Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
1997-12-18
2002-05-14
Wu, David W. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
C526S346000, C526S348000, C526S319000, C526S327000
Reexamination Certificate
active
06388034
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an adhesive composition for metals, especially noble metals, and a method for adhering items using the same. The term “adhesive composition for metals” in this invention includes an adhesive composition for adhering a metal material to a metal material or to a non-metal material, and a metal surface treating material used for such adhesion. The adhesive composition according to the present invention is specifically useful in the field of dentistry.
BACKGROUND ART
In a wide variety of fields including dentistry, there has been a demand to strongly adhere an organic material to noble metals such as gold, platinum and palladium or an alloy mainly containing such noble metals. Specifically in the field of dentistry, use of noble metal alloys for crowns, inlays, etc. is indispensable, and thus an adhesive usable for these noble metal alloys has been demanded. Conventionally, such an adhesive cannot be found. Accordingly, the above-described adhesion needs to be done by a method of roughening a surface of the item to be adhered using sandblast or the like and causing the item to stick via the roughened surface by a mechanical engagement force or a method of coating the surface of the noble metal with a base metal by tin electrodeposition or the like and then adhering the items via the base metal surface. It has been pointed out that these methods have problems of being troublesome and providing a level of durability insufficient to realize long-term adhesion.
Recently, by the suggestion that a compound containing sulfur is effective in order to solve the above-mentioned problems, various types of adhesives for noble metals containing sulfur have been proposed. Examples of such sulfur compounds include triazinethiol group-containing compounds, the triazine having a thiol substituent (Japanese Laid-Open Publication No. 62-292774), mercapto group- or polysulfide group-containing compounds (Japanese Laid-Open Publication No. 63-225674), triazine-dithion derivative-containing compounds (Japanese Laid-Open Publication No. 64-83254), thiophosphoric acid group-containing compounds (Japanese Laid-Open Publication No. 64-90276), and dichlorothiophosphoryl group-containing compounds (Japanese Laid-Open Publication No. 5-117595). It has been reported that these compounds have a significant level of adhesiveness at the laboratory level. However, these compounds still have problems in stability in storage and long-time adhesion durability, and also require a long period of time for adhesion. Thus, these compounds are not satisfactory for practical use.
DISCLOSURE OF INVENTION
As a result of active studies in order to solve the above-described problems, the present inventors have found that all the above-described problems are solved by using a compound containing a thiirane group and an olefin-type double bond. Based on this discovery, the present inventors developed the present invention.
An adhesive composition for metals according to the present invention includes an unsaturated thiirane compound having at least one thiirane group bonded with a saturated carbon atom and having at least one olefin-type double bond.
In a preferred embodiment of the invention, the unsaturated thiirane compound is represented by general formula I:
where R
1
is a group represented by
or general formula (II),
R
2
is an organic group having a carbon number of 1 through 40, and each of R
3
and R
4
is independently an organic group having a carbon number of 1 to 40, hydrogen, a thiirane group, or halogen, R
5
is hydrogen or a methyl group, X is —COO—, —OOC—, —CONH—, —NHCO—, or —O—, and each of n and m is independently 0 or 1, wherein in the case where at least one of R
3
and R
4
is an organic group, at least two of R
2
, R
3
and R
4
can be bonded to each other to form a cyclic structure.
In a preferred embodiment of the invention, the adhesive composition for metals further includes an unsaturated olefin-type compound having at least one acid group.
In a preferred embodiment of the invention, the adhesive composition for metals is usable for adhesion of a noble metal or a noble metal alloy.
The present invention provides a method for adhering a first item having at least a metal surface portion and a second item which is intended to be adhered to the metal surface portion. The method includes the step of contacting the metal surface portion of the first item and the second item to each other via the adhesion composition for metals according to claim 1 and curing the composition.
In a preferred embodiment of the invention, the metal surface portion is formed of a noble metal or a noble metal alloy.
BEST MODE FOR CARRYING OUT THE INVENTION
An adhesive composition for metals according to the present invention contains an unsaturated thiirane compound having at least one thiirane group bonded with a saturated carbon and at least one olefin-type double bond. Such an unsaturated thiirane compound is not limited to any specific compound but various compounds can be used as the unsaturated thiirane compound. A compound having the general formula I shown below is preferable.
where R
1
is a group represented by
or general formula (II),
R
2
is an organic group having a carbon number of 1 through 40, and each of R
3
and R
4
is independently an organic group having a carbon number of 1 to 40, hydrogen, thiirane group, or halogen. In the case where at least one of R
3
and R
4
is an organic group, at least two of R
2
, R
3
and R
4
can be bonded to each other to form a cyclic structure. R
5
is hydrogen or a methyl group, X is —COO—, —OOC—, —CONH—, —NHCO—, or —O—. Each of n and m is independently 0 or 1.
In this description, the term “organic group” refers to a group described by (i) or (ii) below.
(i) Hydrocarbon group or substituted hydrocarbon group. Exemplary substituents in the substituted hydrocarbon group include halogen, a hydroxyl group, a carboxyl group, and a thiirane group.
(ii) Hydrocarbon group or substituted hydrocarbon group containing at least one hetero linking group in a main chain thereof. Exemplary hetero linking groups include —O—, —CO—, —S—, —SO—, and —NH—. Two or more types of hetero linking groups can be included. The definition of the substituted hydrocarbon group is the same as the definition of the substituted hydrocarbon group in (i) above.
Exemplary cyclic structures obtainable by bonding at least two of R
2
, R
3
and R
4
include an alicyclic group, an aromatic group, and a hetero alicyclic group; e.g., a cyclohexane ring, a benzene ring, and various spiroalicyclic groups.
Preferable compounds usable in the present invention among the unsaturated thiirane compounds represented by general formula I include a thiirane group-containing (meth)acrylate compound represented by formula III and a thiirane group-containing vinyl benzoate compound represented by formula IV:
where R
5
is hydrogen or a methyl group, and o is an integer of 1 through 41.
where p is an integer of 1 through 41.
An unsaturated thiirane compound used in the present invention can be synthesized by a usual method. Some examples will be described below.
i) A compound represented by formula I, in which X is —COO—and m is 1
Such a compound can be synthesized by a plurality of methods, and typically by the steps shown below.
In scheme A, R
1
through R
4
and n are defined in the same manner as in formula I, and Y is halogen.
As shown in scheme A, first, vinyl group-containing alcohol represented by V is epoxidized to obtain an epoxy group-containing alcohol of VI. Next, through reaction with acid halide (R
1
COY), a compound of VII is obtained. Then, through reaction with thiourea or the like, a thiirane group-containing compound represented by VIII is obtained.
For example, 9,10-epithiodecyl methacrylate (a compound represented by formula VIII, in which R
1
is CH
2
=C(CH
3
)—, R
2
is —CH
2
—, each of R
3
and R
4
is H, and n is 7) as an unsaturated thiirane compound can be prepared in the following manner. First, 9-decen-1-ol as a vinyl group-containing al
Kadoma Yoshinori
Nakanishi Tomomi
Ohta Tetsuro
Choi Ling-Siu
Kanebo Limited
Snell & Wilmer LLP
Wu David W.
LandOfFree
Metal adhesive compositions and method of bonding articles... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Metal adhesive compositions and method of bonding articles..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Metal adhesive compositions and method of bonding articles... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2849463