Novel Amine Modifiers for Unsaturated Polyester Resins

Abstract

The results of studies are presented on the synthesis and functioning of amine modifiers for unsaturated polyester resins obtained by reacting ethylene oxide or propylene oxide with N,N ′‐diphenylethane‐1,2‐diamine and by reacting ethylene oxide with N,N ′‐diphenylhexane‐1,6‐diamine. When used in the amount of up to 2 wt.‐%, the amines substantially (several times) reduced the gelation time of modified unsaturated polyesters. The reactivity of resins was improved in expense of their stability.

The potential of unsaturated polyesters in biomedicine and tissue engineering: Synthesis, structure-properties relationships and additive manufacturing

“…As mentioned before, tertiary amines are widely used as accelerators, but often the formulations containing these compounds have a reduced shelf-life. A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs.…”

“…A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs. The amines were prepared from the reaction of ethylene oxide (EO) or propylene oxide (PO) with N,N'-diphenylethane-1,2-diamine or from the reaction of EO with N,N'-diphenylhexane-1,6-diamine (Fig.…”

The potential of unsaturated polyesters in biomedicine and tissue engineering: Synthesis, structure-properties relationships and additive manufacturing

“…As mentioned before, tertiary amines are widely used as accelerators, but often the formulations containing these compounds have a reduced shelf-life. A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs.…”

“…A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs. The amines were prepared from the reaction of ethylene oxide (EO) or propylene oxide (PO) with N,N'-diphenylethane-1,2-diamine or from the reaction of EO with N,N'-diphenylhexane-1,6-diamine (Fig.…”

Chemical Recycling of Poly(ethylene terephthalate)

“…However, it requires elevated temperatures (50–90 °C) in order to decompose the initiator molecule and form the primary radicals needed. If the curing must be carried out at ambient temperature, then a peroxide/amine system is used to form the primary free radicals 91. As such, we used benzoyl peroxide/ N,N ‐dimethyl‐ p ‐toluidine, which has been already studied for the free‐radical polymerization of MMA 92…”

Studies on activity of s-triazine ring containing amine modifiers in curing of unsaturated polyester resins

“…This is possible when the amine has two functional groups capable of reacting with carboxylic acids (or acid anhydrides) or with diols. The easiest solution is when amine contains hydroxyl groups [10][11][12][13]. Incorporation of such an amine into resin structure may significantly accelerate gelation of the resin because of formation of active RO • radicals that initiate polymerization [equation (1)] [14]:…”

“…The syntheses of 2-chloro-4,6-dimethoxy-1,3,5-triazine, 2,4-dichloro-6-methoxy-1,3,5-triazine as well as D, E and F modifiers were described in [20].…”

The potential of unsaturated polyesters in biomedicine and tissue engineering: Synthesis, structure-properties relationships and additive manufacturing

“…As mentioned before, tertiary amines are widely used as accelerators, but often the formulations containing these compounds have a reduced shelf-life. A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs.…”

“…A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs. The amines were prepared from the reaction of ethylene oxide (EO) or propylene oxide (PO) with N,N'-diphenylethane-1,2-diamine or from the reaction of EO with N,N'-diphenylhexane-1,6-diamine (Fig.…”

Chemical Recycling of Poly(ethylene terephthalate)

“…However, it requires elevated temperatures (50–90 °C) in order to decompose the initiator molecule and form the primary radicals needed. If the curing must be carried out at ambient temperature, then a peroxide/amine system is used to form the primary free radicals 91. As such, we used benzoyl peroxide/ N,N ‐dimethyl‐ p ‐toluidine, which has been already studied for the free‐radical polymerization of MMA 92…”

Studies on activity of s-triazine ring containing amine modifiers in curing of unsaturated polyester resins

“…This is possible when the amine has two functional groups capable of reacting with carboxylic acids (or acid anhydrides) or with diols. The easiest solution is when amine contains hydroxyl groups [10][11][12][13]. Incorporation of such an amine into resin structure may significantly accelerate gelation of the resin because of formation of active RO • radicals that initiate polymerization [equation (1)] [14]:…”

“…The syntheses of 2-chloro-4,6-dimethoxy-1,3,5-triazine, 2,4-dichloro-6-methoxy-1,3,5-triazine as well as D, E and F modifiers were described in [20].…”

The potential of unsaturated polyesters in biomedicine and tissue engineering: Synthesis, structure-properties relationships and additive manufacturing

“…As mentioned before, tertiary amines are widely used as accelerators, but often the formulations containing these compounds have a reduced shelf-life. A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs.…”

“…A possible strategy to overcome this issue is to incorporate the amine in the UP structure [56][57][58][59]. For such purpose, Duliban [56] developed novel amine modifiers with hydroxyl terminal groups to be incorporated in the UPs. The amines were prepared from the reaction of ethylene oxide (EO) or propylene oxide (PO) with N,N'-diphenylethane-1,2-diamine or from the reaction of EO with N,N'-diphenylhexane-1,6-diamine (Fig.…”

Chemical Recycling of Poly(ethylene terephthalate)

“…However, it requires elevated temperatures (50–90 °C) in order to decompose the initiator molecule and form the primary radicals needed. If the curing must be carried out at ambient temperature, then a peroxide/amine system is used to form the primary free radicals 91. As such, we used benzoyl peroxide/ N,N ‐dimethyl‐ p ‐toluidine, which has been already studied for the free‐radical polymerization of MMA 92…”

Studies on activity of s-triazine ring containing amine modifiers in curing of unsaturated polyester resins

“…This is possible when the amine has two functional groups capable of reacting with carboxylic acids (or acid anhydrides) or with diols. The easiest solution is when amine contains hydroxyl groups [10][11][12][13]. Incorporation of such an amine into resin structure may significantly accelerate gelation of the resin because of formation of active RO • radicals that initiate polymerization [equation (1)] [14]:…”

“…The syntheses of 2-chloro-4,6-dimethoxy-1,3,5-triazine, 2,4-dichloro-6-methoxy-1,3,5-triazine as well as D, E and F modifiers were described in [20].…”