IP Library › Granted Patent US 12,534,564
Granted Patent B2
US 12,534,564 · App. 17/414,678 · Granted Jan 27, 2026

Production of rigid polyurethane foam

Inventors: Martin Glos (Borken, DE); Jobst Grimminger (Ellerau, DE); Michael Ferenz (Essen, DE)
Assignee: Evonik Operations GmbH
C08G18/3893C08G2110/0025
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 12,534,564
App. No.
17/414,678
Granted
Jan 27, 2026
Kind
B2
Abstract

What are described are (a) a composition suitable for production of rigid polyurethane foam, comprising at least one isocyanate component, a polyol component, optionally a catalyst that catalyses the formation of a urethane or isocyanurate bond, optionally blowing agents, where the composition additionally comprises polyalkylsiloxane (PAS) containing no polyether modification, and polyether-modified siloxane, (b) a process for producing rigid polyurethane foam using polyalkylsiloxanes and polyether-modified siloxane, (c) the rigid polyurethane foam Thus obtainable and (d) the use thereof.

Claims (49)

1. A composition for production of rigid polyurethane foam, the composition comprising at least one isocyanate component, a polyol component, optionally a catalyst that catalyses the formation of a urethane or isocyanurate bond, optionally blowing agents, where the composition additionally comprises:

i) a polyalkylsiloxane composition comprising at least one poly alkylsiloxane containing no polyether modification comprising a polyalkylsiloxane having a structure

and

ii) a polyether-modified siloxane.

2. The composition according to claim 1 , wherein said polyalkylsiloxane composition further comprises a polyalkylsiloxane having no polyether modification having less than 20 silicon atoms.

3. The composition according to claim 2 , wherein the polyalkylsiloxane having no polyether modification having less than 20 silicon atoms conforms to the formula 1:

M a D b T c Q d   (Formula 1)

where

M=R 11 R 12 R 13 SiO 1/2

D=R 14 R 15 SiO 2/2

T=R 16 SiO 3/2

Q=SiO 4/2

where

R 11 , R 12 , R 13 , R 14 , R 15 , R 16 =identical or different hydrocarbon radicals having 1 to 12 carbon atoms, where the hydrocarbon radicals are optionally substituted by heteroatoms, excluding oxygen, or else H,

and wherein

a=2 to 6

b=0 to 8,

c=0 to 4,

d=0 to 2,

wherein a +b+c+d<20.

4. The composition according to claim 3 ,

wherein

c+d>0.5.

5. The composition according to claim 3 ,

wherein

d=0 and c >0.5.

6. The composition according to claim 3 ,

wherein

c+d<0.5.

7. The composition according to claim 3 ,

wherein

R 16 is different from R 11 , R 12 , R 13 , R 14 and R 15 .

8. The composition according to claim 3 ,

wherein

R 11 , R 12 and R 13 are different.

9. The composition according to claim 3 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 =identical or different hydrocarbon radicals having 1 to 8 carbon atoms,

wherein a+b+c+d<11.

10. The composition according to claim 3 , wherein c+d>1.

11. The composition according to claim 5 , wherein c+d <0.1.

12. The composition according to claim 3 , wherein R 11 , R 12 , R 13 , R 14 , R 15 , R 16 =identical or different hydrocarbon radicals selected from the group consisting of phenyl-, CH 3 —, CH 3 CH 2 —, CH 2 CH—, ClCH 2 CH 2 CH 2 — and H—.

13. The composition according to claim 2 , wherein the polyalkylsiloxane having no polyether modification contains less than 11 silicon atoms.

14. The composition according to claim 1 , wherein the polyalkylsiloxane composition is used in combination with said polyether-modified siloxane in a mass ratio of from 1:5 to 1:200.

15. The composition according to claim 1 , wherein the proportion by mass of the total amount of polyalkylsiloxane composition and polyether-modified siloxanes, based on 100 parts by mass of polyol component, is from 0.1 to 10 pphp.

16. The composition according to claim 1 , wherein the proportion by mass of the total amount of polyalkylsiloxane composition and polyether-modified siloxanes, based on 100 parts by mass of polyol component, is from 1 to 3 pphp.

17. The process for producing rigid polyurethane foam by reacting one or more polyol components with one or more isocyanate components, wherein the reaction is effected in the presence of i) a polyalkylsiloxane composition comprising at least one polyalkylsiloxane containing no polyether modification comprising a polyalkylsiloxane having a structure

and

ii) a polyether-modified siloxane, using a composition according to claim 1 .

18. The rigid polyurethane foam obtained by the process according to claim 17 .

19. An insulant comprising the rigid polyurethane foam according to claim 18 .

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE UNDERLYING DOCUMENT PREVIOUSLY RECORDED AT REEL: 056564 FRAME: 0894. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 16, 2023
From: GLOS, MARTIN; GRIMMINGER, JOBST; FERENZ, MICHAEL
To: EVONIK OPERATIONS GMBH
Reel/Frame 062776/0111 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2021
From: GLOS, MARTIN; GRIMMINGER, JOBST; FERENZ, MICHAEL
To: EVONIK OPERATIONS GMBH
Reel/Frame 056564/0894 →
Priority Claims (1)
EP 19150460 · Jan 7, 2019 · regional
Continuity (1)
Related Publication 20220017679A1 · Jan 20, 2022
References Cited (210)
US 3879433A · Omietanski et al. · 1975 [cited by applicant]
US 3900424A · Inoue et al. · 1975 [cited by applicant]
US 3953383A · Inoue et al. · 1976 [cited by applicant]
US 4042540A · Lammerting et al. · 1977 [cited by applicant]
US 4412081A · Williams · 1983 [cited by applicant]
US 4478957A · Klietsch et al. · 1984 [cited by applicant]
US 4500704A · Kruper et al. · 1985 [cited by applicant]
US 4751251A · Thornsberry · 1988 [cited by applicant]
US 5064870A · Kollmeier et al. · 1991 [cited by applicant]
US 5096933A · Volkert · 1992 [cited by applicant]
US 5310766A · Baumann et al. · 1994 [cited by applicant]
US 5633292A · Bruene et al. · 1997 [cited by applicant]
US 5844010A · Burkhart et al. · 1998 [cited by applicant]
US 5852065A · Frey et al. · 1998 [cited by applicant]
US 5990187A · Boinowitz et al. · 1999 [cited by applicant]
US 6506810B2 · Borgogelli et al. · 2003 [cited by applicant]
US 7138552B2 · Kaizik et al. · 2006 [cited by applicant]
US 7157541B2 · Knott et al. · 2007 [cited by applicant]
US 7605284B2 · Brueckner et al. · 2009 [cited by applicant]
US 7671104B2 · Heinemann et al. · 2010 [cited by applicant]
US 7838566B2 · Glos et al. · 2010 [cited by applicant]
US 7872055B2 · Burdeniuc et al. · 2011 [cited by applicant]
US 8030366B2 · Ferenz et al. · 2011 [cited by applicant]
US 8138294B2 · Henning et al. · 2012 [cited by applicant]
US 8247467B2 · Mijolovic et al. · 2012 [cited by applicant]
US 8293808B2 · Herrington et al. · 2012 [cited by applicant]
US 8349907B2 · Henning et al. · 2013 [cited by applicant]
US 8420748B2 · Henning et al. · 2013 [cited by applicant]
US 8623984B2 · Henning et al. · 2014 [cited by applicant]
US 8729207B2 · Hartung et al. · 2014 [cited by applicant]
US 8802744B2 · Knott et al. · 2014 [cited by applicant]
US 8906974B2 · Glos et al. · 2014 [cited by applicant]
US 8912277B2 · Glos · 2014 [cited by applicant]
US 8946310B2 · Glos et al. · 2015 [cited by applicant]
US 8946369B2 · Henning et al. · 2015 [cited by applicant]
US 8957121B2 · Schiller et al. · 2015 [cited by applicant]
US 9035011B2 · Ferenz et al. · 2015 [cited by applicant]
US 9212195B1 · Dyballa et al. · 2015 [cited by applicant]
US 9221850B2 · Dyballa et al. · 2015 [cited by applicant]
US 9221851B2 · Dyballa et al. · 2015 [cited by applicant]
US 9290604B2 · Andrew et al. · 2016 [cited by applicant]
US 9334354B2 · Ferenz et al. · 2016 [cited by applicant]
US 9540500B2 · Ferenz et al. · 2017 [cited by applicant]
US 9657144B2 · Hubel et al. · 2017 [cited by applicant]
US 9682898B2 · Peitz et al. · 2017 [cited by applicant]
US 9737884B2 · Dyballa et al. · 2017 [cited by applicant]
US 9751904B2 · Dyballa et al. · 2017 [cited by applicant]
US 9840524B2 · Dyballa et al. · 2017 [cited by applicant]
US 9914681B2 · Geilen et al. · 2018 [cited by applicant]
US 10023679B2 · Klostermann et al. · 2018 [cited by applicant]
US 10351687B2 · Diendorf et al. · 2019 [cited by applicant]
US 10870723B2 · Glos · 2020 [cited by applicant]
US 10961418B2 · Kolb et al. · 2021 [cited by applicant]
US 20020103091A1 · Kodali · 2002 [cited by applicant]
US 20050131090A1 · Furlan et al. · 2005 [cited by applicant]
US 20060155090A1 · Ferenz · 2006 [cited by applicant]
US 20060167125A1 · Bauer et al. · 2006 [cited by applicant]
US 20060229375A1 · Hsiao et al. · 2006 [cited by applicant]
US 20060293400A1 · Wiltz et al. · 2006 [cited by applicant]
US 20070066697A1 · Gilder et al. · 2007 [cited by applicant]
US 20070072951A1 · Bender et al. · 2007 [cited by applicant]
US 20070078193A1 · Gilder et al. · 2007 [cited by applicant]
US 20070270518A1 · Nutzel · 2007 [cited by applicant]
US 20080125503A1 · Henning et al. · 2008 [cited by applicant]
US 20090088488A1 · Bruckner et al. · 2009 [cited by applicant]
US 20110062370A1 · Eilbracht et al. · 2011 [cited by applicant]
US 20110218259A1 · Eling et al. · 2011 [cited by applicant]
US 20110306694A1 · Glos et al. · 2011 [cited by applicant]
US 20120153210A1 · Glos et al. · 2012 [cited by applicant]
US 20120264843A1 · Glos · 2012 [cited by applicant]
US 20130035407A1 · Lobert et al. · 2013 [cited by applicant]
US 20130338324A1 · Beierlein et al. · 2013 [cited by applicant]
US 20130345318A1 · Schubert et al. · 2013 [cited by applicant]
US 20150057384A1 · Glos et al. · 2015 [cited by applicant]
US 20160075846A1 · Krebs et al. · 2016 [cited by applicant]
US 20160096939A1 · Glos et al. · 2016 [cited by applicant]
US 20160152739A1 · Eilbracht et al. · 2016 [cited by applicant]
US 20160326330A1 · Schuette et al. · 2016 [cited by applicant]
US 20180016392A1 · Lobert et al. · 2018 [cited by applicant]
US 20180186924A1 · Giesker et al. · 2018 [cited by applicant]
US 20180327563A1 · Klostermann et al. · 2018 [cited by applicant]
US 20190233571A1 · Diendorf et al. · 2019 [cited by applicant]
US 20190233646A1 · Inagaki et al. · 2019 [cited by applicant]
US 20200239621A1 · Glos · 2020 [cited by applicant]
US 20200377669A1 · Knott et al. · 2020 [cited by applicant]
US 20200377684A1 · Hermann et al. · 2020 [cited by applicant]
US 20210047471A1 · Chen et al. · 2021 [cited by applicant]
US 20220017717A1 · Chaffanjon et al. · 2022 [cited by applicant]
US 20220041829A1 · Glos et al. · 2022 [cited by applicant]
CN 101880452 · 2010 [cited by applicant]
CN 101880453 · 2010 [cited by applicant]
CN 103044687 · 2013 [cited by applicant]
CN 103055759 · 2013 [cited by applicant]
CN 103657518 · 2014 [cited by applicant]
CN 103665385 · 2014 [cited by applicant]
CN 107922740A · 2018 [cited by applicant]
DE 2533074A1 · 1976 [cited by applicant]
DE 3215317C1 · 1983 [cited by applicant]
DE 3234462C1 · 1984 [cited by applicant]
DE 4411161 · 1994 [cited by applicant]
DE 4444898C1 · 1996 [cited by applicant]
DE 102008007081 · 2009 [cited by applicant]
DE 102013212481 · 2014 [cited by applicant]
EP 0258600A2 · 1988 [cited by applicant]
EP 0275563A1 · 1988 [cited by applicant]
EP 0421269 · 1991 [cited by applicant]
EP 0533202A1 · 1993 [cited by applicant]
EP 0570174B1 · 1993 [cited by applicant]
EP 0704468 · 1996 [cited by applicant]
EP 0739932 · 1996 [cited by applicant]
EP 0867464A1 · 1998 [cited by applicant]
EP 0867465A1 · 1998 [cited by applicant]
EP 0045B1 · 1998 [cited by applicant]
EP 1095968A1 · 2001 [cited by applicant]
EP 1161474A1 · 2001 [cited by applicant]
EP 1211279A1 · 2002 [cited by applicant]
EP 1520870A1 · 2005 [cited by applicant]
EP 1544235A1 · 2005 [cited by applicant]
EP 1678232A2 · 2006 [cited by applicant]
EP 1712578A1 · 2006 [cited by applicant]
EP 1873209A2 · 2008 [cited by applicant]
EP 1515934 · 2008 [cited by applicant]
EP 2368927A1 · 2011 [cited by applicant]
EP 2465891A1 · 2012 [cited by applicant]
EP 2465892 · 2012 [cited by applicant]
EP 2465892A1 · 2012 [cited by applicant]
EP 2492292 · 2012 [cited by applicant]
EP 2947064 · 2015 [cited by applicant]
EP 3115389 · 2017 [cited by applicant]
EP 3243863A1 · 2017 [cited by applicant]
JP S57212219 · 1982 [cited by applicant]
JP H0418431 · 1992 [cited by applicant]
JP H05255468 · 1993 [cited by applicant]
JP H08156143 · 1996 [cited by applicant]
JP H09165427 · 1997 [cited by applicant]
JP H09165428 · 1997 [cited by applicant]
JP 2001040054 · 2001 [cited by applicant]
JP 2001040055 · 2001 [cited by applicant]
JP 2002003565 · 2002 [cited by applicant]
JP 2003055424 · 2003 [cited by applicant]
JP 2004315579 · 2004 [cited by applicant]
JP 2004315580 · 2004 [cited by applicant]
JP 2005171102 · 2005 [cited by applicant]
JP 2005344079 · 2005 [cited by applicant]
JP 2006241312 · 2006 [cited by applicant]
JP 2010180369A · 2010 [cited by examiner]
JP 20121574 · 2012 [cited by applicant]
KR 20130007896 · 2013 [cited by applicant]
WO 0047647A1 · 2000 [cited by applicant]
WO 0058383A1 · 2000 [cited by applicant]
WO 2004020497A1 · 2004 [cited by applicant]
WO 2004096882A1 · 2004 [cited by applicant]
WO 2005033167A2 · 2005 [cited by applicant]
WO 2005085310A2 · 2005 [cited by applicant]
WO 2006094227A2 · 2006 [cited by applicant]
WO 2006116456A1 · 2006 [cited by applicant]
WO 2008058913A1 · 2008 [cited by applicant]
WO 2009058367A1 · 2009 [cited by applicant]
WO 2009130470A1 · 2009 [cited by applicant]
WO 2010028362A1 · 2010 [cited by applicant]
WO 2010111021 · 2010 [cited by applicant]
WO 2011012390A1 · 2011 [cited by applicant]
WO 2011163133A1 · 2011 [cited by applicant]
WO 2012021675 · 2012 [cited by applicant]
WO 2012031868 · 2012 [cited by applicant]
WO 2013022932A1 · 2013 [cited by applicant]
WO 2013156237 · 2013 [cited by applicant]
WO 2015028295A1 · 2015 [cited by applicant]
WO 2015101497 · 2015 [cited by applicant]
WO 2015101497A1 · 2015 [cited by applicant]
WO 2016202912 · 2016 [cited by applicant]
WO 2017220332 · 2017 [cited by applicant]
WO 2017220332A1 · 2017 [cited by applicant]
WO 2020076539A1 · 2020 [cited by applicant]
WO 2020106538 · 2020 [cited by applicant]
WO 2021069164A1 · 2021 [cited by applicant]
WO 2021165149A1 · 2021 [cited by applicant]
WO 2021212317A1 · 2021 [cited by applicant]
JP2003-55424 machine translation (Year: 2024). [cited by examiner]
European Search Report dated Jul. 10, 2019, in European Application No. 19150465.3, 8 pages. [cited by applicant]
Gao et al., Effects of raw and poly(propylene oxide) grafted nanosilica on the morphology and thermal and mechanical properties of polyurethane foam, copyright 2015, J. Appl. Polym. Sci., May 14, 2015, pp. 42400:1-10. [cited by applicant]
International Search Report mailed on Feb. 27, 2020, in PCT/EP2019/085264, with English translation 7 pages. [cited by applicant]
Liang et al., “Preparation and Characterization of Thermoregulated Rigid Polyurethane Foams Containing Nanoencapsulated Phase Change Materials,” copyright 2016, Ind. Eng. Chem. Res., vol. 55, Feb. 23, 2016, pp. 2721-237… [cited by applicant]
Written Opinion dated Feb. 27, 2020, in PCT/EP2019/085264, with English translation, 14 pages. [cited by applicant]
Glos et al., U.S. Appl. No. 17/414,726, filed Jun. 16, 2021. [cited by applicant]
Wagner et al., U.S. Appl. No. 17/239,087, filed Apr. 23, 2021. [cited by applicant]
Wagner et al., U.S. Appl. No. 17/391,644, filed Aug. 2, 2021. [cited by applicant]
International Preliminary Report on Patentability received for PCT Application No. PCT/US2019/061387, mailed on Jun. 3, 2021, 10 pages. [cited by applicant]
International Search Report received for PCT Application No. PCT/US2019/061387, mailed on Feb. 28, 2020, 4 pages. [cited by applicant]
Written Opinion received for PCT Application No. PCT/US2019/061387, mailed on Feb. 28, 2020, 8 pages. [cited by applicant]
English International Search Report mailed on Apr. 2, 2020 in PCT/EP2019/085263 (3 pages). [cited by applicant]
European Search Report mailed on Jul. 10, 2019 in EP 19150460.4 (8 pages). [cited by applicant]
German International Search Report mailed on Apr. 2, 2020 in PCT/EP2019/085263 (4 pages). [cited by applicant]
German Written Opinion mailed on Apr. 2, 2020 in PCT/EP2019/085263 (8 pages). [cited by applicant]
European Search Report mailed on Jul. 10, 2019, in European Application No. 19150460.4, 8 pages. [cited by applicant]
Written Opinion mailed on Apr. 2, 2020, in PCT/EP2019/085263, with English translation, 15 pages. [cited by applicant]
U.S. Office Action dated Apr. 8, 2024, in U.S. Appl. No. 17/414,726, 27 pages. [cited by applicant]
“Ergänzende Laborversuche”, Feb. 1, 2024, 3 pages with English translation. [cited by applicant]
BASF SE, “Sicherheitsdatenblatt”, Jan. 26, 2024, 39 pages with English translation. [cited by applicant]
Evonik Oxeno GmbH & Co. KG, “OXO OIL LS 13”, Product Information, May 2023, pp. 1-2. [cited by applicant]
Fiche de données de sécurité, “Shell Ondina Oil 68”, Jan. 12, 2006, 10 pages with English translation. [cited by applicant]
Lubricant Base Oils Product Stewardship Summary, “White mineral oil (petroleum) Product Stewardship Summary”, Aug. 2013, 1 page. [cited by applicant]
Evonik Industries, “TEGOSTAB® B 1048”, Jul. 2007, 1 page. [cited by applicant]
Safety Data Sheet, “Shell Ondina Oil 68”, Jan. 15, 2016, 1 page. [cited by applicant]
Sasol, “PARAFOL 14 RSPO-MB”, Product Information, Oct. 18, 2018, pp. 1-7. [cited by applicant]
Technical Data Sheet, “Shell Ondina Oil 68”, Medicinal White Oils, 2021, 2 pages. [cited by applicant]
“C1012 Normal Paraffin”, Technical Data Sheet, 2011, 1 page. [cited by applicant]
“Hydrocarbons-Physical Data”, The Engineering Toolbox, 2 pages. [cited by applicant]
Office Action received for U.S. Appl. No. 17/414,726, mailed on Jul. 3, 2025, 16 pages. [cited by applicant]
U.S. Appl. No. 17/414,726, filed Jun. 16, 2021, Patent Publication No. 2022/0041829, Glos et al. [cited by applicant]