TWI262197B - Stabilized aqueous polyurethane-polyurea dispersions - Google Patents
Stabilized aqueous polyurethane-polyurea dispersions Download PDFInfo
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- TWI262197B TWI262197B TW092100832A TW92100832A TWI262197B TW I262197 B TWI262197 B TW I262197B TW 092100832 A TW092100832 A TW 092100832A TW 92100832 A TW92100832 A TW 92100832A TW I262197 B TWI262197 B TW I262197B
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- 239000006185 dispersion Substances 0.000 title claims abstract description 41
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 239000011230 binding agent Substances 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000003365 glass fiber Substances 0.000 claims abstract description 17
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 239000003381 stabilizer Substances 0.000 claims abstract description 15
- 238000004513 sizing Methods 0.000 claims abstract description 13
- 239000000853 adhesive Substances 0.000 claims abstract description 9
- 230000001070 adhesive effect Effects 0.000 claims abstract description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 239000000123 paper Substances 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003010 ionic group Chemical group 0.000 claims description 6
- 229920000768 polyamine Polymers 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 3
- 230000002079 cooperative effect Effects 0.000 claims description 3
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229940125773 compound 10 Drugs 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 21
- 239000011248 coating agent Substances 0.000 abstract description 15
- 229920000642 polymer Polymers 0.000 abstract description 10
- 229920003009 polyurethane dispersion Polymers 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000000087 stabilizing effect Effects 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- -1 tetramethylpiperidine free radical Chemical class 0.000 description 32
- 239000004814 polyurethane Substances 0.000 description 16
- 238000007639 printing Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229920000570 polyether Polymers 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
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- 229920000728 polyester Polymers 0.000 description 7
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- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 229920000058 polyacrylate Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical class O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 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 description 3
- 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 3
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Chemical class 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
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- 239000000052 vinegar Substances 0.000 description 3
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- IVGRSQBDVIJNDA-UHFFFAOYSA-N 2-(2-aminoethylamino)ethanesulfonic acid Chemical compound NCCNCCS(O)(=O)=O IVGRSQBDVIJNDA-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 2
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- 125000000129 anionic group Chemical group 0.000 description 2
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- UPWMGWGRISYZOA-UHFFFAOYSA-N barium;hexanedioic acid Chemical compound [Ba].OC(=O)CCCCC(O)=O UPWMGWGRISYZOA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine
-
- 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
- C08G18/28—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
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3834—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing hydrazide or semi-carbazide 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
- C08G18/28—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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2991—Coated
- Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
- Y10T428/2996—Glass particles or spheres
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
- Y10T428/31601—Quartz or glass
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002101546 DE10201546A1 (de) | 2002-01-17 | 2002-01-17 | Stabilisierte wässrige Polyurethan-Polyharnstoff Dispersionen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200307027A TW200307027A (en) | 2003-12-01 |
| TWI262197B true TWI262197B (en) | 2006-09-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092100832A TWI262197B (en) | 2002-01-17 | 2003-01-16 | Stabilized aqueous polyurethane-polyurea dispersions |
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| US (1) | US7091280B2 (enExample) |
| EP (1) | EP1474487B1 (enExample) |
| JP (1) | JP4494790B2 (enExample) |
| KR (1) | KR20040083087A (enExample) |
| CN (1) | CN1290892C (enExample) |
| AT (1) | ATE319758T1 (enExample) |
| AU (1) | AU2003206707A1 (enExample) |
| BR (1) | BR0302715A (enExample) |
| CA (1) | CA2473411C (enExample) |
| DE (2) | DE10201546A1 (enExample) |
| DK (1) | DK1474487T3 (enExample) |
| ES (1) | ES2260606T3 (enExample) |
| HK (1) | HK1080094B (enExample) |
| MX (1) | MXPA04006844A (enExample) |
| RU (1) | RU2004125181A (enExample) |
| TW (1) | TWI262197B (enExample) |
| WO (1) | WO2003060017A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004002527A1 (de) * | 2004-01-16 | 2005-08-04 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| DE102004002526A1 (de) * | 2004-01-16 | 2005-08-04 | Bayer Materialscience Ag | Thermovergilbungsstabile Polyurethan-Polyharnstoff Dispersionen |
| DE102004002525A1 (de) * | 2004-01-16 | 2005-08-04 | Bayer Materialscience Ag | Beschichtungsmittelzusammensetzung |
| JP4293441B2 (ja) * | 2004-05-14 | 2009-07-08 | 第一工業製薬株式会社 | 耐熱性人工・合成皮革用水系ポリウレタン樹脂組成物及びその製造方法並びに皮革様シート。 |
| DE102004060139A1 (de) * | 2004-12-13 | 2006-06-29 | Bayer Materialscience Ag | Festkörperreiche Polyurethanpolyharnstoff-Dispersionen |
| DE102005018692A1 (de) * | 2005-04-22 | 2006-10-26 | Bayer Materialscience Ag | Schlichtezusammensetzung |
| DE102005019397A1 (de) * | 2005-04-25 | 2006-10-26 | Bayer Materialscience Ag | Polyurethan-Dispersionen mit verbesserten Verfilmungseigenschaften |
| JP4984218B2 (ja) * | 2006-08-30 | 2012-07-25 | 日本ポリウレタン工業株式会社 | ポリウレタンポリ尿素系樹脂組成物 |
| WO2008049745A1 (en) * | 2006-10-25 | 2008-05-02 | Ciba Holding Inc. | Color fast aromatic polyurethanes |
| US9587139B2 (en) | 2012-06-15 | 2017-03-07 | 3M Innovative Properties Company | Curable polyurea forming composition, method of making, and composite article |
| KR20170023104A (ko) | 2014-06-24 | 2017-03-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 폴리우레탄 에어로졸 조성물, 용품, 및 관련 방법 |
| US11485817B2 (en) | 2017-09-13 | 2022-11-01 | Allnex Belgium S.A. | Radiation curable aqueous compositions |
| EP3486290A1 (en) | 2017-11-21 | 2019-05-22 | Allnex Belgium, S.A. | Adhesion promoting compounds for apolar substrates |
| WO2019190997A1 (en) * | 2018-03-27 | 2019-10-03 | Advansix Resins & Chemicals Llc | Thixotropic rheology modifying agent compositions |
| CN112839973A (zh) * | 2018-08-24 | 2021-05-25 | 科思创知识产权两合公司 | 一种组合物、其制备方法和应用 |
| EP3640271A1 (en) | 2018-10-18 | 2020-04-22 | Covestro Deutschland AG | A polyurethane composition, preparation method and application thereof |
| CN110857329A (zh) * | 2018-08-24 | 2020-03-03 | 科思创德国股份有限公司 | 一种聚氨酯组合物及其制备方法和应用 |
| EP3841139B1 (en) * | 2018-08-24 | 2023-10-04 | Covestro Intellectual Property GmbH & Co. KG | A polyurethane composition, preparation method and application thereof |
| EP3640272A1 (en) | 2018-10-18 | 2020-04-22 | Covestro Deutschland AG | A composition, preparation method and application thereof |
| EP3686340A1 (de) | 2019-01-23 | 2020-07-29 | Covestro Deutschland AG | Kunstleder und verfahren zum herstellen eines kunstleders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5216078A (en) * | 1992-07-29 | 1993-06-01 | Basf Corporation | Isocyanate-crosslinked coating having reduced yellowing |
| 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 |
| DE19637334A1 (de) * | 1996-09-13 | 1998-03-19 | Bayer Ag | Stabilisierte blockierte Isocyanate |
| DE19738497A1 (de) * | 1997-09-03 | 1999-03-04 | Bayer Ag | Amin-blockierte Polyisocyanate |
| DE19750186A1 (de) | 1997-11-13 | 1999-05-20 | Bayer Ag | Hydrophilierungsmittel, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Dispergator für wäßrige Polyurethan-Dispersionen |
| DE19941213A1 (de) * | 1999-08-30 | 2001-03-01 | Bayer Ag | Malonester-blockiertes HDI-Trimerisat mit IPDA- und Formaldehydstabilisierung |
-
2002
- 2002-01-17 DE DE2002101546 patent/DE10201546A1/de not_active Withdrawn
-
2003
- 2003-01-10 AT AT03704369T patent/ATE319758T1/de active
- 2003-01-10 HK HK06100009.3A patent/HK1080094B/zh not_active IP Right Cessation
- 2003-01-10 AU AU2003206707A patent/AU2003206707A1/en not_active Abandoned
- 2003-01-10 ES ES03704369T patent/ES2260606T3/es not_active Expired - Lifetime
- 2003-01-10 EP EP20030704369 patent/EP1474487B1/de not_active Expired - Lifetime
- 2003-01-10 MX MXPA04006844A patent/MXPA04006844A/es unknown
- 2003-01-10 CA CA 2473411 patent/CA2473411C/en not_active Expired - Fee Related
- 2003-01-10 JP JP2003560107A patent/JP4494790B2/ja not_active Expired - Lifetime
- 2003-01-10 BR BR0302715A patent/BR0302715A/pt not_active IP Right Cessation
- 2003-01-10 WO PCT/EP2003/000160 patent/WO2003060017A2/de not_active Ceased
- 2003-01-10 KR KR10-2004-7011135A patent/KR20040083087A/ko not_active Ceased
- 2003-01-10 RU RU2004125181/04A patent/RU2004125181A/ru not_active Application Discontinuation
- 2003-01-10 DE DE50302604T patent/DE50302604D1/de not_active Expired - Lifetime
- 2003-01-10 DK DK03704369T patent/DK1474487T3/da active
- 2003-01-10 CN CNB038063492A patent/CN1290892C/zh not_active Expired - Lifetime
- 2003-01-14 US US10/341,880 patent/US7091280B2/en not_active Expired - Lifetime
- 2003-01-16 TW TW092100832A patent/TWI262197B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003206707A1 (en) | 2003-07-30 |
| HK1080094B (zh) | 2007-08-03 |
| JP4494790B2 (ja) | 2010-06-30 |
| KR20040083087A (ko) | 2004-09-30 |
| EP1474487B1 (de) | 2006-03-08 |
| WO2003060017A3 (de) | 2004-05-21 |
| DE10201546A1 (de) | 2003-07-31 |
| US7091280B2 (en) | 2006-08-15 |
| ATE319758T1 (de) | 2006-03-15 |
| ES2260606T3 (es) | 2006-11-01 |
| BR0302715A (pt) | 2004-07-06 |
| HK1080094A1 (en) | 2006-04-21 |
| US20030194556A1 (en) | 2003-10-16 |
| CA2473411A1 (en) | 2003-07-24 |
| JP2005514513A (ja) | 2005-05-19 |
| CN1643018A (zh) | 2005-07-20 |
| EP1474487A2 (de) | 2004-11-10 |
| RU2004125181A (ru) | 2006-02-20 |
| CA2473411C (en) | 2011-03-22 |
| TW200307027A (en) | 2003-12-01 |
| WO2003060017A2 (de) | 2003-07-24 |
| DE50302604D1 (de) | 2006-05-04 |
| MXPA04006844A (es) | 2004-12-08 |
| CN1290892C (zh) | 2006-12-20 |
| AU2003206707A8 (en) | 2003-07-30 |
| DK1474487T3 (da) | 2006-07-03 |
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| Date | Code | Title | Description |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |