Aromatic oligomer and use thereof

Details Aromatic oligomer and use thereof Aromatic oligomer and use thereof

2002-03-05

2004-03-30

Truong, Duc (Department: 1711)

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

Synthetic resins

From phenol, phenol ether, or inorganic phenolate

C528S137000, C528S144000, C528S159000, C525S480000, C525S502000

Reexamination Certificate

active

06713591

ABSTRACT:

This application is the national phase under 35 U.S.C. §371 of PCT International Application No. PCT/JP00/05881 which has an International filing date of Aug. 30, 2000, which designated the United States of America.
FIELD OF TECHNOLOGY
This invention relates to aromatic oligomers and uses thereof. The aromatic oligomers of this invention are useful as tackifiers to provide adhesive properties and incorporated in resins and rubbers in formulating adhesives, pressure sensitive adhesives and coatings. Moreover, the oligomers of this invention are useful as vibration damping agents effective in the range from room temperature to about 170° C. and incorporated in resins and rubbers for use in the industrial sectors that may cause problems relating to vibration and noise such as construction materials, electrical appliances, automobiles, bridges, motors, power generators and engines.
BACKGROUND TECHNOLOGY
Resins obtained by the reaction of phenols with formaldehyde compound in the presence of an acid catalyst are well known as phenolic resins or novolak resins. Likewise, resins obtained by the reaction of aromatic hydrocarbons such as xylene with formaldehyde compound in the presence of an acid catalyst are well known as hydrocarbon resins. Indene-cumarone resins and petroleum resins are also known as hydrocarbon resins; in this case, however, indene, cumarone and cyclopentadiene themselves possess olefinic bonds and formaldehyde compound is not used in the reaction.
The use of resin obtained by the reaction of an aromatic oil with formaldehyde compound in the presence of an acid catalyst as an ingredient in formulating coatings is described in Japanese patent publication JP53-24973 B(1978). Resin compositions formulated by incorporating naphthalene, methylnaphthalene and acenaphthene in phenolic resins are described in JP59-52887 B(1984), JP07-242719 A(1995) and JP08-157571 A(1996).
Tackifiers are often added to a variety of adhesives such as hot-melt adhesives, emulsion adhesives and pressure sensitive adhesives in order to improve the adhesive strength and raise the initial adhesive strength. For example, JP10-195047 A(1998) teaches the addition of a variety of tackifier resins to acrylic emulsion adhesives. JP10-158626 A(1998) and JP06-145626 A(1994) also teach the addition of a variety of tackifier resins to hot-melt adhesives derived from SBR-based block copolymers or modifications thereof by hydrogenation or epoxidation. Furthermore, WO95-12623 teaches the addition of a variety of tackifier resins to acrylic pressure sensitive adhesives. The aforementioned patents describe a relatively large number of tackifiers in common; for example, indene-cumarone resins, petroleum resins, rosin-derived resins, xylene resins, phenolic resins, terpene resins and styrene resins. These tackifier resins are suitably chosen in consideration of such factors as compatibility with the base resin or rubber, use conditions such as temperature and presence or absence of solvents. As for their performance, there are demands for improved adhesive strength and improved initial adhesive strength and, additionaly, suppressed generation of an offensive odor at use temperature and low price in the case of hot-melt adhesives.
A number of methods have been proposed for controlling vibration damping properties by the use of petroleum resins: for example, the use of commercially available petroleum resins and cumarone-indene resins reported in JP63-11980 A(1988) and JP62-141069 A(1987) and the use of commercially available polybutenes, terpene resins or modified rosin reported in JP02-49063 A(1990). The use of alkylbenzene-methylnaphthalene resins as an example of polycyclic aromatic resins is described in JP07-90130 A(1995).
A vibration damping agent to be incorporated in a base material such as rubber, resin and bitumen to improve vibration damping properties must desirably satisfy the following properties; the loss factor (tan &dgr;) of a vibration damping material in which the agent in question is incorporated is large in the use region and the temperature dependency of tan &dgr; is small. It is known, however, that these properties are often contrary to each other.
An object of this invention is to provide a novel aromatic oligomer which emits little or no odor. Another object of this invention is to provide a vibration damping agent which can be readily obtained. A further object of this invention is to provide a polycyclic vibration damping agent manifesting a high degree of vibration damping performance. A still further object of this invention is to provide a vibration damping agent which manifests excellent vibration damping performance in a wide temperature range.
DISCLOSURE OF THE INVENTION
This invention relates to an aromatic oligomer which is represented by the following formula (1);
(A—F)n—A   (1)
wherein A is a unit comprising (a) 30-90 wt % of an aromatic compound containing 2-4 rings and (b) 10-70 wt % of a phenol compound, F is methylene or a mixture of methylene and —CH
2
OCH
2
— and n is a number of 1-100.
This invention also relates to said aromatic oligomer wherein the oxygen content is 20% or less. Moreover, this invention relates to an aromatic oligomer resin which comprises said aromatic oligomer as the principal component.
Still more, this invention relates to said aromatic oligomer or said aromatic oligomer resin which is obtained by the reaction of 1 kind or 2 kinds or more of aromatic compounds selected from naphthalene, methylnaphthalene, dimethylnaphthalene, acenaphthene, fluorene, anthracene, phenanthrene, pyrene, benzothiopene and fluoranthene with 1 kind or 2 kinds or more of phenols selected from phenol and alkylphenols and 1 kind or 2 kinds or more of formaldehyde compound selected from formalin, formaldehyde and paraformaldehyde and exhibits a softening point of 50-180° C.
Also, this invention relates to a tackifier or a vibration damping agent comprising said aromatic oligomer or aromatic oligomer resin as an active ingredient.
Explanation will be given below to the method for preparing the aromatic oligomer or the aromatic oligomer resin which comprises said aromatic oligomer as the principal component and, at the same time, explanation will be given to the invention of the aromatic oligomer. It is to be noted that the aromatic oligomer to be obtained in accordance with the method of this invention is generally a mixture unless pure raw materials are used and may contain a resin which cannot be represented by general formula (1); however, the aromatic oligomer in question contains 50% or more, preferably 80% or more, of the resin represented by general formula (1) as the principal component. In this specification, % in respect to purity or concentration signifies wt % unless otherwise specified. The components in the aromatic oligomer actually mean the unit or radical derived from monomers such as an aromatic compound and a phenol existing in the oligomer; for the simplicity of explanation, however, the unit or radical present in the oligomer may often be simply described by the name of the monomer. The aromatic oligomer resin means a resin which comprises the aforementioned aromatic oligomer as the principal component, that is, in an amount of 50% or more, preferably 70% or more, more preferably 80% or more. It is to be understood here, for the simplicity of explanation, that “the aromatic oligomer” refers not only to the aromatic oligomer but also to the aromatic oligomer resin which comprises the aromatic oligomer as the principal component unless it makes a contradictory statement.
A compound useful for the aromatic compound is preferably the one that boils higher than naphthalene or a mixture of such compounds. Concretely, it is an aromatic compound consisting of an aromatic ring linked to one or more rings, the aromatic ring here being selected from 5- or 6-membered rings consisting entirely of carbon atoms, 5- or 6-membered rings consisting of one oxygen atom and carbon atoms and 5- or 6-membered rings consisting of one sulfur atom and carbon atoms, a

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