JPS6239A - Novel substituted aromatic hydrocarbon, production and use thereof - Google Patents

Abstract

NEW MATERIAL:An aromatic hydrocarbon having at least one nuclear hydrogen atom substituted by a lower alkyl-substituted or unsubstituted tetracyclo [6, 2, 1, 1, 3, 6, 0, 2, 7]dodeca-4-yl group or tetracyclo[6, 2, 1, 1, 3, 6, 0, 2, 7]dodecca-5-yl group. EXAMPLE:9-Methyl-tetracyclo[6, 2, 1, 1, 3, 6, 0, 2, 7]dodeca-4-ylbenze-ne. USE:An additive (softener) for adhesives and power transmission medium. PREPARATION:An aromatic hydrocarbon is reacted with a compound expressed by the formula (R<1> is lower alkyl at the 3-6-position or 12-position; R<2> is lower alkyl at the 1-2-position or 7-11-position; n is an integer 0-5; m is an integer 0-7) at 1:1.2-10 molar ratio, as necessary, in the coexistence of a reaction solvent, e.g. pentane or chlorobenzene, in the presence of a Friedel-Crafts type catalyst, preferably AlCl3, at 0-150 deg.C for 1-10hr to afford the aimed com pound.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to novel substituted aromatic hydrocarbons, a method for producing the same, and additives for adhesives and power transmission media using the same. More specifically, novel substituted aromatic hydrocarbons in which a tetracyclododecyl group is substituted with a nuclear hydrogen atom, a method for producing the same, and an additive as a softener or tackifier for adhesives using the same, and furthermore Related to power transmission media.

[Technical background of the invention]

The present inventor has discovered that tetracyclo [e, z, x, t, "o2'
7] In the course of research on aromatic hydrocarbon derivatives using -4-dodecenes, the tetracyclo[e
, 2. x, 1? 'o'']-4-dodecenes react with aromatic hydrocarbons to give novel substituted aromatic hydrocarbons, and that the novel substituted aromatic hydrocarbons can be used as additives for adhesives, i.e. as softeners or The present inventors have discovered that it is extremely useful as a tackifier, etc., and have completed the present invention.

[Summary of the invention]

Therefore, the first aspect of the present invention is that at least one nuclear hydrogen atom of the aromatic hydrocarbon is the following lower alkyl substituted or unsubstituted tetracyclo(6,2,1,1 01'') dodec-4-yl Base CI
) or tetracyclo(6,2,1,tF'o”)
] New substituted aromatic hydrocarbons substituted by a dodecyl 5-yl group n).

However, R1 is a lower alkyl group located at the 3rd to 6th and 12th positions, and n R1's are the same or different.

R2: A lower alkyl group located at the 1st to 2nd positions and the 7th to 11th positions, and m R2's are the same or different.

n: an integer of 0 to 5 m: an integer of θ to 7 The second aspect of the present invention relates to a method for producing such novel substituted aromatic hydrocarbons, the novel wl-substituted aromatic hydrocarbons, aromatic hydrocarbons and lower alkyl substituted or unsubstituted tetracyclo(6,2
, 1, bi"0"')-4-dodecene in the presence of a Friedel-Krach type catalyst.

(However, R', R2, n, and ms are the same as defined above.) The third aspect of the present invention is an additive for adhesives comprising such novel substituted aromatic hydrocarbons.

The fourth aspect of the present invention is a power transmission medium made of such novel substituted aromatic hydrocarbons.

[Manufacturing raw materials]

Examples of aromatic hydrocarbons that are raw materials for producing one of the novel substituted aromatic hydrocarbons according to the present invention include benzene,
Naphthalene, anthracene, and various alkyl group substituted products of these, specifically toluene, 0-xylene, m-xylene, baraxylene, ethylbenzene, n
-Propylbenzene, isopropylbenzene, 0-ethyltoluene, m-ethyltoluene, p-ethyltoluene, n-butylbenzene, isobutylbenzene, 5ec-
Examples include butylbenzene, t-butylbenzene, various diethylbenzenes, 1-methylnaphthalene, 2-methylnaphthalene, and 9-methylanthracene.

Other aromatic hydrocarbons include biphenyl, terphenyl, indane, and the like. Among these aromatic hydrocarbons, monoalkyl-substituted benzenes are preferred, with toluene and ethylbenzene being particularly preferred.

Tetracyclo [s, 2. T-t! '6o'']-4-dodecene is preferably unsubstituted, but in addition, 1 to 12
Those in which at least one position is substituted with a lower alkyl group, such as a methyl group, ethyl group, propyl group, isopropyl group, or butyl group, are used. The substitution position of the lower alkyl group includes, for example, mono-substitution such as the 9-position, and di-substitution such as the 9- and 10-position, but is not limited to these.

Such tetracyclo(6,2,1,1,0)-4-dodecenes can be easily produced by a known method by condensation of norbornenes and cyclopentagenes. Although it is preferred that the material be pure when used in the present invention, raw materials having a purity of about 60% by weight or greater can be used. In this case, other raw material components are preferably non-polymerized components, but 2-methyl-
norbornenes such as norbornene, cycloalkenes such as methylcyclopentene, methylcyclohexene,
9-Methyl-tricyclo(5,2,1,0″)deca-3
-tricyclo(5,2,1,05]deca-3 like ene
- Polymerizable components such as enes may be included.

When these polymerizable components are present in the raw materials, they become te.

Tracyclo [s, 2. x, t'jo"]-4-dodecenes, it may react with aromatic hydrocarbons, so the novel substituted aromatic hydrocarbons according to the present invention cannot be obtained in pure form. However, this In this case, the novel substituted aromatic hydrocarbons can be used in tackifiers, etc., which will be described later.

The reaction is carried out in a molar ratio of about 1 to 50 to the aromatic hydrocarbons.
double the amount, preferably about 1.2 to 10 times the amount of tetracyclo(
6,2,1,1"', 0"") -4-dodecenes, and if necessary, coexistence of a reaction solvent such as pentane, hexane, heptane, dichloromethane, ethyl chloride, 1,2-dichloroethane, chlorobenzene, etc. Below, Friedel-
It is carried out using a Krach type catalyst.

As a Friedel-Krauch type catalyst, for example, AlCl
3, AlBr+, BF3.5nC14, SnBr4
, FeCla, BeCl2, CdCl2, ZnCl2,
BF13, Bar 3, TiCl4, TiBr5, Z
Complexes of Lewis acids such as rC15, alkyl aluminum dichlorides, complexes of BF3 with alcohols, phenols, and ethers, and ternary complexes of AlCl3 with aromatic hydrocarbons and hydrogen halides are used, among which BF3, AlCl3 or complexes thereof are preferably used.

The amount of these catalysts used varies depending on the type of catalyst, the type and purity of both reaction raw materials, reaction temperature, etc., but generally it is about 1 to 50 mol% of the aromatic hydrocarbons that are the reaction raw materials. used.

The reaction is generally carried out at a temperature of about -10 to 200°C, preferably about O to 200°C.
At a temperature of 150°C, under normal pressure or pressurized conditions, about 1 to 1
Runs for 0 hours. As for the order of operation, first, both the reaction raw materials and the reaction solvent used as necessary are maintained at a predetermined temperature and pressure, and a catalyst is added while stirring to start the reaction. After reacting for a specified time,
The remaining catalyst is removed according to a conventional method, and the unreacted components and reaction solvent are removed by distillation to obtain the target substituted aromatic hydrocarbons in the first step. In addition, tetracyclo[6,2,1,1'';0
Since 4-dodecene ()-4-dodecene hardly polymerizes by itself, the target substituted aromatic hydrocarbons can be obtained with relatively high purity.

[Examples of new substituted aromatic hydrocarbons]

Examples of the novel substituted aromatic hydrocarbons obtained in this way include the following. However, tetracyclo(6,2,1,t?'o”]]dodecar-4-yl or tetracyclo(6,2,1,1,0)
The dodec-5-yl group can be simply replaced with X and 9-tetracyclo(
6,2,1,1,0) dodeca-4-(or 5-buyl group simply with Y, 9-ethyltetracyclo[s, 2.t,
T! Dodeca-4-(or 5)yl [Application invention/Adhesive additive] The novel substituted aromatic hydrocarbons (hereinafter sometimes abbreviated as A) of the present invention can be used in hot melt adhesives. It has excellent properties as an additive for pressure-sensitive adhesives, such as a tackifier and a softener.

Adhesive compositions generally include hot-melt adhesives that are made by blending a base resin such as ethylene/vinyl acetate copolymer with a tackifier and, if necessary, wax and other additives, as well as natural rubber, synthetic rubber, etc. There are pressure-sensitive adhesives that are made of a base resin mixed with a tackifier and, if necessary, a solvent and other additives. The former hot melt adhesive is generally used as an adhesive or coating agent in the fields of bookbinding, can manufacturing, woodworking, lamination, sheeting, coating processing, etc. Moreover, the latter pressure-sensitive adhesive is generally coated on a base material such as paper, cloth, or plastic film for use in adhesive tapes, labels, and the like. In each of these adhesive compositions, a tackifier is blended with the base resin. In particular, in the case of hot melt adhesives, in addition to compatibility with base resins such as ethylene/vinyl acetate copolymer and wax, adhesion, melt viscosity, and flexibility, heat stability, tip stability, Good things such as hue are required.

On the other hand, in the case of tackifiers for pressure-sensitive adhesives, they must have excellent compatibility with base resins such as natural rubber and synthetic rubber, have good solubility in solvents, and be chemically stable. It is required to have properties such as excellent weather resistance, good hue, and no strong odor.

When A according to the present invention is used as a tackifier or softener in a pressure-sensitive adhesive, specific examples of the base resin include natural rubber, styrene-butadiene copolymer rubber, polybutadiene, polyisoprene, Polyethylene sobutylene, butyl rubber, polychloroprene, ethylene,
Propylene copolymer rubber, ethylene/propylene/α-olefin copolymer rubber, ethylene/propylene/diene copolymer rubber, styrene/butadiene/styrene block copolymer, styrene/isoprene/styrene block copolymer, hydrogenated styrene/butadiene - Comb-like polymers such as styrene block copolymer (SEBS) and hydrogenated styrene/isoprene/styrene block copolymer are used. Particularly preferred are styrene/butadiene/styrene block copolymers, styrene/isoprene/styrene block copolymers, and hydrogenated copolymers thereof.

In addition, when used as a tackifier or softener for hot melt adhesives, specific examples of the base resin include ethylene/vinyl acetate copolymer, polyethylene, polypropylene, ethylene/propylene copolymer, Ethylene/acrylic acid copolymer, ethylene/acrylic acid ester copolymer, polyester, polyamide, polyvinyl acetate, etc. are used. In the case of hot melt adhesive compositions, it is particularly preferred to use ethylene/vinyl acetate copolymers and ethylene/acrylic acid ester copolymers as the base resin.

When A according to the present invention is used as a tackifier, the blending ratio with the base resin varies somewhat depending on the hot melt adhesive composition and the pressure sensitive adhesive composition. In the case of a hot melt adhesive composition, the blending ratio of the tackifier is usually 20 to 300 parts by weight, preferably 30 to 200 parts by weight, based on 100 parts by weight of the base resin. In some cases, it is usually 20 parts by weight per 100 parts by weight of the base resin.
It ranges from 30 to 200 parts by weight, preferably from 30 to 150 parts by weight. Similarly, when used as a softener, the blending ratio with the base resin is usually 2 to 30 parts by weight per 100 parts by weight of the base resin in the case of hot melt adhesive compositions, and 100 parts by weight of the base resin in the case of pressure sensitive adhesives. It is usually in the range of 10 to 200 parts by weight. For any type of adhesive, if A is used as the tackifier, other softeners listed below may be used, or if A is used as the softener, other tackifiers such as rosin and its derivatives may be used. , terpene resin, alicyclic resin,
Aliphatic resins, aromatic resins, aliphatic-aromatic copolymer resins, etc. may also be used.

In addition to the tackifier or softener and the essential components of the base resin, the adhesive composition using A according to the present invention also contains:
Various additives are blended as necessary. For example, in the case of a hot melt adhesive composition, softeners such as dioctyl phthalate and dibutyl phthalate, waxes such as petroleum-based paraffin wax with a melting point of about 40 to 65°C, polyolefin wax, microwax, and phenol-based Alternatively, antioxidants such as bisphenol-based organic compounds and metal soaps may be mentioned. In the case of pressure-sensitive adhesives, dioctyl phthalate, dibutyl phthalate, machine oil, process oil, softeners such as polybutene, fillers such as calcium carbonate, zinc white, titanium oxide, silica, amines, ketone-amines, etc. system,
Examples include phenol-based anti-aging agents and stabilizers. The blending ratio of these additives is arbitrary and appropriate.

The method for preparing an adhesive composition using A according to the present invention differs depending on whether it is a hot melt adhesive composition or a pressure sensitive adhesive. As a method for preparing a hot melt adhesive composition, a mixture consisting of tackifier A, the base resin, and optionally the various additives described above is stirred under heating to prepare a uniform melt. This is then cooled and formed into granules, flakes, pellets, rods, etc. depending on the application. This hot melt adhesive composition is again used for melting or coating. For example, when used for bonding purposes, a rod-shaped compound is used to fill a welding gun in corner bonding of molded products. On the other hand, as a method for preparing a pressure-sensitive adhesive, a mixture consisting of A according to the present invention as a tackifier, the above-mentioned base resin, and optionally the above-mentioned various additives is kneaded on a roll, or a suitable It can be prepared by conventional methods such as dissolving in a suitable solvent.

When a hot melt adhesive composition is used as an adhesive or a coating agent in an adhesive composition using A according to the present invention, A according to the present invention has excellent compatibility with the base resin and has high heat resistance stability. , color and odor, a uniform hot melt adhesive composition can be obtained, and this hot melt composition has excellent heat resistance stability and color, and moreover, the hot melt composition KJ! It has the advantage of having less odor when manufactured and used. Furthermore, even if A of the present invention is used in a pressure-sensitive adhesive composition, the hydrocarbon resin of the tackifier has excellent weather resistance in addition to the above-mentioned characteristics, so that a uniform pressure-sensitive adhesive composition can be obtained. This pressure-sensitive adhesive composition has the advantage of being excellent in color and weather resistance, and having little odor.

The adhesive composition using the hydrogenated substituted aromatic hydrocarbon A of the present invention will be specifically explained later with reference to Examples.

[Application invention/power transmission medium]

The novel hydrogenated substituted aromatic hydrocarbon A of the present invention has excellent properties as a power transmission medium in various mechanical devices.

As described in Japanese Patent Publications No. 53-36105, Japanese Patent Publication No. 46-338, Japanese Patent Publication No. 46-339, and Japanese Patent Publication No. 35763-1987, various substances are used as power transmission media for various devices. It's being used. As described in these publications, there are various characteristics required for a power transmission medium, but traction oil is a medium used in variable speed power transmission systems that utilize traction drives or traction friction clutches. For example, there is a need for something that can prevent wear and seizure of the contact parts between the driving side and the driven side, and also be able to transmit power efficiently.

A traction coefficient (=traction (frictional force)/normal load) is used as an index of such power transmission efficiency, and a vehicle with a high coefficient is desired. The use of a lubricating oil (traction oil) with a high traction coefficient provides large traction, which contributes to reducing fuel consumption in automobiles, etc., and also leads to extending the life of the transmission because the normal load is small. has a high traction coefficient and is excellent as a power transmission medium. A of the present invention may be used alone or in combination of two or more.

Among A of the present invention, particularly preferred are those in which one XSY or Z is bonded to a cyclohexane ring, or those in which one X, Y, or Z is bonded to a methylcyclohexane ring.

The power transmission medium using A of the present invention may consist only of A, but other lubricating oils may be added to satisfy various required properties and functions, and additives that are usually added may also be used. , even if they contain antioxidants, dispersants, metal deactivators, viscosity index improvers, anti-wear agents, rust inhibitors, corrosion inhibitors, foam inhibitors, seal swellers, friction modifiers, etc. good.

The performance of A of the present invention as a power transmission medium will be shown in Examples below.

In Examples, the general properties of A were evaluated by the following method.

(1) Softening point JIS K-5665 (2) Hue ASTM D 1544-58T Gardner number (G, No).

(3) Molecular weight Measured by field desorption ionization mass spectrometry.

(4) Refractive index Measured at 25°C using an Atsube refractometer.

(5) Viscosity: 2
Measured at 5°C.

(6) Number average molecular weight (%), molecular weight distribution (-/Mn) Calculated based on polystyrene using gel permeation chromatography.

Example 1 Four-day flask (5
00 mJ) with 195 g (2.5 mol) of benzene and Al
1.0 g of Cl3 powder was collected under a nitrogen atmosphere and stirred. 9-methyl-tetracyclo [s, 2. t, 1":o"']-4-dodecene 78g
(0.5 mol) was added dropwise from the dropping funnel over about 30 minutes while maintaining the temperature at 60°C. Thereafter, the reaction was continued at 60° C. for 1.5 hours, and then the catalyst was decomposed with methanol and washed with water. Unreacted substances were removed by distillation, and distillation was performed under reduced pressure to reduce the boiling point to 182-
Colorless fraction 15.184°C 15mmHg. Obtained Og (
n Hl, 4940). This one has a molecular weight of 252 (
Theoretical value 252), and the absorption of monosubstituted benzene by infrared absorption spectrum (760,705 cm"), 9-
It turned out to be methyl-tetracyclo(6,2,1,1,0) dodec-3(or 4)-ylbenzene. Further, a gel permeation chromatogram is shown in FIG.

Example 2 In the same flask as in Example 1, 50 g of toluene and AlCl3 were added.
1.3 g of powder was collected and stirred under a nitrogen atmosphere. 9
-Methyltetracyclo[6,2,1,1!゛402.7
102 g of -4-dodecene, 70.5 g of toluene, and Log of n-decane were added dropwise over about 30 minutes using a dropping funnel while maintaining the reaction temperature at 60°C, and then added for 1.5 hours to 6
The reaction was continued at 0°C. As a result of gas chromatography analysis at this point, 9-methyl-tetracyclo(6,2,1,1,0)-
100% of 4-dodecene and 31% of toluene were reacted. The reaction solution was washed with water and concentrated, resulting in a liquid resin of 140%
g was obtained (n 1.5591). As a result of analysis by gel permeation chromatography, 9-methyl-
Tetracyclo r-6,2,x,1"-to"+ -4-
73.5% mono-substituted dodecene, 13.6% disubstituted dodecene
, 9-methyl-tetracyclo [a, 2. t, 13'o=
]-4-Dodecene dimer (1.9%) and polymer (11.0 parts). IR of the above liquid resin
The measurement results are shown in Figure 3.

Example 3 In the same flask as in Example 1, 65 g of toluene, 65 g of n-decane, and 2.7 g of AlCl3 powder were collected under a nitrogen atmosphere and stirred. 9-methyltetracyclo(6,
2,1,1 6o2''F) -4-dodecene 100g
was added dropwise from the dropping funnel over about 30 minutes while maintaining the reaction temperature at 60 dodecene. The reaction was continued at 60° C. for an additional 1.5 hours.

The reaction solution was washed with water and concentrated, resulting in a softening point of 90°C and a hue of 6.
A solid resin of No. 5 was obtained. Ron 354゜ book/M mouth 1.
It was 2. As a result of analysis by gel permeation chromatography (Fig. 4), 9-methyl-tetracyclo[e, 2.1. T? 'o”]-]4-decene 1-substituted product 1
96%, disubstituted product 29.4%, trisubstituted product 32. sound%
, 16.3% high molecular weight fraction and 2.2% dimer of 9-methyl-tetracyclo(6,2,1,1!-'021')-4-dodecene.

Example 4 115 g of toluene, (1,2
5 mol) and 0.5 g of AlCl powder were stirred under a nitrogen atmosphere, and 9-ethyl-tetracyclo[6,2,1,1! 'b02・7]-4-dodecene 4
7.5 g (0.25 mol) was added over about 30 minutes while maintaining the temperature at 60'C, and the reaction was continued for an additional 1.5 hours. The catalyst was decomposed with methanol, washed with water, and concentrated under final stirring conditions of 21 mHH at 230 DEG C. to remove unreacted supernatant to obtain 69.1 g of liquid resin (n = 1.5461).

As a result of analysis by gel permeation chromatography, 9-ethyl-tetracyclo(6,2,1,1,
0) Mono-substituted -4-dodecene accounted for 92.5%, disubstituted -4-dodecene accounted for 6.0%, and others accounted for 1.5%. The measurement results of the infrared absorption spectrum are shown in FIG.

Comparative example 1 113 g of toluene was placed in the same flask as in Example 1.

10 g of n-heptane and 1.3 g of AlC1B powder are stirred in a nitrogen atmosphere. Add 100 g of 5-methylnorbornene from the dropping funnel over 30 minutes while maintaining the temperature at 60°C. The reaction continued at 60°C for 1.5 hours. Gas chromatography analysis at this point showed that 42% of 5-methylnorbornene and 14% of toluene had reacted.

The reaction solution was washed with water to remove unreacted sludge, resulting in 58 g of a liquid resin with a strong odor. Hue: 9° Liquid chromatography analysis revealed that 1-substituted 5-methylnorbornene in toluene 5
5%, 21% disubstituted derivatives, and 18% high molecular weight parts.

Examples 5 to 7, Comparative Example 2 SIS block copolymer (rTR-11 manufactured by Shell Chemical Co., Ltd.
074) 100 parts by weight, 30 parts by weight of softener (Shell Chemical Co., Ltd. [Shell Flex 22RJ), 3 parts by weight of stabilizer (Irganox 10IOJ, manufactured by Geigy), commercially available aliphatic petroleum resin (Mitsui Petrochemical Industries, Ltd. "Irganox 10IOJ"). Example 1.2.
30 parts by weight of the liquid resins obtained in Comparative Example 4 and Comparative Example 1 were each mixed and kneaded in a kneader at 150°C for 30 minutes to prepare an adhesive. This adhesive was melted and applied to a thickness of 30±5 μm using an applicator on a polyester film (25 μm thick) on a 195° C. heating plate for 20 minutes to prepare an adhesive tape. Next, adhesive performance was evaluated using the test method shown below.

+11 Corrugated cardboard adhesion: Press the adhesive tape onto corrugated paperboard (JIS K-7) at 5°C by rolling an 850 g rubber roller, immediately peel it off, and examine the surface condition of the corrugated paper.

Evaluation 5: The entire surface of the corrugated paperboard is destroyed.

4: 30% or more of the surface of the corrugated paperboard is destroyed.

3: Destruction of the surface of the corrugated paperboard is clearly observed.

2: Slight damage to the surface of the cardboard was observed.

Evaluation 1: No surface damage to the corrugated paperboard was observed.

(2) Tack (ball tack): Measured at 20°C by the J, Do method.

(3) Adhesive strength (g/25m width): JIS Z-1
It was measured at 20°C using the method of No. 524.

(4) Cohesive force (mm/2 HR): JIS Z
-1524 (7) Method: Measured at 20°C.

(5) Corrugated board retention strength (HR): Corrugated paper (JIS K-7) was used as an adherend, a load of 1 kg was suspended at the end, and the time until the load slipped off was measured at 20°C.

Comparative Example 3 The same procedure as in Example 5 was carried out except that commercially available liquid resin A ("Wingtack 10" manufactured by Gutdeyer Co., Ltd.) was used instead of the novel substituted aromatic hydrocarbon of the present invention.

Comparative Example 4 Instead of using the novel substituted aromatic hydrocarbons of the present invention, commercially available liquid resin B (rYS Resin PX-200 manufactured by Cheap Oil Co., Ltd.
The procedure was carried out in the same manner as in Example 5, except that J'') was used.

These results are shown in Table 1.

Example 8 SIS block copolymer (rTR-t1 manufactured by Shell Chemical Co., Ltd.
o7J) 100jTf parts, 30 parts by weight of softener (Shell Chemical Co., Ltd. "Shell Flex 22RJ"), stabilizer (
The same procedure as in Example 5 was conducted except that 100 M parts of the resin obtained in Example 3 was added to 3 parts by weight of "Irganox 1010" manufactured by Geigy.

Comparative Example 5 Instead of using the novel substituted aromatic hydrocarbons of the present invention, Mitsui Petrochemical Industries [Hiretsu T-300XJ]
The same procedure as in Example 8 was carried out except that .

Comparative Example 6 The same procedure as in Example 8 was carried out except that instead of using the novel substituted aromatic hydrocarbons of the present invention, commercially available product C ("Wing Tac Plus" manufactured by Gutdeyer) was used.

These results are shown in Table 2.

As a result, when the novel substituted aromatic hydrocarbons obtained according to the present invention are used as a tackifier for hot-melt pressure-sensitive adhesives, the resulting adhesive composition exhibits superior adhesive performance compared to comparative examples. It can be seen that the balance of adhesive performance (adhesiveness to punched balls, cardboard retention strength), which had been considered a problem up until now, has been greatly improved.

Examples 9 to 11 and Comparative Examples F to 9 Regarding the novel substituted aromatic hydrocarbons according to the present invention obtained in Examples 1.2 and 4, the boiling point, viscosity, and pour point were determined as Examples 9.10 and 11, respectively. , are shown in Table 3 as traction coefficients.

As comparative examples, Comparative Example 4 contained 2-methyl-2,4-dicyclohexylpenkune obtained by hydrogenating α-methylstyrene linear dimer, and Comparative Example 5 contained hydrogenated polybutene (
Idemitsu Petrochemical Polybutene 011'), Comparative Example 6
The properties of naphthenic mineral oil (Shell Chemical Co., Ltd., Shell Flex 371JY) were investigated.

The evaluation method is as follows.

Viscosity: Tokyo Keikisha E-type viscometer Pour point: JIS K-2269 Traction coefficient: Toyo Seiki Incometer (B45)
Traction coefficient (
t) was determined from the following formula.

Nat -Ft/Pn where Pt: traction, Pn: normal load (2500 g) As can be seen from the table, A of the present invention was useful as a power transmission medium, especially as a traction oil.

[Brief explanation of drawings]

FIG. 1, FIG. 3, and FIG. 5 each show infrared absorption spectra of the reaction products obtained in Example 1.2.4, with the horizontal axis representing the wave number. Moreover, FIG. 2 and FIG. 4 show Examples 1 and 3, respectively.
The gel permeation chromatogram of the reaction product obtained is shown with the horizontal axis representing the count number. Applicant Mitsui Petrochemical Industries Co., Ltd. Agent Kazudai Yamaguchi 1 Figure bJU2! Ic+ri2K(Naki1-.C1uL・UFuri(
. 2nd South 3rd Figure 56LiJ 2εlj [20CO+50C10005
CC No. 4 Figure 50 ” 60 65
70th figure 5? , :0 27CO20ULl
15LD 11100
S.C.O.

Claims (4)

[Claims] (1) At least one nuclear hydrogen atom of aromatic hydrocarbons is lower alkyl substituted or unsubstituted tetracyclo [6
,2,1,1,3,602,7] dodec-4-yl group or tetracyclo[6,2,1,1,3,602,7]
Novel substituted aromatic hydrocarbons substituted by dodec-5-yl groups. (2) Reacting aromatic hydrocarbons and lower alkyl substituted or unsubstituted tetracyclo[6,2,1,1,3,602,7]-4-dodecene in the presence of a Friedel-Crafts type catalyst. At least one nuclear hydrogen atom of the aromatic hydrocarbon is a lower alkyl-substituted or unsubstituted tetracyclo[6,2,1,1,3,602,7]dodeca-4-
yl group or tetracyclo[6,2,1,1,3,60
2,7] Process for producing novel substituted aromatic hydrocarbons substituted with dodec-5-yl group. (3) At least one nuclear hydrogen atom of the aromatic hydrocarbon is a lower alkyl-substituted or unsubstituted tetracyclo[
6,2,1,1,3,602,7] dodec-4-yl group or tetracyclo[6,2,1,1,3,602,7
] Adhesive additives comprising novel substituted aromatic hydrocarbons substituted with dodec-5-yl groups. (4) At least one nuclear hydrogen atom of the aromatic hydrocarbon is a lower alkyl-substituted or unsubstituted tetracyclo[
6,2,1,1,3,602,7] dodec-4-yl group or tetracyclo[6,2,1,1,3,602,7
] A power transmission medium comprising a novel substituted aromatic hydrocarbon substituted with a dodec-5-yl group.