IP Library › Granted Patent US 12,722,358
Granted Patent B2
US 12,722,358 · App. 18/173,373 · Granted Sep 1, 2026

Adhesive bonding composition and method of use

Inventors: Zakaryae Fathi (Raleigh, NC); Frederic A. Bourke, Jr. (Aspen, CO); Harold Walder (Oak Island, NC)
Assignee: Immunolight, LLC
B32B7/12B32B5/02B32B5/18B32B5/26B32B7/06B32B9/025B32B9/04B32B9/043B32B17/00B32B18/00B32B21/042B32B25/045B32B27/08B32B27/16B32B27/302B32B27/304B32B27/308B32B27/32B32B27/322B32B27/34B32B27/36B32B37/12B32B38/0008C09J7/10C09J11/06C09J133/00C09J133/06H10W72/00B32B2037/1253B32B2255/26B32B2305/18B32B2307/202B32B2307/204B32B2307/21B32B2307/3065B32B2307/41B32B2307/412B32B2307/422B32B2307/50B32B2307/546B32B2307/548B32B2307/552B32B2307/706B32B2307/72B32B2307/748B32B2307/75B32B2310/0806B32B2439/00B32B2439/70B32B2439/80B32B2457/14B32B2479/00B32B2605/003B32B2605/08H10W72/01323H10W72/01325H10W72/01333H10W72/01336H10W72/01351H10W72/01355H10W72/01951H10W72/01953H10W72/0198H10W72/07311H10W72/07338H10W72/074H10W72/322H10W72/325H10W72/352H10W72/353H10W72/354H10W72/59H10W72/925H10W72/953H10W90/732H10W90/734H10W90/736
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Quick Facts
Patent No.
US 12,722,358
App. No.
18/173,373
Granted
Sep 1, 2026
Kind
B2
Abstract

A method of and system for adhesive bonding by a) providing a polymerizable adhesive composition on a surface of an element to be bonded to form an assembly; b) irradiating the assembly with radiation at a first wavelength capable of vulcanization of bonds in the polymerizable adhesive composition by activation of sulfur-containing compound with at least one selected from x-ray, e-beam, visible, or infrared light to thereby generate ultraviolet light in the polymerizable adhesive composition; and c) adhesively joining two or more components together by way of the polymerizable adhesive composition, and a curable polymer for use therein.

Claims (79)

1 . A method of adhesive bonding, comprising:

a) providing an adherent structure including one or more rubber compounds on a surface of an element to be bonded, wherein providing an adherent structure comprises modifying said surface of the element to be bonded to increase a surface energy thereof;

b) placing a polymerizable adhesive composition, including at least one photoinitiator and at least one energy converting material, in contact with the adherent structure and two or more components to be bonded to form an assembly;

c) irradiating the assembly with radiation at a first wavelength, capable of conversion by the at least one energy converting material to a second wavelength capable of activating the at least one photoinitiator to produce from the polymerizable adhesive composition a cured adhesive composition; and

d) adhesively joining the two or more components by way of the adherent structure and the cured adhesive composition.

2 . The method of claim 1 , wherein said at least one energy converting material is a downconverting material.

3 . The method of claim 2 , wherein said downconverting material comprises inorganic particulates selected from the group consisting of:

metal oxides; metal sulfides; doped metal oxides; and mixed metal chalcogenides.

4 . The method of claim 2 , wherein said downconverting material comprises at least one of Y 2 O 3 , Y 2 O 2 S, NaYF 4 , NaYbF 4 , YAG, YAP, Nd 2 O 3 , LaF 3 , LaCl 3 , La 2 O 3 , TiO 2 , LuPO 4 , YVO 4 , YbF 3 , YF 3 , Na-doped YbF 3 , ZnS; ZnSe; MgS; CaS; ZnSe x S y ; ZnSe x S y :Cu, Ag, Ce, Tb; and alkali lead silicate including compositions of SiO 2 , B 2 O 3 , Na 2 O, K 2 O, PbO, MgO, or Ag, and combinations or alloys or layers thereof.

5 . The method of claim 4 , wherein the downconverting material comprises a dopant including at least one of Er, Eu, Yb, Tm, Nd, Mn Tb, Ce, Y, U, Pr, La, Gd and other rare-earth species or a combination thereof.

6 . The method of claim 2 , wherein the downconverting material comprises at least one of CaS, ZnSeS, and iron sulfate.

7 . The method of claim 2 , wherein said first wavelength of radiation is at least one of X-rays, electron beams, and UV light.

8 . The method of claim 1 , wherein said at least one energy converting material comprises an upconverting material.

9 . The method of claim 8 , wherein said first wavelength of radiation is near infrared.

10 . The method of claim 8 , wherein said upconverting material comprises at least one of Y 2 O 3 , Y 2 O 2 S, NaYF 4 , NaYbF 4 , YAG, YAP, Nd 2 O 3 , LaF 3 , LaCl 3 , La 2 O 3 , TiO 2 , LuPO 4 , YVO 4 , YbF 3 , YF 3 , Na-doped YbF 3 , or SiO 2 or alloys or layers thereof.

11 . The method of claim 1 , wherein said polymerizable adhesive composition comprises a monomer forming a thermoset resin.

12 . The method of claim 1 , further comprising adding a peroxide to the polymerizable adhesive composition.

13 . The method of claim 1 , wherein said at least one photoinitiator is selected from the group consisting of: benzoin ethers, benzil ketals, α-dialkoxyacetophenones, α-aminoalkylphenones, acylphosphine oxides, benzophenones/amines, thioxanthones/amines, and titanocenes.

14 . The method of claim 1 , wherein said polymerizable adhesive composition comprises inorganic particulates selected from the group consisting of: metals and metal alloys, ceramics and dielectrics, and metal-coated polymers.

15 . The method of claim 14 , wherein said polymerizable adhesive composition comprises an organic component selected from the group consisting of: solvents, viscosity modifiers, surfactants, dispersants, and plasticizers.

16 . The method of claim 1 , wherein providing an adherent structure comprises:

providing a solution containing natural or synthetic rubber compounds on said surface of the element to be bonded;

removing said solvent;

polymerizing said rubber compounds.

17 . The method of claim 16 , wherein the polymerization comprises exposing the rubber compounds to at least one of x-rays, e-beam, or UV flux.

18 . The method of claim 17 , wherein the exposing comprises breaking double bonds in the rubber compounds followed by bonding of the rubber compounds to the surface of the element to be bonded.

19 . The method of claim 16 , wherein the solution is provided with a concentration of the natural or synthetic rubber compounds between 33% and 45%.

20 . The method of claim 1 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 50 mJ/m 2 .

21 . The method of claim 1 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 40 mJ/m 2 .

22 . The method of claim 1 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 30 mJ/m 2 .

23 . The method of claim 1 , wherein the surface of the element to be bonded comprises at least one of a polytetrafluoroethylene, a poly(perfluoroalkylacrylate), a polystyrene, a polyacrylate, a poly(methyl methacrylate), a poly(dimethylsiloxane), a polyethylene, a polychlorotrifluoroethylene, a polypropylene, a polyvinyl chloride, a polyvinyl fluoride, a polyvinylidenedichloride, a polyvinylidenedifluoride, a polyacrylamide, a polyethylene terephthalate, a poly(6-aminocoproicacid), and a poly(11-aminoundecaroicacid).

24 . The method of claim 1 , wherein the surface of the element to be bonded comprises at least one of a silicone and a poly(dimethyl siloxane).

25 . The method of claim 1 , wherein modifying comprises exposing said surface to a plasma treatment.

26 . The method of claim 1 , wherein modifying comprises exposing said surface to a plasma treatment at atmospheric pressure conditions.

27 . The method of claim 1 , wherein modifying comprises exposing said surface to a chemical etchant.

28 . The method of claim 1 , wherein said at least one energy converting material comprises an organic phosphor.

29 . The method of claim 28 , wherein the at least one photoinitiator is configured to be activated by emitted light from one or more of organic phosphors.

30 . The method of claim 28 , wherein the organic phosphor comprises at least one of anthracene, sulfoflavine, fluorescein, eosin, polyvinyltoluene, styrene, fluors, and rhodamine.

31 . The method of claim 28 , wherein the organic phosphor is linked to the at least one photoinitiator.

32 . A method of adhesive bonding, comprising:

a) providing an adherent structure including one or more rubber compounds on a surface of an element to be bonded, wherein providing an adherent structure comprises applying a primer to said surface of the element to be bonded;

b) placing a polymerizable adhesive composition, including at least one photoinitiator and at least one energy converting material, in contact with the adherent structure and two or more components to be bonded to form an assembly;

c) irradiating the assembly with radiation at a first wavelength, capable of conversion by the at least one energy converting material to a second wavelength capable of activating the at least one photoinitiator to produce from the polymerizable adhesive composition a cured adhesive composition; and

d) adhesively joining the two or more components by way of the adherent structure and the cured adhesive composition, wherein providing an adherent structure comprises applying a primer to said surface of the element to be bonded.

33 . The method of claim 32 , wherein the primer comprises a two-component urethane-based primer.

34 . The method of claim 33 , wherein the two-component urethane-based primer comprises a moisture activated primer.

35 . The method of claim 32 , wherein said at least one energy converting material is a downconverting material.

36 . The method of claim 35 , wherein said downconverting material comprises inorganic particulates selected from the group consisting of:

metal oxides; metal sulfides; doped metal oxides; and mixed metal chalcogenides.

37 . The method of claim 35 , wherein said downconverting material comprises at least one of Y 2 O 3 , Y 2 O 2 S, NaYF 4 , NaYbF 4 , YAG, YAP, Nd 2 O 3 , LaF 3 , LaCl 3 , La 2 O 3 , TiO 2 , LuPO 4 , YVO 4 , YbF 3 , YF 3 , Na-doped YbF 3 , ZnS; ZnSe; MgS; CaS; ZnSe x S y ; ZnSe x S y :Cu, Ag, Ce, Tb; and alkali lead silicate including compositions of SiO 2 , B 2 O 3 , Na 2 O, K 2 O, PbO, MgO, or Ag, and combinations or alloys or layers thereof.

38 . The method of claim 37 , wherein the downconverting material comprises a dopant including at least one of Er, Eu, Yb, Tm, Nd, Mn Tb, Ce, Y, U, Pr, La, Gd and other rare-earth species or a combination thereof.

39 . The method of claim 35 , wherein the downconverting material comprises at least one of CaS, ZnSeS, and iron sulfate.

40 . The method of claim 35 , wherein said first wavelength of radiation is at least one of X-rays, electron beams, and UV light.

41 . The method of claim 32 , wherein said at least one energy converting material comprises an upconverting material.

42 . The method of claim 41 , wherein said first wavelength of radiation is near infrared.

43 . The method of claim 41 , wherein said upconverting material comprises at least one of Y 2 O 3 , Y 2 O 2 S, NaYF 4 , NaYbF 4 , YAG, YAP, Nd 2 O 3 , LaF 3 , LaCl 3 , La 2 O 3 , TiO 2 , LuPO 4 , YVO 4 , YbF 3 , YF 3 , Na-doped YbF 3 , or SiO 2 or alloys or layers thereof.

44 . The method of claim 32 , wherein said polymerizable adhesive composition comprises a monomer forming a thermoset resin.

45 . The method of claim 32 , further comprising adding a peroxide to the polymerizable adhesive composition.

46 . The method of claim 32 , wherein said at least one photoinitiator is selected from the group consisting of: benzoin ethers, benzil ketals, α-dialkoxyacetophenones, α-aminoalkylphenones, acylphosphine oxides, benzophenones/amines, thioxanthones/amines, and titanocenes.

47 . The method of claim 32 , wherein said polymerizable adhesive composition comprises inorganic particulates selected from the group consisting of: metals and metal alloys, ceramics and dielectrics, and metal-coated polymers.

48 . The method of claim 47 , wherein said polymerizable adhesive composition comprises an organic component selected from the group consisting of: solvents, viscosity modifiers, surfactants, dispersants, and plasticizers.

49 . The method of claim 32 , wherein providing an adherent structure comprises:

providing a solution containing natural or synthetic rubber compounds on said surface of the element to be bonded;

removing said solvent;

polymerizing said rubber compounds.

50 . The method of claim 49 , wherein the polymerization comprises exposing the rubber compounds to at least one of x-rays, e-beam, or UV flux.

51 . The method of claim 50 , wherein the exposing comprises breaking double bonds in the rubber compounds followed by bonding of the rubber compounds to the surface of the element to be bonded.

52 . The method of claim 49 , wherein the solution is provided with a concentration of the natural or synthetic rubber compounds between 33% and 45%.

53 . The method of claim 32 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 50 mJ/m 2 .

54 . The method of claim 32 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 40 mJ/m 2 .

55 . The method of claim 32 , wherein the surface of the element to be bonded comprises a low energy material having a surface energy of less than 30 mJ/m 2 .

56 . The method of claim 32 , wherein the surface of the element to be bonded comprises at least one of a polytetrafluoroethylene, a poly(perfluoroalkylacrylate), a polystyrene, a polyacrylate, a poly(methyl methacrylate), a poly(dimethylsiloxane), a polyethylene, a polychlorotrifluoroethylene, a polypropylene, a polyvinyl chloride, a polyvinyl fluoride, a polyvinylidenedichloride, a polyvinylidenedifluoride, a polyacrylamide, a polyethylene terephthalate, a poly(6-aminocoproicacid), and a poly(11-aminoundecaroicacid).

57 . The method of claim 32 , wherein the surface of the element to be bonded comprises at least one of a silicone and a poly(dimethyl siloxane).

58 . The method of claim 32 , wherein modifying comprises exposing said surface to a plasma treatment.

59 . The method of claim 32 , wherein modifying comprises exposing said surface to a plasma treatment at atmospheric pressure conditions.

60 . The method of claim 32 , wherein modifying comprises exposing said surface to a chemical etchant.

61 . The method of claim 32 , wherein said at least one energy converting material comprises an organic phosphor.

62 . The method of claim 61 , wherein the at least one photoinitiator is configured to be activated by emitted light from one or more of organic phosphors.

63 . The method of claim 61 , wherein the organic phosphor comprises at least one of anthracene, sulfoflavine, fluorescein, eosin, polyvinyltoluene, styrene, fluors, and rhodamine.

Continuity (5)
Continuation 16944877 · Jul 31, 2020
Continuation 16515754 · Jul 18, 2019
Continuation 15322928 · Jun 29, 2015
Provisional Application 62018915 · Jun 30, 2014
Related Publication 20230191747A1 · Jun 22, 2023
References Cited (44)
US 2388373A · Stewart · 1945 [cited by applicant]
US 4929401A · Shippen · 1990 [cited by applicant]
US 5939206A · Kneezel · 1999 [cited by applicant]
US 7032492B2 · Meshirer · 2006 [cited by applicant]
US 7943235B2 · Yamamoto et al. · 2011 [cited by applicant]
US 20020000037A1 · Chou · 2002 [cited by applicant]
US 20020011306A1 · Hannington · 2002 [cited by applicant]
US 20020101004A1 · Farris · 2002 [cited by applicant]
US 20020105567A1 · Yamada · 2002 [cited by applicant]
US 20030124357A1 · Kagerer · 2003 [cited by applicant]
US 20030226472A1 · Kneafsey · 2003 [cited by applicant]
US 20050064182A1 · Lunsford · 2005 [cited by applicant]
US 20050084640A1 · Bilodeau · 2005 [cited by applicant]
US 20050233547A1 · Noda · 2005 [cited by applicant]
US 20080122067A1 · Wang · 2008 [cited by applicant]
US 20090027872A1 · Debije · 2009 [cited by applicant]
US 20100173167A1 · Vissing · 2010 [cited by applicant]
US 20100261263A1 · Vo-Dinh · 2010 [cited by applicant]
US 20100279491A1 · Kiuchi · 2010 [cited by applicant]
US 20110127445A1 · Zhang · 2011 [cited by applicant]
US 20120089180A1 · Fathi et al. · 2012 [cited by applicant]
US 20120201973A1 · Guo · 2012 [cited by applicant]
US 20130011608A1 · Wolk · 2013 [cited by applicant]
US 20130203895A1 · Dershem · 2013 [cited by applicant]
US 20130288062A1 · Van Loon et al. · 2013 [cited by applicant]
US 20140113078A1 · Aberle et al. · 2014 [cited by applicant]
US 20140248496A1 · Kuwajima · 2014 [cited by applicant]
US 20150182321A1 · Karazivan · 2015 [cited by applicant]
US 20150184031A1 · Yurt · 2015 [cited by applicant]
US 20150210783A1 · Youngbull · 2015 [cited by applicant]
US 20150246521A1 · Fathi et al. · 2015 [cited by applicant]
US 20160024358A1 · Zambova · 2016 [cited by applicant]
US 20170162537A1 · Fathi et al. · 2017 [cited by applicant]
US 20170186720A1 · Fathi et al. · 2017 [cited by applicant]
KR 20030088660 · 2003 [cited by applicant]
WO WO2011140469A1 · 2011 [cited by applicant]
WO WO2015143065A1 · 2015 [cited by applicant]
Office Action issued Jul. 15, 2020 in corresponding European Patent Application No. 15 814 784.3, 5 pages. [cited by applicant]
Office Action issued Mar. 1, 2021 in corresponding European Patent Application No. 15 814 784.3, 10 pages. [cited by applicant]
International Search Report and Written Opinion of the International Searching Authority issued Sep. 24, 2015 in PCT/US2015/038290 filed Jun. 29, 2015. [cited by applicant]
International Preliminary Report on Patentability and Written Opinion of the International Searching Authority issued Jan. 12, 2017 in PCT/US2015/038290 filed Jun. 29, 2015. [cited by applicant]
Partial Supplementary European Search Report issued Oct. 30, 2017 in Patent Application No. 15814784.3. [cited by applicant]
Extended European Search Report issued Feb. 9, 2018 in European Patent Application No. 15814784.3. [cited by applicant]
European Office Action issued Feb. 27, 2018 in European Patent Application No. 15814784.3. [cited by applicant]