CA2017951C - Catheter expansible en elastomere thermoplastique de polyetherurethane hydrophile - Google Patents

Catheter expansible en elastomere thermoplastique de polyetherurethane hydrophile

Info

Publication number: CA2017951C
Authority: CA; Canada
Prior art keywords: catheter; glycol; agent; tubing; diisocyanate
Prior art date: 1989-06-21
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

Application number

CA 2017951

Other languages

English (en)

Other versions

CA2017951A1 (fr

Inventor

Mutlu Karakelle

Donald D. Solomon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kendall Co

Original Assignee

Kendall Co

Priority date (The priority date 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 date listed.)

1989-06-21

Filing date

1990-05-31

Publication date

1996-02-20

1990-05-31 Application filed by Kendall Co filed Critical Kendall Co

1990-12-22 Publication of CA2017951A1 publication Critical patent/CA2017951A1/fr

1996-02-20 Application granted granted Critical

1996-02-20 Publication of CA2017951C publication Critical patent/CA2017951C/fr

2010-05-31 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920002725 thermoplastic elastomer Polymers 0.000 title description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 34
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 14
229920002635 polyurethane Polymers 0.000 claims abstract description 14
239000004814 polyurethane Substances 0.000 claims abstract description 14
239000004970 Chain extender Substances 0.000 claims abstract description 11
125000005442 diisocyanate group Chemical group 0.000 claims abstract description 11
239000007788 liquid Substances 0.000 claims abstract description 11
229960005475 antiinfective agent Drugs 0.000 claims abstract description 9
239000004599 antimicrobial Substances 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 9
239000003527 fibrinolytic agent Substances 0.000 claims abstract description 9
229920001169 thermoplastic Polymers 0.000 claims abstract description 7
239000004416 thermosoftening plastic Substances 0.000 claims abstract description 7
229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 6
239000000155 melt Substances 0.000 claims abstract 4
239000000203 mixture Substances 0.000 claims description 17
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 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
229920000642 polymer Polymers 0.000 claims description 6
229920001296 polysiloxane Polymers 0.000 claims description 6
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
229920001499 Heparinoid Polymers 0.000 claims description 3
239000002554 heparinoid Substances 0.000 claims description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
229920000151 polyglycol Polymers 0.000 claims description 3
239000010695 polyglycol Substances 0.000 claims description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
CTNICFBTUIFPOE-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)ethane-1,1-diol Chemical compound OC(O)COC1=CC=C(O)C=C1 CTNICFBTUIFPOE-UHFFFAOYSA-N 0.000 claims description 2
GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
108010023197 Streptokinase Proteins 0.000 claims description 2
108090000373 Tissue Plasminogen Activator Proteins 0.000 claims description 2
102000003978 Tissue Plasminogen Activator Human genes 0.000 claims description 2
108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 2
102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims description 2
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 claims description 2
229960003260 chlorhexidine Drugs 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
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 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
229920001451 polypropylene glycol Polymers 0.000 claims description 2
229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
235000013772 propylene glycol Nutrition 0.000 claims description 2
150000003180 prostaglandins Chemical class 0.000 claims description 2
229960003600 silver sulfadiazine Drugs 0.000 claims description 2
UEJSSZHHYBHCEL-UHFFFAOYSA-N silver(1+) sulfadiazinate Chemical compound [Ag+].C1=CC(N)=CC=C1S(=O)(=O)[N-]C1=NC=CC=N1 UEJSSZHHYBHCEL-UHFFFAOYSA-N 0.000 claims description 2
229960005202 streptokinase Drugs 0.000 claims description 2
229960000187 tissue plasminogen activator Drugs 0.000 claims description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
229960005356 urokinase Drugs 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 claims 1
238000012662 bulk polymerization Methods 0.000 abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000000034 method Methods 0.000 description 10
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 8
238000003780 insertion Methods 0.000 description 7
230000037431 insertion Effects 0.000 description 7
238000001125 extrusion Methods 0.000 description 6
229920000669 heparin Polymers 0.000 description 6
229960002897 heparin Drugs 0.000 description 6
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
150000002334 glycols Chemical class 0.000 description 5
230000008961 swelling Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
210000001124 body fluid Anatomy 0.000 description 3
239000010839 body fluid Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004386 diacrylate group Chemical group 0.000 description 2
150000002009 diols Chemical group 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229940025770 heparinoids Drugs 0.000 description 2
239000000017 hydrogel Substances 0.000 description 2
229920001477 hydrophilic polymer Polymers 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
DXTCRSXRMZSEQP-UHFFFAOYSA-N 2-benzofuran-1,3-dione;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2C(=O)OC(=O)C2=C1 DXTCRSXRMZSEQP-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229960001927 cetylpyridinium chloride Drugs 0.000 description 1
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000012633 leachable Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010128 melt processing Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
-1 most preferably Chemical compound 0.000 description 1
SVBAPZTYWZGPKN-UHFFFAOYSA-N n-methyldodecan-1-amine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCNC SVBAPZTYWZGPKN-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003839 salts Chemical group 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000002352 surface water Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
238000004448 titration Methods 0.000 description 1
SBHRWOBHKASWGU-UHFFFAOYSA-M tridodecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC SBHRWOBHKASWGU-UHFFFAOYSA-M 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1

Landscapes

Materials For Medical Uses (AREA)
Polyurethanes Or Polyureas (AREA)

CA 2017951 1989-06-21 1990-05-31 Catheter expansible en elastomere thermoplastique de polyetherurethane hydrophile Expired - Fee Related CA2017951C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US36948489A	1989-06-21	1989-06-21
US369,484		1989-06-21

Publications (2)

Publication Number	Publication Date
CA2017951A1 CA2017951A1 (fr)	1990-12-22
CA2017951C true CA2017951C (fr)	1996-02-20

Family

ID=23455672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2017951 Expired - Fee Related CA2017951C (fr)	1989-06-21	1990-05-31	Catheter expansible en elastomere thermoplastique de polyetherurethane hydrophile

Country Status (3)

Country	Link
JP (1)	JPH0382473A (fr)
CA (1)	CA2017951C (fr)
IE (1)	IE902199A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4570708B2 (ja) *	1998-06-02	2010-10-27	テルモ株式会社	分子量の異なる複数のポリグリコールを含有するポリウレタン樹脂からなる留置カテーテル
JP4691398B2 (ja) *	2005-06-02	2011-06-01	株式会社典雅	射精促進装置
WO2013030148A1 (fr)	2011-08-29	2013-03-07	Bayer Intellectual Property Gmbh	Polyuréthanes thermoplastiques hydrophiles et utilisation desdits polyuréthanes thermoplastiques hydrophiles dans la technique médicale

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1192462A (fr) *	1982-01-27	1985-08-27	Avvari Rangaswamy	Eponge d'epistaxie
US4676975A (en) *	1984-12-07	1987-06-30	Becton, Dickinson And Company	Thermoplastic polyurethane anticoagulant alloy coating
US4781703A (en) *	1985-10-17	1988-11-01	Menlo Care, Inc.	Catheter assembly

1990
- 1990-05-31 CA CA 2017951 patent/CA2017951C/fr not_active Expired - Fee Related
- 1990-06-18 IE IE219990A patent/IE902199A1/en not_active IP Right Cessation
- 1990-06-21 JP JP2163973A patent/JPH0382473A/ja active Pending

Also Published As

Publication number	Publication date
IE902199A1 (en)	1991-01-02
JPH0382473A (ja)	1991-04-08
CA2017951A1 (fr)	1990-12-22
IE902199L (en)	1990-12-21

Legal Events

Date	Code	Title	Description
1990-06-19	EEER	Examination request
1998-06-01	MKLA	Lapsed

Publication	Publication Date	Title
US5061254A (en)	1991-10-29	Thermoplastic elastomeric hydrophilic polyetherurethane expandable catheter
EP0472413B1 (fr)	1996-07-31	Cathéter expansible ayant une surface hydrophobique
AU661183B2 (en)	1995-07-13	Thermoplastic polyurethane blends
US5453099A (en)	1995-09-26	Catheter tubing of controlled in vivo softening
EP0595500B1 (fr)	1999-08-18	Polyuréthane non-gonflable, ramollissant par contact avec un liquide
EP0448886B1 (fr)	1995-05-31	Tube pour cathéter à ramollissement contrôlé in vivo
US5015238A (en)	1991-05-14	Expandable obturator and catheter assembly including same
EP0496305A2 (fr)	1992-07-29	Procédé pour appliquer un revêtement glissant sur un article
US5250649A (en)	1993-10-05	Melt processable polyurethaneurea copolymers and method for their preparation
CA2017951C (fr)	1996-02-20	Catheter expansible en elastomere thermoplastique de polyetherurethane hydrophile
CA2018244C (fr)	1996-06-04	Obturateur gonflable et catheter le comprenant
IE902200A1 (en)	1991-10-09	Thermoplastic elastomeric hydrophilic polyetherurethane¹expandable catheter