Silicone-modified polyurethane fiber and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-11174335-B2
Application number	US-201716091024-A
Country	US
Kind code	B2
Filing date	Mar 31, 2017
Priority date	Apr 4, 2016
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

Disclosed herein is a fiber formed from a resin including a silicone-modified polyurethane resin comprising the reaction products of a polyol (A), a chain extender (B), an active-hydrogen-group-containing organopolysiloxane (C), and a polyisocyanate (D), wherein the active-hydrogen-group-containing organopolysiloxane (C) contains an active-hydrogen-group-containing organopolysiloxane (C-1) having a carbinol group at only one terminal.

First claim

The invention claimed is:

1. A fiber formed from a resin comprising a silicone-modified polyurethane resin comprising the reaction product of a polyol (A), a chain extender (B), an active hydrogen-containing organopolysiloxane (C), and a polyisocyanate (D), the active hydrogen-containing organopolysiloxane (C) containing an active hydrogen-containing organopolysiloxane (C-1) having a carbinol group only at one end, wherein
the fiber has fiber diameter of less than 1,000 nm, and
the active hydrogen-containing organopolysiloxane (C) further contains an organopolysiloxane (C-2) having the following formula (3):
R 8 SiR 2 R 3 O(SiR 2 R 3 O) m SiR 2 R 3 R 8   (3)

wherein R 2 and R 3 are as defined above, R 8 is each independently a C 1 -C 10 monovalent hydrocarbon which has a hydroxyl or mercapto group and may have an oxygen atom intervening in the chain, or a C 1 -C 10 monovalent hydrocarbon group having a primary or secondary amino group, and m is an integer of 1 to 60.

2. The fiber of claim 1 wherein the active hydrogen-containing organopolysiloxane (C-1) having a carbinol group is an organopolysiloxane having the following formula (1):
R 1 R 2 R 3 SiO(SiR 2 R 3 O) n SiR 2 R 3 R 4   (1)

wherein R 1 , R 2 and R 3 are each independently selected from a straight, branched or cyclic C 1 -C 10 alkyl group in which some hydrogen may be substituted by fluorine, optionally substituted C 5 -C 12 aryl group, and vinyl group, R 4 is represented by the following formula (2):
—R 5 —X—CH 2 CR 6 (R 7 ) 2   (2)

wherein R 5 is a C 2 -C 10 divalent alkylene group which may contain an oxygen atom in the chain, R 6 is hydrogen, amino or C 1 -C 10 monovalent alkyl group, R 7 is a C 1 -C 10 carbinol group, and X is a single bond or —O— bond, and n is an integer of 1 to 200.

3. The fiber of claim 2 wherein the carbinol group is selected from hydroxymethyl, 2-hydroxyethan-1-yl, 2-hydroxypropan-1-yl, 3-hydroxypropan-1-yl, 2-hydroxybutan-1-yl, 4-hydroxybutan-1-yl, 5-hydroxypentan-1-yl, 6-hydroxyhexan-1-yl, 7-hydroxyheptan-1-yl, 8-hydroxyoctan-1-yl, 9-hydroxynonan-1-yl, and 10-hydroxydecan-1-yl.

4. The fiber of claim 1 wherein a ratio of the organopolysiloxane (C-1) having formula (1) to the organopolysiloxane (C-2) having formula (3), that is, (C-1):(C-2) is from 99:1 to 1:99 as a weight ratio.

5. The fiber of claim 1 wherein component (C) is present in an amount of 0.1 to 50 parts by weight per 100 parts by weight of components (A) to (D) combined.

6. The fiber of claim 1 wherein the silicone-modified polyurethane resin has a number average molecular weight of 10,000 to 200,000.

7. The fiber of claim 1 which has a fiber diameter of 100 nm to less than 1,000 nm.

8. A fiber layup structure comprising the fiber of claim 1 .

9. A method for preparing the fiber of claim 1 , comprising the step of spinning a fiber from a solution or dispersion of the silicone-modified polyurethane resin by an electrospinning method.

10. The method for preparing the fiber of claim 9 wherein the silicone-modified polyurethane resin is fed in the form of a solution or dispersion in an organic solvent, water or a mixture thereof.

11. A fiber formed from a resin comprising a silicone-modified polyurethane resin comprising the reaction product of a polyol (A), a chain extender (B), an active hydrogen-containing organopolysiloxane (C), and a polyisocyanate (D), the active hydrogen-containing organopolysiloxane (C) containing an active hydrogen-containing organopolysiloxane (C-1) having a carbinol group only at one end and an organopolysiloxane (C-2) having the following formula (3):
R 8 SiR 2 R 3 O(SiR 2 R 3 O) m SiR 2 R 3 R 8   (3)

wherein R 2 and R 3 are as defined above, R 8 is each independently a C 1 -C 10 monovalent hydrocarbon which has a hydroxyl or mercapto group and may have an oxygen atom intervening in the chain, or a C 1 -C 10 monovalent hydrocarbon group having a primary or secondary amino group, and m is an integer of 1 to 60.

12. The fiber of claim 11 wherein a ratio of the organopolysiloxane (C-1) having formula (1) to the organopolysiloxane (C-2) having formula (3), that is, (C-1):(C-2) is from 99:1 to 1:99 as a weight ratio.

Assignees

• Shinetsu Chemical Co
• Dainichiseika Color Chem
• Shinshu Univ National Univ Corporation
• Dainchiseik Color & Chemicals Mfg Co Ltd

Inventors

• Hattori Hatsuhiko
• Tanaka Masaki
• Sato Hiromasa
• Iino Shota
• Umezu Motoaki
• Tanaka Toshihisa
• KONDO Mikihisa

Classifications

• D01D5/0007

  Electro-spinning (non-woven fabrics produced by electro-spinning D04H1/728) · CPC title

• C08G18/4009

  Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64 · CPC title

• D04H1/4358

  Polyurethanes · CPC title

• D04H1/728

  by electro-spinning {(electro-spinning methods and apparatus D01D5/0007)} · CPC title

• C08G18/65

  Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen {(C08G18/2805 takes precedence)} · CPC title