US 11,987,663 B2
Polyurethane-organopolysiloxanes having carbodiimide groups
Alexander Höflich, Tübingen (DE); Robert Zyschka, Wannwell (DE); Andreas Troscheit, Pliezhausen (DE); Matthias Bauer, Ehningen (DE); and Silke Wezel, Reutlingen (DE)
Assigned to CHT Germany GmbH, Tübingen (DE)
Appl. No. 15/734,776
Filed by CHT Germany GmbH, Tübingen (DE)
PCT Filed May 27, 2019, PCT No. PCT/EP2019/063618
§ 371(c)(1), (2) Date Dec. 3, 2020,
PCT Pub. No. WO2019/242997, PCT Pub. Date Dec. 26, 2019.
Claims priority of application No. 10 2018 114 549.7 (DE), filed on Jun. 18, 2018.
Prior Publication US 2021/0230348 A1, Jul. 29, 2021
Int. Cl. C08G 18/79 (2006.01); C08G 18/12 (2006.01); C08G 18/50 (2006.01); C08G 18/61 (2006.01); C08L 75/04 (2006.01); D06B 1/00 (2006.01); D06M 15/564 (2006.01)
CPC C08G 18/797 (2013.01) [C08G 18/12 (2013.01); C08G 18/5096 (2013.01); C08G 18/61 (2013.01); C08L 75/04 (2013.01); D06B 1/00 (2013.01); D06M 15/564 (2013.01)] 14 Claims
 
1. Polyurethane/polyorganosiloxane and/or polyurea-polyorganosiloxane compounds and salts thereof that contain at least one structural element of formula [II]

OG Complex Work Unit Chemistry
and Ri is a structural element of formula [III]

OG Complex Work Unit Chemistry
in which V has the structure [V]:

OG Complex Work Unit Chemistry
in which n=0 to 10, and X is derived from aromatic, cycloaliphatic or aliphatic, at least divalent, linear or branched mono- or polyisocyanates and their mixtures of isomers and/or mixtures of different diisocyanates having up to 15 carbon atoms that were subjected to a carbodiimidation reaction, wherein said reaction yields a compound of formula [XII]:

OG Complex Work Unit Chemistry
wherein —V— is as defined above, and x≥2;
P1 is derived from polyols or polyamines adhering to formula (XIII) where P1 is a polymer moiety selected from the group consisting of a polycarbonate, polyester, polyether, polyacrylate, polyolefin, polydimethylsiloxane, polylactone, polyamides, polyurea, polyurethane, copolymers thereof, and mixtures of such polymers, terminated with hydroxyl- or amine groups:

OG Complex Work Unit Chemistry
wherein g≥1, and Y=—NRA— or —O—, and RA represents hydrogen or a linear, branched, cyclic, saturated, unsaturated or aromatic hydrocarbyl radical with up to 20 carbon atoms, which may additionally contain several groups selected from —O—, —C(O)—, —NH—, tertiary amines, or quaternary ammonium compounds;
P2 is derived from an α,ω-primary or secondary amino- or hydroxyalkyl- or hydroxypolyetheralkyl-functionalized polyorganosiloxane having the structure

OG Complex Work Unit Chemistry
in which s=2 to 500 and s′=1 to 3, D and D′ are primary or secondary hydroxy- or aminoalkyl- or hydroxypolyether-terminated organic radicals having up to 200 carbon atoms, which is capable of undergoing a chemical polyaddition reaction with [XII], D and D′ are additionally the same or different, and Rx is a linear, branched, cyclic, saturated, unsaturated, aromatic, substituted or unsubstituted hydrocarbyl radical having up to 20 carbon atoms, which may additionally bear amino or quaternary ammonium compounds or hydroxyalkyl or hydroxypolyetheralkyl groups, whereby P may provide a comb-like structure, P2 is selected independently of P1;
P3 is a linear, branched, cyclic, saturated, unsaturated, aromatic, substituted, or unsubstituted group with up to 20 carbon atoms, which is converted to its salts by a protonatable or deprotonatable group -J-, to enable the polymer to achieve water solubility, emulsifiability and/or dispersibility, where, x, y, and z are all integers ≥1;
and a chain extender —U— selected from aliphatic, monovalent, divalent or polyvalent, linear or branched polyols or polyamines with up to 15 carbon atoms, or from primary or secondary amino- or hydroxy-terminated polyethers with a molecular weight of up to 1000 g/mol.