Method for stabilizing thermoplastic recyclates, stabilized plastic compositions, and molding compounds and molded parts produced therefrom

Patent metadata

Field	Value
Publication number	US-12398256-B2
Application number	US-202017441626-A
Country	US
Kind code	B2
Filing date	Mar 24, 2020
Priority date	Mar 26, 2019
Publication date	Aug 26, 2025
Grant date	Aug 26, 2025

Abstract

The invention relates to a method for stabilizing thermoplastic recyclates or previously damaged plastic materials against oxidative, thermal and/or actinic degradation. According to the claimed method, at least one substituted sugar, selected from the group consisting of at least one ester and/or ether of an alditol or cyclitol, at least one ester of a saccharic acid, at least one amide and/or substituted amine of an amine sugar, and mixtures and combinations thereof, as the stabilizing component is introduced in a thermoplastic recyclate and optionally additionally at least one primary antioxidant and/or at least one secondary antioxidant is introduced in a thermoplastic recyclate.

First claim

The invention claimed is:

1. A method for stabilization of a thermoplastic plastic recyclate against oxidative, thermal, and/or actinic degradation, comprising
introducing component (A) into the thermoplastic plastic recyclate, wherein the component (A) is at least one substituted sugar selected from the group consisting of an ester of an alditol having at least four carbon atoms, an ether of an alditol having at least four carbon atoms, an ester of a cyclitol, an ether of a cyclitol, an ester of a saccharic acid, an amide of an amino sugar, and a substituted amine of an amino sugar.

2. The method in accordance with claim 1 , wherein the at least one substituted sugar comprises at least three free OH groups.

3. The method in accordance with claim 1 , wherein the at least one substituted sugar is mono- or di-substituted.

4. The method in accordance with claim 1 , wherein the alditol from which the ester or ether is formed has the molecular formula
HOCH 2 [CH(OH)] n CH 2 OH,
R 1 —OCH 2 [CH(OH)] n CH 2 OH, or

HOCH 2 [CH(OH)] n [CH(OR 1 )]CH 2 OH
where n=2-6, where R 1 is an optionally substituted sugar residue.

5. The method in accordance with claim 1 , wherein the alditol from which the ester or ether is formed is selected from the group consisting of threitol, erythritol, galactinol, mannitol, ribitol, sorbitol, xylitol, arabitol, ismaltol, lactitol, maltitol, maltotritol, hydrated oligosaccharides, and polysaccharides with polyol end groups.

6. The method in accordance with claim 1 , wherein the cyclitol from which the ester or ether is formed is selected from the group consisting of inositol, quercitol, viscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, ciceritol, quebrachitol, quinic acid, shikimic acid, and valienol.

7. The method in accordance with claim 1 , wherein the saccharic acid from which the ester or ether is formed is selected from the group consisting of aldonic acids and aldaric acids.

8. The method in accordance with claim 1 , wherein the saccharic amine from which the ester or ether is formed is selected from the group consisting of 1-amino-1-deoxyalditols and alpha-omega-diamino-alpha-omega-dideoxyalditols.

9. The method in accordance with claim 1 , wherein the at least one substituted sugar is selected from the group consisting of the following compounds:

where n is the same or different on every occurrence and is an integer between 1 and 100.

10. The method in accordance with claim 1 , wherein 0.01 to 5.0 parts by weight of the at least one substituted sugar (component (A)) is introduced into 95.0 to 99.99 parts of the thermoplastic plastic recyclate.

11. The method in accordance with claim 1 , wherein, in addition to the at least one substituted sugar, at least one primary antioxidant and/or at least one secondary antioxidant (component (B)) is/are introduced into the thermoplastic plastic recyclate.

12. The method in accordance with claim 11 , wherein the at least one primary antioxidant is selected from the group consisting of phenolic antioxidants, amines, and lactones.

13. The method in accordance with claim 11 , wherein the at least one secondary antioxidant is selected from the group consisting of phosphorus compounds and organo-sulfur compounds.

14. The method in accordance with claim 11 , wherein at least one primary antioxidant and at least one secondary antioxidant are introduced into the thermoplastic plastic recyclate.

15. The method in accordance with claim 11 , wherein component (A) and component (B) are introduced into the thermoplastic recyclate in a weight ratio of 95:5 to 5:95.

16. The method in accordance with claim 11 , wherein component (A) and/or component (B) are introduced by
mixing the component (A) and/or component (B) present as solids with the thermoplastic plastic recyclate present as a solid, melting the mixture thereby produced, and subsequent cooling; or
melting the component (A) and component (B) present as solids and introducing the melt thus produced into a melt of the thermoplastic plastic recyclate.

17. The method in accordance with claim 11 , wherein, with respect to 91 to 99.94 parts by weight of the thermoplastic plastic recyclate,
(A) 0.02 to 3 parts by weight of at least one substituted sugar (component (A)); and
(b) 0.04 to 6 parts by weight of the at least one primary antioxidant and/or of at least one secondary antioxidant (component (B)) are introduced.

18. The method in accordance with claim 1 , wherein the thermoplastic plastic recyclate contains one or more of a) to n), which are as follows:
a) recycled polymers of olefins and/or diolefins,
b) recycled polystyrene, polymethyl styrene, polyvinyl naphthalene, styrene butadiene (SB), styrene butadiene styrene (SBS), styrene ethylene butylene styrene (SEBS), styrene ethylene propylene styrene, styrene isoprene, styrene isoprene styrene (SIS), styrene butadiene acrylonitrile (ABS), styrene acrylonitrile acrylate (ASA), styrene ethylene, styrene maleic acid anhydride polymers, graft copolymers of styrene on butadiene, maleic acid anhydride on SBS or SEBS, and graft copolymers of methyl methacrylate, styrene butadiene, and/or ABS,
c) recycled polymers of unsaturated esters,
d) recycled polymers of unsaturated alcohols and/or derivatives,
e) recycled polyacetates and/or corresponding copolymers,
f) recycled polyphenylene oxides and/or blends with polystyrene or polyamides,
g) recycled polymers of cyclic ethers,
h) recycled polyurethanes of hydroxy terminated polyethers or polyesters and aromatic or aliphatic isocyanates,
i) recycled polyamides,
j) recycled polyamide imides, polyether imides, polyester imides, poly(ether)ketones, polysulfones, polyether sulfones, polyaryl sulfones, polyphenylene sulfides, polybenzimide azoles, and/or polyhydantoines,
k) recycled polyesters of aliphatic or aromatic dicarboxylic acids and diols or of hydroxy carboxylic acids,
l) recycled polycarbonates, polyester carbonates, and/or blends thereof,
m) recycled halogenated polymers, and
n) recycled cellulose derivatives.

19. The method in accordance with claim 18 , wherein the recycled polymers of olefins and diolefins are selected from the group consisting of polyethylene, polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, polycyclooctene, polyalkylene-carbon monoxide copolymers, EPM, EPDM, ethylene-vinyl acetate (EVA), ethylene-acrylic esters, ethylene-acrylic acid glycidyl acrylate, polypropylene-g-maleic acid anhydride, polypropylene-g-acrylic acid, and polyethylene-g-acrylic acid.

20. The method in accordance with claim 19 , wherein the polyethylene is selected from the group consisting of LDPE, LLDPE, VLDPE ULDPE, MDPE, HDPE, UHMWPE, and metallocene PE (m-PE).

21. A plastic composition comprising at least one substituted sugar and at least one thermoplastic recyclate,
wherein the at least one substituted sugar is selected from the group consisting of an ester of an alditol having at least four carbon atoms, an ether of an alditol having at least four carbon atoms, an ester of a cyclitol, an ether of a cyclitol, an ester of a saccharic acid, an amide of an amino sugar, and a substituted amine of an amino sugar.

22. The plastic composition in accordance with claim 21 , wherein the plastic composition

Assignees

• Fraunhofer Ges Forschung

Inventors

• Pfaendner Rudolf

Classifications

• C08K2201/014

  Additives containing two or more different additives of the same subgroup in C08K · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C08K5/151

  having one oxygen atom in the ring · CPC title

• C08K5/13

  Phenols; Phenolates · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title