CN106967206A - 亲水润滑医用聚氨酯材料及其制备方法和应用 - Google Patents
亲水润滑医用聚氨酯材料及其制备方法和应用 Download PDFInfo
- Publication number
- CN106967206A CN106967206A CN201710237623.4A CN201710237623A CN106967206A CN 106967206 A CN106967206 A CN 106967206A CN 201710237623 A CN201710237623 A CN 201710237623A CN 106967206 A CN106967206 A CN 106967206A
- Authority
- CN
- China
- Prior art keywords
- diisocyanate
- hydroxy
- medical
- hydrophilic lubrication
- polyurethane material
- 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.)
- Granted
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 129
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 126
- 239000000463 material Substances 0.000 title claims abstract description 109
- 238000005461 lubrication Methods 0.000 title claims abstract description 86
- 238000002360 preparation method Methods 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 claims abstract description 109
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 104
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000002994 raw material Substances 0.000 claims abstract description 25
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 15
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 71
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 62
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 45
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 235000011187 glycerol Nutrition 0.000 claims description 31
- 229920000728 polyester Polymers 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- 229920001661 Chitosan Polymers 0.000 claims description 23
- -1 trihydroxy methyl Chemical group 0.000 claims description 22
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 21
- 229910021529 ammonia Inorganic materials 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 21
- 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 21
- 238000002156 mixing Methods 0.000 claims description 19
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 claims description 11
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 9
- 239000007822 coupling agent Substances 0.000 claims description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical class CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 6
- 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 claims description 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920002545 silicone oil Polymers 0.000 claims description 5
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 claims description 3
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 claims description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 3
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical class CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 3
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 claims description 3
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- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
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- 150000001335 aliphatic alkanes Chemical class 0.000 claims 3
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims 1
- 239000008367 deionised water Substances 0.000 claims 1
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- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
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- LMVLVUPTDRWATB-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-ol Chemical compound CO[Si](C)(OC)CCCO LMVLVUPTDRWATB-UHFFFAOYSA-N 0.000 description 1
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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Cited By (4)
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CN107522879A (zh) * | 2017-10-12 | 2017-12-29 | 黄山泰尔新材料有限公司 | 一种肤感聚氨酯微球及其制备方法、应用 |
CN111303618A (zh) * | 2019-12-20 | 2020-06-19 | 山东一诺威聚氨酯股份有限公司 | 有机硅改性tpu医用导管及其制备方法 |
CN113150239A (zh) * | 2021-04-09 | 2021-07-23 | 华南理工大学 | 一种固化时长可控的医用聚氨酯粘合剂的制备方法 |
CN115337472A (zh) * | 2022-08-30 | 2022-11-15 | 中国科学院长春应用化学研究所 | 一种涂层组合物、涂层及其制备方法、医疗器械 |
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FR3119776B1 (fr) * | 2021-02-12 | 2023-04-28 | Braun Medical | Kit de sonde urinaire |
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CN1869094A (zh) * | 2006-05-16 | 2006-11-29 | 南京大学 | 壳聚糖改性水性聚氨酯弹性体的制备方法 |
CN101343346A (zh) * | 2008-09-05 | 2009-01-14 | 寇世杰 | 壳聚糖聚氨酯材料及其制备方法 |
CN101497698A (zh) * | 2009-01-22 | 2009-08-05 | 南京大学 | 壳聚糖-聚氨酯离子复合物弹性体材料的制备方法 |
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CN1554687A (zh) * | 2003-12-26 | 2004-12-15 | 华南理工大学 | 亲水性热塑性聚氨酯弹性体及其制备方法和应用 |
CN1869094A (zh) * | 2006-05-16 | 2006-11-29 | 南京大学 | 壳聚糖改性水性聚氨酯弹性体的制备方法 |
CN101343346A (zh) * | 2008-09-05 | 2009-01-14 | 寇世杰 | 壳聚糖聚氨酯材料及其制备方法 |
CN101497698A (zh) * | 2009-01-22 | 2009-08-05 | 南京大学 | 壳聚糖-聚氨酯离子复合物弹性体材料的制备方法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107522879A (zh) * | 2017-10-12 | 2017-12-29 | 黄山泰尔新材料有限公司 | 一种肤感聚氨酯微球及其制备方法、应用 |
CN107522879B (zh) * | 2017-10-12 | 2020-11-06 | 黄山泰尔新材料有限公司 | 一种肤感聚氨酯微球及其制备方法、应用 |
CN111303618A (zh) * | 2019-12-20 | 2020-06-19 | 山东一诺威聚氨酯股份有限公司 | 有机硅改性tpu医用导管及其制备方法 |
CN113150239A (zh) * | 2021-04-09 | 2021-07-23 | 华南理工大学 | 一种固化时长可控的医用聚氨酯粘合剂的制备方法 |
CN115337472A (zh) * | 2022-08-30 | 2022-11-15 | 中国科学院长春应用化学研究所 | 一种涂层组合物、涂层及其制备方法、医疗器械 |
CN115337472B (zh) * | 2022-08-30 | 2023-08-29 | 中国科学院长春应用化学研究所 | 一种涂层组合物、涂层及其制备方法、医疗器械 |
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