Recyclable poly(urea-urethane) polymer and composite with dynamic hindered urea bonds (hubs)

A poly(urea-urethane) polymer obtained by a process comprising:

• reacting the following components
• (i) at least one isocyanate;
• (ii) at least one polyol;
• and
• (iii) at least one secondary amine having the following formula (I)
• wherein —Ra— is selected from the group consisting of —Z1—, —Z2—, —Z3—, —Z4—, —Z5—, —Z6—, —Z7—, —Z7—, —Z8—, —Z9—, —Z10—, —Z11—, —Z13—, —Z1—Z5—, —Z5—Z1—Z5—, —Z1—Z6—, —Z1—Z7—, —Z1—Z8—, —Z1—Z9—, —Z9—Z1—Z9—, —Z1—Z10—, —Z3—Z5—, —Z3—Z6—, —Z3—Z7—, —Z3—Z8—, —Z3—Z9—, —Z3—Z10—, —Z1—Z5—Z1—, —Z1—Z9—Z1—, —Z9—Z1(—Z11—Z1)n—Z9—, with n=1, 2, 3, 4, 5, or 6, and —Z1—Z12—Z1—;
• wherein
• —Z1— is a substituted or unsubstituted, linear or branched C1-C30 alkylene;
• —Z2— is a substituted or unsubstituted, linear or branched 2- to 300,000-membered heteroalkylene;
• —Z3— is a substituted or unsubstituted, linear or branched C2-C30 alkenylene;
• —Z4— is a substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenylene;
• —Z5— is a substituted or unsubstituted C5-C30 cycloalkylene;
• —Z6— is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;
• —Z7— is a substituted or unsubstituted C5-C30 cycloalkenylene;
• —Z8— is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylen;
• —Z9— is a substituted or unsubstituted C6-C30 arylene;
• —Z10— is a substituted or unsubstituted 5- to 30-membered heteroarylene;
• —Z11— is a C6-C30 arylene substituted with —NHR or —OR, wherein R is selected from the group consisting of H and substituted or unsubstituted, linear or branched C1-C10 alkyl;
• —Z12— is —N(Rf)—;
• —Z13— is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, wherein at least one of the one or more heteroatoms of Z13 is from Xa;
• wherein Ca is a C atom or a H atom and Cb is a C atom or a H atom, wherein at least one of Ca and Cb is a C atom;
• wherein Xa is a O atom or NH and Xb is a O atom or NH, wherein at least one of Xa and Xb is NH, with the condition that for Xa or Xb being NH, the respective Ca or Cb is/are C atom(s);
• wherein
• (A) Rc, Rd, Rf and Rg independently of each other are selected from the group consisting of hydrogen, linear or branched, substituted or unsubstituted C1-C30 alkyl, linear or branched, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C10 alkylene C5-C30 cycloalkyl, substituted or unsubstituted C1-C10 alkylene C5-C30 cycloalkenyl, substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C10 alkylene C6-C30 aryl and substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heteroaryl,
• Rb and Re independently of each other are defined as Rc, Ra, Rf and Rg;
• or
• Rb and Re are none, and Ca and Cb are connected to each other via a single bond forming a heterocycle consisting of Ca, Cb, Xa, Xb and Ra, or
• (B) Ca and Re form a substituted or unsubstituted C6-C30 arylene, and both Rf and Rg are none;
• and
• Cb and Rb form a substituted or unsubstituted C6-C30 arylene, and both Rc and Rd are none;
• or
• (C) —Ca and Re form a substituted or unsubstituted C6-C30 arylene, and both Rf and Rg are none;
• or
• —Cb and Rb form a substituted or unsubstituted C6-C30 arylene, and both Rc and Rd are none;
• wherein, when Ca and Re form a substituted or unsubstituted C6-C30 arylene, Rb, Rc and Ra independently of each other are defined as any one of Rc, Rd, Rf and Rg under (A);
• wherein, when Cb and Rb form a substituted or unsubstituted C6-C30 arylene, Re, Rf and Rg independently of each other are defined as any one of Rc, Ra, Rf and Rg under (A).

A poly(urea-urethane) polymer-based composite obtained by a process comprising

• reacting the following components
• (i) at least one isocyanate;
• (ii) at least one polyol;
• and
• (iii) at least one secondary amine having the following formula (I)
• wherein —Ra— is selected from the group consisting of —Z1—, —Z2—, —Z3—, —Z4—, —Z5—, —Z6—, —Z7—, —Z7—, —Z8—, —Z9—, —Z10—, —Z11—, —Z13—, —Z1—Z5—, —Z5—Z1—Z5—, —Z1—Z6—, —Z1—Z7—, —Z1—Z8—, —Z1—Z9—, —Z9—Z1—Z9—, —Z1—Z10—, —Z3—Z5—, —Z3—Z6—, —Z3—Z7—, —Z3—Z8—, —Z3—Z9—, —Z3—Z10—, —Z1—Z5—Z1—, —Z1—Z9—Z1—, —Z9—Z1(—Z11—Z1)n—Z9—, with n=1, 2, 3, 4, 5, or 6, and —Z1—Z12—Z1—;
• wherein
• —Z1— is a substituted or unsubstituted, linear or branched C1-C30 alkylene;
• —Z2— is a substituted or unsubstituted, linear or branched 2- to 300,000-membered heteroalkylene;
• —Z3— is a substituted or unsubstituted, linear or branched C2-C30 alkenylene;
• —Z4— is a substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenylene;
• —Z5— is a substituted or unsubstituted C5-C30 cycloalkylene;
• —Z6— is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene;
• —Z7— is a substituted or unsubstituted C5-C30 cycloalkenylene;
• —Z8— is a substituted or unsubstituted 5- to 30-membered heterocycloalkenylen;
• —Z9— is a substituted or unsubstituted C6-C30 arylene;
• —Z10— is a substituted or unsubstituted 5- to 30-membered heteroarylene;
• —Z11— is a C6-C30 arylene substituted with —NHR or —OR, wherein R is selected from the group consisting of H and substituted or unsubstituted, linear or branched C1-C10 alkyl;
• —Z12— is —N(Rf)—;
• —Z13— is a substituted or unsubstituted 5- to 30-membered heterocycloalkylene, wherein at least one of the one or more heteroatoms of Z13 is from Xa;
• wherein Ca is a C atom or a H atom and Cb is a C atom or a H atom, wherein at least one of Ca and Cb is a C atom;
• wherein Xa is a O atom or NH and Xb is a O atom or NH, wherein at least one of Xa and Xb is NH, with the condition that for Xa and/or Xb being NH, the respective Ca and/or Cb is/are C atom(s);
• wherein
• (A) Rc, Rd, Rf and Rg independently of each other are selected from the group consisting of hydrogen, linear or branched, substituted or unsubstituted C1-C30 alkyl, linear or branched, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted, linear or branched 2- to 30-membered heteroalkyl, substituted or unsubstituted, linear or branched 3- to 30-membered heteroalkenyl, substituted or unsubstituted C5-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkenyl, substituted or unsubstituted 5- to 30-membered heterocycloalkyl, substituted or unsubstituted 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 5- to 30-membered heteroaryl, substituted or unsubstituted C1-C10 alkylene C5-C30 cycloalkyl, substituted or unsubstituted C1-C10 alkylene C5-C30 cycloalkenyl, substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heterocycloalkyl, substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heterocycloalkenyl, substituted or unsubstituted C1-C10 alkylene C6-C30 aryl and substituted or unsubstituted C1-C10 alkylene 5- to 30-membered heteroaryl,
• Rb and Re independently of each other are defined as Rc, Ra, Rf and Rg;
• or
• Rb and Re are none, and Ca and Cb are connected to each other via a single bond forming a heterocycle consisting of Ca, Cb, Xa, Xb and Ra;
• or
• (B) Ca and Re form a substituted or unsubstituted C6-C30 arylene, and both Rf and Rg are none;
• and
• Cb and Rb form a substituted or unsubstituted C6-C30 arylene, and both Rc and Rd are none;
• or
• (C) —Ca and Re form a substituted or unsubstituted C6-C30 arylene, and both Rf and Rg are none;
• or
• —Cb and Rb form a substituted or unsubstituted C6-C30 arylene, and both Rc and Rd are none;
• wherein, when Ca and Re form a substituted or unsubstituted C6-C30 arylene, Rb, Rc and Ra independently of each other are defined as any one of Rc, Rd, Rf and Rg under (A);
• wherein, when Cb and Rb form a substituted or unsubstituted C6-C30 arylene, Re, Rf and Rg independently of each other are defined as any one of Rc, Ra, Rf and Rg under (A),
• obtaining a mixture comprising a poly(urea-urethane) polymer,
• bringing in contact the obtained mixture with (iv):
• (iv) a filler, the filler being selected from the group consisting of glass fibers, carbon fibers, mineral fibers, textiles, metal meshs, metal fibers, metal rods, carbonates, wood, and a mixture of two or more thereof.