(Meth)acrylate esters of organosiloxane polyols, process for their preparation, and their use as radiation-curable materials
AssigneeTh. Goldschmidt AG
InventorsHardi Döhler, Thomas Ebbrecht, Stefan Stadmüller
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Abstract
The invention relates to organopolysiloxanes comprising (meth)acrylate groups, to a process for their preparation and to their use as radiation-curing coating materials.
Claims29
An organopolysiloxane that contains (meth)acrylate groups and does not contain more than 10% Si—O—C-linked byproducts which is obtained by an addition reaction that comprises first reacting an organopolysiloxane of the formula
- where
- R1=identical or different, aliphatic or aromatic hydrocarbon radicals
- R2=R1 or H, with the proviso that at least one radical R2 is H,
- a=from 0 to 500,
- b=from 0 to 5,
- with a polyhydroxy alkenyl ether of the formula
- H2C═CH—(CH2)c—O—CH2—R3—(CH2—OH)d (II)
- where
- R3=a linear, cyclic, aromatic or branched hydrocarbon radical, with or without ether bridges,
- c=from 0 to 10,
- d=from 2 to 10,
- in the presence of platinum or rhodium catalysts, wherein the metal has an oxidation state of I, II, or III, and second, reacting the product formed above with, from about 0.4- to about 1-molar amounts of (meth)acrylic acid and from 0- to about 0.6-molar amounts of a monocarboxylic acid, based on hydroxyl groups, where said monocarboxylic acid is free from double bonds which are capable of undergoing addition polymerization.
A process for preparing an organopolysiloxane that contains (meth)acrylate groups which comprises reacting an organopolysiloxane of the formula
- where
- R1=identical or different, aliphatic or aromatic hydrocarbon radicals
- R2=R1 or H, with the proviso that at least one radical R2 is H,
- a=from 0 to 500,
- b=from 0 to 5,
- with a polyhydroxy alkenyl ether of the formula
- H2C═CH—(CH2)c—O—CH2—R3—(CH2—OH)d (II)
- where
- R3=a linear, cyclic, aromatic or branched hydrocarbon radical, with or without ether bridges,
- c=from 0 to 10,
- d=from 2 to 10,
- in the presence of platinum or rhodium catalysts, wherein the metal has an oxidation state of I, II, or III, and second, reacting the product formed above with, from about 0.4- to about 1-molar amounts of (meth)acrylic acid and from 0- to about 0.6-molar amounts of a monocarboxylic acid, based on hydroxyl groups, where said monocarboxylic acid is free from double bonds which are capable of undergoing addition polymerization.
A polyhydroxyl organosiloxane of the formula
- where
- R1=identical or different, aliphatic or aromatic hydrocarbon radicals
- a=0 to 500,
- b=0 to 5,
- R4=R1 or the radical (CH2)2—(CH2)c—O—CH2—R3(CH2—OH)d
- where
- R3=a linear, cyclic, aromatic or branched hydrocarbon radical, with or without ether bridges,
- c=0 to 10,
- d=2 to 10.
An polyhydroxyl organosiloxane obtained by a process which comprises reacting an organopolysiloxane of the formula
- where
- R1=identical or different, aliphatic or aromatic hydrocarbon radicals
- R2=R1 or H, with the proviso that at least one radical R2 is H,
- a=from 0 to 500,
- b=from 0 to 5,
- with a polyhydroxy alkenyl ether of the formula
- H2C═CH—(CH2)c—CH2—R3—(CH2—OH)d (II)
- where
- R3=a linear, cyclic, aromatic or branched hydrocarbon radical, with or without ether bridges,
- c=from 0 to 10,
- d=from 2 to 10,
- in the presence of platinum or rhodium catalysts, wherein the metal has an oxidation state of I, II, or III.
Dependencies are inferred from the claim text.