US 11,702,611 B2
Associative and exchangeable oligomers, and composition containing same
Gregory Descroix, Brindas (FR); and Fanny Briand, Lyons (FR)
Assigned to TOTAL MARKETING SERVICES, Puteaux (FR)
Appl. No. 17/58,349
Filed by TOTAL MARKETING SERVICES, Puteaux (FR)
PCT Filed May 23, 2019, PCT No. PCT/FR2019/051188
§ 371(c)(1), (2) Date Nov. 24, 2020,
PCT Pub. No. WO2019/224491, PCT Pub. Date Nov. 28, 2019.
Claims priority of application No. 1854406 (FR), filed on May 24, 2018.
Prior Publication US 2021/0309930 A1, Oct. 7, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C10M 145/00 (2006.01); C10M 157/10 (2006.01); C10M 145/14 (2006.01); C10M 155/04 (2006.01); C10M 169/04 (2006.01); C10N 20/04 (2006.01); C10N 40/25 (2006.01)
CPC C10M 157/10 (2013.01) [C10M 145/14 (2013.01); C10M 155/04 (2013.01); C10M 169/041 (2013.01); C10M 2203/003 (2013.01); C10M 2209/084 (2013.01); C10M 2229/00 (2013.01); C10N 2020/04 (2013.01); C10N 2040/25 (2013.01)] 20 Claims
OG exemplary drawing
 
1. A composition comprising a mixture of at least
a polydiol oligomer A1 with a number-average molar mass of from 600 g/mol to 8,000 g/mol, comprising repeating units corresponding to:
at least two monomers M1, and
at least one monomer M2, or
at least one monomer M3, or
at least one monomer M2 and at least one monomer M3, and
a compound A2 comprising at least two boronic ester functions, which is an oligomer with a number-average molar mass of from 600 g/mol to 7,100 g/mol, comprising repeating units which correspond to:
at least two monomers M4,
optionally at least one monomer M5, and
optionally at least one monomer M3,
wherein
the monomer M1 corresponds to the general formula (I):

OG Complex Work Unit Chemistry
in which:
R1 is selected from the group consisting of —H, —CH3 and —CH2—CH3;
x is an integer ranging from 1 to 18;
y is an integer equal to 0 or 1;
X1 and X2, which may be identical or different, are selected from the group consisting of hydrogen, tetrahydropyranyl, methyloxymethyl, tert-butyl, benzyl, trimethylsilyl and t-butyldimethylsilyl; or
X1 and X2 form, with the oxygen atoms directly attached to each of —OX1 and —OX2, a bridge having the following formula

OG Complex Work Unit Chemistry
in which:
the asterisks (*) symbolize the bonds to the oxygen atoms,
R′2 and R″2, which may be identical or different, are selected from the group consisting of hydrogen and a C1-C11 alkyl; or
X1 and X2 form, with the oxygen atoms directly attached to each of —OX1 and —OX2, a boronic ester having the following formula:

OG Complex Work Unit Chemistry
in which:
the asterisks (*) symbolize the bonds to the oxygen atoms,
R′″2 is selected from the group consisting of a C6-C30 aryl, a C7-C30 aralkyl and a C2-C30 alkyl;
the monomer M2 corresponds to the general formula (II):

OG Complex Work Unit Chemistry
in which:
R2 is selected from the group consisting of —H, —CH3 and —CH2—CH3;
R3 is selected from the group consisting of: —C(O)—O—R′3; —O—R′3; —S—R′3 and —C(O)—N(H)—R′3 with R′3 a C1-C30 alkyl group,
the monomer M3 corresponds to the general formula (X):

OG Complex Work Unit Chemistry
in which:
Z1, Z2 and Z3, which may be identical or different, represent groups selected from the group consisting of a hydrogen atom, a C1-C12 alkyl, and a group —OZ′ or —C(O)—O—Z′ with Z′ being a C1-C12 alkyl,
the monomer M4 corresponds to the formula (IV):

OG Complex Work Unit Chemistry
in which:
t is an integer equal to 0 or 1;
u is an integer equal to 0 or 1;
M and R8 are identical or different divalent bonding groups, selected from the group consisting of a C6-C18 aryl, a C7-C24 aralkyl and a C2-C24 alkyl,
X is a function selected from the group consisting of —O—C(O)—, —C(O)—O—, —C(O)—N(H)—, —N(H)—C(O)—, —S—, —N(R′4)— and —O— with R′4 being a hydrocarbon-based chain comprising from 1 to 15 carbon atoms;
R9 is selected from the group consisting of —H, —CH3 and —CH2—CH3;
R10 and R11, which may be identical or different, represent a group selected from the group consisting of a hydrogen atom, and a hydrocarbon-based group comprising from 1 to 30 carbon atoms, optionally substituted with one or more groups selected from the group consisting of: a hydroxyl, and a group —OJ or —C(O)—O-J with J being a hydrocarbon-based group comprising from 1 to 24 carbon atoms; and
the monomer M5 corresponds to the formula (V):

OG Complex Work Unit Chemistry
(V)
in which:
R12 is selected from the group consisting of —H, —CH3 and —CH2—CH3,
R13 is selected from the group consisting of —C(O)—O—R′13; —O—R′13, —S—R′13 and —C(O)—N(H)—R′13, with R′13 being a C1-C30 alkyl group.