DE2931044C2 - - Google Patents
Info
- Publication number
- DE2931044C2 DE2931044C2 DE2931044A DE2931044A DE2931044C2 DE 2931044 C2 DE2931044 C2 DE 2931044C2 DE 2931044 A DE2931044 A DE 2931044A DE 2931044 A DE2931044 A DE 2931044A DE 2931044 C2 DE2931044 C2 DE 2931044C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- prepolymer
- dispersion
- carboxylic acid
- groups
- 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.)
- Expired - Lifetime
Links
- 239000006185 dispersion Substances 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 150000002009 diols Chemical class 0.000 claims description 27
- 229920002635 polyurethane Polymers 0.000 claims description 22
- 239000004814 polyurethane Substances 0.000 claims description 22
- -1 hydrogen compound Chemical class 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- 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 17
- 125000005442 diisocyanate group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 13
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000003077 polyols Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000000499 gel Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000004970 Chain extender Substances 0.000 description 11
- 238000004364 calculation method Methods 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 230000031700 light absorption Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 230000003381 solubilizing effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 150000004072 triols Chemical group 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000002649 leather substitute Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 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 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000010518 undesired secondary reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/947,544 US4554308A (en) | 1978-10-02 | 1978-10-02 | Crosslinked polyurethane dispersions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2931044A1 DE2931044A1 (de) | 1980-04-17 |
| DE2931044C2 true DE2931044C2 (en, 2012) | 1991-07-25 |
Family
ID=25486292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792931044 Granted DE2931044A1 (de) | 1978-10-02 | 1979-07-31 | Waessrige ionische dispersion von vernetzten polyurethanteilchen |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4554308A (en, 2012) |
| JP (2) | JPS5548244A (en, 2012) |
| AT (1) | AT379819B (en, 2012) |
| AU (1) | AU532058B2 (en, 2012) |
| BE (1) | BE878962A (en, 2012) |
| CA (1) | CA1154191A (en, 2012) |
| CH (1) | CH648579A5 (en, 2012) |
| CS (1) | CS212711B2 (en, 2012) |
| DE (1) | DE2931044A1 (en, 2012) |
| DK (1) | DK160767C (en, 2012) |
| ES (1) | ES482174A1 (en, 2012) |
| FI (1) | FI66191C (en, 2012) |
| FR (1) | FR2438069B1 (en, 2012) |
| GB (1) | GB2031920B (en, 2012) |
| IT (1) | IT1120520B (en, 2012) |
| LU (1) | LU81722A1 (en, 2012) |
| NL (1) | NL187400C (en, 2012) |
| NO (1) | NO153854C (en, 2012) |
| NZ (1) | NZ191498A (en, 2012) |
| PL (1) | PL128445B1 (en, 2012) |
| SE (1) | SE445925B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220372323A1 (en) * | 2019-10-09 | 2022-11-24 | Lubrizol Advanced Materials, Inc. | Ink-receptive coatings for printing on absorbing substrates |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4332710A (en) * | 1981-02-17 | 1982-06-01 | Norwood Industries, Inc. | Thermal coagulation of polyurethane dispersions |
| DE3233605A1 (de) * | 1982-09-10 | 1984-03-15 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von vernetzten polyurethan-ionomerdispersionen |
| DE3421257C2 (de) * | 1984-06-07 | 1986-07-10 | Zeller + Gmelin GmbH & Co, 7332 Eislingen | Einkomponentenformulierung zur Entklebung, Ausfällung und Koagulierung von Steinschlag- und Unterbodenschutz auf Basis von Wachsen, wachsähnlichen Kunststoffen und Kunststoffdispersionen sowie von Kunstharzlacken in Naßabscheidern von Spritzlackieranlagen unter Erzielung eines aufschwimmenden Lackschlamms und deren Verwendung |
| US4657964A (en) * | 1985-07-03 | 1987-04-14 | Ici Americas Inc. | Aqueous-based urethane coating compositions |
| DE3606513C2 (de) * | 1986-02-28 | 1998-05-07 | Basf Coatings Ag | Dispersionen von vernetzten Polymermikroteilchen in wäßrigen Medien und Verfahren zur Herstellung dieser Dispersionen |
| US4690953A (en) * | 1986-03-11 | 1987-09-01 | Seton Company | Method of frothing aqueous ionic polyurethane dispersions and products produced therefrom |
| IT1213441B (it) * | 1986-12-30 | 1989-12-20 | Ausimont Spa | Dispersioni acquose di poliuretani e fluorurati e loro impiego per spalmature tessili. |
| DE3704350A1 (de) * | 1987-02-12 | 1988-08-25 | Henkel Kgaa | Wasserverduennbare ueberzugsmittel |
| US4780523A (en) * | 1987-03-02 | 1988-10-25 | The Goodyear Tire & Rubber Company | Meta-tetramethyl xylene diamine polyurethane compositions and process of making the same |
| US4937283A (en) * | 1987-03-02 | 1990-06-26 | The Goodyear Tire & Rubber Company | Meta-tetramethyl xylene diamine polyurethane compositions and process of making the same |
| EP0296098A3 (en) * | 1987-06-16 | 1989-08-23 | W.R. Grace & Co.-Conn. | Crosslinked polyurethane emulsion, process and prepolymer for its production and process for forming coatings from said emulsion |
| DE3735587A1 (de) * | 1987-10-21 | 1989-05-11 | Bayer Ag | Verfahren zur herstellung von waessrigen polyurethan-polyharnstoffdispersionen |
| US4822685A (en) * | 1987-12-10 | 1989-04-18 | Ppg Industries, Inc. | Method for preparing multi-layered coated articles and the coated articles prepared by the method |
| US4895894A (en) * | 1988-05-31 | 1990-01-23 | The Dow Chemical Company | Modulus modification of water borne polyurethane-ureas |
| US4956438A (en) * | 1989-02-08 | 1990-09-11 | The Dow Chemical Company | Bulk polyurethane ionomers |
| US5122560A (en) * | 1989-12-12 | 1992-06-16 | E. I. Du Pont De Nemours And Company | Coating composition of polyesterurethane and polyisocyanate crosslinking agent |
| US5139854A (en) * | 1989-12-12 | 1992-08-18 | E. I. Du Pont De Nemours And Company | Coating composition of polyesterurethane and polyisocyanate crosslinking agent in laminate |
| WO1992018558A1 (en) * | 1991-04-12 | 1992-10-29 | Robert M. Evans Associates, Inc. | Polyurethane-containing sealant and coating |
| US6106813A (en) | 1993-08-04 | 2000-08-22 | L'oreal | Polyester polyurethanes, process for preparing them, produced from the said polyester polyurethanes and their use in cosmetic compositions |
| US6160076A (en) * | 1994-06-24 | 2000-12-12 | Arco Chemical Technology, L. P. | Cross-linked aqueous polyurethane dispersions containing dimer/trimer |
| US6133399A (en) * | 1994-06-24 | 2000-10-17 | Arco Chemical Technology, L.P. | Aqueous polyurethane dispersions containing dimer/trimer |
| US6239209B1 (en) | 1999-02-23 | 2001-05-29 | Reichhold, Inc. | Air curable water-borne urethane-acrylic hybrids |
| ATE233792T1 (de) * | 1999-02-25 | 2003-03-15 | Bayer Ag | Wässrige sperrschicht auf basis von polyurethan- dispersionen |
| US6635706B1 (en) | 1999-06-23 | 2003-10-21 | Reichhold, Inc. | Urethane-acrylic hybrid polymer dispersion |
| CN101959914B (zh) * | 2007-12-26 | 2014-02-12 | 陶氏环球技术有限责任公司 | 聚氨酯分散体和从该分散体制得的涂层 |
| US8142857B2 (en) * | 2008-12-08 | 2012-03-27 | Chung-Shan Institute Of Science And Technology, Armaments Bureau, Ministry Of National Defense | Compound and method for producing the same |
| US20110247864A1 (en) * | 2008-12-19 | 2011-10-13 | Showa Denko K.K. | Thermosetting ink composition |
| CN117535019B (zh) * | 2023-10-26 | 2024-12-03 | 阿梓萨科技(深圳)有限公司 | 用于柔性电子器件永久支撑膜的pu防护膜的制备方法 |
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| DE1495745C3 (de) * | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices |
| DE1570615C3 (de) * | 1965-10-16 | 1975-05-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von dispergierbaren Polyurethanen |
| FR1521170A (fr) * | 1966-04-28 | 1968-04-12 | Bayer Ag | Procédé de préparation de dispersions aqueuses de produits de polyaddition réticulés présentant des groupes urée |
| US3412054A (en) * | 1966-10-31 | 1968-11-19 | Union Carbide Corp | Water-dilutable polyurethanes |
| US3870684A (en) * | 1970-04-29 | 1975-03-11 | Bayer Ag | Preparation of cross-linked particles of polyurethane or polyurea containing ionic groups |
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| DE2325825C3 (de) * | 1973-05-22 | 1980-07-03 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung vonvemetetel1· licht- und lagerstabilen, wäßrigen Polyurethandispersionen |
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| AU502343B2 (en) * | 1975-06-02 | 1979-07-19 | Ppg Industries, Inc. | Aqueous dispersion of a non-gelled polyurethane |
| JPS5216595A (en) * | 1975-07-31 | 1977-02-07 | Kao Corp | Process for preparing anionic polyurethane emulsions |
| DE2551094A1 (de) * | 1975-11-14 | 1977-05-26 | Bayer Ag | Verfahren zur herstellung von in wasser dispergierbaren polyurethanen |
| US4147679A (en) * | 1976-06-02 | 1979-04-03 | Ppg Industries, Inc. | Water-reduced urethane coating compositions |
| CA1131376A (en) * | 1976-10-04 | 1982-09-07 | David G. Hangauer, Jr. | Aqueous urea-urethane dispersions |
| JPS5385894A (en) * | 1977-01-06 | 1978-07-28 | Dainichi Seika Kogyo Kk | Aqueous dispersion |
| AU3364078A (en) * | 1977-02-28 | 1979-09-06 | Textron Inc | Aqueous dispersion of urea-urethane polymers |
| US4387181A (en) * | 1980-04-09 | 1983-06-07 | Textron, Inc. | Polymer compositions and manufacture |
-
1978
- 1978-10-02 US US05/947,544 patent/US4554308A/en not_active Expired - Lifetime
-
1979
- 1979-04-27 JP JP5159479A patent/JPS5548244A/ja active Granted
- 1979-07-04 ES ES482174A patent/ES482174A1/es not_active Expired
- 1979-07-31 DE DE19792931044 patent/DE2931044A1/de active Granted
- 1979-08-17 IT IT50057/79A patent/IT1120520B/it active
- 1979-09-03 AU AU50511/79A patent/AU532058B2/en not_active Ceased
- 1979-09-07 NZ NZ191498A patent/NZ191498A/xx unknown
- 1979-09-07 AT AT0592479A patent/AT379819B/de not_active IP Right Cessation
- 1979-09-19 FI FI792909A patent/FI66191C/fi not_active IP Right Cessation
- 1979-09-21 GB GB7932889A patent/GB2031920B/en not_active Expired
- 1979-09-24 BE BE0/197282A patent/BE878962A/fr not_active IP Right Cessation
- 1979-09-25 LU LU81722A patent/LU81722A1/fr unknown
- 1979-09-29 PL PL1979218627A patent/PL128445B1/pl unknown
- 1979-10-01 NL NLAANVRAGE7907288,A patent/NL187400C/xx not_active IP Right Cessation
- 1979-10-01 SE SE7908109A patent/SE445925B/sv not_active IP Right Cessation
- 1979-10-01 CA CA000336739A patent/CA1154191A/en not_active Expired
- 1979-10-01 DK DK410979A patent/DK160767C/da not_active IP Right Cessation
- 1979-10-01 FR FR7924434A patent/FR2438069B1/fr not_active Expired
- 1979-10-01 CH CH8807/79A patent/CH648579A5/de not_active IP Right Cessation
- 1979-10-01 CS CS796650A patent/CS212711B2/cs unknown
- 1979-10-02 NO NO793157A patent/NO153854C/no unknown
-
1984
- 1984-06-27 JP JP59131184A patent/JPS60137919A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220372323A1 (en) * | 2019-10-09 | 2022-11-24 | Lubrizol Advanced Materials, Inc. | Ink-receptive coatings for printing on absorbing substrates |
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