IP Library › Granted Patent US 12,570,829
Granted Patent B2
US 12,570,829 · App. 17/622,891 · Granted Mar 10, 2026

Pipe made of peroxide-crosslinked polyethylene of high UV stability

Inventors: Franz Ruemer (Linz, AT); Reinhold Gard (Stenungsund, SE); Stefan Dreckoetter (Burghausen, DE)
Assignee: Borealis AG
C08K5/34926C08J3/24C08K5/1345C08K5/14F16L9/12C08J2323/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,570,829
App. No.
17/622,891
Granted
Mar 10, 2026
Kind
B2
Abstract

The present invention relates to a pipe which comprises (i) a peroxide-crosslinked polyethylene, and (ii) a sterically hindered amine which comprises the following repeating unit of formula (I).

Claims (25)

1 . A pipe comprising

a peroxide-crosslinked polyethylene, wherein the peroxide-crosslinked polyethylene is obtained from a crosslinkable polyethylene by a crosslinking treatment with a peroxide in the absence of any non-peroxide crosslinking agent,

wherein the crosslinkable polyethylene is an ethylene homopolymer or an ethylene copolymer with comonomer units derived from a C 3-8 alpha-olefin and/or a non-conjugated diene,

0.1 to 0.3 wt % of pentaerythritol tetrakis-3-(3′,5′-di-tert-butyl-4-hydroxyphenyl) propionate (CAS number 6683-19-8), 0.08 to 0.35 wt % octadecyl-3-(3′,5′-di-tert-butyl-4-hydroxyphenyl) propionate (CAS No. 2082-79-3), and 0.25 to 0.65 wt % of 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxy benzyl) benzene (CAS number 1709-70-2), and

a sterically hindered amine which comprises the following repeating unit of formula (I):

wherein x is 4-8, R 1 and R 2 , independently from each other, are H or methyl; and

R 3 and R 4 , independently from each other, are H, a C 2-12 alkyl group, a C 5-7 cycloalkyl group, or a saturated nitrogen-containing heterocyclic group; or R 3 and R 4 , together with the nitrogen atom to which they are attached, form a 5- to 7-membered saturated heterocyclic ring.

2 . The pipe according to claim 1 , wherein x is 6, R 3 is a C 2-12 alkyl group, and R 4 is H or a saturated nitrogen-containing heterocyclic group.

3 . The pipe according to claim 1 , wherein the sterically hindered amine is poly ((6-((1,1,3,3-tetramethylbutyl) amino)-1,3,5-triazine-2,4-diyl)((2,2,6,6-tetramethyl-4-piperidinyl) imino)-1,6-hexanediyl ((2.2.6.6-tetramethyl-4-piperidinyl) imino)); 1,6-hexanediamine, N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl)-, polymer with 2,4,6-trichloro-1,3,5-triazine, reaction products with N-butyl-1-butanamine and N-butyl-2,2,6,6-tetramethyl-4-piperidinamine; or a mixture thereof.

4 . The pipe according to claim 1 , wherein the sterically hindered amine is present in an amount of 0.01 wt % to 1 wt %, based on the weight of the peroxide-crosslinked polyethylene.

5 . A process for preparing the pipe according to claim 1 , which comprises providing a crosslinkable composition comprising

a crosslinkable polyethylene, which is an ethylene homopolymer or an ethylene copolymer with comonomer units derived from a C 3-8 alpha-olefin and/or a non-conjugated diene,

a peroxide,

antioxidants pentaerythritol tetrakis-3-(3′,5′-di-tert-butyl-4-hydroxyphenyl) propionate (CAS number 6683-19-8), octadecyl-3-(3′,5′-di-tert-butyl-4-hydroxyphenyl) propionate (CAS No. 2082-79-3), and 1,3,5-trimethyl-2,4,6-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) benzene (CAS number 1709-70-2), and

a sterically hindered amine which comprises the following unit of formula (I);

forming the crosslinkable composition into a pipe, and crosslinking the crosslinkable polyethylene by a crosslinking treatment with the peroxide in the absence of any non-peroxide crosslinking agent.

6 . The process according to claim 5 , wherein the crosslinkable composition is provided by preparing pellets which contain the crosslinkable polyethylene, the antioxidants, and the sterically hindered amine, and the pellets are brought into contact with the peroxide.

7 . The process according to claim 5 , wherein the pipe is formed by extrusion.

8 . A method of transporting water comprising transporting water through the pipe according to claim 1 .

9 . The process according to claim 5 , wherein the pipe is formed by screw extrusion or ram extrusion.

10 . The pipe according to claim 1 , wherein the crosslinkable polyethylene is prepared in the presence of a chromium catalyst, a Ziegler-Natta catalyst, or a metallocene catalyst.

11 . The process according to claim 5 , wherein the crosslinkable polyethylene is prepared in the presence of a chromium catalyst, a Ziegler-Natta catalyst, or a metallocene catalyst.

12 . The pipe according to claim 1 , wherein the crosslinkable polyethylene has a melt flow rate MFR (190° C./21.6 kg), measured according to ISO 1133 of from 1 g/10 min to 50 g/10 min, a density measured according to ISO 1183-1: method A, of from 935 kg/m 3 to 965 kg/m 3 , and 0.05 terminal vinyl groups/1000 carbon atoms to 2.5 terminal vinyl groups/1000 carbon atoms.

13 . The process according to claim 5 , wherein the crosslinkable polyethylene has a melt flow rate MFR (190° C./21.6 kg), measured according to ISO 1133 of from 1 g/10 min to 50 g/10 min, a density measured according to ISO 1183-1: method A, of from 935 kg/m 3 to 965 kg/m 3 , and 0.05 terminal vinyl groups/1000 carbon atoms to 2.5 terminal vinyl groups/1000 carbon atoms.

14 . The process according to claim 5 , wherein the sterically hindered amine further comprises poly ((6-((1,1,3,3-tetramethylbutyl) amino)-1,3,5-triazine-2,4-diyl) ((2,2,6,6-tetramethyl-4-piperidinyl) imino)-1,6-hexanediyl ((2,2,6,6-tetramethyl-4-piperidinyl) imino)).

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2022
From: RUEMER, FRANZ; DRECKOETTER, STEFAN
To: BOREALIS AG
Reel/Frame 059608/0358 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2022
From: GARD, REINHOLD
To: BOREALIS AG
Reel/Frame 059608/0361 →
ASSIGNEE ADDRESS CHANGE Recorded Apr 15, 2022
From: BOREALIS AG
To: BOREALIS AG
Reel/Frame 059720/0470 →
Priority Claims (1)
EP 19183634 · Jul 1, 2019 · regional
Continuity (1)
Related Publication 20220227965A1 · Jul 21, 2022
References Cited (129)
US 6455616B1 · Cogen · 2002 [cited by applicant]
US 6828364B2 · Gugumus · 2004 [cited by examiner]
US 7744972B2 · Ho · 2010 [cited by examiner]
US 8247696B2 · Smedberg · 2012 [cited by examiner]
US 9637602B2 · Potter et al. · 2017 [cited by applicant]
US 9670293B2 · Reznichenko et al. · 2017 [cited by applicant]
US 9670347B2 · Tölsch et al. · 2017 [cited by applicant]
US 9708481B2 · Wang et al. · 2017 [cited by applicant]
US 9745431B2 · Potter et al. · 2017 [cited by applicant]
US 9751962B2 · Wang et al. · 2017 [cited by applicant]
US 9777142B2 · Sandholzer et al. · 2017 [cited by applicant]
US 9802394B2 · Cavacas et al. · 2017 [cited by applicant]
US 9828698B2 · Wang et al. · 2017 [cited by applicant]
US 9890275B2 · Sandholzer et al. · 2018 [cited by applicant]
US 9976020B2 · Nummila-Pakarinen et al. · 2018 [cited by applicant]
US 10011708B2 · Lampela et al. · 2018 [cited by applicant]
US 10030109B2 · Boragno et al. · 2018 [cited by applicant]
US 10040930B2 · Gloger et al. · 2018 [cited by applicant]
US 10100185B2 · Wang et al. · 2018 [cited by applicant]
US 10100186B2 · Wang et al. · 2018 [cited by applicant]
US 10227427B2 · Reichelt et al. · 2019 [cited by applicant]
US 10450451B2 · Wang et al. · 2019 [cited by applicant]
US 10519259B2 · Resconi et al. · 2019 [cited by applicant]
US 10870718B2 · Denifl et al. · 2020 [cited by applicant]
US 11292900B2 · Gahleitner et al. · 2022 [cited by applicant]
US 11299617B2 · Prieto et al. · 2022 [cited by applicant]
US 11390732B2 · Van Houcke et al. · 2022 [cited by applicant]
US 11492478B2 · Kniesel et al. · 2022 [cited by applicant]
US 11504949B2 · Oderkerk et al. · 2022 [cited by applicant]
US 11518863B2 · Vijay · 2022 [cited by applicant]
US 11530321B2 · Kniesel et al. · 2022 [cited by applicant]
US 20030225191A1 · Gugumus · 2003 [cited by examiner]
US 20050148700A1 · Kramer · 2005 [cited by examiner]
US 20100149607A1 · Langrel et al. · 2010 [cited by applicant]
US 20120125469A1 · Ericsson et al. · 2012 [cited by applicant]
US 20120295048A1 · Al-Malaika et al. · 2012 [cited by applicant]
US 20160185946A1 · Sandholzer et al. · 2016 [cited by applicant]
US 20160194486A1 · Sandholzer et al. · 2016 [cited by applicant]
US 20160200838A1 · Reznichenko et al. · 2016 [cited by applicant]
US 20160208085A1 · Gloger et al. · 2016 [cited by applicant]
US 20160229158A1 · Cavacas et al. · 2016 [cited by applicant]
US 20160237270A1 · Wang et al. · 2016 [cited by applicant]
US 20160244539A1 · Resconi et al. · 2016 [cited by applicant]
US 20160272740A1 · Wang et al. · 2016 [cited by applicant]
US 20160280899A1 · Töltsch et al. · 2016 [cited by applicant]
US 20160304681A1 · Potter et al. · 2016 [cited by applicant]
US 20160311951A1 · Reichelt et al. · 2016 [cited by applicant]
US 20160311988A1 · Potter et al. · 2016 [cited by applicant]
US 20160312018A1 · Vestberg et al. · 2016 [cited by applicant]
US 20160312019A1 · Lampela et al. · 2016 [cited by applicant]
US 20160347943A1 · Wang et al. · 2016 [cited by applicant]
US 20160347944A1 · Wang et al. · 2016 [cited by applicant]
US 20170009068A1 · Kahlen et al. · 2017 [cited by applicant]
US 20170029980A1 · Wang et al. · 2017 [cited by applicant]
US 20170137617A1 · Wang et al. · 2017 [cited by applicant]
US 20170166711A1 · Boragno et al. · 2017 [cited by applicant]
US 20170218172A1 · Wang et al. · 2017 [cited by applicant]
US 20170313867A1 · Lampela et al. · 2017 [cited by applicant]
US 20170321048A1 · Nummila-Pakarinen et al. · 2017 [cited by applicant]
US 20180079875A1 · Braun et al. · 2018 [cited by applicant]
US 20180112070A1 · Hiramoto · 2018 [cited by examiner]
US 20180194881A1 · Denifl et al. · 2018 [cited by applicant]
US 20180355076A1 · Garg · 2018 [cited by examiner]
US 20200263015A1 · Kniesel et al. · 2020 [cited by applicant]
US 20200270434A1 · Van Houcke et al. · 2020 [cited by applicant]
US 20200277479A1 · Jerabek et al. · 2020 [cited by applicant]
US 20200308353A1 · Jerabek et al. · 2020 [cited by applicant]
US 20200308385A1 · Gahleitner et al. · 2020 [cited by applicant]
US 20200347216A1 · Kniesel et al. · 2020 [cited by applicant]
US 20200392321A1 · Gahleitner et al. · 2020 [cited by applicant]
US 20210114352A1 · Oderkerk et al. · 2021 [cited by applicant]
US 20210171749A1 · Kumar et al. · 2021 [cited by applicant]
US 20210171750A1 · Gahleitner et al. · 2021 [cited by applicant]
US 20210214527A1 · Gahleitner et al. · 2021 [cited by applicant]
US 20210214533A1 · Kulshreshtha et al. · 2021 [cited by applicant]
US 20210238376A1 · Kahlen et al. · 2021 [cited by applicant]
US 20210253836A1 · Gahleitner et al. · 2021 [cited by applicant]
US 20210269560A1 · Krallis et al. · 2021 [cited by applicant]
US 20210324189A1 · Prieto et al. · 2021 [cited by applicant]
US 20210332227A1 · Wang et al. · 2021 [cited by applicant]
US 20210347971A1 · Wang et al. · 2021 [cited by applicant]
US 20220033631A1 · Gloger et al. · 2022 [cited by applicant]
US 20220135779A1 · Wang et al. · 2022 [cited by applicant]
US 20220204719A1 · Vijay · 2022 [cited by applicant]
US 20220251256A1 · Wang et al. · 2022 [cited by applicant]
US 20220289955A1 · Kahlen et al. · 2022 [cited by applicant]
US 20220306844A1 · Kahlen et al. · 2022 [cited by applicant]
US 20220315716A1 · Prieto et al. · 2022 [cited by applicant]
US 20220356330A1 · Kahlen et al. · 2022 [cited by applicant]
US 20230046086A1 · Al-Haj Ali et al. · 2023 [cited by applicant]
US 20230047329A1 · Al-Haj Ali · 2023 [cited by applicant]
US 20230212338A1 · Wang et al. · 2023 [cited by applicant]
CN 106633315A · 2017 [cited by applicant]
JP 01288425A · 1989 [cited by examiner]
JP 2012162645A · 2012 [cited by examiner]
JP 2017066332A · 2017 [cited by examiner]
WO 03064511A2 · 2003 [cited by applicant]
WO WO2004067610A1 · 2004 [cited by applicant]
WO WO2010072375A1 · 2010 [cited by applicant]
WO WO2010138816A1 · 2010 [cited by applicant]
WO WO2011092476A1 · 2011 [cited by applicant]
WO WO2016170016A1 · 2016 [cited by applicant]
Google machine translation of JP 01288425 (2024, 6pages). [cited by examiner]
WIPO machine translation of JP '01288425 (2024, 3 pages). [cited by examiner]
Machine translation of JP 2012162645-A (2012, 7 pages). [cited by examiner]
Machine translation of JP 2017066332-A (2017, 27 pages). [cited by examiner]
Busico et al., “ [cited by applicant]
He et al., “Unexpected proton spin-lattice relaxation in the solutions of polyolefin and tetrachloroethane,” [cited by applicant]
Malpas, “An Overview of Industrial Polyethylene Processes,” [cited by applicant]
Malpas, “Chromium Catalysts,” [cited by applicant]
European Patent Office, Extended European Search Report in European Patent Application No. 19183634.5 (Jan. 14, 2020). [cited by applicant]
European Patent Office, International Search Report in International Application No. PCT/EP2020/066582 (Sep. 21, 2020). [cited by applicant]
European Patent Office, Written Opinion in International Application No. PCT/EP2020/066582 (Sep. 21, 2020). [cited by applicant]
International Bureau of WIPO, International Preliminary Report on Patentability in International Application No. PCT/EP2020/066582 (Dec. 28, 2021). [cited by applicant]
U.S. Appl. No. 15/310,283, filed Nov. 10, 2016, Patented. [cited by applicant]
U.S. Appl. No. 16/761,743, filed May 5, 2020, Patented. [cited by applicant]
U.S. Appl. No. 16/761,757, filed May 5, 2020, Patented. [cited by applicant]
U.S. Appl. No. 16/652,115, filed Mar. 30, 2020, Patented. [cited by applicant]
U.S. Appl. No. 16/768,330, filed May 29, 2020, Patented. [cited by applicant]
U.S. Appl. No. 16/982,385, filed Sep. 18, 2020, Abandoned/Expired. [cited by applicant]
U.S. Appl. No. 17/047,350, filed Oct. 13, 2020, Patented. [cited by applicant]
U.S. Appl. No. 17/276,322, filed Mar. 15, 2021, Patented. [cited by applicant]
U.S. Appl. No. 17/624,609, filed Jan. 4, 2022, Patented. [cited by applicant]
U.S. Appl. No. 17/791,987, filed Jul. 11, 2022, Pending. [cited by applicant]
U.S. Appl. No. 17/792,003, filed Jul. 11, 2022, Pending. [cited by applicant]
U.S. Appl. No. 17/995,997, filed Oct. 12, 2022, Pending. [cited by applicant]
Hongfa et al., A Handbook of Industrial Assistants, [cited by applicant]
Juying et al., Quick Reference Manual for Plastic Additives Variety and Selection, [cited by applicant]
China National Intellectual Property Administration, The Second Office Action in Chinese Patent Application No. 202080047304.7 (Jun. 16, 2023). [cited by applicant]