Granted Patent B2

US 12,466,981 · App. 18/005,377 · Granted Nov 11, 2025

Inventors: Patxi Garra (Barcelona, ES); Marta Rodriguez Ble (Barcelona, ES); Jordi Solera Sendra (Barcelona, ES); Marc Escriba Pla (Barcelona, ES)

Assignee: BOSTIK SA

C09J133/08

Abstract

Claims (69)

1 . A two-part curable composition, characterized in that it comprises:

a) a first part (part A) comprising:

i. at least 50 wt. % of one or more cyanoacrylate monomer(s),

ii. at least 1 wt. % of one or more (meth)acrylic monomer(s), and

iii. at least 1 wt. % of a per-compound,

wherein the wt. % is based on the total weight of the first part of the composition,

b) a second part (part B) comprising:

i. at least 50 wt. % of a non-reactive diluent, and

ii. from 0.001 wt. % to 2 wt. % of a transition metal catalyst, expressed as the content of the transition metal,

wherein the wt. % is based on the total weight of the second part of the composition, wherein the volume ratio between the first part and the second part ranges from 4:1 to 10:1, with the proviso that the second part does not comprise any vinylic monomer(s).

2 . The two-part curable composition according to claim 1 , characterized in that the (meth)acrylic monomer(s) of Part A of the two-part curable composition is selected from the group consisting of:

i. a compound of general formula (III)

CH 2 ═CR 3 (CO 2 R 4 )  (III)

wherein R 3 represents methyl or H, and R 4 is a hydrogen atom, a C 1 -C 8 linear or branched alkyl, a C 2 -C 6 linear or branched alkoxyalkyl, a furfuryl or an isobornyl group;

ii. polyfunctional (meth)acrylic esters, and

iii. mixtures thereof.

3 . The two-part curable composition according to claim 1 , characterized in that the first part of the composition further contains one or more additives selected from the group consisting of stabilizing agents, adhesion promoters, accelerating agents, thixotropic agents, thickening agents, toughening agents, plasticizers, antioxidants, pigments, colorants, and mixtures thereof.

4 . The two-part curable composition according to claim 3 , characterized in that the first part of the composition comprises one or more stabilizing agents selected from the group consisting of radical stabilizing agents, acid stabilizing agents, and mixtures thereof.

5 . The two-part curable composition according to claim 1 , characterized in that the non-reactive diluent is a plasticizer.

6 . The two-part curable composition according to claim 1 , characterized in that the transition metal catalyst is a transition metal salt.

7 . The two-part curable composition according to claim 6 , characterized in that the transition metal salt is selected from the group consisting of Cu(ACN) 4 BF 4 , Cu(ACN) 4 PF 6 , Cu(BF 4 ) 2 , Cu (II) acetate, CU (II) octoate, Cu(II) benzoate, Cu (II) chlorate, Cu (II) carbonate, Cu(II) acetylacetonate, Cu (I) trifluoromethanesulfonate, Cu (II) sulfate, Fe (II) triflate, ferrocene, Fe (II) tetrafluorobotare, MnClO 4 , Co naphtenate, and Co tetrafluoroborate.

8 . The two-part curable composition according to claim 1 , characterized in that the second part of the composition comprises an electron rich initiating species for cyanoacrylates.

9 . The two-part curable composition according to claim 1 , characterized in that the (meth)acrylic monomer(s) of Part A of the two-part curable composition is selected from the group consisting of:

a compound of general formula (III)

CH 2 ═CR 3 (CO 2 R 4 )  (III)

wherein R 3 represents methyl or H, and R 4 is a hydrogen atom, a C 1 -C 8 linear or branched alkyl, a C 2 -C 6 linear or branched alkoxyalkyl, a furfuryl or an isobornyl group;

a polyfunctional (meth)acrylic ester selected from the group consisting of butanediol di(meth)acrylate, hexanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, triethylene oxide dimethacrylate, tris-(2-hydroxyethyl) isocyanurate triacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane tri(meth)acrylate (TMPTA), ethoxylated trimethylolpropane tri(meth)acrylate, neopentylglycol diacrylate, pentaerythritol tetraacrylate (PETA), pentaerythritol tetramethacrylate (PETMA), dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol-A-diacrylate, bisphenol-A-dimethacrylate, ethoxylated bisphenol-A-diacrylate, propoxylated bisphenol-A-diacrylate, and mixtures thereof; (meth)acrylic functionalized oligomers and (meth)acrylic functionalized resins; and

mixtures thereof.

10 . The two-part curable composition according to claim 1 , characterized in that the (meth)acrylic monomer(s) of Part A of the two-part curable composition is selected from the group consisting of:

a compound of general formula (III)

CH 2 ═CR 3 (CO 2 R 4 )  (III)

wherein R 3 represents methyl or H, and R 4 is a hydrogen atom, a C 1 -C 8 linear or branched alkyl, a C 2 -C 6 linear or branched alkoxyalkyl, a furfuryl or an isobornyl group;

a polyfunctional (meth)acrylic ester selected from the group consisting of butanediol di(meth)acrylate, hexanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, triethylene oxide dimethacrylate, tris-(2-hydroxyethyl) isocyanurate triacrylate, tricyclodecane dimethanol diacrylate, trimethylolpropane tri(meth)acrylate (TMPTA), ethoxylated trimethylolpropane tri(meth)acrylate, neopentylglycol diacrylate, pentaerythritol tetraacrylate (PETA), pentaerythritol tetramethacrylate (PETMA), dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol-A-diacrylate, bisphenol-A-dimethacrylate, ethoxylated bisphenol-A-diacrylate, propoxylated bisphenol-A-diacrylate, and mixtures thereof; and

mixtures thereof.

11 . The two-part curable composition according to claim 1 , characterized in that it comprises:

a) a first part (Part A) comprising:

i. from 50 wt. % to 99 wt. % of one or more cyanoacrylate monomer(s),

ii. at least 1 wt. % of one or more (meth)acrylic monomer(s), and

iii. at least 1 wt. % of a per-compound,

wherein the wt. % is based on the total weight of the first part of the composition,

b) a second part (Part B) comprising:

i. from 50 wt. % to 99.9 wt. %, of a non-reactive diluent, and

ii. from 0.001 wt. % to 2 wt. % of a transition metal catalyst, expressed as the content of the transition metal,

wherein the wt. % is based on the total weight of the second part of the composition, wherein the volume ratio between the first part and the second part ranges from 4:1 to 10:1, with the proviso that the second part does not comprise any vinylic monomer(s).

12 . The two-part curable composition according to claim 1 , characterized in that it comprises:

a) a first part (Part A) comprising:

i. at least 50 wt. % of one or more cyanoacrylate monomer(s);

ii. from 1 wt. % to 10 wt. % of a (meth)acrylate monomer or monomers;

iii. from 1 wt. % to 10 wt. % of a per-compound;

iv. from 0.001 wt. % to 0.2 wt. % of stabilizing agent(s);

v. from 2 wt. % to 10 wt. % by weight of thixotropic agent(s); and

vi. from 2 wt. % to 10 wt. % by weight of thickening agent(s);

wherein the wt. % is based on the total weight of the first part of the composition,

b) a second part (Part B) comprising:

i. at least 50 wt. % of at least one non-reactive diluent;

ii. from 0.001 wt. % to 2 wt. % of a transition metal catalyst, expressed as the content of the transition metal,

iii. from 0.1 wt. % to 2 wt. % of an electron rich initiator compound;

iv. from 2 wt. % to 15 wt. % of thickening agent(s); and

v. from 2 wt. % to 8 wt. % of thixotropic agent(s);

wherein the wt. % is based on the total weight of the second part of the composition, wherein the volume ratio between the first part and the second part ranges from 4:1 to 10:1, with the proviso that the second part does not comprise any vinylic monomer(s).

13 . A syringe or a cartridge comprising the two-part curable cyanoacrylate composition of claim 1 .

14 . A method for bonding substrates, characterized in that it comprises the steps of:

1) mixing together the two-part curable composition of claim 1 ,

2) applying the mix of Step 1) to at least one of the substrates, and

3) mating together the substrates for a time sufficient to permit an adhesive bond to form between the mated substrates.

15 . A repair method for filling depressions, cracks or holes in a substrate or between substrates, characterized in that it comprises the steps of:

1) mixing together the two-part curable composition of claim 1 ,

2) applying the mix of Step 1) into a depression, crack or hole of a substrate or on the upper part of a substrate, and optionally,

3) assembling a second substrate atop the first substrate.

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (21)