IP Library › Granted Patent US 10,632,456
Granted Patent B2
US 10,632,456 · App. 15/743,043 · Granted Apr 28, 2020

Process for producing organic acid ester-type liquid, and process for producing solvent of resist for producing electronic part or rinsing liquid for producing electronic parts

Inventors: Masakazu Tsukida (Kitaibaraki, JP); Hitoshi Takada (Tokyo, JP)
Assignee: MUSASHINO CHEMICAL LABORATORY, LTD.
B01J31/08B01J35/10G03F7/0048G03F7/0382G03F7/0397G03F7/16G03F7/32G03F7/40H01L21/027
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Quick Facts
Patent No.
US 10,632,456
App. No.
15/743,043
Granted
Apr 28, 2020
Kind
B2
Abstract

A process for producing an organic acid ester-type liquid is disclosed which is a process for removing an organic peroxide contained in an organic acid ester-type liquid which is a solvent of a resist for producing electronic parts or an organic acid ester-type liquid which is a rinsing liquid for producing electronic parts, which comprises contacting the organic acid ester-type liquid with a platinum group metal catalyst to remove the organic peroxide in the organic acid ester-type liquid, and a resist solvent for producing electronic parts or a rinsing liquid for producing electronic parts which comprises an organic acid ester-type liquid in which an organic peroxide contained therein has been removed by using the producing process and a peroxide value (POV) thereof is 2 mmoL/kg or less.

Claims (64)

1. A process for producing a peroxide-removed organic acid ester liquid, comprising:

contacting an organic acid ester liquid with a platinum group metal catalyst which is carried on a synthetic resin, thereby removing an organic peroxide from the organic acid ester liquid,

wherein the organic acid ester liquid is a solvent of a resist for producing electronic parts or a rinsing liquid for producing electronic parts.

2. The process for producing a peroxide-removed organic acid ester liquid according to claim 1 ,

wherein the organic acid ester liquid is contacted with the synthetic resin onto which the platinum group metal catalyst has been carried, and

wherein the synthetic resin is a material in which the platinum group metal catalyst is carried onto an organic porous anion exchanger having a monolith structure.

3. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein nanoparticles of a platinum group metal having an average particle size of 1 to 100 nm are carried onto the organic porous anion exchanger,

wherein the organic porous anion exchanger comprises a continuous skeletal phase and a continuous porous phase,

wherein a thickness of a continuous skeleton of the continuous skeletal phase is 1 to 100 μm,

wherein the organic porous anion exchanger has an average diameter of continuous pores of 1 to 1,000 μm,

wherein the organic porous anion exchanger has a total pore volume of 0.5 to 50 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g, and

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger.

4. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger has a continuous cell structure which has mesopores having an average diameter of 1 to 1,000 μm in walls of macropores which are interconnected to each other,

wherein the organic porous anion exchanger has a total pore volume of 1 to 50 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g, and

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger.

5. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger forms a three-dimensionally continuous skeletal portion by agglomerating organic polymer particles having an average particle size of 1 to 50 μm,

wherein the organic porous anion exchanger has three-dimensionally continuous pores having an average diameter of 20 to 100 μm between skeletons,

wherein the organic porous anion exchanger has a total pore volume of 1 to 10 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g, and

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger.

6. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger is a co-continuous structural body comprising three-dimensionally continuous skeletons having an average thickness of 1 to 60 μm,

wherein the organic porous anion exchanger comprises an aromatic vinyl polymer containing 0.3 to 5.0 mol % of a crosslinking structure unit based on whole constitutional units into which ion exchange groups have been introduced,

wherein the organic porous anion exchanger comprises three-dimensionally continuous pores having an average diameter of 10 to 200 μm between the skeletons,

wherein the organic porous anion exchanger has a total pore volume of 0.5 to 10 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g, and

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger.

7. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger is a continuous macropore structural body in which bubble shaped macropores are overlapped with each other, overlapping portions being openings having an average diameter of 30 to 300 μm,

wherein the organic porous anion exchanger has a total pore volume of 0.5 to 10 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g,

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger, and

wherein, in an SEM image of a cut surface of the continuous macropore structural body, a skeletal part area appearing in a cross-section is 25 to 50% in an image area.

8. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger comprises a continuous skeletal phase and a continuous porous phase,

wherein the skeletal phase has

a plurality of particle bodies having a diameter of 4 to 40 μm fixed to a surface of the skeletal phase of the organic porous body, or

a plurality of protrusions having a size of 4 to 40 μm formed onto the surface of the skeletal phase of the organic porous body,

wherein the organic porous anion exchanger has an average diameter of continuous pores of 10 to 150 μm,

wherein the organic porous anion exchanger has a total pore volume of 0.5 to 10 mL/g,

wherein the organic porous anion exchanger has an ion exchange capacity per a weight in a dry state of 0.5 to 6 mg equivalent/g, and

wherein ion exchange groups are uniformly distributed in the organic porous anion exchanger.

9. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 ,

wherein the organic porous anion exchanger is a continuous macropore structural body in which bubble shaped macropores are overlapped with each other, overlapping portions being openings having an average diameter of 20 to 300 μm,

wherein a surface-layer part of a skeletal part of the continuous macropore structural body is a porous structure,

wherein the organic porous anion exchanger has an anion exchange capacity per a volume in a wet state of 0.4 mg equivalent/mL or more, and

wherein the organic porous anion exchanger has anion exchange groups are uniformly distributed in the organic porous anion exchanger.

10. The process for producing a peroxide-removed organic acid ester liquid according to claim 2 , wherein the organic porous anion exchanger is an OH − form.

11. The process for producing a peroxide-removed organic acid ester liquid according to claim 1 , wherein the platinum group metal catalyst is a palladium catalyst.

12. The process for producing a peroxide-removed organic acid ester liquid according to claim 1 , wherein the organic peroxide in the organic acid ester liquid is removed until a peroxide value (POV) becomes 2 mmol/kg or less.

13. The process for producing a peroxide-removed organic acid ester liquid according to claim 1 , wherein the organic acid ester liquid contains at least one selected from the group consisting of methyl acetate, ethyl acetate, propyl acetate, butyl acetate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl pyruvate, ethyl pyruvate and butyl pyruvate.

14. The process for producing a peroxide-removed organic acid ester liquid according to claim 1 ,

wherein the synthetic resin is a crosslinked resin having fine pores.

15. The process for producing a peroxide-removed organic acid ester liquid according to claim 14 ,

wherein the crosslinked resin has through holes.

16. A process for producing a resist solvent for producing electronic parts or a rinsing liquid for producing electronic parts, comprising:

removing an organic peroxide contained in an organic acid ester liquid which is a solvent of a resist for producing electronic parts or a rinsing liquid for producing electronic parts by using the process for producing an organic acid ester liquid according to claim 1 .

17. A method for reprocessing an organic acid ester liquid which is a method for reprocessing an organic acid ester liquid using the process for producing an organic acid ester liquid according to claim 1 , comprising:

removing an organic peroxide in the organic acid ester liquid by contacting the organic acid ester liquid a peroxide value (POV) of which is increased during storage or transportation with a platinum group metal catalyst.

Assignments (2)
CHANGE OF ADDRESS Recorded Feb 2, 2022
From: MUSASHINO CHEMICAL LABORATORY, LTD.
To: MUSASHINO CHEMICAL LABORATORY, LTD.
Reel/Frame 058945/0952 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2018
From: TSUKIDA, MASAKAZU; TAKADA, HITOSHI
To: MUSASHINO CHEMICAL LABORATORY, LTD.
Reel/Frame 044573/0894 →
Priority Claims (1)
JP 2015-138977 · Jul 10, 2015 · national
Continuity (1)
Related Publication 20190076833A1 · Mar 14, 2019