DE69615705T2 - Carbonsäure-funktionalität aufweisende polyurethan-polymere sowie ihre mischungen verwendet in magnetischen aufzeichnungsmedien - Google Patents
Carbonsäure-funktionalität aufweisende polyurethan-polymere sowie ihre mischungen verwendet in magnetischen aufzeichnungsmedienInfo
- Publication number
- DE69615705T2 DE69615705T2 DE69615705T DE69615705T DE69615705T2 DE 69615705 T2 DE69615705 T2 DE 69615705T2 DE 69615705 T DE69615705 T DE 69615705T DE 69615705 T DE69615705 T DE 69615705T DE 69615705 T2 DE69615705 T2 DE 69615705T2
- Authority
- DE
- Germany
- Prior art keywords
- quaternary ammonium
- groups
- isocyanate
- polyols
- carboxylic acid
- 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 - Fee Related
Links
- 239000004814 polyurethane Substances 0.000 title claims description 142
- 229920002635 polyurethane Polymers 0.000 title claims description 142
- 229920000642 polymer Polymers 0.000 title claims description 91
- 239000000203 mixture Substances 0.000 title claims description 86
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical group OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 104
- 239000006185 dispersion Substances 0.000 claims description 92
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 84
- 229920005862 polyol Polymers 0.000 claims description 71
- 239000000049 pigment Substances 0.000 claims description 70
- 238000000576 coating method Methods 0.000 claims description 60
- 150000003077 polyols Chemical class 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 150000002009 diols Chemical class 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 48
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 48
- 239000005056 polyisocyanate Substances 0.000 claims description 37
- 229920001228 polyisocyanate Polymers 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 239000000178 monomer Substances 0.000 claims description 34
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 34
- -1 quaternary ammonium polyols Chemical class 0.000 claims description 33
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 28
- 239000011248 coating agent Substances 0.000 claims description 28
- 229920002554 vinyl polymer Polymers 0.000 claims description 28
- 229920006163 vinyl copolymer Polymers 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 14
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229960003237 betaine Drugs 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- XFOZBWSTIQRFQW-UHFFFAOYSA-M benzyl-dimethyl-prop-2-enylazanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC1=CC=CC=C1 XFOZBWSTIQRFQW-UHFFFAOYSA-M 0.000 claims description 2
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 claims description 2
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 206
- 238000001723 curing Methods 0.000 description 47
- 239000011230 binding agent Substances 0.000 description 36
- 239000000463 material Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- 239000012948 isocyanate Substances 0.000 description 28
- 150000002513 isocyanates Chemical class 0.000 description 28
- 238000002360 preparation method Methods 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 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 22
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 239000012975 dibutyltin dilaurate Substances 0.000 description 16
- 239000002270 dispersing agent Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000002329 infrared spectrum Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 229920001610 polycaprolactone Polymers 0.000 description 12
- 239000004632 polycaprolactone Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000011068 loading method Methods 0.000 description 11
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 9
- 238000003801 milling Methods 0.000 description 9
- 239000000314 lubricant Substances 0.000 description 8
- 239000006249 magnetic particle Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000004072 triols Chemical class 0.000 description 8
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000518 rheometry Methods 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 6
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000010533 azeotropic distillation Methods 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 150000004658 ketimines Chemical class 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
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- 239000011347 resin Substances 0.000 description 5
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000010724 Wisteria floribunda Nutrition 0.000 description 4
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
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- 239000000194 fatty acid Substances 0.000 description 4
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- 239000012530 fluid Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
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Landscapes
- Chemical & Material Sciences (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/576,616 US5759666A (en) | 1995-12-21 | 1995-12-21 | Carboxylic acid functional polyurethane polymers and blends thereof used in magnetic recording media |
| PCT/US1996/018355 WO1997023526A1 (en) | 1995-12-21 | 1996-11-11 | Carboxylic acid functional polyurethane polymers and blends thereof used in magnetic recording media |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69615705D1 DE69615705D1 (de) | 2001-11-08 |
| DE69615705T2 true DE69615705T2 (de) | 2002-08-08 |
Family
ID=24305195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69615705T Expired - Fee Related DE69615705T2 (de) | 1995-12-21 | 1996-11-11 | Carbonsäure-funktionalität aufweisende polyurethan-polymere sowie ihre mischungen verwendet in magnetischen aufzeichnungsmedien |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US5759666A (enExample) |
| EP (1) | EP0869981B1 (enExample) |
| JP (1) | JP2000502388A (enExample) |
| KR (1) | KR19990072200A (enExample) |
| DE (1) | DE69615705T2 (enExample) |
| WO (1) | WO1997023526A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5759666A (en) * | 1995-12-21 | 1998-06-02 | Minnesota Mining And Manufacturing Company | Carboxylic acid functional polyurethane polymers and blends thereof used in magnetic recording media |
| US6322548B1 (en) | 1995-05-10 | 2001-11-27 | Eclipse Surgical Technologies | Delivery catheter system for heart chamber |
| JPH11131045A (ja) * | 1997-10-28 | 1999-05-18 | Nippon Polyurethane Ind Co Ltd | ラミネート用接着剤 |
| JP2000239308A (ja) * | 1999-02-24 | 2000-09-05 | Soken Chem & Eng Co Ltd | アクリル系重合体、硬化性組成物、硬化体およびこれらの用途 |
| KR100586132B1 (ko) * | 1999-04-23 | 2006-06-02 | 닛폰 폴리우레탄 고교 가부시키가이샤 | 라미네이트용 접착제 |
| RU2234912C2 (ru) * | 2000-04-13 | 2004-08-27 | Нэшнл Старч Энд Кемикал Инвестмент Холдинг Корпорейшн | Косметическая композиция на основе смолы и ее применение в косметике |
| RU2234911C2 (ru) * | 2000-04-13 | 2004-08-27 | Нэшнл Старч Энд Кемикал Инвестмент Холдинг Корпорейшн | Косметическая композиция на основе смолы и ее применение в косметике |
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-
1995
- 1995-12-21 US US08/576,616 patent/US5759666A/en not_active Expired - Fee Related
-
1996
- 1996-11-11 KR KR1019980704567A patent/KR19990072200A/ko not_active Ceased
- 1996-11-11 DE DE69615705T patent/DE69615705T2/de not_active Expired - Fee Related
- 1996-11-11 JP JP9523635A patent/JP2000502388A/ja not_active Ceased
- 1996-11-11 EP EP96939720A patent/EP0869981B1/en not_active Expired - Lifetime
- 1996-11-11 WO PCT/US1996/018355 patent/WO1997023526A1/en not_active Ceased
-
1997
- 1997-08-28 US US08/924,046 patent/US5874502A/en not_active Expired - Fee Related
-
1998
- 1998-08-10 US US09/131,520 patent/US6139966A/en not_active Expired - Fee Related
-
2002
- 2002-04-08 US US10/118,143 patent/US20030045630A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0869981B1 (en) | 2001-10-04 |
| US20030045630A1 (en) | 2003-03-06 |
| JP2000502388A (ja) | 2000-02-29 |
| US5759666A (en) | 1998-06-02 |
| US6139966A (en) | 2000-10-31 |
| KR19990072200A (ko) | 1999-09-27 |
| EP0869981A1 (en) | 1998-10-14 |
| US5874502A (en) | 1999-02-23 |
| WO1997023526A1 (en) | 1997-07-03 |
| DE69615705D1 (de) | 2001-11-08 |
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