FIELD: chemistry.
SUBSTANCE: present invention relates to a compound having structure (I), or (II), or (V)
where R1 is -H, -CH2OH or -CH(OH)CH2OH; R2 is -H, -OH or -CH2OH; R3 is -H, -OH or -CH2OH; R10 is hydrogen or a hydrocarbon fragment containing from 1 to 20 carbon atoms, wherein each hydrogen atom of said hydrocarbon fragment can optionally be substituted with C1-C4-alkyl group or a halogen atom; n is 0 or 1; p is 0 or 1; R is -ZF and wherein Z is a hydrocarbon moiety containing from 0 to 10 carbon atoms, optionally substituted with 1–4 C1-C4-alkyl groups or 1–4 halogen atoms, and F is -COOH, -CH(COOH)2, -COOR4, -CHO, -CH(CHO)2, -C2H3, -C2H, -N3, -NH2, -NHR7, -OH, -CH(CH2OH)2, where R4 is C1-C4-alkyl group; R7 is C1-C4-alkyl group, provided that in compound (V) F is not -OH or -C2H3. Described also is a method of producing said compounds or a composition containing at least two different compounds said above, involving the following steps: a) providing a carbohydrate or lignocellulose-containing composition; b) adding an aldehyde, optionally containing at least one functional group selected from the group consisting of carboxylic acid, carboxamide, ether, alkyne, alkene, aldehyde, chloride, hydroxyl, azide, carboxylic ester, aldehyde, vinyl and amine, to a carbohydrate or a lignocellulose-containing composition to obtain a mixture; c) heating the mixture under acidic conditions; and d) separating, particularly extracting, the compounds. Also described is a method of producing a polymer, where at least one said compound is reacted with a compound of formula R9-L-R9A, where L is selected from a group consisting of (CH2)O (VII), CO (VIII) and diphenylsulphone (IX)
R9 and R9A are independently selected from a group consisting of -OR11, OH, -NR8, -COOH, -COOR4 and a halogen atom; where R11 is selected from the group consisting of aryl and alkyl, or R11 from residue R9 and R11 of residue R9A together form a ring system; where the halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine; where R8 is H or C1-C4-alkyl group; where R4 is C1-C4-alkyl group, preferably -CH3; and o is integer from 2 to 10, in particular from 2 to 4. Described is the use of said polymers to produce sheets, fibres or moulded objects, particularly as a substitute for poly (ethylene terephthalate).
EFFECT: obtaining a monomer which can be subjected to polymerisation or copolymerisation to obtain a completely renewable polymer, preferably biodegradable, having good thermal and / or mechanical properties.
22 cl, 9 dwg
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Authors
Dates
2025-01-31—Published
2020-10-14—Filed