IP Library Granted Patent US 12,312,506
Granted Patent B2
US 12,312,506 · App. 17/999,522 · Granted May 27, 2025

Polymers for metal surface treatment

Inventors: Guillaume Gody (Rueil-Malmaison, FR); Isabelle Storet (Serezin de la Tour, FR); Laurent Garel (Lyons, FR); Marie-Pierre Labeau (Se'vres, FR)
Assignee: SPECIALTY OPERATIONS FRANCE
C09J5/04C08F2/10C08F212/24C08F220/06C09J5/02C09J2301/50C09J2400/166
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Quick Facts
Patent No.
US 12,312,506
App. No.
17/999,522
Granted
May 27, 2025
Kind
B2
Abstract

The instant invention concerns the use of polymers obtained by radical copolymerization of a mixture of (1) acrylic acid; (2) methacrylic acid; and (3) at least one allylcatechol selected from 4-allylbenzene-1,2-diol, 3-allylbenzene-1,2-diol; methylated forms thereof (eugenols); and mixtures thereof, for treating a metallic surface intended to be adhesive-bonded to another surface, in order to impart a resistance to the adhesive failure to the resulting bonding.

Claims (24)

1. A method of treating a first metallic surface (S1) intended to be bonded to a second surface (S2) by adhesive bonding, and for imparting a resistance to the adhesive failure to the bonding, comprising treating a first metallic surface (S1) with at least one polymer (P) obtained by radical copolymerization of a mixture of:

acrylic acid;

methacrylic acid; and

at least one methylated or not methylated allylcatechol which is selected from 4-allylbenzene-1,2-diol; 3-allylbezene-1,2-diol; corresponding eugenols; and mixtures thereof,

wherein the second surface (S2) is a metallic surface.

2. The method according to claim 1 , wherein treating the first metallic surface (S1) with at least one polymer (P) further imparts to the bonding a resistance to corrosive atmospheres and to wet atmospheres as measured by tensile tests defined in ASTM D-1002 10.

3. The method according to claim 1 , wherein the polymer (P) contains a mixture of two isomers 4-allylbenzene-1,2-diol and 3-allylbenzene-1,2-diol as the allylcatechol.

4. The method according to claim 1 , wherein the polymer (P) has a molecular weight between 10 and 150 kDa.

5. The method according to claim 1 , wherein the polymer (P) contains acrylic acid (AA) at a content of 10 to 90% in mol; methacrylic acid (MAA) at a content of 1 to 90% in mol, and allylcatechol at a content of 1 to 20% in mol, each molar ratio being calculated on the basis of a total quantity of AA, MAA and allylcatechol, with a ratio MAA/AA of more than 1/1.

6. The method according to claim 1 , wherein the first metallic surface (S1) is a surface comprising a metal selected from aluminum, steel, zinc, magnesium and their alloys.

7. The method according to claim 1 , wherein the polymer (P) is used for treating both surfaces (S1) and (S2) before the adhesive bonding of the two surfaces.

8. The method according to claim 7 , wherein the treatment of the surface (S1) and of the surface (S2) are followed by a rinsing step.

9. A process for bonding a first metallic surface (S1) with a second surface (S2) including:

treating the first surface (S1) with at least one composition including the at least one polymer (P) as defined in claim 1 ; and

optionally treating the second surface (S2) with at least one composition including the at least one polymer (P) in claim 1 ; and

bonding the surfaces (S1) and (S2) via an adhesive composition applied between the two surfaces.

10. The process according to claim 9 , wherein a composition comprising the polymer (P) is:

a conversion composition including a polymer (P); and/or

a solution or a dispersion of the polymer (P), applied on the surface after having applied a conversion coating on the surface to be treated; and/or

an adhesive composition, that comprise a polymer (P).

11. A material comprising two adhesive-bonded surfaces including a first metal surface comprising a metal surface (S1) which is in all or part (i) treated with a polymer (P) as defined in claim 1 and (ii) bonded to a second surface (S2) via an adhesive, the material being a material having a metal surface in all or part covered by:

at least one coating comprising the at least one polymer (P) as defined in claim 1 ; and/or

a layer comprising a reaction product of the polymer (P) as defined in claim 1 with a metal of the treated surface or another compound present in the layer, or the polymer (P) strongly linked with the other compound.

12. The method according to claim 3 , wherein a molar ratio of 4-allylbenzene-1,2-diol to 3-allylbenzene-1,2-diol between 30/70 and 70/30.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 12, 2024
From: GODY, GUILLAUME; STORET, ISABELLE; GAREL, LAURENT; LABEAU, MARIE-PIERRE
To: RHODIA OPERATIONS
Reel/Frame 066734/0684 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
Priority Claims (1)
EP 20305515 · May 19, 2020 · regional
Continuity (1)
Related Publication 20230203345A1 · Jun 29, 2023
References Cited (13)
US 4191596A · Dollman et al. · 1980 [cited by applicant]
US 4761189A · Mady et al. · 1988 [cited by applicant]
US 4921552A · Sander et al. · 1990 [cited by applicant]
US 5534082A · Dollman et al. · 1996 [cited by applicant]
US 12071495B2 · Labeau · 2024 [cited by examiner]
US 20130209812A1 · Gorodisher · 2013 [cited by examiner]
US 20210053379A1 · Elzer · 2021 [cited by examiner]
EP 0111897A1 · 1984 [cited by applicant]
EP 3659716A1 · 2020 [cited by applicant]
WO 9713588A1 · 1997 [cited by applicant]
WO 0038844A1 · 2000 [cited by applicant]
International Search Report issued in International Application No. PCT/EP2021/062297 dated Aug. 6, 2021 (3 pages). [cited by applicant]
Written Opinion issued in International Application No. PCT/EP2021/062297 dated Aug. 6, 2021 (7 pages). [cited by applicant]