CN108137777A - 包含基于烷氧基硅烷烷基异氰酸酯的单脲基甲酸酯的涂料 - Google Patents
包含基于烷氧基硅烷烷基异氰酸酯的单脲基甲酸酯的涂料 Download PDFInfo
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- CN108137777A CN108137777A CN201680062770.6A CN201680062770A CN108137777A CN 108137777 A CN108137777 A CN 108137777A CN 201680062770 A CN201680062770 A CN 201680062770A CN 108137777 A CN108137777 A CN 108137777A
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- Prior art keywords
- coating
- ammonium
- adhesive
- component
- methyl
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- 238000000576 coating method Methods 0.000 title claims abstract description 61
- 239000011248 coating agent Substances 0.000 title claims abstract description 59
- -1 alkoxy silane alkyl isocyanate Chemical class 0.000 title claims abstract description 54
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 13
- 239000012948 isocyanate Substances 0.000 title abstract description 12
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 title abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 37
- 239000000853 adhesive Substances 0.000 claims description 32
- 230000001070 adhesive effect Effects 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 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 9
- 229920002635 polyurethane Polymers 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
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
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- 239000002904 solvent Substances 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
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- 150000003839 salts Chemical class 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- 239000003431 cross linking reagent Substances 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
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 150000005621 tetraalkylammonium salts Chemical class 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
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 claims description 2
- 229940070721 polyacrylate Drugs 0.000 claims 3
- 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 1
- 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 1
- 125000003277 amino group Chemical group 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 23
- 239000002585 base Substances 0.000 description 21
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 239000002253 acid Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 8
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 8
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 7
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- UCAHIIZBPCASHX-UHFFFAOYSA-N CC[N+](CC)(CC)CC1=CC=CC=C1.N Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1.N UCAHIIZBPCASHX-UHFFFAOYSA-N 0.000 description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 229920006243 acrylic copolymer Polymers 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 239000008199 coating composition Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 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
- 239000000126 substance Substances 0.000 description 4
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
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- 150000001732 carboxylic acid derivatives Chemical class 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
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- 229910052744 lithium Inorganic materials 0.000 description 3
- 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 3
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
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Abstract
本发明涉及包含基于烷氧基硅烷烷基异氰酸酯的新型单脲基甲酸酯的涂料、制造方法和用途。
Description
本发明涉及包含基于烷氧基硅烷烷基异氰酸酯的新型单脲基甲酸酯的涂料、制造方法和用途。
聚氨酯已确立作为漆料、胶粘剂、密封剂和塑料体系的高品质成分几十年。在此,额外的烷氧基硅烷基团可以在网络密度、耐化学品性和耐刮性方面起重要作用,主要通过形成硅氧烷结构。此类体系也是已知。
既具有烷氧基硅烷基团也具有异氰酸酯基团的分子提供了通过一种组分引入两种所述官能性,即硅氧烷和聚氨酯基团的可能性。此类物质,例如异氰酸根合烷基三烷氧基硅烷也已使用很久。由这些物质可以通过与多元醇反应而制造无异氰酸酯的湿固化型交联剂。
原则上,此类“SiPUR”(含烷氧基硅烷的聚氨酯)可以与其它异氰酸酯反应产生脲基甲酸酯,以改进特定的材料性能,例如粘度。
例如DE102005041953A1描述了平均分子量为3000-20000 g/mol的多元醇与过量的异氰酸根合丙基三甲氧基硅烷的反应,以使得在形成聚氨酯之后进行脲基甲酸酯反应。
在DE102005041954A1中,向来自多元醇和二异氰酸酯(例如IPDI,异佛尔酮二异氰酸酯)的聚氨酯加入异氰酸根合丙基三甲氧基硅烷并加热直至形成脲基甲酸酯结构。
EP2089444A1要求保护含脲基甲酸酯的聚氨酯,其除了不饱和官能性外还具有含硅烷基团的组分。
在EP2089445A1中看起来也类似;但是在此,这些聚氨酯还必须额外地含有分散活性的组分,以将其变得与水相容(wassergängig)。
US20140097392A1中也谈及了含脲基甲酸酯和烷氧基硅烷的聚合物,其在这一情况中与染料混合。
J. Kozakiewicz等人在Progress in Organic Coatings 72 (2011) 120-130中发表了用于多异氰酸酯的含硅烷的封端剂,其通过脲基甲酸酯基团引入。显然需要带有烷氧基硅烷基团的其它化合物尤其用于耐刮应用。但是,所有迄今实例的共同点是,在此始终是既具有高粘度也难以清洁或分离的聚合物和/或聚氨酯。
本发明的目的是提供包含具有耐刮性能的带有烷氧基硅烷基团的新型化合物的涂料,其不具有现有技术的缺点,但特别是易于制造、具有低粘度并通过较少支出就可清洁。
令人惊讶地已发现,由异氰酸酯改性的含烷氧基硅烷基团的单氨基甲酸酯构成的单脲基甲酸酯具有所需性能。
本发明的主题是包含下列组分的涂料:
A) 至少一种具有式1的含脲基甲酸酯的化合物:
其中R、R1-R6彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m和n彼此独立地是0-2,
B) 至少一种粘合剂,优选含羟基的粘合剂,
C) 任选的至少一种脂族或脂环族的多异氰酸酯,其具有至少2,优选2.8至6的NCO官能度,
D) 任选的至少一种催化剂,
E) 任选的辅助剂和/或添加剂,
F) 任选的溶剂。
优选地,m和n是0。
R1和R5彼此独立地优选为甲基或乙基。
R2和R4彼此独立地优选为甲基或丙基。
更优选地,R1 = R5且R2 = R4。
优选为m和n是0、R1和R5是甲基或乙基且R2和R4是甲基或丙基的化合物。
非常特别优选为m和n是0、R1 = R5 =甲基且R2 = R4 =丙基的化合物。
具有式1的单脲基甲酸酯通过A)与B)的反应制造:
其中R、R1-R6彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m和n彼此独立地是0-2,
含烷氧基硅烷基团的异氰酸酯A)具有式2:
R6 m (OR5)3-mSi-R4-NCO
其中R6、R5和R4彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m是0-2。
优选地,m = 0。
R4优选为甲基或丙基。
R5优选为甲基或乙基。
优选为m是0且R4是甲基或丙基且R5是甲基或乙基的化合物。
特别优选为异氰酸根合丙基三甲氧基硅烷。
含烷氧基硅烷的单氨基甲酸酯B)具有式3:
Rn (OR1)3-n Si-R2-NH-(C=O)-OR3
其中R、R1、R2和R3各自独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且n是0-2。
优选地,n = 0。
R1优选是甲基或乙基。
R2优选是甲基或丙基。
优选地,R3 = R1。
优选为n是0且R2是甲基或丙基且R1是甲基或乙基且R3 = R1的化合物。
特别优选为N-三甲氧基甲硅烷基丙基氨基甲酸甲酯。
所述单脲基甲酸酯的制造通常在无溶剂的情况下或在使用非质子溶剂的情况下进行,其中该反应可以不连续或连续地进行。该反应在合适的装置,例如搅拌釜、挤出机、静态混合机、捏合室中进行。该反应可以在室温下,即在20至22℃的温度下进行,但是优选使用80至220℃,更优选80至120℃的更高温度。为了加速该反应,可以有利地使用氨基甲酸酯化学中已知的催化剂,例如金属有机化合物,如含锡或锌的化合物、盐,例如氯化锌(II)和/或碱。合适的是例如Sn、Bi、Zn和其它金属的羧酸盐, 例如二月桂酸二丁基锡、辛酸锡、新癸酸铋、叔胺例如1,4-二氮杂双环[2.2.2]辛烷(DABCO)、三乙胺、脒和胍、季铵盐,优选四烷基铵盐,和/或季鏻盐。可考虑的催化剂包括金属乙酰丙酮化物。对此的实例是单独或混合物形式的乙酰丙酮锌、乙酰丙酮锂、乙酰丙酮铁和乙酰丙酮锡。优选地使用乙酰丙酮锌。可考虑的催化剂此外是季铵乙酰丙酮化物或季鏻乙酰丙酮化物。优选是乙基己酸锌。该反应在排除水的情况下进行。优选地,该反应在无溶剂的情况下进行。
本发明的涂料优选基本上由组分A)、B)、C)、D)和E)构成。在一个优选的实施方案中,这是指组分A)、B)、C)、D)和E)的总和以增大优选的顺序占所述涂料的至少45、50、55、60、65、70、75、80、85、90、92、94、96、98或99重量%。
在一个优选的实施方案中,本发明的涂料是非水性涂料。在一个特别优选的实施方案中,本文所用的术语“非水性”是指本发明的涂料基于组分A)、B)、C)、D)和E)的总和计具有不大于3重量%,优选不大于1重量%的水含量。在一个最优选的实施方案中,本发明的涂料不含水。
组分A)以10至99重量%,优选10至70重量%包含在本发明的涂料中,基于组分A)、B)和C)的总和计。
用作交联剂组分的脂族或脂环族多异氰酸酯C)包含至少一种脂族和/或脂环族多异氰酸酯,其具有至少2,优选2至6,更优选2.8至6,更优选2至4的NCO官能度。在一个优选的实施方案中,此处所用的术语“NCO官能度”理解为是指所涉分子,优选交联剂组分C)平均具有的反应性NCO取代基的数目。
根据本发明使用的多异氰酸酯可以是任意脂族、脂环族和/或脂(环)族二异氰酸酯。在一个优选的实施方案中,此处所用的术语“脂(环)族二异氰酸酯”理解为是指在一个分子中同时存在与环键合的NCO基团和与脂族基团键合的NCO基团,如例如在异佛尔酮二异氰酸酯的情况中。在一个优选的实施方案中,此处所用的术语“脂环族二异氰酸酯”理解为是指仅具有与脂环族的环直接键合的NCO基团的二异氰酸酯,例如二异氰酸根合二环己基甲烷(H12MDI)。
适合用作多异氰酸酯C)的脂族二异氰酸酯包括具有优选3至16个碳原子,更优选4至12个碳原子的直链或支化的亚烷基。合适的脂环族或脂(环)族二异氰酸酯包括具有优选4至18个碳原子,更优选6至15个碳原子的亚环烷基。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。
用作多异氰酸酯的二异氰酸酯优选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)。特别优选是IPDI、HDI、TMDI和/或H12MDI,其中IPDI、H12MDI和/或HDI代表最优选的多异氰酸酯。
特别优选地,使用可由所述二异氰酸酯或其混合物借助氨基甲酸酯、脲基甲酸酯、脲、双缩脲、脲二酮、酰胺、异氰脲酸酯、碳二亚胺、脲酮亚胺、噁二嗪三酮或亚氨代噁二嗪二酮结构通过连接而制成的多异氰酸酯。此类多异氰酸酯是商购可得的。特别合适的是异氰脲酸酯,其特别来自IPDI和/或HDI,例如VESTANAT HT 2500 L和VESTANAT T 1890。这类多异氰酸酯可以是任选通过二-或多官能H酸性组分,例如二元或多元醇和/或二或多胺而额外地增链或支化的。根据本发明优选使用的这些通过蒸馏分离而不含残余单体,以使得二异氰酸酯残余单体含量为< 0.5重量%。
在本发明的范围中,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)以5至50重量%,优选15至40重量%包含在本发明的涂料中,基于组分A)、B)和C)的总和计。例如,C)以50重量%包含在本发明的涂料中,基于组分A)、B)和C)的总和计,如果包含25 g A)、12.5 g B)和12.5 g C)。组分C)在本发明的涂料中的量取决于组分B)的可与多异氰酸酯化学交联的基团——通常OH基团——的含量。组分C)的多异氰酸酯基团与组分B)的OH基团的摩尔比为0.3:1至2:1,优选0.5:1至1.5:1,更优选0.7:1至1.3:1。
本发明的涂料包含至少一种粘合剂作为组分B)。原则上适合作为粘合剂的是本领域技术人员已知的所有类型的粘合剂,例如热塑性,即不可交联的粘合剂,其通常具有>10000 g/mol的平均分子量。但是,优选的粘合剂是具有包含酸性氢原子,例如羟基或伯或仲胺基团的反应性官能团的那些。所述类型的合适粘合剂具有例如至少一个,但优选两个或更多个羟基。粘合剂的此外合适的官能团是例如烷氧基硅烷官能性。优选地使用异氰酸根合三烷氧基硅烷和一元或多元醇的加合物,优选3-异氰酸根合丙基三甲氧基硅烷、3-异氰酸根合丙基三乙氧基硅烷、3-异氰酸根合丙基三异丙氧基硅烷、2-异氰酸根合乙基三甲氧基硅烷、2-异氰酸根合乙基三乙氧基硅烷、2-异氰酸根合乙基三异丙氧基硅烷、4-异氰酸根合丁基三甲氧基硅烷、4-异氰酸根合丁基三乙氧基硅烷、4-异氰酸根合丁基三异丙氧基硅烷、异氰酸根合甲基三甲氧基硅烷、异氰酸根合甲基三乙氧基硅烷和/或异氰酸根合甲基三异丙氧基硅烷的加合物。
作为具有官能团的粘合剂,优选使用具有20至500 mg KOH/g的OH值和250至6000g/mol的平均摩尔质量的含羟基的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯。在本发明的范围中,特别优选使用具有50至250 mg KOH/g的OH值和500至6000 g/mol的平均分子量的含羟基的聚酯或聚丙烯酸酯作为粘合剂组分。羟基值(OH值,OHN)根据DIN 53240-2测定。在这一方法中,将样品与乙酸酐在4-二甲基氨基吡啶作为催化剂存在下反应,以将羟基进行乙酰化。在此,每羟基产生一分子乙酸,而过量乙酸酐的随后水解产生两分子乙酸。乙酸的消耗通过滴定分析由主要值和并行实施的空白值之间的差值确定。分子量通过凝胶渗透色谱法(GPC)测定。所述样品在作为洗脱剂的四氢呋喃中根据DIN 55672-1表征。
用作粘合剂的含羟基的(甲基)丙烯酸类共聚物可以是具有例如在WO 93/15849(第8页,第25行至第10页,第5行)中所述类型的单体组成的树脂。在此,通过按比例使用(甲基)丙烯酸作为单体而设定的(甲基)丙烯酸类共聚物的酸值应为0至30,优选0至15 mgKOH/g。所述(甲基)丙烯酸类共聚物的数均摩尔重量(由凝胶渗透色谱法以聚苯乙烯作为标准进行测定)优选为2000至20000 g/mol;玻璃化转变温度优选为–40℃至+60℃。通过按比例使用(甲基)丙烯酸羟基烷基酯而设定的根据本发明使用的(甲基)丙烯酸类共聚物的羟基含量优选为20至500 mg KOH/g,更优选50至250 mg KOH/g。
根据本发明适合作为粘合剂的聚酯多元醇是如描述在WO 93/15849中的具有二元和多元羧酸与二元和多元醇的单体组成的树脂。也可用作聚酯多元醇的是己内酯在低分子量二元和三元醇上的加聚产物,如例如以名称CAPA®(Perstorp)可得。计算确定的数均摩尔重量优选为500至5000 g/mol,更优选800至3000 g/mol;平均官能度优选为2.0至4.0,更优选为2.0至3.5。
原则上也可以使用根据本发明用作粘合剂的含氨基甲酸酯和酯基团的多元醇,如描述在EP 140 186中的那些。优选使用含氨基甲酸酯和酯基团的多元醇,对于其制造,使用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)。数均摩尔重量优选为500-5000 g/mol;平均官能度特别是2.0-3.5。
三烷氧基硅烷官能的粘合剂也适合用作组分B)。此类树脂可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(例如来自Evonik Industries AG的Dynasylan® MEMO)的共聚获得,如例如描述在WO 92/11328中。替代的合成路线在于含羟基的聚醚、聚酯、聚碳酸酯二醇或聚丙烯酸酯使用异氰酸根合丙基三烷氧基硅烷的衍生化,如例如描述在WO2008/131715的实施例3和4中。也可以考虑含氨基的粘合剂,例如氨基丙基三甲氧基硅烷(例如来自Evonik Industries AG的DynasylanAMMO)、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,也可以使用前述粘合剂的混合物。优选的粘合剂是单独或混合物形式的含羟基的聚酯和聚丙烯酸酯。
本发明的涂料中的B)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C)和D)的总和计。
在一个优选的实施方案中,催化剂D)以0.1直至5重量%,优选0.2至3重量%的量包含在本发明的涂料中,基于组分A)、B)、任选C)和D)的总和计。
用作催化剂D)的可以是有机羧酸。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。
所用的催化剂D)还是单独或混合物形式的具有卤离子、氢氧根、醇盐根或有机或无机酸阴离子作为反荷离子的季铵盐,优选四烷基铵盐和/或季鏻盐。它们的实例是:
四甲基铵甲酸盐、四甲基铵乙酸盐、四甲基铵丙酸盐、四甲基铵丁酸盐、四甲基铵苯甲酸盐、四乙基铵甲酸盐、四乙基铵乙酸盐、四乙基铵丙酸盐、四乙基铵丁酸盐、四乙基铵苯甲酸盐、四丙基铵甲酸盐、四丙基铵乙酸盐、四丙基铵丙酸盐、四丙基铵丁酸盐、四丙基铵苯甲酸盐、四丁基铵甲酸盐、四丁基铵乙酸盐、四丁基铵丙酸盐、四丁基铵丁酸盐和四丁基铵苯甲酸盐和四丁基鏻乙酸盐、四丁基鏻甲酸盐和乙基三苯基鏻乙酸盐、四丁基鏻苯并三唑盐、四苯基鏻苯酚盐和三己基十四烷基鏻癸酸盐、甲基三丁基铵氢氧化盐、甲基三乙基铵氢氧化盐、四甲基铵氢氧化盐、四乙基铵氢氧化盐、四丙基铵氢氧化盐、四丁基铵氢氧化盐、四戊基铵氢氧化盐、四己基铵氢氧化盐、四辛基铵氢氧化盐、四癸基铵氢氧化盐、十四烷基三己基铵氢氧化盐、四-十八烷基铵氢氧化盐、苄基三甲基铵氢氧化盐、苄基三乙基铵氢氧化盐、三甲基苯基铵氢氧化盐、三乙基甲基铵氢氧化盐、三甲基乙烯基铵氢氧化盐、甲基三丁基铵甲醇盐、甲基三乙基铵甲醇盐、四甲基铵甲醇盐、四乙基铵甲醇盐、四丙基铵甲醇盐、四丁基铵甲醇盐、四戊基铵甲醇盐、四己基铵甲醇盐、四辛基铵甲醇盐、四癸基铵甲醇盐、十四烷基三己基铵甲醇盐、四-十八烷基铵甲醇盐、苄基三甲基铵甲醇盐、苄基三乙基铵甲醇盐、三甲基苯基铵甲醇盐、三乙基甲基铵甲醇盐、三甲基乙烯基铵甲醇盐、甲基三丁基铵乙醇盐、甲基三乙基铵乙醇盐、四甲基铵乙醇盐、四乙基铵乙醇盐、四丙基铵乙醇盐、四丁基铵乙醇盐、四戊基铵乙醇盐、四己基铵乙醇盐、四辛基铵甲醇盐、四癸基铵乙醇盐、十四烷基三己基铵乙醇盐、四-十八烷基铵乙醇盐、苄基三甲基铵乙醇盐、苄基三乙基铵乙醇盐、三甲基苯基铵乙醇盐、三乙基甲基铵乙醇盐、三甲基乙烯基铵乙醇盐、甲基三丁基铵苄醇盐(benzylat)、甲基三乙基铵苄醇盐、四甲基铵苄醇盐、四乙基铵苄醇盐、四丙基铵苄醇盐、四丁基铵苄醇盐、四戊基铵苄醇盐、四己基铵苄醇盐、四辛基铵苄醇盐、四癸基铵苄醇盐、十四烷基三己基铵苄醇盐、四-十八烷基铵苄醇盐、苄基三甲基铵苄醇盐、苄基三乙基铵苄醇盐、三甲基苯基铵苄醇盐、三乙基甲基铵苄醇盐、三甲基乙烯基铵苄醇盐、四甲基铵氟化盐、四乙基铵氟化盐、四丁基铵氟化盐、四辛基铵氟化盐、苄基三甲基铵氟化盐、四丁基鏻氢氧化盐、四丁基鏻氟化盐、四丁基铵氯化盐、四丁基铵溴化盐、四丁基铵碘化盐、四乙基铵氯化盐、四乙基铵溴化盐、四乙基铵碘化盐、四甲基铵氯化盐、四甲基铵溴化盐、四甲基铵碘化盐、苄基三甲基铵氯化盐、苄基三乙基铵氯化盐、苄基三丙基铵氯化盐、苄基三丁基铵氯化盐、甲基三丁基铵氯化盐、甲基三丙基铵氯化盐、甲基三乙基铵氯化盐、甲基三苯基铵氯化盐、苯基三甲基铵氯化盐、苄基三甲基铵溴化盐、苄基三乙基铵溴化盐、苄基三丙基铵溴化盐、苄基三丁基铵溴化盐、甲基三丁基铵溴化盐、甲基三丙基铵溴化盐、甲基三乙基铵溴化盐、甲基三苯基铵溴化盐、苯基三甲基铵溴化盐、苄基三甲基铵碘化盐、苄基三乙基铵碘化盐、苄基三丙基铵碘化盐、苄基三丁基铵碘化盐、甲基三丁基铵碘化盐、甲基三丙基铵碘化盐、甲基三乙基铵碘化盐、甲基三苯基铵碘化盐和苯基三甲基铵碘化盐、甲基三丁基铵氢氧化盐、甲基三乙基铵氢氧化盐、四甲基铵氢氧化盐、四乙基铵氢氧化盐、四丙基铵氢氧化盐、四丁基铵氢氧化盐、四戊基铵氢氧化盐、四己基铵氢氧化盐、四辛基铵氢氧化盐、四癸基铵氢氧化盐、十四烷基三己基铵氢氧化盐、四-十八烷基铵氢氧化盐、苄基三甲基铵氢氧化盐、苄基三乙基铵氢氧化盐、三甲基苯基铵氢氧化盐、三乙基甲基铵氢氧化盐、三甲基乙烯基铵氢氧化盐、四甲基铵氟化盐、四乙基铵氟化盐、四丁基铵氟化盐、四辛基铵氟化盐和苄基三甲基铵氟化盐。这些催化剂可以单独或以混合物形式添加。优选使用四乙基铵苯甲酸盐和四丁基铵氢氧化盐。
作为催化剂D),还可以使用具有螯合配体的金属络合物。该螯合配体是具有至少两个能够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络合物作为催化剂,例如如描述在US-P 4,772,672 A中。优选的螯合物是单独或混合物形式的基于锌、锂、锡、铝、锆、钛和/或硼的螯合物,例如乙酰乙酸乙酯铝、乙酰乙酸乙酯锆、乙酰丙酮锌、乙酰丙酮锂和乙酰丙酮锡。优选使用乙酰丙酮锌。
可考虑的催化剂D)还是季铵乙酰丙酮化物或季鏻乙酰丙酮化物。此类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、苄基三甲基铵乙酰丙酮化物、苄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、苄基三甲基鏻乙酰丙酮化物、苄基三乙基鏻乙酰丙酮化物。特别优选地使用四乙基铵乙酰丙酮化物和四丁基铵乙酰丙酮化物。当然也可以使用此类催化剂的混合物。
此外适合作为催化剂D)的是铝、锆、钛和/或硼的醇盐和/或其酯。
还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),也可以使用在PUR技术领域中被证明有利的催化剂对氨基甲酸酯反应进行催化,例如有机Sn(IV)、Sn(II)、Zn和Bi化合物,或有机金属催化剂,例如二月桂酸二丁基锡、辛酸锡、新癸酸铋、或叔铵,例如1,4-二氮杂双环[2.2.2]辛烷。根据本发明,使用用于氨基甲酸酯反应的这种催化剂,但是仅以与其它本发明催化剂的共混物的形式。
作为催化剂D),也可以使用含磷,优选含磷和氮的催化剂。在此也可以使用两种或更多种不同催化剂的混合物。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,其优选选自非环状膦酸二酯、环状膦酸二酯、非环状二膦酸二酯和环状二膦酸二酯。这种催化剂例如描述在DE-A 102005045228中。
作为催化剂D),也可以使用胺封端的磷酸酯,特别优选胺封端的磷酸乙基己酯和胺封端的磷酸苯酯。用于将磷酸酯封端的胺的实例特别是叔铵,例如三乙胺。特别优选用于将磷酸酯封端的是在100至160℃的固化温度下具有高催化剂效率的叔胺。某些用胺封端的磷酸催化剂还是商购可得的(例如来自King Industries的Nacure类型)。特别合适的基于胺封端的磷酸偏酯的催化剂的实例是以Nacure 4167的名称来自King Industries的。
还可以用作催化剂D)的是未封端或封端形式的有机磺酸。原则上合适的磺酸是各种有机磺酸,优选对甲苯磺酸和十二烷基苯磺酸。对于热,即在高于100℃下交联的涂料体系,这些磺酸根据本发明也可以优选以胺中和的形式使用。还可根据本发明使用在高于100℃下才释放磺酸的潜在非离子化磺酸衍生物,例如磺酸与含环氧化物的组分的加合物,如描述在DE A 23 56768中。
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。
本发明的涂料中的催化剂D)可以仅由上述替代品构成,但是也可以使用这些催化剂的任意混合物。
本发明的涂料可以此外以常见浓度包含漆料技术中已知的辅助剂和/或添加剂E),例如稳定剂、光稳定剂、催化剂、附加的交联剂、填料、颜料、流平剂或流变助剂,例如所谓的“垂度控制剂(sag control agent)” ,微凝胶或热解二氧化硅或纳米颗粒,如例如描述在EP 1204701 B1中。额外地可以使用组分E),如漆料化学中已知的附加的交联剂,其例如以三聚氰胺树脂、苯并胍胺树脂、氨基甲酸酯官能的组分或封端的多异氰酸酯的形式。如必要,漆料技术中常见的无机或有机着色和/或效果颜料也可以并入本发明的涂料的组分E)中。
在一个优选实施方案中,本发明的涂料是无颜料的体系,即清漆体系。在这种情况中,组分E)可以优选以0.5直至8重量%,更优选1至6重量%的量包含在本发明的涂料中,基于组分A)、B)和C)的总和计。 例如,组分E)以6%的量存在,基于组分A)、B)和C)的总和计,如果该涂料,即组分A)、B)、C)、D)、E)和F)的总和具有110 g的总重量,其中组分A)、B)和C)的总和为100 g,E)的量为6 g,D)和F)的量分别为2 g。
在另一个优选的实施方案中,本发明的涂料是有色的涂料体系。作为组分E)的颜料和填料在这一情况中可以以10至200重量%的量包含在本发明的涂料中,基于A)、B)和C)的总和计。例如,组分E)以200重量%的量存在,基于组分A)、B)和C)的总和计,如果该涂料,即组分A)、B)、C)、D)、E)和F)的总和具有110 g的总重量,其中组分A)、B)和C)的总和为30g,E)的量为60 g,D)和F)的量分别为10 g。
本发明的涂料还可以包含有机溶剂作为组分F)。合适的溶剂是例如酮、醇、酯或芳族化合物。
组分F)优选以20直至150重量%,更优选30至60重量%的量包含在本发明的涂料中,基于组分A)、B)和C)的总和计。
选择组分A)、B)、C)、D)、E)和F) 的各自含量的总和,以使得重量含量合计为100重量%。
另一优选实施方案是如下的本发明的涂料:
涂料,其包含
A) 10-99重量%的至少一种具有式1的含脲基甲酸酯的化合物:
其中R、R1-R6彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m和n彼此独立地是0-2,
B) 1-90重量%的至少一种粘合剂,优选含羟基或含胺的粘合剂,
C) 0-50重量%的至少一种脂族或脂环族的多异氰酸酯,其具有至少2,优选2.8至6的NCO官能度,
D) 0-5重量%的至少一种催化剂,
E) 0-50重量%的辅助剂和/或添加剂,
其中这些组分合计为100重量%,
F) 任选的溶剂。
本发明的涂料通过将上述组分混合来制造。该混合可以通过本领域技术人员已知的混合机,例如不连续地在搅拌的容器、溶解器、珠磨机、辊式破碎机等中,或连续地使用例如静态混合机来进行。
本发明进一步通过下列非限制性实施例来说明,从中可获知本发明的其它特征、实施方案、方面和优点。
本发明的主题还是本发明的涂料在用于金属、塑料、玻璃、木材、MDF(中密度纤维板)或皮革基材或其它耐热基底的漆料组合物中的用途。
本发明的主题还是本发明的涂料在用于胶粘金属、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。
本发明的主题同样是特别用于汽车车身、摩托车和自行车、建筑物部件和家用设备的金属涂料组合物以及木材涂料组合物、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。
本发明进一步通过下列非限制性实施例来说明,从中可获知本发明的其它特征、实施方案、方面和优点。
实施例
1) 制造单脲基甲酸酯
a)
将236 g(1 mol)三甲氧基甲硅烷基丙基氨基甲酸甲酯(Evonik Industries AG)和205g异氰酸根合丙基三甲氧基硅烷(Evonik Industries AG)相互混合并加热到175℃ 2 h。然后,在100℃和 0.3 mbar下经短程蒸馏分离出输出产物(Ausgangsprodukt)。留下183 g(41.5%)的纯净无色透明(wasserklar)液体。
在CDCl3中的C13-NMR (ppm): 156.9 (1); 154.4 (1); 53.5 (1); 50.5 (10);46.3 (1); 43.2 (1); 23.2 (1); 22.6 (1); 6.7 (1); 6.5 (1).
粘度为大约200 mPas,因此是非常低粘性的。
b)
将236 g(1 mol)三甲氧基甲硅烷基丙基氨基甲酸甲酯(Evonik Industries AG)、205g异氰酸根合丙基三甲氧基硅烷(Evonik Industries AG)和0.4 g氯化锡(II)相互混合并加热到150℃ 1 h。然后,在90℃和0.3 mbar下经短程蒸馏分离出输出产物。留下339 g(76.9%)的纯净无色透明液体(NMR见上)。
c)
将236 g(1 mol)三甲氧基甲硅烷基丙基氨基甲酸甲酯(Evonik Industries AG)、205g异氰酸根合丙基三甲氧基硅烷(Evonik Industries AG)和1 g乙酰丙酮铁(III)相互混合并加热到90℃ 3 h。然后,在90℃和0.3 mbar下经短程蒸馏分离出输出产物。留下184 g(41.5%)的纯净无色透明液体(NMR见上)。
2) 本发明的涂料
配制:
将44.5 g Setalux 1760(OH官能的丙烯酸酯,Nuplex industries)和30 g本发明产物a)与25 g乙酸丁酯/二甲苯(1:1)混合并加入0.5 g催化剂(VESTANAT EP-CAT 11,EvonikIndustries AG)。将该混合物通过120 µm螺旋刮刀刮涂到钢板上并在140℃下烧制22 min。涂层(30 µm层厚度)具有176 s摆撞硬度和> 150 MEK双冲程的耐化学品性。因此,其完全固化。
耐刮性:
起始光泽度为86刻度分度(Skt.)(20°)。在刷擦测试(Bürstentest)后,光泽度降至84Skt.。摩擦掉色(Crockmeter)测试导致光泽度为83 Skt.。光泽度损失因此为2或3 Skt.,因此耐刮性是极好的!
评估:由于刮具的光泽度损失0-9 Skt.极好,10-20很好,21-34好,35-44中等,> 45差
相比而言,基于Setalux 1760的商购的双组份(2K)PUR漆料的光泽度损失为大约30Skt.。
刷擦测试(湿):
仪器: U 1 系列号003,制造商:BASF L + F,建造时间:1993
漆层表面由于承受质量(2 kg)的丝网(Siebgewebe)(尼龙丝网号11,网孔大小25 µm)而受损。该丝网和漆层表面使用洗涤剂溶液(在水中的0.25% Persil溶液)充分润湿。试验板借助发动机驱动以往复运动的形式在该丝网下面来回移动。在测试前和后测量光泽度。
摩擦掉色测试(干)
仪器: U 1 系列号003,制造商:BASF L + F,建造时间:1993
漆层表面由于承受质量(920 g)的织物(3M 281Q WetO干燥抛光纸)而受损。试验板借助发动机驱动以往复运动的形式在该织物下面来回移动。
Claims (17)
1.涂料,其包含
A) 至少一种具有式1的含脲基甲酸酯的化合物:
其中R、R1-R6彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m和n彼此独立地是0-2,
B) 至少一种粘合剂,
C) 任选的至少一种脂族或脂环族的多异氰酸酯,其具有至少2的NCO官能度,
D) 任选的至少一种催化剂,
E) 任选的辅助剂和/或添加剂,
F) 任选的溶剂。
2.根据权利要求1的涂料,其包含
A) 10-99重量%的至少一种具有式1的含脲基甲酸酯的化合物:
其中R、R1-R6彼此独立地是相同或不同的具有1-8个碳原子的烃基,其中它们可以是支化或环状的或可以相互合并成环状,并且m和n彼此独立地是0-2,
B) 1-90重量%的至少一种粘合剂,
C) 0-50重量%的至少一种脂族或脂环族的多异氰酸酯,其具有至少2,优选2.8至6的NCO官能度,
D) 0-5重量%的至少一种催化剂,
E) 0-50重量%的辅助剂和/或添加剂,
其中组分A)-E)合计为100重量%,
F) 任选的溶剂。
3.根据前述权利要求至少一项的涂料,其中m和n是 0、R1和R5是甲基或乙基,且R2和R4是甲基或丙基。
4.根据前述权利要求至少一项的涂料,其中m和n是 0、R1 = R5 =甲基且R2 = R4 =丙基。
5.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂B)是含羟基和/或含胺基团的粘合剂。
6.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂B)是单独或混合物形式的具有20至500 mg KOH/g的OH值和250至6000 g/mol的平均摩尔质量的含羟基的聚酯、聚醚、聚丙烯酸酯、聚碳酸酯和聚氨酯。
7.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂B)是单独或混合物形式的具有50至250 mg KOH/g的OH值和500至6000 g/mol的平均分子量的含羟基的聚酯或聚丙烯酸酯作为粘合剂组分。
8.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂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。
9.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂B)是单独或混合物形式的含羟基的聚醚、聚酯、聚碳酸酯二醇或聚丙烯酸酯通过异氰酸根合丙基三烷氧基硅烷的至少一种衍生物。
10.根据前述权利要求至少一项的涂料,其特征在于包含的粘合剂B)是单独或混合物形式的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。
11.根据前述权利要求至少一项的涂料,其特征在于包含的组分C)是单独或混合物形式的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)。
12.根据前述权利要求至少一项的涂料,其特征在于包含的组分C)是单独或混合物形式的IPD、HDI、TMDI和/或H12MDI。
13.根据前述权利要求至少一项的涂料,其特征在于包含的组分C)是异氰脲酸酯,特别是来自IPDI和/或HDI的异氰脲酸酯。
14.根据前述权利要求至少一项的涂料,其特征在于包含的组分D)是单独或混合物形式的金属羧酸盐、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。
15.根据前述权利要求至少一项的涂料,其特征在于包含的添加剂E)是单独或混合物形式的稳定剂、光稳定剂、催化剂、附加的交联剂、填料、颜料、流平剂或流变助剂。
16.根据前述权利要求至少一项的涂料用于漆料组合物和胶粘剂组合物和金属涂料组合物中的用途。
17.通过将组分A)-F)混合制造根据前述权利要求1-14至少一项的涂料的方法。
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EP15192087.3A EP3162827B1 (de) | 2015-10-29 | 2015-10-29 | Beschichtungsmittel mit monoallophanaten auf basis von alkoxysilanalkylisocyanaten |
EP15192087.3 | 2015-10-29 | ||
PCT/EP2016/073976 WO2017071933A1 (de) | 2015-10-29 | 2016-10-07 | Beschichtungsmittel mit monoallophanaten auf basis von alkoxysilanalkylisocyanaten |
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US (1) | US10538684B2 (zh) |
EP (1) | EP3162827B1 (zh) |
JP (1) | JP2018537555A (zh) |
CN (1) | CN108137777A (zh) |
ES (1) | ES2681484T3 (zh) |
WO (1) | WO2017071933A1 (zh) |
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EP3263618A1 (de) | 2016-06-27 | 2018-01-03 | Evonik Degussa GmbH | Alkoxysilan-funktionalisierte allophanate |
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 |
EP3404073B1 (de) * | 2017-05-19 | 2021-09-22 | Evonik Operations GmbH | Hydrophile, alkoxysilanhaltige isocyanurate |
PL3546465T3 (pl) | 2018-03-28 | 2021-03-22 | Evonik Operations Gmbh | Sposób wytwarzania izocyjanianów zawierających grupy alkoksysilanowe |
ES2820280T3 (es) | 2018-03-28 | 2021-04-20 | Evonik Operations Gmbh | Procedimiento para la producción de isocianatos que contienen grupos alcoxisilano |
EP3546467B1 (de) | 2018-03-28 | 2020-08-12 | Evonik Operations GmbH | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate |
EP3546466B1 (de) | 2018-03-28 | 2020-12-02 | Evonik Operations GmbH | Verfahren zur herstellung alkoxysilangruppen-haltiger isocyanate |
WO2023237605A1 (en) * | 2022-06-09 | 2023-12-14 | Basf Coatings Gmbh | Low temperature curable multilayer coating systems with excellent appearance |
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- 2016-10-07 CN CN201680062770.6A patent/CN108137777A/zh active Pending
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US20180312713A1 (en) | 2018-11-01 |
WO2017071933A1 (de) | 2017-05-04 |
EP3162827A1 (de) | 2017-05-03 |
US10538684B2 (en) | 2020-01-21 |
JP2018537555A (ja) | 2018-12-20 |
ES2681484T3 (es) | 2018-09-13 |
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