Process for producing carbamoyloxy (meth) acrylates and new carbamoyloxy (meth) acrylates

Carbamoyloxy(meth)acrylates obtainable by a process which comprises the transesterification of an hydroxyalkyl carbamate of formula (I), (II), (III), (IV), (V), (VI) or (VII)

• wherein
• k≧2
• n=0 to 2
• m=0 to 2
• n+m≧1
• p=n or m, q=n or m, r=n or m, s=n or m, v=n or m, w=n or m
• (p+q)=(r+s)=(v+w)=(n+m)
• each R1, each R2, each R20 is, independently, chosen from the group of
• hydrogen,
• halogen,
• hydroxy,
• alkyl, optionally substituted by hydroxy;
• halogen;
• aryl and/or aryl substituted by hydroxy, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges,
• alkenyl, optionally substituted by hydroxy;
• halogen;
• aryl and/or aryl substituted by hydroxy, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges,
• aryl, optionally substituted by hydroxy;
• halogen;
• alkyl;
• alkyl substituted by hydroxy, halogen and/or aryl;
• and/or alkyl containing from 1 to 8 ether bridges,
• R3 is an alkyl, optionally substituted by hydroxy, tertiary amine and/or aryl, and optionally containing from 1 to 20 ether bridges and/or from 1 to 3 tertiary amine bridges,
• R4, R5, R6, R12, R13, R14, R15 and R16 are, independently, chosen from the group of
• hydrogen, and
• alkyl, optionally substituted by hydroxy, tertiary amine and/or aryl, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges,
• with the proviso that, respectively, R3 and R4, R5 and R6, R12 and/or R13 and/or R14, R15 and R16 may be linked together in order to form a ring,
• R7, R8, R9, R10, R17 and R18 are, independently, chosen from alkylene, alkenylene, arylene and aralkylene chains which may contain from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges,
• R11 is hydrogen or alkyl;
• R19, R21, R22, R23, R25, R26, R27 and R28, are, independently, chosen from alkylene, alkenylene, arylene and aralkylene chains which may contain from 1 to 20 ether bridges, from 1 to 4 tertiary amine bridges, from 1 to 4 —CO— bridges and/or from 1 to 4 —O—CO— bridges;
• A is
• wherein R24 is hydrogen or alkyl;
• with an (meth)acrylate of formula (VIII)
• CH2═CR29—COOR30 (VIII)
• wherein R29 is hydrogen or methyl, and R30 represents an alkyl group comprising from 1 to 8 carbon atoms;
• in an equivalent ratio of (meth)acrylate to hydroxyalkyl carbamate higher than 3.5 and in the presence of an organotitanate, an organozirconate or an organotin catalyst.

Carbamoyloxy(meth)acrylates of formula (XVII), (XVIII), (XIX), (XX), (XXI), (XXII), (XXIII), (XXIV), (XXV) and (XXVI)

• wherein
• k, n, m, p, q, r, S, V, w, A, R7, R8, R9, R10, R17, R18, R11, R19, R21, R22, R23, R24, R25, R26, R27, R28 and R29 are as defined in claim 1,
• t≧3
• R37 is an alkyl substituted by a tertiary amine, and optionally containing from 1 to 20 ether bridges and/or from 1 to 3 tertiary amine bridges;
• or an alkyl containing from 1 to 20 ether bridges and/or from 1 to 3 tertiary amine bridges, optionally substituted by —O—CO—CR29═CH2, tertiary amine and/or aryl;
• each R38, each R40 is, independently, such as defined for R31 with the proviso that at least one R38 and at least one R40 is chosen from the group of
• halogen,
• —O—CO—CR29═CH2,
• alkyl substituted by —O—CO—CR29═CH2;
• halogen;
• aryl and/or aryl substituted by —O—CO—CR29═CH2, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges,
• alkyl containing from 1 to 8 ether bridges,
• alkenyl, optionally substituted by —O—CO—CR29═CH2;
• halogen;
• aryl and/or aryl substituted by —O—CO—CR29═CH2, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges,
• aryl, optionally substituted by —O—CO—CR29═CH2;
• halogen;
• alkyl;
• alkyl substituted by —O—CO—CR29═CH2, halogen and/or aryl;
• and/or alkyl containing from 1 to 8 ether bridges,
• R39 is 2-methyl-1,5-pentamethylene;
• or R39 is chosen from alkylene containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges;
• alkenylene, arylene and aralkylene chains each of which may contain from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges, or R39 is chosen from alkylene when at least one of R35 and R36 is different from hydrogen,
• each R31, each R32, each R50 is, independently, chosen from the group of
• hydrogen,
• halogen
• —O—CO—CR29═CH2,
• alkyl, optionally substituted by —O—CO—CR29═CH2;
• halogen;
• aryl and/or aryl substituted by —O—CO—CR29═CH2, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges
• alkenyl, optionally substituted by —O—CO—CR29═CH2;
• halogen;
• aryl and/or aryl substituted by —O—CO—CR29═CH2, halogen or alkyl;
• and optionally containing from 1 to 8 ether bridges
• aryl, optionally substituted by —O—CO—CR29═CH2;
• halogen;
• alkyl;
• alkyl substituted by —O—CO—CR29═CH2, halogen and/or aryl;
• and/or alkyl containing from 1 to 8 ether bridges
• R33 is an alkyl, optionally substituted by —O—CO—CR29═CH2, tertiary amine and/or aryl, and optionally containing from 1 to 20 ether bridges and/or from 1 to 3 tertiary amine bridges,
• R34, R35, R36, R42, R43, R44, R45 and R46 are, independently, chosen from the group of
• hydrogen, and
• alkyl, optionally substituted by —O—CO—CR29═CH2, tertiary amine and/or aryl, and optionally containing from 1 to 8 ether bridges and/or from 1 to 3 tertiary amine bridges,
• with the proviso that, respectively, R33 and R34, R35 and R36, R42 and/or R43 and/or R44, R45 and R46 may be linked together in order to form a ring.