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# c12) United States Patent 

# Richter 

# (54) METHOD FOR ISOCYANATE MODIFICATION USING CATALYSTS WITH AN NPN SEQUENCE 

(71) Applicant: Covestro Deutschland AG, Leverkusen (DE) 

(72) Inventor: Frank Richter, Leverkusen (DE) 

(73) Assignee: Covestro Deutschland AG, Leverkusen (DE) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 64 days. 

(21) Appl. No.: 15/119,179 

(22) PCT Filed: Feb. 13, 2015 

(86) PCT No.: PCT/EP2015/053085 § 371 (c)(l), (2) Date: Aug. 16, 2016 

(87) PCT Pub. No.: WO2015/124503 PCT Pub. Date: Aug. 27, 2015 

## (65) Prior Publication Data 

US 2017/0008996 Al Jan. 12, 2017 

## (30) Foreign Application Priority Data 

Feb. 18, 2014 (EP) ..................................... 14155524 

(51) Int. Cl. 

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(52) U.S. Cl. CPC .......... C08G 1811883 (2013.01); C07F 9/067 (2013.01); C08G 18102 (2013.01); C08G 181022 (2013.01); C08G 181027 (2013.01); C08G 181092 (2013.01); C08G 181095 (2013.01); C08G 181097 (2013.01); C08G 18173 (2013.01) 

(58) Field of Classification Search CPC .. C08G 18/1883; C08G 18/02; C08G 18/022; C08G 18/027; C08G 18/092; C08G 18/095; C08G 18/097 See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

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# (IO) Patent No.: US 10,131,736 B2 

# (45) Date of Patent: Nov. 20, 2018 

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Document N_English Translation Dec. 13, 2017.* The Synthesis of Aliphatic Polyisocyanates Containing Biuret, Isocyanurate or Uretdione Backbones for use in Coatings, Laas, et al., J. Prakt Chem., 1994, 336, 185-200. 1,4,2-Diazaphospholidine-3,5-diones and Related Compounds: A Lecture on Unpredictability in Catalysis, Frank U. Richter, Chem. Eur. J. 2009, 15, pp. 5200-5202. D. Wendisch, H. Reiff and D. Dieterich, Die Angewandte Makromolekulare Chemie 141, 1986, 173-183 (Nr. 2302). Anhydrous Phosphazenium Fluorides as Sources for Extremely Reactive Fluoride Ions in Solution, Schwesinger, et al., Chem. Eur. J. 2006, 12, 438-445. An Electron-Rich Proazaphosphatrane for Isocyanate Trimerization to Isocyanurates, Raders, et al., J. Org. Chem. 2010, 75, 5308-5311. Extremely Base-Resistant Organic Phosphazenium Cations, Schwesinger, et al, Chem Eur. J. 2006, 12, 429-437. 

Primary Examiner - Michael L Leonard (74) Attorney, Agent, or Firm - Richard P. Bender; John E. Mrozinski, Jr. 

## (57) ABSTRACT 

The invention relates to a method for modifying isocyanates, wherein at least one organic monomer isocyanate having an NCO functionality > 1 is oligomerised in the presence of at least one catalyst, said method being characterised in that the catalyst comprises at least one specific compound having an NPN sequence selected from compounds of formula I (for› mula I), and/or from compounds of formula II (formula II) where HX represents an acid with a pKa value 2:2, x› represents the anion of an acid with a pKa value 2:2, and n represents an integer or fractional number between O and 20, wherein Y represents R$_{12}$(R$_{13}$)N- and/or one or more substituents of the structure of formula III (formula III) and wherein R$_{1 }$ to R$_{19 }$ independently represent identical or different substituents selected from C$_{1 }$-C$_{20 }$ alkyl-, C$_{1 }$-C$_{20 }$ cycloalkyl- and C$_{6}$-C$_{20 }$ aryl groups, or wherein R$_{1 }$ and R$_{2}$ , R$_{3 }$ and R$_{4}$ , R$_{5 }$ and R$_{6}$ , R$_{7 }$ and R$_{8}$ , R$_{9 }$ and R$_{10}$, R$_{12 }$and R$_{13}$, R$_{14 }$ and R$_{15}$, R 16 and R$_{1 7}$ , R$_{18 }$ and R$_{19 }$ independently represent identical or different substituents selected from C$_{1 }$-C$_{20 }$ alkylene-, C$_{1 }$-C$_{20 }$ cycloalkylene-, C$_{6}$-C$_{20 }$ arylene groups, and can form a 3- to 12-membered ring with the N atom joined to the P atom. The invention also relates to the use of a catalyst of this type. 

US010131736B2 

## FOREIGN PATENT DOCUMENTS 

(Continued) 

## OTHER PUBLICATIONS 

## 15 Claims, No Drawings 

