US 11,987,661 B2
Modified polymer polyols
César Muñoz De Diego, Móstoles (ES); Victoria Isabel Blasco Garcés, Móstoles (ES); and Olivier Lemoine, Rouen (FR)
Assigned to REPSOL, S.A., Madrid (ES)
Appl. No. 16/628,621
Filed by REPSOL, S.A., Madrid (ES)
PCT Filed Jul. 6, 2018, PCT No. PCT/EP2018/068391
§ 371(c)(1), (2) Date Jan. 3, 2020,
PCT Pub. No. WO2019/008140, PCT Pub. Date Jan. 10, 2019.
Claims priority of application No. 17382442 (EP), filed on Jul. 7, 2017.
Prior Publication US 2021/0130528 A1, May 6, 2021
Int. Cl. C08G 18/08 (2006.01); C08G 18/32 (2006.01); C08G 18/40 (2006.01); C08G 18/48 (2006.01); C08G 18/66 (2006.01); C08G 18/76 (2006.01); C08G 79/02 (2016.01); C08K 5/49 (2006.01); C09K 21/12 (2006.01)
CPC C08G 18/0876 (2013.01) [C08G 18/3275 (2013.01); C08G 18/409 (2013.01); C08G 18/4829 (2013.01); C08G 18/4841 (2013.01); C08G 18/6681 (2013.01); C08G 18/7621 (2013.01); C08G 79/02 (2013.01); C08K 5/49 (2013.01); C08G 2110/0083 (2021.01)] 15 Claims
 
1. A modified polymer polyol comprising at least one base polyol and a stable dispersion of polymeric particles in the at least one base polyol, the modified polymer polyol being obtainable by a process comprising the preparation of the polymeric particles in the presence of the at least one base polyol by a polycondensation reaction of
a) at least one compound bearing at least one basic-nitrogen atom characterized by the presence in the molecule of at least one hydrogen atom attached to a nitrogen atom; with
b) at least one compound bearing a phosphorous atom selected from the group consisting of b1) a compound bearing a phosphine group and b2) a condensation product from at least one compound of formula (I) or at least one compound of formula (II) and at least one compound bearing at least one basic nitrogen atom, wherein:
i) b1) the compound bearing a phosphine group is selected from the group consisting of at least one hydroxyalkylphosphine of formula (I), at least one hydroxyalkylphosphonium salt of formula (II), at least one hydroxyalkylphosphine oxide of formula (III) and a combination thereof;
and
ii) b2) the condensation product is at least one condensation product from at least one hydroxyalkylphosphine of formula (I) or at least one hydroxyalkylphosphonium salt of formula (II) and a) the least one compound bearing at least one basic-nitrogen atom characterized by the presence in the molecule of at least one hydrogen atom attached to a nitrogen atom;
wherein
A) the hydroxyalkylphosphine of formula (I) is as follows:

OG Complex Work Unit Chemistry
wherein R1, R2 and R3 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18arylalkyl, linear or branched hydroxy C1-C6 alkyl, C7-C18 alkylaryl and a radical of formula (IV)

OG Complex Work Unit Chemistry
wherein R5 and R6 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18arylalkyl, linear or branched hydroxy C1-C6 alkyl, and C7-C18 alkylaryl; and the wavy line means the attachment point of the radical of formula (IV) to the phosphorus atom;
with the proviso that at least one of R1, R2 and R3 is a radical of formula (IV);
B) the hydroxyalkylphosphonium salt of formula (II) is as follows:

OG Complex Work Unit Chemistry
wherein R1, R2, R3 and R4 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18 arylalkyl, linear or branched hydroxy C1-C6 alkyl, C7-C18 alkylaryl and a radical of formula (IV):

OG Complex Work Unit Chemistry
wherein R5 and R6 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18 arylalkyl, linear or branched hydroxy C1-C6 alkyl, and C7-C18 alkylaryl; and the wavy line means the attachment point of the radical of formula (IV) to the phosphorus atom; and X represents any anion suitable for compensate the positive charge of the phosphonium cation;
with the proviso that at least one of R1, R2, R3 and R4 is a radical of formula (IV); and
C) the hydroxyalkylphosphine oxide of formula (III) is as follows:

OG Complex Work Unit Chemistry
wherein R1, R2 and R3 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18arylalkyl, linear or branched hydroxy C1-C6 alkyl, C7-C18 alkylaryl and a radical of formula (IV):

OG Complex Work Unit Chemistry
wherein R5 and R6 are each independently selected from H, linear or branched C1-C18 alkyl, C3-C18 cycloalkyl, linear or branched C2-C18 alkenyl, C6-C18 aryl, C7-C18 arylalkyl, linear or branched hydroxy C1-C6 alkyl, and C7-C18 alkylaryl; and the wavy line means the attachment point of the radical of formula (IV) to the phosphorus atom;
with the proviso that at least one of R1, R2 and R3 is a radical of formula (IV);
and wherein the compound bearing at least one basic-nitrogen atom is selected from those compounds of formula (V) or formula (VI);
wherein the compounds of formula (V) are as follows
R7—NH2  (V)
wherein R7 is —H, —C1-C3 alkyl, C1-C3 alkyl-CO—, NH2—CO—, —(CH2)n—NH2, —CN, —NH2, —SO2NH2, cyclohexyl, phenyl, —SO2OH or —NHCONHNH2; wherein n is an integer from 1-18;
and the compounds of formula (VI) are as follows:

OG Complex Work Unit Chemistry
wherein R8 is selected from NH═C< and O═C<; S═C<; and R9 is selected from H, —CN, —NH2, —CONH2, —CONHCONH2, and —CONHCONHCONH2, wherein “<” indicates two single bonds that attach to either nitrogen atom in formula (VI).