Abstract:
Novel C6 to C18 liquid, branched-chain, N-α-alkylacrylamides, their use as reactive diluents and dye and pigment dispersants for radiation curable compositions, and radiation curable compositions containing them are disclosed.

Description:
BACKGROUND OF THE INVENTION 
     This invention relates to compositions of matter classified in the art of chemistry as N-alkylacrylamides, to processes for their use and to radiation curable compositions containing them. 
     The use of a Ritter reaction between acrylonitrile and C 12 , C 14 , C 16  and C 18  α-olefins is disclosed by Clarke et al in Journal of the American Oil Chemists Society, Vol. 44, pp. 78 to 82 (1964). The products obtained are solid at room temperature. 
     U.S. Pat. No. 3,796,578 to Keizo Hosoi et al indicates the use of &#34;N-hexylacrylamide&#34; in radiation curable compositions for use on printing plates. The compositions are rather specialized in their requirements and it is nowhere suggested that other than linear 1-alkyl N-substituents of up to 6 carbon atoms would be suitable for use in said compositions. Copies of the publication and the patent accompany this application for the convenience of the Examiner. 
     SUMMARY OF THE INVENTION 
     The invention provides in a composition aspect, a compound of the Formula I: ##STR1## Wherein R is hydrogen or methyl; and R&#39; is an α-methyl substituted straight chain alkyl radical of from 5 to 10 carbon atoms, or a poly-branched alkyl radical of about 6 to about 18 carbon atoms. 
     The tangible embodiments of this composition aspect of the invention possess the inherent physical properties of being liquids at normal room temperature, of being substantially insoluble in water, and soluble in common organic solvents such as aromatic hydrocarbons, e.g. benzene or toluene; lower alkanols, e.g., ethanol, methanol; dimethyl acetamide; acetonitrile and the like and being of low vapor pressure under normal use conditions. 
     The tangible embodiments of this composition aspect of the invention possess the inherent applied use characteristics of being reactive diluents for radiation curable polymer systems, of being colorant dispersants indicating usefulness in the formulation of radiation curable pigmented or dye containing inks and coatings, and of being radiation curable coatings and impregnants for fabrics including woven and non-woven textiles and paper, such impregnation or coating improving surface finish and feel, oil and water repellency and wearing properties. The compositions are also of low toxicity to experimental animals in standard irritation screening. 
     Preferred embodiments of this composition aspect of the invention are those compounds of Formula I wherein R&#39; is a poly-branched alkyl radical of from 9 to about 18 carbon atoms. Special mention is made of those embodiments wherein R&#39; is derived from propylene trimer, tetramer, or the trimer dimerized. Special mention is also made of those compositions wherein the alkyl radical is a mixture of at least 2 radicals of different carbon atom content. 
     The invention further provides a curable composition which comprises an acrylate substituted prepolymer; and a compound of Formula I. 
     The invention further provides a curable composition which comprises a colorant and a compound of Formula I. 
     The invention further provides an ultraviolet curable composition which comprises an ultraviolet radiation cure accelerator and a compound of Formula I. 
     The invention further provides an article of manufacture which comprises a substrate comprising a woven or non-woven textile or a non-woven web of cellulosic fibers coated or impregnated with a curable composition comprising a compound of Formula I. 
     DESCRIPTION OF THE PREFERRED EMBODIMENT 
     The manner of making and using the compositions of the invention will now be illustrated with reference to a specific embodiment thereof and compositions containing same; namely, N-nonylacrylamide (Ia) prepared from propylene trimer (II). 
     II is a commercially available material prepared by the acid catalyzed random trimerization of propylene. To prepare Ia, II, acrylonitrile, and a free radical inhibitor, conveniently phenothiazine, may be warmed slightly above room temperature, conveniently at about 40° to 45° C. in concentrated sulfuric acid containing some water, conveniently about 85% acid, for a short period of time, conveniently about 4 to 24 hours. After cooling to room temperature, any unreacted II may be separated. Ia may, if desired, be recovered from the remaining reaction mixture by standard techniques, conveniently by pouring the reaction mixture into ice water, adding toluene, separating the 2 phases which form, washing the organic phase with water and sodium carbonate solution, drying and evaporating the organic phase in vacuo to give Ia as a liquid residue. 
     One skilled in the art will recognize that instead of the above described II and acrylonitrile, one may substitute either methacrylonitrile or other known α-olefins such as 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-undecene, propylene tetramer, propylene trimer dimerized by treatment with a Lewis acid such as BF 3 ,1,3,4,5,-tetramethyl-2-ethylheptene-1  and the like to prepare the other amides contemplated by Formula I. It will similarly be obvious to one skilled in the art that mixtures of olefins of the type contemplated as starting materials for the compounds of Formula I are also known and if subjected to a Ritter reaction under conditions analogous to those described herein above with either acrylonitrile or methacrylonitrile will produce compounds of Formula I wherein R&#39; will be a mixture of alkyl residues. Such mixtures are contemplated by Formula I both in the specification and in the appended claims. 
     In the processes for the use of the compounds of Formula I their incorporation into standard radiation curable formulations as reactive diluents and/or as dye and pigment dispersants is contemplated. 
     For example, one may add Ia to an acrylated epoxidized vegetable oil, an ultraviolet light sensitizer, such as diethoxy acetophenone and any desired adjuvants, such as other reactive diluents, plasticizers, colorants, such as dyes or pigments and surfactants, coat the mixture onto a desired substrate and subject the coated substrate to ultraviolet light to produce a cured film on the substrate. 
     One skilled in the art will recognize that analogous compositions may be used for electron beam curing and that the presence of an ultraviolet light sensitizer will be unnecessary for such use. 
     For use as inks containing colorants, the standard colorants, either dyes or pigments, may be dispersed in compounds of Formula I together with any desired standard ink adjuvants such as adhesiveness or flow control agents, opaquing agents, and viscosity control agents and if the ink is to be cured by ultraviolet light, an ultraviolet cure accelerator. 
     Similarly for impregnating and coating fabrics and papers, compounds of Formula I, in addition to any standard adjuvants, may be applied to the material by standard methods followed by cure by electron beam or ultraviolet radiation. 
     Useful coatings and impregnants curable by ultraviolet radiation for use particularly in connection with non-woven cellulosic materials, such as paper and the like, may be obtained by the admixture of a compound of Formula I and an ultraviolet cure accelerator. 
     In the specification and the appended claims, the optional use of any and all standard adjuvants as mentioned herein above is comprehended by the invention. 
     As used herein and the appended claims the term α-methyl substituted straight chain alkyl of 5 to 10 carbon atoms comprehends an alkyl radical of the average formula ##STR2## wherein n is 3 to 8; the term poly-branched alkyl radical of about 6 to 18 carbon atoms comprehends alkyl radicals of the specified number of carbon atoms having at least 2 chain branching points in the molecule. 
     One skilled in the art will recognize that the propylene trimers and tetramers, the dimerized propylene trimer and dimerized and trimerized mixtures of olefins of varying chain length comprehended among the starting materials for compounds of Formula I will be mixtures of all possible modes of addition of the monomers and that amides of such mixtures as well as of any single branched chain isomer thereof which may be separable either before or after formation of the N-alkyl amide are comprehended as part of this invention. 
     One skilled in the art will also recognize that for amides of poly-branched alkyl radicals of greater than about 12 carbon atoms, it will be necessary to have mixtures of alkyl chains, particularly mixtures of at least 2 varying chain length alkyl radicals to insure liquidity. 
     The acrylic acid residue substituted prepolymers comprehended among the starting materials for the compositions of this invention are those liquid acrylic acid or methacrylic acid substituted prepolymers known in the art. The linkage of the acrylate moiety to the prepolymer chain may be by reaction of the carboxylic acid portion of the acrylate molecule or its equivalent with hydroxyl, epoxy, urethane or amino functions on the prepolymer chain, or by reaction of a hydroxyl substituted acrylate ester with an epoxy, carboxy or urethane function on the prepolymer molecule. 
     Ultraviolet radiation cure accelerators are those standard radiation cure accelerators or mixtures thereof well known in the art. Commonly, these are benzoins, benzophenones, and acetophenones, either unsubstituted or more commonly substituted so as to increase efficiency at selected wavelengths. Use of such compounds in standard fashion in standard concentration ranges is contemplated. 
     Woven or non-woven textiles suitable for use in preparing the coated or impregnated articles of manufacture which are amenable to radiation curing, as well as for use in preparing the radiation cured articles of manufacture, are those known textiles prepared from the common fibers of commerce both natural and synthetic. Included among these fibers are; for example, cotton, linen, rayon, wool, polyester fibers, polyether fibers, polyamide fibers, polyurethane fibers, carbon fibers, and the like. 
     Non-woven cellulosic fiber webs include the common papers and like products of commerce; such as, rag papers, ground wood pulp papers, kraft papers and the like. 
    
    
     The following examples further illustrate the best mode contemplated by the inventor for the practice of his invention. 
     EXAMPLE 1 
     N-Nonylacrylamide 
     To a mixture of propylene trimer (504 parts by weight (pbw)) acrylonitrile (232 pbw), and phenothiazine (0.4 pbw) is added 85% sulfuric acid (510 pbw) at 40°-45° C. over a period of one hour. The reaction is held at this temperature for an additional four hours, cooled and the upper layer (unreacted olefin, 95 pbw) separated. The lower aqueous layer is decanted into ice water (1500 pbw) and toluene (250 pbw) added. The upper organic layer is washed twice with 100 pbw portions of water, then with 20% sodium carbonate solution (35 pbw) dried over anhydrous sodium sulfate (40 pbw) and evaporated under vacuum to give the title product as a liquid residue (575 pbw). 
     Analysis for: C 12  H 23  NO: 
     Calculated: C,73.04; H,11.75; N,7.10%. 
     Found: C,73.27; H,11.64; N,7.10%. 
     EXAMPLE 2 
     N-Dodecylacrylamide 
     To acrylonitrile (212 pbw), propylene tetramer (673 pbw) and phenothiazine (0.4 pbw) is added 85% sulfuric acid (520 pbw) at 40° C. over a period of one hour. The mixture is held at 40° to 42° C. for 12 hours. After cooling the upper layer of unreacted olefin is separated and the lower layer poured into ice water (1600 pbw). This mixture is stirred overnight then partitioned with 2 portions (500 pbw) of toluene. The combined organic phase is worked with 3 portions of water totalling 300 pbw and then to neutrality with 20% sodium carbonate. After drying over sodium sulfate and the addition of p-methoxyphenol, the solution is concentrated in vacuo to obtain the title product as a viscous yellow liquid (572 pbw). 
     EXAMPLE 3 
     N-(α-methylpentyl)acrylamide 
     Following a procedure analogous to that of Examples 1 and 2 from 530 pbw of acrylonitrile, 841.6 pbw hexene-1, 1.0 pbw phenothiazine and 1300 pbw 83% sulfuric acid, there is obtained 1010 pbw of the title product. 
     EXAMPLE 4 
     Toxicity screening of N-Nonylacrylamide 
     N-nonyl-acrylamide was tested according to the protocol established for the Federal Hazardous Substances Act. 
     The material is fed to fasted male and female albino rats in a geometric progression series of doses ranging from 2.0 to 64.0 mg/Kg of body weight. Animals are observed for deaths over a period of 2 weeks. The oral LD 50  found was 7430 mg/Kg of body weight. 
     The material is applied to hair free partially abraded skin of albino rabbits and held in place by a polyethylene sleeve over the test area for 24 hours, the skin cleaned and examined, following which the animals are observed for 2 weeks. Among six male and female albino rabbits, there were no deaths indicating a lack of acute dermal toxicity. 
     The test substance was tested for acute inhalation toxicity by exposing 10 adult male and female albino rats to an aerosol of the substance in an inhalation chamber for one hour. The animals were observed for a 2 week period following exposure and then sacrificed. All animals survived the observation period and no gross abnormalities were observed on autopsy after sacrifice. 
     The test substance was examined for eye irritation potential by introducing the test substance into the conjunctival sacs of the unwashed eyes of 6 albino rabbits. Evaluations of the results were made at 24, 48 and 72 hours according to the standardized scoring scheme established for the test. In this test score results below 5.0 indicate negligible potential for eye irritation. The test substance scored 4.3. 
     EXAMPLE 5 
     Ultraviolet light curable formulations are prepared containing the ingredients shown in Table I. The viscosity of each finished formulation is as shown. Films are cast on release paper from each formulation. In this and the following examples, prepolymer A is a hydroxyl terminated ethylene propylene 80/20 adipate polyester of about 2800 molecular weight capped with toluene diisocyanate then end-capped with 2-hydroxyethyl acrylate. Prepolymer B is a hydroxyl terminated poly(ethylene adipate), of about 600 molecular weight capped with toluene diisocyanate then endcapped with 2-hydroxyethyl acrylate. Prepolymer C is a hydroxy terminated poly(ethylene adipate) of molecular weight about 600 capped with hydrogenated methylene dianiline then endcapped with 2-hydroxyethyl acrylate. Prepolymer D is a hydroxyl terminated poly(ethylene adipate) of molecular weight about 600 capped with isophorone diisocyanate then endcapped with 2-hydroxyethyl acrylate, Actomer X-80 is an acrylic acid adduct to epoxidized vegetable oil supplied by Union Carbide Corp., Melcril 5919 is the reaction product of hydroxyalkyl acrylate with melamine formaldehyde resin supplied by Daubert Chemical Co., Epocryl 370 is an adduct of bisphenol A diglycidyl ether and acrylic acid supplied by Shell Chemical Co. 
     
                                           TABLE I__________________________________________________________________________             Formulation No.Ingredient (pbw)  1  2      3    4   5   6__________________________________________________________________________Prepolymer C      60 60Prepolymer D                70Actomer X-80                     70Melcril 5919                         70Epocryl 370                             70N-(α-methylpentyl)acrylamide (Ex 3)             25 20     30   30  15 30Ethoxyethoxyethyl acrylate             15 20              15V-Pyrol                     14.4Dioctylphthalate                        20Diethoxyacetophenone             2  2      2    2   2Benzophenone                            2.5Dimethylaminoethanol                    2.5Viscosity (centistokes)             5500                2500 &gt;14,800                       &gt;14,800                            12,000                                240                                   810__________________________________________________________________________ 
    
     
                       TABLE II______________________________________After complete cure under ultraviolet light,properties of cast films are as shown in Table II.   Formulation No.   1     2       3       4    5      6______________________________________Tensile (psi)     1800    1470    2925  2540 Shattered                                       3650Elongation (%)      35      55       5    &lt;5  on      &lt;5Modulus (psi)  25%     1620     795    --    --   die    --  50%     --      1310    --    --   cut    -- 100%     --      --      --    --          --Yield (psi)     --      --      2900  --          --Tear (pli)      129     72      244  --          --______________________________________ 
    
     
                                           TABLE III__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedfilms prepared and the properties of said films determined as shown inTable III.              Formulation No.Ingredient (pbw)   1    2    3    4    5     6__________________________________________________________________________Prepolymer C       60   60   60        60Prepolymer A                      70        70N-(α-methylheptyl) acrylamide (Ex 16)              30   25   20   16.8N-nonylacrylamide (Ex 1)               25   17.2Ethoxyethoxyethyl acrylate              10   15   20        15V-Pyrol                           13.2      12.8Diethoxyacetophenone              2    2    2    2    2    2Viscosity (centistokes)              &gt;14,800                   &gt;14,800                        3,200                             &gt;14,800                                  8,100                                       &gt;14,800Physical PropertiesTensile (psi)      1820 1430 865  255  2140 1790Elongation (%)     40   25   35   120  55   185Modulus (psi)  25%              1480 (1300)                        595  90   1510 240  50%                                  (2280)  100%                            190       510Tear (pli)         124  85   67   43   113  138__________________________________________________________________________ 
    
     
                                           TABLE IV__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined,films cast and cured and the properties of said films determined as shownin Table IV.              Formulation No.Ingredient (pbw)   1    2    3    4    5__________________________________________________________________________Prepolymer C       70   60   60   60Prepolymer A                           70N-(α-methylnonyl) acrylamide (Ex 17)              15   30   25   20   17.6Ethoxyethoxyethyl acrylate              15   10   15   20V-Pyrol                                12.4Diethoxyacetophenone              2    2    2    2    2DC-11 (Dow Corning Silicone              1    1    1    1  Surfactant)UCC L-7602 (Union Carbide Corp.  Silicone Surfactant)                 1Viscosity (centistokes)              &gt;14,800                   &gt;14,800                        &gt;14,800                             5500 &gt;14,800Physical PropertiesTensile (psi)      1240 900  940  1165 85Elongation (%)     35   30   35   65   120Modulus (psi)  25%              995  765  725  330  100%                                 60Tear               80   99   69   42   12__________________________________________________________________________ 
    
     
                                           TABLE V__________________________________________________________________________Ultraviolet curable compositins are prepared, their viscositiesdetermined, curedfilms prepared and the properties of said films determined as shown inTable V.              Formulation No.Ingredient (pbw)   1    2    3    4    5    6    7__________________________________________________________________________Prepolymer C       70   60   60   60Prepolymer A                           70Prepolymer B                                70   60N-Dodecylacrylamide (Ex 2)              15   30   25   20   18.4 15   20Ethoxyethoxyethyl acrylate              15   10   15   20        15   20V-Pyrol                                11.6Diethoxyacetophenone              2    2    2    2    2    2    2DC-11              1    1    1    1         1    1UCC L-7602                             1Viscosity (centistokes)              &gt;14,800                   22 14,800                        &gt;14,800                             &gt;14,800                                  &gt;14,800                                       &gt;14,800                                            8,100PropertiesTensile (psi)      1680 1680 1570 1110 480  1510 445Elongation (%)     35   20   30   35   130  45   30Modulus (psi)  25%              1440      1400 810  110  795  310  100%                                 285Tear (pli)         102  123  105  68   120  69   32__________________________________________________________________________ 
    
     
                                           TABLE VI__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedprepared and the properties of said films determined as shown in TableVI.              Formulation No.Ingredient (pbw)   1    2    3    4    5    6    7    8__________________________________________________________________________Prepolymer C       60   60   60   60   60   60   60   60N-(αmethylheptyl              25   20 acrylamideN-Nonylacrylamide (Ex 1)     25   20N-(α-methylnonyl) (Ex 17)        25   20 acrylamideN-Dodecyclacrylamide (Ex 2)                      25   20Phenoxyethyl acrylate              15   20   15   20   15   20   15   20Diethoxyacetophenone              2    2    2    2    2    2    2    2DC-11              1    1    1    1    1    1    1    1Viscosity (centistokes)              &gt;14,800                   12,000                        &gt;14,800                             8,100                                  &gt;14,800                                       &gt;14,800                                            &gt;14,800                                                 &gt;14,800PropertiesTensile (psi)      1700 &gt;    2160 2590 1130 1915 2030 1880Elongation (%)     50   50   40   55   25   50   25   25Modulus (psi)  25%              1245 1410 1910 1810      1210 (1965)                                                 1830 50%                    2000      2330      1820Tear (pli)         133  135  174  161  72   97   160  160__________________________________________________________________________ 
    
     
                                           TABLE VII__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedprepared and the properties of said films determined as shown in TableVII.              Formulation No.Ingredient (pbw)   1    2    3    4    5    6    7__________________________________________________________________________Prepolymer C       60   60   60   60        70Prepolymer B                           70        60N-Nonylacrylamide (Ex 1)              30   20             15   15   20N-Dodecylarylamide (Ex 2)    30   20Ethoxyethoxyethyl acrylate              10   20   10   20   15   15   20Diethoxyacetophenone              2    2    2    2    2    2    2DC-11              1    1    1    1    1    1    1Viscosity          &gt;14,800                   2500 &gt;14,800                             4100 12,000                                       12,000                                            4100PropertiesTensile (psi)      2000 1400 1710 1460 2320 2180 1815Elongation (%)     5    35   15   40   45   35   65Modulus (psi) 25%                    (1030)    965  1510 1705 1150Tear (pli)                             132  140  67__________________________________________________________________________ 
    
     
                                           TABLE VIII__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedfilms prepared and the properties of said films determined as shown inTable VIII.              Formulation No.Ingredient (pbw)   1    2    3  4      5    6    7__________________________________________________________________________Prepolymer C       60                            60Prepolymer D                      70   70Acetomer X-80           70Melcril 5919                 70Epocryl 370                                 70N-Nonylacrylamide (Ex 1)              20   30   15   30   30   30   30Ethoxyethoxyethyl acrylate              20   15                       10Dipropylene Glycol dibenzoate          20Dioctylphthlate                             20Diethoxyacetophenone              2    2     2   2    2         2Benzophenone/Dimethylamino- ethanol (II)                               5.0DC-11              1    1     1   1    1         1UCC L-7602                                  1Viscosity          3200 &gt;14,800                        215  &gt;14,800                                  &gt;14,800                                       12,000                                            &gt;14,800PropertiesTensile (psi)      1610 (2430)                        shattered                             2490 1080 2780 1930Elongation (%)     55   (&lt;5) on   15   50   &lt;5   15Modulus (psi)                die 25%               730       cut       590 50%               1240                950Tear (pli)         54__________________________________________________________________________ 
    
     
                                           TABLE IX__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedfilms prepared and the properties of said films determined as shown inTable IX.              Formulation No.Ingredient (pbw)   1    2    3    4    5    6__________________________________________________________________________Prepolymer B            70Prepolymer C                 70   60   60   60Prepolymer A       70N-(α-methylpentyl, α-methyl-              14.6 15   15   20hexyl) acrylamide (Ex 15)N-(α-methylpentyl) acrylamide (Ex 3)                                  30   25Ethoxyethoxyethyl acrylate                   15   15   20   10   15V-Pyrol            15.4Diethoxyacetophenone              2    2    2    2    2    2DC-11                   1    1    1    1    1DC-1180 (silicone surfactantDow Corning)       2Viscosity (centistokes)              &gt;14,800                   8100 12,000                             2000 8100 2500PropertiesTensile (psi)      600  2370 2340 1240 2250 2250Elongation (%)     140  50   35   50   45   55Modulus (psi)  25%              150  1260 1830 705  1760 1320  50%                                       1980  100%             375Tear (pli)         83   117  129  59    189 120__________________________________________________________________________ 
    
     
                                           TABLE X__________________________________________________________________________Ultraviolet curable compositions are prepared, their viscositiesdetermined, curedfilms prepared and the properties of said films determined as shown inTable X.              Formulation No.Ingredient (pbw)   1    2    3    4    5    6__________________________________________________________________________Prepolymer C       60        60   60   60Prepoloymer A           70                  70N-(α-methylpentyl) acrylamide (Ex 3)              20   15.6N-(α-methylheptyl) acrylamide (Ex 16)                        30   25   20   16.8Ethoxyethoxyethyl acrylate              20        10   15   20V-Pyrol                 14.4                13.2Diethoxyacetophenone              2    2    2    2    2    2DC-11              1         1    1    1Viscosity (centistokes)              1500 &gt;14,800                        &gt;14,800                             4100 1500 &gt;14,800PropertiesTensile (psi)      1565 1120 1190 1120 760  935Elongation (%)     55   165  40   55   50   160Modulus (psi)  25%              715  190  820  480  310  160  50%              1240           930 100%                   435                 350Tear (pli)         66   98   65   44   30   130__________________________________________________________________________ 
    
     EXAMPLE 14 
     Ultraviolet Curable Colorant Dispersion 
     A dispersion of &#34;Microlith&#34; Blue 4G-T (an insoluble, dispersable organic pigment Ciba-Geigy) (20 weight %) and N-nonylacrylamide (Ex 1) (80 wt %) is prepared by ball milling. This dispersion is blended with trimethylol propane triacrylate at a number of weight ratios and the resulting compositions are painted on aluminum foil with a brush and cured in a PPG QC processor with 2 lamps, focused, in air, at a line speed of 20 feet per minute. At pigment dispersion/trimethylol propane triacrylate weight ratios of 1:1 and 2:1 the cured surfaces were tack free and no pigment could be rubbed off when wiped with a ball of cotton. 
     EXAMPLE 15 
     N-(α-methylpentyl,α-methyl-hexyl)acrylamide 
     Following a procedure analogous to that of Example 1, treat acrylonitrile with a mixture of 1-hexene and 1-heptene in the presence of 83% sulfuric acid and phenothiazine to obtain the title product. 
     EXAMPLE 16 
     N-(α-methylheptyl)acrylamide 
     Following a procedure analogous to that of Example 1, treat acrylonitrile with 1-octene in the presence of phenothiazene and 83% sulfuric acid to obtain the title product. 
     EXAMPLE 17 
     N-(α-methylnonyl)acrylamide 
     Following a procedure analogous to that of Example 1, treat acrylonitrile with 1-decene in the presence of phenothiazine and 83% sulfuric acid to obtain the title product.