Alkenyl ether polyols
AssigneesHenkel AG & Co. KGaA, Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.
InventorsAndreas Taden, Katharina Landfester, Stefan Kirschbaum
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Abstract
The invention relates to a method for producing radiation-curable alkenyl ether polyols, to radiation-curable alkenyl ether polyols produced using the method according to the invention, and to the use thereof for the synthesis of radiation-interlinkable oligomers or polymers by means of polyaddition reactions or polycondensation reactions, in particular for the synthesis of radiation-curable polyesters, polyethers, polyurethanes and polyureas, particularly preferably UV-curable polyurethanes. The invention also relates to radiation-curable polyurethane polymers that are obtained by reacting at least one alkenyl ether polyol according to the invention with a polyisocyanate.
Claims18
A method for manufacturing an alkenyl ether polyol containing at least one alkenyl ether group and at least two hydroxyl groups (—OH), comprising:
- A) conversion of an alkenyl ether containing at least one alkenyl ether group and at least one functional group selected from —OH, —COOH, —SH, —NH2 and derivatives thereof,
- with (i) an epoxide or (ii) a cyclic carbonate or derivative thereof;
- or
- B) conversion of an alkenyl ether containing at least one alkenyl ether group and at least one functional group selected from (i) epoxide groups and (ii) cyclic carbonate groups or derivatives thereof, with an alcohol, thiol, a carboxylic acid, or an amine or derivative thereof.
An alkenyl ether polyol of formula (I) or (V)
- where
- R1 is selected from a divalent organic residue;
- an at least divalent linear or branched, substituted or unsubstituted, alkyl with 1 to 20 carbon atoms;
- or a linear or branched, substituted or unsubstituted, heteroalkyl with 1 to 20 carbon atoms and at least one oxygen or nitrogen atom,
- R2 is selected from an organic residue;
- an organic residue with at least one —OH group and/or 1 to 1000 carbon atoms;
- an optionally divalent or polyvalent, linear or branched, substituted or unsubstituted, alkyl with 1 to 20 carbon atoms;
- or a linear or branched, substituted or unsubstituted, heteroalkyl with 1 to 20 carbon atoms and at least one oxygen or nitrogen atom,
- R3 is selected from an organic residue;
- an organic residue with 1 to 1000 carbon atoms;
- an optionally divalent or polyvalent, linear or branched, substituted or unsubstituted, alkyl with 1 to 20 carbon atoms;
- a linear or branched, substituted or unsubstituted, heteroalkyl with 1 to 20 carbon atoms and at least one oxygen or nitrogen atom;
- a (poly)alkylene glycol of the formula —O—[CHRaCH2O]b—Rb, where b is 1 to 100, Ra is H or a C1-4 alkyl residue, and Rb is OH or
- in formula (I), X is O, S, C(═O)O, OC(═O)O, C(═O)OC(═O)O, NRx, NRxC(═O)O, NRxC(═O)NRx, or OC(═O)NRx,
- in formula (V), X is O, S, OC(═O), OC(═O)O, OC(═O)OC(═O), NRz, NRzC(═O)O, NRzC(═O)NRz, or OC(═O)NRz,
- each R and R′ is selected independently from among H, C1-20 alkyl, and C2-20 alkenyl;
- or one of R and R′ is H and the other is C1-4 alkyl;
- or both R and R′ are H,
- each A, B, and C is independently selected from among CR″R′″,
- R″ and R′″ are selected independently from among H, a functional group, an organic residue, and C1-20 alkyl;
- or R″ and R′″ together or with the carbon atom to which they are bonded are an organic residue;
- or two of R″ and R′″ that are bonded to neighboring carbon atoms form a bond together in order to form a double bond between the neighboring carbon atoms,
- is a single or double bond, and if it is a double bond, the C that is
- bonded to R2 bears only one substituent R″ or R′″,
- m is an integer from 1 to 10,
- n, p and o are each 0 or an integer from 1 to 10, where n+p+o=1 or 2,
- s and t are each 0 or an integer from 1 to 10, where s+t=1 or 2,
- Rx is H, an organic residue, or
- and if X is not NRx where
- R2 has at least one substituent that is
- selected from among —OH and
- Rz is H, an organic residue, or
- and if X is not NRz where
- than R3 has at least one substituent that is selected from among —OH and
Dependencies are inferred from the claim text.