Water and oil-repellent resin composition

Details Water and oil-repellent resin composition Water and oil-repellent resin composition

1999-05-07

2001-05-01

Nutter, Nathan M. (Department: 1711)

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

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S116000, C525S199000

Reexamination Certificate

active

06225405

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to water and oil repellent resin compositions, molded articles thereof, and a process for producing such molded articles. More particularly, it relates to resin compositions wherein specific perfluoroalkyl group-containing polymers are blended with thermoplastic resins or thermosetting resins, and to resin molded articles having excellent water and oil repellency obtained by molding such compositions, and a process for producing the same. In particular, the resin compositions of the present invention have excellent stain resistance, and are suitable for producing molded products undergoing severe adhesion of dirt such as kitchen wares, bathroom wares and the like.
DESCRIPTION OF THE RELATED ART
As means to impart liquid-repellency to the surface of resins, those methods are conventionally used in which, for example, (1) the surface of molded products is coated with compounds having a low surface tension or (2) compounds having a low surface tension are melt blended with the resins. It is desired, if possible, in terms of both the process and the practical use to impart the liquid repellency by the above method (2), since the method (1) requires an additional proofing process in which the products once molded are further processed, and the compounds used for coating the surface are easily exfoliated by friction or other causes to lose their effects over time.
As compounds having a low surface tension, fluorine compounds are well known, and perfluoro-compounds are preferred among others. When commercially available perfluoroalcohols, perfluorocarboxylic acids, or esters derived therefrom are compounded as they are in resins, the water and oil repellency is not necessarily imparted, or shows poor durability although it is temporarily imparted.
For this reason, in Japanese Patent Publication (Kokai) Nos. H-7745 and H3-41162, homopolymers or copolymers of acrylic esters having perfluoroalkyl groups were melt kneaded with thermoplastic resins or olefin resins to increase the liquid repellency of the resins. The property modifications of thermoplastic resins according to such prior art, however, have some drawbacks in that, for example, it is difficult to obtain products having an adequate liquid repellency, or the oil repellency can not be developed even though the water repellency can be attained.
SUMMARY OF THE INVENTION
An object of the present invention is to provide water and oil repellent resin compositions which do not have the drawbacks of prior art as described above, as well as molded articles thereof and a method of molding the same.
To achieve the above object, the present invention provides (i) a resin composition comprising 100 parts by weight of a thermoplastic resin or a thermosetting resin and 0.1 to 5 parts by weight of at least one perfluoroalkyl group-containing polymer selected from the group consisting of a copolymer of a (meth)acrylic ester having a perfluoroalkyl group of 5-18 carbon atoms and a (meth)acrylic ester having a hydrophilic group, a homopolymer of an epoxy compound having a perfluoroalkyl group of 5-18 carbon atoms, and a copolymer of said epoxy compound and a monomer copolymerizable therewith, (ii) a process for producing a resin molded article, comprising molding said resin composition followed by heat treatment at 70-130° C., and (iii) a resin molded article produced by the above process.
DETAILED DESCRIPTION OF THE INVENTION
Examples of the (meth)acrylic ester having a perfluoroalkyl group of 5-18 carbon atoms used in the present invention include (meth)acrylic esters having a linear or branched perfluoroalkyl group such as
CH
2
═CHCOOC
2
H
4
C
6
F
13
,
CH
2
═C(CH
3
)COOC
2
H
4
C
6
F
13
,
CH
2
═CHCOOC
2
H
4
C
8
F
17
,
CH
2
═C(CH
3
)COOC
2
H
4
C
8
F
17
CH
2
═CHCOOC
2
H
4
C
16
F
33
,
CH
2
═C(CH
3
)COOC
2
H
4
C
16
F
33
,
CH
2
═CHCOOC
3
H
6
(CF
2
)
6
CF(CF
3
)
2
,
CH
2
═C(CH
3
)COOC
3
H
6
(CF
2
)
6
CF(CF
3
)
2
,
CH
2
═CHCOOC
3
H
6
(CF
2
)
10
CF(CF
3
)
2
,
CH
2
═C(CH
3
)COOC
3
H
6
(CF
2
)
6
CF(CF
3
)
2
,
CH
2
═CHCOOC
2
H
4
N(C
2
H
5
)SO
2
(CF
2
)
6
CF
3
, and
CH
2
═C(CH
3
)COOC
2
H
4
N(C
2
H
5
)SO
2
(CF
2
)
6
CF
3
.
Among others, (meth)acrylic esters of 8-12 carbon atoms are preferred. These esters may be used singly or in combination with one or more other such esters.
Examples of the hydrophilic group in the (meth)acrylic ester having a hydrophilic group include hydroxyl, polyethylene glycol, polypropylene glycol, and carboxyl groups as well as carbonium salts.
Specific examples of the (meth)acrylic ester having a hydrophilic group include:
CH
2
═CHCOO(CH
2
CH
2
O)
8
H,
CH
2
═C(CH
3
)COO(CH
2
CH
2
O)
10
H,
CH
2
═CHCOO(C(CH
3
)HCH
2
O)
10
H,
CH
2
═C(CH
3
)COOCH
2
CH
2
OH,
CH
2
═CHCOOCH
2
CH(OH)CH
2
OH,
CH
2
═C(CH
3
)COOCH
2
CH(OH)CH
2
Cl, and
CH
2
═CHCOOCH
2
CH
2
OH.
The weight ratio of the (meth)acrylic ester having a perfluoroalkyl group to the (meth)acrylic ester having a hydrophilic group in the copolymer is 1:10 to 10:1, and in particular, 1:2 to 2:1.
In addition to these two essential monomers, at least one of third monomers copolymerizable with such monomers may be used in the copolymerization in an amount such that the liquid repellency is not impaired.
Examples of such third copolymerizable monomer include vinyl acetate, vinyl chloride, styrene, &agr;-methylstyrene, (C
1
-C
25
)alkyl esters of (meth)acrylic acid, (C
6
-C
30
)aromatic esters of (meth)acrylic acid, and (meth)acrylic acid amides.
Since the liquid repellency of the copolymer increases as the amount of the third monomers decreases, the third monomer(s) may be used in an amount from 0 to 50% by weight based on the total amount of the two essential monomers described above, especially in view of the oil-repellency. More preferably, the third monomers are not used.
Depending on the intended liquid, however, use of such third monomers may strengthen the anchor effect to resins and result in an increased durability of the liquid repellency. In such cases, long chain (8-22 carbon atoms) alkyl esters of (meth)acrylic acid are preferred as the third monomers.
The mode of polymerization for the preparation of perfluoroalkyl group-containing polymers using such monomers may be any one of bulk polymerization, solution polymerization, suspension polymerization, and emulsion polymerization, and in addition to thermal polymerization, other methods such as photopolymerization or radiation polymerization can also be adopted. As a polymerization initiator, a known polymerization initiator such as an organic azo compound, a peroxide, or a persulfate may be used.
The molecular weight of the copolymer is preferably 1,000 to 1,000,000, and more preferably 2,000 to 10,000, since a lower molecular weight decreases the durability of the water and oil repellency although the initial water and oil repellency increases, while a higher molecular weight decreases the water and oil repellent function because of decrease in the bleeding out property towards the surface.
A molecular weight can be easily regulated using commercially available chain transfer agents (e.g., mercaptan, &agr;-methylstyrene, carbon tetrachloride, etc.).
Epoxy compounds having a perfluoroalkyl group of 5-18 carbon atoms used in the present invention may be exemplified by the compounds of the following general formula:
(wherein n is 0, 1 or 2 and Rf represents a perfluoroalkyl group having 5-18 carbon atoms), and specific examples may be:
Examples of the monomer which is copolymerizable with the epoxy compound having a perfluoroalkyl group include cyclic acid anhydrides such as succinic anhydride, maleic anhydride, phthalic anhydride, and acetic anhydride, cyclic ethers such as tetrahydrofuran and oxetane, cyclic formals such as dioxolane and trioxane, and cyclic epoxides such as propylene oxide, styrene oxide, and epichlorohydrin. The amount of the copolymerizable monomer is 90% by weight or less of the copolymer, for example, in the range of 10-80% by weight.
The homopolymerization

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