IP Library Granted Patent US 12,552,913
Granted Patent B2
US 12,552,913 · App. 17/625,387 · Granted Feb 17, 2026

Use of phenolically substituted sugar derivatives as stabilisers, plastic composition, method for stabilising plastics and phenolically substituted sugar derivatives

Inventor: Rudolf Pfaendner (Darmstadt, DE)
Assignee: Fraunhofer-Gesellschaft zur förderung der angewandten Forschung e.V.
C08K5/1345C08K5/005C08K5/103C08K5/20
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Quick Facts
Patent No.
US 12,552,913
App. No.
17/625,387
Granted
Feb 17, 2026
Kind
B2
Abstract

The present invention relates to the use of at least one phenolically substituted sugar derivative as a stabiliser of organic materials, in particular plastics, against oxidative, thermal and/or actinic degradation. The present invention also relates to a corresponding plastic composition, to a method for stabilising plastics, to a moulding compound or a moulded part as well as a phenolically substituted sugar derivative.

Claims (33)

1 . A method of stabilizing an organic material comprising incorporating into the organic material at least one phenolically substituted sugar derivative,

the phenolically substituted sugar derivative selected from the group consisting of the following molecules

and mixtures thereof,

[having a body derived from sugar, and at least one substituted according to general formula I

wherein

R 1 and R 2 are identical or different on each occurrence and are selected from the group consisting of hydrogen and linear or branched alkyl radicals, with the proviso that at least one residue R 1 or R 2 is not hydrogen,

X is an alkylene group having 1 to 18 carbon atoms or a chemical bond,

Y is a grouping selected from the following groupings

wherein X is bound to the terminus shown on the left of Y,

and where the body of the phenolically substituted sugar derivative derived from a sugar has at least 3 unsubstituted hydroxyl groups and/or the base body of the phenolically substituted sugar derivative derived from a sugar has at least 4 carbon atoms and has at least 2 unsubstituted hydroxy groups, and is at least one alditol, a cyclitol, a sugar acid or an amino sugar having at least 4 carbon atoms, and]

wherein the organic material is a polymer selected from the group consisting of

a) polymer made from olefins or diolefins, polyalkylene-carbon monoxide copolymers, and corresponding copolymers in the form of random or block structures ethylene-vinyl acetate (EVA), ethylene-acrylic esters, and corresponding graft polymers,

b) polystyrene, polymethylstyrene, polyvinylnaphthalene, 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 anhydride polymers including corresponding graft polymers, and graft copolymers made from methyl methacrylate, styrene-butadiene and ABS (MABS),

c) polymers of unsaturated esters, polyacrylonitrile, polyacrylamide, and corresponding copolymers,

d) polymers made from unsaturated alcohols and derivatives,

e) polyacetals and corresponding copolymers,

f) polyphenylene oxides and blends of these with polystyrene or polyamides

g) polymers of cyclic ethers,

h) polyurethanes made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates,

i) polyamides

j) polyimides, polyamide-imides, polyether imides, polyester imides,

poly(ether)ketones, polysulfones, polyether sulfones, polyaryl sulfones, polyphenylene sulfide, polybenzimidazoles, and polyhydantoins,

k) polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids,

l) polycarbonates, polyester carbonates and blends thereof,

m) cellulose derivatives,

n) and mixtures, combinations, or blends of two or more of the above-named polymers,

wherein said polymer or polymers can be fresh or recycled.

2 . The method according to claim 1 , wherein the at least one phenolically substituted sugar derivative is incorporated in a total amount of 0.01 to 10% by weight based on the organic material.

3 . The method according to claim 1 , wherein the at least one phenolic substituted sugar derivative is incorporated in combination with a primary and/or a secondary antioxidant that differs from the at least one phenolic substituted sugar derivative.

4 . The method according to claim 3 , wherein the at least one primary and/or secondary antioxidant is incorporated in a total amount, based on the total amount of the at least one phenolically substituted sugar derivative from 0.01 to 5 parts by weight.

5 . The method according to claim 3 , wherein, based on 91 to 99.94 parts by weight of the plastic material

(A) 0.02 to 3 parts by weight of the at least one phenolically substituted sugar derivative, and

(B) 0.04 to 6 parts by weight of the at least one primary antioxidant and/or of the at least one secondary antioxidant are incorporated.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2022
From: PFAENDNER, RUDOLF
To: FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E.V.
Reel/Frame 058759/0584 →
Priority Claims (1)
DE 10 2019 210 040 · Jul 8, 2019 · national
Continuity (1)
Related Publication 20220267568A1 · Aug 25, 2022
References Cited (157)
US 2682522A · Coover et al. · 1954 [cited by applicant]
US 2716101A · Coover, Jr. et al. · 1955 [cited by applicant]
US 2891915A · McCormack et al. · 1959 [cited by applicant]
US 3285855A · Dexter et al. · 1966 [cited by applicant]
US 3326852A · Thomas · 1967 [cited by applicant]
US 3442854A · Curtius et al. · 1969 [cited by applicant]
US 3919363A · Ura et al. · 1975 [cited by applicant]
US 3946093A · Koto et al. · 1976 [cited by applicant]
US 4328174A · Schmidt et al. · 1982 [cited by applicant]
US 4331614A · Schmidt et al. · 1982 [cited by applicant]
US 4374971A · Schmidt et al. · 1983 [cited by applicant]
US 4415719A · Schmidt et al. · 1983 [cited by applicant]
US 5216113A · Schulz-Schlitte et al. · 1993 [cited by applicant]
US 5334692A · Hess et al. · 1994 [cited by applicant]
US 6288210B1 · Shobja et al. · 2001 [cited by applicant]
US 6291630B1 · König et al. · 2001 [cited by applicant]
US 6861499B2 · Vinciguerra et al. · 2005 [cited by applicant]
US 7115765B2 · Sprenger et al. · 2006 [cited by applicant]
US 7816486B2 · Freitag et al. · 2010 [cited by applicant]
US 8058329B2 · Just et al. · 2011 [cited by applicant]
US 8349925B2 · Butz · 2013 [cited by applicant]
US 8853307B2 · Butz · 2014 [cited by applicant]
US 9441091B2 · Haruna et al. · 2016 [cited by applicant]
US 9951207B2 · Hoelzl et al. · 2018 [cited by applicant]
US 10138354B2 · Groos et al. · 2018 [cited by applicant]
US 10214631B2 · Pfaendner et al. · 2019 [cited by applicant]
US 10259931B2 · Hoelzl et al. · 2019 [cited by applicant]
US 10323136B2 · Pfaendner et al. · 2019 [cited by applicant]
US 10364340B2 · Pfaendner et al. · 2019 [cited by applicant]
US 10370537B2 · Pfaendner et al. · 2019 [cited by applicant]
US 10450442B2 · Pfaendner et al. · 2019 [cited by applicant]
US 10544284B2 · Pfaendner et al. · 2020 [cited by applicant]
US 10781296B2 · Groos et al. · 2020 [cited by applicant]
US 10913743B2 · Pfaendner et al. · 2021 [cited by applicant]
US 11292859B2 · Klein et al. · 2022 [cited by applicant]
US 11407720B2 · Fischer et al. · 2022 [cited by applicant]
US 11591450B2 · Pfaendner et al. · 2023 [cited by applicant]
US 11634560B2 · Ciesielski et al. · 2023 [cited by applicant]
US 11760865B2 · Pfaendner et al. · 2023 [cited by applicant]
US 20050020800A1 · Levchik et al. · 2005 [cited by applicant]
US 20050176983A1 · Sprenger et al. · 2005 [cited by applicant]
US 20070219295A1 · Levchik et al. · 2007 [cited by applicant]
US 20080045673A1 · Piotrowski et al. · 2008 [cited by applicant]
US 20080167405A1 · Just et al. · 2008 [cited by applicant]
US 20100016244A1 · Vachy · 2010 [cited by applicant]
US 20100280215A1 · Just et al. · 2010 [cited by applicant]
US 20110136748A1 · Vachy · 2011 [cited by applicant]
US 20110257310A1 · Butz · 2011 [cited by applicant]
US 20110275747A1 · Hacker · 2011 [cited by examiner]
US 20120296018A1 · Haruna et al. · 2012 [cited by applicant]
US 20140005289A1 · Butz · 2014 [cited by applicant]
US 20140128520A1 · Haruna et al. · 2014 [cited by applicant]
US 20160052927A1 · Pfaendner et al. · 2016 [cited by applicant]
US 20160272789A1 · Pfaendner et al. · 2016 [cited by applicant]
US 20170066905A1 · Hoelzl et al. · 2017 [cited by applicant]
US 20170107375A1 · Pfaendner et al. · 2017 [cited by applicant]
US 20170121499A1 · Pfaendner et al. · 2017 [cited by applicant]
US 20170260362A1 · Pfaendner et al. · 2017 [cited by applicant]
US 20170260363A1 · Pfaendner et al. · 2017 [cited by applicant]
US 20170260366A1 · Pfaendner et al. · 2017 [cited by applicant]
US 20170267835A1 · Groos et al. · 2017 [cited by applicant]
US 20180186970A1 · Groos et al. · 2018 [cited by applicant]
US 20180201760A1 · Hoelzl et al. · 2018 [cited by applicant]
US 20190248927A1 · Klein et al. · 2019 [cited by applicant]
US 20200231783A1 · Pfaendner et al. · 2020 [cited by applicant]
US 20200317886A1 · Pfaendner et al. · 2020 [cited by applicant]
US 20200361879A1 · Fischer et al. · 2020 [cited by applicant]
US 20210130582A1 · Ciesielski et al. · 2021 [cited by applicant]
US 20210388176A1 · Metzsch-Zilligen et al. · 2021 [cited by applicant]
US 20220073734A1 · Polidar et al. · 2022 [cited by applicant]
US 20220119624A1 · Pfaendner et al. · 2022 [cited by applicant]
US 20220162422A1 · Pfaendner · 2022 [cited by applicant]
US 20220267568A1 · Pfaendner · 2022 [cited by applicant]
US 20220340717A1 · Olschewski et al. · 2022 [cited by applicant]
US 20230117792A1 · Pfaendner et al. · 2023 [cited by applicant]
US 20230119120A1 · Pfaendner et al. · 2023 [cited by applicant]
US 20230174746A1 · Polidar et al. · 2023 [cited by applicant]
US 20230203274A1 · Polidar et al. · 2023 [cited by applicant]
US 20240026124A1 · Pfaendner · 2024 [cited by applicant]
US 20240043745A1 · Mayer et al. · 2024 [cited by applicant]
US 20240174840A1 · Pfaendner et al. · 2024 [cited by applicant]
CN 103554650A · 2014 [cited by applicant]
CN 105960432A · 2016 [cited by applicant]
CN 108409930A · 2018 [cited by applicant]
CN 109206670A · 2019 [cited by applicant]
CN 111040396A · 2020 [cited by examiner]
CN 111448250A · 2020 [cited by applicant]
DE 102007005863A1 · 2008 [cited by applicant]
DE 102007007644A1 · 2008 [cited by applicant]
DE 102017217312A1 · 2019 [cited by applicant]
EP 2450401A1 · 2012 [cited by applicant]
GB 1081789A · 1967 [cited by applicant]
JP S47034336A · 1972 [cited by applicant]
JP S48000939A · 1973 [cited by applicant]
JP S5214648A · 1977 [cited by applicant]
JP S534086B · 1978 [cited by applicant]
JP S5421378B1 · 1979 [cited by applicant]
JP 2000192066A · 2000 [cited by applicant]
JP 2010270310A · 2010 [cited by applicant]
JP 2011530579A · 2011 [cited by applicant]
RU 2562258C1 · 2015 [cited by examiner]
WO WO03070736A1 · 2003 [cited by applicant]
WO WO2006084488A1 · 2006 [cited by applicant]
WO WO2006084489A1 · 2006 [cited by applicant]
WO WO2008000920A1 · 2008 [cited by applicant]
WO WO2008101845A1 · 2008 [cited by applicant]
WO WO2010135398A1 · 2010 [cited by applicant]
WO WO2011000019A1 · 2011 [cited by applicant]
WO WO2011004739A1 · 2011 [cited by applicant]
WO WO2013020696A2 · 2013 [cited by applicant]
WO WO2013068437A2 · 2013 [cited by applicant]
WO WO2013072295A1 · 2013 [cited by applicant]
WO WO2014064064A1 · 2014 [cited by applicant]
WO WO2019063550A1 · 2019 [cited by applicant]
US 11,358,941 B2, 06/2022, Klein et al. (withdrawn) [cited by applicant]
U.S. Appl. No. 17/906,080, filed Sep. 12, 2022. [cited by applicant]
U.S. Appl. No. 17/907,038, filed Sep. 22, 2022. [cited by applicant]
U.S. Appl. No. 17/995,978, filed Oct. 11, 2022. [cited by applicant]
U.S. Appl. No. 17/996,747, filed Oct. 20, 2022. [cited by applicant]
U.S. Appl. No. 18/245,065, filed Mar. 13, 2023. [cited by applicant]
U.S. Appl. No. 18/251,255, filed May 1, 2023. [cited by applicant]
State Intellectual Property Organization of the People's Republic of China, Third Office Action in Chinese Patent Application No. 202080062735.0 (May 21, 2024). [cited by applicant]
Croitoru et al., “Biocatalytic acylation of sugar alcohols by 3-(4- hydroxyphenyl)propionic acid,” [cited by applicant]
“STN search report”, from the Chemical Library, provided by Interbioscreen Ltd., Database Registry (Online), CAS Registration No. 371953-68-3 (2011). [cited by applicant]
China National Intellectual Property Administration, First Office Action in Chinese Patent Application No. 202080062735.0 (Jul. 5, 2023). [cited by applicant]
Database Registry (STN) [Online], CAS Registration Nos. 1809735-17-8, 371953-68-3 (2015). [cited by applicant]
Japan Patent Office, Notification of Reasons for Refusal in Japanese Patent Application No. 2022-501007 (Feb. 6, 2024). [cited by applicant]
State Intellectual Property Organization of the People's Republic of China, Second Office Action in Chinese Patent Application No. 202080062735.0 (Feb. 27, 2024). [cited by applicant]
Japan Patent Office, Decision of Refusal in Japanese Patent Application No. 2022-501007 (Oct. 29, 2024). [cited by applicant]
Aubert et al., “Azoalkanes—novel flame retardants and their structure-property relationship,” [cited by applicant]
Aubert et al., “Azoalkanes: A Novel Class of Additives for Cross-Linking and Controlled Degradation of Polyolefins,” [cited by applicant]
Krönke et al., “Antioxidants,” [cited by applicant]
Pawelec et al., “Triazene compounds as a novel and effective class of flame retardants for polypropylene,” [cited by applicant]
German Patent Office, Office Action in German Patent Application No. 10 2019 210 040.6 (Sep. 16, 2019). [cited by applicant]
European Patent Office, International Search Report in International Application No. PCT/EP2020/069153 (Sep. 22, 2020). [cited by applicant]
European Patent Office, Written Opinion in International Application No. PCT/EP2020/069153 (Sep. 22, 2020). [cited by applicant]
International Bureau WIPO, International Preliminary Report on Patentability in International Application No. PCT/EP2020/069153 (Jan. 11, 2022). [cited by applicant]
U.S. Appl. No. 14/442,606, filed May 13, 2015. [cited by applicant]
U.S. Appl. No. 14/779,849, filed Sep. 24, 2015. [cited by applicant]
U.S. Appl. No. 15/311,674, filed Nov. 16, 2016. [cited by applicant]
U.S. Appl. No. 15/317,899, filed Dec. 9, 2016. [cited by applicant]
U.S. Appl. No. 15/511,410, filed Mar. 15, 2017. [cited by applicant]
U.S. Appl. No. 15/511,471, filed Mar. 15, 2017. [cited by applicant]
U.S. Appl. No. 15/511,445, filed Mar. 15, 2017. [cited by applicant]
U.S. Appl. No. 15/529,026, filed May 23, 2017. [cited by applicant]
U.S. Appl. No. 15/738,515, filed Dec. 20, 2017. [cited by applicant]
U.S. Appl. No. 16/344,830, filed Apr. 25, 2019. [cited by applicant]
U.S. Appl. No. 16/488,902, filed Aug. 26, 2019. [cited by applicant]
U.S. Appl. No. 16/633,645, filed Jan. 24, 2020. [cited by applicant]
U.S. Appl. No. 16/649,656, filed Mar. 22, 2020. [cited by applicant]
U.S. Appl. No. 16/764,291, filed May 14, 2020. [cited by applicant]
U.S. Appl. No. 17/287,079, filed Apr. 20, 2021. [cited by applicant]
U.S. Appl. No. 17/425,267, filed Jul. 22, 2021. [cited by applicant]
U.S. Appl. No. 17/423,800, filed Jul. 16, 2021. [cited by applicant]
U.S. Appl. No. 17/441,626, filed Sep. 21, 2021. [cited by applicant]
U.S. Appl. No. 17/640,174, filed Mar. 3, 2022. [cited by applicant]
Liu Xia et al., “Synthesis of Antioxidant Irganox 121” [cited by applicant]