Oil agent for carbon fiber precursor acrylic fiber, oil composition for carbon fiber precursor acrylic fiber, processed-oil solution for carbon-fiber precursor acrylic fiber, and method for producing carbon-fiber precursor acrylic fiber bundle, and carbon-fiber bundle using carbon-fiber precursor acrylic fiber bundle

Patent metadata

Field	Value
Publication number	US-10072359-B2
Application number	US-201214123915-A
Country	US
Kind code	B2
Filing date	Jun 6, 2012
Priority date	Jun 6, 2011
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to an oil agent for carbon-fiber precursor acrylic fiber, including at least one type of compound selected from groups of a hydroxybenzoate (Compound A), a cyclohexanedicarboxylic acid (Compound B and C), a cyclohexanedimethanol and/or a cyclohexanediol and a fatty acid (Compound D and E) and an isophoronediisocyanate-aliphatic alcohol adduct (Compound F), an oil composition for carbon-fiber precursor acrylic fiber, a processed-oil solution for carbon-fiber precursor acrylic fiber, and a method for producing a carbon-fiber precursor acrylic fiber bundle, and a carbon-fiber bundle using the carbon-fiber precursor acrylic fiber bundle.

First claim

What is claimed is:

1. A method for manufacturing a carbon-fiber bundle, comprising heat treating a carbon-fiber precursor acrylic fiber bundle under a 200˜400° C. oxidizing atmosphere, followed by heat treating under a 1000° C. or higher inert atmosphere, wherein
an oil agent is adhered to the carbon-fiber precursor acrylic fiber bundle, and
the oil agent comprises compound A which is represented by formula (1a):

wherein R 1a is a hydrocarbon group having 8˜20 carbon atoms.

2. The method of claim 1 , wherein the oil agent further comprises at least one type of compound selected from the group consisting of B, C, D, E and F:
B: compound B obtained through a reaction of a cyclohexanedicarboxylic acid and a monohydric aliphatic alcohol having 8˜22 carbon atoms;
C: compound C obtained through a reaction of a cyclohexanedicarboxylic acid, a monohydric aliphatic alcohol having 8˜22 carbon atoms, a polyhydric alcohol having 2˜10 carbon atoms and/or a polyoxyalkylene glycol with an oxyalkylene group having 2˜4 carbon atoms;
D: compound D obtained through a reaction of a cyclohexanedimethanol and/or cyclohexanediol, and a fatty acid having 8˜22 carbon atoms;
E: compound E obtained through a reaction of a cyclohexanedimethanol and/or cyclohexanediol, fatty acid having 8˜22 carbon atoms and a dimer acid; and
F: compound F obtained through a reaction of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl=isocyanate and at least one type of compound selected from the group consisting of monohydric aliphatic alcohol having 8˜22 carbon atoms and a polyoxyalkylene ether compound of a monohydric aliphatic alcohol having 8˜22 carbon atoms.

3. The method of claim 2 , wherein the oil agent comprises compound B, and
wherein compound B is represented by formula (1b):

wherein R 1b and R 2b each independently is a hydrocarbon group having 8˜22 carbon atoms.

4. The method of claim 2 , wherein the oil agent comprises compound C, and
wherein compound C is represented by formula (2b):

wherein R 3b and R 5b each independently is a hydrocarbon group having 8˜22 carbon atoms, and R 4b is a residue obtained by removing two hydroxyl groups from a hydrocarbon group having 2˜10 carbon atoms or from a polyoxyalkylene glycol with an oxyalkylene group having 2˜4 carbon atoms.

5. The method of claim 2 , wherein the oil agent comprises compound D, and
wherein compound D is represented by formula (1c):

wherein R 1c and R 2c each independently is a hydrocarbon group having 7˜21 carbon atoms, and nc independently represents 0 or 1.

6. The method of claim 2 , wherein the oil agent comprises compound E, and
wherein compound E is represented by formula (2c):

wherein R 3c and R 5c each independently is a hydrocarbon group having 7˜21 carbon atoms, R 4c is a hydrocarbon group having 30˜38 carbon atoms, and mc independently represents 0 or 1.

7. The method of claim 2 , wherein the oil agent comprises compound F, and
wherein compound F is represented by formula (1d):

wherein R 1d and R 4d each independently is a hydrocarbon group having 8˜22 carbon atoms, R 2d and R 3d each independently is a hydrocarbon group having 2˜4 carbon atoms, and nd and md each independently mean the average number of added moles in numerals 0˜5.

8. The method of claim 1 , wherein the oil agent further comprises an ester compound G comprising 1 or 2 aromatic rings.

9. The method of claim 1 , wherein the oil agent further comprises an amino-modified silicone H.

10. The method of claim 8 , wherein the ester compound G is ester compound G1 represented by formula (1e) and/or ester compound G2 represented by formula (2e):

wherein R 1c ˜R 3e each independently is a hydrocarbon group having 8˜16 carbon atoms, and

wherein R 4e and R 5e each independently is a hydrocarbon group having 7˜21 carbon atoms, and oe and pe each independently represent 1˜5.

11. The method of claim 9 , wherein the amino-modified silicone H is an amino-modified silicone represented by formula (3e), and whose kinetic viscosity at 25° C. is 50˜500 mm 2 /s, and whose amino equivalent is 2000˜6000 g/mol:

wherein qe and re are any numeral greater than 1, and se is a numeral from 1˜5.

12. The method of claim 1 , wherein the amount of the oil agent is 0.1˜1.5 mass % of dry fiber mass.

13. The method of claim 1 , wherein the amount of the oil agent is 0.1˜1.5 mass % of dry fiber mass, and an ester compound G having 1 or 2 aromatic rings or an amino-modified silicone H is adhered to the carbon-fiber precursor acrylic fiber bundle at 0.0˜1.2 mass % of dry fiber mass.

14. The method of claim 1 , wherein a nonionic surfactant is adhered to the carbon-fiber precursor acrylic fiber bundle at 0.05˜1.0 mass % of dry fiber mass.

15. The method of claim 1 , wherein an antioxidant is adhered to the carbon-fiber precursor acrylic fiber bundle at 0.01˜0.1 mass % of dry fiber mass.

16. The method of claim 1 , wherein
a surfactant is adhered to the carbon-fiber precursor acrylic fiber bundle at 0.05˜1.0 mass % of dry fiber mass, and
the surfactant is at least one selected from the group consisting of a polyether block copolymer represented by formula (4e) and a polyoxyethylene alkyl ether represented by formula (5e):

wherein R 6e and R 7e are each independently a hydrogen atom or a hydrocarbon group having 1˜24 carbon atoms, and xe, ye, and ze are each independently from 1˜500,

wherein R 8e is a hydrocarbon group having 10˜20 carbon atoms, and to is from 3˜20.

Assignees

• Aso Hiromi
• Tsuchihashi Masaaki
• Takano Tetsuo
• Mitsubishi Chem Corp

Inventors

• Aso Hiromi
• Tsuchihashi Masaaki
• Takano Tetsuo

Classifications

• D06M15/568

  Reaction products of isocyanates with polyethers · CPC title

• D06M2101/28

  Acrylonitrile; Methacrylonitrile · CPC title

• D06M13/425

  Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes (unsubstituted carbamic acid D06M11/67) · CPC title

• D06M7/00 Primary

  Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins (D06M10/00 takes precedence; treating fibres or filaments made of glass, mineral -, or slag wool C03C; carbon fibres D01F11/10) · CPC title

• D01F9/21 Primary

  from macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title