Cyanoacrylate compositions

Details Cyanoacrylate compositions Cyanoacrylate compositions

1999-11-23

2001-09-25

Szekely, Peter (Department: 1714)

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C156S331200, C156S331800, C524S377000, C524S753000, C524S762000, C526S194000, C526S204000, C526S208000, C526S209000

Reexamination Certificate

active

06294629

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to cyanoacrylate-containing compositions that include, in addition to the cyanoacrylate component, the combination of two accelerators to improve fixture speeds on certain substrates.
2. Brief Description of Related Technology
Cyanaoacrylate adhesive compositions are well known, and widely used as quick setting, instant adhesives with a wide variety of uses. See H. V. Coover, D. W. Dreifus and J. T. O'Connor, “Cyanoacrylate Adhesives” in
Handbook of Adhesives
, 27, 463-77, I. Skeist, ed., Van Nostrand Reinhold, New York, 3rd ed. (1990). See also, G. H. Millet “Cyanoacrylate Adhesives” in
Structural Adhesives: Chemistry and Technology
, S. R. Hartshorn, ed., Plenun Press, New York, p. 249-307 (1986).
Nonetheless, various techniques have been used to improve further the fixture times of such adhesive compositions for certain applications where it is important to be able to secure one substrate to another quickly, while allowing the bond strength to develop over time. In addition, substrates constructed of certain materials have proven in the past difficult to bond, irrespective of the application to which the adhesive and the substrate are to be placed.
To combat these issues, Loctite Corporation developed a technology based on calixarene and oxacalixarene compounds. Generally, the addition of such materials to a cyanoacrylate allow for accelerated fixturing of substrates to-be-bonded together. See U.S. Pat. Nos. 4,556,700, 4,622,414, 4,636,539, 4,695,615, 4,718,966, and 4,855,461.
In addition to calixarene compounds, Loctite Corporation also developed technology based on the addition of silacrown compounds to cyanoacrylate adhesive compositions to accelerate fixturing. For instance, U.S. Pat. No. 4,906,317 (Liu) is directed to cyanoacrylate adhesive compositions which include silacrown compounds as additives to give substantially reduced fixture and cure times on de-activating substrates such as wood. The silacrown compounds are preferably employed at levels of about 0.1-5% by weight of the composition.
More recently, Henkel KgaA developed technology based on the addition to cyanoacrylate compositions of cyclodextrins to accelerate fixturing. In U.S. Pat. No. 5,312,864 (Wenz), the acceleration of the setting properties of a cyanoacrylate adhesive composition by adding thereto a hydroxyl group derivative of an &agr;-, &bgr;- or &ggr;-cyclodextrin which is at least partly soluble in the cyanoacrylate is described.
Other approaches have also been investigated, such as in U.S. Pat. No. 4,837,260 (Sato), in which it is reported the use of crown ethers in cyanoacrylate adhesive compositions.
Notwithstanding the state-of-the-technology it would be desirable to provide alternative technologies to improve the fixturing speed of cyanoacrylates.
SUMMARY OF THE INVENTION
The present invention is directed to a cyanoacrylate-based composition, which includes beyond the cyanoacrylate component, two accelerator components, the combination of which demonstrates improved fixture speeds, particularly on substrates constructed of materials, such as certain woods, cotton and cork and combinations thereof.
The two accelerator components may be referred to herein as the first accelerator and the second accelerator, with the first accelerator selected from calixarenes and oxacalixarenes, silacrowns, crown ethers and cyclodextrins, and the second accelerator selected from poly(ethyleneglycol) di(meth)acrylates and ethoxylated hydric compounds.
This invention is also directed to a method of bonding together two substrates, at least one of which is constructed of a material, such as certain woods, cotton and cork, and combinations thereof. The method includes applying to at least one of the substrates a composition as described above, and thereafter mating together the substrates.
In addition, the present invention is directed to reaction products of the inventive compositions.
Also, the invention is directed to a method of preparing the inventive compositions.
The invention will be more fully understood by a reading of the section entitled “Detailed Description of the Invention”, which follows.
DETAILED DESCRIPTION OF THE INVENTION
As noted above, this invention is directed to a cyanoacrylate-based composition, which includes beyond the cyanoacrylate component, two accelerator components, the combination of which demonstrates improved fixture speeds, particularly on substrates constructed of a material, such as certain woods, cotton and cork, and combinations thereof.
The cyanoacrylate component includes cyanoacrylate monomers which may be chosen with a raft of substituents, such as those represented by H
2
C═C(CN)—COOR, where R is selected from C
1-15
alkyl, alkoxyalkyl, cycloalkyl, alkenyl, aralkyl, aryl, allyl and haloalkyl groups. Desirably, the cyanoacrylate monomer is selected from methyl cyanoacrylate, ethyl-2-cyanoacrylate, propyl cyanoacrylates, butyl cyanoacrylates (such as n-butyl-2-cyanoacrylate), octyl cyanoacrylates, allyl cyanoacrylate, &bgr;-methoxyethyl cyanoacrylate and combinations thereof. A particularly desirable one is ethyl-2-cyanoacrylate.
The cyanoacrylate component should be included in the compositions in an amount within the range of from about 50% to about 99.98% by weight, with the range of about 90% to about 99% by weight being desirable, and about 95% by weight of the total composition being particularly desirable.
The first accelerator may be selected from calixarenes and oxacalixarenes, silacrowns, crown ethers, cyclodextrins and combinations thereof.
Of the calixarenes and oxacalixarenes, many are known, and are reported in the patent literature. See e.g., U.S. Pat. Nos. 4,556,700, 4,622,414, 4,636,539, 4,695,615, 4,718,966, and 4,855,461, the disclosures of each of which are hereby expressly incorporated herein by reference.
For instance, as regards calixarenes, those within structure I are useful herein:
where R
1
is alkyl, alkoxy, substituted alkyl or substituted alkoxy; R
2
is H or alkyl; and n is 4, 6 or 8.
One particularly desirable calixarene is tetrabutyl tetra[2-ethoxy-2-oxoethoxy]calix-4-arene.
A host of crown ethers are known. For instance, examples which may be used herein either individually or in combination, or in combination with other first accelerators include 15-crown-5, 18-crown-6, dibenzo-18-crown-6, benzo-15-crown-5, dibenzo-24-crown-8, dibenzo-30-crown-10, tribenzo-18-crown-6, asym-dibenzo-22-crown-6, dibenzo-14-crown-4, dicyclohexyl-18-crown-6, dicyclohexyl-24-crown-8, cyclohexyl-12-crown-4, 1,2-decalyl-15-crown-5, 1,2-naphtho-15-crown-5, 3,4,5-naphtyl-16-crown-5, 1,2-methyl-benzo-18-crown-6, 1,2-methylbenzo-5, 6-methylbenzo-18-crown-6, 1,2-t-butyl-18-crown-6, 1,2-vinylbenzo-15-crown-5, 1,2-vinylbenzo-18-crown-6, 1,2-t-butyl-cyclohexyl-18-crown-6, asym-dibenzo-22-crown-6 and 1,2-benzo-1,4-benzo-5-oxygen-20-crown-7. See U.S. Pat. No. 4,837,260 (Sato), the disclosure of which is hereby expressly incorporated here by reference.
Of the silacrowns, again many are known, and are reported in the literature. For instance, a typical silacrown may be represented within the following structure (II):
wherein R
3
and R
4
are organo groups which do not themselves cause polymerization of the cyanoacrylate monomer, R
5
is H or CH
3
and n is an integer of between 1 and 4. Examples of suitable R
3
and R
4
groups are R groups, alkoxy groups such as methoxy, and aryloxy groups such as phenoxy. The R
3
and R
4
groups may contain halogen or other substituents, an example being trifluoropropyl. However, groups not suitable as R
4
and R
5
groups are basic groups such as amino, substituted amino and alkylamino.
Specific examples of silacrown compounds useful in the inventive compositions include:
dimethylsila-11-crown-4 (III);
dimethylsila-14-crown-5 (IV);
and dimethylsila-17-crown-6 (V). See e.g., U.S. Pat. No. 4,906,317 (Liu), the disclosure of which is hereby expressly incorporated herein by reference.
Many cyclodextrins may be used in connection with

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