Hardenable polymer composition

Patent metadata

Field	Value
Publication number	US-11098151-B2
Application number	US-201716340761-A
Country	US
Kind code	B2
Filing date	Oct 13, 2017
Priority date	Oct 14, 2016
Publication date	Aug 24, 2021
Grant date	Aug 24, 2021

Abstract

The present invention relates to a hardenable polymer composition containing at least one acrylate compound, at least one silyl-terminated polymer and at least one photoinitiator, to the use of the polymer composition as or in an adhesive, a sealant, gasket, knifing filler or coating composition, and to an adhesive composition, a sealant composition, a gasket composition, a knifing filler composition or a coating composition comprising the polymer composition.

First claim

We claim:

1. A hardenable polymer composition, comprising
(a) at least one acrylate compound;
(b) at least one silyl-terminated polymer; and
(c) at least one photoinitiator,
wherein the acrylate compound is an acrylate polymer containing an acrylic acid ester in polymerized form as main component of the polymer,
wherein the acrylate polymer is at least one selected from the group consisting of an acrylate polymer containing at least one functional group prone to photoinitiation;
wherein the functional group prone to photoinitiation is derived from a benzophenone group.

2. The polymer composition according to claim 1 , wherein the acrylate polymer containing a functional group prone to photoinitiation comprises
at least 60 mol-%, relative to 1 mol of the polymer, of repeating units of the following formula I:

where in a part of the repeating units radical R α is C 1 -C 10 -alkyl and in another part of the repeating units is a group of formula R α .1

where
# is an attachment point to the remainder of the molecule;
L is a bond or a spacer group of C 1 -C 8 -alkylene which is optionally bound to the phenyl ring via a linking group selected from the group consisting of —O—, —O—C(O)—, —C(O)—O—, —O—C(O)—O—, —NH—, —NH—C(O)—, —C(O)—NH—, —NH—C(O)—NH—, —O—C(O)—NH— and —NH—C(O)—O—;
Rγ is OH, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; and
m is 0, 1, 2, 3, 4 or 5; and
optionally repeating units of formulae II, III and/or IV:

where R α is independently as defined above.

3. The polymer composition according to claim 2 , wherein the acrylate polymer containing a functional group prone to photoinitiation comprises
from 80 to 99.9 mol-% of repeating units of the formula I wherein R α is C 1 -C 10 -alkyl;
from 0.01 to 20 mol-% of repeating units of the formula I wherein R α is a benzophenone group of formula R α .1; and
from 0 to 15 mol-% of repeating units of formula III;
relative to 1 mol of the polymer,
wherein the mol percentages of repeating units of the formula I wherein R α is C 1 -C 10 -alkyl, repeating units of the formula I wherein R α is a benzophenone group, and repeating units of the formula III essentially sum up to 100 mol-%.

4. The polymer composition according to claim 1 , wherein the acrylate compound has a weight average molecular weight of more than 30000.

5. The polymer composition according to claim 1 , wherein the silyl-terminated polymer is a polymer of formula I
[(R′) a (R″O) 3-a Si-L 1 -Y] b -Po  (I)

where
Po is a di-, tri- or tetravalent radical of a base polymer;
each Y is independently selected from the group consisting of a bond, —NH—C(═O)—O—, —O—C(═O)—NH—, —C(═O)—NH—L 2 -NH—C(═O)—NH—, —NH—C(═O)—NH—L 2 -NH—C(═O)—, —O—C(═O)—, —C(═O)—O—, —NH—C(═O)—S—, —S—C(═O)—NH—and —O—;
R′ and R″, independently of each other and independently of each occurrence, are C 1 -C 6 -alkyl;
L 1 is C 1 -C 3 -alkylene;
L 2 is a divalent aliphatic, cycloaliphatic or aromatic radical;
each a is independently 0 or 1; and
b is 2, 3 or 4.

6. The polymer composition according to claim 5 , wherein Po is the di-, tri- or tetravalent radical of a polymer selected from the group consisting of a polyether, a polyester, a polyamide, a polyimine, a polyurethane, a poly(meth)acrylate, a polyvinylester, a polyolefin and a mixture thereof.

7. The polymer composition according to claim 6 , wherein Po is the divalent radical of a polyether.

8. The polymer composition according to claim 5 , wherein
Y is —NH—C(═O)—O—;
R′ and R″, independently of each other and independently of each occurrence, are methyl or ethyl; and
each L 1 is independently —CH 2 — or C 3 -alkylene.

9. The polymer composition according to claim 1 , wherein the at least one photoinitiator is a photolatent initiator which becomes active with UV C radiation, UV B radiation, UV A radiation and/or radiation in the visible range; a photoinitiator which is not photolatent and which becomes active with UV C radiation; or a mixture of said photolatent latent initiator and said photoinitiator which becomes active with UV C radiation.

10. The polymer composition according to claim 9 , wherein the at least one photoinitiator is a photolatent initiator or a mixture of a photolatent latent initiator and a photoinitiator which is not photolatent and which becomes active with UV C radiation.

11. The polymer composition according to claim 9 , wherein the at least one photoinitiator is a photolatent initiator, which is selected from the group consisting of a photolatent base, a photolatent acid generator and a photolatent metal-based initiator.

12. The polymer composition according to claim 11 , wherein the photolatent initiator is
a photolatent base, which is a B a —Z a compound, where B a and Z a are covalently bound, and where B a is derived from a base selected from the group consisting of an amidine, a guanidine and a secondary amine, and Z a is a photolytically removable group; or
a photolatent acid generator, which is a A b -Z b compound, where A b and Z b are covalently bound, and where A b is derived from an acid selected from the group consisting of an aliphatic sulfonic acid and an aromatic sulfonic acid, and Z b is a photolytically removable group; or an acylphosphine oxides; or an ionic photoacid generator; or
a metal-based initiator, which is a titanium complex containing at least one photolytically removable ligand.

13. The polymer composition according to claim 12 , wherein the photolatent initiator is a photolatent base, which is a compound of formulae PLB.1 to PLB.7:

where
each R 18 is independently C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl or C 1 -C 6 -alkoxycarbonyl;
R 19 is hydrogen or C 1 -C 4 -alkyl; and
s is 0, 1, 2, 3, 4 or 5.

14. The polymer composition according to claim 13 , wherein the photolatent base is a compound of formula PLB.1, PLB.2, PLB.4, PLB.5, PLB.6 or PLB.7.

15. The polymer composition according to claim 12 , wherein the photolatent initiator is a photolatent acid generator, which is an acylphosphine oxide of formula PAG.2

where
R 22 is C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy or phenyl which optionally comprises 1, 2, 3, 4 or 5 substituents selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy;
R 23 is C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy, C(O)R 25 or phenyl which optionally comprises 1, 2, 3, 4 or 5 substituents selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy;
R 24 is C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy;
R 25 is C 1 -C 10 -alkyl, C 1 -C 10 -alkoxy or phenyl which optionally comprises 1, 2, 3, 4 or 5 substituents selected from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; and
q is 0, 1, 2, 3, 4 or 5.

16. The polymer composition according to claim 1 , containing:
(a) at least one acrylate compound: 1 to 98% by weight;
(b) at least one silyl-terminated poly

Assignees

• Basf Se

Inventors

• Hoevel Bernd
• Roser Angelika
• Pfister Juergen
• Christ Thomas

Classifications

• C09J153/00

  Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers · CPC title

• C09D153/00

  Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers · CPC title

• C08F299/024 Primary

  the unsaturation being in acrylic or methacrylic groups · CPC title

• C09J2301/416

  use of irradiation · CPC title

• C09J133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title