Carboxylic acid derivatives containing phosphorous groups and organically polymerisable groups
AssigneeFraunhofer-Gesellschaft zur Foerderung der angewandten Forschung e.V.
InventorsHerbert Wolter, Somchith Nique
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Abstract
The invention relates to carboxylic acid derivates which contain at least one organically polymerisable group and at least one group which contains phosphorous and is reactive or wich modulates the properties of the molecule. The invention also relates to a method for production of the inventive molecules and the use thereof in dentistry and for influencing the properties of materials.
Claims28
A compound of the formula (I)
- [(R1)(R2)P(O)—(CHR3)—(CHR4)—(CHR5)m—C(O)X—]n{B} I
- in which the substituents and indices have the following meanings:
- X is O, NH, NR6 or S,
- R1 and R2 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl or optionally substituted alkoxy, alkenyloxy, aryloxy, alkylaryloxy or arylalkyloxy,
- R3, R4, R5 and R6 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl, arylalkyl or hydroxy,
- {B} is a straight-chain or branched substituent with more than one organically polymerizable group and at least 2 carbon atoms, that contains no silicon atoms,
- m is an integer from 0 to 20,
- n is an integer from 1 to 20.
A compound of the formula (I)
- [(R1)(R2)P(O)—(CHR3)—(CHR4)—(CHR5)m—C(O)X—]n{B} I
- in which the substituents and indices have the following meanings:
- X is O, NH, NR6 or S,
- R1 and R2 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl or optionally substituted alkoxy, alkenyloxy, aryloxy, alkylaryloxy, arylalkyloxy, or hydroxyl.
- R3, R4, R5 and R6 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl,
- {B} is a straight-chain or branched substituent with more than one organically polymerizable group and at least 2 carbon atoms, that contains no silicon atoms,
- m is an integer from 0 to 20,
- n is an integer from 1 to 20,
- apart from:
- [4-oxo-4-(2-propenylamino)butyl]phenylphosphinic acid ethyl ester, [4-oxo-4-(2-propenylamino)butyl]phosphonic acid diethyl ester;
- compounds of the formula (ReO)2P(O)CH2CHRaCONHCH2NHCOCRb═CRcRd with R2=methyl or butyl, Ra=H or methyl, Rb═H. CH2CO2H or methyl, Rc=H and Rd═H, methyl, CONH2 or CO2H;
- CH2═C(RfC(O)O(CH2)xO(CO)CH(Rg)CH2—P(O)Ri(ORk) and
- CH2═C(RfCH2O(CO)CH(Rg)CH2—P(O)Ri(ORk) with Rf and Rg=hydrogen or methyl, Rk═C1-C18-alkyl,
- benzyl or phenyl, Ri=hydrogen or a C1-C4-alkyl and x=1 to 30, and also compounds in which {B} exhibits one or more isolated or oligomerized isoprene group(s).
A homopolymer of a compound of the formula (I)
- [(R1)(R2)P(O)—(CHR3)—(CHR4)—(CHR5)m—C(O)X—]n{B} I
- in which the substituents and indices have the following meanings:
- X is O, NH, NR6 or S,
- R1 and R2 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl or optionally substituted alkoxy, alkenyloxy, aryloxy, alkylaryloxy, arylalkyloxy, or hydroxy,
- R3, R4, R5 and R6 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl,
- {B} is a straight-chain or branched substituent with more than one organically polymerizable group and at least 2 carbon atoms, that contains no silicon atoms,
- m is an integer from 0 to 20,
- n is an integer from 1 to 20.
A copolymer of different compounds of the formula (I)
- [(R1)(R2)P(O)—(CHR3)—(CHR4)—(CHR5)m—C(O)X—]n{B} I
- in which the substituents and indices have the following meanings:
- X is O, NH, NR6 or S,
- R1 and R2 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl or optionally substituted alkoxy, alkenyloxy, aryloxy, alkylaryloxy, arylalkyloxy, or hydroxyl,
- R3, R4, R5 and R6 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl,
- {B} is a straight-chain or branched substituent with more than one organically polymerizable group and at least 2 carbon atoms, that contains no silicon atoms,
- m is an integer from 0 to 20,
- n is an integer from 1 to 20.
A copolymer formed by the use of monomer units of the formula (I) or of block polymer units constructed from monomers of the formula (I)
- [(R1)(R2)P(O)—(CHR3)—(CHR4)—(CHR5)m—C(O)X—]n{B} I
- in which the substituents and indices have the following meanings:
- X is O, NH, NR6 or S,
- R1 and R2 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl or arylalkyl or optionally substituted alkoxy, alkenyloxy, aryloxy, alkylaryloxy, arylalkyloxy, or hydroxy,
- R3, R4, R5 and R6 are, independently of one another, hydrogen or optionally substituted alkyl, alkenyl, aryl, alkylaryl-or arylalkyl,
- {B} is a straight-chain or branched substituent with more than one organically polymerizable group and at least 2 carbon atoms, that contains no silicon atoms,
- m is an integer from 0 to 20,
- n is an integer from 1 to 20.
Dependencies are inferred from the claim text.