Perfluoro group-containing compounds and hardened polymer of...

Details Perfluoro group-containing compounds and hardened polymer of... Perfluoro group-containing compounds and hardened polymer of...

2000-03-17

2003-05-06

Tucker, Philip (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From phenol, phenol ether, or inorganic phenolate

C528S090000, C549S554000, C549S555000, C549S556000, C549S559000, C549S561000, C525S527000, C525S403000, C525S481000, C560S209000, C560S220000, C560S223000, C568S669000, C568S685000, C526S247000, C526S245000

Reexamination Certificate

active

06559268

ABSTRACT:

The present invention relates to a novel water-repellent and oil-repellent perfluoro group-containing compound and a hardened polymer thereof.
BACKGROUND OF THE INVENTION
The perfluoro group-containing compound is excellent in heat resistance because the linkages between carbon atoms and fluorine atoms are very strong and the compound has a low friction coefficient. For this reason, the perfluoro group-containing compound has been used for protecting the surface of a substrate by, for instance, applying it to the substrate surface; or incorporating it into a paint and applying the paint to the substrate surface to thus impart water repellency or oil repellency to the surface. For instance, Published International Patent Application No. WO98/12163 discloses a (meth)acrylic acid ester of perfluoro group-containing alcohol and a hardened polymer thereof and Japanese Patent Provisional Publication No. Hei 11-2702 discloses a low refractive index film comprising a perfluoro group-containing compound.
Under such circumstances, there has been desired for the development of a perfluoro group-containing compound and a hardened polymer thereof, whose adherence to the surface of a substrate is further improved.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a water-repellent and oil-repellent perfluoro group-containing novel, polymerizable compound.
It is another object of the present invention to provide a hardened polymer of the compound, whose adherence to the surface of a substrate is quite excellent.
The perfluoro group-containing compound of the present invention developed for accomplishing the foregoing objects is one represented by the following formula (I):
In Formula (I), —Rf— is a perfluoro group selected from the group consisting of —CH
2
—(CF
2
)
m
—(CH
2
)
n
—(wherein m is an integer ranging from 1 to 20 and n is also an integer ranging from 0 to 1), —CH
2
—(CF
2
)
p
—C[—(CF
2
)
q
—F][—(CF
2
)
r
—F]—CH
2
— (wherein p is an integer ranging from 1 to 10, q is an integer ranging from 0 to 22 and r is an integer ranging from 1 to 22), —CH
2
—(CF
2
)
s
—(—O—C
t
F
2t
)
u
—O—(CF
2
)
v
—(CH
2
)
w
— (wherein s, t, u, v and w are integers ranging from 1 to 3, 1 to 4, 1 to 100, 0 to 3 and 0 to 1, respectively),
(wherein x
1
and x
2
each is an integer ranging from 0 to 10); —A represents —OH or a group:
when n, v and w of the foregoing —Rf— not 0, or—C
y
F
2y+1
(y is an integer ranging from 1 to 22) when m=1~3 and n=1, m+y=6~22 and n=0, v=w=0, in the foregoing group: —Rf—, or —C
z
F
2z−1
(z is an integer ranging from 3 to 20) when m=1~10 and n=0, v=w=0 in the foregoing group: —Rf—.
The foregoing group: —CH
2
—(CF
2
)
m
—(CH
2
)n—may be, for instance, a dehydrogenated residue of 2,2-difluoropropane diol, 2,2,3,3-tetrafluorobutane diol, 2,2,3,3,4,4-hexafluoropentane diol, 2,2,3,3,4,4,5,5-octafluorohexane diol, 2,2,3,3,4,4,5,5,6,6-decafluoroheptane diol, 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctane diol, 2,2,3,3,4,4,5,5,6,6,7,7,8,8-tetradecafluorononane diol or 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-heptadecafluorodecane diol, when n is not 0.
The foregoing group: —CH
2
—(CF
2
)
p
—C[—(CF
2
)
q
—F][—(CF
2
)
r
—F]—CH
2
—may be, for instance, a dehydrogenated residue of 2-fluoro-2-perfluorooctyl-1,3-propane diol, 2-fluoro-2-perfluoroisooctyl-1,3-propane diol or 2-fluoro-2-perfluoro (4-ethyl-hexyl)-2-hydroxymethyl-1-methanol.
The foregoing group: —CH
2
—(CF
2
)
s
—(—O—C
t
F
2t
)
u
—O—(CF
2
)
v
—(CH
2
)
w
— may be, for instance, a dehydrogenated residue of 2,2,4,4-tetrafluorodiethylene glycol, 2,2,4,4,5,5,7,7-octafluorotriethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10-dodecafluorotetraethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10,11,11,13,13-heptadecafluoro pentaethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10,11,11,13,13,14,14,16,16-eicosafluorohexaethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10,11,11,13,13,14,14,16,16,17,17,19,19-tetracosafluoroheptaethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10,11,11,13,13,14,14,16,16,17,17,19,19,20,20,22,22-octacosafluorooctaethylene glycol, 2,2,4,4,5,5,7,7,8,8,10,10,11,11,13,13,14,14,16,16,17,17,19,19,20,20,22,22,23,23,25,25-dotriacontafluorononaethylene glycol, 2,4,4-trifluoro-2,5-di(trifluoromethyl)diethylene glycol, 2,4,4,5,7,7-hexafluoro-2,5,8-tri(trifluoromethyl)triethylene glycol, 2,4,4,5,7,7,8,10,10-nonafluoro-2,5,8,11-tetra(trifluoromethyl)tetraethylene glycol, 2,4,4,5,7,7,8,10,10,11,13,13-dodecafluoro-2,5,8,11,14-penta(trifluoromethyl)pentaethylene glycol, 2,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17-pentadecafluoro-2,5,8,11,14,17-hexa(trifluoromethyl)hexaethylene glycol, 2,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17,19,19,20-octadecafluoro-2,5,8,11,14,17,20-hepta(trifluoromethyl)heptaethylene glycol, 2,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17,19,19,20,22,22,23-docosafluoro-2,5,8,11,14,17,20,23-octa-(trifluoromethyl) octaethylene glycol, 2,4,4,5,7,7,8,10,10,11,13,13,14,16,16,17,19,19,20,22,22,23,25,25,26-tetracosafluoro-2,5,8,11,14,17,20,23,26-nona(trifluoromethyl)nonaethylene glycol, 2,2,3,3,4,4,6,6,7,7,8,8-dodecafluoroditetramethylene glycol, 2,2,3,3,4,4,6,6,7,7,8,8,9,9,11,11,12,12,13,13-eicosafluorotritetramethylene glycol, 2,2,3,3,4,4,6,6,7,7,8,8,9,9,11,11,12,12,13,13,14,14,16,16,17,17,18,18-octacosafluorotetratetramethylene glycol, 2,2-bis(4-hydroxy-decafluorocyclohexyl)-1,3-hexafluoropropane, 2,2-bis (4-hydroxymethyl-decafluorocyclohexyl)-1,3-hexafluoropropane, 2,2-bis[4-oxy(1,1-difluoroethoxy)-decafluorocyclohexyl]-1,3-hexafluoropropane, or 2,2-bis[4-oxy(1-perfluoromethyl-1-fluoroethoxy)-decafluorocyclohexyl]-1,3-hexafluoropropane.
The group: (C
y
F
2y+1
)—CH
2
O— which constitutes the group: —(C
y
F
2y+1
), may be, for instance, a dehydrogenated residue of perfluoromethanol, perfluoroethyl methanol, perfluoropropyl methanol, perfluorobutyl methanol, perfluoropentyl methanol, perfluorohexyl methanol, perfluorooctyl methanol, perfluorononyl methanol, perfluorodecyl methanol, perfluoroundecyl methanol, perfluorododecyl methanol, perfluorotridecyl methanol, perfluorotetradecyl methanol, perfluoropentadecyl methanol, perfluorohexadecyl methanol, perfluoroheptadecyl methanol, perfluorooctadecyl methanol, perfluorononadecyl methanol, perfluoroeicosyl methanol, or perfluoroheneicosyl methanol. In addition, the group: (C
y
F
2y+1
)—OCF
2
CH
2
O— may be, for instance, a dehydrogenated residue of 2-perfluoromethoxy-2,2-difluoroethanol, 2-perfluoroethoxy-2,2-difluoroethanol. The group: (C
y
F
2y+1
)—(CF
2
CF
2
—O—)
u
—CF
2
CH
2
O— may be, for instance, a dehydrogenated residue of 2-perfluorobutoxy-2,2-difluoroethanol, 2-perfluorooctoxy-2,2-difluoroethanol, 5-perfluoromethoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol, 5-perfluorobutoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol, 5-perfluorooctoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol, 8-perfluoromethoxy-7,7,8,8-tetrafluoroethoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol, 8-perfluorooctoxy-7,7,8,8-tetrafluoroethoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoro-ethanol, 11-perfluoromethoxy-10,10,11,11-tetrafluoroethoxy-7,7,8,8-tetrafluoroethoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol, or 11-perfluorooctoxy-10,10,11,11-tetrafIuoroethoxy-7,7,8,8-tetrafluoroethoxy-4,4,5,5-tetrafluoroethoxy-2,2-difluoroethanol.
Examples of the group: (C
z
F
2z−1
)—CH
2
O— which constitutes the group: —(C
z
F
2z−1
)— may be, for instance, a dehydrogenated residue of 1-undecafluorocyclohexyl methanol, 2-fluoro-2-undecafluorocyclohexyl ethanol, or 2,2,3-trifluoro-3-undecafluorocyclohexyl propanol.
A method for preparing a perfluoro group-containing epoxy compound represented by the foregoing formula (I) comprises the step of reacting a perfluoro group-containing mono- or di-alcohol with a halogenated epoxy propyl.
The perfluoro group-containing alcohol as a starting material can be prepared by, for instance, fluorinating a diester of an alkyl diol with fluorine gas in 1,1,2-trichloro-trifluoroethane and then reducing the flu

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