CN101287773A - 聚氨酯弹性体 - Google Patents
聚氨酯弹性体 Download PDFInfo
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- CN101287773A CN101287773A CNA2006800380593A CN200680038059A CN101287773A CN 101287773 A CN101287773 A CN 101287773A CN A2006800380593 A CNA2006800380593 A CN A2006800380593A CN 200680038059 A CN200680038059 A CN 200680038059A CN 101287773 A CN101287773 A CN 101287773A
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- Prior art keywords
- ammediol
- polyurethane elastomer
- polycarbonate diol
- alkyl
- polyvalent alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 30
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 35
- 239000004417 polycarbonate Substances 0.000 claims abstract description 35
- 150000002009 diols Chemical class 0.000 claims abstract description 32
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 16
- -1 alkoxylate 2-alkyl-1 Chemical compound 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- LCOOMOSZMKFHOC-UHFFFAOYSA-N 3,3,5,5-tetrakis(hydroxymethyl)oxan-4-ol Chemical compound OCC1(CO)COCC(CO)(CO)C1O LCOOMOSZMKFHOC-UHFFFAOYSA-N 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 239000013638 trimer Substances 0.000 claims description 5
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 claims description 4
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 4
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000007046 ethoxylation reaction Methods 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 229940059574 pentaerithrityl Drugs 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 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 3
- 239000000843 powder Substances 0.000 claims description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 2
- ZHESOIPTRUDICE-UHFFFAOYSA-N CCCCCCCCC.N=C=O.N=C=O.N=C=O Chemical compound CCCCCCCCC.N=C=O.N=C=O.N=C=O ZHESOIPTRUDICE-UHFFFAOYSA-N 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 claims description 2
- WCMXURMPOVCCDW-UHFFFAOYSA-N OC1(CC(=C(C(C(=O)O)=C1)C)C(=O)O)O Chemical compound OC1(CC(=C(C(C(=O)O)=C1)C)C(=O)O)O WCMXURMPOVCCDW-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 2
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical group CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 claims 2
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 2
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000007872 degassing Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical class CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920006309 Invista Polymers 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000000655 anti-hydrolysis Effects 0.000 description 1
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000007600 charging Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/302—Water
- C08G18/307—Atmospheric humidity
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明公开了一种新型聚氨酯弹性体,其通过将至少二、三或多异氰酸酯、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、烷氧基化2-烷基-1,3-丙二醇和/或烷氧基化2,2-二烷基-1,3-丙二醇的聚碳酸酯二醇和/或包含来自两种或多种所述的1,3-丙二醇的单元的至少一种聚碳酸酯二醇和二、三或多元醇反应获得。
Description
技术领域
本发明涉及一种由将至少最少三种基本化合物反应获得的聚氨酯弹性体,所述的基本化合物是二、三或多异氰酸酯,2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、烷氧基化2-烷基-1,3-丙二醇和/或烷氧基化2,2-二烷基-1,3-丙二醇的聚碳酸酯二醇,和二、三或多元醇。
背景技术
聚氨酯弹性体的性质主要由化学组成决定,虽然该性质还取决于用于制备的加工方法。基本原材料的变化产生了这样的弹性体产物,它在很大程度上表现出由主链形成的分段的,坚硬的和柔软嵌段结构的特性。由二、三或多异氰酸酯与二、三或多羟基化合物的反应形成硬链段。现今用于聚氨酯弹性体的二、三或多羟基化合物主要是基于聚酯和聚醚的。基于聚酯时相对于基于聚醚时的优势在于结构强度、耐油性、耐溶剂性和抗氧性,基于聚醚时的优势在于抗水解性和低温柔性。硬链段的熔融温度和这些链段的量决定了聚氨酯弹性体的尺寸热稳定性。硬链段的链间交互作用(主要是氢键)有助于获得高拉伸强度、伸长率、撕裂强度和凝固值。由长链二、三或多元醇产生的柔性链段和这些链段的移动性决定着可逆的弹性体性质。低温韧性、耐溶剂性和抗紫外线性主要由聚氨酯弹性体中的长的柔性软链段调节。已经使用和/或评价了各种类型的二、三和多元醇以便设计弹性体的性质。所述的二、三和多元醇具有通常在600-2500范围内的分子量。一般用于聚氨酯弹性体的二、三或多元醇具有线性结构和两个反应性羟基。聚氨酯弹性体的形态(二级和三级结构)取决于所述链段的长度和化学结构。聚氨酯弹性体的独特性质是由于两相或多相结构。
存在着对于特种多羟基化合物的显著需求,例如与聚酯二元醇、三元醇和多元醇相比,具有改善的抗紫外线性、耐化学品性、耐水解性、抗氧性和耐热性但保持了机械性能的聚碳酸酯二醇和聚己内酯二元醇、三元醇和多元醇。聚碳酸酯二醇(通常是聚酯聚碳酸酯二醇)已经显示出优良的抗紫外线性、耐化学品性、耐水解性和抗氧性以及具有比得上通过聚酯二元醇获得的机械性能。聚酯聚碳酸酯二醇主要用于在这样的领域中的聚氨酯弹性体,其中生产的制品用于水解稳定性和抗微生物性至关重要的领域,如室外管道、运动和休闲应用、用于打印机和造纸机的滚筒。
聚碳酸酯二醇和使用聚碳酸酯二醇制备的聚氨酯公开于例如
-US 5,656,713,其中教导了由脂肪族或环脂族的多异氰酸酯、分子量2000-5000的聚酯、聚碳酸酯和/或聚酯碳酸酯二元醇和一种或多种分子量90-530的二元醇的反应制备的可热成型的聚氨酯,
-EP 0321288,其中教导了具有衍生自聚(戊烷-1,5-碳酸酯)二元醇、聚(己烷-1,6-碳酸酯)二元醇、其共聚物或其混合物的柔性链段的聚氨酯-脲斯潘德克斯弹力纤维、和
-US 4,463,141,其中教导了由聚(四亚甲基醚)二醇和碳酸二烷基酯获得的聚醚碳酸酯二元醇,该二元醇可用于制备聚氨酯。
发明内容
本发明完全出乎意料地提供了相对于现有技术的弹性体具有改善的性质的聚氨酯弹性体。本发明的聚氨酯弹性体是通过将至少二、三或多异氰酸酯、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、烷氧基化2-烷基-1,3-丙二醇、烷氧基化2,2-二烷基-1,3-丙二醇的聚碳酸酯二醇和/或包含来自两个或多个所述1,3-丙二醇的单元的聚碳酸酯二醇和二、三或多元醇反应获得的。此处的二、三和多元醇应被理解为线性或支化的脂肪族、环脂族或芳香族二、三和多元醇和包含来自一种或多种二、三或多元醇和/或一种或多种氧化烯的单元的二聚物、三聚物和聚合物。所述1,3-丙二醇中的烷基优选是具有1-8碳原子的线性或支化的饱和脂肪族烷烃基(alkanyl),烷氧基化同样优选是具有1-20烷氧基单元的乙氧基化、丙氧基化和/或丁氧基化。
所述聚碳酸酯二醇最优选是2-甲基-1,3-丙二醇、2-甲基-2-乙基-1,3-丙二醇、2-乙基-2-丁基-1,3-丙二醇、2,2-二甲基-1,3-丙二醇的至少一种聚碳酸酯二醇和/或是至少一种包含来自两个或多个所述1,3-丙二醇的单元的至少一种聚碳酸酯二醇。在优选实施方案中所述聚碳酸酯二醇的分子量为500-5000,如500-2500,能适当地由例如一或多种所述1,3-丙二醇和二氧化碳源如碳酸二甲酯、碳酸二乙酯和/或脲获得。
在优选实施方案中二、三或多异氰酸酯是脂肪族、环脂族的和/或芳香族二、三或多异氰酸酯,如六亚甲基二异氰酸酯、2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、四甲基二甲苯二异氰酸酯、1,6-己烷二异氰酸酯、三甲基己烷二异氰酸酯、1,12-十二烷二异氰酸酯、环己烷二异氰酸酯、二苯基甲烷二异氰酸酯、异佛尔酮二异氰酸酯和/或壬烷三异氰酸酯。
如上定义的所述的二、三或多元醇优选为至少一种1,ω-二元醇、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、2-烷基-2-羟烷基-1,3-丙二醇和/或2,2-二(羟烷基)-1,3-丙二醇和/或所述二、三或多元醇的至少一种二聚物、三聚物或聚合物和/或至少一种氧化烯如环氧乙烷、环氧丙烷、1,3-环氧丁烷、2,4-环氧丁烷、氧化环己烯、一氧化丁二烯和/或氧化苯乙烯与至少一种1,ω-二元醇、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、2-烷基-2-羟烷基-1,3-丙二醇和/或2,2-二(羟烷基)-1,3-丙二醇和/或所述二、三或多元醇的至少一种二聚物、三聚物或聚合物间的反应产物。优选的二、三和多元醇可适当地用以下物质举例:1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,6-环己烷二甲醇、5,5-二羟基-甲基-1,3-二氧六环、2-甲基-1,3-丙二醇、2-甲基-2-乙基-1,3-丙二醇、2-乙基-2-丁基-1,3-丙二醇、新戊二醇、二羟甲基丙烷、1,1-二羟甲基环己烷、甘油、三羟甲基乙烷、三羟甲基丙烷、一缩二甘油、双三羟甲基乙烷、双三羟甲基丙烷、季戊四醇、双季戊四醇、脱水壬七醇、山梨糖醇、甘露醇和乙氧基化和/或丙氧基化的甘油、三羟甲基乙烷、三羟甲基丙烷、一缩二甘油、双三羟甲基乙烷、双三羟甲基丙烷、季戊四醇、双季戊四醇、脱水壬七醇(anhydroenneaheptitol)、山梨糖醇和/或甘露醇。
无需进一步详细描述,相信本领域熟练技术人员能利用之前的描述将本发明应用到其最大限度。因此,下列优选的具体实施方案当视为仅仅例证性的,但绝不是限制公开内容的其余部分。在下文中,实施例1涉及本发明的范围内的预聚物的制备,该预聚物用于实施例2-4以制备该本发明的弹性体的实施方案。实施例5涉及本发明范围外的预聚物,该预聚物用于实施例6和7中以制备对照弹性体。将实施例2-4、6和7中获得的弹性体在实施例8-10中评价。实施例11涉及制备本发明范围内的预聚物,实施例12-15涉及制备本发明范围外的对照预聚物。实施例11-15的预聚物用于实施例16以制备实施方案的弹性体和对照弹性体,该弹性体在实施例17,18和19中评价。实施方案的弹性体和对照弹性体的评价结果列于表1-6中。
实施例1
将287.30g分子量为1000的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇(OxymerTM B112,Perstorp Specialty Chemicals AB,瑞典)进料到装有温度计、搅拌器、真空装置、加热装置和冷却装置的反应容器中,搅拌下加热到70℃。将聚碳酸酯二醇脱气10分钟,以及将112.70g的异佛尔酮二异氰酸酯在1小时内滴加到反应容器中。起初将几滴二月桂酸二丁基锡作为催化剂加入。在所述的一小时后将反应温度升高到120℃,使得反应再继续进行2小时,然后将获得的预聚物脱气,冷却并回收。
获得了具有如下特征的无色的蜡质物:
玻璃化转变温度(Tg),℃ 0
分子量(Mn) 1603
异氰酸酯含量,% 5.33
实施例2
将30g由实施例1获得的预聚物加热到120℃并脱气以除去所有空气。此时将化学计量数量的1,4-丁二醇加入到预聚物用于与可利用的游离异氰酸酯基团反应。将获得的聚氨酯弹性体随后在122℃下固化24小时。
实施例3
将30g由实施例1获得的预聚物加热到120℃并脱气以除去所有空气。此时将化学计量数量的1,4-丁二醇和三羟甲基丙烷(按重量1∶1)的混合物加入到预聚物用于与可利用的游离异氰酸酯基团。将获得的聚氨酯弹性体随后在122℃下固化24小时。
实施例4
将30g由实施例1获得的预聚物加热到120℃并脱气以除去所有空气。此时将化学计量数量的每分子有3个氧化乙烯单元的多乙氧基化三羟甲基丙烷(Polyol 3610TM,Perstorp Specialty Chemicals AB,Sweden)加入到预聚物用于与可利用的游离异氰酸酯基团反应。将获得的聚氨酯弹性体随后在122℃下固化24小时。
实施例5(对照)
重复实施例1,区别在于使用分子量为1000的已二酸乙二醇酯代替所述2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇。
实施例6(对照)
重复实施例2,区别在于使用实施例5的预聚物代替实施例1的预聚物。
实施例7(对照)
重复实施例3,区别在于使用实施例5的预聚物代替实施例1的预聚物。
实施例8
使用“斑点试验”或“表面玻璃(watch glass)”方法评价实施例2-4和5-7(对照)中制备的弹性体的耐化学品性。所用的化学品为丙酮、液压泵油、50%硫酸水溶液和50%氢氧化钠水溶液。12、24、36、48和60小时之后从视觉上评价损坏如溶胀、褪色和/或开裂并以级别0-3分等级,其中0=无可见的损坏,1=轻微的可见损坏,2=明显的可见损坏和3=严重损坏。结果列于如下表1中。
实施例9
在实施例2-4和5-7(对照)中制备的弹性体上进行肖氏硬度计硬度试验。根据本发明的弹性体(实施例2-4)均比相应的基于聚酯的弹性体(对照)更坚硬。肖氏A值列于如下表2中。
实施例10
实施例2-4和5-7(对照)中制备的弹性体的热性质、玻璃化转变温度(Tg)用DSC以10℃/min测量。根据本发明的弹性体(实施例2-4)均显示出对应的基于聚酯弹性体(对照)较高的Tg。Tg值列于如下表3中。
实施例11
将181.99g的1,6-六亚甲基二异氰酸酯与作为催化剂的几滴二月桂酸二丁基锡进料到装有温度计、搅拌器、真空装置、加热装置、冷却装置和氮气吹扫装置的反应器中并加热到60℃。其后将温度升高到70℃并开始滴加542.01g分子量为1000的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯(OxymerTM B112,Perstorp Specialty Chemicals AB,瑞典)。当所有聚碳酸酯二醇进料一小时后,将反应温度升高到80℃,使得反应再继续进行2小时。将得到的预聚物最终脱气,回收并冷却。
获得具有如下特征的无色蜡质物:
玻璃化转变温度(Tg),℃ -22
分子量(Mn) 2200
异氰酸酯含量,% 5.0
实施例12(对照)
重复实施例11,区别在于使用1,6-己二醇聚碳酸酯(DesmophenTM XP 2586,Bayer MaterialScience,德国)代替所述的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇。
实施例13(对照)
重复实施例11,区别在于使用己二酸-乙二醇共聚物(FomrezTM 22-112,Crompton Uniroyal Chemical,英国)代替所述的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇。
实施例14(对照)
重复实施例11,区别在于使用聚(四亚甲基醚)二醇(TerathaneTM1000,Invista,美国)代替所述的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇。
实施例15(对照)
重复实施例11,区别在于使用线型聚酯己内酯(CapaTM 2101A,Solvay,比利时)代替所述的2-丁基-2-乙基-1,3-丙二醇聚碳酸酯二醇。
实施例16
将180g实施例11中获得的预聚物加热到90℃并脱气除去所有的空气。此时将化学计量数量的1,4-丁二醇加入预聚物中以进行与可利用的游离异氰酸酯基团的反应。将反应混合物在浇注入模具前进行二次脱气。接着将获得的聚氨酯弹性体在120℃下固化24小时。之后将模制产品从模具中移出并在23℃下和50%的相对湿度下后固化一周。
以相同的方式由对照实施例12-15获得的预聚物制备对照材料。
获得的聚氨酯弹性体具有如下尺寸:245×160×4mm。
实施例17
将实施例16中获得的各个弹性体的三个不同样品进行切割(切割模头类型(Cutting Die Type)ISO 37-2)以进行拉伸试验。样品的硬度以肖氏A硬度计测量,结果在下表4中给出。
实施例18
将实施例16中获得的各个弹性体的三个样品进行切割(切割模头类型(Cutting Die Type)ISO 37-2)以进行抗水解试验。将试样在70℃和95%的相对湿度下在气候试验箱中老化14天。该试验后以肖氏A硬度计测量样品的硬度,将样品硬度与表4中给出的初始值比较。
占所述原始值的百分比的结果在下表5中给出。
实施例19
将实施例16中获得的各个弹性体的三个样品进行切割(切割模头类型(Cutting Die Type)ISO 37-2)以进行耐候试验。耐候性用加速QUV试验按照如下方案模拟:QUV-A:在60℃下4小时UV,在50℃下凝固(condensation)4小时,总运行时间为1000小时。保留的机械性能以肖氏A硬度计和拉伸试验机测定并与表4中给出的初始值比较。
由对照实施例14中获得的弹性体切出的所有样品均不能经受QUV,因此不能随后进行测试。只有一个由实施例15获得弹性体切出的样品和只有两个从由对照实施例13获得的弹性体切出的两个样品能在老化后进行试验。
占所述原始值的百分比的结果在下表6中给出。
表1
按照实施例2的弹性体 暴露(小时)
12 24 36 48 60
丙酮 1 3 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 0 0 0 1 1
氢氧化钠50% 0 0 0 0 0
按照实施例3的弹性体 暴露(小时)
12 24 36 48 60
丙酮 2 3 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 0 0 0 1 1
氢氧化钠50% 0 0 0 0 0
按照实施例4的弹性体 暴露(小时)
12 24 36 48 60
丙酮 0 2 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 0 0 0 0 0
氢氧化钠50% 0 0 0 0 0
按照实施例5(对照)的弹性体 暴露(小时)
12 24 36 48 60
丙酮 1 3 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 1 2 3 3 3
氢氧化钠50% 0 0 1 2 2
按照实施例6(对照)的弹性体 暴露(小时)
12 24 36 48 60
丙酮 1 3 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 1 2 3 3 3
氢氧化钠50% 0 0 2 2 2
按照实施例7(对照)的弹性体 暴露(小时)
12 24 36 48 60
丙酮 1 3 3 3 3
液压泵油 0 0 0 0 0
硫酸50% 1 2 3 3 3
氢氧化钠50% 0 0 2 2 3
表2
样品 肖氏A
按照实施例2的弹性体 56±9
按照实施例3的弹性体 91±3
按照实施例4的弹性体 91±5
按照实施例5(对照)的弹性体 46±6
按照实施例6(对照)的弹性体 61±1
按照实施例7(对照)的弹性体 62±5
表3
样品 Tg,℃
按照实施例2的弹性体 14
按照实施例3的弹性体 16
按照实施例4的弹性体 15
按照实施例5(对照)的弹性体 -20
按照实施例6(对照)的弹性体 -18
按照实施例7(对照)的弹性体 -23
表4
弹性体依据的实施例 | 肖氏A硬度 | E-模量MPa | 10%应变下的应力,% | 最大应力MPa | 伸长率% |
11 | 52±4 | 1.5±0.1 | 0.1±0.0 | 3.3±0.8 | 600±60 |
12(对照) | 91±1 | 38±2 | 2.6±0.2 | 27±2 | 800±40 |
13(对照) | 93±1 | 43±1 | 2.3±0.0 | 27±7 | 1300±300 |
14(对照) | 92±1 | 46±1 | 2.7±0.1 | 14±2 | 800±150 |
15(对照) | 94±0 | 49±1 | 2.8±0.1 | 16±1 | 800±90 |
表5
弹性体依据的实施例 | 硬度% | E-模量% | 最大应力% | 伸长率% | 重量% |
11 | -8.8 | 5.8 | -33 | 29 | -5.4 |
12(对照) | -5.9 | 5 | 29 | 33 | 0.8 |
13(对照) | -1.5 | -42 | -80 | -95 | 2.3 |
14(对照) | -1.3 | -25 | 12 | 20 | 1.2 |
15(对照) | -1.6 | -23 | -18 | 5 | 1.4 |
表6
弹性体依据的实施例 | 硬度% | E-模量% | 最大应力% | 伸长率% | 重量% |
11 | -16.9 | 7.5 | -75.6 | -74.3 | -7.4 |
12(对照) | -5.6 | -37.0 | -78.0 | -70.0 | -0.5 |
13(对照) | -10.0 | -65.0 | -94.0 | -98.0 | -0.3 |
14(对照) | - | - | - | - | - |
15(对照) | -12.0 | -69.0 | -98.0 | -98.0 | -0.1 |
Claims (11)
1、一种聚氨酯弹性体,通过将至少二、三或多异氰酸酯、聚碳酸酯二醇和二、三或多元醇反应获得,特征在于所述的聚碳酸酯二醇是2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、烷氧基化2-烷基-1,3-丙二醇和/或烷氧基化2,2-二烷基-1,3-丙二醇的至少一种聚碳酸酯二醇和/或是包含来自两个或多个所述1,3-丙二醇的单元的至少一种聚碳酸酯二醇,其中烷基是具有1-8个碳原子的线性或支化的脂肪族烷烃基,烷氧基化是具有1-20烷氧基单元的乙氧基化、丙氧基化和/或丁氧基化。
2、根据权利要求1的聚氨酯弹性体,特征在于所述的聚碳酸酯二醇是2-甲基-1,3-丙二醇、2-甲基-2-乙基-1,3-丙二醇、2-乙基-2-丁基-1,3-丙二醇、2,2-二甲基-1,3-丙二醇的至少一种聚碳酸酯二醇和/或是至少一种包含来自两个或多个所述1,3-丙二醇的单元的聚碳酸酯二醇。
3、根据权利要求1或2的聚氨酯弹性体,特征在于所述的聚碳酸酯二醇由一种或多种所述的1,3-丙二醇和二氧化碳源,如碳酸二甲酯、碳酸二乙酯和/或脲获得。
4、根据权利要求1-3中任一项的聚氨酯弹性体,特征在于所述的聚碳酸酯二醇的分子量为500-5000,如500-2500。
5、根据权利要求1-4中任一项的聚氨酯弹性体,特征在于所述的二或多异氰酸酯为脂族、环脂族和/或芳香族的二、三或多异氰酸酯。
6、根据权利要求1-5中任一项的聚氨酯弹性体,特征在于所述的二或多异氰酸酯为六亚甲基二异氰酸酯、2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、四甲基二甲苯二异氰酸酯、1,6-己烷二异氰酸酯、三甲基己烷二异氰酸酯、1,12-十二烷二异氰酸酯、环己烷二异氰酸酯、二苯基甲烷二异氰酸酯、异佛尔酮二异氰酸酯和/或壬烷三异氰酸酯。
7、根据权利要求1-6中任一项的聚氨酯弹性体,特征在于所述的二、三或多元醇为至少一种1,ω-二元醇、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、2-烷基-2-羟烷基-1,3-丙二醇和/或2,2-二(羟烷基)-1,3-丙二醇和/或所述二、三或多元醇的至少一种二聚物、三聚物或聚合物。
8、根据权利要求1-6中任一项的聚氨酯弹性体,特征在于所述的二、三或多元醇为至少一种氧化烯与至少一种1,ω-二元醇、2-烷基-1,3-丙二醇、2,2-二烷基-1,3-丙二醇、2-烷基-2-羟烷基-1,3-丙二醇和/或2,2-二(羟烷基)-1,3-丙二醇和/或所述二、三或多元醇的至少一种二聚物、三聚物或聚合物间的反应产物。
9、根据权利要求8的聚氨酯弹性体,特征在于所述的氧化烯为环氧乙烷、环氧丙烷、1,3-环氧丁烷、2,4-环氧丁烷、氧化环己烯、一氧化丁二烯和/或氧化苯乙烯。
10、根据权利要求1-6中任一项的聚氨酯弹性体,特征在于所述的二、三或多元醇为1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,6-环己烷二甲醇、5,5-二羟基甲基-1,3-二氧六环、2-甲基-1,3-丙二醇、2-甲基-2-乙基-1,3丙二醇、2-乙基-2-丁基-1,3-丙二醇、新戊二醇、二羟甲基丙烷、1,1-二羟甲基环己烷、甘油、三羟甲基乙烷、三羟甲基丙烷、一缩二甘油、双三羟甲基乙烷、双三羟甲基丙烷、季戊四醇、双季戊四醇、脱水壬七醇、山梨糖醇和/或甘露醇。
11、根据权利要求1-6中任一项的聚氨酯弹性体,特征在于所述的二、三或多元醇为乙氧基化和/或丙氧基化的甘油、三羟甲基乙烷、三羟甲基丙烷、一缩二甘油、双三羟甲基乙烷、双三羟甲基丙烷、季戊四醇、双季戊四醇、脱水壬七醇、山梨糖醇和/或甘露醇。
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- 2006-10-10 CN CNA2006800380593A patent/CN101287773A/zh active Pending
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CN108602946B (zh) * | 2016-02-09 | 2020-07-07 | 宇部兴产株式会社 | 聚碳酸酯多元醇 |
CN106519159A (zh) * | 2016-10-27 | 2017-03-22 | 江西科技师范大学 | 高耐水性、耐甲苯性柠檬烯基聚氨酯及其制备方法 |
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WO2007043945A1 (en) | 2007-04-19 |
KR20080057276A (ko) | 2008-06-24 |
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EP1934272A1 (en) | 2008-06-25 |
CA2624759A1 (en) | 2007-04-19 |
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