Succinic acid alkyl ester mixtures used as plasticizers
View Patent ↗The present invention relates to novel succinic acid alkyl ester mixtures and to the use there as plasticizers for plastic materials. The claimed mixtures are characterized by having good plasticizing effects which lead the products produced with the mixtures to have improved application properties.
1. A plasticizer for plastics, the plasticizer comprising a mixture of alkyl succinates, wherein, based in each case on 100 percent of the mixture, the mixture comprises:
10 to 50% by weight alkyl succinates of the formula
R 1 —OC(O)—CH 2 CH 2 —C(O)O—R 1 (I);
25 to 75% by weight alkyl succinates of the formula
R 1 —OC(O)—CH 2 CH 2 —C(O)O—R 2 (II); and
10 to 50% by weight alkyl succinates of the formula
R 2 —OC(O)—CH 2 —CH 2 C(O)O—R 2 (III),
in which each of R 1 and R 2 is, independently, a straight-chain or branched alkyl moiety, with the proviso that R 1 is not the same as R 2 .
2. The plasticizer as claimed in claim 1 , wherein R 1 is n-octyl and R 2 is n-decyl.
3. The plasticizer as claimed in claim 1 , each of R 1 and R 2 is, independently, a straight-chain or branched alkyl moiety-having 8 to 12 carbon atoms.
4. The plasticizer as claimed in claim 1 , wherein the alkyl succinates of the formulae (I), (II), and (III) are derived from biomass resources, and the mixture comprises 0.01 ppm to 1000 ppm content by mass of nitrogen atoms and 0.01 ppm to 50 ppm content by mass of sulfur atoms, based in each case on the mixture.
5. A process for the production of the plasticizer as claimed in claim 1 , the process comprising, in a single process step, or in two successive process steps:
contacting succinic acid with two different monohydric alcohols of the formulae
R 1 —OH (IV), and
R 2 —OH (V),
at a temperature of 50 to 250° C. to produce the mixture of alkyl succinates, wherein R 1 and R 2 , is independently, a straight chain or branched alkyl moiety, with the proviso that R 1 is not the same as R 2 , and removing resultant water of reaction from the mixture.
6. A method for plasticizing a plastic, the method comprising incorporating the plasticizer as claimed in claim 1 in a plastic.
7. A method for plasticizing and/or aiding processing of a polymer composition, the method comprising incorporating the mixture as claimed in claim 1 as a processing aid and/or a plasticizer in the polymer composition, wherein the polymer composition comprises at least one of adhesives, components of adhesives, adhesive sealants, components of adhesive sealants, sealing compositions, components of sealing compositions, coating compositions, paints, inks, coating materials, and plastisols.
8. A process for production of plasticized polyvinyl chloride using the plasticizer as claimed in claim 1 , the process comprising:
mixing polyvinyl chloride with the plasticizer as claimed in claim 1 , at a temperature of 10 to 50° C., and optionally with other auxiliaries and additives, where from 10 to 200 parts of the plasticizer are used for every 100 parts of plastic to produce a plastisol, and
molding and processing the resultant plastisol at temperatures of from 140 to 200° C. to produce a final product.
9. A plastisol comprising at least one plastic and the plasticizer as claimed in claim 1 .
10. The plasticizer as claimed in claim 1 , wherein, based in each case on 100 percent of the mixture, the mixture comprises:
15 to 35% by weight alkyl succinates of the formula (I);
35 to 65% by weight alkyl succinates of the formula (II); and
15 to 35% by weight alkyl succinates of the formula (III).
11. The plasticizer as claimed in claim 10 , wherein:
the plasticizer is a plasticizer for plasticizing polyvinyl chloride;
R 1 is n-octyl and R 2 is n-decyl; and
based in each case on 100 percent of the mixture, the mixture comprises:
20 to 30% by weight alkyl succinates of the formula (I);
40 to 60% by weight alkyl succinates of the formula (II); and
20 to 30% by weight alkyl succinates of the formula (III).