Terpene copolymers

Details Terpene copolymers Terpene copolymers

1996-11-04

1998-05-26

Zitomer, Fred

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526271, 526272, 526280, 526281, 526284, 5263171, 5263183, 526319, 526336, 526338, C08F23208

Patent

active

057566240

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to terpene copolymers, to their production by radical polymerization and to their use.


PRIOR ART

Normally, terpenes are cationically homopolymerized and copolymerized. Typical catalysts for these polymerizations are aluminium trichloride, aluminium trichloride/antimony trichloride mixtures, ethyl aluminium dichloride/water mixtures, kaolinite or solid super acids.
Unfortunately, cationic polymerizations have the major disadvantage that they have to be carried out at low temperatures, generally with cooling. On an industrial scale, this procedure is extremely complicated and expensive.
Radical homopolymerizations and copolymerizations with terpenes have also been described, cf. Eur. Polym. J., 24 (5), 453-6, 1988.
These reactions are carried out solely as solution polymerizations, for example in tetrahydrofuran, benzene, dioxane or toluene. These partly toxic and carcinogenic solvents then have to be removed with considerable effort. Bulk polymerization is not described. It is even specifically pointed out (Eur. Polym. J., 24(5), 453-6, 1988) that solventless polymerization is undesirably accompanied by explosions and leads to insoluble and hence unusable polymers. Although there are references to bulk copolymerization, they relate to the monomers which readily lend themselves to radical homopolymerization.
The problem addressed by the present invention was to provide a process which would not have any of the above-mentioned disadvantages of cationic polymerization and radical solution polymerization and which would lead to useful products.


SUMMARY OF THE INVENTION

The solution provided by the invention consists in the provision of polymers containing monomer units of 5 carbon atoms or anhydrides thereof,


DETAILED DESCRIPTION OF THE INVENTION

The terpenes used include, for example, .alpha.-pinene, .beta.-pinene, terpinolene, limonene (dipentene), .beta.-terpinene, .gamma.-terpinene, .alpha.-thujene, sabinene, .delta.-.sup.3 -carene, camphene, .beta.-cadinene, .beta.-caryophyllene, cedrene, .alpha.-bisalbone, .beta.-bisalbone, .gamma.-bisalbone, zingiberene, humulene, (.alpha.-caryophyl-1ene), .alpha.-citronellol, linalool, geraniol, nerol, ipsenol, .alpha.-terpineol, D-terpineol-(4), dihydrocarveol, nerolidol, farnesol, .alpha.-eudesmol, .beta.-eudesmol, citral, D-citronellal, carvone, D-pulegone, piperitone, carvenone, bisabolene, .beta.-selinene, .alpha.-santalene, vitamin A, abietic acid and mixtures of these compounds.
Terpenes with internal double bonds are preferred, .alpha.-pinene, geraniol, nerol, citral and citronellal being particularly preferred. Of the terpenes containing an internal double bond, limonene/dipentene, .beta.-pinene, camphene and linalool are mentioned in particular.
The comonomer B) is selected from olefinically unsaturated mono-and/or dicarboxylic acids containing 3 to 5 carbon atoms or anhydrides thereof. Specific examples are maleic anhydride, maleic acid, fumaric acid, acrylic acid, methacrylic acid, itaconic acid and crotonic acid. Carboxylic acids containing a C--C double bond and derivatives thereof are preferably used, maleic acid and its derivatives being particularly preferred.
The comonomer C) is selected from vinyl monomers, for example styrene, vinyl chloride, vinylidene chloride, vinyl acetate, vinyl ether, acrolein and acrylonitrile.
Preferred comonomers C) are esters and/or semiesters of olefinically unsaturated monocarboxylic and/or dicarboxylic acids containing 3 to 5 carbon atoms, for example acrylates, methacrylates, maleic acid semiesters and diesters, fumaric acid semiesters and diesters, itaconic acid esters and crotonic acid esters. Mixtures of these compounds may also be used.
The alcohol radicals of the esters mentioned may be both short-chained (methyl, ethyl etc.) and long-chained (C.sub.12, C.sub.16, C.sub.18 fatty esters).
Esters of long-chain alcohols containing 6 to 22 carbon atoms are preferably used.
The quantities of monomer units A), B) and C) in the copolymer are as follows: total of A)+B)

REFERENCES:
patent: 4325770 (1982-04-01), Korpman
patent: 4421737 (1983-12-01), Ito
patent: 4670504 (1987-06-01), Cardenas
patent: 5514435 (1996-05-01), Suzuki

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