NL1013301C2 - Werkwijze voor de bereiding van een dispersie van een anionische polyurethaan in water waarin geen vluchtige tertiaire amines voorkomen. - Google Patents
Werkwijze voor de bereiding van een dispersie van een anionische polyurethaan in water waarin geen vluchtige tertiaire amines voorkomen. Download PDFInfo
- Publication number
- NL1013301C2 NL1013301C2 NL1013301A NL1013301A NL1013301C2 NL 1013301 C2 NL1013301 C2 NL 1013301C2 NL 1013301 A NL1013301 A NL 1013301A NL 1013301 A NL1013301 A NL 1013301A NL 1013301 C2 NL1013301 C2 NL 1013301C2
- Authority
- NL
- Netherlands
- Prior art keywords
- tertiary amine
- functional
- dispersion
- process according
- functions
- Prior art date
Links
- 150000003512 tertiary amines Chemical class 0.000 title claims abstract description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000006185 dispersion Substances 0.000 title claims abstract description 31
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 29
- 239000004814 polyurethane Substances 0.000 title claims abstract description 28
- 125000000129 anionic group Chemical group 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 26
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 16
- -1 anionic isocyanate Chemical class 0.000 claims abstract description 13
- 239000012948 isocyanate Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 34
- 230000003472 neutralizing effect Effects 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229920003009 polyurethane dispersion Polymers 0.000 claims description 12
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 150000001412 amines Chemical group 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 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 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 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 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 5
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000006224 matting agent Substances 0.000 claims description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical group OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 3
- BXYVQNNEFZOBOZ-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-n',n'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNCCCN(C)C BXYVQNNEFZOBOZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- BHUXAQIVYLDUQV-UHFFFAOYSA-N 1-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(C)O BHUXAQIVYLDUQV-UHFFFAOYSA-N 0.000 claims description 2
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 claims description 2
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 claims description 2
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 2
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 claims description 2
- WKCYFSZDBICRKL-UHFFFAOYSA-N 3-(diethylamino)propan-1-ol Chemical compound CCN(CC)CCCO WKCYFSZDBICRKL-UHFFFAOYSA-N 0.000 claims description 2
- LTACQVCHVAUOKN-UHFFFAOYSA-N 3-(diethylamino)propane-1,2-diol Chemical compound CCN(CC)CC(O)CO LTACQVCHVAUOKN-UHFFFAOYSA-N 0.000 claims description 2
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 claims description 2
- OAQYRNDEOJQVBN-UHFFFAOYSA-N 5-(diethylamino)pentan-2-ol Chemical compound CCN(CC)CCCC(C)O OAQYRNDEOJQVBN-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 239000012972 dimethylethanolamine Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 230000004907 flux Effects 0.000 claims description 2
- 239000002529 flux (metallurgy) Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000002649 leather substitute Substances 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 239000011087 paperboard Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 239000004753 textile Substances 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
- 239000002023 wood Substances 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims 2
- 239000013589 supplement Substances 0.000 claims 2
- IFPDWCHTHGPOKN-UHFFFAOYSA-N 2,3-dimethylbutane-1,3-diamine Chemical compound NCC(C)C(C)(C)N IFPDWCHTHGPOKN-UHFFFAOYSA-N 0.000 claims 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 claims 1
- TWWCBLSUGOSDIY-UHFFFAOYSA-N 2-ethyl-1,1-dimethylhydrazine Chemical compound CCNN(C)C TWWCBLSUGOSDIY-UHFFFAOYSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical group 0.000 claims 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 1
- NWOJEYNEKIVOOF-UHFFFAOYSA-N hexane-2,2-diamine Chemical compound CCCCC(C)(N)N NWOJEYNEKIVOOF-UHFFFAOYSA-N 0.000 claims 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims 1
- 239000000159 acid neutralizing agent Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 10
- 239000007787 solid Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 150000007857 hydrazones Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 125000005597 hydrazone group Chemical group 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- BZOHHLMTCXVRJE-UHFFFAOYSA-N 2-(hydroxymethyl)-1,3-dihydroinden-2-ol Chemical compound C1=CC=C2CC(CO)(O)CC2=C1 BZOHHLMTCXVRJE-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- QCMHUGYTOGXZIW-UHFFFAOYSA-N 3-(dimethylamino)propane-1,2-diol Chemical compound CN(C)CC(O)CO QCMHUGYTOGXZIW-UHFFFAOYSA-N 0.000 description 1
- OYYXNGVBOWXTPN-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]propane-1,2-diol Chemical compound CC(C)N(C(C)C)CC(O)CO OYYXNGVBOWXTPN-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 238000012546 transfer Methods 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
- C08G18/08—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
-
- 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
-
- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249924—Noninterengaged fiber-containing paper-free web or sheet which is not of specified porosity
- Y10T428/24994—Fiber embedded in or on the surface of a polymeric matrix
-
- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249962—Void-containing component has a continuous matrix of fibers only [e.g., porous paper, etc.]
-
- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249962—Void-containing component has a continuous matrix of fibers only [e.g., porous paper, etc.]
- Y10T428/249964—Fibers of defined composition
- Y10T428/249965—Cellulosic
-
- 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
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249987—With nonvoid component of specified composition
- Y10T428/249991—Synthetic resin or natural rubbers
-
- 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.]
-
- 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.]
- Y10T428/31558—Next to animal skin or membrane
-
- 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.]
- Y10T428/31591—Next to cellulosic
-
- 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
-
- 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.]
- Y10T428/31605—Next to free metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1013301A NL1013301C2 (nl) | 1999-10-15 | 1999-10-15 | Werkwijze voor de bereiding van een dispersie van een anionische polyurethaan in water waarin geen vluchtige tertiaire amines voorkomen. |
| US09/857,004 US6599977B1 (en) | 1999-10-15 | 2000-10-16 | Process for the preparation of an aqueous dispersion of an anionic polyurethane free of volatile tertiary amines |
| KR1020017007435A KR20010093832A (ko) | 1999-10-15 | 2000-10-16 | 휘발형 3급아민 무함유 음이온성 폴리우레탄의 수성분산물 제조방법 |
| ES00973265T ES2235976T3 (es) | 1999-10-15 | 2000-10-16 | Proceso para la preparacion de dispersiones acuosas de poliuretanos anionicos, las dispersiones obtenidas y un substrato o pelicula recubierta obtenida con dicha dispersion. |
| PCT/NL2000/000741 WO2001027179A1 (en) | 1999-10-15 | 2000-10-16 | Process for the preparation of an aqueous dispersion of an anionic polyurethane free of volatile tertiary amines |
| BR0007217-6A BR0007217A (pt) | 1999-10-15 | 2000-10-16 | Processo para a preparação de uma dispersãoaquosa de um poliuretano aniÈnico livre de aminasterciárias voláteis |
| JP2001530395A JP2003511529A (ja) | 1999-10-15 | 2000-10-16 | 揮発性第３級アミンを含まない、アニオン系ポリウレタンの水性分散系の調製方法 |
| AT00973265T ATE286085T1 (de) | 1999-10-15 | 2000-10-16 | Verfahren zur herstellung einer wässrigen dispersion eines anionischen polyurethanes flüchtiger tertiären aminen |
| TR2001/01771T TR200101771T1 (tr) | 1999-10-15 | 2000-10-16 | Uçucu tertiyer amin içermeyen anyonik bir poliüretanın sulu dispersiyonunun hazırlanması için proses. |
| PT00973265T PT1153052E (pt) | 1999-10-15 | 2000-10-16 | Processo para a preparacao de uma dispersao aquosa de um poliuretano anionico isento de aminas terciarias volateis |
| AU11794/01A AU775087B2 (en) | 1999-10-15 | 2000-10-16 | Process for the preparation of an aqueous dispersion of an anionic polyurethane free of volatile tertiary amines |
| EP00973265A EP1153052B1 (de) | 1999-10-15 | 2000-10-16 | Verfahren zur herstellung einer wässrigen dispersion eines anionischen polyurethanes flüchtiger tertiären aminen |
| DK00973265T DK1153052T3 (da) | 1999-10-15 | 2000-10-16 | Fremgangsmåde til fremstilling af en vandig dispersion af en anionisk polyurethan, som er fri for flygtige, tertiære aminer |
| DE60017094T DE60017094T2 (de) | 1999-10-15 | 2000-10-16 | Verfahren zur Herstellung einer wässrigen Dispersion eines anionischen Polyurethanes, die keine flüchtingen tertriären Amine enthält |
| IDW00200101275A ID29918A (id) | 1999-10-15 | 2000-10-16 | Proses pembuatan dispersi berair poliuretana anionik bebas amina-amina tersier asiri |
| ZA200104893A ZA200104893B (en) | 1999-10-15 | 2001-06-14 | Process for the preparation of an aqueous dispersion of an anionic polyurethane free of volatile tertiary amines. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1013301A NL1013301C2 (nl) | 1999-10-15 | 1999-10-15 | Werkwijze voor de bereiding van een dispersie van een anionische polyurethaan in water waarin geen vluchtige tertiaire amines voorkomen. |
| NL1013301 | 1999-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL1013301C2 true NL1013301C2 (nl) | 2001-04-18 |
Family
ID=19770060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL1013301A NL1013301C2 (nl) | 1999-10-15 | 1999-10-15 | Werkwijze voor de bereiding van een dispersie van een anionische polyurethaan in water waarin geen vluchtige tertiaire amines voorkomen. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6599977B1 (de) |
| EP (1) | EP1153052B1 (de) |
| JP (1) | JP2003511529A (de) |
| KR (1) | KR20010093832A (de) |
| AT (1) | ATE286085T1 (de) |
| AU (1) | AU775087B2 (de) |
| BR (1) | BR0007217A (de) |
| DE (1) | DE60017094T2 (de) |
| ES (1) | ES2235976T3 (de) |
| ID (1) | ID29918A (de) |
| NL (1) | NL1013301C2 (de) |
| PT (1) | PT1153052E (de) |
| TR (1) | TR200101771T1 (de) |
| WO (1) | WO2001027179A1 (de) |
| ZA (1) | ZA200104893B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040005448A (ko) * | 2002-07-10 | 2004-01-16 | 한국신발피혁연구소 | 에틸알코올형 폴리우레탄 접착제의 제조방법 |
| KR100503072B1 (ko) * | 2002-10-25 | 2005-07-21 | 삼성전자주식회사 | 오버코트층 형성용 조성물 및 이를 채용한 유기감광체 |
| BRPI0617075A2 (pt) * | 2005-09-02 | 2011-07-12 | Dow Global Technologies Inc | dispersão de poliuretano aquosa, uso de uma dispersão de poliuretano e dispersão de poliuretano isenta de solvente |
| KR100785346B1 (ko) | 2006-06-02 | 2007-12-18 | 구자은 | 피혁용 비이온성 수분산 폴리우레탄 |
| JP2010248466A (ja) * | 2009-03-25 | 2010-11-04 | Toyo Ink Mfg Co Ltd | ラミネート用印刷インキ組成物 |
| DE102009014699A1 (de) | 2009-03-27 | 2010-10-07 | Carl Freudenberg Kg | Verfahren zur Herstellung einer reaktiven Polyurethan-Emulsion |
| WO2013153094A1 (en) | 2012-04-10 | 2013-10-17 | Dsm Ip Assets B.V. | Polymer, composition and use |
| EP2836530B1 (de) | 2012-04-10 | 2020-05-27 | DSM IP Assets B.V. | Polymer, zusammensetzung und verwendung |
| WO2015052214A1 (en) | 2013-10-09 | 2015-04-16 | Dsm Ip Assets B.V. | Polymer, composition and use |
| EP3651934A1 (de) * | 2017-07-14 | 2020-05-20 | 3M Innovative Properties Company | Schleifartikel mit anionischem wasserlösungsmaterial und herstellungsverfahren |
| ES2993285T3 (en) | 2018-11-23 | 2024-12-26 | Basf Coatings Gmbh | Self-releasing in-mould-coating (imc) for coating substrates |
| JP7462628B2 (ja) | 2018-11-23 | 2024-04-05 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | コーティング部品の射出成型のための手動の方法 |
| ES2967998T3 (es) | 2018-11-23 | 2024-05-06 | Basf Coatings Gmbh | Procedimiento automatizado para moldear por inyección componentes revestidos |
| BR112021008471B1 (pt) | 2018-11-23 | 2023-04-04 | Basf Coatings Gmbh | Composição pigmentanda, e, processo para produzir uma moldagem revestida |
| US20240376283A1 (en) | 2021-10-11 | 2024-11-14 | Basf Coatings Gmbh | Method for producing coated non-crosslinking polymer materials |
| WO2023102069A1 (en) | 2021-12-01 | 2023-06-08 | Checkerspot, Inc. | Polyols, polyurethane dispersions, and uses thereof |
| CN114316191B (zh) * | 2022-01-10 | 2023-09-19 | 万华化学集团股份有限公司 | 一种聚氨酯聚脲水分散体及其制备方法与用途 |
| CN115746242A (zh) * | 2022-11-03 | 2023-03-07 | 华南理工大学 | 一种高回弹低模量水性聚氨酯及其制备方法与应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0219677A1 (de) * | 1985-09-23 | 1987-04-29 | Miles Inc. | Verfahren zur Herstellung einer wässrigen Polyurethanharnstoffdispersion |
| EP0717057A1 (de) * | 1994-12-15 | 1996-06-19 | Minnesota Mining And Manufacturing Company | Sulfo-Polyurethan oder Sulfo-Polyharnstoff-Zusammensetzungen mit niedriger Oberflächenenergie |
-
1999
- 1999-10-15 NL NL1013301A patent/NL1013301C2/nl not_active IP Right Cessation
-
2000
- 2000-10-16 KR KR1020017007435A patent/KR20010093832A/ko not_active Withdrawn
- 2000-10-16 TR TR2001/01771T patent/TR200101771T1/xx unknown
- 2000-10-16 AT AT00973265T patent/ATE286085T1/de not_active IP Right Cessation
- 2000-10-16 DE DE60017094T patent/DE60017094T2/de not_active Expired - Fee Related
- 2000-10-16 PT PT00973265T patent/PT1153052E/pt unknown
- 2000-10-16 US US09/857,004 patent/US6599977B1/en not_active Expired - Fee Related
- 2000-10-16 EP EP00973265A patent/EP1153052B1/de not_active Expired - Lifetime
- 2000-10-16 JP JP2001530395A patent/JP2003511529A/ja active Pending
- 2000-10-16 BR BR0007217-6A patent/BR0007217A/pt not_active Application Discontinuation
- 2000-10-16 ID IDW00200101275A patent/ID29918A/id unknown
- 2000-10-16 WO PCT/NL2000/000741 patent/WO2001027179A1/en not_active Ceased
- 2000-10-16 ES ES00973265T patent/ES2235976T3/es not_active Expired - Lifetime
- 2000-10-16 AU AU11794/01A patent/AU775087B2/en not_active Ceased
-
2001
- 2001-06-14 ZA ZA200104893A patent/ZA200104893B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0219677A1 (de) * | 1985-09-23 | 1987-04-29 | Miles Inc. | Verfahren zur Herstellung einer wässrigen Polyurethanharnstoffdispersion |
| EP0717057A1 (de) * | 1994-12-15 | 1996-06-19 | Minnesota Mining And Manufacturing Company | Sulfo-Polyurethan oder Sulfo-Polyharnstoff-Zusammensetzungen mit niedriger Oberflächenenergie |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1153052A1 (de) | 2001-11-14 |
| JP2003511529A (ja) | 2003-03-25 |
| ZA200104893B (en) | 2002-09-16 |
| EP1153052B1 (de) | 2004-12-29 |
| DE60017094D1 (de) | 2005-02-03 |
| US6599977B1 (en) | 2003-07-29 |
| TR200101771T1 (tr) | 2002-02-21 |
| KR20010093832A (ko) | 2001-10-29 |
| ES2235976T3 (es) | 2005-07-16 |
| BR0007217A (pt) | 2001-11-27 |
| ID29918A (id) | 2001-10-25 |
| PT1153052E (pt) | 2005-04-29 |
| WO2001027179A1 (en) | 2001-04-19 |
| ATE286085T1 (de) | 2005-01-15 |
| AU1179401A (en) | 2001-04-23 |
| AU775087B2 (en) | 2004-07-15 |
| DE60017094T2 (de) | 2006-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD2B | A search report has been drawn up | ||
| VD1 | Lapsed due to non-payment of the annual fee |
Effective date: 20060501 |