CA2791557A1 - Aqueous polyurethane dispersions - Google Patents
Aqueous polyurethane dispersions Download PDFInfo
- Publication number
- CA2791557A1 CA2791557A1 CA2791557A CA2791557A CA2791557A1 CA 2791557 A1 CA2791557 A1 CA 2791557A1 CA 2791557 A CA2791557 A CA 2791557A CA 2791557 A CA2791557 A CA 2791557A CA 2791557 A1 CA2791557 A1 CA 2791557A1
- Authority
- CA
- Canada
- Prior art keywords
- radiation
- component
- acid
- aqueous dispersions
- curable
- 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.)
- Abandoned
Links
- 229920003009 polyurethane dispersion Polymers 0.000 title description 28
- 239000006185 dispersion Substances 0.000 claims abstract description 58
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 50
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 43
- 229920000728 polyester Polymers 0.000 claims abstract description 42
- 239000004814 polyurethane Substances 0.000 claims abstract description 39
- 229920002635 polyurethane Polymers 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 34
- 238000000576 coating method Methods 0.000 claims abstract description 33
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 27
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 27
- 239000000758 substrate Substances 0.000 claims abstract description 23
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 22
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 22
- 239000008199 coating composition Substances 0.000 claims abstract description 19
- 239000011248 coating agent Substances 0.000 claims abstract description 17
- 239000012948 isocyanate Substances 0.000 claims abstract description 12
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011630 iodine Substances 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 239000000853 adhesive Substances 0.000 claims abstract description 8
- 230000001070 adhesive effect Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 53
- -1 aromatic glycidyl ethers Chemical class 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 239000004922 lacquer Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 22
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000004359 castor oil Substances 0.000 claims description 14
- 235000019438 castor oil Nutrition 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 14
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 14
- 150000001412 amines Chemical group 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000003010 ionic group Chemical group 0.000 claims description 10
- 235000019198 oils Nutrition 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 9
- 235000012424 soybean oil Nutrition 0.000 claims description 9
- 239000002023 wood Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 239000003549 soybean oil Substances 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 3
- 239000004645 polyester resin Substances 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 36
- 229940048053 acrylate Drugs 0.000 description 34
- 238000001723 curing Methods 0.000 description 28
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 26
- 230000001590 oxidative effect Effects 0.000 description 25
- 239000002253 acid Substances 0.000 description 19
- 229920000570 polyether Polymers 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- 229930195729 fatty acid Natural products 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 17
- 150000004665 fatty acids Chemical class 0.000 description 17
- 238000003847 radiation curing Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 15
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 230000005855 radiation Effects 0.000 description 13
- 239000000470 constituent Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 239000004721 Polyphenylene oxide Substances 0.000 description 11
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 11
- 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 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000005058 Isophorone diisocyanate Substances 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 8
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 6
- 229920000058 polyacrylate Polymers 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 6
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 5
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 5
- WVQHODUGKTXKQF-UHFFFAOYSA-N 2-ethyl-2-methylhexane-1,1-diol Chemical compound CCCCC(C)(CC)C(O)O WVQHODUGKTXKQF-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 235000019486 Sunflower oil Nutrition 0.000 description 5
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 5
- 239000000944 linseed oil Substances 0.000 description 5
- 235000021388 linseed oil Nutrition 0.000 description 5
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 5
- 235000020095 red wine Nutrition 0.000 description 5
- 239000002600 sunflower oil Substances 0.000 description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 5
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 5
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
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- 125000002947 alkylene group Chemical group 0.000 description 4
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- 150000008064 anhydrides Chemical class 0.000 description 4
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- 239000003431 cross linking reagent Substances 0.000 description 4
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 239000003784 tall oil Substances 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 3
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical group O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 3
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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Classifications
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- 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
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- 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
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Landscapes
- Chemical & Material Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
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| DE102010009896.5 | 2010-03-02 | ||
| DE102010009896A DE102010009896A1 (de) | 2010-03-02 | 2010-03-02 | Wässrige Polyurethandispersionen |
| PCT/EP2011/052783 WO2011107398A1 (de) | 2010-03-02 | 2011-02-25 | Wässrige polyurethandispersionen |
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| CA2791557A1 true CA2791557A1 (en) | 2011-09-09 |
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| US10907005B2 (en) * | 2012-09-25 | 2021-02-02 | Battelle Memorial Institute | Aqueous prepolymer dispersions |
| US9752056B2 (en) * | 2012-10-24 | 2017-09-05 | Basf Se | Radiation-curing, water-dispersible polyurethane (meth)acrylates |
| EP2772917A1 (de) | 2013-02-27 | 2014-09-03 | Bayer MaterialScience AG | Schutzlacke auf Basis von strahlenvernetzbaren Polyurethandispersionen |
| WO2015075193A1 (en) * | 2013-11-22 | 2015-05-28 | Arkema France | Solvent-free aqueous curable polyurethane dispersions and methods of producing solvent-free aqueous polyurethane dispersions |
| CN106068293B (zh) * | 2014-02-28 | 2021-08-10 | 阿科玛法国公司 | 由可再生资源制造的可固化的水性聚氨酯分散体 |
| CA2941109A1 (en) * | 2014-03-12 | 2015-09-17 | Rust-Oleum Corporation | Vegetable oil-modified, hydrophobic polyurethane dispersions |
| US9460824B2 (en) * | 2014-04-23 | 2016-10-04 | Xerox Corporation | Stretchable conductive film based on silver nanoparticles |
| US20170049683A1 (en) * | 2014-04-30 | 2017-02-23 | Arkema France | Nail polish composition based on solvent-free aqueous polyurethane dispersions |
| EP3137530B1 (en) * | 2014-04-30 | 2020-05-27 | Arkema France | Curable aqueous polyurethane dispersions made from renewable resources. |
| US10793672B2 (en) | 2014-06-11 | 2020-10-06 | Battelle Memorial Institute | Alkoxylated bio-oil polyol compositions |
| EP2980110A1 (en) * | 2014-07-31 | 2016-02-03 | ALLNEX AUSTRIA GmbH | Aqueous polyurethane-vinyl polymer hybrid dispersions |
| SE537921C2 (sv) * | 2014-12-04 | 2015-11-24 | Perstorp Ab | Radiation curing coating composition |
| EP3350243B1 (de) * | 2015-09-16 | 2019-08-14 | Covestro Deutschland AG | Beschichtete folien mit besonders hoher hydrolysebeständigkeit und hieraus hergestellte formkörper |
| WO2017058504A1 (en) * | 2015-10-02 | 2017-04-06 | Resinate Materials Group, Inc. | High performance coatings |
| CN105349022A (zh) * | 2015-11-30 | 2016-02-24 | 上海华谊精细化工有限公司 | 一种丙烯酸改性阴离子水性氨酯油分散体及其制备和以其为基料的木器涂料 |
| EP3178860B1 (de) * | 2015-12-10 | 2018-11-28 | Covestro Deutschland AG | Oxidativ trocknende polyurethandispersionen mit einer besonders hohen chemikalienresistenz |
| CN105601880B (zh) * | 2015-12-25 | 2018-04-24 | 广州纽楷美新材料科技有限公司 | 蓖麻油基聚氨酯丙烯酸酯及制备方法和应用 |
| JP6551294B2 (ja) | 2016-04-26 | 2019-07-31 | 株式会社デンソー | 硬化性ポリウレタン系樹脂組成物を用いた電装部品 |
| CN109642114A (zh) | 2016-07-14 | 2019-04-16 | 米切尔曼公司 | 水基聚氨酯/丙烯酸酯混合分散体 |
| CN106752789B (zh) * | 2016-11-24 | 2019-10-18 | 广州富美奥涂料有限公司 | 一种pu白底漆及其制备方法 |
| ES2754595T3 (es) * | 2017-01-11 | 2020-04-20 | Hubergroup Italia | Poliuretano que es adecuado como ligante para un sistema modular de tinta de impresión |
| JP7028724B2 (ja) * | 2018-01-26 | 2022-03-02 | 大日精化工業株式会社 | 感光性ウレタン樹脂 |
| EP3793625A1 (en) | 2018-05-16 | 2021-03-24 | SurModics, Inc. | High-pressure balloon catheters and methods |
| ES2989485T3 (es) * | 2018-07-13 | 2024-11-26 | Miwon Austria Forschung Und Entw Gmbh | Poli((met)acrilatos de uretano) dispersables en agua para revestimientos curables por radiación actínica |
| WO2020012158A1 (en) * | 2018-07-13 | 2020-01-16 | Sun Chemical Corporation | Aqueous electron beam curable compositions comprising poly(alkoxylates) |
| WO2020089189A1 (en) | 2018-11-02 | 2020-05-07 | Elantas Europe Gmbh | Dual cure composition |
| CN110105578B (zh) * | 2019-04-26 | 2021-12-21 | 深圳职业技术学院 | 一种具有含硅链段的高水溶性紫外光固化水性树脂及其制备方法 |
| CN110527063A (zh) * | 2019-07-09 | 2019-12-03 | 华伦纳路新材料有限公司 | 双环戊二烯聚氨酯改性水性醇酸树脂及其制备方法 |
| CN112285273A (zh) * | 2020-11-16 | 2021-01-29 | 黄河三角洲京博化工研究院有限公司 | 一种二羟甲基丙酸羟值含量的检测方法 |
| CN115364272B (zh) * | 2022-09-09 | 2023-08-08 | 江西博恩锐尔生物科技有限公司 | 柔软度可调的血管栓塞剂及其制备方法 |
| WO2024126304A1 (en) | 2022-12-15 | 2024-06-20 | Basf Se | Aqueous compositions comprising (meth)acrylate group carrying polyurethane which yield cross-linked layers of high hardness and good adhesion |
| CN116285825B (zh) * | 2023-01-06 | 2024-03-19 | 广东莱尔新材料科技股份有限公司 | 一种水性聚酯热熔胶涂布液及其制备方法 |
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| DE4405208A1 (de) | 1994-02-18 | 1995-08-24 | Wolff Walsrode Ag | Polymerdispersion |
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| DE19800286A1 (de) | 1998-01-07 | 1999-07-08 | Bayer Ag | Verwendung spezieller Isocyanate zur Herstellung wäßriger PUR-Überzüge |
| DE19810793A1 (de) | 1998-03-12 | 1999-09-16 | Basf Ag | Härtbares Polyurethanpolymerisat, Dispersion auf Basis dieses Polymerisats, Verfahren zu ihrer Herstellung und ihre Verwendung |
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| JP2001033960A (ja) * | 1999-07-16 | 2001-02-09 | Kansai Paint Co Ltd | フォトレジスト用感光性樹脂組成物及びレジストパターン形成方法 |
| DE10206565A1 (de) | 2002-02-18 | 2003-08-21 | Bayer Ag | Wässrige Beschichtungsmittel auf Basis von Epoxybuten-Polyethern |
| EP1485438A1 (de) * | 2002-02-18 | 2004-12-15 | Bayer MaterialScience AG | Wässrige beschichtungsmittel auf basis von epoxybuten-polyethern |
| DE10226932A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Strahlenhärtende Beschichtungsmittel |
| AT412721B (de) | 2003-08-27 | 2005-06-27 | Surface Specialties Austria | Bindemittel für strahlenhärtbare wässrige lacke |
| US20050238815A1 (en) * | 2004-04-27 | 2005-10-27 | Dvorchak Michael J | UV curable coating composition |
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| WO2006089935A1 (de) | 2005-02-24 | 2006-08-31 | Basf Aktiengesellschaft | Strahlungshärtbare wässrige polyurethandispersionen |
| EP1845143A1 (en) * | 2006-04-14 | 2007-10-17 | Cytec Surface Specialties, S.A. | Aqueous radiation curable polyurethane compositions |
| DE102006049764A1 (de) | 2006-10-21 | 2008-04-24 | Bayer Materialscience Ag | UV-härtbare Polyurethan-Dispersionen |
| DE102006054237A1 (de) | 2006-11-17 | 2008-05-21 | Bayer Materialscience Ag | Polyurethan-modifizierte Alkydharzdispersionen |
| DE102007006492A1 (de) * | 2007-02-09 | 2008-08-14 | Bayer Materialscience Ag | UV-härtbare Dispersionen auf Basis von Polyisocyanaten |
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| DE102009008949A1 (de) * | 2009-02-13 | 2010-08-19 | Bayer Materialscience Ag | Wässrige Beschichtungssysteme auf Basis physikalisch trocknender Urethanacrylate |
| SI2316867T1 (sl) * | 2009-10-31 | 2012-09-28 | Bayer Materialscience Ag | Vodne poliuretanske disperzije, brez kositra |
-
2010
- 2010-03-02 DE DE102010009896A patent/DE102010009896A1/de not_active Withdrawn
-
2011
- 2011-02-25 AU AU2011223057A patent/AU2011223057A1/en not_active Abandoned
- 2011-02-25 DK DK11704638.3T patent/DK2542600T3/da active
- 2011-02-25 CN CN201180011756.0A patent/CN102812062B/zh active Active
- 2011-02-25 BR BR112012022047A patent/BR112012022047A2/pt not_active IP Right Cessation
- 2011-02-25 RU RU2012141623/04A patent/RU2012141623A/ru not_active Application Discontinuation
- 2011-02-25 WO PCT/EP2011/052783 patent/WO2011107398A1/de not_active Ceased
- 2011-02-25 EP EP11704638.3A patent/EP2542600B1/de active Active
- 2011-02-25 JP JP2012555368A patent/JP2013521357A/ja active Pending
- 2011-02-25 MX MX2012009963A patent/MX2012009963A/es unknown
- 2011-02-25 CA CA2791557A patent/CA2791557A1/en not_active Abandoned
- 2011-02-25 KR KR1020127022804A patent/KR101816328B1/ko not_active Expired - Fee Related
- 2011-02-25 US US13/580,287 patent/US9676894B2/en active Active
- 2011-02-25 ES ES11704638.3T patent/ES2466002T3/es active Active
- 2011-03-01 TW TW100106589A patent/TW201202289A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2466002T3 (es) | 2014-06-09 |
| HK1175795A1 (en) | 2013-07-12 |
| CN102812062A (zh) | 2012-12-05 |
| DE102010009896A1 (de) | 2011-09-08 |
| TW201202289A (en) | 2012-01-16 |
| JP2013521357A (ja) | 2013-06-10 |
| EP2542600B1 (de) | 2014-03-26 |
| US20130041072A1 (en) | 2013-02-14 |
| KR20130010113A (ko) | 2013-01-25 |
| EP2542600A1 (de) | 2013-01-09 |
| CN102812062B (zh) | 2015-09-30 |
| AU2011223057A1 (en) | 2012-09-20 |
| KR101816328B1 (ko) | 2018-01-08 |
| US9676894B2 (en) | 2017-06-13 |
| RU2012141623A (ru) | 2014-04-10 |
| DK2542600T3 (da) | 2014-06-23 |
| MX2012009963A (es) | 2012-09-21 |
| WO2011107398A1 (de) | 2011-09-09 |
| BR112012022047A2 (pt) | 2017-10-31 |
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