Granted Patent B2

US 12,428,556 · App. 17/423,800 · Granted Sep 30, 2025

Inventors: Matthias Polidar (Darmstadt, DE); Elke Metzsch-Zilligen (Darmstadt, DE); Rudolf Pfaendner (Darmstadt, DE)

Assignee: Fraunhofer-Gesellschaft zur förderung der angewandten Forschung e.V.

C08L67/04C08K5/053C08K5/524C08K5/527C08L2201/06

Abstract

Claims (31)

1. A method of catalyzing hydrolysis of a condensation polymer comprising adding a mixture consisting of

(A) at least one polyol selected from the group comprising aliphatic or cycloaliphatic polyols and

(B) at least one organic phosphorus compound

to the condensation polymer to form a condensation polymer composition comprising said mixture and said condensation polymer and exposing said condensation polymer composition to water; wherein the condensation polymer composition is exposed to water only after the addition of the mixture consisting of components (A) and (B);

wherein said mixture thermally stabilizes the condensation polymer in the absence of water.

2. The method of claim 1 , wherein the condensation polymer is selected from the group consisting of polyesters of aliphatic or aromatic dicarboxylic acids and diols or of hydroxycarboxylic acids, polycarbonates, polyester carbonates, polyamides, semi aromatic polyamides, and mixtures, combinations, or blends of two or more of the above-named polymers.

3. The method of claim 1 , wherein the condensation polymer is selected from the group consisting of PLA, poly(butylene adipate) (PBA), polycaprolactone (PCL), poly-3-hydroxybutyrate, poly-4-hydroxybutyrate, poly-3-hydroxyvalerate, poly(hexamethylene succinate), poly(butylene succinate) and copolymers and mixtures or blends of two or more of the above-named polymers.

4. The method of claim 3 , wherein the condensation polymer is selected from the group consisting of PLA, PBA, and copolymers thereof.

5. The method of claim 4 , wherein the PLA copolymers are obtained by ring-opening polymerization of D-lactide and/or L-lactide with comonomers selected from hydroxycarboxylic acids, diols, and/or carboxylic acids.

6. The method of claim 1 , wherein the at least one aliphatic or cycloaliphatic polyol is selected from the group consisting of polyols having at least four OH groups.

7. The method of claim 1 , wherein the at least one organic phosphorus compound is selected from the group consisting of organic phosphites, organic phosphonites, organic phosphonates, and organic phosphates.

8. The method of claim 7 , wherein the organic phosphite is a hydrolyzable phosphite having the general formula I

wherein

(i) R 1 , R 2 and R 3 are selected independently of one another from the group consisting of optionally substituted C 4 -C 32 -alkyl-, cycloalkyl- and aryl residues, or

(ii) R 1 is selected from the group consisting of optionally substituted C 4 -C 32 -alkyl-, cycloalkyl- and aryl residues and R 2 is connected to R 3 to form a cyclic system.

9. The method of claim 7 , wherein the organic phosphite has one of the following formulas (II) or (III),

wherein R 1 is selected from optionally substituted C 4 -C 32 -alkyl-, -cycloalkyl-, and aryl residues.

10. The method of claim 7 , wherein the organic phosphite is selected from the following compounds

in which n=1-100,

or from the group consisting of trilauryl phosphite, triisodecylphosphite, tridecylphosphite, trihexadecylphosphite, trioctadecylphosphite, tribehenylphosphite, triarachidylphosphite, tricerylphosphite, tricetylphosphite, and trioleylphosphite.

11. The method of claim 7 , wherein the organic phosphite is free of a compound in accordance with formula (IV)

wherein R 20 and/or R 21 are, independently of one another on every occurrence, a hydrogen atom, a C 1-8 -alkyl group, a C 5-8 -cycloalkyl group, a C 6-12 -alkylcycloalkyl group, a C 7-12 -aralkyl group, or a phenyl group,

R 23 and R 24 are, independently of one another on every occurrence, a hydrogen atom, a C 1-8 -alkyl group, a C 5-8 -cycloalkyl group, a C 6-12 -alkylcycloalkyl group, a C 7-12 -aralkyl group, or a phenyl group,

R 22 is a hydrogen atom or an alkyl group on every occurrence,

L 5 is a single bond, a sulfur atom, or a bivalent group in accordance with the formula (IVa)

where R 25 signifies a hydrogen atom, a C 1-8 -alkyl group, or a C 5-8 -cycloalkyl group,

L 6 is a C 2-8 -alkylene group or a bivalent group in accordance with the formula (IVb)

where L 7 is a single bond or a C 1-8 -alkylene group and * represents an oxygen bonding site, and

one of Z 1 and Z 2 is a hydroxyl group, a C 1-8 -alkyl group, a C 1-8 -alkoxy group or a C 7-12 -aralkyloxy group, and the other is a hydrogen atom or a C 1-8 -alkyl group.

12. The method of claim 7 , wherein the organic phosphate is selected from the group consisting of trilauryl phosphate, triisodecyl phosphate, tridecyl phosphate, trihexadecyl phosphate, trioctadecyl phosphate, tribehenyl phosphate, triarachidyl phosphate, triceryl phosphate, tricetyl phosphate, trioleyl phosphate, diphosphates, polyphosphates, monostearyl phosphate, distearyl phosphate, and mixtures of a monoalkyl phosphate, of a dialkyl phosphate and of a trialkyl phosphate.

13. The method of claim 1 , wherein the weight ratio of component (A) to component (B) is from 1:10 to 10:1.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (102)