TWI228515B - Glass fibre sizes comprising self-crosslinking polyurethane, polyurethane-polyurea or polyurea dispersions - Google Patents
Glass fibre sizes comprising self-crosslinking polyurethane, polyurethane-polyurea or polyurea dispersions Download PDFInfo
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- TWI228515B TWI228515B TW089105876A TW89105876A TWI228515B TW I228515 B TWI228515 B TW I228515B TW 089105876 A TW089105876 A TW 089105876A TW 89105876 A TW89105876 A TW 89105876A TW I228515 B TWI228515 B TW I228515B
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- Prior art keywords
- component
- reactive
- dispersion
- isocyanate
- weight percent
- Prior art date
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- 239000006185 dispersion Substances 0.000 title claims abstract description 119
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 35
- 238000004132 cross linking Methods 0.000 title claims abstract description 19
- 239000004814 polyurethane Substances 0.000 title claims abstract description 10
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 9
- 239000003365 glass fiber Substances 0.000 title claims description 28
- 125000000524 functional group Chemical group 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 239000002002 slurry Substances 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 27
- 238000011049 filling Methods 0.000 claims description 26
- 239000012948 isocyanate Substances 0.000 claims description 26
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 26
- 150000004985 diamines Chemical class 0.000 claims description 24
- 150000002513 isocyanates Chemical class 0.000 claims description 24
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 229920000570 polyether Polymers 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229920000768 polyamine Polymers 0.000 claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 239000003223 protective agent Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 150000002009 diols Chemical class 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000004615 ingredient Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 2
- PHEXXGCUKSJMBJ-UHFFFAOYSA-N [O].[SiH4] Chemical class [O].[SiH4] PHEXXGCUKSJMBJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001449 anionic compounds Chemical class 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229920000909 polytetrahydrofuran Polymers 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- -1 isocyanate salt Chemical class 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 229920006170 Therban® Polymers 0.000 description 10
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 150000003335 secondary amines Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000015170 shellfish Nutrition 0.000 description 5
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 3
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- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 150000008040 ionic compounds Chemical class 0.000 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 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- 238000005728 strengthening Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
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- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- SWDDLRSGGCWDPH-UHFFFAOYSA-N 4-triethoxysilylbutan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCCN SWDDLRSGGCWDPH-UHFFFAOYSA-N 0.000 description 2
- RBVMDQYCJXEJCJ-UHFFFAOYSA-N 4-trimethoxysilylbutan-1-amine Chemical compound CO[Si](OC)(OC)CCCCN RBVMDQYCJXEJCJ-UHFFFAOYSA-N 0.000 description 2
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- 230000008859 change Effects 0.000 description 2
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
- C08G18/08—Processes
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- 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
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
- C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
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Landscapes
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- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
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- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI799553B (zh) * | 2018-03-27 | 2023-04-21 | 美商艾德凡斯化學公司 | 觸變型流變性改質劑組合物 |
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| DE10147546B4 (de) * | 2001-09-26 | 2006-04-13 | Basf Coatings Ag | Polyurethan, Verfahren zu seiner Herstellung und seine Verwendung |
| DE10216945A1 (de) | 2002-04-17 | 2003-11-06 | Bayer Ag | Selbstvernetzende PUR-Dispersionen |
| DE10226933A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Glasfaserverstärkte Kunststoffe |
| DE10306243A1 (de) * | 2003-02-14 | 2004-08-26 | Bayer Ag | Einkomponenten-Beschichtungssysteme |
| US6989429B2 (en) * | 2003-10-02 | 2006-01-24 | Tremco Incorporated | Prepolymer compositions and sealants made therefrom |
| CN2689322Y (zh) * | 2004-02-28 | 2005-03-30 | 鸿富锦精密工业（深圳）有限公司 | 主机板固定装置 |
| US20070072989A1 (en) * | 2004-03-19 | 2007-03-29 | Piret Willy H | Two-part sizing composition for reinforcement fibers |
| US20050228121A1 (en) * | 2004-04-01 | 2005-10-13 | Ziegler Michael J | Oligomer suitable for coating compositions for wood substrates |
| WO2006047746A1 (en) * | 2004-10-26 | 2006-05-04 | Noveon, Inc. | Water-borne dispersions of oil modified urethane polymers |
| US7240371B2 (en) | 2005-02-11 | 2007-07-10 | Invista North America S.A.R.L. | Solvent free aqueous polyurethane dispersions and adhesive films therefrom for stretch fabrics |
| US20080004395A1 (en) * | 2005-02-11 | 2008-01-03 | Invista North America S.A.R.L. | Aqueous polyurethaneurea compositions including dispersions and films |
| US20060183850A1 (en) * | 2005-02-11 | 2006-08-17 | Invista North America S.A.R.L. | Solvent free aqueous polyurethane dispersions and shaped articles therefrom |
| ATE430771T1 (de) | 2005-03-24 | 2009-05-15 | Medtronic Inc | Modifizierung von thermoplastischen polymeren |
| DE102005018692A1 (de) * | 2005-04-22 | 2006-10-26 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| US20070256789A1 (en) * | 2005-06-24 | 2007-11-08 | Invista North Americal S.A.R.L. | Guide for bonding tapes or films |
| US8389653B2 (en) * | 2006-03-30 | 2013-03-05 | Basf Corporation | Method of catalyzing a reaction to form a urethane coating and a complex for use in the method |
| DE102006025313A1 (de) * | 2006-05-31 | 2007-12-06 | Bayer Materialscience Ag | Lösemittelarme oder lösemittelfreie Vernetzer-Dispersion mit Pyrazol-blockierten Isocyanatgruppen |
| JP4797843B2 (ja) * | 2006-07-11 | 2011-10-19 | コニカミノルタエムジー株式会社 | 圧電性合成樹脂膜の形成方法 |
| DE102006052240A1 (de) * | 2006-11-03 | 2008-05-08 | Bayer Materialscience Ag | Lösungen blockierter Polyimide bzw. Polyamidimide |
| KR100860009B1 (ko) * | 2006-12-13 | 2008-09-25 | (주)아텍스 | 고부착력의 폴리우레아 코팅제의 제조방법 및 폴리우레아의 코팅방법 |
| DE102006059680A1 (de) * | 2006-12-18 | 2008-06-19 | Bayer Materialscience Ag | Colöserfreie, selbstvernetzende PUR-Dispersionen |
| US20080160281A1 (en) * | 2006-12-29 | 2008-07-03 | Vickery Eric L | Sizing composition for glass fibers |
| DE102007023319A1 (de) * | 2007-05-16 | 2008-11-20 | Bayer Materialscience Ag | Aufgesäuerte Polyesterpolyurethan-Dispersion |
| CL2008003124A1 (es) * | 2007-11-07 | 2009-11-27 | Bayer Materialscience Ag | Dispersiones acuosas de poliuretano-urea acuosa de; poliol(es) difuncional (es) o funcionalidad superior, compuestos(s) monofuncional (es) con la menos 50% p/p de óxido de etileno, componente(s)di o poliiocianato; y mezcla de compuestos monoamina primarios y/o secundarios; procedimiento; uso; composición; y compuesto adhesivo. |
| DE102007054002A1 (de) * | 2007-11-13 | 2009-05-14 | Bayer Materialscience Ag | Nicht-ionisch hydrophilierte Bindemittel-Dispersionen |
| EP2103316A1 (de) | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Hydrophile Polyurethandispersionen |
| EP2103638A1 (de) * | 2008-03-20 | 2009-09-23 | Bayer MaterialScience AG | Hydrophile Polyurethanlösungen |
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| DE102008025613A1 (de) | 2008-05-28 | 2009-12-03 | Bayer Materialscience Ag | Hydrophile Polyurethanbeschichtungen |
| NZ587326A (en) * | 2008-05-28 | 2012-07-27 | Clariant Finance Bvi Ltd | Aqueous polyurethane-polyurea dispersions |
| DE102008025614A1 (de) * | 2008-05-28 | 2009-12-03 | Bayer Materialscience Ag | Hydrophile Polyurethanbeschichtungen |
| US8791200B2 (en) | 2008-09-04 | 2014-07-29 | Bayer Materialscience Ag | TCD based hydrophilic polyurethane dispersions |
| DK2331596T3 (da) * | 2008-09-04 | 2012-05-29 | Bayer Materialscience Ag | TCD baserede hyddrofile polyurethadispersioner |
| MX2011003996A (es) * | 2008-10-17 | 2011-05-10 | Invista Tech Sarl | Composiciones acuosas de poliuretanourea que incluyen dispersiones y peliculas. |
| EP2186841A1 (de) * | 2008-11-14 | 2010-05-19 | Bayer MaterialScience AG | Vernetzbare Polyurethan-Dispersionen |
| EP2221330A1 (de) | 2009-02-19 | 2010-08-25 | Bayer MaterialScience AG | Funktionalisierte Polyurethanpolyharnstoff-Dispersionen |
| EP2298825A1 (de) | 2009-09-17 | 2011-03-23 | Bayer MaterialScience AG | Hydrophile Polyurethanharnstoffdispersionen |
| US9617453B2 (en) | 2009-12-14 | 2017-04-11 | Air Products And Chemicals, Inc. | Solvent free aqueous polyurethane dispersions and methods of making and using the same |
| KR101225580B1 (ko) * | 2010-07-19 | 2013-01-24 | 애경화학 주식회사 | 사이즈제용 수성 폴리우레탄 분산액 및 그 제조방법, 및 이를 포함하는 유리섬유 사이즈제 |
| JP6106515B2 (ja) * | 2012-05-09 | 2017-04-05 | 第一工業製薬株式会社 | ガラス繊維用集束剤 |
| US9587139B2 (en) | 2012-06-15 | 2017-03-07 | 3M Innovative Properties Company | Curable polyurea forming composition, method of making, and composite article |
| US10907005B2 (en) * | 2012-09-25 | 2021-02-02 | Battelle Memorial Institute | Aqueous prepolymer dispersions |
| KR101368339B1 (ko) | 2013-07-26 | 2014-02-28 | 설태윤 | 작업성 및 설비조작성이 우수한 신발갑피용 1액형 폴리우레아 수지 조성물 |
| CN103696321A (zh) * | 2013-12-20 | 2014-04-02 | 天津商业大学 | 一种复合表面施胶剂的制备方法 |
| US10793672B2 (en) | 2014-06-11 | 2020-10-06 | Battelle Memorial Institute | Alkoxylated bio-oil polyol compositions |
| RU2690360C2 (ru) * | 2014-09-19 | 2019-05-31 | Санио Кемикал Индастриз, Лтд. | Композиция проклеивающего средства для волокна, дисперсия проклеивающего средства для волокна, раствор проклеивающего средства для волокна, способ для производства пучков волокон, композитный промежуточный материал и армированный волокном композиционный материал |
| US10836927B2 (en) * | 2014-12-09 | 2020-11-17 | Basf Coatings Gmbh | Aqueous polyurethane-polyurea dispersion and aqueous base paint containing said dispersion |
| CN105968285A (zh) * | 2016-06-02 | 2016-09-28 | 深圳市深赛尔股份有限公司 | 一种水性硅烷聚脲树脂及其制备方法 |
| EP3500609B1 (en) | 2016-08-17 | 2020-12-30 | The LYCRA Company UK Limited | Aqueous polyurethane dispersions, prepolymers, and shaped articles made therefrom |
| CN109134804B (zh) * | 2016-12-19 | 2021-10-22 | 科思创德国股份有限公司 | 聚氨酯水性分散体 |
| CN107267050A (zh) * | 2017-07-27 | 2017-10-20 | 上海展辰涂料有限公司 | 一种水性木器双组分亮光调色浅色面漆的发明 |
| WO2019089516A1 (en) | 2017-11-03 | 2019-05-09 | A&At Llc | Methods for use of aqueous polyurethane dispersions and articles made thereby |
| CN107936212B (zh) * | 2017-11-29 | 2020-12-18 | 广州冠志新材料科技有限公司 | 指甲油用水性聚氨酯树脂及其制备方法 |
| US12441918B2 (en) * | 2019-09-27 | 2025-10-14 | Lg Chem, Ltd. | Adhesive composition, and polarizing plate and display device manufactured using same |
| CN113718534B (zh) * | 2020-05-25 | 2023-09-15 | 中国石油化工股份有限公司 | 一种防爆抗冲击纤维增强聚脲复合材料及其制备方法和应用 |
| WO2022107811A1 (en) * | 2020-11-19 | 2022-05-27 | Japan Fine Coatings Co., Ltd. | Composition for forming coating layer of optical fiber and cured layer thereof, optical fiber having cured layer, and use thereof |
| JP7716208B2 (ja) * | 2020-11-19 | 2025-07-31 | 日本特殊コーティング株式会社 | 光ファイバ被覆層形成用組成物及びその硬化層、並びに硬化層を有する光ファイバ及び光ファイバ被覆層形成用組成物の使用 |
| CN116601201A (zh) | 2020-12-08 | 2023-08-15 | 科思创德国股份有限公司 | 水性聚氨酯脲分散体 |
| EP4029894A1 (en) | 2021-01-15 | 2022-07-20 | Covestro Deutschland AG | Aqueous polyurethane urea dispersion |
| EP4112670A1 (de) * | 2021-07-01 | 2023-01-04 | Covestro Deutschland AG | Nicht-ionisch hydrophilierte polyurethan-dispersionen mit acrylat-doppelbindungen |
| EP4112669A1 (de) * | 2021-07-01 | 2023-01-04 | Covestro Deutschland AG | Nicht-ionisch hydrophilierte polyurethan-dispersionen mit methacrylat-doppelbindungen |
| WO2025108924A1 (en) * | 2023-11-21 | 2025-05-30 | Covestro Deutschland Ag | Water-dispersible blocked isocyanate prepolymer system, method for preparing the same, and application thereof |
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| US4108814A (en) | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
| DE2553839C3 (de) * | 1975-05-22 | 1978-11-23 | Bayer Ag, 5090 Leverkusen | Beschlichtete Glasfasern |
| US4255317A (en) | 1978-11-20 | 1981-03-10 | Owens-Corning Fiberglas Corporation | Non-discoloring glass strand size |
| US4310646A (en) * | 1979-04-09 | 1982-01-12 | Basf Aktiengesellschaft | Self-crosslinking cationic binders and their preparation |
| DE3015143A1 (de) * | 1979-04-30 | 1980-11-06 | Grace W R & Co | Polyurethanpolymere in waessrigem medium und verfahren zu deren herstellung |
| US4387181A (en) | 1980-04-09 | 1983-06-07 | Textron, Inc. | Polymer compositions and manufacture |
| DE3641494A1 (de) * | 1986-12-04 | 1988-06-09 | Bayer Ag | In wasser loesliche oder dispergierbare poylurethane, ein verfahren zu ihrer herstellung und ihre verwendung zur beschichtung beliebiger substrate |
| JPH04325510A (ja) * | 1991-04-26 | 1992-11-13 | Dainippon Ink & Chem Inc | 接着剤 |
| CA2072931C (en) | 1991-07-23 | 2003-12-30 | Robin E. Tirpak | A process for the preparation of aqueous dispersions containing both blocked polyisocyanates and polyhydroxyl compounds |
| DE4142734A1 (de) † | 1991-12-21 | 1993-06-24 | Hoechst Ag | Wasserverduennbares, urethanmodifiziertes und hydroxylgruppen enthaltendes selbstvernetzendes bindemittel und zubereitungen davon |
| DE4218184A1 (de) | 1992-06-02 | 1993-12-09 | Bayer Ag | Wäßriges Bindemittelgemisch und seine Verwendung |
| JP3205786B2 (ja) * | 1992-08-18 | 2001-09-04 | 関西ペイント株式会社 | 自己架橋性樹脂 |
| US5574083A (en) * | 1993-06-11 | 1996-11-12 | Rohm And Haas Company | Aromatic polycarbodiimide crosslinkers |
| DE19548030A1 (de) * | 1995-12-21 | 1997-06-26 | Bayer Ag | Verwendung wässriger Dispersionen nachvernetzbarer Beschichtungsmittel zur Textil- und Lederbeschichtung |
| EP0792899B1 (de) † | 1996-03-01 | 2003-05-02 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyurethanharnstoffe, ein Verfahren zu deren Herstellung und ihre Verwendung zur Beschichtung beliebiger Substrate |
| DE19611850A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Verwendung von ionischen und nichtionischen wäßrigen Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan als Bindemittel für Glasfaserschlichten sowie spezielle ionische und nichtionische wäßrige Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan |
| JP3783283B2 (ja) * | 1996-05-14 | 2006-06-07 | 日東紡績株式会社 | ガラス繊維用集束剤 |
| WO1998002494A1 (fr) * | 1996-07-12 | 1998-01-22 | Kansai Paint Company, Limited | Composition d'electrodeposition cationique de revetement |
| DE19822631A1 (de) † | 1998-05-20 | 1999-11-25 | Basf Coatings Ag | Beschichtungsmittel, die geblockte Polyurethanprepolymere enthalten, und deren Verwendung |
| JP2002506414A (ja) * | 1998-06-04 | 2002-02-26 | オウェンス コーニング コンポジッツ エスピーアールエル | 繊維用の高溶解度サイズ剤組成物 |
-
1999
- 1999-04-01 DE DE19914882A patent/DE19914882A1/de not_active Withdrawn
-
2000
- 2000-03-21 WO PCT/EP2000/002486 patent/WO2000059973A1/de not_active Ceased
- 2000-03-21 US US09/937,835 patent/US6586523B1/en not_active Expired - Lifetime
- 2000-03-21 EP EP00918820A patent/EP1169369B2/de not_active Expired - Lifetime
- 2000-03-21 AT AT00918820T patent/ATE252117T1/de not_active IP Right Cessation
- 2000-03-21 HK HK02107369.6A patent/HK1045702A1/zh unknown
- 2000-03-21 CZ CZ20013530A patent/CZ20013530A3/cs unknown
- 2000-03-21 JP JP2000609478A patent/JP4740460B2/ja not_active Expired - Fee Related
- 2000-03-21 TR TR2001/02774T patent/TR200102774T2/xx unknown
- 2000-03-21 RU RU2001129498/04A patent/RU2252942C2/ru not_active IP Right Cessation
- 2000-03-21 BR BR0009500-1A patent/BR0009500A/pt not_active IP Right Cessation
- 2000-03-21 KR KR1020017012405A patent/KR100642177B1/ko not_active Expired - Fee Related
- 2000-03-21 UA UA2001107428A patent/UA73734C2/uk unknown
- 2000-03-21 ES ES00918820T patent/ES2208302T5/es not_active Expired - Lifetime
- 2000-03-21 DE DE50004081T patent/DE50004081D1/de not_active Expired - Lifetime
- 2000-03-21 AU AU39632/00A patent/AU3963200A/en not_active Abandoned
- 2000-03-21 PL PL00350997A patent/PL350997A1/xx not_active Application Discontinuation
- 2000-03-21 CA CA002364603A patent/CA2364603C/en not_active Expired - Fee Related
- 2000-03-21 CN CN00805504A patent/CN1345344A/zh active Pending
- 2000-03-21 MX MXPA01009822A patent/MXPA01009822A/es unknown
- 2000-03-30 TW TW089105876A patent/TWI228515B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI799553B (zh) * | 2018-03-27 | 2023-04-21 | 美商艾德凡斯化學公司 | 觸變型流變性改質劑組合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1169369A1 (de) | 2002-01-09 |
| EP1169369B2 (de) | 2006-05-17 |
| PL350997A1 (en) | 2003-02-24 |
| JP2002541280A (ja) | 2002-12-03 |
| CZ20013530A3 (cs) | 2002-01-16 |
| UA73734C2 (en) | 2005-09-15 |
| KR20020027303A (ko) | 2002-04-13 |
| ES2208302T5 (es) | 2007-02-01 |
| CA2364603C (en) | 2009-12-22 |
| JP4740460B2 (ja) | 2011-08-03 |
| US6586523B1 (en) | 2003-07-01 |
| ES2208302T3 (es) | 2004-06-16 |
| WO2000059973A1 (de) | 2000-10-12 |
| BR0009500A (pt) | 2002-01-15 |
| DE50004081D1 (de) | 2003-11-20 |
| CA2364603A1 (en) | 2000-10-12 |
| CN1345344A (zh) | 2002-04-17 |
| KR100642177B1 (ko) | 2006-11-10 |
| MXPA01009822A (es) | 2002-06-21 |
| RU2252942C2 (ru) | 2005-05-27 |
| ATE252117T1 (de) | 2003-11-15 |
| HK1045702A1 (zh) | 2002-12-06 |
| DE19914882A1 (de) | 2000-10-05 |
| EP1169369B1 (de) | 2003-10-15 |
| AU3963200A (en) | 2000-10-23 |
| TR200102774T2 (tr) | 2002-04-22 |
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