Latent combination compounds and latent ammonium salts comprising epoxide resin curing agents and flame-protection agents as well as epoxide resin systems and products prepared from them

Process for preparing a latent ammonium salt, wherein at least one latent combination compound according to formula I

• in which R1 equals a general radical R0,
• R0 being hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• R2 and R3, independently of each other, having the meaning given for R0, R2 and R3 being able to be linked accompanied by the formation of a cycle or several cycles,
• A being selected from the group consisting of OH and COX in which X is selected from the group consisting of OH, NH2, NHRa, NRbRc, and O−M+, with Ra to Rc independently of each other, having the meaning given for R0, and Rb and Rc being able to be linked accompanied by the formation of a cycle or several cycles and M+ being any metal ion, and
• Z denoting a divalent linear or branched, saturated or unsaturated hydrocarbon chain with 2 to 100 carbon atoms, which can optionally contain one or more cycles and can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen
• is reacted with at least one reagent which comprises water, resulting in the splitting of the P—N bond shown in formula I.

Process for preparing a latent ammonium salt, wherein at least one latent combination compound according to formula I

• in which R1 equals a general radical R0,
• R0 being hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• R2 and R3, independently of each other, having the meaning given for R0, R2 and R3 being able to be linked accompanied by the formation of a cycle or several cycles,
• Z denoting a divalent linear or branched, saturated or unsaturated hydrocarbon chain with 2 to 100 carbon atoms, which can optionally contain one or more cycles and can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• in which A equals COOH, is reacted with at least one reagent which comprises at least one compound selected from water, and mono- or polyhydric hydroxy compounds, resulting in the splitting of the P—N bond shown in formula I.

Process for preparing a latent combination compound or a latent ammonium salt, wherein at least one phosphorus-containing component (a) selected from

• i) derivatives of the intramolecular ester of 4-hydroxy-butane-1 phosphinic acid according to one of the ring-closed formulae X to XV
• in which R10 to R18, independently of each other, have the general meaning given for R0
• wherein R0 is hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen;
• and
• two or more of R10 to R17 being able to be linked accompanied by the formation of a cycle or several cycles, and
• ii) derivatives of phospholan according to one of the ring-closed formulae XXX and XXXI
• in which R30 to R34, independently of each ocher, have the general meaning given for R0 above and one or more of R30 to R33 are able to be linked accompanied by the formation of a cycle or several cycles,
• is reacted with a component (b) which comprises a nitrogen-containing compound which has no basic NH function, the process comprising the reaction with at least one component (c) selected from water and mono- or polyhydric hydroxy compounds.

Process for preparing a latent combination compound or a latent ammonium salt, wherein at least one phosphorus-containing component (a) selected from

• i) derivatives of the intramolecular ester of 4-hydroxy-butane-1 phosphinic acid according to one of the ring-closed formulae X to XV
• in which R10 to R18, independently of each other, have the general meaning given for R0,
• wherein R0 is hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen;
• and
• two or more of R10 to R17 being able to be linked accompanied by the formation of a cycle or several cycles, and
• ii) derivatives of phospholan according to one of the ring-closed formulae XXX and XXXI
• in which R30 to R34, independently of each other, have the general meaning given for R0 above and one or more of R30 to R33 can be linked accompanied by the formation of a cycle or several cycles,
• is reacted with a component (b) which comprises a nitrogen-containing compound which has at least one basic NH function.

Single-component epoxide resin system, comprising

• at least one epoxide resin component and at least one curing agent/accelerator component comprising the latent combination compounds according to formula I
• in which R1 equals a general radical R0,
• R0 being hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• R2 and R3, independently of each other, having the meaning given for R0, R2 and R3 being able to be linked accompanied by the formation of a cycle or several cycles,
• A being selected from the group consisting of OH and COX in which X is selected from the group consisting of OH, NH2, NHRa, NRbRc, and O−M+, Ra to Rc independently of each other, having the meaning given for R0, and Rb and Rc being able to be linked accompanied by the formation of a cycle or several cycles and M+ being any metal ion, and
• Z denoting a divalent linear or branched, saturated or unsaturated hydrocarbon chain with 2 to 100 carbon atoms, which can optionally contain one or more cycles and can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• as well as optionally further additives and modification agents.

Single-component epoxide resin adhesive, comprising

• at least one epoxide resin component and at least one curing agent/accelerator component comprising the latent combination compounds according to formula I
• in which R1 equals a general radical R0,
• R0 being hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• R2 and R3, independently of each other, having the meaning given for R0, R2 and R3 being able to be linked accompanied by the formation of a cycle or several cycles,
• A being selected from the group consisting of OH and COX in which X is selected from the group consisting of OH, NH2, NHRa, NRbRc, and O−M+, with Ra to Rc independently of each other, having the meaning given for R0, and Rb and Rc being able to be linked accompanied by the formation of a cycle or several cycles and M+ being any metal ion, and
• Z denoting a divalent linear or branched, saturated or unsaturated hydrocarbon chain with 2 to 100 carbon atoms, which can optionally contain one or more cycles and can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen,
• as well as optionally further additives and modification agents.

Process for preparing a latent combination compound or a latent ammonium salt, wherein at least one phosphorus-containing component (a) selected from

• i) derivatives of 4-hydroxy-butane-1 phosphinic acid according to one of the ring-open formulae XVI to XXI
• in which R10 to R18, independently of each other, have the general meaning given for R0,
• wherein R0 is hydrogen or a linear or branched, saturated or unsaturated hydrocarbon group with 1 to 100 carbon atoms, which can optionally contain one or more heteroatoms selected from the group consisting of oxygen, nitrogen, sulphur, phosphorus, silicon and halogen;
• and
• two or more of R10 to R17 being able to be linked accompanied by the formation of a cycle or several cycles, and
• ii) derivatives of phospholan according to one of the ring-open formulae XXXII and XXIII
• in which R30 to R34, independently of each other, have the general meaning given for R0 above, and one or more of R30 to R33 can be linked accompanied by the formation of a cycle or several cycles,
• is reacted with a component (b) which comprises a nitrogen-containing compound.