CN1926165A - 疏水性低粘度多元醇 - Google Patents
疏水性低粘度多元醇 Download PDFInfo
- Publication number
- CN1926165A CN1926165A CNA2005800061979A CN200580006197A CN1926165A CN 1926165 A CN1926165 A CN 1926165A CN A2005800061979 A CNA2005800061979 A CN A2005800061979A CN 200580006197 A CN200580006197 A CN 200580006197A CN 1926165 A CN1926165 A CN 1926165A
- Authority
- CN
- China
- Prior art keywords
- polyvalent alcohol
- weight
- hydrophobicity polyvalent
- viscosity
- coating
- 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.)
- Granted
Links
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- 229920001228 polyisocyanate Polymers 0.000 claims description 28
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- KVVSCMOUFCNCGX-UHFFFAOYSA-N cardol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1 KVVSCMOUFCNCGX-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 13
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 13
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 13
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 13
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 13
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- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000004593 Epoxy Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
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- 235000020226 cashew nut Nutrition 0.000 claims description 6
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- 239000007788 liquid Substances 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
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- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- DLGUAUVHTOCKTB-UHFFFAOYSA-N 1-isocyanatononane Chemical class CCCCCCCCCN=C=O DLGUAUVHTOCKTB-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 description 1
- ZRXHQNQYIKVKNQ-UHFFFAOYSA-N 2-ethylhexanoic acid;zinc Chemical compound [Zn].CCCCC(CC)C(O)=O ZRXHQNQYIKVKNQ-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- LPIOVDDQPPSVFH-UHFFFAOYSA-N 2-pentadeca-1,3-dienylphenol Chemical compound CCCCCCCCCCCC=CC=CC1=CC=CC=C1O LPIOVDDQPPSVFH-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000660443 Encyclops Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- KAOMOVYHGLSFHQ-UTOQUPLUSA-N anacardic acid Chemical compound CCC\C=C/C\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O KAOMOVYHGLSFHQ-UTOQUPLUSA-N 0.000 description 1
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- ADFWQBGTDJIESE-UHFFFAOYSA-N anacardic acid 15:0 Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O ADFWQBGTDJIESE-UHFFFAOYSA-N 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 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 1
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- QATBRNFTOCXULG-UHFFFAOYSA-N n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCNCCN QATBRNFTOCXULG-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 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 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/487—Polyethers containing cyclic groups
- C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
-
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Abstract
本发明涉及新型的低粘度疏水性多元醇及其制备方法，以及基于该疏水性多元醇的特别适用于地板涂料底漆的无溶剂粘合剂混合物。
Description
本发明涉及新型的疏水性低粘度多元醇及其制备方法，以及基于该疏水性低粘度多元醇的特别适用于地板涂料底漆的无溶剂粘合剂混合物。
现有技术中的无溶剂两组分(2K)涂料体系基本上分为环氧树脂(2K EP)体系和聚氨酯(2K PU)体系。
基于2K EP体系的涂料具有良好的机械强度，同时又对溶剂和化学品具有高耐受性。另外，它们以极好的基材粘合性而著名。这种涂料明显的缺点是弹性差，特别是在低温时更是如此。这种脆性导致涂层遮蔽裂缝的能力差，以至于会在基材上发生侵蚀。另一个缺点是该涂料对有机酸的耐受性非常低。这是应用于地板行业中最主要的问题，因为在该行业中有机酸常作为废产物释放。
另一方面，硬度和弹性兼而有之是2K PU涂料的突出特点，也是比2K EP涂料优越的最突出之处。而且，在对溶剂和化学品的耐受性差不多的情况下，2K PU涂料对有机酸的耐受性要明显好于2K EP涂料。
考虑到环境方面的原因，涂料组合物应该是不含溶剂的，特别是在厚浆型(high-build)应用中，诸如地板涂料。这意味着粘合剂组分的固有粘度应该低。
在基于2K PU体系的厚浆型应用中，由于水-异氰酸酯反应形成CO2，存在形成气泡的风险。因此，原料具有非常低的吸水率以至于此类涂料即使在潮湿环境下也可以无泡地施涂，这一点非常重要。因为羟基官能组分一般来说比多异氰酸酯组分更亲水，所以使用疏水性羟基-官能组分显得尤为重要。
可以各种类型的化学结构为基础建立2K PU涂料的羟基-官能粘合剂组分。
虽然聚酯多元醇以低粘度和相对低吸水率而著名，但是它们的水解稳定性低，因而严重限制了它们在金属基材的耐腐蚀保护和涂布矿物(碱性)基材中的应用。
基于聚丙烯酸酯多元醇的2K PU涂料虽然以有效的耐水解性而著名，但是它们有粘度较高的缺点。因此，总是需要加入溶剂或活性稀释剂如聚醚多元醇或多官能醇来调节粘度。与聚醚多元醇单独用作交联剂时一样，这通常会提高吸水率。
现有技术中通过使用蓖麻油能够使无溶剂多元醇具有足够的疏水性(例如，Saunders，Frisch；Polyurethanes，Chemistry and Technology，第一部分Chemistry，第48至53页)。但是，这样生产的2K PU涂料对水解不稳定。
由腰果壳液(CNSL；腰果壳油)得到的树脂用于油漆和涂料(Shukia等人，在Paintindia中，2002年2月，第29-32页，Nayak，Natural Oil-Based Polymers：Opportunities and Challenges，在J.M.S.-Rev.Macromol.Chem.Phys.中，C40(1)，12-18，2000)。这类产品疏水性非常强，并且因为没有酯键，所以它们对水解稳定。CNSL基树脂含有酚类OH基，可用来通过与多异氰酸酯反应而发生交联。但是，缺点是形成的基于苯酚的氨基甲酸酯键是不稳定的，在潮湿、碱性条件下会再裂解。
J48-29530描述了CNSL-醛或腰果酚-醛缩合物与环氧烷烃如环氧丙烷的反应，其中酚类OH基与羟基通过脂族基连接。这些产品的缺点是粘度较高，必须加入溶剂以提高可操作性。
因此，本发明的目的是提供一种疏水性低粘度多元醇组分，该组分可进一步加工为无溶剂的粘合剂混合物，基于该粘合剂混合物的涂料没有上述的欠缺耐受性的缺点，特别是在厚浆型应用中。
目前已经发现，环氧烷烃与腰果酚贫化的CNSL的特定组成加合物具有所需的多元醇性质。
本发明提供一种制备疏水性多元醇的方法，所述疏水性多元醇的OH值为140至220毫克KOH/克，23℃的粘度为1000至4000mPas，所述方法包括使A)与B)反应，其中：
A)为具有以下特征的混合物：
OH含量为180至300毫克KOH/克，
23℃的粘度为5000至20000mPas，
平均OH官能度为2.8至4.5，并且A)包含：
5至20重量％的腰果酚(3-十五碳二烯基(pentadecadienyl)苯酚)，
5至10重量％的强心酚(3-十五碳二烯基间苯二酚)和
1至5重量％的6-甲基强心酚(2-甲基-3-十五碳二烯基间苯二酚)，
B)为环氧烷烃(AO)，AO单体加成到组分A)的AO-活性基团上，
A)与B)的用量之比为1∶9至9∶1，腰果酚、强心酚和6-甲基强心酚加上组分A)的剩余成分的量之和为100重量％。
另外，本发明提供依据本发明的方法制备的多元醇。
工业上，腰果酚(3-十五碳二烯基苯酚)由腰果核的壳和/或其含有的CNSL得到。
从腰果的核和壳之间的层中提取CNSL。该中间层主要含有漆树酸(2-羧基-3-十五碳二烯基苯酚)和双键含量不同的相关酸，以及强心酚(间-十五碳二烯基间苯二酚)。通过加热从该中间层中提取液体，在此过程中，脱去酸的羧基。这样得到的产物包含腰果酚(I)、强心酚(II)和双键数不同的相关化合物。这种提取物的典型组成如下：
饱和或顺式-不饱和的侧链可以进一步反应，通过聚合反应形成高分子量化合物(“聚合物”)。
最后，通过蒸馏从CNSL中分离出腰果酚。余下的剩余物中不仅含有高分子量有机化合物，而且通常含有5至20重量％的腰果酚剩余物、5至10重量％的强心酚(3-十五碳二烯基间苯二酚)和1至5重量％的6-甲基强心酚(2-甲基-3-十五碳二烯基间苯二酚)。
A)中优选使用由腰果壳液(CNSL)制备腰果酚中得到的这种剩余物。该剩余物含有所述量的腰果酚、强心酚和6-甲基强心酚，通常还含有60至80重量％、优选65至75重量％的数均分子量Mn＞700克/摩尔的可能酚类OH-官能有机化合物，所用剩余物的所述组分的量之和为100重量％。
较佳地，组分A)的混合物的OH含量为200至270毫克KOH/克。
较佳地，组分A)的混合物23℃的粘度为5000至20000mPas，优选平均OH官能度为3至4。
这种由腰果酚制备中得到的剩余物可从比利时的Cardolite Chemica N.V.以牌号NX-4670购得。它们的OH含量为207至250毫克KOH/克，23℃的粘度为5000至20000mPas。
较佳地，在本发明方法中，A)与B)的用量之比为1∶5至5∶1。
通过将组分B)的化合物加聚到组分A)的含有活性氢原子的基团上来进行组分A)的烷氧基化反应。
使用的环氧烷烃优选为环氧乙烷、环氧丙烷、环氧丁烷和它们的混合物。当使用两种或更多种环氧烷烃类型时，它们可以发生嵌段或者无规加聚。其它详细描述见“Ulmanns Encyclopidie der industriellen Chemie”，第A21卷，1992，第670f页。
加聚反应可在无催化剂或使用催化剂下进行。适用于此目的是本领域技术人员已知的催化剂体系和化合物，例如，碱金属氢氧化物或双金属氰化物催化剂(DMC催化剂)。
环氧烷烃加聚到含有活性氢的化合物上的步骤是本领域技术人员熟悉的。通常首先加入组分A)，组分B)在加聚的过程中加入。
本发明的方法一般在20至200℃、优选40至180℃、更优选50至150℃的温度下进行。反应可以在总压为0.001至20巴的条件下进行。加聚反应可以连续或不连续进行，例如以间歇或半间歇过程进行。
由本发明方法得到的多元醇在23℃的粘度优选为1000至3500mPas，OH值为150至220毫克KOH/克。
按照此方式得到的本发明的多元醇的疏水性非常高。因此，它们特别适用于制备用于例如建筑行业中厚浆型应用的2-K聚氨酯涂料体系(2-K PU体系)。
因此，本发明还提供聚氨酯体系(PU体系)，优选为2K PU体系，该体系至少包含：
a)一种或多种本发明的多元醇，和
b)一种或多种多异氰酸酯。
使用的组分b)的多异氰酸通常是平均NCO官能度至少为2、分子量至少为140克/摩尔的有机多异氰酸酯。特别合适的是(i)分子量为140至300克/摩尔的未改性有机多异氰酸酯、(ii)分子量为300至1000克/摩尔的漆用多异氰酸酯和(iii)分子量超过1000克/摩尔的含有氨基甲酸酯基的NCO预聚物，或(i)至(iii)的混合物。
组(i)的多异氰酸酯的例子是1，4-丁二异氰酸酯、1，6-己二异氰酸酯(HDI)、1，5-二异氰酸根合-2，2-二甲基戊烷、2，2，4-和2，4，4-三甲基-1，6-己二异氰酸酯、1-异氰酸根合-3，3，5-三甲基-5-异氰酸甲酯基环己烷(IPDI)、1-异氰酸根合-1-甲基-4-(3)-异氰酸甲酯基环己烷、双-(4-异氰酸根合环己基)甲烷、1，10-癸二异氰酸酯、1，12-十二烷二异氰酸酯、环己烷1，3-和1，4-二异氰酸酯、苯二亚甲基二异氰酸酯异构体、三异氰酸根合壬烷(TIN)、2，4-甲苯二异氰酸酯或它与2，6-甲苯二异氰酸酯的混合物(该混合物优选含有以混合物为基准计最多35重量％的2，6-甲苯二异氰酸酯)、2，2’-、2，4’-、4，4’-二苯基甲烷二异氰酸酯或二苯基甲烷系列的工业级多异氰酸酯混合物或所述异氰酸酯的任何所需混合物。优选采用二苯基甲烷系列的多异氰酸酯，更优选的是异构体混合物的形式。
组(ii)的多异氰酸酯是本领域技术人员已知的漆用多异氰酸酯。术语“漆用多异氰酸酯”在本发明的叙述中是指通过(i)所例举的简单二异氰酸酯的常规低聚反应得到的化合物或化合物的混合物。合适的低聚反应的例子包括碳二亚胺化反应、二聚化反应、三聚化反应、缩二脲化反应、脲形成反应、氨基甲酸酯化反应、脲基甲酸酯化反应和/或形成二嗪结构的成环反应。在“低聚化反应”的过程中，通常上述的两种或更多种反应同时或相继进行。
优选的“漆用多异氰酸酯”(ii)是基于简单二异氰酸酯的缩二脲多异氰酸酯、含有异氰脲酸酯基的多异氰酸酯、含有异氰脲酸酯基和脲二酮(uretdione)基的多异氰酸酯混合物、含有氨基甲酸酯基和/或脲基甲酸酯基的多异氰酸酯、或含有异氰脲酸酯基和脲基甲酸酯基的多异氰酸酯混合物。
这种漆用多异氰酸酯的制备是已知的，且在例如DE-A 1595273、DE-A3700209和DE-A 3900053或EP-A-0330966、EP-A 0259233、EP-A-0377177、EP-A-0496208、EP-A-0524501或US-A 4385171中有所描述。
组(iii)的多异氰酸酯是基于上述简单二异氰酸酯和/或基于漆用多异氰酸酯(ii)和分子量超过300克/摩尔的有机多羟基化合物的常规异氰酸酯官能预聚物。虽然组(ii)的含有氨基甲酸酯基的漆用多异氰酸酯是分子量为62至300克/摩尔的低分子量多元醇(合适的多元醇例如乙二醇、丙二醇、三羟甲基丙烷、丙三醇或这些醇的混合物)的衍生物，但是组(iii)的NCO预聚物使用分子量Mn大于300克/摩尔、优选大于500克/摩尔、更优选为500至8000克/摩尔的多羟基化合物制备。优选的此类多羟基化合物是每个分子中含有2至6个、优选2至3个羟基的化合物，选自醚多元醇、酯多元醇、硫醚多元醇、碳酸酯多元醇和聚丙烯酸酯多元醇和此类多元醇的混合物。
在NCO预聚物(iii)的制备中，所述高分子量多元醇可以与所述低分子量多元醇混合使用，直接得到含有氨基甲酸酯基的低分子量漆用多异氰酸酯(ii)和高分子量NCO预聚物(iii)的混合物。
为了制备NCO预聚物(iii)或其与漆用多异氰酸酯(ii)的混合物，上述例举的二异氰酸酯(i)或(ii)中例举的漆用多异氰酸酯与高分子量羟基化合物或其与所述低分子量多羟基化合物的混合物反应，形成氨基甲酸酯，其中观察到NCO/OH当量比为1.1∶1至40∶1，优选为2∶1至25∶1。任选地，使用过量的可蒸馏原料二异氰酸酯，可以在反应后通过蒸馏除去此二异氰酸酯，得到不含单体的NCO预聚物，即原料二异氰酸酯(i)与纯NCO预聚物(iii)的混合物。
所述多异氰酸酯优选以未封端形式使用，这样得到2K PU体系。或者，也可以使用封端剂对上述的多异氰酸酯的NCO基团进行封端，这样它们可以与本发明的必要多元醇一起配制，得到能稳定储存的1K PU体系。
在本发明的PU体系中，对组分a)、b)和任选的其它成分的量加以选择，使得NCO∶OH的当量比为0.5∶1至2.0∶1，优选为0.8∶1至1.5∶1。
除了a)和b)外，本发明的PU体系可还包含其它成分，例如其它高分子量或低分子量多元醇、催化剂或助剂和添加剂。
可以使用聚氨酯化学领域的技术人员已知的用以加快NCO/OH反应的化合物作为催化剂(参考，“Kunststoff Handbuch 7，Polyurethane”Carl-Hanser-Verlag，Munich-Vienna，1984，第97-98页)。
这些催化剂可包括例如以下所列：叔胺，诸如三乙胺、吡啶、甲基吡啶、苄基二甲基胺、N，N-桥亚乙基哌嗪、N-甲基哌啶、五甲基二亚乙基三胺、N，N-二甲基氨基环己烷、N，N’-二甲基哌嗪，或金属盐，诸如氯化铁(III)、氯化锌、2-乙基己酸锌、辛酸锡(II)、乙基己酸锡(II)、棕榈酸锡(II)、二月桂酸二丁基锡(IV)和乙醇酸钼或这些催化剂的任意所需的混合物。优选使用锡化合物作为组分C)的化合物。
可用于PU体系的助剂或添加剂的例子包括表面活性剂、内脱模剂、填料、染料、颜料、阻燃剂、防水解剂、杀真菌剂、流平助剂、抗氧化剂如2，6-二叔丁基-4-甲基-苯酚、2-羟基苯基苯并三唑类的紫外吸收剂，或氮原子上取代或未取代的HALS化合物类的光稳定剂如Tinuvin292和Tinuvin770DF(CibaSpezialitten GmbH，Lampertheim，德国)或其它商用的普通稳定剂，例如“Lichtschutzmittel für Lacke”(A.Valet，Vincentz Verlag，Hanover，1996)和“Stabilization of Polymeric Materials”(H.Zweifel，Springer Verlag，柏林，1997，附录3，第181-213页)中所述。
为了制备本发明的PU体系，将组分a)、b)和任选的其它交联剂组分相互混合，使得NCO∶OH的当量比为0.5∶1至2.0∶1，优选为0.8∶1至1.5∶1。在各组分混合的过程中或混合之后，如果需要的话，可以与所述助剂和添加剂以及催化剂混合。
本发明的PU体系的施涂可通过本领域技术人员已知的常规技术进行，例如，刷涂、刮涂、喷涂或浸涂。
本发明PU体系的低吸水率非常突出，优选小于7重量％，更优选小于4重量％。为了确定吸水率，将一样品在23℃和97％大气湿度的条件下敞开储存21天，测量重量的增加。基于此杰出的品质，这些体系也可以无泡地施涂并且固化，即使在厚膜的情况下也是如此。
膜厚度优选为0.5至10毫米，优选为0.7至6毫米，尽管这并不排除生产更薄或更厚的涂层。
原则上，本发明的PU体系可用来涂布所有种类的材料。可提及的例子包括玻璃、木材、金属和矿物基材，诸如混凝土。
PU体系优选用来生产保护金属基材抵制机械损害和腐蚀以及保护矿物基材如混凝土抵制环境影响和机械损害的涂层。
实施例
除非另有指示，否则所有百分数都为重量百分数。
依据DIN 53019在23℃使用旋转粘度仪(Viscotester 550，Thermo HakkeGmbH，D-76227 Karlsruhe)测量动态粘度，剪切速率为40s-1。
依据DIN 53505确定肖氏D(Shore D)硬度。
根据样品在23℃和97％的大气湿度下敞开放置21天后重量的增加来确定吸水率。
根据以下等式计算吸水率：
CardoliteNX-4670：
腰果酚制备过程的副产物，含有酚类OH基，OH值为207至250毫克KOH/克，23℃的粘度为5000至20000mPas，Cardolite Chemical N.V.，Belgium。
DesmodurVL：
基于4，4’-二苯基甲烷二异氰酸酯的多异氰酸酯，NCO含量为31.5重量％，23℃的粘度为90mPas，Bayer AG，Leverkusen，德国。
多元醇A-I的制备
将4000克pH为11的CardoliteNX-4670加入到10升反应器中。用氮气使该反应器内的环境变成惰性，加热到130℃。然后在4小时内加入2000克环氧丙烷。在反应结束后，使产物冷却，从反应器中排出。然后将2000克该产物与66.6克水和12％浓度的硫酸在80℃混合60分钟。加入硫酸，直到pH达到7为止。所制得终产物的OH值为188毫克KOH/克，23℃的粘度为1770mPas，pH为7.1，吸水率为5.1重量％。
多元醇A-II的制备
将4800克pH为11的CardoliteNX-4670加入到10升反应器中。用氮气使该反应器内的环境变成惰性，加热到130℃。然后在4小时内加入1200克环氧丙烷。在反应结束后，使产物冷却，从反应器中排出。然后将2000克该产物与66.6克水和12％浓度的硫酸在80℃混合60分钟。加入硫酸，直到pH达到7为止。然后通过蒸馏除去存在的水，使用德国Seitz的深型过滤器T850过滤除去产物中的沉淀盐。终产物的OH值为200毫克KOH/克，23℃的粘度为1416mPas，pH为6.7，吸水率为3.5重量％。
多元醇A-III的制备实施例
将2000克CardoliteNX-4670与水混合，加入12％浓度的硫酸中和，使pH达到7。随后通过蒸馏除去存在的水，使用德国Seitz的深型过滤器T850过滤除去产物中的沉淀盐。终产物的OH值为250毫克KOH/克，粘度为2099mPas，pH为7.9。
实施例1至3
为了制备本发明的2-K PU体系，将多元醇组分与多异氰酸酯组分以NCO/OH为1∶1的比例混合，然后通过将该混合物倒到塑料基材上来施涂该混合物，膜厚为3至5毫米。然后在室温下进行固化。
实施例(1，2本发明，3对比例)
| 组成(重量％) | 1 | 2 | 3 |
| 多元醇A-I多元醇A-II多元醇A-IIIDesmodurVL | 70.230.8 | 67.832.2 | 63.037.0 |
| 处理时间*(分钟)硬度(肖氏D)在70℃在水中储存测试样在以下天数后未受损伤1天7天14天在70℃在10％浓度的氢氧化钠溶液中储存测试样在以下天数后未受损伤1天7天14天 | 5067是是是是是是 | 6570是是是是是是 | --否否否否否否 |
*时间，在该时间内混合物仍然为流体，可手工操作
如对比例3所示，不进行烷氧基化反应，就没有对潮湿和碱性环境的充分耐受性。
Claims (8)
1.一种制备疏水性多元醇的方法，所述疏水性多元醇的OH值为140至220毫克KOH/克，23℃的粘度为1000至4000mPas，所述方法包括使A)与B)反应，其中：
A)为具有以下特征的混合物：
OH含量为180至300毫克KOH/克，
23℃的粘度为5000至20000mPas，
平均OH官能度为2.8至4.5，并且A)包含：
5至20重量％的腰果酚(3-十五碳二烯基苯酚)，
5至10重量％的强心酚(3-十五碳二烯基间苯二酚)和
1至5重量％的6-甲基强心酚(2-甲基-3-十五碳二烯基间苯二酚)，
B)为环氧烷烃(AO)，
使组分B)的AO单体加成到组分A)的AO-活性基团上，
A)与B)的用量之比为1∶9至9∶1。
2.如权利要求1所述的制备疏水性多元醇的方法，其特征在于，在A)中使用由CNSL(腰果壳液)生产腰果酚的过程中所得的剩余物。
3.如权利要求1或2所述的制备疏水性多元醇的方法，其特征在于，在B)中使用环氧乙烷、环氧丙烷、环氧丁烷或它们的混合物。
4.如权利要求1至3中任一项所述的制备疏水性多元醇的方法，其特征在于，A)与B)的用量之比为1∶5至5∶1。
5.通过权利要求1至4中任一项所述的方法制得的疏水性多元醇。
6.聚氨酯(PU)体系，至少包含：
a)一种或多种权利要求5所述的疏水性多元醇，和
b)一种或多种多异氰酸酯。
7.使用权利要求5所述的疏水性多元醇得到的涂料、粘合剂、密封剂或模塑化合物。
8.涂布有权利要求7所述的涂料的基材。
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| DE102004009818.2 | 2004-02-28 | ||
| DE200410009818 DE102004009818A1 (de) | 2004-02-28 | 2004-02-28 | Hydrophobe, niedrigviskose Polyole |
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| EP (1) | EP1723187B1 (zh) |
| JP (1) | JP2007524746A (zh) |
| KR (1) | KR20060133591A (zh) |
| CN (1) | CN100471891C (zh) |
| AT (1) | ATE381581T1 (zh) |
| AU (1) | AU2005217046A1 (zh) |
| BR (1) | BRPI0508189A (zh) |
| DE (2) | DE102004009818A1 (zh) |
| ES (1) | ES2297670T3 (zh) |
| PL (1) | PL1723187T3 (zh) |
| RU (1) | RU2006134266A (zh) |
| UA (1) | UA84454C2 (zh) |
| WO (1) | WO2005082967A1 (zh) |
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| CN102482392A (zh) * | 2009-09-10 | 2012-05-30 | 可泰克斯有限合伙公司 | 基于腰果酚的缔合聚氨酯、相应的缔合增稠剂及其用途 |
| CN102558540A (zh) * | 2011-11-25 | 2012-07-11 | 耐素有限责任公司 | 一种基于植物酚的聚醚多元醇制备方法 |
| CN103102457A (zh) * | 2013-01-21 | 2013-05-15 | 卡德莱化工(珠海)有限公司 | 一种苯乙烯改性的腰果壳油醇酸树脂及其制备方法 |
| WO2015077944A1 (en) * | 2013-11-27 | 2015-06-04 | Dow Global Technologies Llc | Cardanol modified epoxy polyol |
| WO2015077945A1 (en) * | 2013-11-27 | 2015-06-04 | Dow Global Technologies Llc | Cardanol modified epoxy polyol |
| CN105722928A (zh) * | 2013-11-27 | 2016-06-29 | 陶氏环球技术有限责任公司 | 可固化聚氨酯涂料组合物及其制备方法 |
| CN110498907A (zh) * | 2019-08-20 | 2019-11-26 | 浙江万盛股份有限公司 | 一种腰果酚水性环氧固化剂的制备方法 |
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| US7130822B1 (en) * | 2000-07-31 | 2006-10-31 | Cognos Incorporated | Budget planning |
| DE10158693A1 (de) * | 2001-11-29 | 2003-06-26 | Ashland Suedchemie Kernfest | Beschichtete körnige Stoffe |
| CA2482397A1 (en) * | 2003-10-01 | 2005-04-01 | Tse Industries, Inc. | Composite articles having an aesthetic visual surface for use in aqueous environments, and compositions suitable for the preparation thereof |
| US7244772B2 (en) * | 2004-06-30 | 2007-07-17 | Council Of Scientific And Industrial Research | Process for preparing polyurethane polyol and rigid foams therefrom |
| JP5335436B2 (ja) * | 2005-12-30 | 2013-11-06 | カウンシル オブ サイエンティフィック アンド インダストリアル リサーチ | テレケリックウレタンアクリレートｕｖ硬化型プレポリマー材料の合成方法 |
| DE102006037288B4 (de) * | 2006-08-09 | 2019-06-13 | Ask Chemicals Gmbh | Formstoffmischung enthaltend Cardol und/oder Cardanol in Gießereibindemitteln auf Polyurethanbasis, Verfahren zur Herstellung eines Formkörpers sowie Verwendung desselben |
| US7828991B2 (en) | 2006-12-08 | 2010-11-09 | Bayer Materialscience Llc | Polyether polyols based on cashew nutshell liquid and flexible foams |
| DE102008000255A1 (de) | 2008-02-08 | 2009-08-20 | Evonik Goldschmidt Gmbh | Siloxanzusammensetzungen |
| DE102008053715A1 (de) * | 2008-10-29 | 2010-05-12 | Khs Ag | Transportsystem |
| WO2010068673A1 (en) | 2008-12-10 | 2010-06-17 | Valspar Sourcing, Inc. | Polyester polymer having phenolic functionality and coating compositions formed therefrom |
| US8592376B2 (en) * | 2011-12-06 | 2013-11-26 | Avon Products, Inc | Hair care compositions |
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| KR102353047B1 (ko) | 2014-11-05 | 2022-01-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 난연성 폴리올 |
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-
2004
- 2004-02-28 DE DE200410009818 patent/DE102004009818A1/de not_active Withdrawn
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2005
- 2005-02-15 DE DE200550002292 patent/DE502005002292D1/de active Active
- 2005-02-15 ES ES05707388T patent/ES2297670T3/es active Active
- 2005-02-15 PL PL05707388T patent/PL1723187T3/pl unknown
- 2005-02-15 EP EP05707388A patent/EP1723187B1/de not_active Not-in-force
- 2005-02-15 WO PCT/EP2005/001488 patent/WO2005082967A1/de active IP Right Grant
- 2005-02-15 JP JP2007500101A patent/JP2007524746A/ja not_active Withdrawn
- 2005-02-15 KR KR1020067017189A patent/KR20060133591A/ko not_active Application Discontinuation
- 2005-02-15 AU AU2005217046A patent/AU2005217046A1/en not_active Abandoned
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- 2005-02-15 RU RU2006134266/04A patent/RU2006134266A/ru not_active Application Discontinuation
- 2005-02-15 AT AT05707388T patent/ATE381581T1/de active
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102482392A (zh) * | 2009-09-10 | 2012-05-30 | 可泰克斯有限合伙公司 | 基于腰果酚的缔合聚氨酯、相应的缔合增稠剂及其用途 |
| CN102482392B (zh) * | 2009-09-10 | 2014-08-06 | 可泰克斯有限合伙公司 | 基于腰果酚的缔合聚氨酯、相应的缔合增稠剂及其用途 |
| CN102558540A (zh) * | 2011-11-25 | 2012-07-11 | 耐素有限责任公司 | 一种基于植物酚的聚醚多元醇制备方法 |
| CN102558540B (zh) * | 2011-11-25 | 2014-10-29 | 常熟耐素生物材料科技有限公司 | 一种基于植物酚的聚醚多元醇制备方法 |
| CN103102457A (zh) * | 2013-01-21 | 2013-05-15 | 卡德莱化工(珠海)有限公司 | 一种苯乙烯改性的腰果壳油醇酸树脂及其制备方法 |
| CN103102457B (zh) * | 2013-01-21 | 2015-04-29 | 卡德莱化工(珠海)有限公司 | 一种苯乙烯改性的腰果壳油醇酸树脂及其制备方法 |
| WO2015077944A1 (en) * | 2013-11-27 | 2015-06-04 | Dow Global Technologies Llc | Cardanol modified epoxy polyol |
| WO2015077945A1 (en) * | 2013-11-27 | 2015-06-04 | Dow Global Technologies Llc | Cardanol modified epoxy polyol |
| CN105722928A (zh) * | 2013-11-27 | 2016-06-29 | 陶氏环球技术有限责任公司 | 可固化聚氨酯涂料组合物及其制备方法 |
| CN110498907A (zh) * | 2019-08-20 | 2019-11-26 | 浙江万盛股份有限公司 | 一种腰果酚水性环氧固化剂的制备方法 |
| CN110498907B (zh) * | 2019-08-20 | 2021-10-15 | 浙江万盛股份有限公司 | 一种腰果酚水性环氧固化剂的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2005217046A1 (en) | 2005-09-09 |
| DE102004009818A1 (de) | 2005-09-15 |
| PL1723187T3 (pl) | 2008-04-30 |
| JP2007524746A (ja) | 2007-08-30 |
| DE502005002292D1 (de) | 2008-01-31 |
| US7393465B2 (en) | 2008-07-01 |
| EP1723187A1 (de) | 2006-11-22 |
| CN100471891C (zh) | 2009-03-25 |
| WO2005082967A1 (de) | 2005-09-09 |
| EP1723187B1 (de) | 2007-12-19 |
| KR20060133591A (ko) | 2006-12-26 |
| ES2297670T3 (es) | 2008-05-01 |
| UA84454C2 (ru) | 2008-10-27 |
| RU2006134266A (ru) | 2008-04-10 |
| BRPI0508189A (pt) | 2007-08-14 |
| ATE381581T1 (de) | 2008-01-15 |
| US20050192423A1 (en) | 2005-09-01 |
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