IP Library Granted Patent US 12,465,892
Granted Patent B2
US 12,465,892 · App. 18/239,352 · Granted Nov 11, 2025

Method for evaluating covering state of silicone compound

Inventors: Takeshi Sato (Kanagawa, JP); Renjo Takama (Kanagawa, JP)
Assignee: TERUMO KABUSHIKI KAISHA
B01D65/102B01D63/02
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Quick Facts
Patent No.
US 12,465,892
App. No.
18/239,352
Granted
Nov 11, 2025
Kind
B2
Abstract

A covering state of a coating layer containing a silicone compound on an inner surface of hollow fiber membranes is evaluated by dissolving the silicone compound and a dyeing agent in an organic solvent and causing the coating solution to pass through the hollow fiber membranes. The covering state of the silicone compound or a crosslinked product is determined by observing a dyed state of a hollow fiber membrane end surface on a coating solution passing start side and a dyed state of a hollow fiber membrane end surface on a coating solution passing end side of the hollow fiber membrane on which the coating layer is formed.

Claims (27)

1 . A method for evaluating a covering state of a silicone compound on a hollow fiber membrane for treating blood in an oxygenator, comprising the steps of:

dissolving a silicone compound and a dyeing agent in an organic solvent to prepare a coating solution;

causing the coating solution to pass through an inner surface of a hollow fiber membrane to form a coating layer containing the silicone compound and/or a crosslinked product of the silicone compound and the dyeing agent on the inner surface; and

evaluating a covering state of the silicone compound/the crosslinked product by observing a dyed state of a hollow fiber membrane end surface on a coating solution passing start side and a dyed state of a hollow fiber membrane end surface on a coating solution passing end side of the hollow fiber membrane on which the coating layer is formed.

2 . The method according to claim 1 , wherein the dyeing agent is selected from Rhodamine B, Rhodamine 6G, Rhodamine 6GP, Rhodamine 3GO, Rhodamine 123, fluorescein and a derivative thereof, and a polymer having these molecules in at least one of a side chain and a terminal.

3 . The method according to claim 1 , wherein a surface tension of the organic solvent is less than 70 dyn/cm.

4 . The method according to claim 3 , wherein the organic solvent is at least one selected from the group consisting of n-hexane, cyclohexane, acetone, butyl alcohol, 1-propanol, isopropanol, chloroform, diethyl ether, an aromatic hydrocarbon, and a fluorine-based solvent.

5 . The method according to claim 1 , wherein at least a part of the hollow fiber membrane is formed of a polypropylene or polymethylpentene.

6 . The method according to claim 1 , wherein the silicone compound is represented by the following Formula (1):

and wherein in the above Formula (1), R 1 to R 8 each independently represent an alkyl group having 1 or more and 6 or less carbon atoms, an aromatic hydrocarbon group having 6 or more and 30 or less carbon atoms, or a reactive group selected from the group consisting of an ethylenically unsaturated bond-containing group having 1 or more and 6 or less carbon atoms, an amino group-containing group, a hydroxy group-containing group, a carboxy group-containing group, a maleimide group-containing group, a thiol group-containing group, and a halogen group; and n is 1 or more and 100,000 or less.

7 . A method for evaluating a covering state of a silicone compound on a bundle of a plurality of hollow fiber membranes for treating blood in an oxygenator, comprising the steps of:

dissolving a silicone compound and a dyeing agent in an organic solvent to prepare a coating solution;

causing the coating solution to pass through an inner surface of the hollow fiber membranes in the bundle to form a coating layer containing the silicone compound and/or a crosslinked product of the silicone compound and the dyeing agent on the inner surface; and

evaluating a covering state of the silicone compound/the crosslinked product of each hollow fiber membrane by observing a dyed state of a hollow fiber membrane end surface on a coating solution passing start side and a dyed state of a hollow fiber membrane end surface on a coating solution passing end side of the hollow fiber membrane on which the coating layer is formed;

counting a number of the hollow fiber membranes with the dyed state at their coating solution passing end side; and

calculating a dyeing ratio according to the number of hollow fiber membranes within the bundle which are dyed on the coating solution passing end side and a number of hollow fiber membranes dyed on the coating solution passing start side.

8 . The method according to claim 7 , further comprising the steps of:

determining a failure of the bundle of hollow fiber membranes when the calculated dyeing ratio is less than a predetermined percentage; and

determining a pass of the bundle of hollow fiber membranes when the calculated dyeing ratio is greater than the predetermined percentage.

9 . The method according to claim 8 , wherein the predetermined percentage is about 90%.

10 . The method according to claim 8 , wherein the predetermined percentage is about 95%.

11 . The method according to claim 7 , wherein the dyeing agent is selected from Rhodamine B, Rhodamine 6G, Rhodamine 6GP, Rhodamine 3GO, Rhodamine 123, fluorescein and a derivative thereof, and a polymer having these molecules in at least one of a side chain and a terminal.

12 . The method according to claim 7 , wherein a surface tension of the organic solvent is less than 70 dyn/cm.

13 . The method according to claim 12 , wherein the organic solvent is at least one selected from the group consisting of n-hexane, cyclohexane, acetone, butyl alcohol, 1-propanol, isopropanol, chloroform, diethyl ether, an aromatic hydrocarbon, and a fluorine-based solvent.

14 . The method according to claim 7 , wherein at least a part of the hollow fiber membranes is formed of a polypropylene or polymethylpentene.

15 . The method according to claim 7 , wherein the silicone compound is represented by the following Formula (1):

and wherein in the above Formula (1), R 1 to R 8 each independently represent an alkyl group having 1 or more and 6 or less carbon atoms, an aromatic hydrocarbon group having 6 or more and 30 or less carbon atoms, or a reactive group selected from the group consisting of an ethylenically unsaturated bond-containing group having 1 or more and 6 or less carbon atoms, an amino group-containing group, a hydroxy group-containing group, a carboxy group-containing group, a maleimide group-containing group, a thiol group-containing group, and a halogen group; and n is 1 or more and 100,000 or less.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA PREVIOUSLY RECORDED AT REEL: 064750 FRAME: 0536. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENET. Recorded Sep 6, 2023
From: SATO, TAKESHI; TAKAMA, RENJO
To: TERUMO KABUSHIKI KAISHA
Reel/Frame 064850/0160 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2023
From: SATO, TAKESHI; TAKAMA, RENJO
To: FORD GLOBAL TECHNOLOGIES, LLC
Reel/Frame 064750/0536 →
Priority Claims (1)
JP 2021-034251 · Mar 4, 2021 · national
Continuity (2)
Continuation PCTJP2022006839 · Feb 21, 2022
Related Publication 20230398501A1 · Dec 14, 2023
References Cited (15)
US 1075657A · Krompigel et al. · 1913 [cited by applicant]
US 5298255A · Sawamoto et al. · 1994 [cited by applicant]
US 20150013137A1 · Olsen · 2015 [cited by examiner]
US 20230001358A1 · Sato et al. · 2023 [cited by applicant]
JP S5739851A · 1982 [cited by applicant]
JP S63154180A · 1988 [cited by applicant]
JP H04152952A · 1992 [cited by applicant]
JP 2009125600A · 2009 [cited by applicant]
JP 2018149270A · 2018 [cited by applicant]
JP 2021142163A · 2021 [cited by applicant]
KR 20110066376A · 2011 [cited by applicant]
WO WO2012147850A1 · 2012 [cited by examiner]
WO WO2021076437A1 · 2021 [cited by examiner]
International Search Report, PCT/JP2022/006839, Apr. 7, 2022. [cited by applicant]
International Search Opinion, PCT/JP2022/006839, Apr. 26, 2023. [cited by applicant]