JPH0426606B2 - - Google Patents

Description

[Detailed description of the invention]

"Industrial Application Field" The present invention relates to a method for producing an acyllactam-functional substance, more specifically, a method for producing an acyllactam-functional substance, and more specifically, a method for producing an acyllactam-functional substance by anionic polymerization using a basic polymerization catalyst of a polyamide-based polymer containing ω-lactam as a main raw material. The present invention relates to a method for preparing high molecular weight acyllactam functional materials useful as polymerization initiators from low molecular weight acyllactam compounds and polyols or polyamines. ``Prior Art'' Polymers containing polyamide segments and segments of another polymeric material are known in the art and are referred to as ``nylon block polymers.'' . By combining polyamide segments with segments of another polymeric material,
The ability to obtain block polymers with various distinctive properties has been demonstrated, for example, in JP-A No. 11668/1983.
Publication No., Special Publication No. 7559, Special Publication No. 1977-
Publication No. 22348, Special Publication No. 1972-35367, Special Publication No. 1972
-50239 Publication, Japanese Patent Publication No. 54-40120, Japanese Patent Publication No.
It is known and described in JP-A-58-13627, JP-A-58-21423, JP-A-58-21425, and the like. The properties of these block polymers can be changed by changing the type, molecular weight, etc. of the polyamide and/or other polymeric material in the block polymer. Such block polymers are particularly suitable for use as fibers, fabrics, films and molding resins. In the nylon block polymer described in the above publication, the acyllactam functional substance serves as a polymerization initiator for the block polymer. Acyl lactam functional materials are known to be produced by reacting acid halides with polyols to produce acid halide functional materials and then reacting this reaction product with lactams. There is. In the process of reacting acid hydrides and polyols to produce acid halide-functional materials and the subsequent process of producing acyllactam-functional materials, dehydrohalogenating agents (hereinafter simply dehydrohalogenating agents) such as triethylamine and pyridine are usually used. Coexist with hydrochloric acid agent (labeled as hydrochloric acid agent). The product obtained after the completion of this reaction contains the hydrochloride of the dehydrochlorination agent as an impurity, so it is necessary to separate and remove it. In order to separate and remove the hydrochloride salt of the dehydrochlorination agent from the reaction target product, a water washing method or another method is usually adopted. However, it is extremely difficult to separate and remove the hydrochloride of the dehydrochlorination agent mixed into the organic compound by washing with water, especially when the organic compound is a polymeric substance. In the case of another method, the target reaction product and the hydrochloride salt of the dehydrochlorination agent are usually separated by utilizing the difference in solubility in a certain solvent, but the selection of the solvent is difficult. Even if a good solvent is available,
If the viscosity of the reaction target product is high, it is necessary to use a large amount of solvent or to pass the reaction at high temperatures, and this method is also accompanied by practical difficulties. The previously known methods of producing acid halide functional materials and then N-acyl lactams have the drawbacks mentioned above. Therefore, it has been desired to develop an industrially advantageous method for producing acyllactam-functional substances that eliminates the above-mentioned drawbacks. "Problems to be Solved by the Invention" The problems to be solved by the present invention are as follows. That is, it is an object of the present invention to provide an industrially advantageous method for producing an acyllactam-functional substance by effectively removing the hydrochloride of a dehydrochlorination agent produced as a by-product in the process of producing the substance. "Means for Solving Problems" The gist of the present invention is as follows: Formula (1) [In the formula, A is

[Formula] (where Y is a C ₃ to C ₁₁ alkylene), a is an integer of 2 or more, and Z is a C ₀ to _{C 20} aliphatic, alicyclic, or aromatic hydrocarbon an acyllactam compound represented by the group ]; and a polyol having one or more hydroxyl groups per molecule and having a molecular weight of about 1000 or more,
or has one or more amino groups bonded to at least one hydrogen atom per molecule, and has a molecular weight of about
It is characterized by reacting one or more substances selected from 1000 or more polyamines in the presence of a nitrogen-containing 6-membered ring system or fused 6-membered ring system heterocyclic compound as a catalyst. The present invention relates to a method for producing an acyllactam-functional substance. In addition, in the explanation of the above formula (1), in the description that Z is a hydrocarbon group such as a C ₀ -C ₂₀ aliphatic group, C ₀ -
C ₂₀ means 0 to 20 carbon atoms, and 0 carbon atoms means, for example, when a in formula (1) is an integer of 2, formula (1) is

It refers to a compound represented by the formula: The present invention will be explained in detail below. The acyllactam-functional materials of the present invention are produced from two steps described below. The first step is to use a polyhydric acid halide compound and
- lactam in the presence of a dehydrochlorination agent in an organic solvent to liberate the hydrochloride of the dehydrochlorination agent as crystals, and the hydrochloride is separated by washing with water or separately;
In the method of the present invention, a solution of a low molecular weight acyllactam compound, that is, a compound represented by formula (1) is obtained. This solution may be used as it is in the next second step, or the acyllactam compound can be isolated from this solution by means such as recrystallization or solvent distillation and used in the next second step. . The reaction in this first step is already known, but unlike conventional methods for producing high molecular weight acyllactam functional substances, the resulting acyllactam compound has a low molecular weight. The feature is that it is very easy to remove by washing with water or separately. Washing with water, which is used as a means for removing the hydrochloride of the above-mentioned dehydrochlorination agent, is a preferable method because it does not require any over-equipment and can perform large-scale treatment in a short period of time. The second step (that is, corresponds to the manufacturing method of the present invention)
The low molecular weight acyllactam compound obtained in the first step and one or more substances selected from polyols or polyamines are combined into a nitrogen-containing six-membered ring system or a fused six-membered ring system. The reaction is carried out in an organic solvent using a heterocyclic compound as a catalyst to produce the desired high molecular weight acyllactam functional substance. The discovery of a catalyst that facilitates this second step reaction has completed the process for producing acyllactam-functional materials according to the present invention. The polyhydric acid halide compound used in the first step is represented by the following formula (2): [In the formula, Z is a C ₀ to _{C 20} aliphatic, alicyclic or aromatic hydrocarbon, a is an integer of 2 or more, and X is a halogen]. Specific examples of the compound of formula (2) above include the following substances, but are not limited to the substances listed here. For example, adipoyl chloride, terephthaloyl chloride, isophthaloyl chloride, trimezoyl chloride, trimellitic acid chloride, oxalyl chloride, pyromellitoyl chloride, pimeloyl chloride, glutaryl chloride, benzophenotetracarboxylic acid chloride , oxydiacetyl chloride, oxybenzoyl chloride, sebacic acid chloride, azelaic acid chloride, etc. These may be used alone or in combination of two or more. Furthermore, the ω-lactam used in the first step is expressed by the formula (3) Lactams represented by the formula [wherein Y is _C3 - _C11 alkylene], specific examples include γ-butyrolactam, δ-valerolactam, ε-caprolactam, ω-enantholactam, ω-capryllactam , ω-undecanolactam, ω-laurinlactam, and the like. These ω-lactams may be used alone or in combination of two or more. As the dehydrochlorination agent, a Lewis base which is soluble in an organic solvent and is aprotic can be used. Specific examples include tertiary amines such as triethylamine, triethylenediamine, and N,N-dimethylaniline, and aromatic compounds such as aniline. However, it is not limited to the examples listed here. The solvent used in the first step may be any common organic solvent and is not particularly limited, such as tetrahydrofuran, acetone, methyl ethyl ketone, hexane,
These include benzene, toluene, xylene, etc. However, in the second step, when the solution of the acyllactam compound obtained in the first step is used as it is, benzene, toluene, xylene, etc. are preferable. An example of the method for producing a low molecular weight acyllactam compound in the first step is as follows. First, a predetermined amount of acid chloride is dissolved in a dehydrated solvent in a reaction vessel, and then a mixed solution of an ω-lactam and a dehydrochlorination agent is continuously added while stirring. At this time, ω
- The number of functional groups in the lactam and dehydrochlorination agent should be equal to or slightly larger than the number of functional groups in the acid chloride. The reaction temperature is maintained below the boiling point of the raw materials used until the addition of the ω-lactam and dehydrochlorination agent is completed, and then maintained at the boiling point of the solvent for a necessary time. After that, water heated to near the boiling point of the solvent that is sufficient to sufficiently dissolve the hydrochloride of the dehydrochlorination agent produced as a by-product is added to this reaction vessel, and the hydrochloride is dissolved by stirring, and the stirring is stopped and the water is heated as needed. After allowing it to stand for a while, only the lower layer aqueous solution is extracted. This water washing operation is performed two or more times to obtain an organic solvent solution of the acyllactam compound. The low molecular weight acyllactam compound may be isolated by distilling off the solvent of this solution or by a crystallization operation, and this may be used in the next second step.
Industrially, it is advantageous to use the organic solvent solution as it is in the next second step. In the second step, the acyl lactam compound solution obtained in the first step is first dehydrated. ), one or more polyols or polyamines, a catalyst and, if necessary, a diluting solvent are added to this solution and allowed to react. Although it is efficient to carry out the reaction under reflux of the solvent, the reaction temperature is not particularly limited. The polyol used in the method of the present invention is not particularly limited as long as it has one or more hydroxyl groups per molecule and has a molecular weight of about 1,000 or more, but specific examples include polyether polyols that have at least a molecular weight of about 1,000. , or polyester polyols containing polyether segments having a molecular weight of at least about 1000, and furthermore polyether polyols in which the polyol is derived from a diol, triol or tetraol,
More preferably, the polyol is selected from polyester polyols containing polyether segments derived from diols, triols, or tetraols. Polyether segments are not particularly limited, but include poly(oxyethylene),
Poly(oxypropylene), or poly(oxybutylene), or poly(oxypropylene)
It is industrially advantageous to use a block copolymer of poly(oxyethylene) and poly(oxyethylene). Moreover, as the polyol, the following are preferable. i.e., a polybutadiene polyol having a molecular weight of at least about 1000;
polyester polyols containing polybutadiene segments having a molecular weight of at least about 1000, or hydrogenated polybutadiene polyols having a molecular weight of at least about 1000, or polyester polyols containing hydrogenated polybutadiene segments having a molecular weight of at least about 1000, or the polyol is selected from () a copolymer polyol of butadiene and acrylonitrile having a molecular weight of at least about 1000, or () a polyester polyol containing a copolymer segment of butadiene and acrylonitrile having a molecular weight of at least about 1000; Polydimethyl-, polydiphenyl- or polymethylphenyl-siloxane polyols having a molecular weight of at least about 1000, or polysiloxane polyols containing both dimethylsilylene and diphenylsilylene groups. The polyamine used in the method of the present invention is not particularly limited as long as it has one or more amino groups bonded to at least one hydrogen atom per molecule and has a molecular weight of about 1000 or more, but specific examples are shown below. Some examples include: That is, the polyamine is preferably a polyamine selected from polyether polyamines having a molecular weight of at least about 1000, or polyester polyamines containing polyether segments having a molecular weight of at least about 1000; More preferably, the polyamine is selected from polyether polyamines derived from polyether polyamines, or polyamide polyamines containing polyether segments derived from diols, triols or tetraols. Polyether segments are not particularly limited, but include poly(oxyethylene),
Poly(oxypropylene), or poly(oxybutylene), or poly(oxypropylene)
It is industrially advantageous to use a block copolymer of poly(oxyethylene) and poly(oxyethylene). Also, the polyamine is selected from a polybutadiene polyamine having a molecular weight of at least about 1000, or a polyester polyamine containing polybutadiene segments having a molecular weight of at least about 1000, or a polyamine having a molecular weight of at least about
hydrogenated polybutadiene polyamine with 1000,
or a polyamine selected from a polyamide polyamine containing hydrogenated polybutadiene segments having a molecular weight of at least about 1000, or a copolymer polyamine of butadiene and acrylonitrile having a molecular weight of at least about 1000, or () a copolymer polyamine of butadiene and acrylonitrile having a molecular weight of at least about 1000 a polyamide selected from polyamide polyamines containing copolymer segments of butadiene and acrylonitrile having a molecular weight of at least about 1000;
Polydiphenyl or polymethylphenyl
Preferably, it is a siloxane polyamine or a polysiloxane polyamine having both dimethylsilylene and diphenylsilylene groups. One type or a combination of two or more of these polyols or polyamines is used, and the amount used depends on the type of acyllactam functional substance to be produced and the purpose of the low molecular weight acyllactam compound. The ratio between the number of acyllactam groups and the number of hydroxyl groups in the polyol or amino groups in the polyamine is selected and used. For example, in order to introduce an average of two molecules of polyol having three hydroxyl groups per molecule into an acyllactam functional substance, when a low molecular weight acyllataram compound has two acyl lactam groups per molecule, Two molecules of polyol are reacted with five molecules of a low molecular weight acyllactam compound. Of course, it is clear that the ratio of the raw materials will vary depending on the acyllactam functional substance to be produced and the structure of the low molecular weight acyllactam compound and polyol or polyamine used as raw materials. The nitrogen-containing 6-membered ring system or fused 6-membered ring system heterocyclic compound in the present invention includes pyridine derivatives, pyridazine derivatives, pyrimidine derivatives, pyrazine derivatives, quinoline derivatives, isoquinoline derivatives, cinnoline derivatives, quinazoline derivatives, quinosaline derivatives, They are phthalazine derivatives, pterin derivatives, benzoquinoline derivatives, benzoisoquinoline derivatives, acridine derivatives, or phenazine derivatives. Specific examples include pyridine, picoline, lutidine, ethylpyridine, nicotine, bipyridine, pyridazine, pyrimidine, pyrazine,
Quinoline, lepidine, biquinoline, isoquinoline, cinnoline, quinazoline, quinosaline, phthalazine, pterin, benzo[g]quinoline, benzo[g]isoquinoline, benzo[h]quinoline,
Examples include benzo[f]quinoline, but are not limited to these examples. The amount of the heterocyclic compound to be used varies depending on the reaction temperature and reaction time, and is not particularly limited, but in the case of industrial implementation, 10 ^{- Four} ~
Preferably, 10 ^-1 mol is used. If the amount is less than this, the effect will be weak, while if it is used more than this, it is not economically advantageous. "Effects of the Invention" When the method of the present invention is used, a substance that is a combination of a low molecular weight acyllactam compound from which the hydrochloride of a dehydrochlorination agent produced as a by-product in the manufacturing process can be easily removed, and one or more polyols or polyamines is used. An acyllactam-functional substance can be easily obtained from the above, which has the effect of greatly facilitating the industrial production of the substance, and its industrial utility value is extremely large. "Examples" Next, the present invention will be described with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples unless it exceeds the gist thereof. In order to evaluate the performance of the high molecular weight acyllactam functional substance obtained by the present invention, the molecular weight and nylon block copolymer (hereinafter referred to as NBC) were determined by gel permeation chromatography (hereinafter referred to as GPC) using the following method. The reactivity of the molded article and the tensile properties of the NBC molded article were measured. Molecular weight measurement: GPC; 802UR manufactured by Toyo Soda Co., Ltd., column Toyo Soda
Measurement was performed using G3000+G2000 with tetrahydrofuran solvent. Reactivity: Component system (A) and molding system (B) consisting of the following compositions
were prepared in 500ml flasks each, and the temperature was adjusted to 100℃.
was held at Component system (A) ε-caprolactam 283g Bromomagnesium caprolactam 17g Component system (B) ε-caprolactam 166g acyllactam functional substance 134g Weigh out 100g each of these component systems (A) and (B) into a beaker, and mix with a stirrer. Immediately after mixing, the temperature was controlled to 140℃ using an electric heater.
The mixture was poured into a flat plate mold having a cavity of 200 mm and 3 mm thickness, and held for 3 minutes. At this time, a sensor that detects the temperature of the reaction liquid is embedded in the center of the mold, and the time from when the liquid is injected until the liquid reaches its maximum temperature (heat generation time) is measured, and a sensor with a shorter heat generation time is selected. It was judged that the reactivity was good. Tensile properties: ASTM D-638 type dumbbells were cut out from the above molded product, and after absorbing the saturated moisture content in an atmosphere of 23°C and 50% relative humidity, ASTM D-
638, the tensile strength at break and elongation were measured. Example 1 (First step) In a 500 ml flask equipped with a stirrer, a reflux condenser, an adder, a thermometer, a nitrogen gas inlet, and a gas vent, 100 ml of toluene dehydrated with a molecular sieve was added. Isophthalic acid chloride 20.3
g and heated until the solvent refluxed. Next, while stirring, a solution of 22.7 g of caprolactam and 21.8 g of triethylamine dissolved in 100 ml of toluene was added dropwise over 10 minutes using an adder, and after the addition was completed, the mixture was kept under reflux conditions for 10 minutes. Thereafter, the mixture was cooled to 90°C, 150 ml of 90°C water was added, stirred for a while, allowed to stand, and the aqueous layer separated into layers was removed. The oil layer was further washed with water twice to obtain a toluene solution of biscaprolactam isophthalate. (Second step) To the toluene solution of biscaprolactam isophthalate obtained in the first step, an average of 2.3
After adding 156 g of polybutadiene polyol having an average molecular weight of 2,800 and having several hydroxyl groups, water in the system was azeotropically distilled off together with toluene. While maintaining the reaction system in a toluene reflux state, pyridine was added in an amount equivalent to 5 x 10 ^-2 mol per equivalent of hydroxyl group, the reaction was allowed to proceed for 3 hours, and the toluene was distilled off to form the reaction product ( Acyllactam functional material) was obtained.
The yield was 178 g (yield 100%). The infrared spectrum of the acyllactam functional material is shown in FIG. 1, and it can be seen that it has the desired chemical structure of the acyllactam functional material. The number average molecular weight determined by GPC was 6200, indicating that it had the desired molecular weight. NBC molded articles were made using the acyllactam functional material. The evaluation results of the reactivity and physical properties at that time are shown in Table 1 below. Comparative Example 1 The same polybutadiene polyol as in Example 1 was placed in the same 500 ml flask as used in Example 1.
A solution of 13.0 g of triethylamine dissolved in 50 ml of tetrahydrofuran was added dropwise at a constant rate over 30 minutes while stirring at room temperature. After the dropwise addition was completed, the contents were continuously stirred at room temperature for 3 hours. While stirring the resulting reaction mixture, add 8.2 g of caprolactam to 50 ml of tetrahydrofuran,
A solution containing 8.8 g of triethylamine was added dropwise at a constant rate over 45 minutes. After the dropwise addition was completed, the temperature of the reaction mixture was raised to 68° C. over 30 minutes, and this temperature was maintained for 3 hours while the mixture vapor in the flask was refluxed and cooled. After cooling the reaction mixture to room temperature, the precipitated triethylamine hydrochloride was filtered through a pressure filtration machine (paper; No. 2, pressure: 2.7 Kg/cm ² ) with an overarea of 44 cm ²
So it took us an hour and 30 minutes to separate. The excess residue was washed with 50 ml of tetrahydrofuran, the same operation was repeated twice, and the liquid was mixed with the original liquid. Tetrahydrofuran was distilled off from the mixture to obtain an acyllactam functional material. The yield is
The yield was 152 g (85% yield), which was inferior to Example 1. The main cause was excessive adhesion to the residue. The number average molecular weight determined by GPC was 6100, indicating that it had the desired molecular weight. NBC molded articles were made using the acyllactam functional material. Table 1 shows the evaluation results of the reactivity and physical properties at that time. Comparative Example 2 A reaction mixture was obtained in the same manner as in the example described in Example 1, but without using pyridine in the second step. The number average molecular weight of the reaction mixture by GPC is 2800 (excluding low molecular weight substances),
It was no different from polybutadiene polyol. Examples 2-6 In the example described in Example 1, instead of pyridine in the second step, picoline (Example 2), nicotine (Example 3), bipyridine (Example 4), quinoline (Example 5), Acyllactam functional materials, N, and were obtained in a similar manner to Example 1 using pyrimidine (Example 6). their respective
Number average molecular weight by GPC is 6100, 6300, 6300,
6200 and 6100, and it was found that they had the desired molecular weights. And the yield (yield) is as shown in Example 2.
175g (98%) in Example 3, 173g in Example 3
(97%), 177g (99%) in Example 4, 176g (98%) in Example 5, 175g in Example 6
g (98%). Using these acyllactam functional substances,
I made NBC molded products. Table 1 shows the evaluation results of the reactivity and physical properties at that time. Examples 7-13 In the example described in Example 1, the polybutadiene polyol in the second step is replaced by an ethylene oxide end-capped poly(oxypropylene) triol having an average molecular weight of 4800 and having an average of 3 hydroxyl groups per molecule. (Example 7), average molecular weight 1000 with an average of 2 hydroxyl groups per molecule
66.7 g of polyoxybutylene polyol (Example 8), 131 g of hydrogenated polybutadiene polyol with an average molecular weight of 1700 having an average of 1.8 hydroxyl groups per molecule (Example 9), having an average of 2.3 hydroxyl groups per molecule. 167 g of a copolymer of butadiene and acrylonitrile (acrylonitrile content 15% by weight) with an average molecular weight of 3000 (Example 10), 1
Average molecular weight with an average of 2 hydroxyl groups per molecule
66.7g of 1000 polydimethylsiloxane diol
(Example 11), 200 g of polyoxypropylene triamine with an average molecular weight of 5000 and having an average of 3 amino groups per molecule (Example 12), or polybutadiene with an average molecular weight of 3000 and having an average of 2.3 amino groups per molecule. Examples using polyamine (Examples 12 and 13) using 167g of polyamine (Example 13)
An acyllactam functional substance ~ was obtained in the same manner as in the same example except that the reaction time was changed to 2 hours. Their yields and number average molecular weights are shown below.

[Table] Using these acyllactam functional substances
I made NBC molded products. Table 1 shows the evaluation results of the reactivity and physical properties at that time. Example 14 In the example described in Example 7, except that the amount of pyridine in the second step was added in an amount equivalent to 10 ^-1 mol per equivalent of hydroxyl group, and the reaction was carried out for 1 hour. Acyllactam functional properties were obtained in the same manner as in the same example. Yield (yield) is 212g
(98%), and the number average molecular weight was 10,500. Comparison Row 3 The example described in Comparative Example 1, except that 192 g of ethylene oxide-terminated poly(oxypropylene) triol having an average molecular weight of 4800 and having an average of 3 hydroxyl groups per molecule was used instead of the polybutadiene polyol. An acyllactam functional material was obtained in the same manner as in the same example. Yield (yield) is 179
g (84%), which was inferior to Example 7.
The main reason for this was excessive adhesion to the residue.
The number average molecular weight by GPC was 10,600, which was the desired molecular weight. NBC molded articles were made using the acyllactam functional material. Table 1 shows the evaluation results of the reactivity and physical properties at that time. Comparative Example 4 A reaction mixture was obtained in the same manner as in Example 7, but without using pyridine in the second step. The number average molecular weight of the reaction mixture by GPC is 4800 (excluding low molecular weight substances),
It was no different from poly(oxypropylene) triol. Comparative Example 5 In the example described in Example 12, the reaction was carried out in the same manner as in Example 12 without using pyridine in the second step. During the 2-hour reaction, the number average molecular weight by GPC did not rise to the desired level, and after 4 hours, the desired molecular weight was reached and the reaction was stopped. This revealed that the reaction rate was inferior to that of Example 12. The yield was 220 g (99%), and the number average molecular weight was 11,000. Example 15 The same procedure as in Example 1 was repeated, except that 20.3 g of terephthalic acid chloride was used instead of isophthalic acid chloride in the first step, and 17.1 g of 2-pyrrolidone was used instead of caprolactam. An acyllactam functional material was obtained. Yield: 173g (97%), number average molecular weight: 6300
It was hot. An NBC molded article was made using the functional material.
Table 1 shows the evaluation results of the reactivity and physical properties at that time. Example 16 An acyllactam-functional material was obtained in the same manner as in Example 1, except that 18.1 g of adipic acid chloride was used instead of isophthalic acid chloride in the first step. Yield (yield) is 176g (99%), number average molecular weight is
It was 6300. An NBC molded article was made using the functional substance. Table 1 shows the evaluation results of the reactivity and physical properties at that time. As can be seen from the above examples and comparative examples,
The acyllactam-functional substance obtained by the method of the present invention has a reactivity and NBC that is no different from that of the acyllactam-functional substance obtained by the conventional method.
It shows the physical properties when made into a molded product.

【table】

【table】 [Brief explanation of drawings]

FIG. 1 is an infrared spectrum diagram of the acyllactam functional material of the present invention prepared according to Example 1 in the text.

Claims (1)

[Claims] 1 Formula (1) [Wherein, A is [Formula] (where Y is C ₃ to C ₁₁ alkylene), a is an integer of 2 or more, and Z is C ₀ to C ₂₀ aliphatic or alicyclic or an aromatic hydrocarbon group], and a polyol having one or more hydroxyl groups per molecule and a molecular weight of about 1000 or more,
or has one or more amino groups bonded to at least one hydrogen atom per molecule, and has a molecular weight of about
It is characterized by reacting one or more substances selected from 1000 or more polyamines in the presence of a nitrogen-containing 6-membered ring system or fused 6-membered ring system heterocyclic compound as a catalyst. Method for producing acyllactam functional substances. 2 The polyol () has a molecular weight of at least about 1000
polyether polyol having or ()
Claim 1 is a polyol selected from polyester polyols containing polyether segments having a molecular weight of at least about 1000.
A method for producing the acyllactam-functional substance described in Section 1. 3. The claimed polyol is a polyol selected from () polyether polyols derived from diols, triols or tetraols, or () polyester polyols containing polyether segments derived from diols, triols or tetraols. A method for producing an acyllactam functional material according to scope 2. 4. Claims in which the polyether is poly(oxyethylene), poly(oxypropylene), or poly(oxybutylene), or a block copolymer of poly(oxypropylene) and poly(oxyethylene) A method for producing an acyllactam-functional substance according to item 2 or 3. 5 The polyol () has a molecular weight of at least about 1000
2. The method of claim 1, wherein the polyol is selected from polyester polyols containing polybutadiene segments having a molecular weight of at least about 1000. 6 The polyol () has a molecular weight of at least about 1000
or () a polyester polyol containing hydrogenated polybutadiene segments having a molecular weight of at least about 1000. 7 The polyol () has a molecular weight of at least about 1000
or a polyester polyol containing a butadiene and acrylonitrile copolymer segment having a molecular weight of at least about 1000. A method for producing acyllactam functional substances. 8. The polyol according to claim 1, wherein the polyol is a polydimethyl-, polydiphenyl- or polymethylphenyl-siloxane polyol having a molecular weight of at least about 1000, or a polysiloxane polyol containing both dimethylsilylene and diphenylsilylene groups. Method for producing acyllactam functional substances. 9 The polyamine () has a molecular weight of at least about 1000
polyether polyamine with or ()
2. A method for making an acyllactam functional material according to claim 1, wherein the polyamine is selected from polyamide polyamines containing polyether segments having a molecular weight of at least about 1000. 10 The claimed polyamine is a polyamine selected from () polyether polyamines derived from diols, triols or tetraols, or () polyamide polyamines containing polyether segments derived from diols, triols or tetraols. A method for producing an acyllactam functional material according to scope 9. 11 Polyether is poly(oxyethylene),
Poly(oxypropylene), or poly(oxybutylene), or poly(oxypropylene)
A method for producing an acyllactam-functional material according to claim 9 or claim 10, which is a block copolymer of acyl lactam and poly(oxyethylene). 12 The polyamine () has a molecular weight of at least about
1000, or polyamide polyamines containing polybutadiene segments having a molecular weight of at least about 1000. 13 The polyamine () has a molecular weight of at least about
hydrogenated polybutadiene polyamine with 1000,
or () a polyamide polyamine containing hydrogenated polybutadiene segments having a molecular weight of at least about 1000. 14 The polyamine () has a molecular weight of at least about
1000, or a polyamide polyamine containing a butadiene and acrylonitrile copolymer segment having a molecular weight of at least about 1000. A method for producing the described acyllactam functional material. 15. The acyl according to claim 1, wherein the polyamine is a polydimethyl-, polydiphenyl- or polymethylphenyl-siloxane polyamine having a molecular weight of at least about 1000 or a polysiloxane polyamine having both dimethylsilylene and diphenylsilylene groups. Method for producing lactam-functional substances. 16 Nitrogen-containing 6-membered ring or fused 6-membered ring heterocyclic compound is pyridine derivative, pyridazine derivative, pyrimidine derivative, pyrazine derivative, quinoline derivative, isoquinoline derivative, cinnoline derivative, quinazoline derivative, quinosaline derivative, phthalazine derivative, pterin A method for producing an acyllactam-functional substance according to any one of claims 1 to 15, which is a benzoquinoline derivative, a benzoisoquinoline derivative, an acridine derivative, or a phenazine derivative.