CN104736605B - 具有改进的光泽度的水可乳化型异氰酸酯 - Google Patents
具有改进的光泽度的水可乳化型异氰酸酯 Download PDFInfo
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- CN104736605B CN104736605B CN201380050835.1A CN201380050835A CN104736605B CN 104736605 B CN104736605 B CN 104736605B CN 201380050835 A CN201380050835 A CN 201380050835A CN 104736605 B CN104736605 B CN 104736605B
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- emulsifiable polyisocyanate
- water emulsifiable
- weight
- acid
- compound
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000012948 isocyanate Substances 0.000 title abstract description 20
- 150000002513 isocyanates Chemical class 0.000 title abstract description 17
- 239000005056 polyisocyanate Substances 0.000 claims description 94
- 229920001228 polyisocyanate Polymers 0.000 claims description 94
- -1 isocyanuric acid ester Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 125000001931 aliphatic group Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 27
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- 239000011248 coating agent Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 11
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- 150000002596 lactones Chemical class 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 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 description 3
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- 238000006243 chemical reaction Methods 0.000 description 19
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 11
- 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 11
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 11
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- 125000002723 alicyclic group Chemical group 0.000 description 10
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- 235000011187 glycerol Nutrition 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
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- 229920000233 poly(alkylene oxides) Polymers 0.000 description 7
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- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical class OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 5
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical class OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
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- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 1
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- WZZPVFWYFOZMQS-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diol Chemical compound C1CC2(O)C(O)CC1C2 WZZPVFWYFOZMQS-UHFFFAOYSA-N 0.000 description 1
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- ZUPXSCMRFYXOOJ-UHFFFAOYSA-N isoricinoleic acid Natural products CCCCCC=CCCC(O[Si](C)(C)C)CCCCCCCC(=O)OC ZUPXSCMRFYXOOJ-UHFFFAOYSA-N 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical group COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
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- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical class CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
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- PLYIPBIZXSTXCW-UHFFFAOYSA-N octanoic acid;tin Chemical compound [Sn].CCCCCCCC(O)=O PLYIPBIZXSTXCW-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
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- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical group O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000007347 radical substitution reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007616 round robin method Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- UTGPYHWDXYRYGT-UHFFFAOYSA-N tetratriacontanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTGPYHWDXYRYGT-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- SUJUOAZFECLBOA-UHFFFAOYSA-N tritriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC SUJUOAZFECLBOA-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- LFOXXKXKYHIANI-UHFFFAOYSA-L zinc;7,7-dimethyloctanoate Chemical class [Zn+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O LFOXXKXKYHIANI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
-
- 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
- C09D175/08—Polyurethanes from polyethers
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
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Abstract
本发明涉及一种用于制备水可乳化型异氰酸酯的方法和所述水可乳化型异氰酸酯的用途。
Description
本发明涉及一种用于制备水可乳化性异氰酸酯的方法及其用途。
水可乳化型多异氰酸酯作为交联剂被加入至水性聚合物分散体中,并被广泛记载于文献中。在水中的乳化性可通过将多异氰酸酯与由多异氰酸酯与亲水性分子反应而获得的乳化剂混合而产生。
常用的亲水性分子包括非离子亲水性分子,例如聚环氧烷醇。
EP-A2 206 059记载了水分散性多异氰酸酯制剂,其包含脂族多异氰酸酯和脂族多异氰酸酯与具有至少一种包含至少10个环氧乙烷单元的聚醚链的一元或多元、非离子聚亚烷基醚醇乳化剂的反应产物。作为合适的多异氰酸酯,大量的实例为脂族和脂环族二异氰酸酯,更优选为基于1,6-二异氰酸根合己烷(HDI)的异氰脲酸酯和缩二脲和/或基于1-异氰酸根合-3,5,5-三甲基-5-异氰酸根合甲基环己烷(IPDI)的异氰脲酸酯。
EP-A1 540 985同样记载了多异氰酸酯混合物,但在这种情况下聚醚链具有的平均环氧乙烷单元的含量为5.0至9.9。
EP-A2 486 881记载了非水性脂族多异氰酸酯制剂,其包含来自脂族多异氰酸酯系列的多异氰酸酯,并包含足以确保脂族多异氰酸酯的分散性的量的芳族或脂族二异氰酸酯与一元或(较不优选的)在聚醚链中具有至少8个环氧乙烷单元的多元聚亚烷基醚醇的反应产物。实例仅使用单官能聚乙二醇。二异氰酸酯和醇的反应以OH基团相对于二异氰酸酯的NCO基团的比例为60至120摩尔%进行。然后,由此获得的产物作为乳化剂与多异氰酸酯混合。
EP 959087 A1记载了水可乳化的、聚醚改性的多异氰酸酯混合物,其中高比例的聚醚通过脲基甲酸酯基团键合至多异氰酸酯。
其缺点是在形成脲基甲酸酯基团的反应中每个羟基消耗两当量的异氰酸酯基团,因此,急剧地降低了基于反应物测得的产物的NCO含量。
DE-A1 199 58 170记载了聚醚改性的、水分散性的多异氰酸酯混合物,其已用一元聚环氧烷聚醚醇改性。非常特别优选具有基于HDI、IPDI和/或4,4’-二异氰酸根合二环己基甲烷的异氰脲酸酯结构的多异氰酸酯或多异氰酸酯混合物。
DE-A1 198 22 890记载了水性双组分聚氨酯涂料体系,其硬化剂组分由聚环氧烷聚醚醇和以脂族和/或脂环族方式连接的异氰酸酯基团、优选基于HDI、IPDI和/或4,4’-二异氰酸根合二环己基甲烷的异氰脲酸酯结构在脲基甲酸酯化(allophanatization)条件下制备。通过脲基甲酸酯基团主要连接的聚醚链也已知于DE-A1 198 47 077。
记载的非离子乳化剂包括聚乙烯吡咯烷酮改性的多异氰酸酯(EP-A2 754 713)。
还用作活性分散单元(actively dispersing unit)的为包含羧酸基团的聚环氧烷醚(正如DE-A1 100 07 820和DE-A1 41 13 160中所描述)或聚醚酯醇(EP-A1 728 785)。
DE-A1 40 01 783记载了多异氰酸酯混合物,其含有用于分散性的化学键合的羧基,且具有1重量%至23重量%的缩脲二酮含量。
此外,含有羧基的化合物被描述为乳化剂(EP-A2 548 669)、叔胺和/或铵基(EP-A1 582 166和EP A1 531 820)、磷酸(DE-A1 197 24 199)或磺酸(EP-A1 703 255)的酸酯。
所述多异氰酸酯混合物的缺点是它们不能满足由它们获得的涂层在光泽度上的要求。
水可乳化型异氰酸酯可溶于有机溶剂,例如用于提高分散性目的的碳酸酯或内酯,如EP-A 697 424中所描述。
WO 2004/22624记载了基于1,6-六亚甲基二异氰酸酯的多异氰酸酯和基于异佛尔酮二异氰酸酯的多异氰酸酯的水可乳化型混合物,其不仅表现出高硬度,而且表现出良好的水可乳化性。
然而,用这些涂层材料获得的涂层的干燥性能是不足的。
WO 2012/007431记载了高官能度的多异氰酸酯,其含有氨基甲酸酯基团,并可通过将至少一种多官能醇和至少一种多异氰酸酯以NCO基团与OH基团的摩尔比为至少3:1的比例反应获得。
缺点是这些具有氨基甲酸酯基团的高官能度多异氰酸酯不是水可乳化型的。
WO 2011/124710 A1记载了包含含有羟基的脂肪酸甘油酯、多异氰酸酯和粘合剂的涂料组合物。
所得涂层在加热时表现出自修复效果。
缺点是构成三组分体系的涂料组合物不是水可乳化型的。
使用者需要水可乳化型异氰酸酯具有以下性能:
1.所述异氰酸酯应当易于乳化;不赞成必须使用要求高的装置如高剪切搅拌器;
2.乳剂应该是精细的,否则,例如光泽度可能被破坏,或者可能出现浑浊。
3.在涂层的情况下,需要高光泽度。
4.水可乳化型异氰酸酯不具有太高的粘度。
本发明的目的是提供一种用于制备具有良好的乳化性能、在23℃下具有不高于12Pas的粘度并且可制备具有高光泽度的涂层的水可乳化型多异氰酸酯的方法。
所述目的通过水可乳化型多异氰酸酯实现,其包含:
(A)至少一种基于至少一种(环)脂族二异氰酸酯的多异氰酸酯,
(B)至少一种多元醇,其具有:
-至少为2且最多达为4的羟基官能度,以及
-至少为92至1500g/mol的数均摩尔质量,
(C)至少一种含有环氧乙烷基团的一元醇,其具有至少7个环氧乙烷基团,以及
(D)任选的溶剂,其中
-(A)中的NCO基团与(B)和(C)中的羟基基团的比为至少为5:1至100:1,
-以44g/mol计的环氧乙烷基团的量为至少12重量%,优选至少14重量%,更优选至少15重量%,基于(A)、(B)和(C)的总量计,
-组分(B)的量为0.5至4.0重量%,
-组分(C)的量为至少5重量%,且最多达25重量%,以及
-根据DIN EN ISO 3219/A.3,在23℃下,在具有1000s-1的剪切速率的锥/板体系中的粘度为2500mPas至12 000mPas。
所述混合物显示出易于乳化,得到稳定和精细的乳剂,且用它们获得的涂层显示出高光泽度。
多异氰酸酯(A)为脂族或脂环族二异氰酸酯的低聚物,在本说明书中简称为(环)脂族。
所述化合物的NCO官能度通常至少为1.8且可最多达为8,优选1.8至5,且更优选2至4。
合适的多异氰酸酯为具有异氰脲酸酯基团的多异氰酸酯、具有缩脲二酮基团的多异氰酸酯、具有缩二脲基团的多异氰酸酯、具有氨基甲酸酯基团或脲基甲酸酯基团的多异氰酸酯、包含二嗪三酮基团或亚氨基
二嗪二酮基团的多异氰酸酯、直链或支链的C4-C20亚烷基二异氰酸酯和具有共计6至20个碳原子的脂环族二异氰酸酯的脲酮亚胺改性的多异氰酸酯,或它们的混合物。
二异氰酸酯优选为具有4至20个碳原子的异氰酸酯。典型的二异氰酸酯的实例为脂族二异氰酸酯,例如四亚甲基二异氰酸酯、六亚甲基二异氰酸酯(1,6-二异氰酸根合己烷)、八亚甲基二异氰酸酯、十亚甲基二异氰酸酯、十二亚甲基二异氰酸酯、十四亚甲基二异氰酸酯、赖氨酸二异氰酸酯的衍生物、三甲基己烷二异氰酸酯或四甲基己烷二异氰酸酯;脂环族二异氰酸酯,例如1,4-二异氰酸根合环己烷、1,3-二异氰酸根合环己烷或1,2-二异氰酸根合环己烷、4,4’-二(异氰酸根合环己基)甲烷或2,4’-二(异氰酸根合环己基)甲烷、1-异氰酸根合-3,3,5-三甲基-5-(异氰酸根合甲基)环己烷(异佛尔酮二异氰酸酯)、1,3-双(异氰酸根合甲基)环己烷或1,4-双(异氰酸根合甲基)环己烷或2,4-二异氰酸根合-1-甲基环己烷或2,6-二异氰酸根合-1-甲基环己烷,以及3(或4),8(或9)-双(异氰酸根合甲基)三环[5.2.1.02,6]癸烷异构体混合物。
也可存在所述二异氰酸酯的混合物。
可用的二异氰酸酯优选具有10重量%至60重量%,优选15至60重量%,且更优选20重量%至55重量%的异氰酸酯基团含量(以NCO计,分子量=42),基于二异氰酸酯(混合物)计。
优选为脂族和/或脂环族的——在本说明书中统称为(环)脂族——二异氰酸酯和多异氰酸酯,实例为上述脂族和/或脂环族二异氰酸酯,或它们的混合物。
特别优选为六亚甲基二异氰酸酯、1,3-双(异氰酸根合甲基)环己烷、异佛尔酮二异氰酸酯和4,4’-二(异氰酸根合环己基)甲烷或2,4’-二(异氰酸根合环己基)甲烷,非常特别优选为异佛尔酮二异氰酸酯和六亚甲基二异氰酸酯,尤其优选为六亚甲基二异氰酸酯。
异佛尔酮二异氰酸酯通常为混合物形式,特别地为以通常约60:40至80:20(w/w),优选约70:30至75:25,更优选约75:25的比例存在的顺式和反式异构体的混合物形式。
4,4’-二异氰酸酯二环己基甲烷也可为不同的顺式和反式异构体的混合物形式。
脂环族异氰酸酯为包含至少一个脂环族环体系的那些。
脂族异氰酸酯为仅包含直链或支链的那些,也就是说为无环化合物。
本发明不仅可以使用通过将相应胺光气化而获得的那些二异氰酸酯和多异氰酸酯,而且可以使用在不使用光气的情况下,即通过无光气方法制备的那些。根据EP-A-0 126299(US 4 596 678)、EP-A-126 300(US 4 596 679)和EP-A-355 443(US 5 087 739),例如,(环)脂族二异氰酸酯,例如六亚甲基1,6-二异氰酸酯(HDI)、在亚烷基中具有6个碳原子的同分异构的脂族二异氰酸酯、4,4’-二(异氰酸根合环己基)甲烷或2,4’-二(异氰酸根合环己基)甲烷,以及1-异氰酸根合-3-异氰酸根合甲基-3,5,5-三甲基环己烷(异佛尔酮二异氰酸酯或IPDI),例如可通过如下方法制备:将(环)脂族二胺与例如脲和醇反应得到(环)脂族二氨基甲酸酯,并将所述酯热裂解成相应的二异氰酸酯和醇。合成过程通常在循环方法中、并且任选地在N-未取代的氨基甲酸酯、碳酸二烷基酯和从反应过程中回收的其它副产物的存在下连续地进行。以此方式获得的二异氰酸酯或多异氰酸酯通常含有非常低比例或甚至不可测量的比例的含氯化合物,以使产品具有有利的色值(color number)。
在本发明的一个实施方案中,二异氰酸酯和多异氰酸酯(A)具有的可水解的氯的总含量小于200ppm,优选小于120ppm,更优选小于80ppm,非常优选小于50ppm,特别小于15ppm,尤其小于10ppm。这可以通过例如ASTM标准D4663-98测定。当然,也可以使用具有较高氯含量的二异氰酸酯和多异氰酸酯(A)。
还值得注意的是
1)含有异氰脲酸酯基团并且衍生自脂族和/或脂环族二异氰酸酯的多异氰酸酯。在本文中特别优选相应的脂族和/或脂环族异氰酸根合异氰脲酸酯,特别是基于六亚甲基二异氰酸酯和异佛尔酮二异氰酸酯的那些。所存在的异氰脲酸酯特别是构成二异氰酸酯的环状三聚体的三异氰酸根合烷基异氰脲酸酯和/或三异氰酸根合环烷基异氰脲酸酯,或是与它们的含有一个以上异氰脲酸酯环的高级同系物的混合物。所述异氰酸根合异氰脲酸酯通常具有10重量%至30重量%,特别为15重量%至25重量%的NCO含量和2.6至8的平均NCO官能度。
2)具有以脂族和/或脂环族方式连接的异氰酸酯基团的缩脲二酮二异氰酸酯,优选以脂族和/或脂环族方式连接的且特别衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯的那些。缩脲二酮二异氰酸酯是二异氰酸酯的环化二聚合产物。
缩脲二酮二异氰酸酯可作为单独组分使用或以与其他多异氰酸酯,特别是1)中指定的那些的混合物形式使用。
3)含有缩二脲基团并具有以脂环族或脂族方式连接的(优选以脂环族或脂族方式连接的)异氰酸酯基团的多异氰酸酯,尤其为三(6-异氰酸根合己基)缩二脲或它与其高级同系物的混合物。这些含有缩二脲基团的多异氰酸酯通常具有18%重量至22重量%的NCO含量和2.8至4.5的平均NCO官能度。
4)含有氨基甲酸酯和/或脲基甲酸酯基团并具有以脂族或脂环族方式连接的(优选以脂族或脂环族方式连接的)异氰酸酯基团的多异氰酸酯,其可通过例如将过量的六亚甲基二异氰酸酯或过量的异佛尔酮二异氰酸酯与一元醇或多元醇反应而获得,所述一元醇或多元醇为例如甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、正己醇、正庚醇、正辛醇、正癸醇、正十二醇(月桂醇)、2-乙基己醇、正戊醇、硬脂醇、十六醇、月桂醇、乙二醇单甲醚、乙二醇单***、1,3-丙二醇单甲醚、环戊醇、环己醇、环辛醇、环十二醇、三羟甲基丙烷、新戊二醇、季戊四醇、1,4-丁二醇、1,6-己二醇、1,3-丙二醇、2-乙基-1,3-丙二醇、2-甲基-1,3-丙二醇、乙二醇、二乙二醇、三乙二醇、四乙二醇、戊乙二醇、丙三醇、1,2-二羟基丙烷、2,2-二甲基-1,2-乙二醇、1,2-丁二醇、1,4-丁二醇、3-甲基-1,5-戊二醇、2-乙基-1,3-己二醇、2,4-二乙基-1,3-辛二醇、羟基特戊酸新戊二醇酯、双(三羟甲基丙烷)、二季戊四醇、2,2-双(4-羟基环己基)丙烷、1,1-环己烷二甲醇、1,2-环己烷二甲醇、1,3-环己烷二甲醇、1,4-环己烷二甲醇、1,2-环己二醇、1,3-环己二醇或1,4-环己二醇或它们的混合物。这些含有氨基甲酸酯和/或脲基甲酸酯基团的多异氰酸酯通常具有12重量%至20重量%的NCO含量和2.5至4.5的平均NCO官能团。
5)含有噁二嗪三酮基团的多异氰酸酯,优选衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯。这种含有二嗪三酮基团的多异氰酸酯可由二异氰酸酯和二氧化碳制备。
6)含有亚氨基噁二嗪二酮基团的多异氰酸酯,优选衍生自六亚甲基二异氰酸酯或异佛尔酮二异氰酸酯。这种含有亚氨基二嗪二酮基团的多异氰酸酯可以借助特定的催化剂由二异氰酸酯制备。
7)脲酮亚胺改性的多异氰酸酯。
8)碳二酰亚胺改性的多异氰酸酯。
9)超支化的多异氰酸酯,这种多异氰酸酯例如已知于DE-A1 10013186或DE-A110013187。
10)聚氨酯-多异氰酸酯预聚物,由二异氰酸酯和/或多异氰酸酯与醇制备。
11)聚脲-多异氰酸酯预聚物。
多异氰酸酯1)至11)可以混合物形式使用,包括任选地以与二异氰酸酯的混合物形式使用。
多异氰酸酯(A)也可以至少部分封闭的形式存在。
这种用于封闭异氰酸酯的基团记载于D.A.Wicks,Z.W.Wicks,Progress inOrganic Coatings,36,148-172(1999),41,1-83(2001)和43,131-140(2001)中。
当本发明的涂料组合物以单组分形式使用时是特别优选的。
优选的化合物(A)为六亚甲基1,6-二异氰酸酯(HDI)或1-异氰酸根合-3-异氰酸根合-甲基-3,5,5-三甲基环己烷(非常优选为六亚甲基1,6-二异氰酸酯)的氨基甲酸酯、缩二脲和异氰脲酸酯(更优选为异氰脲酸酯)。
作为其制备的必然结果,多异氰酸酯(A)仍可存在小比例的单体二异氰酸酯,例如,最多达5重量%,更优选最多达3重量%,非常优选最多达2重量%,更特别最多达1重量%,尤其最多达0.5重量%,以及甚至最多达0.25重量%。
多元醇(B)为至少一种多元醇,其具有
-至少2且最多达4的羟基官能度,以及
-至少92至1500g/mol的数均摩尔质量。
所述官能度应至少为2,优选至少为2且最多达4。特别优选官能度平均为2至3。
具有上述官能度的多元醇可优选为:
(B1)至少一种脂肪酸与至少一种多元醇的酯化产物,和/或
(B2)至少一种羟基烷烃羧酸或相应的内酯与至少一种多元醇的酯化产物,和/或
(B3)至少一种任选的烷氧基化的多元醇。
化合物(B1)为至少一种脂肪酸与至少一种多元醇的酯化产物。
使用至少一种脂肪酸,例如1至5种,优选1至3种,更优选1至2种,且非常优选精确为一种脂肪酸。
在本发明的一个优选实施方案中,天然脂肪酸特别地以它们的混合物形式使用。
所述脂肪酸具有至少12个碳原子,优选至少14个,且更优选至少16个。
通常所述脂肪酸具有最多达40个碳原子,优选最多达30个,且更优选最多达20个。
所述脂肪酸通常为烷烃羧酸、烯烃羧酸、二烯烃羧酸或多烯烃羧酸,其可含有一个或多个羟基,且其可为直链或支链,优选为直链;优选烷烃羧酸或烯烃羧酸,更优选烷烃羧酸,其可含有一个或多个羟基。
它们的实例为月桂酸、肉豆蔻酸、十五烷酸、棕榈酸、十七烷酸、硬脂酸、十九酸、花生酸、二十二烷酸、二十四烷酸、二十六烷酸、二十八烷酸、三十烷酸、三十二烷酸、三十三烷酸、三十四烷酸、三十五烷酸、油酸、亚油酸和亚麻酸。
在所述至少一种脂肪酸中,至少一种脂肪酸具有至少一个羟基,例如1至3个,优选1至2个,且更优选精确为一个羟基。
具有羟基的脂肪酸的一个优选实例为蓖麻油酸(12-羟基-(Z)-9-十八烯酸)和异蓖麻油酸(9-羟基-(Z)-12-十八烯酸),对本发明的目的而言,使用对映体形式、优选(R)-形式,或不论是以对映体纯的形式使用,作为对映体富集的混合物使用,或是作为对映体混合物使用是不重要的。另一优选的实例为12-羟基硬脂酸。
多元醇为至少一种、优选精确为一种具有至少双官能团的多元醇,其优选具有2至4个,更优选2至3个羟基。
它们的实例为三羟甲基丁烷、四羟甲基丙烷、三羟甲基乙烷、季戊四醇、丙三醇、双(三羟甲基丙烷)和双甘油。
在一个优选实施方案中,化合物(B1)为具有160至173mg KOH/g的OH值的蓖麻油。
用于本说明书目的的这种蓖麻油为至少部分和优选全部酯化了的酰基甘油,其中至少一个,优选至少两个酰基基团为蓖麻油酸或异蓖麻油酸,优选为蓖麻油酸。
例如,脂肪酸的混合物优选包括蓖麻油酸与不含羟基的脂肪酸的两种分子的混合物,所述脂肪酸优选选自油酸、亚油酸、棕榈酸和硬脂酸。
化合物(B2)为至少一种羟基烷烃羧酸或相应内酯与至少一种多元醇的酯化产物。
多元醇为至少一种(优选精确为一种)具有至少双官能团的多元醇,其优选具有2至4个,更优选2至3个羟基。
它们的实例为乙二醇、二乙二醇、三乙二醇、1,2-丙二醇、1,3-丙二醇、1,1-二甲基-1,2-乙二醇、2-丁基-2-乙基-1,3-丙二醇、2-乙基-1,3-丙二醇、2-甲基-1,3-丙二醇、新戊二醇、羟基特戊酸新戊二醇酯、1,2-丁二醇、1,3-丁二醇或1,4-丁二醇、1,6-己二醇、1,10-癸二醇、双(4-羟基环己烷)异亚丙烷、四甲基环丁二醇、1,2-环己二醇、1,3-环己二醇或1,4-环己二醇、环辛二醇、降莰烷二醇(norbornanediol)、蒎烷二醇、十氢萘二醇、2-乙基-1,3-己二醇、2,4-二乙基-1,3-辛二醇、2,2-双(4-羟基环己基)丙烷、1,1-环己烷二甲醇、1,2-环己烷二甲醇、1,3-环己烷二甲醇和1,4-环己烷二甲醇、1,2-环己二醇、1,3-环己二醇或1,4-环己二醇、三羟甲基丁烷、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、丙三醇、双(三羟甲基丙烷)和双甘油。
优选内酯系聚酯醇,其为内酯的均聚物或共聚物,优选内酯与具有相应官能度的合适的起始分子的具有末端羟基的加合物。
合适的内酯优选为衍生自通式HO-(CH2)z-COOH的那些,其中z为1至20的数,且其中亚甲基单元的一个H原子也可被C1至C4烷基取代。实例为ε-己内酯、β-丙内酯、γ-丁内酯和/或甲基-ε-己内酯、4-羟基苯甲酸、6-羟基-2-萘甲酸或新戊内酯以及它们的混合物。合适的起始组分的实例为上述多元醇。ε-己内酯的相应的多元醇是特别优选的。
特别优选作为化合物(B2)的是以下化合物:
其中
R4为氢或C1至C4烷基,
k、l、m和q彼此独立地各自为1至5,优选1至4,特别是2至3的正整数。
对于每个i,Yi彼此独立地各自为基团–[-O-(CH2)z-(C=O)-]-,以及
z为2至6,优选2至5,更优选3至5的正整数。
组分(B3)包括至少一种,优选一至四种,更优选一至三种,非常优选一或两种,且更特别精确为一种任选烷氧基化的多元醇。
所述多元醇为至少一种、优选精确为一种具有至少双官能团的多元醇,其优选具有2至4,更优选具有3至4,且非常优选具有3个羟基。
优选的化合物(B3)为下式的那些:
其中
R5为氢或C1至C4烷基,
t、u、v和w彼此独立地各自为0,或1至6,优选1至4,且更优选1至3的正整数,
对于i=1至t、1至u、1至v和1至w,Zi彼此独立地各自选自基团-CH2-CH2-O-、-CH2-CH(CH3)-O-、-CH(CH3)-CH2-O-、-CH2-C(CH3)2-O-、-C(CH3)2-CH2-O-、-CH2-CHVin-O-、-CHVin-CH2-O-、-CH2-CHPh-O-和-CHPh-CH2-O-,优选选自基团-CH2-CH2-O-、-CH2-CH(CH3)-O-和-CH(CH3)-CH2-O-,且更优选为-CH2-CH2-O-。
预期的二醇包括乙二醇、二乙二醇、三乙二醇、1,2-丙二醇、1,3-丙二醇、1,1-二甲基-1,2-乙二醇、2-丁基-2-乙基-1,3-丙二醇、2-乙基-1,3-丙二醇、2-甲基-1,3-丙二醇、新戊二醇、羟基特戊酸酯、1,2-丁二醇、1,3-丁二醇或1,4-丁二醇、1,6-己二醇、1,10-癸二醇、双(4-羟基环己烷)异亚丙烷、四甲基环丁二醇、1,2-环己二醇、1,3-环己二醇或1,4-环己二醇、环辛二醇、降莰烷二醇、蒎烷二醇、十氢萘二醇、2-乙基-3-己二醇、2,4-二乙基-1,3-辛二醇、2,2-双(4-羟基环己基)丙烷、1,1-环己烷二甲醇、1,2-环己烷二甲醇、1,3-环己烷二甲醇和1,4-环己烷二甲醇、1,2-环己二醇、1,3-环己二醇或1,4-环己二醇,优选1,2-丙二醇、乙二醇、2,2-二甲基-1,2-乙二醇、1,3-丙二醇、1,2-丁二醇、1,4-丁二醇、3-甲基-1,5-戊二醇、2-乙基-1,3-己二醇、2,4-二乙基-1,3-辛二醇和1,6-己二醇。
预期的三醇包括三羟甲基丁烷、三羟甲基丙烷、三羟甲基乙烷和丙三醇。
化合物(B3)的实例为三羟甲基丁烷、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、丙三醇、双(三羟甲基丙烷)和双甘油,以及它们的每个羟基被乙氧基化和/或丙氧基化、优选被乙氧基化1至6次,优选1至4次,且更优选1至3次的产物;优选为丙三醇、三羟甲基丙烷、季戊四醇、乙氧基化最多达18次的丙三醇、丙氧基化最多达18次的丙三醇、乙氧基化最多达18次的三羟甲基丙烷和混合进行乙氧基化和丙氧基化最多达18次的三羟甲基丙烷;特别优选为丙三醇、三羟甲基丙烷和乙氧基化最多达18次的三羟基丙烷。
组分(C)包括具有至少7个,优选至少10个环氧乙烷基团的一元醇。
一般而言,组分(C)包括不小于30个环氧乙烷基团,优选不小于25个,且更优选不小于20个环氧乙烷基团。
在上下文中,环氧乙烷基团为重复纳入于组分(C)中的基团-CH2-CH2-O。
合适的一元醇——其乙氧基化产物可用作组分(C)——包括甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、正己醇、正庚醇、正辛醇、正癸醇、正十二醇(月桂醇)、2-乙基己醇、环戊醇、环己醇、环辛醇和环十二醇。上述C1至C4烷醇是优选的,且甲醇是特别优选的。
特别优选的化合物(C)为通过烷氧基化以下化合物而获得的聚环氧烷聚醚醇
以下通式的单羟基化合物
R1-O-H
或以下通式的仲单胺
R2R3N-H,
其中
R1、R2和R3彼此独立地各自为C1-C18烷基、未被中断或被一个或多个氧原子和/或硫原子中断和/或被一个或多个取代或未被取代的亚氨基中断的C2-C18烷基、或为C6-C12芳基、C5-C12环烷基或含有氧、氮和/或硫原子的5元或六元杂环基,或者R2和R3一起形成不饱和环、饱和环或芳环,其未被中断或被一个或多个氧原子和/或硫原子中断和/或被一个或多个取代或未被取代的亚氨基中断,所述基团各自可被官能团、芳基、烷基、芳氧基、烷氧基、卤素、杂原子和/或杂环基取代。
R1优选为C1至C4烷基,即甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基或叔丁基;R1非常优选为甲基。
合适的单官能起始分子的实例为饱和一元醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、异构的戊醇、异构的己醇、异构的辛醇和异构的壬醇、正癸醇、正十二烷醇、正十四烷醇、正十六烷醇、正十八烷醇、环己醇、环戊醇、异构的甲基环己醇或异构的羟甲基环己烷、3-乙基-3-羟甲基环氧丁烷或四氢糠醇;不饱和醇,例如烯丙醇、1,1-二甲基烯丙醇或油醇;芳族醇,例如苯酚、异构的甲酚或甲氧基苯酚;芳脂族醇,例如苄基醇、茴香醇或肉桂醇;一元仲胺(secondary monoamine),例如二甲胺、二乙胺、二丙胺、二异丙胺、二正丁胺、二异丁胺、双(2-乙基己基)胺、N-甲基环己基胺和N-乙基环己基胺或二环己基胺;杂环仲胺,例如吗啉、吡咯烷、哌啶或1H-吡唑;以及氨基醇,例如2-二甲基氨基乙醇、2-二乙基氨基乙醇、2-二异丙基氨基乙醇、2-二丁基氨基乙醇、3-(二甲基氨基)-1-丙醇或1-(二甲基氨基)-2-丙醇。
优选的化合物(C)为使用上述类型的饱和脂族或脂环族醇作为起始分子而制备的基于聚环氧烷聚醚醇的聚醚醇。非常特别优选使用烷基中具有1至4个碳原子的饱和脂族醇而制备的基于聚环氧烷聚醚醇的那些聚醚醇。特别优选由甲醇制备的聚环氧烷聚醚醇。
一元的聚环氧烷聚醚醇的每个分子通常平均包含7至30,优选7至25,更优选7至20、非常特别优选10至20个环氧乙烷单元。
因此,优选的聚醚醇(C)为下式的化合物
R1-O-[-Xi-]k-H
其中
R1如上所定义,
k为5至30,优选7至25,更优选7至20,且特别是10至20的整数,以及
对于i=1至k,Xi各自为-CH2-CH2-O-。
聚醚醇还可包括作为亲水性合成组分的少量的具有阴离子或阳离子基团(例如羧酸酯基、磺酸酯基或铵基)的其他对异氰酸酯具有反应性的化合物。然而,这是较不优选的。
为了制备水可乳化型多异氰酸酯,在40至180℃,优选50至150℃的温度下,在NCO/OH当量比为至少5:1,优选至少7:1,更优选至少10:1,且NCO/OH当量比为最多达100:1,优选最多达50:1,更优选最多达30:1,非常优选最多达25:1,且更特别最多达18:1的条件下,将至少部分且优选全部量的起始组分(A)和(B)以及(C)与至少部分且优选全部量的化合物(B)和/或(C)进行反应。
虽然较不优选,但也可以首先将起始组分(A)至少部分地与(B)反应且随后仅与(C)反应,或相反地,首先将起始组分(A)至少部分地与(C)反应且随后仅与(B)反应。然而,优选将(A)、(B)和(C)同时反应。
将反应混合物与组分(C)以一定量进行反应,以使最终产物具有的以44g/mol计的环氧乙烷基团含量为至少12重量%,优选至少14重量%,且更优选至少15重量%,基于全部组分(A)、(B)和(C)的总量计。所述环氧乙烷基团含量通常不超过25重量%,优选不超过23重量%,更优选不超过20重量%。
反应时间通常为10分钟至5小时,优选15分钟至4小时,更优选20至180分钟,且非常优选30至120分钟。
为了加速反应,可任选使用合适的催化剂。
其为已知用于这些目的的常规催化剂,实例为记载于GB-A-0 994 890中的金属羧酸盐、金属螯合物或叔胺类、记载于US-A-3 769 318中的烷基化试剂或例如记载于EP-A-0000 194中的强酸。
特别地,合适的催化剂为锌化合物,例如硬脂酸锌(II)、正辛酸锌(II)、2-乙基-1-己酸锌(II)、环烷酸锌(II)或乙酰丙酮锌(II);锡化合物,例如正辛酸锡(II)、2-乙基-1-己酸锡(II)、月桂酸锡(II)、二丁基氧化锡、二丁基二氯化锡、二乙酸二丁基锡、二月桂酸二丁基锡、二马来酸二丁基锡或二乙酸二辛基锡、三(乙基乙酰乙酸)铝、氯化铁(III)、辛酸钾;锰化合物、钴化合物、铋化合物、Zn(II)化合物、Zr(IV)化合物或镍化合物,以及强酸,例如三氟乙酸、硫酸、盐酸、氢溴酸、磷酸或高氯酸,或例如这些催化剂的任意所需混合物。
虽然较不优选,但是用于所述方法的合适的催化剂也可为记载于例如EP-A-0 649866中第4页第7行至第5页第15行中的那些催化剂。
用于本发明方法的优选催化剂为上述类型的锌化合物。非常特别优选使用正辛酸锌(II)、2-乙基-1-己酸锌(II)和/或硬脂酸锌(II)。
如果存在,这些催化剂使用量为0.001%至5重量%,优选0.005%至1重量%,基于反应物的总重量计。
用于制备聚氨酯制剂的加聚反应可特别优选地在铯盐存在下进行,如DE10161156中所记载。优选的铯盐是其中使用了以***离子的化合物:F–、Cl–、ClO–、ClO3 –、ClO4 –、Br–、I–、IO3 –、CN–、OCN–、NO2 –、NO3 –、HCO3 –、CO3 2–、S2–、SH–、HSO3 –、SO3 2–、HSO4 –、SO4 2–、S2O2 2–、S2O4 2–、S2O5 2–、S2O6 2–、S2O7 2–、S2O8 2–、H2PO2 –、H2PO4 –、HPO4 2–、PO4 3–、P2O7 4–、(OCnH2n+1)–、(CnH2n– 1O2)–、(CnH2n–3O2)–和(Cn+1H2n–2O4)2–,n代表1至20的数。
特别优选的化合物是羧酸铯,其中阴离子为式(CnH2n–1O2)–或(Cn+1H2n–2O4)2–的阴离子,其中n为1至20。特别优选的铯盐含有通式(CnH2n–1O2)–的一元羧酸阴离子,其中n代表1至20的数。此处可特别提及的是甲酸盐、乙酸盐、丙酸盐、己酸盐和2-乙基己酸盐。
每千克无溶剂反应混合物使用0.01至10mmol铯盐。每千克无溶剂反应混合物优选使用0.05至2mmol铯盐。
所述铯盐可以以固体形式加入至反应混合物中,但优选以溶解形式加入。合适的溶剂是极性非质子溶剂或质子溶剂。除水之外,特别合适的为醇;特别合适的为多元醇,用作用于聚氨酯的合成单元的为例如乙二醇、丙二醇和丁二醇。使用铯盐可使加聚反应在常规条件下进行。
向反应混合物中的添加过程可通过任意所需的方法进行。因此,例如,可在实际反应开始之前将催化剂混合至多异氰酸酯组分(A)、(B)中和/或混合至组分(C)中。也可以在反应期间的任何时候,或者在氨基甲酸乙酯化(urethanization)反应之后(即,当达到理论上对应于异氰酸酯和羟基的完全转化的NCO含量时)的两级反应过程中,将催化剂加入至反应混合物中。
在本发明的一个优选实施方案中,组分(B)和(C)主要通过氨基甲酸酯基团进行键合,然而通过脲基甲酸酯基团的键合占较小部分。
基于在组分(B)和(C)中与异氰酸酯反应的羟基计,优选大于50摩尔%,更优选至少60摩尔%,非常优选至少66摩尔%,更特别至少75摩尔%,尤其至少80摩尔%,甚至至少90摩尔%的羟基通过氨基甲酸酯基团进行键合。
因此,优选相应地选择反应条件,以使在产物中在组分(B)和(C)中小于10摩尔%的羟基通过脲基甲酸酯基团进行键合。这可例如通过避免EP 959087 A1中记载的用以实现高脲基甲酸酯含量的反应条件类型而实现。
这可优选通过在上述催化剂中选择仅在小程度上形成脲基甲酸酯基团的那些催化剂而实现。
特别地,在催化剂存在下通过将反应温度保持在90℃以下,优选85℃以下,且更优选80℃以下可将脲基甲酸酯基团的形成保持在低水平。
反应过程可通过借助例如滴定分析法测定NCO含量来监测。当到达目标NCO含量时,终止反应。在纯热反应机制的情况下,这可例如通过冷却反应混合物至室温来完成。然而,当使用上述类型的催化剂时,通常通过加入合适的去活化剂来停止反应。合适的去活化剂的实例包括有机或无机酸、相应的酸性卤化物和烷基化试剂。可提及的实例包括磷酸、一氯乙酸、十二烷基苯磺酸、苯甲酰氯、硫酸二甲酯和优选的磷酸二丁酯以及二(2-乙基己基)磷酸酯。去活化剂的用量可为1至200摩尔%,优选20至100摩尔%,基于催化剂的摩尔数计。
所得的多异氰酸酯混合物通常具有优选14.0至20.0重量%,更优选15.0至19.0重量%的NCO含量。
所得的多异氰酸酯混合物在23℃下通常具有3至12Pas,更优选3.5至8Pas的粘度。
在本说明书中,除非另有说明,粘度是在23℃下,根据DIN EN ISO 3219/A.3在具有1000s-1的剪切速度的锥/板体系中记录的。
所述方法可任选地在对异氰酸酯基团呈惰性的合适的溶剂(D)中进行。合适的溶剂的实例是本身已知的常规油漆溶剂,例如乙酸乙酯、乙酸丁酯、乙二醇单甲醚乙酸酯或乙二醇单***乙酸酯、乙酸1-甲氧基-2-丙酯、乙酸3-甲氧基正丁酯、丙酮、2-丁酮、异丁基甲基酮、4-甲基-2-戊酮、环己酮、环戊酮、甲苯、二甲苯、氯苯、油漆溶剂油、具有相对高取代度的芳族化合物(例如以 和为名称出售的化合物)、丙二醇二乙酸酯、二乙二醇二甲醚、二丙二醇二甲醚、二乙二醇***乙酸酯和二乙二醇丁醚乙酸酯、N-甲基吡咯烷酮、N-甲基己内酰胺,以及优选在EP-A1 697 424,第4页第4行至第32行指定的碳酸酯或内酯,更优选碳酸二甲酯、碳酸二乙酯、碳酸1,2-亚乙酯(1,2-ethylene carbonate)、碳酸1,2-亚丙酯(1,2-propylenecarbonate)、内酯(例如β-丙内酯、γ-丁内酯、ε-己内酯和ε-甲基己内酯)或这些溶剂的任意所需的混合物。
也可以首先在无溶剂的条件下制备异氰酸酯,然后使用溶剂(D)来处理由此获得的产物。
基于全部混合物(组分(A)、(B)和(C)的总量)计,溶剂(D)可以0至60重量%,优选0至50重量%的量存在。
为了制备水性分散体,混合物可优选分散于水中;其中特别优选将混合物混合至水性分散体中。
多异氰酸酯制剂适合于改性水性涂层材料(油漆、防护涂料),例如木材、薄木片、纸、纸板、卡纸板、纺织品、皮革、无纺布、塑料表面、玻璃、陶瓷、矿物建筑材料例如水泥模塑物和纤维水泥板、金属或涂覆金属、胶黏剂或浸渍组合物,该制剂用于染色,例如基于固体含量为5至40重量%,优选5至20重量%的水性分散体或溶液。合适的涂层材料包括烯属不饱和单体的均聚物或共聚物或聚氨酯的本身已知的水性分散体,或者天然物质如酪蛋白的溶液。
多异氰酸酯制剂通常加入至水性涂层材料中的量为1重量%至25重量%,优选2.5重量%至20重量%,基于涂层材料的固体含量计。
多异氰酸酯制剂例如可以聚氨酯分散体的形式作为单组分涂料组合物使用,或以与含羟基粘合剂的混合物形式作为双组分聚氨酯涂料组合物使用。
将它们以已知的方式施用至基材上,例如以5至50g固体/m2的速度喷涂。
烯属不饱和单体的均聚物或共聚物的合适的分散体为,例如,基于具有2至18、优选2至4个碳原子的羧酸的乙烯基酯、例如特别是乙酸乙烯酯,如果需要与基于烯属不饱和单体总量计最多达70重量%的其他烯属不饱和单体的均聚物或共聚物的常规分散体;和/或具有1至18、优选1至4个碳原子的醇的(甲基)丙烯酸酯,例如特别是(甲基)丙烯酸的甲酯、乙酯、丙酯、羟乙酯、羟丙酯,如果需要与最多达70重量%的其他烯属不饱和单体的均聚物或共聚物;和/或具有大约20至60重量%的丁二烯含量的丁二烯-苯乙烯共聚物;和/或其他二烯聚合物或共聚物,例如聚丁二烯或丁二烯与其他烯属不饱和单体如苯乙烯、丙烯腈和/或甲基丙烯腈的共聚物,和/或2-氯-1,3-丁二烯,如果需要与上述类型的其他烯属不饱和单体,例如具有大约30重量%至40重量%、特别是约36重量%的氯含量的那些烯属不饱和单体的聚合物或共聚物的水性分散体。
优选为90至99.5重量%的含有1至4个碳原子的链烷醇的丙烯酸酯或甲基丙烯酸酯与0.5至10重量%(各自基于共聚物计)的羟烷基中具有2至20个碳原子的羟烷基丙烯酸酯和羟烷基甲基丙烯酸酯(例如羟乙基、羟丙基或羟丁基的丙烯酸酯或甲基丙烯酸酯)的共聚物的水分散体。这些分散体是本身已知的,且能够通过乳液聚合反应进行常规制备(参见Houben-Weyl,Methoden der organischen Chemie,第4版,第E20卷,第217页及其后)。
合适的水性聚氨酯分散体是本身已知的那些,例如US-A 3,479,310、GB-A 1,076,688、US-A 4,108,814、US-A 4,092,286、DE-A 2 651 505、US-A 4,190,566、DE-A 2 732131或DE-A 2 811 148中所记载。
使用的水性分散体可包含常规的助剂和添加剂。这些包括例如填料,如石英粉、石英砂、高分散二氧化硅、重晶石、碳酸钙、白垩、白云石或滑石,它们经常与合适的湿润剂如多磷酸盐(如六偏磷酸钠、萘磺酸钠、聚丙烯酸的铵盐或钠盐)一起使用,湿润剂的添加量通常为0.2重量%至0.6重量%,基于填料计。
其他合适的助剂为有机增稠剂(其用量为0.01重量%至1重量%,基于分散体计),如纤维素衍生物、藻酸盐、淀粉或淀粉衍生物或聚丙烯酸;或无机增稠剂(其用量为0.05重量%至5重量%,基于分散体计),如膨润土。
还可将用于防腐的杀真菌剂加入至分散体中。其用量通常为0.02重量%至1重量%,基于分散体计。合适的杀真菌剂的实例为苯酚和甲酚衍生物以及有机锡化合物。
用于浸渍的基材为例如合成或非合成的纤维,和/或包含这些纤维的无纺布或机织物。
混合物可被细分散在水性分散体中。所得的分散体在贮存期间非常稳定。此外,为了设定分散体的所需性能或获得应用中的所需性能,需要加入少量的水可乳化型多异氰酸酯。
当然,混合物可以含有涂料技术的常规助剂和添加剂。这些包括例如消泡剂、增稠剂、流平助剂、颜料、乳化剂、分散助剂和溶剂。通过加入水来设定所需的加工粘度。
为了制备分散体,在大多情况下采用简单的乳化技术(例如使用机械搅拌器),或在很多情况下简单地手工混合两个组分是足够的,其可获得具有很好性能的分散体。然而,当然也可使用具有相对高剪切能量的混合技术,例如射流裂散。
包含所述混合物的涂层材料可在汽车修补区域或大型车辆的涂装中特别用作底漆、表面涂料剂(surfacer)、有颜色的面漆材料和清漆。所述涂层材料特别适用于需要特别高的应用可靠性、户外风化稳定性、光学性能、耐溶剂性、耐化学性和耐水性的应用中,例如汽车修补或大型车辆的涂装。
包含所述混合物的涂层材料可以通过任意的各种喷涂法(例如气压喷涂法、无空气喷涂法或静电喷涂法)使用单组分或双组分的喷涂装置施用,或通过喷涂法、抹涂法、刮刀涂布法、刷涂法、卷涂法、滚压法(rolling)、辊涂法、浇涂法、层压法、模内涂装法(in-mold coating)或共挤压法施用。
涂层通常在常温条件(即不加热涂层)下干燥或固化。或者,混合物可以用于制备涂层,施用后在高温下,例如在40-250℃,优选40-150℃,且特别是40-100℃下干燥和固化。
以下实施例旨在说明本发明的性质,而非限制性的。
实施例
在本说明书中,除非另有说明,份数应理解为重量份。
多异氰酸酯A:
HDI异氰脲酸酯具有22.2%的NCO含量且在23℃下具有2800mPa*s的粘度(市售可得,购自BASF SE,Ludwigshafen的HI 100)。
聚醚A:
单官能聚环氧乙烷,其使用氢氧化钾催化剂由甲醇开始制备,具有112的OH值(根据DIN 53240)和500g/mol的分子量。仍存在的碱性催化剂残余物随后用乙酸中和,并将产物脱盐。相同的步骤也除去了已形成的乙酸钾。
聚醚B:
双官能聚环氧乙烷,其使用氢氧化钾催化剂制备,具有560的OH值(根据DIN53240)和200g/mol的分子量。随后用乙酸中和仍存在的碱性催化剂残余物。
聚醚C:
三官能聚环氧乙烷,其使用氢氧化钾催化剂由三羟甲基丙烷开始制备,具有600mgKOH/g的OH值(根据DIN 53240)和280g/mol的分子量。随后用乙酸中和仍存在的碱性催化剂残余物。
聚酯醇A:
三官能聚己内酯,其由三羟甲基丙烷开始制备,具有310的OH值(根据DIN 53240)和540g/mol的分子量。
多元醇A:
蓖麻油(164mg KOH/g的OH值)
对比实施例1:
将174g多异氰酸酯A和26g聚醚A在85℃下反应4小时。相应的产物具有17.9%的NCO含量,且在23℃下具有2550mPas的粘度,且仅可部分水分散。
发明实施例1:
将250g多异氰酸酯A、35g聚醚A和5g多元醇A在加入0.06g新癸酸锌(在乙酸丁酯中50%浓度)作为催化剂的条件下反应,在85℃下反应2小时后,NCO含量为17.6%。相应的产物具有3900mPas的粘度(在23℃下)和33Hazen的色值。
发明实施例2:
将250g多异氰酸酯A、45g聚醚A和6g聚酯醇A在无催化剂的条件下反应。在90℃下反应3小时后,NCO含量为16.7%。相应的产物具有4080mPas的粘度(在23℃下)和43Hazen的色值。
发明实施例3:
将250g多异氰酸酯A、40g聚醚A、2g聚醚B和5g多元醇A在加入0.06g二月桂酸二丁基锡作为催化剂的条件下反应。在90℃下反应3小时后,NCO含量为16.8%。相应的产物具有4680mPas的粘度(在23℃下)和76Hazen的色值。
发明实施例4:
将250g多异氰酸酯A、44g聚醚A和1.5g聚醚C在加入0.03g二月桂酸二丁基锡作为催化剂的条件下反应。在90℃下反应3小时后,NCO含量为17.1%。相应的产物具有3530mPas的粘度(在23℃下)和42Hazen的色值。
光泽度测定:
组分A:
购自Blanchon的Blumor Intensiv组分。
用二丙二醇二甲醚将100%的多异氰酸酯稀释至70%。然后将5g固化剂加入至45g组分A中。然后,使用木铲以140-180rpm的速度手动搅拌所述制剂约20秒。无需过滤,然后使用150μm的四边式涂布棒(four-way bar applicator),将全部清漆涂布在卡纸板面板上,干燥后(在60℃下干燥30分钟),使用购自BYK的micro TRI glossμ仪器从两个不同角度(20°和60°)测定光泽度。
Claims (20)
1.水可乳化型多异氰酸酯,其包含:
(A)至少一种基于至少一种(环)脂族二异氰酸酯的多异氰酸酯,其中所述多异氰酸酯为六亚甲基1,6-二异氰酸酯的异氰脲酸酯,
(B)至少一种多元醇,其具有:
-至少为2且最多达4的羟基官能度,以及
-至少为92至1500g/mol的数均摩尔质量,
(C)至少一种含有环氧乙烷基团的一元醇,其具有至少7个环氧乙烷基团,以及
(D)任选的溶剂,其中
-(A)中的NCO基团与(B)和(C)中的羟基基团的比为至少5:1至100:1,
-以44g/mol计的环氧乙烷基团的量为至少12重量%,基于(A)、(B)和(C)的总量计,
-组分(B)的量为0.5至4.0重量%,
-组分(C)的量为至少5重量%且最多达25重量%,以及
-根据DIN EN ISO 3219/A.3,在23℃下,在具有1000s-1的剪切速率的锥/板体系中的粘度为2500mPas至12 000mPas。
2.权利要求1的水可乳化型多异氰酸酯,其中所述以44g/mol计的环氧乙烷基团的量为至少14重量%,基于(A)、(B)和(C)的总量计。
3.权利要求2的水可乳化型多异氰酸酯,其中所述以44g/mol计的环氧乙烷基团的量为至少15重量%,基于(A)、(B)和(C)的总量计。
4.权利要求1的水可乳化型多异氰酸酯,其中化合物(B)包含:
(B1)至少一种脂肪酸与至少一种多元醇的酯化产物,和/或
(B2)至少一种羟基烷烃羧酸或相应的内酯与至少一种多元醇的酯化产物,和/或
(B3)至少一种任选的烷氧基化的多元醇。
5.权利要求4的水可乳化型多异氰酸酯,其中所述化合物(B1)为具有160至173mg KOH/g的OH值的蓖麻油。
6.权利要求4的水可乳化型多异氰酸酯,其中所述化合物(B2)为以下化合物:
其中
R4为氢或C1至C4烷基,
k、l、m和q彼此独立地各自为1至5的正整数,
对于每个i,Yi彼此独立地各自为基团-[-O-(CH2)z-(C=O)-]-,以及
z为2至6的正整数。
7.权利要求6的水可乳化型多异氰酸酯,其中k、l、m和q彼此独立地各自为1至4的正整数。
8.权利要求7的水可乳化型多异氰酸酯,其中k、l、m和q彼此独立地各自为2至3的正整数。
9.权利要求6的水可乳化型多异氰酸酯,其中z为2至5的正整数。
10.权利要求9的水可乳化型多异氰酸酯,其中z为3至5的正整数。
11.权利要求4的水可乳化型多异氰酸酯,其中所述化合物(B3)为下式的化合物:
其中
R5为氢或C1至C4烷基,
t、u、v和w彼此独立地各自为0,或1至6的正整数,
对于i=1至t、1至u、1至v和1至w,Zi彼此独立地各自选自-CH2-CH2-O-、-CH2-CH(CH3)-O-、-CH(CH3)-CH2-O-、-CH2-C(CH3)2-O-、-C(CH3)2-CH2-O-、-CH2-CHVin-O-、-CHVin-CH2-O-、-CH2-CHPh-O-和-CHPh-CH2-O-。
12.权利要求11的水可乳化型多异氰酸酯,其中t、u、v和w彼此独立地各自为1至4的正整数。
13.权利要求12的水可乳化型多异氰酸酯,其中t、u、v和w彼此独立地各自为1至3的正整数。
14.权利要求11的水可乳化型多异氰酸酯,其中Zi彼此独立地各自选自-CH2-CH2-O-、-CH2-CH(CH3)-O-和-CH(CH3)-CH2-O-。
15.权利要求14的水可乳化型多异氰酸酯,其中Zi为-CH2-CH2-O-。
16.权利要求1的水可乳化型多异氰酸酯,其中化合物(C)为下式的化合物:
R1-O-[-Xi-]k-H
其中
R1为C1-C18烷基、任选地被一个或多个氧原子和/或硫原子中断和/或被一个或多个取代或未被取代的亚氨基中断的C2-C18烷基,或为C6-C12芳基、C5-C12环烷基或含有氧、氮和/或硫原子的5元或六元杂环基,
k为5至35的整数,以及
对于i=1至k,Xi彼此独立地各自为-CH2-CH2-O-。
17.权利要求16的水可乳化型多异氰酸酯,其中k为7至30的整数。
18.权利要求17的水可乳化型多异氰酸酯,其中k为7至25的整数。
19.权利要求18的水可乳化型多异氰酸酯,其中k为10至22的整数。
20.前述权利要求中任一项的水可乳化型多异氰酸酯在用于木材、薄木片、纸、纸板、卡纸板、纺织品、皮革、无纺布、塑料表面、玻璃、陶瓷、矿物建筑材料、金属或涂覆金属的涂层材料中的用途。
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2013
- 2013-09-16 EP EP13763225.3A patent/EP2900735B1/de active Active
- 2013-09-16 CN CN201380050835.1A patent/CN104736605B/zh active Active
- 2013-09-16 SG SG11201501915WA patent/SG11201501915WA/en unknown
- 2013-09-16 JP JP2015533525A patent/JP2015532314A/ja active Pending
- 2013-09-16 US US14/430,661 patent/US9683127B2/en active Active
- 2013-09-16 WO PCT/EP2013/069082 patent/WO2014048776A2/de active Application Filing
- 2013-09-16 KR KR1020157011142A patent/KR20150063506A/ko not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102277081A (zh) * | 2010-03-25 | 2011-12-14 | 巴斯夫欧洲公司 | 具有改进性能的水可乳化的异氰酸酯 |
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KR20150063506A (ko) | 2015-06-09 |
SG11201501915WA (en) | 2015-05-28 |
EP2900735A2 (de) | 2015-08-05 |
JP2015532314A (ja) | 2015-11-09 |
WO2014048776A3 (de) | 2014-05-30 |
EP2900735B1 (de) | 2016-09-14 |
CN104736605A (zh) | 2015-06-24 |
US20150225605A1 (en) | 2015-08-13 |
WO2014048776A2 (de) | 2014-04-03 |
US9683127B2 (en) | 2017-06-20 |
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