KR850007440A - Process for preparing reaction product of olefin unsaturated compound and active hydrogen containing compound - Google Patents

Abstract

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Description

Process for preparing reaction product of olefin unsaturated compound and active hydrogen containing compound

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Claims (23)

Compounds A) and B) are -AH-valent Or an organic having from 1 to 20 carbon atoms in a diazabicyclooctane (DABCO), a halide of a quaternary ammonium compound, or a compound with an alkyl silicate, amidine, alkyl radicals and / or aryl radicals when representing one of the -SH groups Phosphonium salt, general formula P (CH ₂ -Y) _3, wherein Y _S is the same or different and represents a radical —OH, CH ₂ CN or —N (Z) ₂ , wherein Z is an alkyl radical having 1 to 5 carbon atoms Tertiary phosphane, general formula P (R ⁴ , R ⁵ , R ⁶ ), wherein R ⁴ , R ⁵ and R ⁶ each represent at least one alkyl, alkoxy or di having from 1 to 4 carbon atoms in the alkyl radical Tertiary phosphanes of phenyl radicals unsubstituted or substituted with alkylamino groups or alkyl radicals having 1 to 12 carbon atoms and R ⁴ , R ⁵ and R ⁶ are the same or different but at least one of the radicals represents phenyl radicals; formula ^{(R 7, R 8, R} 9) P = NC (R 10, R 11, R | 12) [ W Standing R ^7, R ^8, and R ⁹ are the same or different at least one alkyl, alkoxy or di unsubstituted or substituted with an alkyl group a phenyl radical or an alkyl radical containing from 1 to 12 carbon atoms having 1 to 4 carbon atoms in each alkyl radical, R ¹⁰ , R ¹¹ and R ¹² are the same or different and each represent an alkyl radical having 1 to 5 carbon atoms or a phenyl radical] and reacted in the presence of at least one catalyst selected from the group comprising aminophosphorane and the like. At least two active H atoms or b) at least two active H atoms, characterized in that it forms a polymer and / or a polymer reaction product. Reaction with a group of formula (II) or c) a compound containing at least one active H atom and at least one group (II) or comprising a corresponding amount of group (II) How to make water. R ¹ R ² C = CR ³ -X (I) -AH- (II) Wherein X represents —CO— attached to an additional R ¹ R ² C═CR ³ group, either directly or via a radical of a polyhydric alcohol or of an amine, and R ¹ represents hydrogen or a hydrocarbon radical of 1 to 10 carbon atoms. , R ² represents hydrogen or a hydrocarbon radical of 1 to 10 carbon atoms, an ester group containing a R ⁴ radical of a monohydric alcohol of up to 12 carbon atoms, -CN, -NO ₂ or CO-NHR ¹ or CO-R ¹ group, R ³ is the same as or different from R ² as defined in R ^2, is -AH- One of-, -NH-, and -SH group is shown. -AH- Or -SH group, when reacted in the presence of at least one quaternary ammonium compound or alkali metal alcoholate to produce oligomers and / or polymer reaction products, characterized in that at least two of the following A) Compound containing group (I) a) at least two active H atoms or b) active H atoms or b) at least two groups of the following type (II) containing active H atoms or c) at least one activity A process for preparing a reaction product with an H atom and a compound B) containing at least one group of the following form (II) or forming a corresponding amount of such group (II). [A] A) Polyacrylate containing at least two free acrylic acid groups, reaction product of polyisocyanate and OH group containing acrylic acid ester or reaction product of epoxy resin and acrylic acid and B) diketene or hydroxyethyl acryl Reaction products of acetoacetic acid esters of late or methacrylate are excluded] R ¹ R ² C = CR ³ -X (I) -AH- (II) Wherein X, R ¹ , R ² , R ³ and -AH- are as defined in claim 1. The process of claim 1 wherein the catalyst used is fluoride or phosphane. The catalyst used according to claim 1 or 3, wherein the catalyst used is trishydroxymethylphosphane, trisdimethylaminomethylphosphane, tris-p-anisylphosphane, methyldiphenylphosphane, methyl di-p-anisylphosphane Or x, x-dimethylbenzeneimino-tributylphosphoran. The radical according to any one of claims 1 to 4, wherein the radical R ¹ R ² C = CR ³ -X (I) in compound A) is derived from acrylic acid, and compound B) contains a malonic acid residue attached by ester linkage. Way. The radical R ¹ R ² C═CR ³ -X (I) according to any one of claims 1 to 5, wherein X represents -CO- and R ³ represents hydrogen or alkyl having 1 to 8 carbons. A method of deriving from a monounsaturated or polyunsaturated carboxyl, acid preferably acrylic acid, methacrylic acid and / or maleic acid having the following basicity and containing 2 to 10, preferably 3 to 6 carbon atoms. Process according to any of the preceding claims, wherein the group (I) in compound A) is attached to a polyol or polyamine, preferably oligomers and / or polymer radicals. The method according to any one of claims 1 to 7, wherein the compound A) is derived from an OH group-containing polyester or an OH group-containing acrylic resin, an epoxide resin, an amine resin, or the like. The compound of any one of claims 1 to 8, wherein -AH- group (II) in compound B) When represented, the groups -CO-CHR ¹ -CO, NC-CHR ¹ -CO-, NC-CH ₂ -CN, = PO-CHR ¹ -CO-, = PO-CHR ¹ -CN, = PO-CHR ¹ Derived from compounds containing —PO or —CO—CHR ¹ —NO _2, etc., when it represents —NH—, derived from primary and / or secondary polyamids, and when it represents —SH— , Thioalcohol esters or amides and / or mercaptans. 10. The method of any one of claims 1 to 9, wherein compound B) is derived from at least a bifunctional compound in the group comprising polyols, polyamines and / or poly mercaptans. Process according to any of the preceding claims, wherein the product is present on the substrate, in particular on the metal, preferably in a thin layer. The process according to claim 1, wherein the reaction is carried out at a temperature of −10 to 180, preferably 0 to 100 ° C., optionally in the presence of a catalyst. A) a compound containing at least two groups (I) and a) at least two active H atoms or b) at least two groups of the following form (II) containing active H atoms or c) at least one activity A two-component lacquer combined with its own or with conventional additives containing H atoms and at least one group of the following form (II) or forming a corresponding amount of such group (II) R ¹ R ² C = CR ³ -X (Ⅰ) -AH- (II) Where X, R ¹ , R ² , R ³ and -AH- are as defined in claim 1. ※ Note: The disclosure is based on the initial application.