Quaternary ammonium salt for photo-curable antifogging...

Compositions: coating or plastic – Coating or plastic compositions – Fog – frost or ice preventive

Reexamination Certificate

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C522S006000, C522S008000, C522S033000, C522S121000, C523S169000, C524S186000

Reexamination Certificate

active

06176906

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a quaternary ammonium salt which may be used for a photo-curable antifogging composition. More particularly, the present invention relates to a quaternary ammonium salt which may be used for the photo-curable antifogging composition which may be applied to the surface of substrates such as glass, various plastic materials and the like to provide antifogging properties on the surface of these substrates, a preparation method for the ammonium salt and the photo-curable antifogging composition including the same.
2. Description of the Prior Art
When articles such as swimming goggles, lenses, coverlets of measuring instruments, window glasses, various films and the like are placed in an environment in which a temperature difference between the internal and the external side is large, tiny water droplets are formed on the surface of these articles. In order to overcome this predicament, a method of applying an antifogging agent to a surface of an article has been suggested. Also, various research for a photo-curable antifogging composition that may be cured by UV irradiation has been conducted.
A conventional antifogging composition comprising hydrophilic substances such as polyvinylalcohol crosslinked with a catalyst such as peroxide is disclosed in U.S. Pat. No. 5,262,475. However, the processing temperature of the composition is about 150° C. Thus, it is difficult to apply the composition to a thin film due to the high processing temperature. Moreover, the crosslinked antifogging layer becomes sticky and then flows upon contact with water. The surface hardness of the layer is merely 6B as Pencil Hardness. Therefore, the layer may be scratched readily and thus cannot be used for a long time.
Another conventional antifogging method is to apply a solution of a surface active agent to a surface of a substrate. However, the substrate treated by such a method provides only a temporary antifogging property. An conventional antifogging method is to apply a polymeric surface active agent to a surface of the substrate in order to impart long-lasting antifogging property thereto.
Still another conventional method wherein a polymeric surface active agent is incorporated into a coating composition is also disclosed in Korean Patent Publication No. 95-14730. According to this method, however, a thermal drying process which should be continued for 20 to 180 seconds is needed to remove residual polar solvent from the antifogging composition. Moreover, UV irradiation which lasts for 20 to 60 seconds is required to cure the composition. Consequently, this method has a drawback of a low productivity caused by a two-step curing precess and a long treating time. Moreover, the antifogging property of the substrate treated by this method also reduces suddenly after 1 to 2 months.
To overcome the above described predicaments of the prior arts, the inventors of the present invention carried out extensive studies, and as a result found that antifogging compositions comprising a specific quaternary ammonium salt which contains photo-curable functional groups, and a photo-curable oligomer, provide good surface hardness, excellent adhesion properties, and excellent antifogging properties lasting a long time.
SUMMARY OF THE INVENTION
The first object of the present invention is therefore to provide a quaternary ammonium salt which may be employed as a principal ingredient of a composition which may form a cured film which has high surface hardness, excellent adhesion properties and excellent antifogging properties lasting a long time.
The second object of the present invention is to provide a preparation method for the quaternary ammonium salt.
The third object of the present invention is to provide a composition which may form a cured film which has high surface hardness, excellent adhesion properties and excellent antifogging properties lasting a long time.
The fourth object of the present invention is to provide a hybrid composition which may form a cured film which has high surface hardness, excellent adhesion properties and excellent antifogging properties lasting a long time.
In order to achieve the above first object, the present invention provides a quaternary ammonium salt of the following formula (1).
wherein:
R
1
is CH
3
(CH
2
)
n
CH
2
or CH
3
(CH
2
)
n
CH
2
C
6
H
4
wherein n is an integer from 1 to 16 inclusive;
R
2
and R
3
are the same or different from each other, and represent CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
2
,CH
2
═CHCOOCH
2
CH(OH)CH
2
or H, with the proviso that R
2
and R
3
may not be H at the same time;
R
4
is H, CH
3
, CH
3
CH
2
or CH
3
CH
2
CH
2
; and
X is CH
3
OSO
3
, CH
3
CH
2
OSO
3
, CH
3
COO, CF
3
COO, CH
3
(CH
2
)
n
COO wherein n is an integer from 1 to 16 inclusive, CH
3
(CH
2
)
7
CH═CH(CH
2
)
7
COO, C
6
H
5
COO, C
6
H
5
CH(OH)COO, HOOCCH
2
CH(OH)COO, Cl or Br.
In order to achieve the second object, the present invention also provides a method for preparing a quaternary ammonium salt of the above formula (1) which comprises the following steps (a) to (d):
(a) reacting alkyiglycidyl ether or alkylphenylglycidyl ether with protected di-2-hydroxyethylamine to give a compound of the following formula (2):
 wherein:
R
1
is CH
3
(CH
2
)
n
CH
2
or CH
3
(CH
2
)
n
CH
2
C
6
H
4
wherein n is an integer from 1 to 16 inclusive; and
P is an alcohol protecting group;
(b) deprotecting the compound of the above formula (2);
(c) reacting the deprotected compound with glycidyl acrylate or glycidyl methacrylate; and
(d) reacting the resulting tertiary amine with a compound of the formula R
4
X to give the quaternary ammonium salt.
In order to achieve the third object, the present invention also provides an antifogging composition which comprises the following ingredients (a) to (d):
(a) about 3-about 40% by weight of a quaternary ammonium salt of the above formula (1);
(b) about 18-about 90% by weight of an oligomer containing at least two acrylic groups;
(c) about 5-about 40% by weight of a first monomer containing at least one acrylic group; and
(d) about 2-about 8% by weight of a radical photo-initiator.
In order to achieve the fourth object, the present invention also provides a hybrid antifogging composition which comprises the following ingredients (a) to (f):
(a) about 3-about 34% by weight of a quaternary annnonium salt of the above formula (1);
(b) about 4-about 81% by weight of an oligomer containing at least two acrylic groups;
(c) about 6-about 26% by weight of a first monomer containing at least one acrylic group;
(d) about 8-about 26% by weight of a second monomer containing at least one vinyl ether group;
(e) about 1-about 5% by weight of a cationic photo-initiator; and
(f) about 1-about 5% by weight of a radical photo-initiator.
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
The photo-curable antifogging composition of the present invention essentially includes a quaternary ammonium salt of the following formula (1), which has one or two acryl groups, three hydroxy groups, one quaternary ammonium salt group, and one n-alkyl or n-alkylphenyl group:
wherein:
R
1
is CH
3
(CH
2
)
n
CH
2
or CH
3
(CH
2
)
n
CH
2
C
6
H
4
wherein n is an integer from 1 to 16 inclusive;
R
2
and R
3
are the same or different from each other, and represent CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
2
,CH
2
═CHCOOCH
2
CH(OH)CH
2
or H, with the proviso that R
2
and R
3
may not be H at the same time;
R
4
is H, CH
3
, CH
3
CH
2
or CH
3
CH
2
CH
2
; and
X is CH
3
OSO
3
, CH
3
CH
2
OSO
3
, CH
3
COO, CF
3
COO, CH
3
(CH
2
)
n
COO wherein n is an integer from 1 to 16 inclusive, CH
3
(CH
2
)
7
CH═CH(CH
2
)
7
COO, C
6
H
5
COO, C
6
H
5
CH(OH)COO, HOOCCH
2
CH(OH)COO, Cl or Br.
The quaternary ammonium salt of the above formula (1) according to the present invention may be prepared by the following process.
Alkylglycidyl ether or alkylphenylglycidyl ether is reacted with protected di-2-hydroxyethylamine to give a compound of the following for

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