IP Library Granted Patent US 12,630,676
Granted Patent B2
US 12,630,676 · App. 17/905,776 · Granted May 19, 2026

Silylated sealing composition with improved adhesion on metallic substrates

Inventor: Yichen Cao (Shanghai, CN)
Assignee: BOSTIK SA
C08G77/02C08L83/02C08G2150/00C08G2170/00
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Quick Facts
Patent No.
US 12,630,676
App. No.
17/905,776
Granted
May 19, 2026
Kind
B2
Abstract

A moisture curable silylated composition comprising: a polymer (A) comprising at least 2 alkoxysilyl terminal groups of formula (I): wherein R 1 represents a hydrocarbon-based divalent radical comprising from 5 to 15 carbon atoms; R 2 represents a C 2 -C 4 alkylene; R 3 represents a C 1 -C 6 alkylene; R 4 and R 5 each represent a C 1 -C 4 alkyl; R 6 represents H or a radical comprising 1 to 6 carbon atoms; n is an integer such that Mw of the block of formula —[OR 2 ] n — is 300 to 40000 g/mole; m is an integer different from 0 such that the Mw of the polymer (A) is between 500 to 50000 g/mole, and p is an integer equal to 0, 1 or 2; a polymer (B) comprising at least 2 alkoxysilyl terminal groups of formula (II): wherein R 2 , R 4 , R 5 , n and p are such as defined for formula (I); and an alkoxy modified silsesquioxane (C).

Claims (47)

1 . Moisture curable silylated composition comprising, on the basis of the total weight of said composition:

from 35 to 65% by weight of a polymer (A) comprising at least 2 alkoxysilyl terminal groups of formula (I):

wherein

R 1 represents a hydrocarbon-based divalent radical comprising from 5 to 15 carbon atoms which may be aromatic or aliphatic, linear, branched or cyclic,

R 2 represents a linear or branched alkylene divalent radical comprising from 2 to 4 carbon atoms,

R 3 represents a linear or branched alkylene divalent radical comprising from 1 to 6 carbon atoms,

R 4 and R 5 , which are identical or different, each represent a linear or branched alkyl radical having 1 to 4 carbon atoms, with the possibility, when there are several R 4 (or R 5 ) radicals, that these are identical or different,

R 6 represents a hydrogen atom or a radical comprising 1 to 6 carbon atoms which may be aromatic or aliphatic, linear, branched or cyclic, or a radical selected among the radicals:

of formula (Ia):

 of formula (Ib):

or

 of formula (Ic):

wherein R 7 is linear or branched alkyl radical comprising from 1 to 6 carbon atoms;

n is an integer such that the average molecular weight of the polyether block of formula —[OR 2 ] n — is between 300 g/mole and 40000 g/mole,

m is an integer different from 0 such that the average molecular weight of the polymer (A) is between 500 g/mole and 50000 g/mole, and

p is an integer equal to 0, 1 or 2;

from 2.5 to 12% by weight of a polymer (B) comprising at least 2 alkoxysilyl terminal groups of formula (II)

wherein R 2 , R 4 , R 5 , n and p are such as defined for formula (I); and

from 7.5 to 28% by weight of an alkoxy modified silsesquioxane (C), and

from about 10 to 20% by weight of a polyether (D) which comprises only one alkoxysilyl terminal group linked to the main polyether chain by a divalent group:—O—CO—NH—(CH 2 ) 3 — in which —(CH 2 ) 3 — is directly linked to the Si atom of the alkoxysilyl terminal group.

2 . Moisture curable silylated composition according to claim 1 , wherein polymer (A) is such that:

R 1 is chosen from one of the following divalent radicals, the formulae of which below show the 2 free valences:

a) the divalent radical derived from isophorone diisocyanate (IPDI):

 b) the divalent radical derived from methylenebis(cyclohexyl isocyanate) (HMDI):

 c) the divalent radical derived from tolylene diisocyanate (TDI):

 d) the divalent radical derived from diphenylmethane diisocyanate (MDI):

 e) the divalent radical derived from hexamethylene diisocyanate (HDI):

—(CH 2 ) 6 —;

 f) the radical divalent derived from m-xylylene diisocyanate (XDI):

R 2 is the ethylene and/or isopropylene divalent radical;

R 3 is the methylene and/or n-propylene divalent radical; and

R 4 and R 5 each represent the methyl or ethyl radical; and

R 6 represents a hydrogen atom; a phenyl radical; or a linear, branched or cyclic alkyl radical comprising from 1 to 6 carbon atoms.

3 . Moisture curable silylated composition according to claim 1 , wherein polymer (B) is such that in formula (II) R 2 is an isopropylene divalent radical and R 4 and R 5 are each a methyl or an ethyl.

4 . Moisture curable silylated composition according to claim 1 , wherein the alkoxy modified silsesquioxane (C) is of formula (III):

wherein R′ 1 to R′ 8 are the same and different and represent:

a hydrogen atom,

a radical selected among a linear or branched C 1 -C 4 alkoxy, a linear or branched alkyl comprising from 1 to 30 carbon atoms, an alkenyl comprising from 2 to 30 carbon atoms, an aromatic radical comprising from 6 to 30 carbon atoms, an allyl radical comprising from 3 to 30 carbon atoms, a cyclic aliphatic radical comprising from 3 to 30 carbon atoms, an acyl radical comprising from 1 to 30 carbon atoms; or

a —OSiR′ 9 R′ 10 group in which R′ 9 and R′ 10 represent a hydrogen atom, or a radical selected among a linear or branched C 1 -C 4 alkyl, a linear or branched C 1 -C 4 alkoxy, a C 2 -C 4 alkenyl, a phenyl, a C 3 -C 6 allyl radical, a C 3 -C 8 cyclic aliphatic radical, a C 1 -C 4 acyl radical;

provided that at least one of R′ 1 to R′ 8 is a C 1 -C 4 alkoxy radical.

5 . Moisture curable silylated composition according to claim 4 , wherein R′ 1 to R′ 8 in formula (III) represent a radical selected from the group consisting of methyl, methoxy and phenyl, provided that at least one of R′ 1 to R′ 8 is a methoxy.

6 . Moisture curable silylated composition according to claim 1 , wherein it comprises polymer (B) and silsesquioxane (C) in weight % quantity such that the weight ratio (B)/[(B)+(C)] lies in the range from 10 to 35%.

7 . Moisture curable silylated composition according to claim 1 , wherein it comprises:

from 40 to 60% by weight of polymer (A);

from 3.7 to 10.5% by weight of polymer (B); and

from 11.3 to 24.5% by weight of silsesquioxane (C).

8 . An adhesive, sealant and/or coating material comprising the moisture curable silylated composition as defined in claim 1 .

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 30, 2025
From: BOSTIK SA
To: BOSTIK SA
Reel/Frame 072277/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 7, 2022
From: CAO, YICHEN
To: BOSTIK SA
Reel/Frame 061010/0426 →
Priority Claims (1)
EP 20161825 · Mar 9, 2020 · regional
Continuity (1)
Related Publication 20240191034A1 · Jun 13, 2024
References Cited (13)
US 20110151253A1 · Laferte et al. · 2011 [cited by applicant]
US 20190315917A1 · Stanjek · 2019 [cited by examiner]
US 20200095377A1 · Sanz et al. · 2020 [cited by applicant]
US 20200317853A1 · Li · 2020 [cited by examiner]
EP 1657155A1 · 2006 [cited by applicant]
EP 2336208A1 · 2011 [cited by applicant]
FR 3066765A1 · 2018 [cited by applicant]
WO 2008107331A1 · 2008 [cited by applicant]
WO 2013136108A1 · 2013 [cited by applicant]
WO 2014031568A1 · 2014 [cited by applicant]
WO 2016174009A1 · 2016 [cited by applicant]
WO WO2019126246A1 · 2019 [cited by examiner]
ISA/EP; International Search Report and Written Opinion for International Patent Application No. PCT/EP2021/054984 dated May 17, 2021, 10 pages. [cited by applicant]