JP4266721B2 - ポリウレタン−ポリ尿素分散物 - Google Patents
ポリウレタン−ポリ尿素分散物 Download PDFInfo
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- JP4266721B2 JP4266721B2 JP2003171662A JP2003171662A JP4266721B2 JP 4266721 B2 JP4266721 B2 JP 4266721B2 JP 2003171662 A JP2003171662 A JP 2003171662A JP 2003171662 A JP2003171662 A JP 2003171662A JP 4266721 B2 JP4266721 B2 JP 4266721B2
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- Prior art keywords
- dispersion
- post
- polyurethane
- dispersions
- compounds
- 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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- 239000006185 dispersion Substances 0.000 title claims abstract description 82
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 24
- 239000002981 blocking agent Substances 0.000 claims abstract description 22
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- 239000005056 polyisocyanate Substances 0.000 claims abstract description 18
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 18
- 125000003010 ionic group Chemical group 0.000 claims abstract description 11
- 150000003974 aralkylamines Chemical class 0.000 claims abstract description 8
- 229920000768 polyamine Polymers 0.000 claims abstract description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 239000003365 glass fiber Substances 0.000 abstract description 17
- 150000003077 polyols Chemical class 0.000 abstract description 13
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- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 239000008199 coating composition Substances 0.000 abstract description 8
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- 239000000203 mixture Substances 0.000 description 27
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- 229920000570 polyether Polymers 0.000 description 26
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- 238000000576 coating method Methods 0.000 description 17
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 14
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 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 4
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- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 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
- 239000004971 Cross linker Substances 0.000 description 3
- 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
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical class [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000010422 painting Methods 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 2
- NNLRDVBAHRQMHK-UHFFFAOYSA-N 3-(2-aminoethylamino)propanoic acid Chemical compound NCCNCCC(O)=O NNLRDVBAHRQMHK-UHFFFAOYSA-N 0.000 description 2
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- OUMBFMLKPJUWDQ-UHFFFAOYSA-N n-benzylpropan-1-amine Chemical compound CCCNCC1=CC=CC=C1 OUMBFMLKPJUWDQ-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- GNLZSEMKVZGLGY-UHFFFAOYSA-N pentane-2,2-diol Chemical compound CCCC(C)(O)O GNLZSEMKVZGLGY-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000090 poly(aryl ether) Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01K—ANIMAL HUSBANDRY; AVICULTURE; APICULTURE; PISCICULTURE; FISHING; REARING OR BREEDING ANIMALS, NOT OTHERWISE PROVIDED FOR; NEW BREEDS OF ANIMALS
- A01K63/00—Receptacles for live fish, e.g. aquaria; Terraria
- A01K63/003—Aquaria; Terraria
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/808—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B14/00—Use of inorganic materials as fillers, e.g. pigments, for mortars, concrete or artificial stone; Treatment of inorganic materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone
- C04B14/02—Granular materials, e.g. microballoons
- C04B14/04—Silica-rich materials; Silicates
- C04B14/10—Clay
-
- 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
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Ceramic Engineering (AREA)
- Structural Engineering (AREA)
- Civil Engineering (AREA)
- Dispersion Chemistry (AREA)
- Marine Sciences & Fisheries (AREA)
- Animal Husbandry (AREA)
- Biodiversity & Conservation Biology (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Laminated Bodies (AREA)
Description
水性後架橋性PU分散物の調製は、通常、先行技術のブロック化剤(例えば、ε−カプロラクタムおよびブタノンオキシムなど)の使用を含む。
先行技術の後架橋性PU分散物のさらなる欠点は、フィルムおよび塗膜における加水分解安定性が低いことである。
本発明は、以下の成分:
A1)ポリイソシアネート、
A2)平均分子量が400〜6000のポリマーポリオール、
A3)任意に、平均分子量が400までのモノ−若しくはポリアルコールまたはモノ−若しくはポリアミン、
A4)少なくとも20質量%がアラルキルアミンから構成されている、少なくとも1つのブロック化剤、
並びに
A5)少なくとも1つのイオン性基または潜在的イオン性基を有する化合物および/または
A6)非イオン親水性化合物としての少なくとも1つの水酸基またはアミノ基を有するポリオキシアルキレンエーテル
から選択される少なくとも1つの化合物、
加えて所望により希釈剤、溶媒、および補助剤
から構成される、アルキルアミンでブロック化されたイソシアネートを含む後架橋性水性PU分散物を提供する。
成分A1)〜A6)から得られる分散ポリマーは、もはやいかなるイソシアネート反応性基を含まない。
好ましくは、本発明のPU分散物は、10〜40質量%のA1)、30〜90質量%のA2)、0〜30質量%のA3)、1〜20質量%のA4)、0〜15質量%のイオン性または潜在的イオン性化合物A5)、および0〜40質量%の化合物A6)を含み、成分の合計は100質量%である。
最も好ましくは、PU分散物は、15〜30質量%のA1)、30〜70質量%のA2)、0〜10質量%のA3)、1〜10質量%のA4)、0〜8質量%のイオン性または潜在的イオン性化合物A5)、および5〜30質量%の化合物A6)を含み、成分の合計は100質量%である。
本発明のPU分散物のポリイソシアネート(A1)のイソシアネート基の少なくとも5%、好ましくは少なくとも10%、特に好ましくは少なくとも15%が、ブロック化された形態である。
他の適切なポリエーテルポリオールは、例えば、開始分子を使用してスチレンオキシド、プロピレンオキシド、ブチレンオキシド、またはエピクロロヒドリン、特にプロピレンオキシドから調製したポリオールのようなポリエーテルである。
対応する多数の文献に記載の分子量400未満のポリオール、アミノポリオール、またはポリアミンもまた、成分(A3)として適切である。
a)アルカンジオール(エタンジオール、1,2−および1,3−プロパンジオール、1,4−および2,3−ブタンジオール、1,5−ペンタンジオール、1,3−ジメチルプロパンジオール、1,6−ヘキサンジオール、ネオペンチルグリコール、シクロヘキサンジメタノール、および2−メチル−1,3−プロパンジオールなど)、
b)エーテルジオール(ジエチレンジグリコール、トリエチレングリコール、またはヒドロキノンジヒドロキシエチルエーテルなど)、
c)一般式(III)および(IV):
HO−(CH2)x−CO−O−(CH2)y−OH (III)
HO−(CH2)x−O−CO−R−CO−O−(CH2)x−OH (IV)
(式中、Rは、1〜10個のC原子、好ましくは2〜6個のC原子を有するアルキレンまたはアリーレン基であり、
xは2〜6であり、
yは3〜5である)
で示されるエステルジオール(例えば、δ−ヒドロキシブチル−ε−ヒドロキシカプロエート、ω−ヒドロキシヘキシル−γ−ヒドロキシブチレート、β−ヒドロキシエチルアジペート、およびビス(β−ヒドロキシ−エチル)テレフタレートなど)、および
d)ポリアミン(エチレンジアミン、1,2−および1,3−ジアミンプロパン、1,4−ジアミノブタン、1,6−ジアミノヘキサン、イソホロンジアミン、2,2,4−および2,4,4−トリメチルヘキサメチレンジアミンの異性体混合物、2−メチル−ペンタメチレンジアミン、ジエチレントリアミン、1,3−および1,4−キシリレンジアミン、α,α,α’,α’−テトラメチル−1,3−および1,4−キシリレンジアミン、および4,4−ジアミノジシクロヘキシルメタンなど)。本発明において適切なジアミンはまた、ヒドラジン、ヒドラジン水化物、および置換ヒドラジン(例えば、N−メチルヒドラジン、N,N’−ジメチルヒドラジン、およびその同族体)、および酸ジヒドラジド、アジピン酸、β−メチルアジピン酸、セバシン酸、ヒドロアクリル酸、およびテトラフタル酸、セミカルバジドアルキレンヒドラジド(例えば、β−セミカルバジドプロピオン酸ヒドラジド(例えば、独国特許出願公開第1770591号)など)、セミカルバジドアルキレン−カルバジンエステル(例えば、2−セミカルバジドエチルカルバジンエステル(例えば、独国特許出願公開第1918504号)など)またはアミノセミカルバジド化合物(例えば、β−アミノエチルセミカルバジド−カーボネート(例えば、独国特許出願公開第1902931号)など)である。
R4は、C1〜C4アルキル、C6〜C10シクロアルキル、またはC1〜C14アラルキル、好ましくはメチル、エチル、イソプロピル、およびtert−ブチル、特に好ましくはtert−ブチルを示し、
xは1、2、3、4、または5の数を示す)
に相当する。
R3は、ヒドロキシル末端ではない、ポリエステルまたは好ましくはポリエーテルを示し、R3は、特に好ましくはアルコキシ末端ポリエチレンオキシドの基を示す。)
で示される化合物も含まれる。
アルコキシル化反応に特に適切なアルキレンオキシドは、エチレンオキシドおよびプロピレンオキシドであり、これらを、アルコキシル化反応のために任意の順序あるいは混合物中で使用することができる。
しかし、ポリイソシアネートの乳化が向上し、それにより塗膜の質が向上するので、300nm未満の平均粒度が好ましい。
同様に、本発明は、ペイントおよび塗料組成物での本発明のPU分散物の使用を提供する。後架橋性ポリウレタン−ポリ尿素分散物を、配合物に添加してサイズ剤を生成することができる。
塗料物質を、既知の方法(例えば、ブラッシング、流し込み、ナイフコーティング、スプレー、ローリング、または浸漬)で適用することができる。塗膜を、室温または高温で、または200℃までの焼付けにより乾燥することができる。
さらに、適用前にさらなる架橋剤を添加することが可能である。この目的に適切な架橋剤は、好ましくは親水性または親水化ポリイソシアネート架橋剤である。
本発明はまた、本発明のPU分散物を含むサイズ剤を施したガラス繊維を提供する。
正確な間隔でセットすることができる2つの磨きロールからなるフィルムアプリケーターは、後ロールの前方に挿入した剥離紙を有する。紙と前ロールとの間の距離を、厚みゲージを使用して調整した。この距離は、得られた塗膜の未乾燥の膜厚に対応し、これを各塗膜の所望追加量に調整することができる。塗装を、2つまたはそれ以上の塗膜で連続的に行うこともできる。各塗膜を適用するために、生成物(水性配合物を、アンモニア/ポリアクリル酸の添加によって予め4500mPaの粘度に調整する)を、紙と前ロールとの間のニップに注ぎ、剥離紙を垂直の下方向に引き抜き、対応するフィルムを紙上で形成させた。2つまたはそれ以上の塗膜を適用する場合、各塗膜を乾燥させ、紙を再挿入した。
PU分散物の平均粒度(平均値を示す)を、レーザー相関分光法(装置:Malvern Zetasizer 1000、Malver Inst.Limited)によって測定した。
加水分解条件下でのフィルム貯蔵を、DIN EN12280−3によって行う。これらのフィルム試料の機械的性質を、DIN53504によって標準的な条件下(20℃、湿度65%)での24時間の貯蔵後に測定する。
128.8gのポリエーテル Desmophen(商標)3600Z(Bayer AG、ドイツ、平均分子量2000(OH価=56)のプロピレンオキシドベースの二官能性ポリエーテル)、25.6gのPolyether(商標)L400(Bayer AG、ドイツ、平均分子量561(OH価=200)のプロピレンオキシドベースの二官能性ポリエーテル)、86.4gのPolyether LB25(Bayer AG、ドイツ、平均分子量2250(OH価=25)のエチレンオキシド/プロピレンオキシドベースの単官能性ポリエーテル)、および21.5gのN−tert−ブチルベンジルアミンを、容器に導入し、70℃に加熱する。次いで、100.01gのDesmodur(商標)W(Bayer AG、ドイツ)を5分間にわたり添加する。その後75℃で45分間撹拌する。5.2gのトリメチロールプロパンの添加後、反応混合物を理論NCO値に達するまで75℃で撹拌し、60℃に冷却する。10分間にわたる527.0gの水(20℃)の添加により分散させる。分散直後に1.70gのヒドラジン一水化物、10.2gのイソホロンジアミン、および178.6gの水の溶液を、40℃で5分間にわたり添加した。その後40℃で3時間撹拌する。これにより、固形分33.0%を有し、ブロックトイソシアネート基を含む貯蔵安定な水性PU分散物が得られる。
128.8gのポリエーテル Desmophen(商標)3600Z(Bayer AG、ドイツ、平均分子量2000(OH価=56)のプロピレンオキシドベースの二官能性ポリエーテル)、25.6gのPolyether L400(Bayer AG、ドイツ、平均分子量561(OH価=200)のプロピレンオキシドベースの二官能性ポリエーテル)、86.4gのPolyether LB25(Bayer AG、ドイツ、平均分子量2250(OH価=25)のエチレンオキシド/プロピレンオキシドベースの単官能性ポリエーテル)、および14.9gのεカプロラクタムを、容器に導入し、70℃に加熱する。次いで、100.01gのDesmodur(商標)W(Bayer AG、ドイツ)を5分間にわたり添加し、反応混合物を100℃に加熱する。その後100℃で45分間撹拌する。5.2gのトリメチロールプロパンの添加後、反応混合物を理論NCO値に達するまで100℃で撹拌し、60℃に冷却する。10分間にわたる527.0gの水(20℃)の添加により分散させる。分散直後に1.70gのヒドラジン一水化物、10.2gのイソホロンジアミン、および178.6gの水の溶液を、40℃で5分間にわたり添加した。その後40℃で3時間撹拌する。これにより、固形分34.6%を有し、ブロックトイソシアネート基を含む貯蔵安定な水性PU分散物が得られる。
[1]
A1)ポリイソシアネート、
A2)平均分子量が400〜6000のポリマーポリオール、
A3)任意に、平均分子量が400までのモノ−若しくはポリアルコールまたはモノ−若しくはポリアミン、
A4)少なくとも20質量%がアラルキルアミンから構成されている、少なくとも1つのブロック化剤、
並びに
A5)少なくとも1つのイオン性基または潜在的イオン性基を有する化合物と
A6)非イオン親水性化合物と
から選択される少なくとも1つの化合物
から構成される、後架橋性ポリウレタン−ポリ尿素分散物。
[2]
成分A1)のイソシアネート基の少なくとも5%が、ブロックされた形態である前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[3]
分散物の固形分が、10〜70質量%である前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[4]
分散物の溶媒割合が、全組成物の15質量%未満である前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[5]
ブロック化剤としてアラルキルアミンを使用する、前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[6]
ブロック化剤として第二級ベンジルアミンを使用する、前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[7]
ブロック化剤としてN−tert−ブチルベンジルアミンを使用する、前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物。
[8]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を、配合物に添加することを含むペイントおよび塗料組成物の1つを製造する方法。
[9]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を配合物に添加することを含む、サイズ剤を製造する方法。
[10]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を配合物に添加することを含む、ガラス繊維用サイズ剤を製造する方法。
[11]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を含む、塗料組成物。
[12]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を含む、サイズ剤。
[13]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を含む、ガラス繊維用サイズ剤。
[14]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を含む塗料組成物で塗装した基材。
[15]
前記[1]項に記載の後架橋性ポリウレタン−ポリ尿素分散物を含むサイズ剤を施したガラス繊維。
本発明を説明目的で上記で詳細に説明しているが、このような詳細は説明の目的のためだけであり、特許請求の範囲で制限され得る場合を除いては、本発明の意図および範囲を逸脱することなく当業者がその変形形態を行うことができると理解すべきである。
Claims (1)
- A1)ポリイソシアネート、
A2)平均分子量が400〜6000のポリオール、
A3)任意に、平均分子量が400までのモノ−若しくはポリアルコールまたはモノ−若しくはポリアミン、
A4)少なくとも20質量%がアラルキルアミンから構成されている、少なくとも1つのブロック化剤、
並びに
A5)少なくとも1つのイオン性基または潜在的イオン性基を有する化合物と
A6)非イオン親水性化合物としての少なくとも1つの水酸基またはアミノ基を有するポリオキシアルキレンエーテルと
から選択される少なくとも1つの化合物
から構成される、後架橋性ポリウレタン−ポリ尿素分散物。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10226931A DE10226931A1 (de) | 2002-06-17 | 2002-06-17 | Polyurethan-Polyharnstoff Dispersionen |
Publications (3)
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JP2004131691A JP2004131691A (ja) | 2004-04-30 |
JP2004131691A5 JP2004131691A5 (ja) | 2006-08-03 |
JP4266721B2 true JP4266721B2 (ja) | 2009-05-20 |
Family
ID=29594580
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JP2003171662A Expired - Fee Related JP4266721B2 (ja) | 2002-06-17 | 2003-06-17 | ポリウレタン−ポリ尿素分散物 |
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EP (1) | EP1375549B1 (ja) |
JP (1) | JP4266721B2 (ja) |
KR (1) | KR100966692B1 (ja) |
CN (1) | CN1266185C (ja) |
AT (1) | ATE346876T1 (ja) |
AU (1) | AU2003204731B2 (ja) |
BR (1) | BR0302140A (ja) |
CA (1) | CA2431825C (ja) |
DE (2) | DE10226931A1 (ja) |
ES (1) | ES2278090T3 (ja) |
HK (1) | HK1062571A1 (ja) |
MX (1) | MXPA03005351A (ja) |
PT (1) | PT1375549E (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
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DE10226927A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Blockierte Polyisocyanate |
DE10328993A1 (de) * | 2003-06-27 | 2005-01-20 | Bayer Materialscience Ag | Blockierte Polyisocyanate |
DE10360368A1 (de) * | 2003-12-22 | 2005-07-21 | Bayer Materialscience Ag | Dispersionen |
DE102004049592A1 (de) * | 2004-10-12 | 2006-05-04 | Bayer Materialscience Ag | Mit Soft-Touch-Lack beschichtete, verformbare Kunststoffverbundfolien und Kunststoffverbundelemente sowie deren Herstellung |
US7371807B2 (en) * | 2004-10-21 | 2008-05-13 | Bayer Materialscience Llc | Blocked biuretized isocyanates |
JP4766370B2 (ja) * | 2005-04-28 | 2011-09-07 | 日本ポリウレタン工業株式会社 | 水性ポリウレタン樹脂エマルジョン組成物及びその製造方法 |
FR2886299B1 (fr) * | 2005-05-26 | 2010-08-20 | Saint Gobain Vetrotex | Dispersion de polymere dans un milieu organique reactif, procede de preparation et utilisations |
DE102007054002A1 (de) * | 2007-11-13 | 2009-05-14 | Bayer Materialscience Ag | Nicht-ionisch hydrophilierte Bindemittel-Dispersionen |
WO2009098226A1 (de) | 2008-02-05 | 2009-08-13 | Technische Fachhochschule Wildau | Polyharnstoff-nanodispersionspolyole und verfahren zu ihrer herstellung |
DE102008025091C5 (de) | 2008-05-26 | 2017-03-30 | Hans Tiefenbach GmbH | Verfahren zur Behandlung von Gesteinsoberflächen |
CN103180397B (zh) * | 2010-10-22 | 2016-04-13 | 卡博特公司 | 油墨组合物 |
DE102013224140A1 (de) | 2013-11-26 | 2015-05-28 | Rudolf Gmbh | Ausrüstungsmittel mit blockierten Polyisocyanaten |
JP2020506256A (ja) * | 2017-01-13 | 2020-02-27 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 織物用の低溶剤コーティング系 |
CN108456504B (zh) * | 2018-03-06 | 2021-03-12 | 吉林大学珠海学院 | 一步法合成的单组份聚氨酯粉末胶粘剂及其制备方法 |
JP7017481B2 (ja) * | 2018-06-29 | 2022-02-08 | 理想科学工業株式会社 | 油性インクジェットインク |
CN109666124B (zh) * | 2018-12-12 | 2020-12-22 | 合众(佛山)化工有限公司 | 一种聚苯乙烯微球改性聚氨酯水性树脂及制备方法 |
CN111423837B (zh) * | 2020-04-08 | 2022-04-05 | 上海抚佳精细化工有限公司 | 一种tpu热熔胶及其制备方法 |
CN113861377B (zh) * | 2020-06-30 | 2023-07-14 | 万华化学集团股份有限公司 | 一种水性聚氨酯-聚脲分散体树脂及其制备方法和应用 |
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DE3221558A1 (de) * | 1982-06-08 | 1983-12-08 | Chemische Werke Hüls AG, 4370 Marl | Lagerstabile polyurethan-einkomponenten-einbrennlacke |
DE3434881A1 (de) * | 1984-09-22 | 1986-04-03 | Hüls AG, 4370 Marl | Lagerstabile polyurethanharz-pulverlacke |
DE19548030A1 (de) * | 1995-12-21 | 1997-06-26 | Bayer Ag | Verwendung wässriger Dispersionen nachvernetzbarer Beschichtungsmittel zur Textil- und Lederbeschichtung |
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KR100966692B1 (ko) | 2010-06-29 |
EP1375549A1 (de) | 2004-01-02 |
MXPA03005351A (es) | 2004-04-21 |
ATE346876T1 (de) | 2006-12-15 |
KR20040002535A (ko) | 2004-01-07 |
BR0302140A (pt) | 2004-09-08 |
PT1375549E (pt) | 2007-01-31 |
AU2003204731B2 (en) | 2007-06-14 |
DE10226931A1 (de) | 2003-12-24 |
DE50305812D1 (de) | 2007-01-11 |
AU2003204731A1 (en) | 2004-01-15 |
JP2004131691A (ja) | 2004-04-30 |
CA2431825A1 (en) | 2003-12-17 |
CA2431825C (en) | 2011-02-22 |
CN1266185C (zh) | 2006-07-26 |
ES2278090T3 (es) | 2007-08-01 |
HK1062571A1 (en) | 2004-11-12 |
CN1468882A (zh) | 2004-01-21 |
EP1375549B1 (de) | 2006-11-29 |
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