Recording material comprising chromogenic 3,1-benzoxazines

A pressure-sensitive, heat-sensitive and electro-sensitive recording material comprising a layer support and a color developer and a chromogenic 3,1-benzoxazine of the formula ##STR146## wherein one of the radicals X.sup.6 or R.sup.3 denotes NY.sup.4 Y.sup.5, OY.sup.6 or SY.sup.6 and the other denotes hydrogen, C.sub.1 -C.sub.18 -alkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.18 -alkoxy, cyano and/or C.sub.1 -C.sub.18 -alkoxycarbonyl, cyclohexyl, or benzyl, phenyl, biphenylyl or naphthyl radicals which are unsubstituted or substituted by chlorine C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.8 -alkoxy, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl and/or C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.8 -alkanoylamino or benzoylamino, which is unsubstituted or substituted by chlorine, C.sub.1 -C.sub.4 -alkyl and/or C.sub.1 -C.sub.4 -alkoxy,

• Z.sup.2 denotes hydrogen, C.sub.1 -C.sub.8 -alkyl, cyclohexyl or ##STR147## R.sup.2 denotes hydrogen, C.sub.1 -C.sub.18 -alkyl which optionally carries fluorine, chlorine, bromine, C.sub.1 -C.sub.8 -alkoxy, cyano or C.sub.1 -C.sub.18 -alkoxycarbonyl, cyclohexyl, or benzyl, phenyl, biphenylyl, terphenylyl, naphthyl, picolyl, pyridyl, quinolyl, pyrimidyl, pyrazinyl, triazinyl, triazolyl, triazolylmethyl, thiadiazolyl, tetrazolyl, indolyl or optionally benzofused imidazole, oxazole or thiazole radicals which optionally carry fluorine, chlorine, bromine, nitro, C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.18 -alkoxy, C.sub.1 -C.sub.18 -alkylthio, C.sub.1 -C.sub.18 -mono- or dialkylamino, C.sub.1 -C.sub.18 -alkylsulphonyl, cyano, C.sub.1 -C.sub.18 -alkoxycarbonyl and/or C.sub.1 -C.sub.18 -alkanoylamino,
• X.sup.4 and X.sup.5 independently of one another denote hydrogen, fluorine, chlorine, bromine or C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by fluorine, chlorine, nitro, hydroxyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, cyano, C.sub.1 -C.sub.8 -alkoxycarbonyl, C.sub.1 -C.sub.8 -alkanoyloxy, amino and/or mono- or di-C.sub.1 -C.sub.4 -alkylamino, phenyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkanoylamino, benzoylamino which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.12 -alkyl, indolyl or piperidyl radicals which are unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine and/or phenyl, NY.sup.4 Y.sup.5, OY.sup.6 or SY.sup.6,
• but wherein
• at most two of the radicals X.sup.4, X.sup.5 and X.sup.6 are NY.sup.4 Y.sup.5,
• Y.sup.4, Y.sup.5 and Y.sup.6 independently of one another denote hydrogen, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by chlorine, hydroxyl, di-C.sub.1 -C.sub.4 -alkyl-amino, cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, C.sub.1 -C.sub.4 -alkanoyloxy or C.sub.1 -C.sub.4 -alkoxy, cyclohexyl or phenyl or benzyl, which is unsubstituted or substituted by chlorine, C.sub.1 -C.sub.12 -alkyl or C.sub.1 -C.sub.12 -alkoxy, piperidyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, or members which, together with the N or O to which they are bonded and one of the rings A, B or C, are necessary to complete a ring system of the following formula ##STR148## wherein the broken line denotes further fusing-on in the case of ring C,
• Y represents hydrogen, C.sub.1 - to C.sub.18 -alkyl, which is unsubstituted or substituted by chlorine, cyano, C.sub.1 - to C.sub.4 -alkoxycarbonyl or C.sub.1 -to C.sub.4 -alkoxy, cyclohexyl, or phenyl or benzyl, which is unsubstituted or substituted by chlorine, C.sub.1 - to C.sub.12 -alkyl or C.sub.1 - to C.sub.12 -alkoxy, the saturated ring part can carry up to 4 radicals from the group comprising chlorine, C.sub.1 - to C.sub.4 -alkyl, C.sub.1 - to C.sub.4 -alkoxy and phenyl,
• the rings A, B and C are unsubstituted or substituted by chlorine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy or phenyl-amino which is unsubstituted or substituted by chlorine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and/or C.sub.1 -C.sub.4 -alkanoylamino or benzo-fused, or NY.sup.4 Y.sup.5 denotes a pyrrolo, pyrrolidino, piperidino, pipecolino, pyrazino, morpholino, pyrazolo or pyrazolino radical which is unsubstituted or substituted by chlorine, C.sub.1 -C.sub.4 -alkyl or aryl.

A pressure-sensitive, heat-sensitive and electro-sensitive recording material comprising a layer support and a color developer and a chromogenic 3,1-benzoxazine of the formula ##STR149## wherein X.sup.8 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkoxy, phenyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoylamino, benzoylamino which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, indolyl or piperidyl radicals which are unsubstituted or substituted by methyl, ethyl, methoxy, chlorine and/or phenyl, OY.sup.9 or SY.sup.9,

• X.sup.7 denotes NY.sup.7 Y.sup.7' or independently has the meaning of X.sup.8,
• R.sup.4 denotes hydrogen, C.sub.1 -C.sub.18 -alkyl which optionally carries fluorine, chlorine or C.sub.1 -C.sub.4 -alkoxy, cyclohexyl, benzyl which optionally caries chlorine and/or C.sub.1 -C.sub.18 -alkyl, or phenyl, biphenylyl, naphthyl, picolyl, pyridyl, quinolyl, pyrimidyl, pyrazinyl, triazolyl, thiadiazolyl, indolyl or optionally benzo-fused imidazole, oxazole or thiazole radicals which optionally carry chlorine, bromine, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -dialkylamino, C.sub.1 -C.sub.8 -alkylsulphonyl, cyano, C.sub.1 -C.sub.8 -alkoxycarbonyl and/or C.sub.1 -C.sub.8 -alkanoylamino,
• R.sup.5 and R.sup.7 independently of one another denote hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, amino, C.sub.1 -C.sub.4 -mono- or dialkylamino, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino, or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine,
• R.sup.6 and R.sup.8 independently of one another denote hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, amino, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy or chlorine,
• Y.sup.7 to Y.sup.9 independently of one another denote C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted by chlorine, cyano, methoxycarbonyl, methoxycarbonyloxy, acetyloxy, hydroxyl, methoxy, ethoxy or dimethylamino, cyclohexyl, benzyl, phenyl, which is unsubstituted or substituted by chlorine, cyano, methyl, ethyl, methoxy or ethoxy, or 2,2,6,6-tetramethyl- or 1,2,2,6,6-pentamethyl-piperidin-4-yl,
• Y.sup.7' and Y.sup.8' denote hydrogen or have the meaning of Y.sup.7 or Y.sup.8 respectively, or
• NY.sup.7 Y.sup.7' and NY.sup.8 Y.sup.8' independently of one another represent a pyrrolidino, piperidino, piperazino, morpholino or pyrazolino radical which is substituted by C.sub.1 -C.sub.4 -alkyl and/or phenyl, which can also carry chlorine, methyl, methoxy, ethoxy or cyano.

A pressure-sensitive, heat-sensitive and electro-sensitive recording material comprising a layer support and a color developer and a chromogenic 3,1-benzoxazine of the formula ##STR150## wherein X.sup.9 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkoxy, phenyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoylamino, benzoylamino which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, indolyl or piperidyl radicals which are unsubstituted or substituted by methyl, ethyl, methoxy, chlorine and/or phenyl, NY.sup.10 Y.sup.10', OY.sup.9 or SY.sup.9,

• X.sup.10 denotes OY.sup.11 or SY.sup.11 and
• R.sup.9 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkanoylamino, benzoylamino or C.sub.1 -C.sub.4 -alkylsulphonylamino, or
• X.sup.10 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.18 -alkyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkoxy, phenyl which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoylamino, benzoylamino which is unsubstituted or substituted by chlorine and/or C.sub.1 -C.sub.4 -alkyl, or indolyl or piperidyl radicals which are unsubstituted or substituted by methyl, ethyl, methoxy, chlorine and/or phenyl and
• R.sup.9 denotes C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, amino or C.sub.1 -C.sub.4 -mono or dialkylamino, or anilino or N-C.sub.1 -C.sub.4 -alkylanilino which is unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine, R.sup.4 denotes hydrogen, C.sub.1 -C.sub.18 -alkyl which optionally carries fluorine, chlorine or C.sub.1 -C.sub.4 -alkoxy, cyclohexyl, benzyl which optionally carries chlorine and/or C.sub.1 -C.sub.18 -alkyl, or phenyl, biphenylyl, naphthyl, picolyl, pyridyl, quinolyl, pyrimidyl, pyrazinyl, triazolyl, thiadiazolyl, indolyl or optionally benzo-fused imidazole, oxazole or thiazole radicals which optionally carry chlorine, bromine, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -dialkylamino, C.sub.1 -C.sub.8 -alkylsulphonyl, cyano, C.sub.1 -C.sub.8 -alkoxycarbonyl and/or C.sub.1 -C.sub.8 -alkanoylamino,
• R.sup.5 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, amino, C.sub.1 -C.sub.4 -mono-or dialkylamino, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino, or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine,
• R.sup.6 and R.sup.8 independently of one another denote hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino, or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine,
• Y.sup.7 and Y.sup.9 to Y.sup.11 independently of one another denote C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted by chlorine, cyano, methoxycarbonyl, methoxycarbonyloxy, acetyloxy, hydroxyl, methoxy, ethoxy or dimethylamino, cyclohexyl, benzyl, phenyl, which is unsubstituted or substituted by chlorine, cyano, methyl, ethyl, methoxy or ethoxy, or 2,2,6,6-tetramethyl or 1,2,2,6,6-pentamethyl-piperidin-4-yl,
• Y.sup.7' and Y.sup.10' denote hydrogen or have the meaning of Y.sup.7 or Y.sup.10, or
• NY.sup.7 Y.sup.7' and NY.sup.10 Y.sup.10' independently of one another represents a pyrrolidino, piperidino, piperazino, morpholino or pyrazolino radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl and/or phenyl, which can also carry chlorine, methyl, methoxy, ethoxy or cyano.

A pressure-sensitive, heat-sensitive and electro-sensitive recording material comprising a layer support and a color developer and a chromogenic 3,1-benzoxazine of the formula ##STR151## wherein x.sup.11 and X.sup.12 denote NY.sup.12 Y.sup.12', OY.sup.13 or SY.sup.13,

• R.sup.4 denotes hydrogen, C.sub.1 -C.sub.18 -alkyl which optionally carries fluorine, chlorine or C.sub.1 -C.sub.4 -alkoxy, cyclohexyl, benzyl which optionally carries chlorine and/or C.sub.1 -C.sub.18 -alkyl, or phenyl, biphenylyl, naphthyl, picolyl, pyridyl, quinolyl, pyrimidyl, pyrazinyl, triazolyl, thiadiazolyl, indolyl or optionally benzo-fused imidazole, oxazole or thiazole radicals which optionally carry chlorine, bromine, nitro, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, C.sub.1 -C.sub.8 -dialkylamino, C.sub.1 -C.sub.8 -alkylsulphonyl, cyano, C.sub.1 -C.sub.8 -alkoxycarbonyl and/or C.sub.1 -C.sub.8 -alkanoylamino,
• R.sup.5 and R.sup.7 independently of one another denote hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, amino, C.sub.1 -C.sub.4 -mono-or dialkylamino, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino, or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine,
• R.sup.10 denotes hydrogen, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkanoylamino, or C.sub.1 -C.sub.4 -alkylsulphonylamino, or benzoylamino, anilino or N-C.sub.1 -C.sub.4 -alkylanilino radicals which are unsubstituted or substituted by methyl, methoxy, ethoxy or chlorine,
• Y.sup.12 and Y.sup.13 independently of one another denotes C.sub.1 -C.sub.8 -alkyl which is unsubstituted or substituted by chlorine, cyano, methoxycarbonyl, methoxycarbonyloxy, acetyloxy, hydroxyl, methoxy, ethoxy or dimethylamino, cyclohexyl, benzyl, phenyl, which is unsubstituted or substituted by chlorine, cyano, methyl, ethyl, methoxy or ethoxy, or 2,2,6,6-tetramethyl-or 1,2,2,6,6-pentamethylpiperidin-4-yl,
• Y.sup.12' denotes hydrogen or has the meaning of Y.sup.12, or
• NY.sup.12 Y.sup.12' represents a pyrrolidino, piperidino, piperazino, morpholino or pyrazolino radical which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl and/or phenyl, which can also carry chlorine, methyl, methoxy, ethoxy or cyano.