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US 8,012,672 B2Granted
Sulphonium salt photoinitiators
AssigneeBASF SE
InventorsPascal Hayoz, Jean-Luc Birbaum, Stephan Ilg
Life of this patent
Estimating the term…
Abstract
Compounds of the formula (I), wherein L1, L2, L3 and L4 independently of one another are hydrogen or an organic substituent; R is for example C1-C20alkyl, C5-C12cycloalkyl, C2-C20alkenyl, substituted C1-C20alkyl; X is O, S, NRa or NCORa; Ra is for example hydrogen or C1-C20alkyl; and Y is an inorganic or organic anion; are suitable as photolatent acid generators.
Claims18
A compound of the formula I
- wherein
- L1, L2, L3 and L4 independently of one another are hydrogen or an organic substituent;
- R is T1, T2, T3, A-T1 or A-T3;
- and, if both L1 and L2 as an organic substituent are phenyl or cyclohexyl, R additionally denotes hydrogen;
- X is O, S, NRa or NCORa;
- provided that
- (i) if X is O and L1 and L2 are hydrogen, then R denotes A-T3 or T3;
- and
- (ii) if X is O, L1 is hydrogen and L2 is other than hydrogen, then R denotes A-T1 or T2;
- (iii) if X is S and L1 and L2 are hydrogen, then R denotes A-T1 or T2;
- and
- (iv) if X is NRa, Ra is alkyl and L1 and L2 are hydrogen, then R denotes A-T1 or T3,
- T2 is C5-C12cycloalkyl, C2-C20alkenyl, C5-C12cycloalkenyl, C1-C20alkyl substituted by one or more D, C2-C20alkyl interrupted by one or more E, C2-C20alkyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkyl substituted by one or more D, C2-C12cycloalkyl interrupted by one or more E, C2-C12cycloalkyl substituted by one or more D and interrupted by one or more E, C2-C20alkenyl substituted by one or more D, C3-C20alkenyl interrupted by one or more E, C3-C20alkenyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkenyl substituted by one or more D, C3-C12cycloalkenyl interrupted by one or more E or C3-C12cycloalkenyl substituted by one or more D and interrupted by one or more E;
- T3 is C5-C12cycloalkenyl, C1-C20alkyl substituted by one or more D3, C3-C20alkyl interrupted by one or more O, S or OCO, C2-C20alkyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkyl substituted by one or more D, C3-C12cycloalkyl interrupted by one or more CO, COO, OCO or
- C2-C12cycloalkyl substituted by one or more D and interrupted by one or more E, C2-C20alkenyl substituted by one or more D3, C5-C12cycloalkenyl substituted by one or more D, C3-C12cycloalkenyl interrupted by one or more E or C3-C12cycloalkenyl substituted by one or more D and interrupted by one or more E;
- T1 has one of the meanings as given for T2 or is C1-C20alkyl;
- Ra is hydrogen or T1;
- A is CO, COO or CONR2;
- D is hydrogen, R2, OR2, SR2, NR2R3, halogen, NO2, CN, O-glycidyl, O-vinyl, O-allyl, COR2, NR2COR3, COOR2, OCOR2,
- CONR2R3, OCOOR2, OCONR2R3, NR2COOR3, SO3H,
- C6-C18aryl, O—C6-C18aryl,
- O—CR2═CR3R4, CR2═CR3R4, COCR2═CR3R4, OCOCR2═CR3R4, NR5COCR2═CR3R4 or SO3M;
- D3 is OH, SR2, halogen, NO2, CN, O-glycidyl, O-allyl,
- SO3H,
- or SO3M;
- E O, S, COO, OCO, CO, NR2, NCOR2, NR2CO, CONR2, OCOO, OCONR2, NR2COO, SO2, SO, phenylene, or is phenylene substituted by one or more R2, OR2, SR2, C4-C6cycloalkylene, CR2═CR3 or
- R2, R3, R4 and R5 independently of one another are hydrogen, C1-C12alkyl, C5-C12cycloalkyl or phenyl;
- M is an inorganic or organic cation;
- and
- Y is an inorganic or organic anion.
27 more elements
A process for the preparation of a compound of the formula I,
- wherein
- L1, L2, L3 and L4 independently of one another are hydrogen or an organic substituent;
- R is T1, T2, T3, A-T1 or A-T3;
- and, if both L1 and L2 as an organic substituent are phenyl or cyclohexyl, R additionally denotes hydrogen;
- X is O, S, NRa or NCORa;
- provided that
- (i) if X is O and L1 and L2 are hydrogen, then R denotes A-T3 or T3;
- and
- (ii) if X is O, L1 is hydrogen and L2 is other than hydrogen, then R denotes A-T1 or T2;
- (iii) if X is S and L1and L2 are hydrogen, then R denotes A-T1 or T2;
- and
- (iv) if X is NRa, Ra is alkyl and L1 and L2 are hydrogen, then R denotes A-T1 or T3;
- T2 is C5-C12cycloalkyl, C2-C20alkenyl, C5-C12cycloalkenyl, C1-C20alkyl substituted by one or more D, C2-C20alkyl interrupted by one or more E, C2-C20alkyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkyl substituted by one or more D, C2-C12cycloalkyl interrupted by one or more E, C2-C12cycloalkyl substituted by one or more D and interrupted by one or more E, C2-C20alkenyl substituted by one or more D, C3-C20alkenyl interrupted by one or more E, C3-C20alkenyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkenyl substituted by one or more D, C3-C12cycloalkenyl interrupted by one or more E or C3-C12cycloalkenyl substituted by one or more D and interrupted by one or more E;
- T3 is C5-C12cycloalkenyl, C1-C20alkyl substituted by one or more D3, C3-C20alkyl interrupted by one or more O, S or OCO, C2-C20alkyl substituted by one or more D and interrupted by one or more E, C5-C12cycloalkyl substituted by one or more D, C3-C12cycloalkyl interrupted by one or more CO, COO, OCO or
- C2-C12cycloalkyl substituted by one or more D and interrupted by one or more E, C2-C20alkenyl substituted by one or more D3, C5-C12cycloalkenyl substituted by one or more D, C3-C12cycloalkenyl interrupted by one or more E or C3-C12cycloalkenyl substituted by one or more D and interrupted by one or more E;
- T1 has one of the meanings as given for T2 or is C1-C20alkyl;
- Ra is hydrogen or T1;
- A is CO, COO or CONR2;
- D is hydrogen, R2, OR2, SR2, NR2R3, halogen, NO2, CN, O-glycidyl, O-vinyl, O-allyl, COR2, NR2COR3, COOR2, OCOR2,
- CONR2R3, OCOOR2, OCONR2R3, NR2COOR3, SO3H,
- C6-C18aryl, O—C6-C18aryl,
- O—CR2═CR3R4, CR2═CR3R4, COCR2═CR3R4, OCOCR2═CR3R4, NR5COCR2═CR3R4 or SO3M;
- D3 is OH, SR2, halogen, NO2, CN, O-glycidyl, O-allyl,
- or SO3H;
- Or SO3M;
- E O, S, COO, OCO, CO, NR2, NCOR2, NR2CO, CONR2, OCOO, OCONR2, NR2COO, SO2, SO, phenylene, or is phenylene substituted by one or more R2, OR2, SR2, C4-C6cycloalkylene, CR2═CR3 or
- R2, R3, R4 and R5 independently of one another are hydrogen, C1-C12alkyl, C5-C12cycloalkyl or phenyl;
- M is an inorganic or organic cation;
- and
- Y is an inorganic or organic anion,
- by reacting a compound of the formula II or IIa,
- with thionylchloride in the presence of a Friedel-Crafts catalyst, followed by a substitution reaction to substitute the hydrogen with R in the case of formula (IIa), and optionally followed by an exchange of the anion Y.
29 more elements
Dependencies are inferred from the claim text.