Polyglycidyl compounds

Details Polyglycidyl compounds Polyglycidyl compounds

1999-04-23

2001-01-02

Trinh, Ba K. (Department: 1625)

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

Synthetic resins

From phenol, phenol ether, or inorganic phenolate

C528S098000, C528S110000, C528S112000, C528S114000, C525S438000, C525S530000, C525S533000, C525S934000, C549S557000, C549S560000

Utility Patent

active

06169158

ABSTRACT:

Polyglycidyl compounds
The present invention relates to polyglycidyl compounds based on spirobisindanes, to a process for the preparation of these compounds as well as to their use for the production of moulded articles, coatings, matrix materials, casting compounds or adhesives.
At present, polyglycidyl compounds are frequently used as reactive component in curable compositions, for example as hardeners or crosslinkers in powder coating compositions based on polyesters and polyacrylates. Many polyglycidyl compounds containing more than two epoxy groups have as such the disadvantage of being liquid either at room temperature or at a little above room temperature. Typical representatives of these viscous resins are, for example, the triglycidyl ester of trimellitic acid and the diglycidyl ester of 1,2-cyclohexanedicarboxylic acid. In practice, the homogeneous incorporation of these liquid compounds into solid compositions requires substantially more elaborate processing than is the case when using glycidyl compounds which are already solid.
The main component of the solid polyglycidyl compounds are diglycidyl compounds based on bisphenol A. These in turn have disadvantages if they are used as sole crosslinker for curable compositions. They are not suitable for the production of coatings which are resistant to outdoor weathering.
An improved flow behaviour is still to be desired regarding the known systems for outdoor weathering-resistant powder coating compositions based on e.g. polyesters and glycidyl compounds such as Araldite® PT 810 (triglycidyl isocyanurate [TGIC]).
Furthermore, JP Kokai Hei 8-92231 describes a crystalline, purely bifunctional 6,6′-diglycidyloxy-3,3′,3,3′-tetramethyl-1,1′-spirobisindane having a melting point of 80-140° C. which, owing to its high melt flow and low hydrolisable chlorine content, was developed for the production of electronic materials. JP Kokai Hei 8-217852 and JP Kokai Hei 9-124769 describe purely bifunctional 6,6′-diglycidyloxy-3,3′,3,3′-tetraalkyl-1,1′-spirobisindanes which are used in cured mixtures with phenol- or naphthol-based resins, preferably for sealing semi-conductor modules.
FR 2322161 A1 describes a process for the preparation of epoxy resins by condensation of a polyhydroxy spirobisindane of the formula
wherein X and Y are each independently of one another H, CH
3
, OH or Cl, with epichlorohydrin in the presence of a alkali hydroxide, characterized by using said alkali hydroxide solved in a low-weight alcohol (f.e. methanol or ethanol). The examples, by said process epoxidized 3,3,3′,3′-tetramethyl-5,5.6′,6′-tetrahydroxy-1,1′-spirobisindane, had an epoxy value below the theory.
It is the object of this invention to provide novel multifunctional and weather-resistant epoxy compounds which are solid at room temperature and which can be used, for example, as hardeners in polyester powder coating systems where they may replace, inter alia, TGIC as hardener. In this application, compounds that are solid at room temperature will be understood as meaning compounds having a T
g
value (determined by DSC, heating rate=20° C./min) higher than 20° C.
The object of this invention is achieved by providing a novel polyglycidyl compound having on average more than two, preferably more than two and a half, particularly preferably more than three, glycidyl groups per molecule and a T
g
value (determined by DSC, heating rate=20° C./min) higher than 20° C., based on a polyfunctional 1,1′-spirobisindane of formula I or on a mixture of different polyfunctional 1,1′-spirobisindanes of the general formula I
wherein
Z is a direct single bond or —O—; more than two of R
1
, R
2
, R
3
and R
4
are —OH, —O—CO—R—CO—OH, —O—R—OH,
—O—CO—NH—R—NH—CO—O—R—OH or —[O—C
m
H
2m
]
n
—OH, with the proviso that R
1
, R
2
, R
3
and R
4
are not —OH when Z is a direct single bond, wherein
m is an integer from 2 to 4,
n is an integer from 1 to 20, and
R is C
1
-C
8
alkylene, C
5
-C
8
cycloalkylene, C
6
-C
14
arylene or
partially hydrated C
6
-C
14
arylene,
and the remaining R
1
, R
2
, R
3
and R
4
are a hydrogen atom or —O—C
1
-C
8
alkyl, —O—C
5
-C
8
cycloalkyl, —O—C
6
-C
14
aryl, partially hydrated —O—C
6
-C
14
aryl or (meth)acrylate; and
R
5
, R
6
, R
7
and R8 are each independently of one another
C
1
-C
8
alkyl, C
5
-C
8
cycloalkyl, C
6
-C
14
aryl, partially hydrated C
6
-C
14
aryl or a hydrogen atom.
R
5
, R
6
, R
7
and R
8
defined as C
1
-C
8
alkyl are straight-chain or branched radicals, for example methyl, ethyl, n-propyl, isobutyl, sec-butyl and tert-butyl as well as the different isomers of pentane, hexane, heptane and octane.
R
5
, R
6
, R
7
and R
8
defined as C
5
-C
8
cycloalkyl are, for example, radicals containing 5 to 8 ring-carbon atoms, e.g. of cyclopentane, cyclohexane, cycloheptane and cyclooctane as well as their substitution products, in particular their alkyl substitution products, such as the C
1
-C
4
alkyl substitution products.
R
5
, R
6
, R
7
and R
8
defined as C
6
-C
14
aryl can be, for example, phenyl, tolyl, pentalinyl, indenyl, napthyl, azulinyl and anthryl.
R
5
, R
6
, R
7
and R
8
defined as partially hydrated C
6
-C
14
aryl are understood as being aryls which are partially hydrated by addition of hydrogen to one or several double bonds of the aromatic aryl, for example compounds of formula:
R
1
, R
2
, R
3
and R
4
defined as —O—C
1
-C
8
alkyl, —O—C
5
-C
8
cycloalkyl, —O—C
6
-C
14
aryl or partially hydrated —O—C
6
-C
14
aryl have the same meaning as that given above for the corresponding radicals which are not bound to oxygen.
R defined as C
1
-C
8
alkylene is understood as being the straight-chain bifunctional groupings —(CH
2
)
n
—, wherein n=1 to 8, i.e. for example methylene, ethylene, n-propylene, as well as the branched bifunctional groupings of propene, butene, pentene, hexene, heptene and octene.
R defined as C
5
-C
8
cycloalkylene containing 5 to 8 ring-carbon atoms may be, for example, 1,2- and 1,3-cyclopentenyl, 1,2-, 1,3- and 1,4-hexenyl, 1,2-, 1,3-, and 1,4-heptenyl and 1,2-, 1,3-, 1,4- and 1,5-octenyl, 1,2-norbornyl as well as their substitution products, in particular their alkyl substitution products, such as the C
1
-C
4
alkyl substitution products.
R defined as C
6
-C
14
arylene may be, for example, phenylene, tolylene, pentalinylene, indenylene, napthylene, azulinylene and anthrylene.
R defined as partially hydrated C
6
-C
14
arylene is understood as meaning arylenes which are partially hydrated by addition of hydrogen to one or several double bonds of the aromatic arylene.
Within the present context, the term “polyglycidyl compounds” will be understood as meaning compounds containing unsubstituted glycidyl groups as well as compounds containing glycidyl groups which are substituted by alkyl groups, preferably methyl groups. The polyglycidyl compounds obtained after the glycidylisation of the polyfunctional 1,1′-spirobisindanes are always polyglycidyl ethers or polyglycidyl esters.
The basic bodies of formula I, in which —Z— is a direct bond, are known and are prepared by varying the starting compounds in analogy to the synthesis of 3,3,3′,3′-tetramethyl-5,5′,6,6′-tetrahydroxy-1,1′-spirobisindane (SBI), for example according to Wilson Baker, J.Chem.Soc 1678 (1934).
R
1
, R
2
, R
3
and R
4
are accordingly determined by the choice of the radicals of the phenolic basic body used (in the case of SBI using pyrocatechol, i.e. 1,2-dihydoxybenzene), or by reacting the hydoxyl groups of the basic body by known subsequent reactions (reaction with anhydrides, etherification etc.), whereas R
5
, R
6
, R
7
and R
8
are determined by varying the ketone used (using e.g. acetone, i.e. dimethyl ketone, for the preparation of SBI).
The basic bodies of formula 1, in which —Z— is an oxygen bridge —O—, are known and can be prepared, for example, according to U.S. patent U.S. Pat. No. 3,764,337. R
1
, R
2
, R
3
and R
4
, and also R
5
, R
6
, R
7
and R
8
,

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