Method for producing a cured product

Patent metadata

Field	Value
Publication number	US-9840601-B2
Application number	US-201715416509-A
Country	US
Kind code	B2
Filing date	Jan 26, 2017
Priority date	Feb 4, 2015
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

A photo-curable composition having superior curability at room temperature and storage stability, and also offer a rubber-like cured product thereof having a good profile of properties including heat resistance, low-temperature performance, chemical resistance, solvent resistance and oil resistance. Specifically, A photo-curable composition which includes (A) 100 parts by mass of a linear polyfluoro compound having at least two alkenyl groups in a molecule and a linear perfluoropolyether structure in a backbone of the molecule, (B) a fluorine-containing organohydrogenpolysiloxane having at least two hydrogens bonded to a silicon atom in a molecule, and (C) 0.1 to 500 ppm of a photoactive hydrosililation catalyst relative to the mass of component (A) in terms of metal atom, wherein an amount of component (B) is 0.5 to 3.0 mol of Si—H groups in component (B) relative to 1.0 mol of alkenyl groups in component (A).

First claim

What is claimed is:

1. A method for producing a cured product by irradiating a light to a photo-curable fluoropolyether-based rubber composition to cure the composition, the composition comprising:
(A) 100 parts by mass of a linear polyfluoro compound having: at least two alkenyl groups per molecule; and a linear perfluoropolyether structure in a backbone of the molecule,
(B) a fluorine-containing organohydrogenpolysiloxane having at least two hydrogens bonded to a silicon atom per molecule, said fluorine-containing organohydrogenpolysiloxane containing 0.5 to 3.0 mol of Si—H groups based on 1.0 mol of alkenyl groups in component (A); and
(C) 0.1 to 500 ppm of a photoactive hydrosililation catalyst based on the mass of component (A) in terms of metal atom,
wherein the photoactive hydrosililation catalyst of component (C) is (η 5 -cyclopentadienyl)tri(σ-alkyl) platinum (IV) complex compound and/or β-diketonate platinum (II) complex compound, and
the light has an emission spectrum having a maximum peak wavelength in a region from 300 nm to 400 nm, and a spectral irradiance of the light in any wavelengths shorter than 300 nm is not more than 5% with respect to the spectral irradiance of the light of the maximum peak wavelength.

2. The method for producing the cured product according to claim 1 , wherein component (A) is a linear polyfluoro compound represented by a formula (1):
CH 2 ═CH—(X) g —Rf 1 —(X′) g —CH═CH 2   (1)

wherein X represents —CH 2 —, —CH 2 O—, —CH 2 OCH 2 —, or —Y—NR 1 —CO—, wherein Y represents —CH 2 —, —Si(CH 3 ) 2 CH 2 CH 2 CH 2 —, —Si(CH 3 )(CH═CH 2 )CH 2 CH 2 CH 2 —, —Si(CH═CH 2 ) 2 CH 2 CH 2 CH 2 —, or an o-, m-, or p-silylphenylene group represented by a structural formula (Z) shown below,

wherein each of R 3 and R 4 independently represents —CH 3 or —CH═CH 2 ,
and R 1 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, X′ represents —CH 2 —, —OCH 2 —, —CH 2 OCH 2 —, or —CO—NR 2 —Y′—, wherein Y′ represents —CH 2 —, —CH 2 CH 2 CH 2 Si(CH 3 ) 2 —, —CH 2 CH 2 CH 2 Si(CH 3 )(CH═CH 2 )—, —CH 2 CH 2 CH 2 Si(CH═CH 2 ) 2 —, or an o-, m-, or p-silylphenylene group represented by a structural formula (Z′) shown below

wherein each of R 3′ and R 4′ independently represents —CH 3 or —CH═CH 2 ,
and R 2 represents a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group, g independently represents an integer of 0 or 1, and Rf 1 is a linear divalent perfluoropolyether group represented by a formula (i) or formula (ii) shown below,

wherein each of p and q representing an integer of 0 to 150, provided that an average of the sum of p and q is from 2 to 200, r representing an integer of 0 to 6, and t representing an integer of 2 or 3,

wherein u representing an integer of 1 to 200, v representing an integer of 1 to 50, and t representing an integer of 2 or 3.

3. The method for producing the cured product according to claim 1 , wherein the fluorine-containing organohydrogenpolysiloxane of component (B) has at least one monovalent perfluoroalkyl group, monovalent perfluorooxyalkyl group, divalent perfluoroalkylene group, or divalent perfluorooxyalkylene group per molecule.

4. The method for producing the cured product according to claim 1 , the composition further comprising (D) 0.5 to 30 parts by mass of hydrophobic silica powder having BET specific surface area of not less than 50 m 2 /g based on 100 parts by mass of component (A), as a filler.

5. The method for producing the cured product according to claim 1 , the composition further comprising (E) a reaction control agent for hydrosilylation reaction.

6. A method for producing a cured product, said method including the steps of:
providing a composition comprising:
(A) 100 parts by mass of a linear polyfluoro compound having: at least two alkenyl groups per molecule; and a linear perfluoropolyether structure in a backbone of the molecule;
(B) a fluorine-containing organohydrogenpolysiloxane having at least two hydrogens bonded to a silicon atom per molecule, said fluorine-containing organohydrogenpolysiloxane containing 0.5 to 3.0 mol of Si—H groups based on 1.0 mol of alkenyl groups in component (A); and
(C) 0.1 to 500 ppm of a photoactive hydrosililation catalyst based on the mass of component (A) in terms of metal atom, said catalyst being selected from the group consisting of (η 5 -cyclopentadienyl)tri(σ-alkyl) platinum (IV) complex compound, β-diketonate platinum (II) complex compound, and mixtures thereof; and
irradiating said composition with light having an emission spectrum with a maximum peak wavelength in a region from 300 nm to 400 nm and a spectral irradiance in any wavelengths shorter than 300 nm of not more than 5% with respect to the spectral irradiance of the light of the maximum peak wavelength.

7. The method of claim 6 , wherein the intensity of said irradiation is in the range from 100 to 100,000 mJ/cm 2 .

8. The method of claim 6 , wherein the duration of said irradiation is in the range from 1 to 300 seconds.

Assignees

• Shinetsu Chemical Co

Inventors

• Muto Mitsuo
• Fukuda Kenichi

Classifications

• C08L2205/05

  containing polymer components which can react with one another · CPC title

• C08G65/336

  containing silicon · CPC title

• C08G2650/48

  containing fluorine, e.g. perfluropolyethers · CPC title

• C08G77/46

  containing polyether sequences · CPC title

• C08K3/36

  Silica · CPC title