CN107540807A - 烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂 - Google Patents
烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂 Download PDFInfo
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- CN107540807A CN107540807A CN201710493042.7A CN201710493042A CN107540807A CN 107540807 A CN107540807 A CN 107540807A CN 201710493042 A CN201710493042 A CN 201710493042A CN 107540807 A CN107540807 A CN 107540807A
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- Prior art keywords
- diisocyanate
- coating agent
- ammonium
- methyl
- adhesive
- 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.)
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- 239000011248 coating agent Substances 0.000 title claims abstract description 66
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000000853 adhesive Substances 0.000 claims description 56
- 230000001070 adhesive effect Effects 0.000 claims description 56
- -1 normal-butyl Chemical group 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 40
- 125000005442 diisocyanate group Chemical group 0.000 claims description 32
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 239000005056 polyisocyanate Substances 0.000 claims description 24
- 229920001228 polyisocyanate Polymers 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- QQBWQAURZPGDOG-UHFFFAOYSA-N ethyl hexanoate;zinc Chemical compound [Zn].CCCCCC(=O)OCC QQBWQAURZPGDOG-UHFFFAOYSA-N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000003973 paint Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 229910000077 silane Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000008199 coating composition Substances 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 229920000058 polyacrylate Polymers 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 5
- 239000004411 aluminium Substances 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 239000012752 auxiliary agent Substances 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical class O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 4
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical class O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- UPYSSRQCIUAPEE-UHFFFAOYSA-N azanium 1,2,3,4-tetraethylbenzene formate Chemical compound C(=O)[O-].[NH4+].C(C)C1=C(C(=C(C=C1)CC)CC)CC UPYSSRQCIUAPEE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003223 protective agent Substances 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 3
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 3
- CARJIADDUWZYDB-UHFFFAOYSA-N 1-[diethoxy(methyl)silyl]oxyethanamine Chemical compound CCO[Si](C)(OCC)OC(C)N CARJIADDUWZYDB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004425 Makrolon Substances 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 claims 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims 1
- 150000004992 toluidines Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 21
- 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 20
- 239000005058 Isophorone diisocyanate Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- DOFHXXBIPRPYSZ-UHFFFAOYSA-N [cyclohexyl(isocyanato)methyl]cyclohexane Chemical class C1CCCCC1C(N=C=O)C1CCCCC1 DOFHXXBIPRPYSZ-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- OBBQDLHBLQTARQ-UHFFFAOYSA-N hexan-1-amine;hydrate Chemical compound [OH-].CCCCCC[NH3+] OBBQDLHBLQTARQ-UHFFFAOYSA-N 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 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 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 3
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 3
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 3
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical group N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical group 0.000 description 3
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 3
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
- 229940107816 ammonium iodide Drugs 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000008859 change Effects 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
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 3
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 description 2
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
- HSNJERRVXUNQLS-UHFFFAOYSA-N 1-(4-tert-butylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(C(C)(C)C)C=C1 HSNJERRVXUNQLS-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KEZMBAQUUXDDDQ-UHFFFAOYSA-N CCC.N=C=O.N=C=O Chemical compound CCC.N=C=O.N=C=O KEZMBAQUUXDDDQ-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
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- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
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Abstract
本发明涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂。本发明还涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂的制备方法以及用途。
Description
技术领域
本发明涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂、其制备方法及其用途。
现有技术
数十年来，聚氨酯被证明是漆料、胶粘剂、密封剂和塑料体系的高品质组分。在此，额外的烷氧基硅烷基团可以起到重要作用，例如在网络密度、耐化学品性和耐刮擦性方面，这里主要是通过形成硅氧烷和聚硅氧烷的结构。
既具有烷氧基硅烷基团又具有异氰酸酯基团的分子实现了通过一种组分引入作为反应产物得到的官能度、硅氧烷和聚氨酯基团。长期以来一直使用这样的物质，例如以异氰酸根合烷基三烷氧基硅烷的形式。
由异氰酸根合烷基三烷氧基硅烷和醇制得的烷氧基硅烷封端的聚氨酯同样是已知的并且例如用于制备高度交联的、硬质涂覆剂 (例如EP 2676982 A1)。然而，在EP2676982 A1中描述的含有烷氧基硅烷的涂覆剂是不利的，因为它们仅具有短的可使用时间（Topfzeiten）。
含有脲基甲酸酯的粘合剂是长久已知的。烷氧基硅烷官能化的脲基甲酸酯也是已知的。这里区分为下面描述的不同类型，但是它们在结构和应用方面都不对应于在本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂中包含的烷氧基硅烷官能化的脲基甲酸酯。
例如，在WO 2008/043722 A1中描述的脲基甲酸酯 III (1) 通过NCO封端的含有脲基甲酸酯的聚氨酯 I (1) 与对异氰酸酯呈反应性的烷氧基硅烷 II (1) (例如氨基烷基三烷氧基硅烷) 的反应而获得。由此，脲基甲酸酯基团位于聚氨酯链的中心和烷氧基硅烷官能团通过末端的异氰酸酯基团连接到脲官能团的结构中 (结构 III (1)，反应式1)。
DE102005041953 A1 描述了平均分子量为3000-20000 g/mol 的多元醇 I (2)与过量的异氰酸根合丙基三甲氧基硅烷II (2) 的反应，从而在形成聚氨酯 III (2) 之后形成每个脲基甲酸酯单元具有两个烷氧基硅烷官能团的脲基甲酸酯 IV (2)。
在DE102005041954 A1中，将聚氨酯 I (3) 与异氰酸根合丙基三甲氧基硅烷II(3) 混合并且加热直至形成脲基甲酸酯结构。在这种情况下，将烷氧基硅烷基团结合到脲基甲酸酯基团 III (3) 的末端氮上 (反应式3)。
J. Kozakiewicz等人在Progress in Organic Coatings 72 (2011) 120–130中公开了异氰酸根合丙基三甲氧基硅烷I (4) 与甲醇反应得到相应的氨基甲酸酯 II (4)和随后与六亚甲基二异氰酸酯三聚体 III (4)反应。在由此获得的高粘度脲基甲酸酯 IV(4) 中，烷氧基硅烷官能团挂接到脲基甲酸酯基团的中心叔胺上 (反应式4)。
在所述的应用中，脲基甲酸酯官能团用作六亚甲基二异氰酸酯三聚体的阻隔剂，而六亚甲基二异氰酸酯三聚体用作羟基官能化的聚酯多元醇的交联剂。
即使如今仍然需要新型的、具有特定性质的、含硅烷的涂覆剂。
在EP 2676982 A1中描述的含有烷氧基硅烷的粘合剂是不利的，因为它们仅具有短的可使用时间。
发明内容
本发明的目的在于，提供新型的含硅烷的涂覆剂，其适用于研发高度交联的硬质涂层和其特征在于延长的可使用时间。
该目的通过根据本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂而实现。
令人惊讶地发现，本发明的烷氧基硅烷官能化的和含有脲基甲酸酯的涂覆剂适用作漆料、胶粘剂或密封剂。特别地，本发明的烷氧基硅烷官能化的和含有脲基甲酸酯的涂覆剂可以用于研发高度交联的、特别是硬质的、具有好的粘合性的涂层。此外，本发明的烷氧基硅烷官能化的和含有脲基甲酸酯的涂覆剂（其包含本发明的烷氧基硅烷官能化的和含有脲基甲酸酯的粘合剂组分 a)）的特征在于长的可使用时间。
本发明涉及烷氧基硅烷官能化的和含有脲基甲酸酯的涂覆剂，其包含
a)作为粘合剂组分，10-99重量%的至少一种i)与ii)的反应产物
i)至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 i)
Rn(OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
ii)至少一种二异氰酸酯 ii)，
其中i)与ii)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
b)1-90重量%的至少另一种与a)不同的粘合剂组分，优选含羟基或含胺基的粘合剂组分，
c)0-50重量%的至少一种芳族的、脂族的或环脂族的多异氰酸酯，其NCO官能度为至少2，优选 2.8至6，
d)0-5重量%的至少一种催化剂，
其中组分a)-d)之和为100重量%，
e)任选的助剂和/或添加剂，
f)任选的溶剂。
本发明的含有脲基甲酸酯的涂覆剂是这样的涂覆剂，其包含至少一种单氨基甲酸酯与至少一种二异氰酸酯的至少一种反应产物。如由至少一种单氨基甲酸酯与至少一种二异氰酸酯的反应可以看出的，相应的反应产物是指平均具有一个或两个脲基甲酸酯单元的加合物，因为二异氰酸酯可以部分或完全地与一个或两个单氨基甲酸酯反应。然而优选地，本发明的反应产物具有两个脲基甲酸酯单元。
所述反应产物通过至少一种单氨基甲酸酯与至少一种二异氰酸酯以所述化学计量反应获得。优选地，所述反应产物通过一种单氨基甲酸酯与至少一种二异氰酸酯以所述化学计量反应获得。更优选地，所述反应产物通过一种单氨基甲酸酯与一种二异氰酸酯以所述化学计量反应获得。在此，一种单氨基甲酸酯或一种二异氰酸酯分别特别是指一个结构式中的各个单氨基甲酸酯或各个二异氰酸酯。
在此，“一种”单氨基甲酸酯或“一种”二异氰酸酯分别特别是指一个结构式中的各个单氨基甲酸酯或二异氰酸酯。
优选地，术语“粘合剂组分”可以是指粘合剂和交联剂，更优选粘合剂。
优选地，本发明不仅涉及包含所述组分a) - f)的涂覆剂，还涉及由它们组成的涂覆剂。因此，本发明优选涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂，其由a)-f)组成：
a)作为粘合剂组分，10-99重量%的至少一种i)与ii)的反应产物
i)至少一种，优选一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 i)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
ii) 至少一种二异氰酸酯 ii)，
其中i)与ii)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
b)1-90重量%的至少另一种与a)不同的粘合剂组分，优选含羟基或含胺基的粘合剂组分，
c)0-50重量%的至少一种芳族的、脂族的或环脂族的多异氰酸酯，其NCO官能度为至少2，优选 2.8至6，
d)0-5重量%的至少一种催化剂，
其中组分a)-d)之和为100重量%，
e)任选的助剂和/或添加剂，
f)任选的溶剂。
在一个优选的实施方案中，本发明的涂覆剂是指非水性的涂覆剂。在一个特别优选的实施方案中，本文中所使用的术语“非水性的”表明，基于组分a)-f)之和的本发明涂覆剂的水含量不大于3重量%，优选不大于1重量%。在一个特别优选的实施方案中，本发明的涂覆剂不含水。
在本发明的涂覆剂中含有10至99重量%，优选10至70重量%的组分a)，基于组分a)、b)、任选的c)和d)之和。
优选 R、R1、R2和R3同时或彼此独立地表示甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基。
优选n = 0。
R1和R3 优选同时或彼此独立地表示甲基或乙基。
R2 优选甲基或丙基。
优选的是这样的化合物，其中n等于0，R1 和R3 同时或彼此独立地表示甲基或乙基，和R2 同时或彼此独立地表示甲基或丙基。
优选R3 = R1。
优选的是这样的化合物，其中n等于0和R2表示甲基或丙基，和R1表示甲基或乙基和R3 = R1。
非常特别优选的是这样的化合物，其中n等于0，R1和R3表示甲基和R2表示丙基，N-三甲氧基甲硅烷基丙基甲基氨基甲酸酯。
在根据本发明的含有烷氧基硅烷基团的单氨基甲酸酯 i) 与二异氰酸酯 ii) 的反应之后，终产物的NCO含量优选为 < 3重量%，特别优选 < 1重量%，非常特别优选 < 0.2重量%。
根据本发明使用的二异氰酸酯 ii) 可以由任意的芳族的、脂族的、环脂族的和/或(环)脂族的二异氰酸酯组成。在一个优选的实施方案中，本文中使用的术语 “(环)脂族的二异氰酸酯” 是指在分子中同时存在在环上连接的NCO基团和在脂族基团上连接的NCO基团，例如异佛尔酮二异氰酸酯的情况。在一个优选的实施方案中，本文中使用的术语 “环脂族的二异氰酸酯” 是指仅具有直接在环脂族的环上连接的NCO基团的二异氰酸酯，例如二异氰酸根合二环己基甲烷(H12MDI)。
原则上，适合于作为芳族的二异氰酸酯 ii) 的是所有已知的芳族化合物。特别合适的是1,3-和1,4-亚苯基二异氰酸酯、1,5-亚萘基二异氰酸酯、2,6-甲苯二异氰酸酯 (2,6-TDI)、2,4-甲苯二异氰酸酯 (2,4-TDI)、2,4'-二苯基甲烷二异氰酸酯 (2,4'-MDI)、4,4'-二苯基甲烷二异氰酸酯 (4,4'-MDI)、单体的二苯基甲烷二异氰酸酯 (MDI)和低聚的二苯基甲烷二异氰酸酯的混合物 (多-MDI)、苯二亚甲基二异氰酸酯 (MXDI)和四甲基苯二亚甲基二异氰酸酯 (TMXDI)。
有利地，在直链和/或支化的亚烷基中，合适的脂族二异氰酸酯 ii) 具有3至16个碳原子，优选4至12个碳原子。
在环亚烷基中，合适的环脂族的或(环)脂族的二异氰酸酯 ii) 有利地具有4至18个碳原子，优选6至15个碳原子。(环)脂族的二异氰酸酯对于本领域技术人员来说是指同时环上和脂族上连接的NCO基团，例如在异佛尔酮二异氰酸酯的情况。相对地，环脂族的二异氰酸酯是指这样的二异氰酸酯，其仅具有直接连接在环脂族环上的NCO基团，例如H12MDI。
实例是环己烷二异氰酸酯、甲基环己烷二异氰酸酯、乙基环己烷二异氰酸酯、丙基环己烷二异氰酸酯、甲基二乙基环己烷二异氰酸酯、丙烷二异氰酸酯、丁烷二异氰酸酯、戊烷二异氰酸酯、己烷二异氰酸酯、庚烷二异氰酸酯、辛烷二异氰酸酯、壬烷二异氰酸酯、壬烷三异氰酸酯例如4-异氰酸根合甲基-1,8-辛烷二异氰酸酯 (TIN)、癸烷二-和三异氰酸酯、十一烷二-和三异氰酸酯、十二烷二-和三异氰酸酯。同样合适的是4-甲基环己烷-1,3-二异氰酸酯、2-丁基-2-乙基五亚甲基二异氰酸酯、3(4)-异氰酸根合甲基-1-甲基环己基异氰酸酯、2-异氰酸根合丙基环己基异氰酸酯、二异氰酸根合二环己基甲烷 (H12MDI)、1,4-二异氰酸根合-4-甲基戊烷。
优选的二异氰酸酯 ii) 是异佛尔酮二异氰酸酯 (IPDI)、六亚甲基二异氰酸酯(HDI)、2,2'-二环己基甲烷 二异氰酸酯 (2,2'-H12MDI)、2,4'-二环己基甲烷二异氰酸酯(2,4'-H12MDI)、4,4'-二环己基甲烷二异氰酸酯 (4,4'-H12MDI)、2-甲基戊烷二异氰酸酯(MPDI)、戊烷二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)、2,4,4-三甲基六亚甲基二异氰酸酯 (2,4,4-TMDI)、降冰片烷二异氰酸酯 (NBDI)、亚甲基二苯基二异氰酸酯 (MDI)、甲苯胺二异氰酸酯 (TDI)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯 (MXDI)，单独地或以混合物的形式。
特别优选异佛尔酮二异氰酸酯 (IPDI)，六亚甲基二异氰酸酯 (HDI)，4,4'-二异氰酸根合二环己基甲烷、2,4'-二异氰酸根合二环己基甲烷、2,2'-二异氰酸根合二环己基甲烷，单独地或所述异构体的混合物 (H12MDI)，2-甲基戊烷二异氰酸酯 (MPDI)，2,2,4-三甲基六亚甲基二异氰酸酯，2,4,4-三甲基六亚甲基二异氰酸酯以及其混合物 (TMDI)，降冰片烷二异氰酸酯 (NBDI)，MXDI，单独地或以混合物的形式。
非常特别优选使用IPDI、HDI、TMDI、MXDI和H12MDI，单独地或以混合物的形式。
在一个特别优选的实施方案中，所述二异氰酸酯 ii) 是IPDI和/或4,4'-H12MDI和/或HDI和/或2,2,4-TMDI与2,4,4-TMDI的混合物。
当然，也可以使用二异氰酸酯 ii)的混合物。
脲基甲酸酯 a) 的制备通常在无溶剂的情况下或在使用非质子性溶剂的情况下进行，其中所述反应可以不连续地或连续地进行。所述反应在合适的设备中进行，例如搅拌釜、挤出机、静态混合机、捏合室。所述反应可以在室温下，即在15至40℃，特别是15至25℃的温度下进行。然而优选地，使用80至220℃，特别是80至120℃的较高温度。所述反应在不含水的情况下进行。优选地，所述反应在无溶剂的情况下进行。
为了加速所述反应，可以有利地使用在氨基甲酸酯化学中已知的催化剂 C)，例如金属有机化合物，如含锡或锌的化合物，盐，如氯化锌(II)和/或碱。合适的是例如Sn、Bi、Zn和其它金属的羧酸盐，如二月桂酸二丁基锡、辛酸锡、乙基己酸锌、新癸酸铋，叔胺，如1,4-二氮杂双环[2.2.2]辛烷(DABCO)、1,8-二氮杂双环[5.4.0]十一-7-烯 (DBU)、1,5-二氮杂双环[4.3.0]壬-5-烯 (DBN)，三乙胺，脒和胍，以及季铵盐，优选四烷基铵盐，和/或季鏻盐。
本发明的涂覆剂包含作为组分b)的至少另一种不同于a)的粘合剂组分。原则上，作为粘合剂合适的是所有本领域技术人员已知类型的粘合剂，例如热塑性的（即，不可交联的）粘合剂，其通常具有 > 10 000 g/mol 的平均分子量。然而，优选的是具有反应性官能团（具有酸性氢原子，例如羟基或者伯或仲胺基）的粘合剂。所述类型的合适粘合剂例如具有至少一个，但优选两个或更多个羟基。所述粘合剂的其它合适的官能团例如是烷氧基硅烷官能团。
作为具有官能团的粘合剂组分b)，优选使用含有羟基的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯，它们的OH值为20至500 mg KOH/g和平均摩尔质量为250至6000 g/mol。在本发明中特别优选地，使用含有羟基的聚酯或聚丙烯酸酯作为粘合剂组分，它们的OH值为50至250 mg KOH/g和平均分子量为500至6000 g/mol。羟值 (OH值、OHZ) 根据DIN53240-2测定。在该方法中，将样品与乙酸酐在4-二甲基氨基吡啶作为催化剂的存在下反应，其中羟基被乙酰基化。由此，每个羟基产生一个分子的乙酸，而过量乙酸酐的随后水解产生两个分子的乙酸。通过滴定法，由主要值和平行进行的空白值之间的差值确定乙酸的消耗。借助凝胶渗透色谱法 (GPC) 测定分子量。样品的表征在作为洗脱液的四氢呋喃中根据DIN 55672-1进行。
可以作为粘合剂组分b)使用的含有羟基的(甲基)丙烯酸系共聚物可以是具有单体组成的树脂，例如在WO 93/15849 A1 (第8页第25行到第10页第5行) 中描述的。其中，通过成比例地使用作为单体的 (甲基)丙烯酸而调节的(甲基)丙烯酸系共聚物的酸值据信为0至30，优选 0至15 mg KOH/g。(甲基)丙烯酸系共聚物的数均摩尔质量 (通过凝胶渗透色谱法参照聚苯乙烯标准测定) 优选为 2000至20000 g/mol；玻璃化转变温度优选为–40℃至+60℃。通过成比例地使用羟基烷基(甲基)丙烯酸酯而调节的根据本发明待使用的(甲基)丙烯酸系共聚物的羟基含量优选为 20至500 mg KOH/g，特别优选 50至250 mg KOH/g。
根据本发明适合作为粘合剂组分b)的聚酯多元醇是由二元和多元羧酸与二元和多元醇构成的具有单体组成的树脂，如WO 93/15849 A1中描述的。作为聚酯多元醇也可以使用己内酯在低分子量的二元和三元醇上的聚加成产物，例如以商品名CAPA®(Perstorp) 可以获得的。计算确定的数均摩尔质量优选为 500至5000 g/mol，特别优选800至3000 g/mol；平均官能度优选为 2.0至4.0，优选 2.0至3.5。
原则上，作为根据本发明用作粘合剂组分b)的含有氨基甲酸酯基团和含有酯基团的多元醇，也可以使用如在EP 140 186 A1中描述过的那些。优选地，使用这样的含有氨基甲酸酯基团和含有酯基团的多元醇，它们通过HDI、IPDI、三甲基六亚甲基二异氰酸酯(TMDI)或二环己基甲烷二异氰酸酯 (H12MDI) 制备。数均摩尔质量优选为 500-5000 g/mol；平均官能度特别为2.0至3.5。
三烷氧基硅烷官能的粘合剂也适合于用作组分b)。这类树脂可以通过丙烯酸酯或甲基丙烯酸酯单体与丙烯酰基-或甲基丙烯酰基官能的烷基三烷氧基硅烷衍生物 (例如Dynasylan® MEMO，来自Evonik Industries AG) 的共聚获得，例如在WO 92/11328中所述的。替代的合成路径是含羟基的聚醚、聚酯、聚碳酸酯二醇或聚丙烯酸酯与异氰酸根合丙基三烷氧基硅烷的衍生化，例如在WO2008/131715的实施例3和4中所述的。也可以考虑含有氨基的粘合剂，例如氨基丙基三甲氧基硅烷 (例如Dynasylan AMMO，来自Evonik IndustriesAG)、氨基丙基三乙氧基硅烷、氨基甲基三甲氧基硅烷或氨基甲基三乙氧基硅烷。
当然，也可以使用上述粘合剂组分 b) 的混合物。
特别优选的粘合剂组分 b) 是含羟基的聚酯和聚丙烯酸酯，单独地或以混合物的形式。
粘合剂组分 b) 在本发明的粘合剂中的含量优选为1至90重量%，优选20至60重量%，基于组分a)、b)和任选的c)和d)之和。
组分c)
根据本发明使用的多异氰酸酯 c) 可以由任意的芳族的、脂族的、环脂族的和/或(环)脂族的多异氰酸酯组成。
原则上，适合作为芳族的多异氰酸酯 c) 的是所有已知的芳族化合物。特别优选1,3-和1,4-亚苯基二异氰酸酯、1,5-亚萘基二异氰酸酯、2,6-甲苯二异氰酸酯 (2,6-TDI)、2,4-甲苯二异氰酸酯 (2,4-TDI)、2,4'-二苯基甲烷二异氰酸酯 (2,4'-MDI)、4,4'-二苯基甲烷二异氰酸酯 (4,4'-MDI)、单体的二苯基甲烷二异氰酸酯 (MDI)和低聚的二苯基甲烷二异氰酸酯的混合物 (多-MDI)、苯二亚甲基二异氰酸酯 (MXDI)和四甲基苯二亚甲基二异氰酸酯 (TMXDI)。
作为交联剂组分c)使用的脂族的或环脂族的多异氰酸酯 c) 包括至少一种脂族的和/或环脂族的多异氰酸酯，其NCO官能度为至少2，优选 2至6，更优选2.8至6，最优选2至4。本文中使用的术语“NCO官能度”是指相应分子，优选交联剂组分c)平均具有的反应性NCO取代基的数目。
根据本发明作为本发明的组分c) 使用的多异氰酸酯 c) 可以是任意的脂族的、环脂族的和/或(环)脂族的二异氰酸酯。(环)脂族的二异氰酸酯对于本领域技术人员来说是指同时环上和脂族上连接的NCO基团，例如在异佛尔酮二异氰酸酯的情况。相对地，环脂族的二异氰酸酯是指这样的二异氰酸酯，其仅具有直接连接在环脂族环上的NCO基团，例如H12MDI。
适用作本发明的组分c) 的脂族的多异氰酸酯包含直链或支化的亚烷基，其优选具有3至16个碳原子，更优选 4至12个碳原子。合适的环脂族的或(环)脂族的多异氰酸酯c) 包含具有优选 4至18个碳原子，更优选 6至15个碳原子的环亚烷基。合适的二-或多异氰酸酯的实例包括环己烷二异氰酸酯、甲基环己烷二异氰酸酯、乙基环己烷二异氰酸酯、丙基环己烷二异氰酸酯、甲基二乙基环己烷二异氰酸酯、丙烷二异氰酸酯、丁烷二异氰酸酯、戊烷二异氰酸酯、己烷二异氰酸酯、庚烷二异氰酸酯、辛烷二异氰酸酯、壬烷二异氰酸酯、壬烷三异氰酸酯例如4-异氰酸根合甲基-1,8-辛烷二异氰酸酯 (TIN)、癸烷二-和三异氰酸酯、十一烷二-和三异氰酸酯、十二烷二-和三异氰酸酯。同样合适的是4-甲基环己烷-1,3-二异氰酸酯、2-丁基-2-乙基五亚甲基二异氰酸酯、3(4)-异氰酸根合甲基-1-甲基环己基异氰酸酯、2-异氰酸根合丙基环己基异氰酸酯、2,4'-亚甲基双(环己基)二异氰酸酯和/或1,4-二异氰酸根合-4-甲基戊烷。
优选地，作为本发明的组分c) 使用的多异氰酸酯选自异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯 (HDI)、2,2'-二环己基甲烷二异氰酸酯 (2,2'-H12MDI)、2,4'-二环己基甲烷二异氰酸酯 (2,4'-H12MDI)、4,4'-二环己基甲烷二异氰酸酯 (4,4'-H12MDI)、2-甲基戊烷二异氰酸酯 (MPDI)、戊烷二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)、2,4,4-三甲基六亚甲基二异氰酸酯 (2,4,4-TMDI)、降冰片烷二异氰酸酯 (NBDI)、亚甲基二苯基二异氰酸酯 (MDI)、甲苯胺二异氰酸酯 (TDI)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯 (MXDI)，单独地或以混合物的形式使用。
特别优选地，作为本发明的组分c) 使用的多异氰酸酯选自异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯 (HDI)、二异氰酸根合二环己基甲烷 (H12MDI)、2-甲基戊烷二异氰酸酯 (MPDI)、2,2,4-三甲基六亚甲基二异氰酸酯/2,4,4-三甲基六亚甲基二异氰酸酯 (TMDI)、降冰片烷二异氰酸酯 (NBDI)。特别优选IPDI、HDI、TMDI和/或H12MDI，其中IPDI、H12MDI和/或HDI是最优选的多异氰酸酯。
作为本发明的组分c) 也优选使用这样的多异氰酸酯，其可以由所述多异氰酸酯或者它们的混合物通过借助氨基甲酸酯、脲基甲酸酯、脲、缩二脲、脲二酮、酰胺、异氰脲酸酯、碳二亚胺、脲酮亚胺、噁二嗪三酮或亚氨基噁二嗪二酮结构的连接而制备。这样的多异氰酸酯可以商购获得。
特别优选地，作为本发明的组分c) 的是异氰脲酸酯，特别是由IPDI和/或HDI构成的异氰脲酸酯，例如VESTANAT HT 2500 L和VESTANAT T 1890。这类多异氰酸酯可以任选地通过二-或多官能的、H-酸性的组分，例如二-或多元醇和/或二-或多胺额外地扩链或支化。
特别优选地，作为本发明的组分c) 使用这样的异氰脲酸酯，该异氰脲酸酯通过蒸馏分离而不含有残余单体，从而使得多异氰酸酯残余单体的含量为 < 0.5重量%。
在本发明中，可以使用上述二异氰酸酯和/或多异氰酸酯的任意混合物。
如果存在，组分c)在本发明的涂覆剂中的含量为5至50重量%，优选 15至40重量%，基于组分a)、b)、任选的c)和d)之和。
在一个优选的实施方案中，催化剂 d) 在本发明的涂覆剂中的含量为0.1至5重量%，优选 0.2至3重量%，基于组分a)、b)、任选的c)和d)之和。
作为催化剂 d)，可以使用有机羧酸。合适的羧酸的实例特别是水杨酸、苯甲酸、柠檬酸、邻苯二甲酸、对苯二甲酸、间苯二甲酸、十二烷酸、1,12-十二烷二酸和/或抗坏血酸。优选使用水杨酸、柠檬酸或苯甲酸，其中也可以使用所述羧酸的混合物。
作为催化剂 d)，也可以单独地或以混合物的形式使用季铵盐，优选四烷基铵盐，和/或季鏻盐，其中卤素离子、氢氧根离子、醇负离子或有机酸或无机酸负离子作为抗衡离子。
实例包括：四甲基甲酸铵、四甲基乙酸铵、四甲基丙酸铵、四甲基丁酸铵、四甲基苯甲酸铵、四乙基甲酸铵、四乙基乙酸铵、四乙基丙酸铵、四乙基丁酸铵、四乙基苯甲酸铵、四丙基甲酸铵、四丙基乙酸铵、四丙基丙酸铵、四丙基丁酸铵、四丙基苯甲酸铵、四丁基甲酸铵、四丁基乙酸铵、四丁基丙酸铵、四丁基丁酸铵和四丁基苯甲酸铵，和四丁基乙酸鏻、四丁基甲酸鏻和乙基三苯基乙酸鏻、四丁基苯并三唑化鏻、四苯基苯酚化鏻和三己基四癸基癸酸鏻、甲基三丁基氢氧化铵、甲基三乙基氢氧化铵、四甲基氢氧化铵、四乙基氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、四戊基氢氧化铵、四己基氢氧化铵、四辛基氢氧化铵、四癸基氢氧化铵、四癸基三己基氢氧化铵、四-十八烷基氢氧化铵、苯甲基三甲基氢氧化铵、苯甲基三乙基氢氧化铵、三甲基苯基氢氧化铵、三乙基甲基氢氧化铵、三甲基乙烯基氢氧化铵、甲基三丁基甲醇铵、甲基三乙基甲醇铵、四甲基甲醇铵、四乙基甲醇铵、四丙基甲醇铵、四丁基甲醇铵、四戊基甲醇铵、四己基甲醇铵、四辛基甲醇铵、四癸基甲醇铵、四癸基三己基甲醇铵、四-十八烷基甲醇铵、苯甲基三甲基甲醇铵、苯甲基三乙基甲醇铵、三甲基苯基甲醇铵、三乙基甲基甲醇铵、三甲基乙烯基甲醇铵、甲基三丁基乙醇铵、甲基三乙基乙醇铵、四甲基乙醇铵、四乙基乙醇铵、四丙基乙醇铵、四丁基乙醇铵、四戊基乙醇铵、四己基乙醇铵、四辛基甲醇铵、四癸基乙醇铵、四癸基三己基乙醇铵、四-十八烷基乙醇铵、苯甲基三甲基乙醇铵、苯甲基三乙基乙醇铵、三甲基苯基乙醇铵、三乙基甲基乙醇铵、三甲基乙烯基乙醇铵、甲基三丁基苄化铵、甲基三乙基苄化铵、四甲基苄化铵、四乙基苄化铵、四丙基苄化铵、四丁基苄化铵、四戊基苄化铵、四己基苄化铵、四辛基苄化铵、四癸基苄化铵、四癸基三己基苄化铵、四-十八烷基苄化铵、苯甲基三甲基苄化铵、苯甲基三乙基苄化铵、三甲基苯基苄化铵、三乙基甲基苄化铵、三甲基乙烯基苄化铵、四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、四辛基氟化铵、苯甲基三甲基氟化铵、四丁基氢氧化鏻、四丁基氟化鏻、四丁基氯化铵、四丁基溴化铵、四丁基碘化铵、四乙基氯化铵、四乙基溴化铵、四乙基碘化铵、四甲基氯化铵、四甲基溴化铵、四甲基碘化铵、苯甲基三甲基氯化铵、苯甲基三乙基氯化铵、苯甲基三丙基氯化铵、苯甲基三丁基氯化铵、甲基三丁基氯化铵、甲基三丙基氯化铵、甲基三乙基氯化铵、甲基三苯基氯化铵、苯基三甲基氯化铵、苯甲基三甲基溴化铵、苯甲基三乙基溴化铵、苯甲基三丙基溴化铵、苯甲基三丁基溴化铵、甲基三丁基溴化铵、甲基三丙基溴化铵、甲基三乙基溴化铵、甲基三苯基溴化铵、苯基三甲基溴化铵、苯甲基三甲基碘化铵、苯甲基三乙基碘化铵、苯甲基三丙基碘化铵、苯甲基三丁基碘化铵、甲基三丁基碘化铵、甲基三丙基碘化铵、甲基三乙基碘化铵、甲基三苯基碘化铵和苯基三甲基碘化铵、甲基三丁基氢氧化铵、甲基三乙基氢氧化铵、四甲基氢氧化铵、四乙基氢氧化铵、四丙基氢氧化铵、四丁基氢氧化铵、四戊基氢氧化铵、四己基氢氧化铵、四辛基氢氧化铵、四癸基氢氧化铵、四癸基三己基氢氧化铵、四-十八烷基氢氧化铵、苯甲基三甲基氢氧化铵、苯甲基三乙基氢氧化铵、三甲基苯基氢氧化铵、三乙基甲基氢氧化铵、三甲基乙烯基氢氧化铵、四甲基氟化铵、四乙基氟化铵、四丁基氟化铵、四辛基氟化铵和苯甲基三甲基氟化铵。这些催化剂可以单独地或以混合物的形式添加。优选地，使用四乙基苯甲酸铵和四丁基氢氧化铵。
作为催化剂 d)，也可以使用具有螯合物配体的金属配合物。螯合物配体是指具有至少两个可以与金属原子或离子配位的官能团的有机化合物。可以使用例如铝-和锆-螯合物配合物作为催化剂，例如在US-P 4,772,672 A中描述的那些。优选的金属螯合物是基于锌、锂、锡、铝、锆、钛和/或硼的螯合物，例如乙基乙酰乙酸铝、乙基乙酰乙酸锆、乙酰丙酮锌、乙酰丙酮锂和乙酰丙酮锡，单独地或以混合物的形式。优选使用乙酰丙酮锌。
此外，作为催化剂 d)可以考虑季铵-乙酰丙酮化物或季鏻-乙酰丙酮化物。这样的催化剂的实例是四甲基铵-乙酰丙酮化物、四乙基铵-乙酰丙酮化物、四丙基铵-乙酰丙酮化物、四丁基铵-乙酰丙酮化物、苯甲基三甲基铵-乙酰丙酮化物、苯甲基三乙基铵-乙酰丙酮化物、四甲基鏻-乙酰丙酮化物、四乙基鏻-乙酰丙酮化物、四丙基鏻-乙酰丙酮化物、四丁基鏻-乙酰丙酮化物、苯甲基三甲基鏻-乙酰丙酮化物、苯甲基三乙基鏻-乙酰丙酮化物。特别优选使用四乙基铵-乙酰丙酮化物和四丁基铵-乙酰丙酮化物。当然也可以使用这些催化剂的混合物。
适合作为催化剂 d) 的还有铝、锆、钛和/或硼的醇盐和/或铝、锆、钛和/或硼的酯。
也适合作为催化剂的是碱性物质，例如胍和脒和叔胺。它们的实例是四甲基胍、二氮杂双环十一烯 (DBU)、二氮杂双环壬烯 (DBN)和二氮杂双环辛烷 (DABCO)。
作为催化剂 d)，为了催化氨基甲酸酯反应，也可以使用在PUR技术领域中证明有利的那些催化剂，例如Sn(IV)、Sn(II)、Zn和Bi有机化合物，或者金属有机催化剂，例如二月桂酸二丁基锡、辛酸锡、乙基己酸锌、新癸酸铋，或叔胺，例如1,4-二氮杂双环[2.2.2]辛烷。然而根据本发明，用于氨基甲酸酯反应的这类催化剂仅以与其它本发明催化剂的混合物的形式使用。优选使用乙基己酸锌。
作为催化剂 d) 也可以使用含磷的，优选含磷和含氮的催化剂。在此，也可以使用由两种或更多种不同的催化剂构成的混合物。合适的含磷催化剂的实例是取代的膦酸二酯和二膦酸二酯，优选选自非环状的膦酸二酯、环状的膦酸二酯、非环状的二膦酸二酯和环状的二膦酸二酯。这类催化剂例如描述在DE-A 102005045228中。
作为催化剂 d)，也可以优选使用胺封端的（aminblockiert）磷酸酯和特别优选胺封端的磷酸乙基己基酯和胺封端的磷酸苯基酯。使磷酸酯封端的胺的实例特别是叔胺，例如三乙胺。特别优选地，使用在100至160℃的固化温度下具有好的催化剂效力的叔胺用于使得磷酸酯封端。使用胺封端的特定磷酸催化剂也是商购可得的 (例如Nacure产品，来自King Industries)。例如，King Industries公司的商品名Nacure 4167可以是基于胺封端的磷酸偏酯的特别合适的催化剂。
作为催化剂 d)，也可以使用未封端或封端的形式的有机磺酸。原则上，作为磺酸合适的是任何有机磺酸，优选对甲苯磺酸和十二烷基苯磺酸。对于热交联的，即在100℃以上交联的涂料体系，根据本发明也优选使用以胺中和的形式的这些磺酸。根据本发明，也可以使用潜性的、非可离子化的磺酸衍生物，它们在100℃以上才释放磺酸，例如磺酸在含有环氧化物的组分上的加合物，如在DE-A 23 56768所述的。三氟甲磺酸的盐 (三氟甲磺酸盐) 也是合适的基于磺酸的催化剂。
优选使用的催化剂 d) 选自四乙基苯甲酸铵、四丁基氢氧化铵、四乙基铵-乙酰丙酮化物、四丁基铵-乙酰丙酮化物、二月桂酸二丁基锡、乙酰丙酮锌、乙基己酸锌。
在本发明的涂覆剂中的催化剂 d) 可以单独地由上述的可选物质组成，也可以使用所述催化剂的任意混合物。
本发明的涂覆剂还可以以通常的浓度包含在漆料技术中已知的助剂和/或添加剂e)，例如稳定剂、光保护剂、催化剂、额外的交联剂、填料、颜料、流控剂或流变助剂，例如所谓的“流挂控制剂”，微凝胶或热解二氧化硅或纳米颗粒，例如在EP 1204701 B1中所述的。此外，组分e) 可以包含如在漆料化学中已知的额外的交联剂，例如以三聚氰胺树脂、苯并胍胺树脂的形式，氨基甲酸酯官能的组分或封端的多异氰酸酯。如果需要，也可以在本发明的涂覆剂的组分e) 中并入在漆料技术中常见的无机或有机的彩色颜料和/或效果颜料。
在一个优选的实施方案中，根据本发明的涂覆剂是不含颜料的体系，即透明漆料体系。在这种情况下，在本发明的涂覆剂中的组分e)的含量优选可以为0.5至8重量%，更优选 1至6重量%，基于组分a)、b)、任选的c)和d)之和。
在另一个优选的实施方案中，根据本发明的涂覆剂是彩色的涂料体系。在这种情况下，在本发明的涂覆剂中作为组分e) 的颜料和填料的含量可以为10至200重量%，基于组分a)、b)、任选的c)和d)之和。
此外，根据本发明的涂覆剂可以包含有机溶剂作为组分f)。合适的溶剂例如是酮、醇、酯或芳烃。
在本发明的涂覆剂中的组分f) 的含量优选为20至150重量%，更优选 30至60重量%，基于组分a)、b)、任选的c)和d)之和。
本发明的涂覆剂的制备可以通过混合上述的组分进行。该混合可以通过本领域技术人员已知的混合器进行，例如不连续地在搅拌容器、溶解器、珠磨机、辊磨机等中，或者连续地例如使用静态混合器。
本发明还涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂在漆料组合物和胶粘剂组合物和金属涂料组合物中的用途。
本发明还涉及烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂在用于金属、玻璃、塑料、木材、MDF (中密度纤维板) 或皮革基材或其它耐热基底的涂料组合物和漆料组合物中的用途。
本发明还涉及根据本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂在用于粘合金属、塑料、玻璃、木材、MDF或皮革基材或其它耐热基底的胶粘剂组合物中的用途。
同样地，本发明涉及金属涂料组合物，特别是用于汽车车身、摩托车和自行车、建筑物部件和家用设备，木材涂料组合物、MDF涂料、玻璃涂料组合物、皮革涂料组合物和塑料涂料组合物。
本发明接下来通过下面的非受限的实施例阐述，从中可以看出本发明的其它特征、实施方案、方面和优点。
具体实施方式
原材料：
Vestanat® EP-UPMS：三甲氧基甲硅烷基丙基甲基氨基甲酸酯 (Evonik ResourceEfficiency GmbH)
Vestanat® IPDI：异佛尔酮二异氰酸酯 (Evonik Resource Efficiency GmbH)
Vestanat® TMDI：2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)和2,4,4-三甲基六亚甲基二异氰酸酯的混合物 (Evonik Resource Efficiency GmbH)
Vestanat® HT 2500/100：六亚甲基-1,6-二异氰酸酯，均聚物 (异氰脲酸酯类型)(Evonik Resource Efficiency GmbH)
Vestanat® EP Cat 11 B：在丁醇中的四乙基苯甲酸铵 (Evonik ResourceEfficiency GmbH)
Tegoglide® 410：基于聚醚硅氧烷共聚物的滑动和防粘连添加剂 (Evonik ResourceEfficiency GmbH)
Vestanat® EP-M60：直链的、短链的、硅烷官能化的交联剂 (Evonik ResourceEfficiency GmbH)
Vestanat® EP-M95：支化的、短链的、硅烷官能化的交联剂 (Evonik ResourceEfficiency GmbH)
Vestanat® EP-M120：直链的、长链的、硅烷官能化的交联剂 (Evonik ResourceEfficiency GmbH)
Setalux® 1760 VB-64：聚丙烯酸酯多元醇，Nuplex Resins B.V.
Tinuvin® 292：空间位阻的胺，光保护剂；BASF SE
Tinuvin® 900：UV吸收剂；BASF SE。
制备
实施例1
烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂，组分1a)
在具有回流冷凝器的三颈烧瓶中，预先加入340.2 g的Vestanat® EP-UPMS、0.3 g的乙基己酸锌(II)和159.7 g的Vestanat® IPDI，填充氮气和在搅拌下加热至100℃。在加热20小时之后，获得的NCO含量为1.4重量% NCO。然后加入10.84 g的丁醇和在100℃下加热1小时直至达到NCO含量为 < 0.1重量% NCO。在冷却至室温之后，获得透明液体的烷氧基硅 烷官能化的、含有脲基甲酸酯的粘合剂，组分1a，其粘度为14.3 Pas (在23℃下)。
实施例2
烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂，组分2a)
在具有回流冷凝器的三颈烧瓶中，预先加入474.6 g的Vestanat® EP-UPMS、0.22 g的乙基己酸锌(II)和211.8 g的Vestanat® TMDI，填充氮气和在搅拌下加热至100℃。在加热24小时之后，获得的NCO含量为0.8重量% NCO。然后加入10.35 g的丁醇在65℃下加热3小时直至达到NCO含量为 < 0.1重量% NCO。在冷却至室温之后，获得透明液体的烷氧基硅烷官 能化的、含有脲基甲酸酯的粘合剂，组分2a，其粘度为1170 mPas (在23℃下)。
对比例3A
烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂，组分3a (对比例)
在具有回流冷凝器的三颈烧瓶中，预先加入44.3 g的Vestanat® EP-UPMS、0.01 g的乙基己酸锌(II)和35.7 g的Vestanat® HT 2500/100，填充氮气和在搅拌下加热至100℃直至达到NCO含量为 < 0.1重量%。然后，为了降低粘度，趁热加入20 g的乙酸丁酯。如此获得的烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂，组分3a是透明液体，其粘度为750mPas (在23℃下)。
透明漆料
为了配制本发明的透明漆料和对比例，将在表1中所述的组合物的组分在加工前直接彼此混合。
所述配制品的粘度为大约20秒，作为在23℃下在DIN 4 杯中的流出时间测定。
表2显示了组合物I-VI的可使用时间。所述可使用时间如下测定：
将待测定的液体样品 (至少70 ml) 装入100 ml的玻璃小瓶中，并且在垂直方向上配有金属棒，该金属棒的末端带有直径约2cm的圆形金属小片并且浸入样品中。该玻璃小瓶配有孔盖和将金属棒夹紧在凝胶化时间测量仪 (Techne Gelation Timer)。样品目前处于调节至室温 (23℃) 的水箱 (Lauda 恒温器型 BK2)中。在样品中的金属棒以恒定的节奏振荡式地上下移动，直至样品的阻力大于凝胶化时间测量仪的作用力。在这种情况下，金属棒保持插入状，所述样品“凝胶化”。金属棒的振荡式移动的开始和结束之间的时间段在凝胶化测量仪的显示器上显示出来。
表2：组合物I-VI的可使用时间
| 透明漆料体系 | 可使用时间 (h) |
| I | 18.8 |
| II | 14.0 |
| III (对比) | 5.8 |
| IV (对比例) | 4.3 |
| V (对比例) | 4.0 |
| VI (对比例) | 2.0 |
从表2给出的可使用时间可以看出，本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂 I-II 相比于对比例 III – VI 具有明显更长的可使用时间。从现有技术 (对比例 IV – VI) 不会期望，在使用本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂 I-II的情况下，可使用时间延长四倍。
为了测定机械表征数据，将所有漆料以120 µm刮涂到磷化钢板 (ChemetallGardobond 26S/60/OC) 上，并且在160℃下固化22分钟。
表3：在160℃ (22 min)下固化之后的组合物I-III的漆料性能
包含本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂组分 1和2 的涂层I和II的漆料性能显现出大约相同的摆锤硬度和MEK耐受性，但比对比例III改进的粘合性（交叉线）。特别是在包含三倍官能化的对比例3的配方III的情况下，由于更高的交联度而会期望相比于包含本发明的烷氧基硅烷官能化的、含有脲基甲酸酯的粘合剂组分 1和2 的涂料I和II的更高的硬度。
Claims (20)
1.烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂，其包含
a)作为粘合剂组分，10-99重量%的至少一种i)与ii)的反应产物
i)至少一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 i)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
ii) 至少一种二异氰酸酯 ii)，
其中i)与ii)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
b)1-90重量%的至少另一种与a)不同的粘合剂组分，优选含羟基或含胺基的粘合剂组分，
c)0-50重量%的至少一种芳族的、脂族的或环脂族的多异氰酸酯，其NCO官能度为至少2，优选 2.8至6，
d)0-5重量%的至少一种催化剂，
其中组分a)-d)之和为100重量%，
e)任选的助剂和/或添加剂，
f)任选的溶剂。
2.烷氧基硅烷官能化的、含有脲基甲酸酯的涂覆剂，其由a)至f)组成：
a)作为粘合剂组分，10-99重量%的至少一种i)与ii)的反应产物
i)至少一种含有烷氧基硅烷基团的式1的单氨基甲酸酯 i)
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3 式1，
其中R、R1、R2和R3彼此独立地表示具有1-8个碳原子的烃基，其中它们可以是直链的、支化的或环状的，或者可以相互成环，和n等于0-2，
与
ii) 至少一种二异氰酸酯 ii)，
其中i)与ii)的摩尔比为3:1至1.5:1，优选2.5:1至1.8:1，特别优选 2:1；
b)1-90重量%的至少另一种与a)不同的粘合剂组分，优选含羟基或含胺基的粘合剂组分,
c)0-50重量%的至少一种芳族的、脂族的或环脂族的多异氰酸酯，其NCO官能度为至少2，优选 2.8至6，
d)0-5重量%的至少一种催化剂，
其中组分a)-d)之和为100重量%，
e)任选的助剂和/或添加剂，
f)任选的溶剂。
3.根据权利要求1或2的涂覆剂，其特征在于，R、R1、R2 和R3同时或彼此独立地表示甲基、乙基、正丙基、异丙基、正丁基、仲丁基或叔丁基。
4.根据前述权利要求至少一项的涂覆剂，其特征在于，n等于0，R1 和R3 同时或彼此独立地表示甲基或乙基，和R2同时或彼此独立地表示甲基或丙基。
5.根据前述权利要求至少一项的涂覆剂，其特征在于，n等于0和R2表示甲基或丙基，和R1表示甲基或乙基和R3 = R1 。
6.根据前述权利要求至少一项的涂覆剂，其特征在于，n等于0，R1 和R3 表示甲基和R2表示丙基。
7.根据前述权利要求至少一项的涂覆剂，其特征在于，所述二异氰酸酯 ii) 选自异佛尔酮二异氰酸酯 (IPDI)、六亚甲基二异氰酸酯 (HDI)、2,2'-二环己基甲烷二异氰酸酯(2,2'-H12MDI)、2,4'-二环己基甲烷二异氰酸酯 (2,4'-H12MDI)、4,4'-二环己基甲烷二异氰酸酯 (4,4'-H12MDI)、2-甲基戊烷二异氰酸酯 (MPDI)、戊烷二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)、2,4,4-三甲基六亚甲基二异氰酸酯 (2,4,4-TMDI)、降冰片烷二异氰酸酯 (NBDI)、亚甲基二苯基二异氰酸酯 (MDI)、甲苯胺二异氰酸酯(TDI)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯 (MXDI)，单独地或以混合物的形式。
8.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是含羟基和/或含胺基的粘合剂。
9.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是含羟基的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯，它们的OH值为20至500 mg KOH/g和平均摩尔质量为250至6000 g/mol，单独地或以混合物的形式。
10.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是含羟基的聚酯或聚丙烯酸酯，它们的OH值为50至250 mg KOH/g和平均分子量为500至6000 g/mol，单独地或以混合物的形式。
11.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是异氰酸根合三烷氧基硅烷和一元或多元醇的至少一种加合物。
12.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是含羟基的聚醚、聚酯、聚碳酸酯二醇或聚丙烯酸酯与异氰酸根合丙基三烷氧基硅烷的至少一种衍生物，单独地或以混合物的形式。
13.根据前述权利要求至少一项的涂覆剂，其特征在于，所述粘合剂b)是氨基丙基三乙氧基硅烷、氨基甲基三甲氧基硅烷或氨基甲基三乙氧基硅烷，单独地或以混合物的形式。
14.根据前述权利要求至少一项的涂覆剂，其特征在于，所述组分c)是选自如下的多异氰酸酯：异佛尔酮二异氰酸酯 (IPDI)、六亚甲基二异氰酸酯 (HDI)、2,2'-二环己基甲烷二异氰酸酯 (2,2'-H12MDI)、2,4'-二环己基甲烷二异氰酸酯 (2,4'-H12MDI)、4,4'- 二环己基甲烷二异氰酸酯 (4,4'-H12MDI)、2-甲基戊烷二异氰酸酯 (MPDI)、戊烷二异氰酸酯、2,2,4-三甲基六亚甲基二异氰酸酯 (2,2,4-TMDI)、2,4,4-三甲基六亚甲基二异氰酸酯 (2,4,4-TMDI)、降冰片烷二异氰酸酯 (NBDI)、亚甲基二苯基二异氰酸酯 (MDI)、甲苯胺二异氰酸酯 (TDI)、四甲基苯二亚甲基二异氰酸酯 (TMXDI)、苯二亚甲基二异氰酸酯 (MXDI)，单独地或以混合物的形式。
15.根据前述权利要求至少一项的涂覆剂，其特征在于，所述组分c)是异氰脲酸酯，特别由IPDI和/或HDI构成。
16.根据前述权利要求至少一项的涂覆剂，其特征在于，所述催化剂 d) 选自金属羧酸盐，叔胺，脒，胍，季铵盐，四烷基铵盐，季鏻盐，金属-乙酰丙酮化物，季铵-乙酰丙酮化物，季鏻-乙酰丙酮化物，羧酸，铝-醇盐、锆-醇盐、钛-醇盐和/或硼-醇盐和/或其酯，含有磷和氮的催化剂，磺酸，单独地或以混合物的形式。
17.根据前述权利要求至少一项的涂覆剂，其特征在于，所述催化剂 d) 选自四乙基苯甲酸铵、四丁基氢氧化铵、四乙基铵-乙酰丙酮化物、四丁基铵-乙酰丙酮化物、二月桂酸二丁基锡、乙酰丙酮锌和乙基己酸锌。
18.根据前述权利要求至少一项的涂覆剂，其特征在于，所述添加剂 e) 选自溶剂、稳定剂、光保护剂、额外的交联剂、填料、颜料、流控剂或流变助剂，单独地或以混合物的形式。
19.通过混合组分a)-f)制备根据前述权利要求1-18至少一项的涂覆剂的方法。
20.根据前述权利要求至少一项的涂覆剂的用途，用在漆料组合物、胶粘剂组合物、密封剂组合物和金属涂料组合物中。
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| EP16176309.9 | 2016-06-27 | ||
| EP16176309.9A EP3263616B8 (de) | 2016-06-27 | 2016-06-27 | Alkoxysilan-funktionalisierte allophanat-haltige beschichtungsmittel |
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| EP (1) | EP3263616B8 (zh) |
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| CN (1) | CN107540807A (zh) |
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| JP6729320B2 (ja) * | 2016-11-21 | 2020-07-22 | 信越化学工業株式会社 | 有機ケイ素化合物を含む組成物並びにこれを含む塗料および接着剤 |
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| JP2018003016A (ja) | 2018-01-11 |
| BR102017013926A2 (pt) | 2018-05-02 |
| MX2017008394A (es) | 2018-09-10 |
| US10093826B2 (en) | 2018-10-09 |
| US20170369736A1 (en) | 2017-12-28 |
| EP3263616B1 (de) | 2019-12-04 |
| EP3263616A1 (de) | 2018-01-03 |
| EP3263616B8 (de) | 2020-01-15 |
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Application publication date: 20180105 |