METHOD OF PREPARING A MONOMERIC PHOTOINITIATOR

The present disclosure provides a method of preparing a compound of Formula (V) wherein n of radicals R 6' to R 9' are -R b OC(O)C(R 13 )=CH 2 , and further wherein R 13 is H or C 1 alkyl, n is an integer of from 1 to 3 and for each of said n radicals, R b is independently selected from a...

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Hauptverfasser: Taden, Andreas, Schneider, Anja, Arnold, Moritz
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creator Taden, Andreas
Schneider, Anja
Arnold, Moritz
description The present disclosure provides a method of preparing a compound of Formula (V) wherein n of radicals R 6' to R 9' are -R b OC(O)C(R 13 )=CH 2 , and further wherein R 13 is H or C 1 alkyl, n is an integer of from 1 to 3 and for each of said n radicals, R b is independently selected from a covalent bond, C 2 -C 12 alkylene, C 3 -C 18 cycloalkylene or C 6 -C 18 arylene. In a first method step i), a disulfide compound of Formula (I) is reacted in an acidic medium having a pH of ≤ 4 with a hydroxyl functional compound of Formula (II) to yield a compound of Formula (III), wherein: R 2 to R 5 are independently selected from H or C 1 -C 6 alkyl, R 6 to R 9 correspond to said substituents R 6' to R 9' and are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 12 alkoxyalkyl, SR 12 , COOR 12 and N(R 12 ) 2 ; R 10 and R 11 are H; and, each R 12 is independently selected from C 1 -C 6 alkyl or C 6 -C 18 aryl, subject to the proviso that n of radicals R 6 to R 9 are R b (OH) and for each of said n radicals, R b is independently selected as defined above. In a second step ii) said compound of Formula (III) is reacted in an inert aprotic solvent with a (meth)acrylating agent of Formula (IV) to yield said compound of Formula (V), wherein: in Formula (IV), X is halide or -OC(O)C(R 13 )=CH 2 ; and, the number of moles of (meth)acrylate groups provided by said compound of Formula (IV) is at least equimolar with the number of moles of hydroxyl groups provided by the compound of Formula (III).
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In a first method step i), a disulfide compound of Formula (I) is reacted in an acidic medium having a pH of ≤ 4 with a hydroxyl functional compound of Formula (II) to yield a compound of Formula (III), wherein: R 2 to R 5 are independently selected from H or C 1 -C 6 alkyl, R 6 to R 9 correspond to said substituents R 6' to R 9' and are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 12 alkoxyalkyl, SR 12 , COOR 12 and N(R 12 ) 2 ; R 10 and R 11 are H; and, each R 12 is independently selected from C 1 -C 6 alkyl or C 6 -C 18 aryl, subject to the proviso that n of radicals R 6 to R 9 are R b (OH) and for each of said n radicals, R b is independently selected as defined above. In a second step ii) said compound of Formula (III) is reacted in an inert aprotic solvent with a (meth)acrylating agent of Formula (IV) to yield said compound of Formula (V), wherein: in Formula (IV), X is halide or -OC(O)C(R 13 )=CH 2 ; and, the number of moles of (meth)acrylate groups provided by said compound of Formula (IV) is at least equimolar with the number of moles of hydroxyl groups provided by the compound of Formula (III).</description><language>eng ; fre ; ger</language><subject>CHEMISTRY ; COMPOSITIONS BASED THEREON ; COMPOSITIONS OF MACROMOLECULAR COMPOUNDS ; HETEROCYCLIC COMPOUNDS ; MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVINGCARBON-TO-CARBON UNSATURATED BONDS ; METALLURGY ; ORGANIC CHEMISTRY ; ORGANIC MACROMOLECULAR COMPOUNDS ; THEIR PREPARATION OR CHEMICAL WORKING-UP</subject><creationdate>2024</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20240619&amp;DB=EPODOC&amp;CC=EP&amp;NR=4385982A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25543,76293</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20240619&amp;DB=EPODOC&amp;CC=EP&amp;NR=4385982A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Taden, Andreas</creatorcontrib><creatorcontrib>Schneider, Anja</creatorcontrib><creatorcontrib>Arnold, Moritz</creatorcontrib><title>METHOD OF PREPARING A MONOMERIC PHOTOINITIATOR</title><description>The present disclosure provides a method of preparing a compound of Formula (V) wherein n of radicals R 6' to R 9' are -R b OC(O)C(R 13 )=CH 2 , and further wherein R 13 is H or C 1 alkyl, n is an integer of from 1 to 3 and for each of said n radicals, R b is independently selected from a covalent bond, C 2 -C 12 alkylene, C 3 -C 18 cycloalkylene or C 6 -C 18 arylene. In a first method step i), a disulfide compound of Formula (I) is reacted in an acidic medium having a pH of ≤ 4 with a hydroxyl functional compound of Formula (II) to yield a compound of Formula (III), wherein: R 2 to R 5 are independently selected from H or C 1 -C 6 alkyl, R 6 to R 9 correspond to said substituents R 6' to R 9' and are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 12 alkoxyalkyl, SR 12 , COOR 12 and N(R 12 ) 2 ; R 10 and R 11 are H; and, each R 12 is independently selected from C 1 -C 6 alkyl or C 6 -C 18 aryl, subject to the proviso that n of radicals R 6 to R 9 are R b (OH) and for each of said n radicals, R b is independently selected as defined above. 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In a first method step i), a disulfide compound of Formula (I) is reacted in an acidic medium having a pH of ≤ 4 with a hydroxyl functional compound of Formula (II) to yield a compound of Formula (III), wherein: R 2 to R 5 are independently selected from H or C 1 -C 6 alkyl, R 6 to R 9 correspond to said substituents R 6' to R 9' and are independently selected from H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 12 alkoxyalkyl, SR 12 , COOR 12 and N(R 12 ) 2 ; R 10 and R 11 are H; and, each R 12 is independently selected from C 1 -C 6 alkyl or C 6 -C 18 aryl, subject to the proviso that n of radicals R 6 to R 9 are R b (OH) and for each of said n radicals, R b is independently selected as defined above. In a second step ii) said compound of Formula (III) is reacted in an inert aprotic solvent with a (meth)acrylating agent of Formula (IV) to yield said compound of Formula (V), wherein: in Formula (IV), X is halide or -OC(O)C(R 13 )=CH 2 ; and, the number of moles of (meth)acrylate groups provided by said compound of Formula (IV) is at least equimolar with the number of moles of hydroxyl groups provided by the compound of Formula (III).</abstract><oa>free_for_read</oa></addata></record>
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subjects CHEMISTRY
COMPOSITIONS BASED THEREON
COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
HETEROCYCLIC COMPOUNDS
MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVINGCARBON-TO-CARBON UNSATURATED BONDS
METALLURGY
ORGANIC CHEMISTRY
ORGANIC MACROMOLECULAR COMPOUNDS
THEIR PREPARATION OR CHEMICAL WORKING-UP
title METHOD OF PREPARING A MONOMERIC PHOTOINITIATOR
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