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Description  |
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BACKGROUND OF THE INVENTION
(a) Field of the Invention
This invention relates to unsaturated cyclic amido-substituted ether
compounds and their preparation process. More specifically, it relates to
unsaturated cyclic amido-substituted ether compounds, in each of which at
least one hydroxyl group of an OH-substituted cyclic compound has been
substituted by an unsaturated amidopolymethylenoxy group, and their
preparation process. The unsaturated cyclic amido-substituted ether
compounds of this invention can be used in crosslinking agents, adhesives,
paints and raw materials for hygroscopic resins as well as in various
other fields.
(b) Description of the Prior Art
Cyclic compounds have permitted relatively easy introduction of various
substituent groups owing to their cyclic structures. This feature is not
seen in aliphatic compounds, whereby making them suitable as raw materials
for functional materials. When using them as functional materials, it is
however necessary to increase their molecular weights, generally by fixing
them to side chains of monomers so that they are insolubilized.
No general method has however been established to date for the fixing of
such cyclic compounds into high molecular compounds. Except for a few
examples seen among styrene derivatives, the functionality of these cyclic
compounds has thus not been fully utilized under the circumstances.
As skeletal compounds of fixing base materials, N-substituted amide
derivatives have some advantageous characteristics unseen in other
skeletal compounds such as esters, ethers and hydrocarbon derivatives,
including their better compatibility with a variety of materials, their
resistance to hydrolysis, etc. compared with such other skeletal
compounds.
SUMMARY OF THE INVENTION
Interested with a variety of functionality which cyclic compounds have, the
present inventors have carried out an extensive investigation with a view
toward fixing such cyclic compounds and developing functional polymers
containing amido groups in their skeletal structures. As a result, they
have found unsaturated cyclic amido-substituted ether compounds in each of
which a hydroxyl group of an OH-substituted cyclic compound and the amido
group of acrylic amide or methacrylic amide are bonded by way of a
polymethylene group and their preparation process, leading to completion
of this invention.
The unsaturated cyclic amido-substituted ether compounds can be prepared by
reacting cyclic halogen-substituted ether compounds with unsaturated amide
compounds in the presence of a strong basic substance in an aprotic polar
solvent.
The compounds of this invention are unsaturated cyclic amido-substituted
ether compounds each represented by the following general formula (I):
##STR1##
wherein R.sub.1 and R.sub.1 ' are each a cyclic group; Z means an alkylene
group having 1-5 carbon atoms, an alkenylene group having 2-5 carbon
atoms, an oxyalkylene group represented by the general formula
--O--C.sub.x H.sub.2x).sub.r (r: integer of 1-50; x: integer of 1-5) or an
aminoalkylene group represented by the general formula
##STR2##
A and A' each denotes a halogen atom, hydroxyl group, oxo group, cyano
group, nitro group, mercapto group, sulfo group or a salt thereof, an
alkyl group having 1- 20 carbon atoms, an alkenyl group having 2-15 carbon
atoms, a haloalkyl group having 1-20 carbon atoms, an amino or aminoalkyl
group represented by the general formula
##STR3##
hydrogen atom, lower alkyl group or .omega.-unsaturated amidopolymethylene
group represented by the general formula
##STR4##
n being an integer of 4-20and R.sub.3 being a hydrogen atom or methyl
group; R"': lower alkylene group), a group represented by the general
formula RO--, RCO-- or RCOO-- (R: alkyl group having 1-20 carbon atoms,
alkenyl group having 2-15 carbon atoms or aryl group), a group represented
by the general formula --COOR (R.sub.4 hydrogen atom, alkali metal atom,
alkyl group having 1-20 carbon atoms, alkenyl group having 2-15 carbon
atoms, aryl group or .omega.-unsaturated amidopolymethylene group
represented by the general formula
##STR5##
p being an integer of 4-20 and R.sub.5 being a hydrogen atom or methyl
group; B stands for an oxygen atom, carbonyl group, thio group, sulfonyl
group, azo group, alkylene group having 1-5 carbon atoms or alkenylene
group having 2-5 carbon atoms; R.sub.2 denotes a hydrogen atom or methyl
group; l and l' are each an integer of 0-5; (A)l and (A')l', each means a
combination of 0-5 atoms or groups which may be the same or different and
are selected from the group of the atoms and groups defined above for A
and A'; m stands for an integer of 4-20; .alpha., .alpha.', .beta. and
.beta.' stand each for an integer of 0-4 with a proviso that all of
.alpha.,.alpha.', .beta. and .beta.' do not stand for 0 at the same time;
and q stands for 0 or 1. They are novel compounds which have not been
reported in any literatures.
The compounds of this invention can each be prepared by reacting a cyclic
halogen-substituted ether compound represented by the following general
formula (II):
##STR6##
wherein R.sub.1, R.sub.1 ', Z, A, A', B, q, m, l, l', .alpha.,.alpha.',
.beta. and .beta.' have the same meaning as defined above and X denotes a
halogen atom with an unsaturated amide compound represented by the
following general formula (III):
##STR7##
wherein R.sup.2 has the same meaning as defined above, in the presence of
a strong basic substance in an aprotic polar solvent.
The cyclic halogen-substituted ether compounds which are raw materials
required for the preparation of the compounds of this invention can be
obtained with ease in accordance with a process already proposed by the
present inventors, namely, through reactions between OH-substituted cyclic
compounds and dihaloalkanes.
The following advantageous effects can thus be brought about inter alia
from the practice of this invention.
(i) The process of this invention makes use of OH-substituted cyclic
compounds as raw materials. Therefore, an extremely wide variety of
compounds can be applied as mentioned above. The preparation process of
this invention has an extremely high applicability.
Therefore, a variety of functionality may be expected on the basis of
various interactions. As specific interactions, may be mentioned ionic
interaction, electrostatic interaction, charge-transfer interaction,
.pi.--.pi. interaction, van der Waals interaction and so on.
Furthermore, multi-functional monomers such as crosslinking agents can also
be prepared with ease by using multi-substituted OH-substituted cyclic
compounds as raw materials. New functions which are unseen in conventional
crosslinking agents have been found as new types of crosslinking agents.
(ii) Since an amido group and a cyclic group are bonded together via a
polymethylenoxy group and the chain length of the polymethylenoxy group
can be controlled, flexibility can be imparted to polymers of the
compounds of this invention and the degree of the thus-imparted
flexibility can be controlled. Furthermore, the distance of bonding to an
amido group can be controlled depending on the molecular size of each
cyclic compound. This allows to introduce the amido group in the cyclic
compound without difficulties.
(iii) An amido group is contained as a skeletal structure. Accordingly,
each of the compounds of this invention has intermolecular secondary bond
owing to the hydrogen bond between amido groups. Various properties have
thus been improved including mechanical properties as raw materials.
DETAILED DESCRIPTION OF THE INVENTION
In the compound of this invention represented by the general formula (I),
the halogen indicated by A is chlorine, bromine, iodine or fluorine. In
the general formula (II), the halogen represented by X is chlorine,
bromine or iodine. The carbon ring shown by R.sub.1 is an aromatic or
alicyclic ring or a condensed or combined ring thereof. The hetero atom
which makes up the ring of the heterocyclic ring indicated by R.sub.1 is
oxygen, nitrogen or sulfur. Where two or more ring-forming hetero atoms
are contained, they may be different from each other or one another. For
example, monoheterocyclic rings, carbocyclic rings, condensed heterocyclic
rings of heterocyclic rings, heterocyclic spiro rings, heterocyclic
crosslinking rings, etc. may be mentioned.
As aromatic rings, may be mentioned monocyclic and condensed polycyclic
rings such as benzene, naphthalene, anthracene, pentacene, heptacene and
the like, and those formed of 2-4 of these rings which are bonded
together. As alicyclic rings, may be mentioned monocyclic rings such as
cycloalkanes, cycloalkenes, cycloalkadienes, cycloalkatrienes, etc.,
dimers of cycloalkadienes, hydrides of condensed aromatic polycyclic rings
and those formed of 2-4 of such rings which are bonded together. As such
condensed carbocyclic rings, there are dicyclic and tricyclic rings such
as indene and fluorene as well as partial hydrides of condensed polycyclic
aromatic compounds. Also included are hydrocarbon compounds formed of the
above three types of rings combined together and those formed by
substituting hetero atoms such as oxo group to ring-forming carbons.
Where A means a haloalkyl group, the above-described alkyl group contains
at least one halogen atom substituted thereto. Where two or more halogen
atoms are contained, they may be different halogen atoms.
The compounds of this invention are more specifically those obtained using,
as basic skeletal structures, those formed of carbocyclic rings such as
aromatic or alicyclic rings or their condensed or combined rings, or
heterocyclic rings such as monoheterocyclic, condensed heterocyclic rings
of carbocyclic rings or heterocyclic rings, heterocyclic spiro rings,
crosslinked heterocyclic rings and hydroxyl groups bonded to the
carbocyclic rings or heterocyclic rings either directly or via alkylene,
alkenylene, oxyalkylene and/or aminoalkylene groups and substituting at
least one of the hydroxyl groups with .omega.-unsaturated
amidopolymethylenoxy group or groups. Also included are those obtained by
introducing such substituent groups as referred to above with respect to A
into carbocyclic rings or heterocyclic rings.
Certain representative examples of the compounds according to this
invention will hereinafter be given by way of example. Since an extremely
wide variety of compounds are included in the compounds of this invention,
exemplary listing of compounds will first be made by changing R.sub.1,
R.sub.1 ', Z, A, A', B, l, l', .alpha., .alpha.', .beta., and .beta.' and
q in various ways while setting m and R.sub.2 respectively at 4 and a
hydrogen atom in the general formula (1) for the sake of simplified
exemplification. Then, further exemplary listing will be made by changing
R.sub.2 to a hydrogen atom or methyl group and m 4-20 while setting
R.sub.1 at a benzene ring, .alpha., .alpha.' and .beta.' respectively at
0, q at 0, and l' and l respectively at 0.
Among substituted derivatives of compounds which contained OH-substituted
carbocyclic rings, illustrative of substituted derivatives of alicyclic
monohyric alcohols include:
N-(4-Cyclobutoxybutyl)acrylic amide;
N-(4-Cyclopentyloxybutyl)acrylic amide;
N-(4-Cylohexyloxybutyl)acrylic amide;
N-[4-(1-Methylcyclopentyloxy)butyl]acrylic amide;
N-[4-(2-Cyclohexenyloxy)butyl]acrylic amide;
N-(4-Cycloheptyloxybutyl)acrylic amide;
N-[4-(Cyclohexylmethoxy)butyl]acrylic amide;
N-[4-(2-Cyclopentylethoxy)butyl]acrylic amide;
N-[4-(4-Methylcyclohexyloxy)butyl]acrylic amide;
N-[4-(2-Cyclohexylethoxy)butyl]acrylic amide;
N-(4-Cyclooctyloxybutyl)acrylic amide;
N-[4-(2,5-Dimethylcyclohexyloxy)butyl]acrylic amide;
N-[4-(3,5-Dimethylcyclohexyloxy)butyl]acrylic amide;
N-[4-(1-Ethynylcyclohexyloxy)butyl]acrylic amide;
N-[4-(2-n-Propylcyclohexyloxy)butyl]acrylic amide;
N-[4-(3,3,5-Trimethylcyclohexyloxy)butyl]acrylic amide;
N-(4-Dicyclopentadienyloxybutyl)acrylic amide;
2-(4-Acrylamidobutoxy)adamantane;
2-(4-Acrylamidobutoxy)-1,7,7-trimethylbicyclo[
2.2.1]heptane;
N-[4-(5-Methyl-2-(1-methylvinyl)cyclohexyloxy)butyl]acrylic amide;
N-[4-(Dimethyl-(4-methyl-3-cyclohexenyl)methoxybutyl]acrylic amide;
N-[4-(1-Methyl-4-(1-methylvinyl)cyclohexyloxy)butyl]acrylic amide;
N-[4-(1-Methyl-4-isopropylidenecyclohexyloxy)butyl]acrylic amide;
N-[4-(4-tert-butylcyclohexyloxy)butyl]acrylic amide;
N-[4-(5-Methyl-2-isopropylcyclohexyloxy)butyl]acrylic amide;
1-(4-Actylamidobutoxymethyl)adamantane;
N-(4-Cyclododecyloxybutyl)acrylic amide;
N-[4-(2-Cyclohexylcyclohexyloxy)butyl]acrylic amide;
N-[4-(4-Cyclohexylcyclohexyloxy)butyl]acrylic amide;
3-(4-Acrylamidobutoxy)-3-cholestane;
3-(4-Acrylamidobutoxy)cholestane;
3-(4-Acrylamidobutoxy)stigmasta-5,22-diene;
3-(4-Acrylamidobutoxy)-6-stigmastene;
3-(4-Acrylamidobutoxy)lanosta-8,24-diene;
N-[4-(2-Chlorocyclohexyloxy)butyl]acrylic amide;
N-[4-(5-Oxo-2-methyl-1-cyclopentenyloxy)butyl]acrylic amide;
3-(4-Acrylamidobutoxy)-5-androsten-17-one;
17-(4-Acrylamidobutoxy)-4-androsten-3-one;
3-(4-Acrylamidobutoxy)-5-androstan-17-one;
17-(4-Acrylamidobutoxy)-5-androstan-3-one;
17-(4-Acrylamidobutoxy)-17-methyl-4-androsten-3-one;
17-(4-Acrylamidobutoxy)-17-ethynyl-4-androsten-3-one;
11-(4-Acrylamidobutoxy)progesterone;
3-(4-Acrylamidobutoxy)-5-pregnen-20-one;
21-Acetoxy-17-(4-acrylamidobutoxy)-4-pregnen-3,11,20-trione;
17-(Acrylamidobutoxy)-3-benzoyloxyestra-1,3,5(10)-triene; and the like.
As substituted derivatives of monohydric alcohols which contain aromatic
rings, may for example be mentioned:
N-(4-Phenoxybutyl)acrylic amide;
N-(4-Benzyloxybutyl)acrylic amide;
N-[4-(2-Methylphenoxy)butyl]acrylic amide;
N-[4-(3-Methylphenoxy)butyl]acrylic amide;
N-[4-(4-Methylphenoxy)butyl]acrylic amide;
N-[4-(1-Phenylethoxy)butyl]acrylic amide;
N-[4-(2-Phenylethoxy)butyl]acrylic amide;
N-[4-(2,4-Dimethylphenoxy)butyl]acrylic amide;
N-[4-(3,5-Dimethylphenoxy)butyl]acrylic amide;
N-[4-(3-Ethylphenoxy)butyl]acrylic amide;
N-[4-(4-Ethylphenoxy)butyl]acrylic amide;
N-[4-(4-Methylbenzyloxy)butyl]acrylic amide;
N-[4-(1-Methyl-2-phenylethoxy)butyl]acrylic amide;
N-[4-(1-Methyl-1-phenylethoxy)butyl]acrylic amide;
N-[4-(3-Phenylpropoxy)butyl]acrylic amide;
N-[4-(4-Isopropylphenoxy)butyl]acrylic amide;
N-[4-(2-n-Propylphenoxy)butyl]acrylic amide;
N-[4-(4-n-Propylphenoxy)butyl]acrylic amide;
N-[4-(2,3,5-Trimethylphenoxy)butyl]acrylic amide;
N-[4-(3,4,5-Trimethylphenoxy)butyl]acrylic amide;
N-[4-(2-Allylphenoxy)butyl]acrylic amide;
N-[4-(1-(4-Methylphenyl)ethoxy)butyl]acrylic amide;
N-[4-(3-Phenyl-2-propenyloxy)butyl]acrylic amide;
N-[4-(1-Phenyl-2-propenyloxy)butyl]acrylic amide;
1-(4-Acrylamidobutoxy)indane;
2-(4-Acrylamidobutoxy)indane;
5-(4-Acrylamidobutoxy)indane;
N-[4-(1,1-Dimethyl-2-phenylethoxy)butyl]acrylic amide;
N-[4-(4-n-Butylphenoxy)butyl]acrylic amide;
N-[4-(2-sec-Butylphenoxy)butyl]acrylic amide;
N-[4-(4-sec-Butylphenoxy)butyl]acrylic amide;
N-[4-(2-tert-Butylphenoxy)butyl]acrylic amide;
N-[4-(3-tert-Butylphenoxy)butyl]acrylic amide;
N-[4-(4-tert-Butylphenoxy)butyl]acrylic amide;
N-[4-(1-Methyl-3-phenylpropoxy)butyl]acrylic amide;
N-[4-(2-Methyl-5-isopropylphenoxy)butyl]acrylic amide;
N-[4-(2,3,5,6-Tetramethylphenoxy)butyl]acrylic amide;
N-[4-(3-Isopropylbenzyloxy)butyl]acrylic amide;
1-(4-Acrylamidobutoxy)naphthalene;
2-(4-Acrylamidobutoxy)naphthalene;
2-(4-Acrylamidobutoxy)-5,6,7,8-tetrahydronaphthalene;
N-[4-(1,1-Dimethyl-3-phenylpropoxy)butyl]acrylic amide;
N-[4-(4-n-Pentylphenoxy)butyl]acrylic amide;
N-[4-(4-(1,1-Dimethylpropyl)phenoxy)butyl]acrylic amide;
N-[4-(2-tert-Butyl-6-methylphenoxy)butyl]acrylic amide;
N-[4-(2,6-Diisopropylphenoxy)butyl]acrylic amide;
N-[4-(6-tert-Butyl-2,4-dimethylphenoxy)butyl]acrylic amide;
N-[4-(2-Cyclohexylphenoxy)butyl]acrylic amide;
N-[4-(3-Cyclohexylphenoxy)butyl]acrylic amide;
N-[4-(4-Cyclohexylphenoxy)butyl]acrylic amide;
N-[4-(2-Phenylphenoxy)butyl]acrylic amide;
N-[4-(3-Phenylphenoxy)butyl]acrylic amide;
N-[4-(4-Phenylphenoxy)butyl]acrylic amide;
N-[4-(Diphenylmethoxy)butyl]acrylic amide;
N-[4-(4-Benzylphenoxy)butyl]acrylic amide;
N-[4-(1,1-Diphenylethoxy)butyl]acrylic amide;
N-[4-(1,2-Diphenylethoxy)butyl]acrylic amide;
N-[4-(2,4-Di-tert-butylphenoxy)butyl]acrylic amide;
N-[4-(2,6-Di-tert-butylphenoxy)butyl]acrylic amide;
N-[4-(4-(1,1,3,3-Tetramethylbutyl)phenoxy)butyl]acrylic amide;
N-[4-(4-Nonylphenoxy)butyl]acrylic amide;
N-[4-(2,6-Di-tert-butyl-4-methylphenoxy)butyl]acrylic amide;
N-[4-(4-(1-Methyl-1-phenylethyl)phenoxy)butyl]acrylic amide;
N-[4-(4-tert-butyl-2,6-diisopropylphenoxy)butyl]acrylic amide;
N-[4-(2,4,6-Tri-sec-butylphenoxy)butyl]acrylic amide;
N-[4-(2,4,6-Tri-tert-butylphenoxy)butyl]acrylic amide;
N-[4-(Triphenylmethoxy)butyl]acrylic amide; and the like.
As substituted derivatives obtained by substituting one or more halogen or
haloalkyl groups to the aromatic rings of the above-described compounds,
may for example be mentioned:
N-[4-(3-Fluorophenoxy)butyl]acrylic amide;
N-[4-(4-Fluorophenoxy)butyl]acrylic amide;
N-[4-(2-Chlorophenoxy)butyl]acrylic amide;
N-[4-(4-Chlorophenoxy)butyl]acrylic amide;
N-[4-(2-Bromophenoxy)butyl]acrylic amide;
N-[4-(3-Bromophenoxy)butyl]acrylic amide;
N-[4-(4-Iodophenoxy)butyl]acrylic amide;
N-[4-(2,3-Dichlorophenoxy)butyl]acrylic amide;
N-[4-(2,4-Dichlorophenoxy)butyl]acrylic amide;
N-[4-(2,6-Dichlorophenoxy)butyl]acrylic amide;
N-[4-(3,4-Dichlorophenoxy)butyl]acrylic amide;
N-[4-(3,5-Dichlorophenoxy)butyl]acrylic amide;
N-[4-(2,4-Dibromophenoxy)butyl]acrylic amide;
N-[4-(2,3,4-Trichlorophenoxy)butyl]acrylic amide;
N-[4-(2,4,5-Trichlorophenoxy)butyl]acrylic amide;
N-[4-(2,4,6-Trichlorophenoxy)butyl]acrylic amide;
N-[4-(2,4,6-Tribromophenoxy)butyl]acrylic amide;
N-[4-(2,3,4,6-Tetrachlorophenoxy)butyl]acrylic amide;
N-[4-(Pentachlorophenoxy)butyl]acrylic amide;
N-[4-(Pentabromophenoxy)butyl]acrylic amide;
N-[4-(3-Chlorobenzyloxy)butyl]acrylic amide;
N-[4-(4-Chlorobenzyloxy)butyl]acrylic amide;
N-[4-(4-Chloro-2-methylphenoxy)butyl]acrylic amide;
N-[4-(4-Chloro-3-methylphenoxy)butyl]acrylic amide;
N-[4-(2-Chloro-6-methylphenoxy)butyl]acrylic amide;
N-[4-(2-Bromo-4-methylphenoxy)butyl]acrylic amide;
N-[4-(2,4-Dichloro-6-methylphenoxy)butyl]acrylic amide;
N-[4-(2-Trifluoromethyl)phenoxy)butyl]acrylic amide;
N-[4-(2-Bromomethyl)-4,6-dibromophenoxy)butyl]acrylic amide;
N-[4-(4-Bromomethyl)-2,6-dibromophenoxy)butyl]acrylic amide;
N-[4-(Pentafluorobenzyloxy)butyl]acrylic amide;
N-[4-(4-Chloro-3,5-dimethylphenoxy)butyl]acrylic amide;
N-[4-(1-(4-Chlorophenylethoxy)butyl]acrylic amide;
N-[4-(2,4-Dichloro-3,5-dimethylphenoxy)butyl]acrylic amide;
1-(4-Acrylamidobutoxy)-4-chloronaphthalene;
N-[4-(4-tert-Butyl-2-chlorophenoxy)butyl]acrylic amide;
N-[4-(4-Chloro-5-methyl-isopropylphenoxy)butyl]acrylic amide;
2-(4-Acrylamidobutoxy)-1-bromonaphthalene;
2-(4-Acrylamidobutoxy)-6-bromonaphthalene;
N-[4-(2-Bromo-4-tert-butylphenoxy)butyl]acrylic amide;
1-(4-Acrylamidobutoxy)-2,4-dichloronaphthalene;
1-(4-Acrylamidobutoxy)-2,4-dibromonaphthalene;
N-[4-(2-Chloro-4-phenylphenoxy)butyl]acrylic amide;
N-[4-(2-Benzyl-4-chlorophenoxy)butyl]acrylic amide; etc.
As those obtained by substituting alkoxy groups to the aromatic rings of
the above-described compounds and substituted derivatives obtained by
bonding alkoxy groups to such aromatic rings via oxygen atoms, may for
example be mentioned:
N-[4-(3-Methoxyphenoxy)butyl]acrylic amide;
N-[4-(4-Methoxyphenoxy)butyl]acrylic amide;
N-[4-(4-Methoxybenzyloxy)butyl]acrylic amide;
N-[4-(2-Methoxy-4-methylphenoxy)butyl]acrylic amide;
N-[4-(4-Ethoxyphenoxy)butyl]acrylic amide;
N-[4-(3,5-Dimethoxyphenoxy)butyl]acrylic amide;
N-[4-(2-Phenoxyethoxy)butyl]acrylic amide;
N-[4-(3,4-Dimethoxybenzyloxy)butyl]acrylic amide;
N-[4-(2-Benzyloxyethoxy)butyl]acrylic amide;
N-[4-(1-Methyl-2-phenoxyethoxy)butyl]acrylic amide;
N-[4-(2-(4-Methylphenoxy)ethoxy)butyl]acrylic amide;
N-[4-(3-n-Butoxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Butoxyphenoxy)butyl]acrylic amide;
N-[4-(4-Allyl-2-methoxyphenoxy)butyl]acrylic amide;
N-[4-(2-Methoxy-4-(1-propenyl)phenoxy)butyl]acrylic amide;
N-[4-(4-n-Pentyloxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Butoxybenzyloxy)butyl]acrylic amide;
N-[4-(2-tert-Butyl-4-methoxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Hexyloxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Heptyloxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Benzyloxyphenoxy)butyl]acrylic amide;
N-[4-(4-n-Octyloxyphenoxy)butyl]acrylic amide;
17-(4-Acrylamidobutoxy)-17-ethynyl-3-methoxy-1,3,5(10)-estratriene;
N-[4-(Phenoxy)polyethoxybutyl]acrylic amide [CH.sub.2
.dbd.CH--CO--NH--CH.sub.2).sub.4 O--CH.sub.2 CH.sub.2 --O).sub.n C.sub.6
H.sub.5 ; n=5, 7.5, 10, 15, 18, 20];
N-[4-((4-Nonylphenoxy)polyethoxy)butyl]acrylic amide [CH.sub.2
.dbd.CH--CO--NH --CH.sub.2 ).sub.4 O--CH.sub.2 CH.sub.2 --O).sub.n C.sub.6
H.sub.5 -C.sub.9 H.sub.19 ; n.dbd.5, 7.5, 10, 15, 18, 20 ];
N-[4-(2-(4-Chlorophenoxy)ethoxy)butyl]acrylic amide; and etc.
As those obtained by substituting cyano, nitro, amino and/or aminoalkyl
groups to the aromatic rings of the above-described compounds or
substituted derivatives formed by bonding such groups to the aromatic
rings via azo groups, may for example be mentioned:
N-[4-(4-Cyanophenoxy)butyl]acrylic amide;
N-[4-(2-Nitrophenoxy)butyl]acrylic amide;
N-[4-(3-Nitrophenoxy)butyl]acrylic amide;
N-[4-(4-Nitrophenoxy)butyl]acrylic amide;
N-[4-(2-Chloro-4-nitrophenoxy)butyl]acrylic amide;
N-[4-(4-Chloro-2-nitrophenoxy)butyl]acrylic amide;
N-[4-(2,6-Dichloro-4-nitrophenoxy)butyl]acrylic amide;
N-[4-(2,4-Dinitrophenoxy)butyl]acrylic amide;
N-[4-(2,5-Dinitrophenoxy)butyl]acrylic amide;
N-[4-(4-Methyl-3-nitrophenoxy)butyl]acrylic amide;
N-[4-(2-Methyl-4-nitrophenoxy)butyl]acrylic amide;
N-[4-(3-Nitrobenzyloxy)butyl]acrylic amide;
N-[4-(4-Nitrobenzyloxy)butyl]acrylic amide;
N-[4-(4-Nitro-3-trifluoromethylphenoxy)butyl]acrylic amide;
N-[4-(3,5-Dinitro-2-methylphenoxy)butyl]acrylic amide;
N-[4-(2-Methoxy-5-nitrophenoxy)butyl]acrylic amide;
N-[4-(2-Anilinoethoxy)butyl]acrylic amide;
.alpha.-(4-Acrylamidobutoxy)benzyl cyanamide;
N-[4-(5-Dimethylamino-2-nitrophenoxy)butyl]acrylic amide;
N-[4-(3-(Dimethylamino)phenoxy)butyl]acrylic amide;
N-[4-(Dimethylaminomethylphenoxy)butyl]acrylic amide;
N-[4-(2-Amino-1-phenylpropoxy)butyl]acrylic amide;
N-[4-(2-(2-Methylphenylamino)ethoxy)butyl]acrylic amide;
2-(4-Acrylamidobutoxy)-1-nitronaphthalene;
1-(4-Acrylamidobutoxy)-2,4-dinitronaphthalene;
N-[4-(2-(N-ethylanilino)ethoxy)butyl]acrylic amide;
N-[4-(3-(diethylamino)phenoxy)butyl]acrylic amide;
N-[2-(4-Acrylamidobutoxy)ethyl]phthalimide;
N-[4-(1-(3-(Dimethylamino)phenyl)ethoxy)butyl]acrylic amide;
N-[4-(4-(2-(Dimethylamino)ethyl)phenoxy)butyl]acrylic amide;
N-[4-(2-(N-(2-Cyanoethyl)ani | | |
