Functional polymers and their production

Abstract: A functional polymer whose molecules have a main chain of carbon-carbon bonds and one or more pendant functional groups each appended to the main chain via a carbonylimino-­ carbonyl linkage, in which the or each functional group is chosen from fluorinated, aminotriazine, photosensitive, bicyclic and spiro structure-containing groups, and in which the content of the functional groups plus the carbonylimino-­ carbonyl linkages per molecule is from 0.1 to 99.9% by weight.

Description: The present invention relates to functional polymers, to their production, and to intermediates therein. In particular, it relates to polymers comprising a main chain of carbon-carbon bonds and pendant functional groups appended to the main chain via a carbonyliminocarbonyl (-CONHCO-) linkage. In recent years, a great variety of polymers have been artificially produced and used in various fields. There are still demands for new polymers having better physical properties. It is an object of the present invention to provide polymers having good elasticity, good adhesion and favourable dispersibility. EP-A-0037590 discloses a polymer that comprises a main chain of carbon-carbon bonds and at least one pendant functional group of the formula -CO-NH-CO-NH-CO-(CH₂) m -NR₃⁺Z⁻ This polymer has characteristic water-solubility, due to the terminal quaternary ammonium group. According to the present invention, a novel functional polymer has a molecular weight of 1,000 to 100,000, a main chain of carbon-carbon bonds and 0.1 to 99.9% by weight of one or more pendant functional groups of the formula -CO-NH-CO-R m wherein R m is a melamine group. Novel intermediates have the formula CH₂=CR-CO-NH-CO-R m A first process for preparing a polymer according to the invention comprises (1-a) polymerising an alkenoyl isocycanate of formula I CH₂=CR-CO-NCO (I) wherein R is H or C₁₋₅, and, optionally, one or more other polymerisable monomers having no active hydrogen atom, the monomers containing at least 0.1% by weight of the alkenoyl isocyanate; and (1-b) reacting the resultant polymer with an active hydrogen atom-containing compound of formula II R m -H (II) wherein R m is as defined above. In step (1-a), the polymerisation may be carried out by a per se conventional procedure, particularly by solution polymerisation. For instance, a monomeric mixture comprising the alkenoyl isocyanate (I) and optionally one or more polymerisable monomers in an inert solvent, preferably comprising a polymerisation initiator, is maintained at a temperature of 20 to 200°C, favourably of 60 to 150°C, more favourably of 80 to 110°C, for 0.5 to 5 hours. If used, the amount of the polymerisation initiator may be from 0.1 to 10% by weight, preferably from 0.5 to 5% by weight, based on the total weight of the monomers. When desired, a chain transfer agent may be also present in the reaction system. The amount of the chain transfer agent is usually from 5 to 20% by weight, based on the total weight of the monomers. In step (1-b), the addition may be also carried out by a per se conventional procedure. For instance, the isocyanatocarbonyl group-containing polymer is reacted with the functional group-containing compound (II) in an inert solvent at a temperature of -20 to 100°C, preferably of 0 to 80°C, more preferably at room temperature or under cooling with ice. A second process for preparing a functional polymer of the invention comprises (2-a) adding a compound of formula II as defined above to an alkenoyl isocyanate of formula I as defined above; and (2-b) polymerising the resulting novel intermediates as defined above and, optionally, one or more other polymerisable monomers, the monomers containing at least 0.1% by weight of said intermediate. In step (2-a), the addition may be carried out by a per se conventional procedure. For instance, the alkenoyl isocyanate (I) is reacted with the functional group-containing compound (II) in an inert solvent at a temperature of -20 to 100°C, preferably of 0 to 80°C, more preferably at room temperature or under cooling with ice. In step (2-b), the polymerisation may be also carried out by a per se conventional procedure, particularly by solution polymerisation. For instance, a monomeric mixture comprising the intermediate, i.e. a functional group-introduced isocyanatocarbonyl group-containing compound and, optionally, one or more polymerisable monomers in an inert solvent, preferably comprising a polymerisation initiator, is maintained at a temperature of 20 to 200°C, favourably of 60 to 150°C, more favourably of 80 to 120°C, for 0.5 to 5 hours. If used, the amount of the polymerisation initiator may be from 0.1 to 10% by weight, preferably from 0.5 to 5% by weight, based on the total weight of the monomers. When desired, a chain transfer agent may be also present in the reaction system. The amount of the chain transfer agent is usually from 5 to 20% by weight based on the total weight of the monomers. The starting alkenoyl isocyanate (I) can be produced by reacting an alkenylamide of the formula CH₂=CR-CONH₂ (III) wherein R is as defined above and an oxalyl halide of the formula (COX)₂ (IV) wherein X is halogen, optionally followed by dehydrohalogenation of the haloalkanoyl isocyanate by-product of the formula CH₂X-CHR-CO-NCO (V) wherein R and X are each as defined above. More advantageously, the alkenoyl isocyanate (I) can be produced by reacting the alkenylamide (III) with the oxalyl halide (IV) to produce an alkenyloxazolinedione hydrohalide of the formula: wherein X is a halogen atom (e.g. chlorine, bromine) and subjecting the latter to decomposition. For production of the alkenyloxazolinedione hydrohalide (VI), it is preferred that the oxalyl halide (IV) is first charged into a reactor and then the alkenylamide (III) is portionwise added thereto, whereby the reaction proceeds. The molar ratio of the alkenylamide (III) and the oxalyl halide (IV) may be usually about 1 : 1 - 3, preferably about 1 : 1 - 1.5. The use of an inert solvent as the reaction medium is not essential but is usually preferred. Thus, either one or both of the alkenylamide (III) and the oxalyl halide (IV) may be previously dissolved or suspended therein. The reaction temperature is normally higher than -50°C and lower than the decomposition temperature of the alkenyloxazolinedione hydrohalide (VI), preferably from about 0 to 40°C. From the industrial viewpoint, the temperature around boom temperature or under ice cooling is favorable. For separation of the alkenyloxazolinedione hydrohalide (VI) from the reaction mixture, there may be adopted any per se conventional separation procedure such as filtration or distillation under reduced pressure. Addition of seed crystals of the alkenyloxazolinedione hydrohalide (VI) to the reaction mixture may be sometimes favorable to accelerate the precipitation of the alkenyloxazolinedione hydrohalide (VI). However, separation of the alkenyloxazolinedione hydrohalide (VI) from the reaction mixture is not necessarily required. The alkenyloxazolinedione hydrohalide (VI) is then subjected to decomposition under the condition affording the alkenoyl isocyanate (I) predominantly or suppressing by-production of the haloalkanoyl isocyanate (V). One typical example of such condition is to carry out the decomposition under an ordinary pressure (atmospheric or autogenic). Namely, the alkenyloxazolinedione hydrohalide (VI) as charged in a reactor is heated under an ordinary pressure until the decomposition proceeds sufficiently. When a reaction medium is used, the heat decomposition can take place at such a low temperature as about 40°C. In the absence of any reaction medium, heating up to the decomposition temperature of the 2-alkenyloxazolinedione hydrohalide (e.g. about 102 to 103°C in case of 2-isopropenyloxazoline-4,5-dione hydrochloride) is required. As the reaction medium, there may be used an inert solvent. Another example of the condition is to carry out the decomposition in the presence of a hydrogen halide-eliminating agent. Namely, decomposition of the alkenoyloxazoline hydrohalide (VI) in the presence of a hydrogen halide-eliminating agent at a temperature of -50 to 200°C, preferably from 0 to 150°C under an ordinary or reduced pressure gives predominantly the alkenoyl isocyanate (I). As the hydrogen halide-eliminating agent such as not having an active hydrogen atom or as being reacted with a hydrogen halide not to produce an active hydrogen atom is favorably used. Amines which are the most popular hydrogen halide-eliminating agents are hardly usable in the process of this invention. Specific examples of the preferred hydrogen halide-eliminating agent are metal complex compounds (e.g. (Ph₃P)₂Ru(CO)₃, (Ph₃P)₃Pt), metal halides (e.g. lithium chloride, titanium tetrachloride, aluminum chloride, cuprous chloride), synthetic zeolite (e.g. molecular sieve, microporous glass), etc. The hydrogen halide-eliminating agent is used normally in an amount of about 0.1 to 100 mol, preferably of about 0.1 to 10 mol to 1 mol of the alkenyloxazolinedione hydrohalide (VI). Any reaction medium is not necessarily required to use. When used, an inert solvent may be employed. Another example of the conditition is to carry out the decomposition in the presence of a liquid medium having a dielectric constant of not more than 4. Such liquid medium may be constituted with one or more of inert solvents chosen from aliphatic or alicyclic hydrocarbons (e.g. pentane, hexane, heptane, octane, decalin, cyclohexane), aromatic hydrocarbons (e.g. benzene, toluene, xylene, naphthalene), ethers (e.g. propyl ether, butyl ether, dioxane, isopropyl ether), esters, halogenated hydrocarbons (e.g. carbon tetrachloride), etc. A dielectric constant of not more than 4 may be attained by the use of a single solvent or by the use of two or more solvents in combination. The decomposition may be carried out by keeping the alkenyloxazolinedione hydrohalide (VI) in a liquid medium of not more than 4 in dielectric constant at a temperature higher than the decomposition temperature of the alkenyloxazolinedione hydrohalide (VI), usually from about 40 to 150°C, preferably from about 60 to 120°C, whereby the alkenoyl isocyanate (I) is predominantly produced. Recovery of the alkenoyl isocyanate (I) from the reaction mixture may be accomplished by a per se conventional separation procedure such as distillation under atmospheric or reduced pressure. In any of the above reactions and the post-treatments, a small amount of a polymerization inhibitor may be incorporated into the reaction system or the reaction mixture for prevention of the unnecessary polymerization on the double bond. Examples of the polymerization inhibitor are hydroquinone, p-methoxyphenol, 2,6-di-t-butyl-4-methylphenol, 4-t-butylcatechol, bisdihydroxybenzylbenzene, 2,2'-methylene-bis(6-t-butyl-3-methylphenol), 4,4'-butylidene-bis(6-t-butyl-3-methylphenol), 4,4'-thiobis(6-t-butyl-3-methylphenol), p-nitrosophenol, diisopropylxanthogenesulfide, N-nitrosophenylhydroxylamine ammonium salt, 1,1-diphenyl-2-picrylhydrazil, 1,3,5-triphenylpheldazyl, 2,6-di-t-butyl-alpha-(3,5-di-t-butyl-4-oxo-2,5-cyclohexadien-1-ylidene)-p-trioxy, 2,2,6,6-tetramethyl-4-piperidone-1-oxil, dithiobenzoyl sulfide, p,p'-ditolyl trisulfide, p,p'-ditolyl tetrasulfide, dibenzyl tetrasulfide, and tetraethylthiuram disulfide. The alkenoyl isocyanates (I) are, in general, obtained in the form of a liquid which is stable at room temperature. They can therefore be handled with ease. They are soluble in various organic solvents can be used in solution form. The other polymerisable monomers usable in step (1-a) of the first process are those having no active hydrogen atom, while those usable in step (2-b) of the second process may be chosen from polymerisable monomers having no active hydrogen atom and polymerisable monomers having an active hydrogen atom. Examples of other polymerisable mononers are monoolefinic or diolefinic hydrocarbons (e.g. styrene, α-methylstyrene, α-ethylstyrene, 2-methyl-1-propene, 2-methyl-1-butene, 2-methyl-1-pentene, 2,3-dimethyl-1-butene, 2,3-dimethyl-1-pentene, 2,4-dimethyl-1-pentene, 2,3,3-trimethyl-1-heptene, 2,3-dimethyl-1-hexene, 2,4-dimethyl-1-hexene, 2,5-dimethyl-1-hexene, 2-methyl-3-ethyl-1-pentene, 2,3,3-trimethyl-1-pentene, 2,3,4-trimethyl-1-pentene, 2-methyl-1-octene, 2,6-dimethyl-1-heptene, 2,6-dimethyl-1-octene, 2,3-dimethyl-1-decene, 2-methyl-1-nonadecene, ethylene, propylene, butylene, amylene, hexylene, 1,3-butadiene, isoprene), monoolefinic or diolefinic halogenated hydrocarbons (e.g. α-chlorostyrene, α-bromostyrene, 2,5-dichlorostyrene, 2,5-dibromostyrene, 2,6-dichlorostyrene, 3,4-dichlorostyrene, o-, m- or p-fluorostyrene, 2,6-difluorostyrene, 3-fluoro-4-chlorostyrene, 3-chloro-4-fluorostyrene, 2,4,5-trichlorostyrene, dichloromonofluorostyrene, 2-chloropropene, 2-chlorobutene, 2-chloropentene, 2-chlorohexene, 2-chloroheptene, 2-bromobutene, 2-bromoheptene, 2-fluorohexene, 2-fluorobutene, 2-iodopropene, 2-iodopentene, 4-bromoheptene, 4-chloroheptene, 4-fluoroheptene, cis- and trans-1,2-dichloroethylene, 1,2-dibromoethylene, 1,2-difluoroethylene, 1,2-diiodoethylene, vinyl chloride, vinylidene chloride, bromoethylene, fluoroethylene, iodoethylene, 1,1-dibromoethylene, 1,1-difluoroethylene, 1,1-diiodoethylene, 1,1,2-trifluoroethylene, chlorobutadiene), carboxylic alkenyl esters (e.g. vinyl acetates, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl valerate, vinyl caproate, vinyl enantate, vinyl benzoate, vinyl p-chlorobenzoate, vinyl o-chlorobenzoate, vinyl p-methoxybenzoate, vinyl p-ethoxybenzoate, isopropenyl acetate, isopropenyl propionate, isopropenyl butyrate, isopropenyl isobutyrate, isopropenyl valerate, isopropenyl caproate, isopropenyl enanteate, isopropenyl benzoate, isopropenyl p-chlorobenzoate, isopropenyl o-chlorobenzoate, isopropenyl o-bromobenzoate, isopropenyl m-chlorobenzoate, isopropenyl alpha-chloroacetate, isopropenyl alpha-bromopropionate, vinyl alpha-chloroacetate, vinyl alpha-bromoacetate, vinyl alpha-chloropropionate, vinyl alpha-bromopropionate, vinyl alpha-iodopropionate, vinyl alpha-chlorobutyrate, vinyl alpha-chlorovalerate, vinyl alpha-bromovalerate), alkyl alkenoates (e.g. methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, sec-butyl acrylate, t-butyl acrylate, isobutyl acrylate, n-hexyl acrylate, 2-ethylhexyl acrylate, 3,5,5-trimethylhexyl acrylate, n-octyl acrylate, lauryl acrylate, tridecyl acrylate, stearyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, t-butyl methacrylate, isobutyl methacrylate, amyl methacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, lauryl methacrylate, tridecyl methacrylate, stearyl methacrylate, methyl crotonate), alkyl substituted alkenoates (e.g. methyl alpha-chloroacrylate, methyl alpha-bromoacrylate, methyl alpha-fluoroacrylate, methyl alpha-iodoacrylate, ethyl alpha-chloroacrylate, propyl alpha-chloroacrylate, isopropyl alpha-bromoacrylate, amyl alpha-chloroacrylate, decyl alpha-chloroacrylate, methyl alpha-cyanoacrylate, ethyl alpha-cyanoacrylate, amyl alpha-cyanoacrylate, decyl alpha-cyanoacrylate), allyl or methallyl compounds (e.g. allyl chloride, allyl cyanide, allyl bromide, allyl fluoride, allyl iodide, allyl chloride carbonate, allyl nitrate, allyl thiocyanate, allyl formate, allyl acetate, allyl propionate, allyl valerate, allyl caproate, allyl 3,5,5-trimethylhexoate, allyl benzoate, allyl acrylate, allyl crotonate, allyl oleate, allyl chloroacetate, allyl trichloroacetate, allyl chloropropionate, allyl chlorovalerate, allyl lactate, allyl pyruvate, allyl aminoacetate, allyl acetoacetate, allyl thioacetate, methallyl chloride, methallyl cyanide, methallyl chloride carbonate, methallyl nitrate, methallyl thiocyanate, methallyl formate, methallyl acetate, methallyl propionate, methallyl valerate, methallyl caproate, methallyl benzoate, allyl acrylate, allyl crotonate, allyl oleate, methallyl chloroacetate, methallyl trichloroacetate, methallyl chloropropionate, methallyl chlorovalerate, methallyl pyruvate, methallyl acetoacetate, methallyl thioacetate), dialkylaminoalkyl alkanoates (e.g. N,N'-dimethylaminoethyl acrylate, N,N'-dimethylaminoethyl methacrylate), isocyanatoalkyl alkanoates (e.g. isocyanatomethyl acrylate, isocyanatoethyl acrylate, isocyanatomethyl methacrylate, isocyanatoethyl methacrylate), glycidyl acrylate, glycidyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, benzyl acrylate, benzyl methacrylate, dialkyl unsaturated carboxylates (e.g. dimethyl maleate, diethyl maleate, dimethyl fumarate, diethyl fumarate, dibutyl fumarate), unsaturated nitriles (e.g. acrylonitrile, methacrylonitrile, ethacrylonitrile, 3-octenenitrile, and crotonitrile, oleonitrile). Examples of the polymerizable monomer having an active hydrogen atom are unsaturated carboxylic acids (e.g. acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, 2-isopropylacrylic acid, alpha-chloroacrylic acid), monoesters of alkyleneglycols with unsaturated carboxylic acids (e.g. ethylene glycol monoacrylate, propylene glycol monoacrylate, ethylene glycol monomethacrylate, ethylene glycol monocrotonate), unsaturated alcohols (e.g. crotyl alcohol, cinnamyl alcohol), unsaturated amides (e.g. acrylamide, methacrylamide, crotonamide, cinnamamide, p-benzamidostyrene), acrylic acid 2-sulfoethyl, methacrylic acid 2-sulfoethyl, t-butylacrylamidosulfonic acid, acrylic acid 4-sulfophenyl, p-vinylbenzenesulfonic acid, 2-methacryloxyethyl acid phosphate, 3-chloro-2-acid phosphoxypropyl methacrylate, vinyl phosphate, isopropenyl phosphate, unsaturated amines (e.g. allylamine, o-aminostyrene, methacrylic acid t-butylaminoethyl, and 7-amino-3,7-dimethyloctyl acrylate). Likewise, the inert solvent usable in the steps (1-a) and (1-b) of the first process and in the step (2-a) of the second process is to be chosen from the ones having no active hydrogen atom, while the inert solvent usable in the step (2-b) of the second process may be chosen from the ones having no active hydrogen atom and the ones having an active hydrogen atom. Examples of the inert solvent having no active hydrogen atom are aliphatic hydrocarbons (e.g. pentane, hexane, heptane), aromatic hydrocarbons (e.g. benzene, toluene, xylene), alicyclic hydrocarbons (e.g. cyclohexane, methylcyclohexane, decalin), petrolic hydrocarbons (e.g. petroleum ether, petroleum benzin), halogenated hydrocarbons (e.g. carbon tetrachloride, chloroform, 1,2-dichloroethane), ethers (e.g. diethyl ether, diisopropyl ether, anisole, dioxane, tetrahydrofuran), esters (e.g. methyl acetate, ethyl acetate, butyl acetate), ketones (e.g. acetone, methylethylketone, methylisobutylketone, cyclohexanone, acetophenone, isophorone), acetonitrile, dimethylformamide, and dimethylsulfoxide. As the polymerisation initiator usable in the step (1-a) of the first process and in the step (2-b) of the second process, there are exemplified organic peroxides (e.g. benzoyl peroxide, t-butyl perbenzoate, t-butyl peroxide, cumene hydroperoxide, di-t-butyl peroxide, t-butyl peroctoate), azo compounds (e.g. 2,2'-azobisisobutyronitrile, dimethyl azodiisobutyrate, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile). As the chain transfer agent, there may be used any conventional one having no active hydrogen atom. Specific examples include alpha-methylstyrene dimer. The isocyanatocarbonyl group-containing polymer as obtained in the step (1-a) of the first process has usually an isocyanatocarbonyl group content of 0.1 to 72.2% by weight and a molecular weight of 1,000 to 100,000. Examples of the compound (II) are melamine and its modified or related derivatives such as melamine, methylolated melamines (e.g. monomethylolmelamine, dimethylolmelamine, trimethylolmelamine, tetramethylolmelamine, pentamethylolmelamine, hexamethylolmelamine), alkanol-modified methylolated melamines (e.g. methoxymethylolmelamine, ethoxymethylolmelamine, propoxymethylolmelamine), and guanamine and its modified or related derivatives (e.g. homoguanamine, acetoguanamine, benzoguanamine, phenylacetoguanamine, methoxyguanamine). The functional polymer has physical characteristics attributed to the melamine group and to the carbonyliminocarbonyl linkage. Namely, the functional polymer has good cross-linkability and high rigidity due to the melamine group and good toughness and high adhesion due to the carbonyliminocarbonyl linkage. Besides, it will serve to improve storage stability and suppress self-condensation. Accordingly, the functional polymer is useful as a resinous material for coating compositions, engineering plastics and elastomers. It may be noted that some of the description herein, e.g. lists of exemplifying materials, may also be found in EP-A-0202840, EP-A-0204497 and EP-A-0206554. In particular, alkenyl isocyanates (I) and oxazolinedione hydrohalides (VI), and the conversion of the latter to the former, are described in EP-A-0202840. A synthesis of 2-vinyloxazoline-4,5-dione hydrochloride is given in Example 1 of EP-A-0202840, a synthesis of 2-isopropenyloxazoline-4,5-dione hydrochloride is given in its Example 2, syntheses of methacryloyl isocyanate from and via 2-isopropenyloxazoline-4,5-dione hydrochloride are given respectively in its Examples 8 and 19, and a synthesis of acryloyl isocyanate from 2-vinyloxazoline-4,5-dione hydrochloride is given in its Example 11. The following Example illustrates the invention. Amounts are given in parts by weight. Example 1) Preparation of butylated melamine/methacryloyl isocyanate adduct: Into a reaction vessel purged with nitrogen gas, butylated melamine was dissolved in chloroform, and a solution of methacrylol isocyanate in 1,2-dichloroethane was dropwise added thereto while stirring in nitrogen stream. After completion of the dropwise addition, chloroform and 1,2-dichloroethane were removed by distillation under reduced pressure to give butylated melamine/methacryloyl isocyanate adduct, as a colorless oil. M.w. 1,160 (GPC), viscosity 23,000 cp. 2) Preparation of an aminotriazine group-containing polymer:- A mixture of methyl methacrylate (20 parts), n-butyl acrylate (15 parts), butylated melamine/methacryloyl isocyanate adduct (15 parts) and 2,2'-azobis(2,4-dimethylvaleronitrile) (1.25 parts) was dropwise added to xylene (125 parts) heated at 100 to 105°C in 2.0 hours. After the dropwise addition was completed, stirring was continued at the same temperature for 4 hours, followed by cooling with water to produce an aminotriazine group-containing polymer. Molecular weight (determined by gel permeation chromatography), 3,470. Non-volatile content, 24.1 %.

Claims: A functional polymer having a molecular weight of 1,000 to 100,000 and comprising a main chain of carbon-carbon bonds and 0.1 to 99.9% by weight of one or more pendant functional groups of the formula -CO-NH-CO-Rm wherein Rm is a melamine group. A polymer according to claim 1, which comprises repeating units of the formula -CH₂-C(R)(-CO-NH-CO-Rm)-wherein Rm is as defined in claim 1 and R is H or C₁₋₅ alkyl. A process for preparing a polymer according to claim 2, which comprises polymerising a corresponding alkenoyl isocyanate of the formula CH₂=CR-CO-NCO and, optionally, one or more other polymerisable monomers having no active hydrogen atom, the monomers containing at least 0.1% by weight of the alkenoyl isocyanate; and reacting the resultant polymer with a corresponding active hydrogen atom-containing compound of the formula Rm-H wherein R m is as defined in claim 1 and R is as defined in claim 2. A process for preparing a polymer according to claim 2, which comprises adding an active hydrogen atom-containing compound as defined in claim 3 to an alkenoyl isocyanate as defined in claim 3; and polymerising the resulting compound of the formula CH₂=CR-CO-NH-CO-Rm and, optionally, one or more other polymerisable monomers, the monomers containing at least 0.1% by weight of said resulting compound wherein R m is as defined in claim 1 and R is as defined in claim 2.

Inventors: AOKI KEI, ITO TAKEYASU, MIZUGUCHI RYUZO, SUZUKI YUJI, URANO SATOSHI, AOKI, KEI, ITO, TAKEYASU, MIZUGUCHI, RYUZO, SUZUKI, YUJI, URANO, SATOSHI
Applicants: NIPPON PAINT CO LTD, NIPPON PAINT CO., LTD.
Application year: 1986
Main classification: C08F246
IPC codes: C07D303, C07D277, C07D207, C07D203, C07D295, C07D451, C07D493, C07D223, C07D251, C07J41, C07C275