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    • 1. 发明授权
    • Pyrazolonylazoaniline or aminonaphtyl compounds for copying processes
    • 吡唑啉偶氮苯胺或氨基萘啶化合物用于复制工艺
    • US4119622A
    • 1978-10-10
    • US737720
    • 1976-11-01
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • B41M5/136C09B29/00C09B29/036C09B29/06C09B29/24C09B29/08
    • C09B29/24C09B29/0037C09B29/06Y10T428/25
    • An azo compound useful in copying processes of the formula ##STR1## where R.sup.1 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sup.2 and R.sup.3 are each alkyl of 1 to 4 carbon atoms, or one of the radicals R.sup.1, R.sup.2 and R.sup.3 is unsubstituted phenyl or phenyl substituted by alkyl of 1 to 4 carbon atoms, methoxy or ethoxy, and A denotes ##STR2## where R.sup.4 and R.sup.5 are each hydrogen; alkyl of 1 to 8 carbon atoms which may be substituted by hydroxy, alkoxy, halogen or alkoxycarbonyl; cyanoethyl; alkylcarbonyl with 1 to 3 carbon atoms in the alkyl; cyclohexyl; phenalkyl of 7 to 10 carbon atoms; or substituted or unsubstituted phenyl, or R.sup.4 is N,N-dialkylaminoalkyl or N,N-bisphenalkylaminoalkyl, or the group ##STR3## is a 5-membered or 6-membered saturated heterocyclic ring which may contain an --O-- or --S-- group as ring member, Y is hydroxy, alkyl, alkoxy, chlorine, bromine or alkylcarbonylamino, n is 0, 1 or 2, R.sup.6 and R.sup.7 are each hydrogen, alkyl of 1 to 4 carbon atoms, cyclohexyl or unsubstituted phenyl or phenyl substituted by alkyl or alkoxy, and Z is hydrogen, hydroxy, methoxy, ethoxy or a sulfonic acid group. The light absorption of the yellow to orange colored compounds (I) is displaced, upon protonation of the compounds, by 150 to 200 nm toward the longer wavelength range, i.e. the salts are violet to blue in color.The compounds (I) are suitable for the production of pressure-sensitive n.c.r. papers.
    • 用于复制式(I)的方法的偶氮化合物,其中R 1是氢或1至4个碳原子的烷基,R 2和R 3各自是1至4个碳原子的烷基或基团R 1,R 2中的一个 且R 3为未取代的苯基或被1至4个碳原子的烷基取代的苯基,甲氧基或乙氧基,A表示其中R 4和R 5各自为氢; 可以被羟基,烷氧基,卤素或烷氧基羰基取代的1至8个碳原子的烷基; 氰乙基; 在烷基中具有1至3个碳原子的烷基羰基; 环己基 7至10个碳原子的苯基烷基; 或取代或未取代的苯基,或R4是N,N-二烷基氨基烷基或N,N-双酚烷基氨基烷基,或者“IMAGE”是5元或6元饱和杂环,其可以含有-O-或-S- 作为环成员,Y是羟基,烷基,烷氧基,氯,溴或烷基羰基氨基,n是0,1或2,R 6和R 7各自是氢,1至4个碳原子的烷基,环己基或未被取代的苯基或被 烷基或烷氧基,Z是氢,羟基,甲氧基,乙氧基或磺酸基。 当化合物质子化时,黄色至橙色化合物(I)的光吸收在较长波长范围内被移位150至200nm,即盐为紫色至蓝色。
    • 3. 发明授权
    • 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes
    • 2,2'-螺二苯并吡喃的7,7'-二氨基衍生物
    • US4316027A
    • 1982-02-16
    • US894095
    • 1978-04-06
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • B41M5/15C07D493/10C07D491/22C09B57/00
    • C07D493/10B41M5/15
    • Dye intermediates of the formula ##STR1## where R.sup.1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, chlorine or bromine, or phenylalkyl of 7 to 10 carbon atoms, R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together are dimethylene, trimethylene or tetramethylene, which are unsubstituted or substituted by alkyl of 1 to 12 carbon atoms, R.sup.3 and R.sup.5 are hydrogen, alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or trimethylene which is unsubstituted or substituted by 1 to 3 methyl and is bonded to the carbon atom in the 6-position or 6'-position of the benzene ring, R.sup.4 and R.sup.6 are alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, phenylalkyl of 7 to 10 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, chlorine or bromine, or trimethylene bonded to the carbon atom in the 8-position or 8'-position of the benzene ring, or one or both of the groups ##STR2## are a pyrrolidine, piperidine, morpholine, thiomorpholine, N'-alkylpiperazine (alkyl being of 1 to 4 carbon atoms) or iso-indoline radical, and the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6 may be identical or different and the rings A and A' may be substituted by alkyl of 1 to 3 carbon atoms.The dye intermediates give deep bluish-green to green colorations with electron-attracting substances and may be used for the manufacture of pressure-sensitive recording materials.
    • 其中R 1为氢,1至12个碳原子的烷基,未被取代或被1至4个碳原子的烷基,被甲氧基,乙氧基,氯或溴取代的苯基或7至10个苯基烷基的染料中间体 碳原子,R2是氢或R1和R2一起是二乙烯,三亚甲基或四亚甲基,它们是未取代的或被1至12个碳原子的烷基取代,R 3和R 5是氢,1至12个碳原子的烷基,氰基,氯 - 甲氧基或乙氧基取代的2至4个碳原子的烷基,5至7个碳原子的环烷基,7至10个碳原子的苯基烷基或未取代或被1至3个甲基取代并与碳原子键合的三亚甲基 在苯环的6位或6位,R4和R6是1〜12个碳原子的烷基,2〜4个碳原子的氰基,氯,甲氧基或乙氧基取代的烷基,7位的苯基烷基 至10个碳原子,未取代或被1-4个碳原子的烷基取代的苯基 碳原子,氯或溴,或与苯环的8位或8位的碳原子键合的三亚甲基,或者一个或两个基团,即吡咯烷,哌啶,吗啉,硫代吗啉,N 烷基哌嗪(烷基为1至4个碳原子)或异二氢吲哚基,取代基R 3,R 4,R 5和R 6可以相同或不同,并且环A和A'可以被1至3的烷基取代 碳原子。 染料中间体用吸引电子的物质产生深蓝绿色至绿色,可用于制造压敏记录材料。
    • 5. 发明授权
    • Pressure-sensitive recording material
    • 压敏记录材料
    • US4147509A
    • 1979-04-03
    • US868211
    • 1978-01-09
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • B41M5/136B41M5/15C07D493/10C09B57/00D06P5/00B41L1/16
    • C07D493/10B41M5/15Y10S8/919
    • A pressure-sensitive recording material which comprises a substrate bearing a dye-forming component and a binder. The dye-forming component is a spirodipyran of the formula ##STR1## where A is the radical of a fused benzene or naphthalene ring (which rings may or may not be substituted), R.sup.1 is alkyl of 1 to 16 carbon atoms, substituted or unsubstituted phenyl or phenalkyl of 7 to 10 carbon atoms, R.sup.2 is H or together with R.sup.1 is a trimethylene or tetramethylene bridge which is unsubstituted or substituted by from 1 to 3 alkyl, R.sup.3 is benzyl or .beta.-phenylethyl and R.sup.4 is benzyl, .beta.-phenylethyl or substituted or unsubstituted phenyl, or R.sup.3 is alkyl of 1 to 4 carbon atoms and R.sup.4 is substituted or unsubstituted phenyl or R.sup.3 is benzyl and R.sup.4 is .beta.-cyanoethyl. The recording materials give violet to bluish green colorations (copies) only on paper coated with an electron acceptor.
    • 一种压敏记录材料,其包含承载染料形成成分和粘合剂的基材。 染料形成组分是式IMAGE的螺二甲苯,其中A是稠合苯或萘环的基团(该环可以被取代或不被取代),R 1是1至16个碳原子的烷基,取代或未取代的 7至10个碳原子的苯基或苯基烷基,R2是H或与R1一起是未被取代或被1-3个烷基取代的三亚甲基或四亚甲基桥,R3是苄基或β-苯乙基,R4是苄基,β-苯乙基 或取代或未取代的苯基,或R3是1至4个碳原子的烷基,R4是取代或未取代的苯基或R3是苄基,R4是β-氰基乙基。 记录材料仅在涂有电子受体的纸上给予紫色至蓝绿色(复印)。
    • 6. 发明授权
    • 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes
    • 7,7 {40-二氨基衍生物2,2(40-螺二苯并吡喃)
    • US4110348A
    • 1978-08-29
    • US773337
    • 1977-03-01
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • B41M5/15C07D493/10C07D311/02
    • C07D493/10B41M5/15
    • Dye intermediates of the formula ##STR1## where R.sup.1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, chlorine or bromine, or phenylalkyl of 7 to 10 carbon atoms, R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together are dimethylene, trimethylene or tetramethylene, which are unsubstituted or substituted by alkyl of 1 to 12 carbon atoms, R.sup.3 and R.sup.5 are hydrogen, alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or trimethylene which is unsubstituted or substituted by 1 to 3 methyl and is bonded to the carbon atom in the 6-position or 6'-position of the benzene ring, R.sup.4 and R.sup.6 are alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, phenylalkyl of 7 to 10 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, chlorine or bromine, or trimethylene bonded to the carbon atom in the 8-position or 8'-position of the benzene ring, or one or both of the groups ##STR2## are a pyrrolidine, piperidine, morpholine, thiomorpholine, N'-alkylpiperazine (alkyl being of 1 to 4 carbon atoms) or iso-indoline radical, and the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6 may be identical or different and the rings A and A' may be substituted by alkyl of 1 to 3 carbon atoms.The dye intermediates give deep bluish-green to green colorations with electron-attracting substances and may be used for the manufacture of pressure-sensitive recording materials.
    • 其中R 1为氢,1至12个碳原子的烷基,未被取代或被1至4个碳原子的烷基,被甲氧基,乙氧基,氯或溴取代的苯基或7至10个苯基烷基的染料中间体 碳原子,R2是氢或R1和R2一起是二乙烯,三亚甲基或四亚甲基,它们是未取代的或被1至12个碳原子的烷基取代,R 3和R 5是氢,1至12个碳原子的烷基,氰基,氯 - 甲氧基或乙氧基取代的2至4个碳原子的烷基,5至7个碳原子的环烷基,7至10个碳原子的苯基烷基或未取代或被1至3个甲基取代并与碳原子键合的三亚甲基 在苯环的6位或6位,R4和R6是1〜12个碳原子的烷基,2〜4个碳原子的氰基,氯,甲氧基或乙氧基取代的烷基,7位的苯基烷基 至10个碳原子,未取代或被1-4个碳原子的烷基取代的苯基 碳原子,氯或溴,或与苯环的8位或8位的碳原子键合的三亚甲基,或者一个或两个基团,即吡咯烷,哌啶,吗啉,硫代吗啉,N 烷基哌嗪(烷基为1至4个碳原子)或异二氢吲哚基,取代基R 3,R 4,R 5和R 6可以相同或不同,并且环A和A'可以被1至3的烷基取代 碳原子。
    • 7. 发明授权
    • 7,7'-Diamino derivatives of 2,2'-spirodibenzopyranes
    • 2,2'-螺二苯并吡喃的7,7'-二氨基衍生物
    • US4345073A
    • 1982-08-17
    • US229651
    • 1981-01-29
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • B41M5/15C07D493/10C07D273/01C07D211/18C07D241/04
    • C07D493/10B41M5/15
    • Dye intermediates of the formula ##STR1## where R.sup.1 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, chlorine or bromine, or phenylalkyl of 7 to 10 carbon atoms, R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together are dimethylene, trimethylene or tetramethylene, which are unsubstituted or substituted by alkyl of 1 to 12 carbon atoms, R.sup.3 and R.sup.5 are hydrogen, alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenylalkyl of 7 to 10 carbon atoms or trimethylene which is unsubstituted or substituted by 1 to 3 methyl and is bonded to the carbon atom in the 6-position or 6'-position of the benzene ring, R.sup.4 and R.sup.6 are alkyl of 1 to 12 carbon atoms, cyano-, chlorine-, methoxy- or ethoxy-substituted alkyl of 2 to 4 carbon atoms, phenylalkyl of 7 to 10 carbon atoms, phenyl which is unsubstituted or substituted by alkyl of 1 to 4 carbon atoms, chlorine or bromine, or trimethylene bonded to the carbon atom in the 8-position or 8'-position of the benzene ring, or one or both of the groups ##STR2## are a pyrrolidine, piperidine, morpholine, thiomorpholine, N'-alkylpiperazine (alkyl being of 1 to 4 carbon atoms) or isoindoline radical, and the substituents R.sup.3, R.sup.4, R.sup.5 and R may be identical or different and the rings A and A' may be substituted by alkyl of 1 to 3 carbon atoms.The dye intermediates give deep bluish-green to green colorations with electron-attracting substances and may be used for the manufacture of pressure-sensitive recording materials.
    • 其中R 1为氢,1至12个碳原子的烷基,未被取代或被1至4个碳原子的烷基,被甲氧基,乙氧基,氯或溴取代的苯基或7至10个苯基烷基的染料中间体 碳原子,R2是氢或R1和R2一起是二乙烯,三亚甲基或四亚甲基,它们是未取代的或被1至12个碳原子的烷基取代,R 3和R 5是氢,1至12个碳原子的烷基,氰基,氯 - 甲氧基或乙氧基取代的2至4个碳原子的烷基,5至7个碳原子的环烷基,7至10个碳原子的苯基烷基或未取代或被1至3个甲基取代并与碳原子键合的三亚甲基 在苯环的6位或6位,R4和R6是1〜12个碳原子的烷基,2〜4个碳原子的氰基,氯,甲氧基或乙氧基取代的烷基,7位的苯基烷基 至10个碳原子,未取代或被1-4个碳原子的烷基取代的苯基 碳原子,氯或溴,或与苯环的8位或8位的碳原子键合的三亚甲基,或者一个或两个基团,即吡咯烷,哌啶,吗啉,硫代吗啉,N 烷基哌嗪(烷基为1〜4个碳原子)或异吲哚基,取代基R3,R4,R5和R可以相同或不同,环A和A'可以被1〜3个碳原子的烷基取代 。 染料中间体用吸引电子的物质产生深蓝绿色至绿色,可用于制造压敏记录材料。
    • 8. 发明授权
    • Spirodipyrans
    • US4161589A
    • 1979-07-17
    • US932015
    • 1978-08-08
    • Hans BaumannAndreas Oberlinner
    • Hans BaumannAndreas Oberlinner
    • C07D493/06B41M5/136B41M5/15C07D493/10C09B57/00
    • C07D493/10B41M5/15
    • Spirodipyrans of the formula ##STR1## where A is the radical of a fused benzene ring or 2,1-naphthalene ring, the rings being unsubstituted or substituted by alkyl, alkoxy, nitro, chlorine, bromine or carbalkoxy,R.sup.1 is alkyl, phenyl, substituted alkyl or phenalkyl andR.sup.2 is hydrogen, orR.sup.1 and R.sup.2 together are trimethylene which is unsubstituted or substituted by 1, 2 or 3 alkyl andB is N-morpholinyl, substituted morpholinyl, thiomorpholinyl-S-dioxide, N-(N'-alkyl)-piperazinyl or N-isoindolinyl,And pressure-sensitive recording materials containing these spirodipyrans as dye-forming components.With electron acceptors, the spirodipyrans give reddish violet to blue colorations, while no coloration is produced on paper which has not been coated with an electron acceptor.
    • 其中A是稠合苯环或2,1-萘环的基团,该环是未取代的或被烷基,烷氧基,硝基,氯,溴或烷氧基取代的芳基,R1是烷基,苯基, 取代的烷基或苯基烷基,R 2是氢,或者R 1和R 2一起是未被取代或被1,2或3个烷基取代的三亚甲基,B是N-吗啉基,取代的吗啉基,硫代吗啉基-S-二氧化物, 烷基) - 哌嗪基或N-异吲哚啉基,以及包含这些螺旋体作为成型组分的压敏记录材料。