# US 10,370,490 B2 · Polycarbonate fibers and substrates comprising same

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- Number: US 10,370,490 B2
- Document ID: US10370490B2
- Status: Granted
- Kind: B2
- Application number: 15/301,248
- Filed: 2015-04-03
- Published: 2017-01-19
- Granted: 2019-08-06
- Earliest claimed: 2014-04-04
- Assignees: Sabic Global Technologies B.V.
- Applicants: SABIC Global Technologies B.V.
- Inventors: Amanda Marie Flores; Jacob LaBelle; Peter James Zuber; Kim R. Choate
- Web page: https://patentgrep.com/patent/US10370490B2

## CPC

- C08G 64/14: containing a chain-terminating or -crosslinking agent
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 3/28: Treatment by wave energy or particle radiation
- C08L 69/00: Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C09D 169/00: Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
- D01D 5/06: Wet spinning methods {(D01D5/0046 takes precedence)}
- D01D 10/00: Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected (finishing D02J)
- D01F 6/64: from polycarbonates
- D21H 13/20: from macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C08J 2369/00: Characterised by the use of polycarbonates; Derivatives of polycarbonates
- C08L 2201/02: Flame or fire retardant/resistant
- C08L 2201/08: Stabilised against heat, light or radiation or oxydation
- C08L 2203/12: used for fibers
- C08L 2205/16: Fibres; Fibrils
- C08L 2312/06: by radiation
- D01D 5/04: Dry spinning methods {(D01D5/0038 takes precedence)}
- D01D 5/18: by means of rotating spinnerets
- D10B 2505/02: Reinforcing materials; Prepregs
- D10B 2505/04: Filters
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- D01D: MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01F: CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D10B: INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES

## Abstract

Disclosed herein are polycarbonate fibers and fibrous substrates, such as papers, containing such fibers. The polycarbonate fibers are produced from a polymeric composition comprising a cross-linkable polycarbonate containing endgroups derived from a monofunctional benzophenone or containing repeating units derived from a difunctional benzophenone. The polycarbonate fibers can be combined with other fibers to form the fibrous substrate. Upon exposure to ultraviolet light, crosslinking of the polycarbonate fibers will occur, improving various properties of the fibrous substrate.

## Claims

### Claim 1

A cross-linkable polycarbonate fiber, formed from a polymeric composition comprising a cross-linkable polycarbonate resin containing a photoactive group derived from a monohydroxybenzophenone, wherein the cross-linkable polycarbonate resin does not contain any residual pyridine, and the cross-linkable polycarbonate resin does not contain any repeating units derived from dihydroxybenzophenones.

### Claim 2 (depends on 1)

The fiber of claim 1, having a diameter of about 1 micron to 40 microns and an aspect ratio of about 3:1 to about 1 million:1.

### Claim 3 (depends on 1)

The fiber of claim 1, wherein the cross-linkable polycarbonate resin is formed from a reaction of: monohydroxybenzophenone; a diol chain extender; and a first linker moiety comprising a plurality of linking groups, wherein each linking group can react with the hydroxyl groups of the monohydroxybenzophenone and the diol chain extender.

### Claim 4 (depends on 1)

The fiber of claim 1, wherein the cross-linkable polycarbonate resin contains from about 0.5 mole % to about 5 mole % of endcap groups derived from the monohydroxybenzophenone and has a polydispersity index (PDI) of between 3.0 and 7.3 as measured by GPC using a UV-VIS detector and polycarbonate standards.

### Claim 5 (depends on 1)

The fiber of claim 1, wherein the polymeric composition forms the exterior surface of the fiber.

### Claim 6 (depends on 1)

The fiber of claim 1, wherein the fiber does not include a coating or jacket.

### Claim 7 (depends on 1)

An article comprising the fiber of claim 1.

### Claim 8 (depends on 1)

A fibrous substrate comprising polycarbonate fibers of claim 1.

### Claim 9 (depends on 8)

The fibrous substrate of claim 8, wherein the polycarbonate fibers comprise from about 20 wt % to about 80 wt % of the fibrous substrate.

### Claim 10 (depends on 8)

The fibrous substrate of claim 8, wherein the fibrous substrate further comprises first fibers.

### Claim 11 (depends on 10)

The fibrous substrate of claim 10, wherein the first fibers and the polycarbonate fibers are evenly dispersed throughout the fibrous substrate.

### Claim 12 (depends on 10)

The fibrous substrate of claim 10, wherein the first fibers are made from a material selected from the group consisting of carbon, glass, aramid, basalt, quartz, boron, cellulose, natural fibers, liquid crystal polymer, and high tenacity polymer; or are made from a thermoplastic selected from the group consisting of polycarbonates, polyimides, polyetheretherketone, polyetherketone, polyetherketoneketone, acrylonitrile butadiene styrene, polyoxymethylene, poly(p-phenylene ether), polypropylenes, polyethylenes, polystryrenes, polyvinyls, polyethyleneterephthalates, polybutylene terephthalates, acrylics, nylons, thermoplastic polyurethanes, polyacetals, polyphenylene sulfides, cycloolefin copolymers and thermotropic polyesters.

### Claim 13 (depends on 8)

The fibrous substrate of claim 8, wherein the dimensional stability of the substrate is improved after UV exposure, as measured by an absolute improvement in the average % loss of fiber length of 9.5% or more compared to before the UV exposure at 160° C.

### Claim 14 (depends on 8)

A process for producing a strengthened fibrous substrate comprising: exposing the fibrous substrate of claim 8 to a dosage of UV radiation.

### Claim 15 (depends on 1)

The fibrous substrate of claim 1, wherein the cross-linkable polycarbonate further comprises about 0.5 mol % to about 5 mol % of endcap groups derived from a second end-capping agent selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, and 4-cyanophenol.

### Claim 16

A cross-linkable polycarbonate fiber, formed from a polymeric composition comprising a cross-linkable polycarbonate resin containing a photoactive group derived from a dihydroxybenzophenone and endcap groups derived from an end-capping agent selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, octylphenol, and p-cyanophenol, wherein the cross-linkable polycarbonate resin does not contain any residual pyridine, and the polymeric composition further comprises a polymeric base resin, wherein the weight ratio of the cross-linkable polycarbonate resin to the polymeric base resin is from about 50:50 to about 95:5, wherein a fibrous substrate comprising the cross-linkable polycarbonate fiber has improved dimensional stability after UV exposure, as measured by an absolute improvement in the average % loss of fiber strength of 95% or more compared to before the UV exposure at 160° C.

### Claim 17 (depends on 16)

The fiber of claim 16, wherein the cross-linkable polycarbonate resin is formed from a reaction of: the dihydroxybenzophenone; a diol chain extender; a first linker moiety comprising a plurality of linking groups, wherein each linking group can react with the hydroxyl groups of the dihydroxybenzophenone and the diol chain extender; and the endcapping agent.

### Claim 18 (depends on 17)

The fiber of claim 17, wherein the dihydroxybenzophenone is 4,4′ dihydroxybenzophenone; the diol chain extender is bisphenol-A; and the first linker moiety is phosgene.

### Claim 19 (depends on 1)

The fiber of claim 1, wherein the polymeric composition further comprises a polymeric base resin.

### Claim 20 (depends on 19)

The fiber of claim 19, wherein the weight ratio of the cross-linkable polycarbonate resin to the polymeric base resin is from about 50:50 to about 95:5.