Compounds of the Formula (I) wherein x is an integer from 1-4; p is an integer from 1-3; q is an integer from 0-3; Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more Cl, CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or m
Compounds of the Formula (I) wherein x is an integer from 1-4; p is an integer from 1-3; q is an integer from 0-3; Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more Cl, CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or more OR6, COOR or halogen; R1 if x is 1, is OR7, O—X+, NR8R9, C1-C20alkyl optionally substituted by one or more COOR10, or is C2-C20alkyl interrupted by one ore more O, or is C2-C5alkenyl or phenyl-C1-C4alkyl; R1 if x is 2, is for example C1-C20alkylene; R1 if x is 3, is for example a tri-valent radical; R1 if x is 4, is for example a tetravalent radical; R2 and R3 are hydrogen or C1-C8alkyl, or R2 and R3 together are O, C1-C3alkylene or CH═CH; R4 is C1-C4alkyl; R5, R6, R7, R8, R9 and R10 are for example hydrogen or C1-C4alkyl; and X is a x-valent cationic counter ion; are in particular suitable as photoinitiators for the curing with UV-A light (320-450 nm).
대표청구항▼
1. Compounds of the formula I′ whereinx is an integer from 1-4;Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or more OR6, COOR6 or halogen;R1 when x is 1, is OR7, O−X+,
1. Compounds of the formula I′ whereinx is an integer from 1-4;Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or more OR6, COOR6 or halogen;R1 when x is 1, is OR7, O−X+, NR8R9, C1-C20alkyl optionally substituted by one or more COOR10, or is C2-C5alkenyl or phenyl-C1-C4alkyl;R1 when x is 2, is C1-C20alkylene, C2-C20alkylene which optionally is interrupted by one or more O, or is O-A-O, O-A-NR15, NR15-A-O, NR′15-A-NR15, NR15a-A1-NR15b or NR′15—(CH2)x′-A-(CH2)x′—NR15 or is O−X2+O−;x′ is an integer from 1-4;R1 when x is 3, is N(R30O)3—; C3-C20alkanetriyltrioxy which optionally is substituted by OH; C3-C20alkanetriyltriamino; a trivalent siloxane, or O3−X3+;R1 when x is 4, is C4-C20alkanetetrayltetraoxy optionally substituted by OH; C4-C20alkanetetrayltetraamino; a tetravalent siloxane; or O4−X4+;R5 is hydrogen, C1-C4alkyl, phenyl which optionally is substituted by one or more C1-C4alkyl, C1-C4alkoxy or halogen; or is (C2-C6alkyleneO)n—R6;n is an integer from 1-20;R6 is hydrogen, C1-C4alkyl, C2-C5alkenyl or C2-C6alkanoyl;R7 is hydrogen, C2-C5alkenyl, C2-C20alkyl which is substituted by one or more OH, NR11R12 or Si(R14)y(OR13)z; or is C2-C20alkyl which is interrupted by one or more O or NR15 and optionally is substituted by one or more OH, NR11R12 or Si(R14)y(OR13)z; or is C1-C20haloalkyl which optionally is substituted by one or more OH, NR11R12 or Si(R14)y(OR13)z; or is C2-C20haloalkyl which is interrupted by one or more O or NR15;R8 and R9 independently of one another are hydrogen, C1-C20alkyl; C1-C8alkyl substituted by CN, COOR11 or Si(R14)y(OR13)z; C2-C8alkyl substituted by one or more NR11R12 or OR11; or are C3-C8cycloalkyl, C3-C5alkenyl, phenyl-C1-C4alkyl or phenyl which optionally is substituted by C1-C4alkyl, OR11 or halogen;or R8 and R9 together are C3-C7alkylene which optionally is interrupted by one or more O or NR15 and which C3-C7alkylene or interrupted C3-C7alkylene optionally is substituted by one or more C1-C4alkyl or COOR11;z is an integer from 0-3;y is an integer from 0-3, wherein the sum of y+z is 3;R10 is hydrogen or C1-C4alkyl;R11 and R12 independently of one another are hydrogen or C1-C4alkyl which optionally is substituted by OH;R13 is hydrogen, C1-C4alkyl or Si(R14)(R′14)(R″14);R14, R′14 and R″14 independently of each other are hydrogen or C1-C4alkyl;R15 and R′15 independently of one another are hydrogen; C1-C20alkyl which optionally is substituted by OH, COOR11 or CN; or is C2-C20alkyl which optionally is interrupted by one or more O; or is C3-C5alkenyl, phenyl-C1-C4alkyl, C1-C5alkanoyl or benzoyl;R15a and R15b independently of one another form an aliphatic ring with a carbon atom of A1 or R15a and R15b together are C1-C3alkylene;R30 is C2-C8-alkylene optionally interrupted by one or more O;A is C2-C20alkylene which optionally is interrupted by one or more O or NR15; C2-C20haloalkylene which optionally is interrupted by one or more O or NR15; C5-C20cycloalkylene; or A is a divalent siloxaneA1 is C2-C20alkylene which optionally is interrupted by one or more O or NR15; andX is a x-valent cationic counter ion. 2. Compounds according to claim 1, whereinAr is phenyl or naphthyl each of which optionally is substituted by one or more CN, OR5,C3-C5alkenyl or by C1-C6alkyl which optionally is substituted by one or more OR6, COOR6 or halogen; andR1, R5, R6 and x are as defined in claim 1. 3. Compounds according to claim 1, wherein x is an integer from 1-4;Ar is phenyl or phenyl which is substituted by one or more OR5 or C1-C6alkyl which optionally is substituted by one or more OR6 or COOR6;R1 when x is 1, is OR7, O−X+, NR8R9 or C1-C20alkyl;R1 when x is 2, is O-A-O, NR′15-A-NR15, NR15a-A1-NR15b or NR′15—(CH2)x′-A-(CH2)x′—NR15;x′ is an integer from 1-4;R1 when x is 3, is N(R30O)3−;R1 when x is 4, is a tetravalent siloxane of the formula XII A2, A3, A4 and A5 are C1-C10alkylene which optionally is substituted by [O(CH2)g—O]h;g is 2;h is 1;a is 0b, c, d, e, s and t are 1;R5 is C1-C4alkyl;R6 is hydrogen;R7 is hydrogen, C2-C20alkyl which is substituted by OH; or is C2-C20alkyl which is interrupted by one or more O and optionally is substituted by OH; or is C1-C20haloalkyl which optionally is substituted by OH;R8 and R9 independently of one another are hydrogen, C1-C20alkyl; C1-C5alkyl substituted by Si(R14)y(OR13)z;or R8 and R9 together are C3-C7alkylene which optionally is substituted by COOR11;z is an integer from 0-3;y is an integer from 0-3, wherein the sum of y+z is 3;R11 and R13 are C1-C4alkyl;R14 is C1-C4alkyl;R15 and R′15 are hydrogen or C1-C20alkyl;R15a and R15b independently of one another form an aliphatic ring with a carbon atom of A1 or R15a and R15b together are C1-C3alkylene;R30 is C2-C5-alkylene;A is C2-C20alkylene which optionally is interrupted by one or more O; C2-C20haloalkylene; C5-C20cycloalkylene; or is a divalent siloxane of the formula X a is 0;j is 1;k is 2; andR16 R17 and R18 are C1-C18alkyl;A1 is C2-C20alkylene; andX is NR22R23R24R25;R22, R23, R24, R25 independently of one another are hydrogen; or C1-C20alkyl which optionally is substituted by OH, NR26R27, benzoyl or Si(OH)y(OC1-C4alkyl)z;or two of R22, R23, R24 or R25 together form a 6-membered saturated ring which optionally includes O as additional heteroatom; andR26 and R27 are hydrogen or C1-C4alkyl which optionally is substituted by OH. 4. Process for the preparation of compounds of the formula (I′) comprising a step of reacting a compound of the formula (F) with R1(H)x, whereinp is an integer from 1-3;q is an integer from 0-3;R2 and R3 independently of one another are hydrogen or C1-C5alkyl, or R2 and R3 together are O, C1-C3alkylene or CH═CH;R4 is C1-C4alkyl;Ar, R1 and x are as defined in claim 1. 5. Compounds of the formula (F) whereinp is an integer from 1-3;q is an integer from 0-3;Ar is phenyl, naphthyl, anthryl or phenanthryl each of which optionally is substituted by one or more C1, CN, OR5, C3-C5alkenyl or C1-C6alkyl which optionally is substituted by one or more OR6, COOR6 or halogen;R2 and R3 independently of one another are hydrogen or C1-C5alkyl, or R2 and R3 together are O, C1-C3alkylene or CH═CH;R4 is C1-C4alkyl;R5 is hydrogen, C1-C4alkyl, phenyl which optionally is substituted by one or more C1-C4alkyl, C1-C4alkoxy or halogen; or is (C2-C6alkyleneO)n—R6;n is an integer from 1-20; andR6 is hydrogen, C1-C4alkyl, C2-C5alkenyl or C2-C6alkanoyl. 6. A photopolymerizable composition comprising (a) at least one ethylenically unsaturated compound; and(b) at least one photoinitiator compound of the formula (I′) according to claim 1. 7. A photopolymerizable composition according to claim 6, comprising, in addition to components (a) and (b), further photoinitiators (c) and/or further additives (d). 8. A process for the photopolymerization of monomeric, oligomeric or polymeric compounds having at least one ethylenically unsaturated double bond, which comprises irradiating a composition according to claim 6 with light in the range from 150 to 600 nm. 9. A process according to claim 8 for the preparation of pigmented and nonpigmented surface coatings, printing inks, screen printing inks, offset printing inks, flexographic printing inks, ink jet printing inks, overprint varnishes, powder coatings, printing plates, adhesives, pressure-sensitive adhesives, dental materials, optical waveguides, optical switches, colour testing systems, composite materials, gel coats, glass-fibre cable coatings, screen printing stencils, resist materials, resist materials for printed circuit board production, primary imaging resist and solder resist, colour filters, resist materials for plasma display panel production, for the encapsulation of electrical and electronic components, for the preparation of magnetic recording materials, for the preparation of three-dimensional objects by means of stereolithography, of photographic reproductions, image recording material, for holographic recordings, for the preparation of decolouring materials, for the preparation of image recording materials using microcapsules. 10. A coate substrate which has been coated on at least one surface with a composition according to claim 6. 11. A process for the photographic production of relief images in which a coated substrate according to claim 10 is subjected to imagewise exposure and then the unexposed portions are removed with a solvent. 12. A composition according to claim 6, which is a dual curable coating composition, comprising (a) at least one ethylenically unsaturated compound;(b) at least one compound of the (I′), as defined in claim 1, as photoinitiator(f) a thermal crosslinkable compound. 13. A composition according to claim 6, which is a double (thermal and UV) curable coating composition, comprising (a) at least an ethylenically unsaturated compound;(b) at least one compound of the formula (I′), as defined in claim 1, as UV-photoinitiator effective to enable UV-curing of the ethylenically unsaturated compound; and(g) at least one thermal radical initiator effective to enable IR-curing or NIR-curing or to enable the convection heat curing of the ethylenically unsaturated compound.
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이 특허에 인용된 특허 (9)
Desobry Vincent,CHX, (Co)polymers by photopolymerization.
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