JPH01502432A - polymer material - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] Polymer - material quality The heavy invention is a carbocyclic ring substituted at the 1,3,5-position or the 1,2,4.5-position. The IPls group is bonded to a six-membered ring system in the form of The present invention relates to polymeric substances having the following properties.

Many liquid crystalline main chain polymers are already known.

A, C1ferri is r Polymer Liquid Crystals ” [A, C1ferri, praise, R1 riegbaun and R, B, Heye Author: Academic Press (NY, NY), 1982, 6 [page 2] discloses many such systems. Nematete of such polymeric materials The ic phase is often at a temperature of 100° or more. Has a rod-like mesogenic group In materials that exhibit liquid-crystalline behavior, there is often no phase transition, and even more highly ordered materials exhibit liquid-crystalline behavior. Highly viscous smectic polymers are often used as nematic polymers. obtained by polymerization of monomers or cholesteric monomers. discotic Liquid crystal polymers require very complex synthesis routes and have high membrane phase transition temperatures. It stands out with a sharp point. No discogenic substances were discovered before 1984. Both have common structural principles.

That is, these substances have a rigid, flat central molecular part (usually an aromatic molecule, but , sometimes a metal complex), the “core” part of which is usually at least 3 , usually no more than 9 but up to 6 flexible-sided non-rigid alicyclic saturated nuclei Discotic compounds [8, Ohne and Praefck ^ngew, Chen, p. 96.70 (1984) with a three-dimensional nucleus. "pyramidal" mesogenic substances [1N by Zinnernan et al. aturforsch.

40a, p. 149 (191115)] and with a flexible crown ether nucleus. 'Tubular' mesogenic substances [J, H, Lehn et al., J, Chen, Soc; Chen, Co111un, 1985.1794] has recently become known. became.

Known discotic liquid crystal polymers include, for example, discogenic side groups. A pentasubstituted triphenylene ring is bonded via a flexible spacer. There are polysiloxane compounds [W, Kreuder and H, Rings-d Hakrolol, Chell, Rapid, C01111un, by orf 4.807 pages (1983)].

Polymers with discogenic groups in the main chain [W, Kr-euder, H, Hakro-nol by Ringsdorf and P. TSC Chirner; Chen, , Rapid Co1un, p. 6.376 (1985) and G. , cited reference by Wenz, p. 577 (1985)] is the core of the second government. functional benzene or triphenylene derivatives, each having four lateral Compounds having an alkoxy H or alkanoyloxy chain are included.

Polymers with mesogenic groups based on such conventional hexasubstituted central moieties The synthetic problems in formation are obvious. In other words, there are a total of 6 monomers One or two of the 01a groups have a high degree of substitution that is different from each other, but It must also be capable of polymerization or polycondensation.

It is therefore an object of the invention to overcome the above-mentioned disadvantages to a lesser extent, if any. discovery of polymeric materials with low degree of substitution and reduced yields. The goal is to discover corresponding low molecular weight compounds or monomers that have a tendency to crystallize. It was.

The birefringence and birefringence of the polymeric materials according to the invention can be varied within wide limits. was found to have positive and negative diamagnetic anisotropy. These polymers It can also be processed into any desired shape with properties that meet specific requirements. and has high chemical stability.

The polymeric materials according to the invention exhibit various physical properties that can be adapted to appropriate requirements. and provides a material with high mechanical stability.

The invention relates to carbocyclic rings substituted at the 1,3.5- or 1,2,4.5-positions. having a side group attached via a spacer to a six-membered or heterocyclic ring system Regarding polymeric substances, in particular, six-membered ring systems have the following formulas (1) to (3)%) (In each formula, H is a carbocyclic side chain group, and X is each independently H or C H and Y is 0 or NH) Polymer materials and formulas selected from %formula% [In the formula, Q is a group selected from formulas (1) to (3), and I is a polymerizable dicarboxylic is the core moiety of phosphoric acid], and also the above-mentioned In the formula, the carbocyclic rpJ chain group H is represented by the formula (5) (wherein R0 is H'', or Ro is alkyl, alkoxy, alkoxy each having 1 to 20 C atoms carbonyl, alkoxycarbonyloxy, alkoxybenzyloxy or lucanoyloxy, each R1 independently of the other is ■, or Alkyl, alkanoyloxy, alkoxy each having 1 to 20 C atoms carbonyl, alkoxycarbonyloxy, alkoxybenzyloxy or pertains to polymeric substances corresponding to

The present invention also relates to a method for producing a polymeric material according to claim 3, which method comprises: formula The corresponding dihydroxy compound of the formula HOOC-COOH The corresponding dicarboxylic acid compound or its reactive derivative represented by and the formula■ This method is characterized by polycondensation with a carbocyclic compound represented by In the formula, A is the formula (1a), (1b) and (1C) (1a> (Ib) (1c) (wherein each X, independently of the other, is N or CH) 'l　,2　bar0-CO-1-〇-CH2-5-CO-O- or -〇H2O - or Z = (1b), then -NH-CO- or can be -NH-CH2-, Q is OH, alkoxy, alkanoyl xy, COOH, alkanoyl, alkoxycarbonyl, p-alkoxybenzo yloxy, p-alkylbenzoyloxy or a group represented by the formula, p is 2, or P is A=, ■, alkoxy, alkanoyloxy, alkyl Koxycarbonyl, alkoxycarbonyloxy, alkoxybenzyloxy or or alkyl. The present invention also uses the above as an intermediate for the production of polymeric materials. of the corresponding dihydroxy compounds.

The invention furthermore provides for the use of polymeric materials according to the invention for the fiber and film industry. , for amplitude modulators and/or frequency modulators of laser light, and for optical signal recording. It relates to use as an organic substrate for electronic components for storage devices.

In the six-membered ring systems represented by formulas (1) to (3), the spacer is preferably a group -( IIJl) q-$42- or a single bond.

Ql is alkylene having 1 to 15al C atoms.

P and 2 are each independently preferably -o-, -5-1-o-c o-1-CO-O- or -CO-NH-, q is O or l.

The choice of the carbocyclic Sa group M is not limited per se, for example the group -spacer- M can be an alkyl, alkoxy or alkanoyloxy group; The group-spacer M is a "rod-shaped" group or a "disc-shaped" group known from liquid crystal chemistry. ” group [D, ris in Flissige by Deius et al. talle in Tabelle J, VEB Deut-scher V erlag far Grundstoffindustrie, Leipz ig city, fumyo 1-502432 (4) 1984], a suitable "rod-like" group has the formula ■R2-(A171)n-A2. z2- [[In the formula, 82 is H, alkyl, alkoxy, alkanoyloxy, alkoxyka] carbonyl, nitrile or halogen, and AI and A2 are each mutually unique. It is also a 1,4-cyclohexylene group, and one C present in this group 82 groups or two or more non-adjacent CH2 groups are represented by 0 and/or S alternatively, A1 and A2 are each unsubstituted, or has one or more halogen and/or nitrile as a substituent. is a 1,4-phenylene group in which one or more C The H group may be replaced by N, and zI and Z2 are each mutually exclusive. -CH2-CH2-1-CO-O-1-O-CO-1-(=(-1-0 CHz-1-CH20- or a single bond, and n is 1.2 or 3 ] However, the group H corresponding to formula (5) is particularly preferred.

Dicarboxylic oxidation of the formula tlOQC-tCOOH that can be polycondensed Examples of compounds include terephthalic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, Adipic acid, pimelic acid, speric acid, azelaic acid, sebacic acid, brassylic acid , tagsic acid, ferrogenic acid or its lower alcohol ester. . Preferred is preferably unsubstituted 02-CI5 alkylene, especially C2-C1 alkylene. and 1 to 5 CH, groups present in this alkylene, especially 1 to 3 C The Ht group also preferably has two O atoms or -0- and -C00- mutually. 1,4-cyclohexylene, 1,4-phenylene substituted with 1,4-benzoylene and/or 4-oxybenzoylene and the benzene ring di-substituted at the 1,4-position is optionally - position, another position, 5-position and/or 6-position one or more R jl (this group is an alkyl, alkoxy or alkyl group each having 20 C atoms) lucanoyloxy).

Therefore, - is preferably ethylene, propylene, butylene, vesethylene, hexylene, Silene, heptylene, octylene, nonylene, butylene, undecylene, dodecylene is ethylene, tributylene, tetrabutylene, or pentatylene, or Preferably 1,4-phenylene, 4,4'-[1,1'']-biphenyldiyl 4.4′-ρ-terphenyldiyl, ()o-(cut)-oO<n= 1 to 10), Formula I represents the racemic and optical pairs of these compounds and shall include mixtures thereof.

Preferred compounds represented by formula ■ have at least one of the groups contained in the molecule. Also, one is a compound having one of the abovementioned preferred meanings.

Particularly preferred compounds of formula I are compounds of subformulas Ia to Is below. is: The polycondensation is preferably carried out using an inert solvent and/or a catalyst compound, if necessary. and heating the reaction components at a temperature of about 50-350°, particularly about 150-300°. Moreover, the polycondensation can also be carried out by melt polycondensation or boundary polycondensation. You can also do more. Examples of suitable solvents are charcoal such as toluene or xylene. Hydrogen hydride, halogenohydrocarbons such as tetralobenzene or dichlorobenzene, The fluorine is an ether such as diphenyl ether.

Suitable catalysts are, for example, metal compounds and aluminum or titanium compounds. titanium (IV) compounds, such as titanium tetrabutal. -t is particularly suitable.

The copolymer composition having a liquid crystal phase according to the present invention has a polymerizable composition represented by 2H-Q-H. compound or its polymerizable derivative with no mesogenic group or with other mesogenic groups. Whether it has a gene group (e.g. a rod-shaped group) or a chiral group (e.g. West German Published Patent Application No. 2.831,909), or having a dye group (West German Published Patent Application No. 3,211,400) Copolymerizing monomers It can be obtained by

Copolymerization with monomers without mesogenic groups generally increases the glass transition temperature and transparency. By appropriate selection of the components, leading to a decrease in the temperature of the membrane, e.g. It is often possible to make the range between temperature layers particularly suitable for the intended application.

Monomers with a chiral group that can be used are, in principle, compounds with an asymmetric C atom. It is all of. However, the group R0,! or a group H or unit present in RI It is preferable to use a compound having one or more asymmetric C atoms in zero. Iral polymer materials also include suitable polymers with hydroxyl groups that are optically active. by reacting with aR''-Co-OH or one of their reactive derivatives. R represents a group having an asymmetric C atom.

Furthermore, the compounds according to the invention have the properties of typical polymers, such as layers, fibres, etc. It has many different variations because of its ability to form laminate, fibers, and ease of processing. shape is possible. These properties can be obtained by copolymerization or copolymerization with other components in a manner known per se. By mixing and changing the molecular weight, many different inorganic or by adding organic additives and metals, and by those skilled in the art of polymers. It can be changed by quite a few other processes with which we are familiar.

The carbocyclic compound of formula 1 according to the present invention forms a lyotropic phase and [West German Patent] No. 3,613,993 Suitable for manufacturing substances. In this case, the compound of formula I is dissolved or stirred. The mixture is mixed with a polymerizable compound by heating or irradiation, or by initiating Polymerize by adding.

The anisotropic polymer material thus obtained has optical anisotropy, magnetic anisotropy and ( or) in having favorable numerical values for electrical anisotropy and also favorable mechanical and It is distinguished by its thermal and thermal properties.

The polymer composition according to the invention has anisotropic physical properties that can be varied within a wide range. It can be used as a raw material for producing organic glasses.

Such applications can be found, for example, in the light and solar concentrator sector or in the organic photoconcentrator sector. Found in the case of chromic glass. j! An important application area is also optical signal storage. Found in the field of equipment.

Furthermore, the present invention can also be used in the field of magnetic signal storage devices. The composition can also be used as a material with nonlinear optical properties for producing nonlinear optical components. It is particularly suitable as a material matrix.

The following illustrates the invention: All temperature data are in degrees Celsius. Furthermore, the symbols have the following meanings: 202 solid crystalline state, H: mesogen phase, D: discotic phase, N 　: Nematic phase, ■ = Isotropic phase, (Additional symbols indicate the occurrence of an emerging phase of the same type. present) The number between the two symbols indicates the phase transition temperature due to heating (the number in parentheses indicates the phase transition temperature due to cooling). Example 1 showing transfer temperature 1.3.5-Trihydroxybenzene (phloroglucinol) 252■, 3,4 ．． 5-Tridecyloxybenzoyl chloride 4.87g, triethylamine A mixture of 4 g and 130 nj of anhydrous tetrahydrofuran was stirred for 48 hours. , boil to reflux. Separate the cooled solution from triethylamine hydrochloride and remove the solvent. is removed and the residue is recrystallized from acetone. 1,3.5-tris-(3°, 4°,5°-tris-(decyloxybenzoyloxy)-benzene is obtained , melting range 35-42°, D 29.5”I (monomodified mesophase is significantly stable over time).

Similarly, the following compound is prepared: 1.3.5-tris-(3°, 4°, 5°-tris-(tetradecyloxy)-benzoyloxy)-benzene 1.3.5-tris- (3°, 4°, 5°-tris-(dodecyloxy)-benzoyl xy)-benzene 1.3.5- ) lis-(3', 4°, 5°-tris-(undecyloxy)-benzoyloxy)-benzene 1.3.5-tris-(3°, 4° , S'-tri s-(nonyloxy)-benzoyloxy)-benzene 1.3: s-tris-(3°, 4°, 5°-tris-(octyloxy)-benzene zoyloxy)-benzene 1,3.5-tris-(3°, 4°, 5°-tris-(heptyl 1.3.5-)-lis-(3', 4°, 5°-tris-( hexy ((pentyloxy)-benzoyloxy)-benzene 1.3.5-tris-(3°, 4°, 5°-tris-(pentyloxy)-benzoyloxy)-benzene 1.3. 5-Tris-(3°, 4″, 5°-tris-(dodecanoyloxy)-benzo yloxy)-benzene 1.3. S-tris-(3',4°,5°-tris-(undecanoyloxy)-benzoyloxy)-benzene1.3.5-tris-(3',4°,5°-tris-(decanoyloxy)-benzoyloxy)-benzene Noyloxy)-benzoyloxy)-be 1.3.5-Tris-(3', 4°, 5°-Tris-(nonanoyloxy) c)-benzoyloxy)-benzene 1.3.5-tris-(3°, 4°, 5°-tris-(octanoyloxy)-benzoyloxy)-benzene 1.3. S-tris-(3',4°,5°-tris-(heptanoyloxy)-benzoyloxy)-benzene 1.3. S -Tris-(3°, 4°, 5°-Tris-(He) xanoyloxy)-benzoyloxy)-benzene 1.3.5-tris-(3',4',5°-tris-(pentanoyloxy)-benzoyloxy)-ben Zen 1.3. S-tris-(3°, 4°, 5°-tris-(butyryloxy)-benzoyloxy)-benzene code table 1,100-502,432 (6) Example 2 Cis, cis-1,3,5-trihydroxycyclohexane ( 264 r@t, 3,4.5-tridecyloxybenzoylchloride A mixture of 4.87 g of triethylamine, 4 g of triethylamine and 130+ g of anhydrous tetrahydrofuran is boiled and refluxed for 48 hours with stirring. After cooling the solution Then, separate the J triethylamine hydrochloride and remove the solvent. The residue is recrystallized from 300 IIj of ethanol and then four times from acetone. Cis, cis-1,3,5-tris-[3°,4°,5°-tris-decyloxybenzoyloxy]-cyclohexane is obtained, C31,3°D 61.5°I (Memphis +5 (can be cooled appropriately up to The following compound is prepared in the following manner: cis,cis-1.3.5-tris-[3°,4°,5°-tris-(tetradecyloxy)-benzoyloxy]-cyc Lohexane cis, cis-1,3,5-tris-[3°,4',5°-tris-(dodecyl- oxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3°, 4”, 5°-tris-(undecyloxy)-benzoyloxy]-cyclohesis, cis-1,3,5 -Tris-[3°,4°,5'-tris-(nonyloxy)-benzoyloxy]-cyclohe cis-1,3,5-tris-[3°, 4°, 5°-tris-(octyl) (heptyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3°, 4°, 5°-tris(heptyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3 , 5-Tris-[3°, 4°, 5°-Tris-(hexyl) oxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3',4°,5°-tris-(pentyloxy)-benzoyloxy]-cyclohexane oxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3°, 4°, 5’-tris-(dodecanoyl [(undecanoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3 ,S-tris-[3',4°,5°-tris-(decanoyloxy)-benzoyloxy]-cyclohexane cis,cis-1,3,5-)lis-[3°,4°,5°- Tris-(nonanoyl) oxy)-benzoyloxy]-cyclohexane cis, cis-1,3,S-tris-[3°, 4°, 5°-tris-(octanoy (benzoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3°, 4°, 5°-tris-(heptanoyloxy)-benzoyloxy]-cyclohexane (benzoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-tris-[3',4°,5'-tris-(hexanoyloxy)-benzoyloxy]-cyclohexane (benzoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-)-lis-[3°, 4°, 5°-tris-(pentano yloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-)lis-[3°14°,5°-tris-(butyryloxy) oxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-bis-[3°,5°-tris-(tetradecyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5- Bis-[3°, 5°-tris-(dodecyloxy)-benzoyloxy]-cyclohexanecis, cis-1,3,5-bis-[3', 5°-tris-(undecyloxy)cybenzoyl oxy]-cyclohexane cis, cis-1,3,5-bis-[3°,5°-tris-(nonyloxy)-ben cyclohexanesis, cis-1,3,5-bis-[3°, 5°-tris-(octyloxy)-benzoyloxy-cyclohexanesis, cis-1,3,5-bis-[3°, 5°-tris-(hegetyloxy)-benzo yloxycyclohexanesis, cis-1,3,5-bis-[3°, 5°- tris-(hexyloxy)-benzoyloxycocyclohexanesis, cis-1,3,5-bis-[3', 5°-Tris-(pentyloxy)-benzoyl oxycyclohexanecis, cis-1,3,5-bis-[3',5°-tri -(dodecanoyloxy)-benzoyloxy]-cyclohexane cis,cis-1,3,5-bis-[3°,5°-tris-(undecanoyloxy)-cyclohexane ci)-benzoyloxy]-cyclohexane cis, cis-1,3,5-bis-[3°,5°-tris-(decanoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5- Bis-[3°,5°-Tris-(nonanoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-bis-[3',So-tris-(octanoyloxy)-benzoyloxy]- Cyclohexane cis, cis-1,3,S-bis-[3',5°-tris-(heptanoyloxy)-benzoyloxy]-cyclohexane cis,cis-1,3,5-bis-[3°,5 °-Tris-(hexanoyloxy)-benzoyloxy]-cyclohexane cis, cis-1,3,5-bis-[3°,5°-tris-(pentanoyloxy)-benzoyloxy]-cyclohexane cis, cis -1,3,5-bis-[3',5'-tris-(butyryloxy)-benzoyloxy]-cyclohexane Example 3 a) 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1 ]-] Nonan-7-yl 3°, 4°, 5° Tris-pyridine 10 + 3.77 g of 3,4,5-tridecyloxybenzoyl chloride dissolved in pyridine 15 1j 3-phenyl-2, 4-Dioxa-3-borabicyclo[3,3,1]no 1.35 g of nan-7-ol [This compound was prepared by the method of P,N,5trOnlJ and J,F,N,Keana (J, OrO, Chen, p. 40.956, [1 975]) from cis, cis-1,3,5-cyclohexanetriol Add to the solution. The mixture is stirred at room temperature for 2 hours, then the solvent is removed under reduced pressure and the precipitate is washed with hot toluene. After recrystallizing twice, the above The following compound is prepared in a similar manner: 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]] Nan-7-yl 3°, 4°, 5° tris-(tetradecyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl 3°, 4°, 5° tris-(dodecyloxy)-benzoate 3-phenyl-2,4- Dioxa-3-borabicyclo[3,3,1]]nonane-7-yl 3°, 4°, 5° tris-(undecyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3, 3,1]]nonane-7-yl3°,4°,5°tris-(nonyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl3 °, 4°, 5° Tris-(octyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-yl 3°, 4°, 5° Tris- (heptyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl 3°, 4°, 5° tris-(hexyloxy)-benzoate 3-phenyl -2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl 3°, 4°, 5° tris-(pentyloxy)-benzoate 3-phenyl-2,4-dioxa-3- borabicyclo[3,3,1]]nonane-7-yl 3°, 4°, 5° tris-(dodecanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1] ]nonane-7-yl3°,4°,5-tris-(undecanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl3° , 4°, 5゛Tris-(decanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-yl 3°, 4', 5° Tris- (nonanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl 3°, 4°, 5° tris-(octanoyloxy)-benzoate 3-phenyl -2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl 3°, 4°, 5° tris-(heptanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3 -borabicyclo[3,3,1]]nonane-7-yl 3°,4',5°tris-(hexanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1 ]]nonane-7-yl 3°, 4°, 5゛tris-(pentanoyloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl 3° , 4°, 5° Tris-(butyryloxy)-benzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl p-tetradecyloxybenzoate -Phenyl-2,4-dioxa-3-borabicyclo[3,3,1'J nonan-7-yl p-dodecyloxybenzoate, C58°I 3-phenyl-2,4-dioxa-3-borabicyclo[3, 3,1]]nonane-7-yl p-undecyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-nonyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-octyloxybenzoate Top-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl phebutyloxybenzo3-phenyl-2,4-dioxa-3-borabi Cyclo[3,3,1]]nonan-7-yl p-hexyloxybenzoate 3-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonan-7-yl p-pentyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-dodecanoyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-undecanoyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-decanoyloxybenzoate Top-phenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-nonanoyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl P-octanoyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-heptanoyloxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo3-phenyl-2,4-di Oxa-3-borabicyclo[3,3,1]]nonan-7-yl p-pentanoyl oxybenzoate Tophenyl-2,4-dioxa-3-borabicyclo[3,3,1]]nonane-7-yl p-butyryloxybenzoate g) Preparation of cis,cis-1-(3,4,5-tris-(decyloxy)-benzoyloxy)-3,5-cyclohexanediol 1.26 g of the bicyclic compound prepared according to Example 3a a7tone 5 Add propane-1,3-diol I IIj to the solution in lj. The mixture was stirred at room temperature for 3 hours and then, after removing the volatile components under reduced pressure, the residue was taken up in ethyl acetate 5 if. and wash the mixture with water. Dry the organic phase, remove the solvent and triturate the residue. After recrystallization from toluene, the diol compound is obtained as a solid, C-5 ゜(-is, s°) H96,6° (94,5°)1゜Produce the following compound in the same manner: cis, cis-1-(3,4,S-tris-(tetradecyloxy)- benzoi cis, cis-1-(3,4,5-)lis-(dodecyloxy)-benzoyloxy cis)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(undecyloxy)-benzoyl) cis)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(nonyloxy)-benzoyloxy)-3,5-cyclohexanediolcis,cis-1-(3,4,S -Tris-(octyloxy)-benzoyloxy)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(heptyloxy)-benzoyloxy) cis)-3,5-cyclohexanediol cis,cis-1-(3,4,5-)lis-(hexyloxy)-benzoyloxy cis)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(pentyloxy)-benzoyloxy) cis)-3,5-cyclohexanediol cis,cis-1-(3,4,5-)lis-(butyloxy)-benzoyloxy)-3,5-cyclohexanediolcis,cis-1-(3,4, 5-) Lis = (dodecanoyloxy)-benzoyloxy)-3,5-cyclohexanediol cis, cis-1-(3,4,5-tris-(undecanoyloxy)-benzoy) cis, cis-1-(3,4,5-tris-(decanoyloxy)-benzoyloxy)-3,5-cyclohexanediol oxy)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(nonanoyloxy)-benzoyloxy) oxy)-3,5-cyclohexanediol cis, cis-1-<3.4.5-tris-(octanoyloxy)-benzoyl oxy)-3,5-cyclohexane cis, cis-1-(3,4, 5-Tris-(heptanoyloxy)-benzoyloxy)-3,5-cyclohexanediol cis, cis-1-(3,4,5-)lis-(hexanoyloxy)-benzoyloxy)-3,5- Cyclohexanediol 1 cis, cis-1-(3,4,5-)-lis-(pentanoyloxy)-ben zoyloxy)-3,5-cyclohexanediol cis,cis-1-(3,4,5-tris-(butyryloxy)-benzoyloxy) cis)-3,5-cyclohexanediol cis,cis-1-tetradecyloxybenzoyloxy-3,5-cyclohexane cis, cis-1-dodecyloxybenzoyloxy-3,5-cyclohexane diol All cis, cis-1-undecyloxybenzoyloxy-3,5-cyclohexane diol cis, cis-1-decyloxybenzoyloxy-3,5-cyclohexane diol C84,4″″ (75,5°) Ml 99.8@(92,3°) Mt 102° (100,5@) 3,5-cyclohexanediol cis, cis-1-octyloxybenzoyloxy -3,5-cyclohexanedi All cis, cis-1-hebutyloxybenzoyloxy-3,5-cyclohexanedi All cis, cis-1-hexyloxybenzoyloxy-3,5-cyclohexanedi All cis, cis-1-pentyloxybenzoyloxy-3,5-cyclohexanedi All cis, cis-1-butyloxybenzoyloxy-3,5-cyclohexanedio cis, cis-1-dodecanoyloxybenzoyloxy-3,5-cyclohexa cis, cis-1-undecanoyloxybenzoyloxy-3,5-cyclohexyl Sandiol cis, cis-1-decanoyloxybenzoyloxy-3,5-cy Old hexanediol cis, cis-1-nonanoyloxybenzoyloxy-3,5-cyclohexa cis, cis-1-octanoyloxybenzoyloxy-3,5-cyclohexa cis, cis-1-1-tanoyloxybenzoyloxy-3,5-cygochlorhexyl cis, cis-1-hexanoyloxybenzoyloxy-3,5-cyclohexanediol cis, cis-1-pentanoyloxybenzoyloxy-3,5-cyclohexa cis, cis-1-butyryloxybenzoyloxy-3,5-cyclohexane diol All C) cis, cis-1-(3°, 4°, 5°-tris-(decyloxy)-benzo Preparation of (undecanoyloxy)-3,S-bis-(undecanoyloxy)-cyclohexane 1 g of the diol compound from Preparation Example 3b was treated similarly to Example 3a to prepare undecanoylchlora. Esterify with 0.75 g of hydride.

This triazyloxy compound exhibits the following compatibility properties: Ct: 16.8@, C s: 20.8' IC+: 40.7°1 1-42. G°゛, H-32°, 1-10.6° Similarly to C1, prepare the following compound Produce: cis, cis-1-(3°14°, 5°-tris-(tetradecyl) oxy)-benzoyloxy)-3,5-bis-(undecanoyloxy)-cy chlorhexane cis, cis-1-(3°, 4°, 5°-tris-(dodecyloxy)-benzoy (undecanoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(undecyloxy)-benzo yloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(nonyloxy)-benzoyl oxy)-3,S-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(octyloxy)-benzoy (undecanoyloxy)-3,5-bis-(undecanoyloxy:・)-cyclohexane cis, cis-1-(3°, 4’, 5°-tris-(heptyloxy)-ben di yloxy)-3,S-bis-(tampkayloxyJ)-cyclohexane cis, cis-1-(3", 4', 5'-tris-(hexyloxy)-benzoy (undecanoyloxy)-3,5-bis-(undecanoyloxy))-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(pentyloxy)-benzoy (undecanoyloxy)-3,5-bis-(undecanoyloxy))-cyclohexane cis, cis~1-(3°, 4°, 5°-tris-(butyloxy)-benzoyl oxy)-3,S-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(dodecanoyloxy)-ben zoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis°, cis-1-(3°, 4°, 5°-tris-(undecanoyloxy)- benzoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexa cis, cis-1-<3', 4°, 5°-tris-(decanoyloxy)-be undecanoyloxy)-3,5-bis-(undecanoyloxy, 3/,)-cyclohe xansis, cis-1-('3°, 4°, 5°-tris-(nonanoyloxy) -benzoyloxy)-3,5-bis-(undecanoyloxy)-cyclohex sun cis, cis-1-(3°, 4°, 5°-tris-(octanoyloxy)-ben zoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(heptanoyloxy)-ben zoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(hexanoyloxy)-ben zoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(pentanoyloxy)-ben zoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(butyryloxy)-benzoy (undecanoyloxy)-3,5-bis-(undecanoyloxy)-cyclohexane cis, cis-1-(3', 4°, 5°-tris-(decyloxy)-benzoyl oxy)-3,5-bis-(p-decyloxy-benzoyloxy)-cyclohe Xane, Cl87.5@(83,2') C295,2° (93,9@') 14 + 116° H2118° N 140” (138°) I cis, cis -1-(3°, 4°, 5°-tris-(tetradecyloxy)-benzoyloxy c)-3,5-bis-(p-decyloxy-benzoyloxy)-cyclohexa cis, cis-1-(3°, 4°, 5°-tris-(dodecyloxy)-benzo yloxy)-3,5-bis-(p-decyloxy-benzoyloxy)-cyc Lohexanesis, cis-1-(3°, 4°, 5°-tris-(undecyloxy) )-benzoyloxy)-3,5-bis-(p-decyloxy-benzoyloxy) ci)-cyclohexanecis, cis-1-(3°, 4°, 5°-tris-(nonyl) oxy)-benzoyloxy)-3,S-bis-(p-decyloxy-benzoy cyclohexanecis, cis-1-(3', 4°, 5°-tris-( octyloxy)-benzoyloxy)-3,5-bis-(p-decyloxy- benzoyloxy)-cyclohexane cis, cis-1-(3°, 4°, 5°-t) Lis-(heptyloxy)-benzoyloxy)-3,5-bis-(ρ-decyl Oxybenzoyloxy)-cyclohexanecis, cis-1-(3°, 4°, 5°-Tris-(hexyloxy)-benzoyloxy)-3,5-bis-(p -decyloxy-benzoyloxy)-cyclohexanecis, cis-1-(3“ , 4°, 5°-tris-(pentyloxy)-benzoyloxy)-3,5-bi Su-(p-decyloxy-benzoyloxy)-cyclohexanecis, cis-1 -(3°, 4°, 5°-tris-(butyloxy)-benzoyloxy)-3, 5-bis-(p-decyloxy-benzoyloxy)-cyclohexanesis, -1-(3',4°,5°-tris-(dodecanoyloxy)-benzoyloxy) xy)-3,5-bis-(p-decyloxy-benzoyloxy)-cyclohexyl Sansis, cis-1-(3°, 4°, 5°-tris-(undecanoyloxy) -benzoyloxy)-3,5-bis-(p-decyloxy-benzoyloxy )-cyclohexanecis, cis-1-(3',4',5°-tris-(decanoyl) benzyloxy)-beidiyloxy)-3,5-bis-(p-decyloxy-benzo yloxy)-cyclohexanecis, cis-1-(3°, 4°, 5°-tris- (nonanoyloxy)-benzoyloxy)-3,5-bis-(p-decyloxy) cy-benzoyloxy)-cyclohexanecis, cis-1-(3°, 4°, 5° -Tris-(octanoyloxy)-benzoyloxy)-3,5-bis-(p -decyloxy-benzoyloxy)-cyclohexanecis, cis-1-(3° , 4', 5°-tris-(heptanoyloxy)-benzoyloxy)-3,5 -bis-(p-decyloxy-benzoyloxy)-cyclohexanesis, cis -1-(3°,4',5°-tris-(hexanoyloxy)-benzoyloxy c)-3,5-bis-(p-decyloxy-benzoyloxy)-cyclohexa cis, cis-1-(3°, 4°, 5°-tris-(pentanoyloxy)-beta) (benzoyloxy)-3,5-bis-(p-decyloxy-benzoyloxy)- cyclohexane cis, cis-1-(3°, 4°, 5°-tris-(butyryl oxane) c)-benzoyloxy)-3,5-bis-(p-decyloxy-benzoyloxy) xy)-cyclohexane example 4 a) 2.5-di[3°, 4°, 5°-tridecyloxybenzoyloxy]- Production of 1,4-benzoquinone 2.5-di-droxybenzoquinone 700■, 3, 4.5-tridecyloxybenzoyl chloride 8g, triethylamine 1.3 A mixture of 3 g and 50 ij of anhydrous tetrahydrofuran was stirred for 48 hours. , boil to reflux. Cool the dark brown reaction solution and add 1 liter of triethylamine hydrochloride. After separation, the red-brown oily residue is dissolved in hot pentane.

A greenish precipitate separates from this solution at freezer temperature. Repeat recrystallization two more times.

b) 2.5-di[3°,4',5°-tridecyloxybenzoyloxy]- Reduction of benzoquinone Dissolve 2 g of the quinone compound in tetrahydrofuran, and add this solution to saturated sodium dithionate. Shake with thorium aqueous solution for 10 minutes. Separate the solvent and purify the residue with hot acetone. Extract. The product is recrystallized twice from acetone. 2,5-di[3', 4°, 5°-Tris-(decyloxy)-benzoyloxy]-1,4-dihydroxy Benzene is obtained, H368' (69'') H2108° (99'> 1.

Similarly, the following compounds are prepared: 2.5-di[3°, 4°, 5°-tri Su-(tetradecyloxy)-benzoyloxy)-1,4-dihydroxyben Ze2.5-di[3°,4°,5’-)lis-(dodecyloxy)-benzoyl oxy)-1,4-dihydroxybenzene 2,5-di[3', 4°, 5'-) Lis-(undecyloxy)-benzoyloxy)-1,4-dihydroxyben Zen2.5-di[3',4°,5°-tris-(nonyloxy)-benzoyl oxy)-1,4-dihydroxybenzene 2,5-di[3', 4°, 5°-t Lis-(octyloxy)-benzoyloxy)-1,4-dihydroxybenze 2.5-di[3°, 4°, 5°-tris-(heptyloxy)-benzoyl oxy)-1,4-dihydroxybenzene 2,5-di[3°,4’,5°-t Lis-(hexyloxy)-benzoyloxy)-1,4-dihydroxyben Zen2.5-di[3',4°,5°-tris-(pentyloxy)-benzoy -1,4-dihydroxybenzene°2,5-di[3°, 4°, 5 °-Tris-(dodecasoyl-reoxy)-benzoyloxy)-1,4-dihyde Roxybenzene 2.5-di[3°, 4°, 5°-tris-(undecanoyloxy)-benzo yloxy)-1,4-dihydroxybenzene 2.5-di[3°,4’,5°-tris-(decanoyloxy)-benzoyl oxy)-1,4-dihydroxybenzene 2,5-di[3',4°,5°-t Lis-(nonanoyloxy)-benzoyloxy)-1,4-dihydroxyben Zen2.5-di[3°,4°,5'-tris-(octanoyloxy)-ben (zoyloxy)-1,4-dihydroxybenzene 2.5-di[3°,4°,5°-tris-(heptanoyloxy)-benzoy hydroxy)-1,4-dihydroxybenzene 2.5-di[3',4',5°-tris-(hexanoyloxy)-benzoy hydroxy)-1,4-dihydroxybenzene 2.5-di[3°,4°,5°-tris-(pentanoyloxy)-benzoy hydroxy)-1,4-dihydroxybenzene 2.5-di[3°,4’,5°-tris-(butyryloxy)-benzoyloxy xy)-1,4-dihydroxybenzene 2,5-di[3°,5°-bis-(te) Tradecyloxy)-benzoyloxy)-1,4-dihydroxybenzene2. 5-di[3',5°-bis-(dodecyloxy)-benzoyloxy)-1, 4-Dihydroxybenzene 2.5-di[3°,5°-bis-(undecyloxy) ci)-benzoyloxy)-1,4-dihydroxybenzene 2,5-di[3 °, 5”-bis-(nonyloxy)-benzoyloxy)-1,4-dihydroxy Cybenzene 2.5-di[3°,5°-bis-(octyloxy)-benzoyl oxy)-1,4-dihydroxybenzene 2,5-di[3°,5゛-bis-( hegetyloxy)-benzoyloxy)-1,4-dihydroxybenzene 2.5 -di[3°,5°-bis-(hexyloxy)-benzoyloxy)-1,4 -dihydroxybenzene2.5-di[3°,5゛-bis-(pentyloxy) -benzoyloxy)-1,4-dihydroxybenzene 2,5-di[3°, 5 °-Bis-(dodecanoyloxy)-benzoyloxy)-1,4-dihydroxy Cybenzene 2.5-di[3°,5°-bis-(undecanoyloxy)-ben zoyloxy)-1,4-dihydroxybenzene 2,5-di[3°,5°-bi Su-(decanoyloxy)-benzoyloxy)-1,4-dihydroxybenze 2, S-di[3°,5°-bis-(nonanoyloxy)-benzoyloxy )-1,4-dihydroxybenzene2,5-di[3°,5°-bis-(octa Noyloxy)-benzoyloxy)-1,4-dihydroxybenzene 2.5- Di[3°, 5°-bis-(heptanoyloxy)-benzoyloxy)-1, 4-dihydroxybenzene 2.5-di[3°,5°-bis-(hexanoyl) xy)-benzoyloxy)-1,4-dihydroxybenzene 2,5-di[3 °, 5゛-bis-(pentanoyloxy)-benzoyloxy)-1,4-dihydryl Droxybenzene 2.5-di[3°,5°-bis-(butyryloxy)-ben (zoyloxy)-1,4-dihydroxybenzene Example 5 1.2,4.5-tetrakis-(3°,4°,5°-tris-(decyloxybenzene) 2,5-di[3,',4° , 5°-tris-(decyloxy)-benzoyloxy]-1,4-dihydroxy Reacting cybenzene with 3.4.5-tridecyloxybenzoyl chloride It can be obtained by

Similarly, the following compounds are prepared: 1,2,4,5-tetrakis-(3', 4°,5°-tris-(tetradecyloxy)-benzoyloxy)-benzene 1.2,4.5-tetrakis-(3°,4°,5°-tris-(dodecyloxy )-benzoyloxy)-benzene 1.2,4.5-tetrakis=(3°, 4° , 5°-tris-(undecyloxy)-benzoyloxy)-benzene 1.2 , 4.5-tetrakis-(3°, 4°, 5°-tris-(nonyloxy)-ben zoyloxy)-benzene 1.2,4.5-tetrakis-(3°, 4°, 5°- Tris-(octyloxy)-benzoyloxy)-benzene 1.2,4.5- Tetrakis-(3°, 4°, 5°-tris-(heptyloxy)-benzoyl) xy)-benzene1.2,4.5-tetrakis-(3°,4’,5°-tris- (hexyloxy)-benzoyloxy)-benzene 1,2,4,5-tetraki su-(3°, 4°, 5°-tris-(pentyloxy)-benzoyloxy)- Benzene 1.2,4.5・-tetrakis-(3°, 4°, 5°-tris-(dode) Kanoyloxy)-benzoyloxy)-benzene 1,2,4,5-tetrakis -(3°,4',5°-tris-(undecanoyloxy)-benzoyloxy )-benzene 1,2,4.5-tetrakis-(3°, 4°, 5°-tris-(de Kanoyloxy)-benzoyloxy)-benzene 1,2,4,5-tetrakis -(3°, 4°, 5'-tris-(nonanoyloxy)-benzoyloxy)- Benzene 1.2,4.5-tetrakis-(3°, 4°, 5°-tris-(octa) Noyloxy)-benzoyloxy)-benzene 1,2,4,5-tetrakis- (3',4',5'-tris-(heptanoyloxy)-benzoyloxy)- Benzene 1.2,4.5-tetrakis-(3°,4',5°-tris-(hexa Noyloxy)-benzoyloxy)-benzene 1,2,4,5-tetrakis- (3°, 4°, 5°-tris-(pentanoyloxy)-benzoyloxy)- Benzene 1.2゜4,5-tetrakis-(3°, 4°, 5'-)lis-(butyryl) (benzoyloxy)-benzoyloxy)-benzene example 6 2.4.6-) Lis-(3°, 4’, 5°-tris-(decyloxy)-ben Production of zoyloxy)-triazineMelamine 42■ and 3,4.5-1lis- Heat 1.38 g of (decyloxy)-benzoic anhydride at 172°C with stirring. .

After heating for a further hour, the precipitate forms a melt and takes on a warm color. After cooling, The reaction mixture is taken up in ethyl acetate, the solid is separated from P, and the P solution is concentrated to dryness. . After recrystallization and purification by chromatography, tris-aroyloxy The triazine is obtained as a solid.

In a similar manner, the following compounds are prepared: 2.4.6-Dolisu (3°, 4°, 5 '-Tris-(tetradecyloxy)-benzoyloxy)-triazine 2.4 ．． 6-Dolisu (3°, 4°, 5’-tris-(dodecyl)-benzoyloxy )-triazine 2.4.6-Tris-(3°, 4°, 5°-tris-(undecyl)-benzo yloxy)-triazine 2.4.6-Dolisu (3°, 4°, 5°-tris-(nonyl)-benzoyl) xy)-triazine 2.4.6-Dolis(3°, 4°, 5′-tris-(octyl)-benzoyl oxy)-triazine 2.4.6-Dolisu(3°, 4°, 5°-tris-(heptyl)-benzoyl oxy)-triazine 2.4.6- Tris-(3°, 4°, 5°-tris-(hexyl)-benzoy triazine 2.4.6-) Lis-(3°, 4°, 5°-tris-(pentyl)-benzoy triazine 2.4.6-Tris-(3”, 4°, 5°-tris-(butyl)-benzoyl oxy)-triazine 2.4.6-Tris-(3°, 4°, 5°-tris-(dodecanoyl)-ben zoyloxy)-triazine2.4.6-)lis-(3°, 4°, 5°-triazine Su-(undecanoyl)-benzoyloxy)-triazine 2.4.6-Doris -(3°, 4°35°-tris-(decanoyl)-benzoyloxy)-tria gin 2.4.6-)-Lis-(3°, 4’, 5°-Tris-(nonanoyl)-ben zoyloxy)-triazine 2.4.6-Tris-(3°, 4’, 5°-tris-(octanoyl)-ben zoyloxy)-triazine 2.4.6-tris-(3°, 4°, 5’-) Su-(heptanoyl)-benzoyloxy)-triazine 2.4.8-tris- (3',4',S'-tris-(hexanoyl)-benzoyloxy)-tria 2.4.6-)-Lis-(3°, 4', 5°-Tris-(pentanoyl) -benzoyloxy)-triazine2.4.6-)-lis-(3', 4°, 5° -tris-(butyryl)-benzoyloxy)-triazine Example 7 2.5-di[3°,4',5'-)lis-(decyloxy)-benzoyloxy ]-1,4-dihydroxybenzene to 2,5-bis-decyloxy-terephtha royl chloride and as in Example 1 or by the method of H. Ba1lauf [ Hakronol, Chei, Rapicl, Connun, E, p. 407 ( 191116)], a polymeric material is obtained.

The product was dissolved in N-methylpyrrolidone for further purification if necessary. and then can be precipitated as a white amorphous solid by addition of ethanol. Wear.

A similar polycondensation can be performed using terephthaloyl chloride.

Example 8 cis, cis-1,3-dihydroxy-5-[3°, 4°, 5° from Example 3b Lis-(decyloxy)-benzoyloxy)-cyclohexane 0.5 mmol , sebacate dimethyl ester 115■ (0.5 mmol), titanium tetra Butalt 4.9■ (0,014 mmol) and O-dichlorobenzene 211 Heat the mixture of J at 160° for 2 hours. During this time, the solvent is slowly flushed with nitrogen. be removed through controlled distribution. The residue was then gradually heated to 250° under reduced pressure. heat. The resulting polymer was dissolved in 10 aJ of N-methylpyrrolidone, and then dissolved in methane. Tanol is added to precipitate a white fibrous product.

Example 9 1.Terephthaloyl dichloride in 1,2,2-tetrachloroethane 411j A 0.5 mmol solution was prepared using a method described in the literature [Beck, Beck, Ringsd, H. Hakronol, Chel, RaoidConnun, z, 3 by orf 89 (1986)] from Example 3b at 0° C. under an inert gas atmosphere. cis, cis-1-(3°, 4’, 5°-tris-(decyloxy)-benzoyl oxy)-3,5-cyclohexanediol 0.5 mmol, 1.1,2.2- Add to a mixture of 2IIj of tetrachloroethane and 0,3IIJ of pyridine. Mixed The mixture was stirred at room temperature for 4 days, then at 55°C for 1 day, then after cooling, the solution is added dropwise to methanol, a white fibrous product precipitates.

Diol compound from Example 3b and sebacic acid dichloride or 2,5-bis-( Dicarboxylic acid chlorides such as (decyloxy)-terephthaloyl dichloride A polycondensate with is obtained in the same manner.

international search report EP 8800105

Claims (18)

[Claims] 1.Carbocyclic or substituted at 1,3,5-position or 1,2,4,5-position or a carbocyclic side chain group bonded to a heterocyclic six-membered ring system via a spacer. Polymer material with. 2. The above six-membered ring system is the formula (1) to (3) spacer-M▲ mathematical formula, chemical formula, table, etc. There is ▼ (1) Spacer-M ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (2) Spacer - M ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (3) (In each formula, M is a carbocyclic a side chain group, each X, independently of one another, is N or CH; and Y is O or NH) Polymeric material according to claim 1, characterized in that it is selected from: 3. formula -Q-CO-W-CO- [In the formula, Q is a group selected from the above formulas (1) to (3), and W is a polymerizable di The polyester according to claim 2, which contains a unit represented by [which is a core portion of a carboxylic acid] Mar supplies. 4. Carbocyclic side chain group M is represented by formula (5) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(5) (In the formula, R0 is H or Alkyl, alkoxy, alkoxycarbony, each having 1 to 20 C atoms alkoxycarbonyloxy, alkoxybenzyloxy or alkanoyl and each R1, independently of one another, is H or or alkyl, alkanoyloxy, each having 1 to 20 C atoms; cy, alkoxycarbonyl, alkoxycarbonyloxy, alkoxybenzyl oxy or alkoxy). and 3. 5. 4. A method for producing a polymeric material according to claim 3, comprising the formula: H-Q-H The corresponding dihydroxy compound of the formula HOOC-W-COOH Polycondensation with the corresponding dicarboxylic acid compound or its reactive derivative represented by A manufacturing method characterized by: 6. Formula I ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, A is the formula (1a), (1b) and and (1c), ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1a)▲There are mathematical formulas, chemical formulas, tables, etc.▼ (1b) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1c) (In the formulas, X is mutually exclusive. independently N or CH), Z is -O-CO-, -O-CH2-, -CO-O- or -CH2O-, Alternatively, when A=(1b), Z is also -HH-CO- or -NH-C can be H2-, Q is OH, alkoxy, alkanoyloxy, COO H, alkanoyl, alkoxycarbonyl, p-alkoxybenzoyloxy, p-alkylbenzoyloxy or formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ The author is indicated by P is 2, or if A=(1c), p can also be 3 I can do it, R0 is alkoxy, alkanoyloxy, alkoxycarbonyl, alkoxyca rubonyloxy, alkoxybenzyloxy or alkyl, and R1 each independently represents H, alkoxy, alkanoyloxy, alkoxy Oxycarbonyl, alkoxycarbonyloxy, alkoxybenzyloxy or is alkyl] A carbocyclic compound represented by 7. A is a group represented by formula (1a), P is 2, and Q is OH 7. Compound according to claim 6, characterized in that: 8. 8. Compound according to claim 7, characterized in that Z is -O-CO-. 9. Claim characterized in that at least one of the groups R1 is a group other than H A compound according to item 6. 10. A is a group represented by formula (1b), and Q is a group represented by the formula ▲ Numerical formula, chemical formula, table, etc. There is▼ 7. The compound according to claim 6, which is a group represented by: 11. 11. Compound according to claim 10, characterized in that X is N. 12. A is a group represented by the formula (1C), and one of the groups Q is a group represented by the formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ and two of the groups Q are -OH, alkoxy, alkano be yloxy, -COOH, alkanoyl or alkoxycarbonyl 7. A compound according to claim 6, characterized in that 13. Two groups Q are -OH, alkoxy, alkanoyloxy, -COOH, a lucanoyl or alkoxycarbonyl, which are represented by formula (1c); 13. A compound according to claim 12, characterized in that it is present in the p-position of the group. 14. formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ In the two groups represented by, one of the groups R1 is H. , a compound according to claim 12. 15. Dihydroxy compound of formula I according to claim 6 (P=2/Q=OH ) as an intermediate for the production of polymeric substances. 16. Textile industry and films of polymeric materials according to claims 1, 2, 3 or 4. Use as an organic base material for industrial electronic components. 17. Amplitude modulation of laser light of a polymeric material according to claim 1, 2, 3 or 4. and/or use in frequency modulation. 18. In optical data storage of polymeric materials according to claims 1, 2, 3 or 4. use.