation and their use as moisture-curable resins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285776A1 CA2285776A1 (en) | 2000-04-14 |
| CA2285776C true CA2285776C (en) | 2009-12-15 |
Family
ID=22629063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285776A Expired - Fee Related CA2285776C (en) | 1998-10-14 | 1999-10-08 | Silane-modified polyurethane resins, a process for their preparation and their use as moisture-curable resins |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6046270A (https=) |
| EP (1) | EP0994117B1 (https=) |
| JP (1) | JP4624509B2 (https=) |
| AT (1) | ATE234848T1 (https=) |
| CA (1) | CA2285776C (https=) |
| DE (1) | DE69906002T2 (https=) |
| DK (1) | DK0994117T3 (https=) |
| ES (1) | ES2192821T3 (https=) |
| PT (1) | PT994117E (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200347183A1 (en) * | 2017-12-28 | 2020-11-05 | Covestro Deutschland Ag | Silane-modified polyurea compounds based on polyisocyanates having isocyanurate and allophanate groups |
Families Citing this family (128)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3263034B2 (ja) * | 1997-11-12 | 2002-03-04 | 横浜ゴム株式会社 | ポリウレタン組成物 |
| US6329488B1 (en) * | 1998-11-10 | 2001-12-11 | C. R. Bard, Inc. | Silane copolymer coatings |
| US6596401B1 (en) * | 1998-11-10 | 2003-07-22 | C. R. Bard Inc. | Silane copolymer compositions containing active agents |
| US6162938A (en) * | 1998-11-19 | 2000-12-19 | 3M Innovative Properties Company | Secondary amine-functional silanes, silane-functional polymers therefrom, and resulting cured polymers |
| DE10013628A1 (de) * | 2000-03-18 | 2001-09-20 | Degussa | Stabile 1:1-Monoaddukte aus sekundären Aminoalkylalkoxysilanen und Diisocyanaten sowie ein Verfahren zu ihrer Herstellung |
| US6494003B1 (en) * | 2000-03-24 | 2002-12-17 | Hori Glass Co., Ltd. | Vehicle window glass and method of producing the same |
| AU2001261335A1 (en) * | 2000-06-22 | 2002-01-02 | Basf Corporation | Coating compositions having improved adhesion to aluminum substrates |
| US6534121B1 (en) * | 2000-06-22 | 2003-03-18 | Basf Corporation | Method of coating bare, untreated metal substrates |
| DE10132678A1 (de) | 2000-07-26 | 2002-02-07 | Henkel Kgaa | Alkoxysilylgruppenhaltige Bindemittel und Bindemittelzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| US20040030088A1 (en) * | 2002-08-07 | 2004-02-12 | Basf Corporation | Acidic reducer for providing increased adhesion of a two component polyurethane primer to substrates |
| US20040071887A1 (en) * | 2002-10-10 | 2004-04-15 | Basf Corporation | Coating compositions having improved "direct to metal" adhesion and method therefore |
| US7482420B2 (en) * | 2004-03-24 | 2009-01-27 | Construction Research & Technology Gmbh | Silane-terminated polyurethanes with high strength and high elongation |
| US7888425B2 (en) * | 2004-07-16 | 2011-02-15 | Reichhold, Inc. | Low volatile organic compound stable solvent-based polyurethane compositions for coatings |
| BRPI0516402A (pt) * | 2004-10-25 | 2008-09-02 | Dow Global Technologies Inc | pré-polìmero contendo pelo menos um grupo uretano e polìmero |
| CN101056945B (zh) | 2004-11-10 | 2011-04-13 | 株式会社钟化 | 固化性组合物 |
| EP1717240B1 (de) | 2005-04-29 | 2010-09-22 | Sika Technology AG | Organoalkoxysilane zur Verwendung in feuchtigkeitshärtenden Zusammensetzungen |
| EP1939257B1 (en) | 2005-09-30 | 2017-06-21 | Kaneka Corporation | Curable composition |
| DE602006018346D1 (de) | 2005-09-30 | 2010-12-30 | Kaneka Corp | Härtbare zusammensetzung mit verbesserter härtung und lagerstabilität |
| EP1930376B2 (en) | 2005-09-30 | 2016-09-07 | Kaneka Corporation | Curable composition |
| US20090182091A1 (en) | 2006-02-16 | 2009-07-16 | Kaneka Corporation | Curable composition |
| WO2007123167A1 (ja) | 2006-04-20 | 2007-11-01 | Kaneka Corporation | 硬化性組成物 |
| WO2008032539A1 (en) | 2006-09-13 | 2008-03-20 | Kaneka Corporation | MOISTURE-CURABLE POLYMER HAVING SiF GROUP AND CURABLE COMPOSITION CONTAINING THE SAME |
| DE102006054289A1 (de) * | 2006-11-17 | 2008-05-21 | Bayer Materialscience Ag | Nanopartikelmodifizierte Polyisocyanate |
| WO2008062866A1 (en) | 2006-11-22 | 2008-05-29 | Kaneka Corporation | Curable composition and catalyst composition |
| PL2091988T3 (pl) | 2006-12-19 | 2013-07-31 | Basf Coatings Gmbh | Środek po włokowy o wysokiej odporności na zadrapania i odporności na działanie czynników atmosferycznych |
| EP2100923B1 (en) | 2006-12-25 | 2013-03-13 | Kaneka Corporation | Curable composition |
| US8415444B2 (en) | 2007-01-12 | 2013-04-09 | Kaneka Corporation | Curable composition |
| DE102007021630A1 (de) * | 2007-05-09 | 2008-11-13 | Bayer Materialscience Ag | Hybride Polyisocyanate |
| JPWO2009011329A1 (ja) | 2007-07-19 | 2010-09-24 | 株式会社カネカ | 硬化性組成物 |
| WO2009065654A1 (de) * | 2007-11-21 | 2009-05-28 | Sika Technology Ag | Feuchtigkeitshärtende zusammensetzung umfassend mindestens zwei silangruppen-aufweisende polymere |
| DE102007061854A1 (de) | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Beschichtungsmittel mit hoher Kratzbeständigkeit und Witterungsstabilität |
| DE102007061856A1 (de) | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Beschichtungsmittel mit hoher Kratzbeständigkeit und Witterungsstabilität |
| DE102007061855A1 (de) | 2007-12-19 | 2009-06-25 | Basf Coatings Ag | Beschichtungsmittel mit hoher Kratzbeständigkeit und Witterungsstabilität |
| US20090165676A1 (en) * | 2007-12-26 | 2009-07-02 | E.I. Du Pont De Nemours And Company | Bis(n-silylalkyl)aspartimides and processes therefor |
| DE102008030304A1 (de) | 2008-06-25 | 2009-12-31 | Basf Coatings Ag | Verwendung teilsilanisierter Verbindungen auf Polyisocyanatbasis als Vernetzungsmittel in Beschichtungszusammensetzungen und Beschichtungszusammensetzung enthaltend die Verbindungen |
| JP5547641B2 (ja) | 2008-09-29 | 2014-07-16 | 株式会社カネカ | 硬化性組成物およびその硬化物 |
| DE102008060454A1 (de) | 2008-12-05 | 2010-06-10 | Basf Coatings Ag | Beschichtungsmittel und daraus hergestellte Beschichtungen mit hoher Kratzbeständigkeit und Witterungsstabilität sowie guten optischen Eigenschaften |
| EP2388297B1 (en) | 2009-01-16 | 2020-08-19 | Kaneka Corporation | Curable composition and cured object formed therefrom |
| DE102009024103A1 (de) | 2009-06-06 | 2010-12-09 | Basf Coatings Gmbh | Beschichtungsmittel und daraus hergestellte Beschichtungen mit hoher Kratzfestigkeit und hoher Kocherstabilität |
| DE102009041380A1 (de) * | 2009-09-12 | 2011-03-24 | Basf Coatings Gmbh | Bindemittelmischung und sie enthaltende Beschichtungsmittel sowie daraus hergestellte Beschichtungen mit hoher Kratzbeständigkeit und Witterungsstabilität sowie guten optischen Eigenschaften |
| CN104262933B (zh) | 2009-10-16 | 2017-05-03 | 株式会社钟化 | 固化性组合物 |
| DE102009054071A1 (de) | 2009-11-20 | 2011-05-26 | Basf Coatings Gmbh | Beschichtungsmittel mit guter Lagerbeständigkeit und daraus hergestellte Beschichtungen mit hoher Kratzfestigkeit bei gleichzeitig guter Witterungsbeständigkeit |
| US9023932B2 (en) | 2010-01-19 | 2015-05-05 | Kaneka Corporation | Curable composition |
| DE102010015683A1 (de) | 2010-04-21 | 2011-10-27 | Basf Coatings Gmbh | Beschichtungsmittel mit hohem Festkörpergehalt und gutem Verlauf sowie daraus hergestellte Mehrschichtlackierungen und deren Verwendung |
| MX2012010550A (es) | 2010-04-21 | 2012-11-16 | Basf Coatings Gmbh | Materiales de recubrimiento con alto contenido de solidos y sistemas de pintura de multiple capa con buena nivelacion producidos de los mismos y usos de los mismos. |
| DE102010015675A1 (de) | 2010-04-21 | 2011-10-27 | Basf Coatings Gmbh | Beschichtungsmittel mit verbesserter Ablaufneigung |
| WO2012057092A1 (ja) | 2010-10-27 | 2012-05-03 | 株式会社カネカ | 硬化性組成物 |
| EP2640779B1 (de) | 2010-11-18 | 2015-08-05 | BASF Coatings GmbH | Polyurethan-beschichtungsmittel, daraus hergestellte mehrschichtlackierungen mit matter oberfläche sowie verfahren zur herstellung der mehrschichtlackierungen |
| JP5943932B2 (ja) | 2010-11-19 | 2016-07-05 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 高固形分及び良好な流展性を有するコーティング剤並びにそれより製造された多層塗膜並びにその使用 |
| EP2665758B1 (de) | 2011-01-20 | 2017-12-06 | BASF Coatings GmbH | Wässriges polyurethanbeschichtungsmittel und daraus hergestellte beschichtungen mit hoher kratzbeständigkeit und guter chemikalienbeständigkeit |
| WO2012121288A1 (ja) | 2011-03-09 | 2012-09-13 | 株式会社カネカ | 接着剤組成物と木材からなる接着構造体 |
| KR101928117B1 (ko) | 2011-03-14 | 2018-12-11 | 바스프 코팅스 게엠베하 | 폴리우레탄 코팅 물질 조성물, 이러한 코팅 물질 조성물을 사용한 다단식 코팅 방법, 및 또한 클리어코트 물질 및 착색된 코팅 물질로서 코팅 물질 조성물의 용도, 및 자동차 리피니시 및/또는 플라스틱 기판 및/또는 다용도 차량의 코팅을 위한 코팅 방법의 적용 |
| ES2527273T3 (es) | 2011-03-14 | 2015-01-22 | Basf Coatings Gmbh | Composición de agentes de recubrimiento de poliuretano, métodos de recubrimiento de varias etapas por empleo de estas composiciones de agentes de recubrimiento, así como el empleo de las composiciones de agentes de recubrimiento como laca clara y laca pigmentada o bien aplicación del método de recubrimiento, para el lacado de refacción de automóviles y/o para el recubrimiento de sustratos plásticos y/o vehículos utilitarios |
| BR112013022041B1 (pt) | 2011-03-14 | 2020-04-28 | Basf Coatings Gmbh | composição de revestimento de material e seu uso, método para revestimento multicelular e seu uso, e uso de um complexo de zinco-amidina |
| WO2012126796A1 (de) | 2011-03-18 | 2012-09-27 | Basf Coatings Gmbh | Zink-imidazol-carboxylat-komplex katalysierte beschichtungsmittelzusammensetzung |
| CN103649428B (zh) | 2011-04-15 | 2016-06-22 | 株式会社钟化 | 建筑用外装材料 |
| US9371469B2 (en) | 2011-06-09 | 2016-06-21 | Basf Coatings Gmbh | Coating agent compositions, coatings made therefrom and exhibiting high scratch resistance and good polishability, and use thereof |
| CN103547607B (zh) | 2011-06-09 | 2015-07-15 | 巴斯夫涂料有限公司 | 涂布剂组合物和由其制备的具有高耐划伤性且同时具有良好的可抛光性的涂层及其用途 |
| JP6033289B2 (ja) | 2011-06-09 | 2016-11-30 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 被覆剤組成物および該組成物から製造された高い耐引掻性と同時に良好な研磨性を有する被覆ならびにその使用 |
| CN103814101B9 (zh) | 2011-09-22 | 2017-03-01 | 株式会社钟化 | 固化性组合物及其固化物 |
| CN103946321B (zh) | 2011-11-17 | 2016-08-24 | 巴斯夫涂料有限公司 | 包含甘油二酯的涂料及其在多层漆中的用途 |
| WO2013072481A1 (de) | 2011-11-17 | 2013-05-23 | Basf Coatings Gmbh | Glyceroldiester, verfahren zu deren herstellung und deren verwendung in beschichtungsmitteln |
| KR101141629B1 (ko) * | 2011-11-24 | 2012-05-17 | 주식회사 세명크리텍 | 실란화합물을 함유하여 습윤면 부착성능과 내구성을 향상시킨 실란변성 폴리우레아 수지 도막방수재 및 이를 이용한 방수?방식공법 |
| MX2014009035A (es) | 2012-01-25 | 2014-10-24 | Basf Coatings Gmbh | Composicion de material de revestimiento catalizada con complejo de (1 - metilimidazol) bis (2 - etilhexanoato) de zinc. |
| JP5889088B2 (ja) * | 2012-03-30 | 2016-03-22 | リンテック株式会社 | 粘着剤組成物および粘着シート |
| CN104487473B (zh) | 2012-07-25 | 2017-05-17 | 巴斯夫涂料有限公司 | 聚氨酯涂料组合物、多阶段涂覆方法 |
| CN104487472B (zh) | 2012-07-25 | 2017-07-14 | 巴斯夫涂料有限公司 | 聚氨酯涂料组合物及其用途、多阶段涂覆方法 |
| JP6035953B2 (ja) * | 2012-07-27 | 2016-11-30 | 横浜ゴム株式会社 | ウレタン接着剤組成物 |
| CN104736583B (zh) | 2012-10-04 | 2017-03-15 | 巴斯夫涂料有限公司 | 含氟非水性涂料组合物、涂覆方法和涂料组合物的用途 |
| CN104903374B (zh) | 2012-12-03 | 2017-08-29 | 巴斯夫涂料有限公司 | 涂料组合物和由其制备的具有高耐刮擦性与良好抛光性和良好光学性能的涂层、及其用途 |
| MX374622B (es) | 2012-12-03 | 2025-03-06 | Basf Coatings Gmbh | Pintura de varias capas que induce efecto y/o color y método para su producción, y su uso. |
| US10016454B2 (en) | 2012-12-04 | 2018-07-10 | Cohera Medical, Inc. | Silane-containing moisture-curable tissue sealant |
| CN104968717A (zh) | 2013-02-01 | 2015-10-07 | 3M创新有限公司 | 涂料组合物及由其制得的制品 |
| EP2851403A1 (de) | 2013-09-23 | 2015-03-25 | BASF Coatings GmbH | Beschichtungsmittelzusammensetzungen und daraus hergestellte, bei niedrigen temperaturen härtbare beschichtungen und sowie deren verwendung |
| US20160326344A1 (en) | 2013-12-26 | 2016-11-10 | Kaneka Corporation | Curable composition and cured product thereof |
| EP2896639A1 (de) | 2014-01-15 | 2015-07-22 | BASF Coatings GmbH | Beschichtete metallisierte Oberflächen |
| EP3108076B1 (en) | 2014-02-18 | 2025-03-26 | 3M Innovative Properties Company | Easy to apply air and water barrier articles |
| KR20220041946A (ko) | 2014-02-18 | 2022-04-01 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 자가 밀봉 물품 |
| EP2910612A1 (de) | 2014-02-20 | 2015-08-26 | BASF Coatings GmbH | Beschichtungsmittelzusammensetzungen und daraus hergestellte Beschichtungen und sowie deren Verwendung |
| CN104479609A (zh) * | 2014-06-18 | 2015-04-01 | 广东新展化工新材料有限公司 | 一种端硅烷基改性聚氨酯密封胶及其制备方法 |
| WO2016019248A1 (en) | 2014-08-01 | 2016-02-04 | 3M Innovative Properties Company | Self sealing permeable air barrier compositions |
| JP6619008B2 (ja) | 2014-12-08 | 2019-12-11 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | コーティング材料組成物、およびそれらから生成されるコーティング、ならびにその使用方法 |
| MX375884B (es) | 2014-12-08 | 2025-03-06 | Basf Coatings Gmbh | Composiciones no acuosas de materiales de recubrimiento, recubrimientos producidos a partir de ellas y que tienen mejoradas adhesion y resistencia a los arañazos y tambien el uso de las mismas. |
| CN107109152B (zh) | 2014-12-22 | 2020-11-03 | 3M创新有限公司 | 空气和水阻挡制品 |
| US11479633B2 (en) | 2015-01-22 | 2022-10-25 | Akzo Nobel Coatings International B.V. | Coating material, system based on Li/Bi catalysts |
| US9976028B2 (en) | 2015-02-23 | 2018-05-22 | King Industries | Curable coating compositions of silane functional polymers |
| KR102071433B1 (ko) | 2015-06-15 | 2020-01-30 | 바스프 코팅스 게엠베하 | 폴리우레탄 코팅제 조성물 및 다층 페인트 시스템의 제조를 위한 그의 용도 |
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| CN107771200A (zh) | 2015-06-15 | 2018-03-06 | 巴斯夫涂料有限公司 | 涂覆轮辋的方法及以此得到的防污和防制动粉尘的涂层 |
| WO2017031275A1 (en) | 2015-08-18 | 2017-02-23 | 3M Innovative Properties Company | Self-sealing articles including elastic porous layer |
| WO2017085268A1 (de) | 2015-11-20 | 2017-05-26 | Covestro Deutschland Ag | Mehrschichtiger lackaufbau mit thermolatentem katalysator |
| WO2017112756A1 (en) | 2015-12-22 | 2017-06-29 | 3M Innovative Properties Company | Roll including air and water barrier article and method of using the same |
| EP3392036B1 (en) | 2015-12-24 | 2022-03-30 | Kaneka Corporation | Method for producing laminate, and laminate |
| EP3445827A1 (de) | 2016-04-22 | 2019-02-27 | Covestro Deutschland AG | Thermolatent katalysiertes zwei-komponenten-system |
| JP2019519642A (ja) | 2016-05-24 | 2019-07-11 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 汚染耐性および（自己）浄化特性が改善されたコーティング組成物ならびにそれから製造されるコーティング、ならびにそれを使用する方法 |
| WO2018069018A1 (de) | 2016-10-13 | 2018-04-19 | Basf Coatings Gmbh | Beschichtungsmittelsystem basierend auf salzen einer aliphatischen monocarbonsäure |
| WO2018087743A1 (ja) * | 2016-11-14 | 2018-05-17 | 積水化学工業株式会社 | 湿気硬化型樹脂組成物及び組立部品 |
| US11624014B2 (en) | 2017-02-06 | 2023-04-11 | Bistik, Inc. | Moisture-curable adhesive composition and a method for mounting tiles on wall surfaces |
| WO2018156631A1 (en) | 2017-02-23 | 2018-08-30 | 3M Innovative Properties Company | Air and water barrier article including inelastic porous layer |
| MX2019012276A (es) | 2017-04-11 | 2019-12-19 | Basf Coatings Gmbh | Materiales de recubrimiento que producen superficies estructuradas. |
| EP3444290A1 (de) | 2017-08-16 | 2019-02-20 | Covestro Deutschland AG | Indikatorsystem |
| EP3444289A1 (de) | 2017-08-16 | 2019-02-20 | Covestro Deutschland AG | Saures indikatorsystem |
| CN108101405A (zh) * | 2017-12-29 | 2018-06-01 | 深圳市嘉达高科产业发展有限公司 | 一种透水混凝土增强剂及其制备方法 |
| WO2019159972A1 (ja) | 2018-02-13 | 2019-08-22 | 株式会社カネカ | ワーキングジョイント用１成分型硬化性組成物 |
| KR20210087939A (ko) | 2018-10-30 | 2021-07-13 | 코베스트로 인텔렉쳐 프로퍼티 게엠베하 운트 콤파니 카게 | 개선된 층 접착력을 갖는 다층 페인트 구조 |
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| CN114206605A (zh) | 2019-08-07 | 2022-03-18 | 3M创新有限公司 | 带材、包括带材和复合层的制品及相关方法 |
| US20220306894A1 (en) | 2019-08-23 | 2022-09-29 | Basf Coatings Gmbh | Coating material system comprising a mercapto group-containing compound |
| CN114555733B (zh) | 2019-10-14 | 2024-05-07 | 巴斯夫涂料有限公司 | 基于包含至少一个芳族取代基的含铋催化剂的涂料体系 |
| EP3822297A1 (de) | 2019-11-15 | 2021-05-19 | Covestro Deutschland AG | Polysiloxan-funktionalisierte polyurethane zur steigerung der hydrophobie von oberflächen |
| WO2021224232A1 (en) | 2020-05-04 | 2021-11-11 | Basf Coatings Gmbh | Coating systems with increased jetness of black and improved color |
| EP3957693A1 (en) | 2020-08-18 | 2022-02-23 | BASF Coatings GmbH | Block copolymer containing high solids basecoats for prevention of tackiness defects |
| US20230332011A1 (en) | 2020-08-28 | 2023-10-19 | Basf Coatings Gmbh | Solvent-Borne, Two-Pack, Anticorrosion Coating Composition |
| JP7651692B2 (ja) | 2020-10-22 | 2025-03-26 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | グラフェンオキシドのアルカリ塩を含むコーティング組成物及び前記コーティング組成物から製造されたコーティング層 |
| WO2022200533A1 (en) | 2021-03-26 | 2022-09-29 | Basf Coatings Gmbh | Clearcoat compositions for providing clearcoats with no or reduced whitening |
| US20240209140A1 (en) | 2021-04-28 | 2024-06-27 | Basf Coatings Gmbh | Hydroxyl-functional thioether compounds and their use in curable compositions |
| KR20250022150A (ko) | 2022-06-09 | 2025-02-14 | 바스프 코팅스 게엠베하 | 탁월한 외관을 갖는 저온 경화성 다층 코팅 시스템 |
| WO2023237604A1 (en) | 2022-06-09 | 2023-12-14 | Basf Coatings Gmbh | Primer coating system and composition for achieving excellent water resistance |
| EP4303246A1 (de) | 2022-07-04 | 2024-01-10 | Covestro Deutschland AG | Polyisocyanatgemisch |
| EP4455177A1 (en) | 2023-04-25 | 2024-10-30 | Covestro Deutschland AG | Use of thermolatent catalyst to improve properties of single-layer polyurethane coatings |
| US20250215139A1 (en) * | 2024-01-02 | 2025-07-03 | Covestro Llc | Ethylenically unsaturated oligomers, methods for their preparation, and the use thereof in coating compositions |
| US12187852B1 (en) * | 2024-01-02 | 2025-01-07 | Covestro Llc | Ethylenically unsaturated oligomers, methods for their preparation, and the use thereof in coating compositions |
| US12428514B2 (en) | 2024-01-02 | 2025-09-30 | Covestro Llc | Ethylenically unsaturated compounds, methods for their preparation, and the use thereof in coating compositions |
| WO2025219975A1 (en) | 2024-04-18 | 2025-10-23 | 3M Innovative Properties Company | Polymeric multilayer film and article and related process |
| WO2025223454A1 (en) | 2024-04-24 | 2025-10-30 | Basf Coatings Gmbh | A curable coating composition and its curing method |
| WO2026027456A1 (en) | 2024-07-29 | 2026-02-05 | Basf Coatings Gmbh | Scratch resistant coatings with good appearance and plastic compatibility |
| WO2026077939A1 (en) | 2024-10-08 | 2026-04-16 | Basf Coatings Gmbh | Clearcoat compositions for providing clearcoats with stable gloss across varying dry layer thicknesses |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1064841A (en) * | 1963-02-04 | 1967-04-12 | Ici Ltd | Manufacture of polymers containing biuret and urea groups |
| US3567692A (en) * | 1963-02-04 | 1971-03-02 | Ici Ltd | Polymeric materials produced by interacting polyisocyanate and water in the presence of polyaldimine or polyketimine |
| US4067844A (en) * | 1976-12-22 | 1978-01-10 | Tremco Incorporated | Urethane polymers and sealant compositions containing the same |
| US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
| KR950006938B1 (ko) * | 1986-11-19 | 1995-06-26 | 시바-가이기 아게 | 접착 촉진제 |
| US5147927A (en) * | 1989-01-27 | 1992-09-15 | Basf Corporation | Room-temperature, moisture-curable, primerless, polyurethane-based adhesive composition and method |
| CA2052842C (en) * | 1990-10-09 | 1999-08-24 | Hideyuki Ohnari | Curable resin and composition containing the same |
| US5162426A (en) * | 1990-12-17 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Coatings comprising dispersed polymers with silane crosslinking |
| DE4237468A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Alkoxysilan- und Aminogruppen aufweisende Verbindungen |
| CN1076662C (zh) * | 1994-01-24 | 2001-12-26 | 住友化学工业株式会社 | 层叠体、层叠膜及其成形品 |
| US6001946A (en) * | 1996-09-23 | 1999-12-14 | Witco Corporation | Curable silane-encapped compositions having improved performances |
| JP3296982B2 (ja) * | 1996-12-11 | 2002-07-02 | サンスター技研株式会社 | 一液型湿気硬化性組成物 |
| US5852137A (en) * | 1997-01-29 | 1998-12-22 | Essex Specialty Products | Polyurethane sealant compositions |
| US5908948A (en) * | 1997-03-11 | 1999-06-01 | Bayer Corporation | Compounds containing urea and alkoxysilane groups |
| US6005047A (en) * | 1998-10-14 | 1999-12-21 | Bayer Corporation | Moisture-curable compounds containing isocyanate and alkoxysilane groups |
-
1998
- 1998-10-14 US US09/172,750 patent/US6046270A/en not_active Expired - Lifetime
-
1999
- 1999-10-01 DE DE69906002T patent/DE69906002T2/de not_active Expired - Lifetime
- 1999-10-01 EP EP99119079A patent/EP0994117B1/en not_active Expired - Lifetime
- 1999-10-01 ES ES99119079T patent/ES2192821T3/es not_active Expired - Lifetime
- 1999-10-01 PT PT99119079T patent/PT994117E/pt unknown
- 1999-10-01 AT AT99119079T patent/ATE234848T1/de active
- 1999-10-01 DK DK99119079T patent/DK0994117T3/da active
- 1999-10-08 CA CA002285776A patent/CA2285776C/en not_active Expired - Fee Related
- 1999-10-12 JP JP28951599A patent/JP4624509B2/ja not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20200347183A1 (en) * | 2017-12-28 | 2020-11-05 | Covestro Deutschland Ag | Silane-modified polyurea compounds based on polyisocyanates having isocyanurate and allophanate groups |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0994117A1 (en) | 2000-04-19 |
| JP4624509B2 (ja) | 2011-02-02 |
| JP2000119365A (ja) | 2000-04-25 |
| ATE234848T1 (de) | 2003-04-15 |
| EP0994117B1 (en) | 2003-03-19 |
| US6046270A (en) | 2000-04-04 |
| ES2192821T3 (es) | 2003-10-16 |
| DE69906002T2 (de) | 2004-01-08 |
| DK0994117T3 (da) | 2003-06-02 |
| DE69906002D1 (de) | 2003-04-24 |
| CA2285776A1 (en) | 2000-04-14 |
| PT994117E (pt) | 2003-07-31 |
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