Dual-cure method of forming industrial threads

• US 5,409,740 A
• Filed: 12/18/1992
• Issued: 04/25/1995
• Est. Priority Date: 12/18/1992
• Status: Expired due to Fees

• Current Assignee: Lord Corporation (Parker-Hannifin Corporation)
• Original Assignee: Lord Corporation (Parker-Hannifin Corporation)
• Inventors: Brann, Bill L.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US07/993,047
• Time in Patent Office: 858 Days
• Field of Search: 522/96, 522/90, 522/97, 522/100, 522/103, 522/104, 522/107, 522/182, 427/513, 428/395, 428/394
• US Class Current: 427/513
• CPC Class Codes: C08G 18/6725 containing ester groups other than acrylate or alkylacrylate ester groups
• CPC Class Codes: C09J 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: D02G 3/40 Yarns in which fibres are united by adhesives; Impregnated yarns or threads
• CPC Class Codes: D06M 14/18 using wave energy or particle radiation
• CPC Class Codes: D06M 14/26 on to materials of synthetic origin
• CPC Class Codes: D06M 15/564 Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
• CPC Class Codes: Y10T 428/2967 Synthetic resin or polymer
• CPC Class Codes: Y10T 428/2969 Polyamide, polyimide or polyester

Abstract

A method of forming a fiber bundle which is useful as an industrial thread. The fiber bundle is prepared by integrating individual fiber filaments into a fiber bundle, applying a dual-cure adhesive material to the fiber bundle and initiating polymerization of the dual-cure adhesive material. The dual-cure adhesive material is a combination of a radiation-curable material and a moisture-curable material. The radiation-curable material contains an acrylourethane oligomer and a reactive diluent system, while the moisture-curable material contains a polyisocyanate or an isocyanate-functional urethane prepolymer. The use of a dual-cure material results in a synergistic curing process so as to form a durable and flexible industrial thread or fiber.

Claims

1. A method of forming a fiber bundle comprising the steps of:

a) integrating a plurality of polymeric fiber filaments to form a fiber bundle;

b) forming a mixture of a radiation-curable material and a moisture-curable material as a dual-cure adhesive and applying said mixture to the fiber bundle to form a coated fiber bundle; and

c) initiating polymerization of the radiation-curable material by exposing the coated fiber bundle to a source of actinic radiation at a wavelength within the ultraviolet or visible spectral regions, and initiating polymerization of the moisture-curable material by moisture inherently present.

2. A method according to claim 1 wherein the fiber filaments are formed of a polymeric material selected from the group consisting of polyesters, acetates, polyacrylonitriles, and polyamides.

3. A method according to claim 1 wherein the fiber filaments are integrated by winding, weaving, spin extruding, or laying.

4. A method according to claim 1 wherein the radiation-curable material comprises an acrylate oligomer in combination with a reactive diluent system.

5. A method according to claim 4 wherein the acrylate oligomer is selected from the group consisting of acrylourethane oligomers, polyester acrylate oligomers, polyether acrylate oligomers and mixtures thereof.

6. A method according to claim 5 wherein the acrylourethane oligomer is prepared by reacting an olefinically unsaturated compound with an isocyanate-functional urethane formed by the reaction of an excess of a polyisocyanate with a polyol.

7. A method according to claim 6 wherein the olefinically unsaturated compound is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, N-hydroxymethyl acrylamide, N-hydroxymethyl methacrylamide, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, glycerine dimethacrylate, trimethylol propane dimethacrylate and reaction products of polyether glycols of acrylic or methacrylic acid.

8. A method according to claim 6 wherein the olefinically unsaturated compound is a lactone-acrylate adduct prepared by reacting an appropriate lactone with an acrylate or methacrylate acid ester.

9. A method according to claim 8 wherein the lactone acrylate adduct is a caprolactone-2-hydroxyethyl acrylate adduct.

10. A method according to claim 6 wherein the polyisocyanate is selected from the group consisting of alkyl, alkylene, cycloaklyl, cycloalkylene, aryl, and arylene polyisocyanates and combinations thereof.

11. A method according to claim 10 wherein the polyisocyanate is selected from the group consisting of toluene-2,4-diisocyanate, 2,2,4-trimethylhexamethylene-1,6-diisocyanate, hexamethylene-1,6-diisocyanate, diphenylmethane-4,4'"'"'-diisocyanate, triphenylmethane-4,4'"'"',4"-triisocyanate, polymethylene polyphenylisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate, naphthalene- 1,4-diisocyanate, diphenylene-4,4'"'"'-diisocyanate, 1,4-cyclohexylene dimethylene diisocyanate, xylene-1,4-diisocyanate, xylene- 1,3-diisocyanate, cyclohexyl- 1,4-diisocyanate, 4,4'"'"'-methylenebis(cyclohexyl isocyanate), 3,3'"'"'-dimethyldiphenylmethane-4,4'"'"'-diisocyanate, isophorone diisocyanate, m-tetramethyl xylene diisocyanate and the product obtained by reacting trimethylol propane and 2,4-toluene diisocyanate in a ratio of 1:

3.

12. A method according to claim 11 wherein the polyisocyanate is isophorone diisocyanate.

13. A method according to claim 6 wherein the polyol is a polyether, polyester, polycaprolactone, polyetherester polyol, or combination thereof.

14. A method according to claim 13 wherein the polyol is a polyester polyol prepared by the condensation of an excess of a polyol such as a diol, triol, or the like and an aliphatic, cycloaliphatic, or aromatic carboxylic acid or anhydride thereof having at least two carboxyl groups.

15. A method according to claim 4 wherein the reactive diluent system is selected from the group consisting of unsaturated addition-polymerizable monofunctional and polyfunctional acrylic monomers.

16. A method according to claim 15 wherein the monofunctional acrylic monomer is selected from the group consisting of isobornyl acrylate, phenoxyethyl acrylate, isodecyl acrylate, hexyl acrylate, cyclohexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, nonyl acrylate, stearyl acrylate, 2-phenoxy acrylate, 2-methoxyethyl acrylate, lactone modified esters of acrylic and methacrylic acid, methyl methacrylate, butyl acrylate, isobutyl acrylate, methacrylamide, allyl acrylate, tetrahydrofuryl acrylate, n-hexyl methacrylate, 2-(2-ethoxy-ethoxy)ethyl acrylate, n-lauryl acrylate, 2-phenoxyethyl acrylate, glycidyl methacrylate, glycidyl acrylate, acrylated methylolmelamine, and 2-(N,N-diethylamino)-ethyl acrylate;

and wherein the polyfunctional acrylic monomer is selected from the group consisting of neopentyl glycol diacrylate, alkoxylated neopentyl glycol diacrylate, ethylene glycol diacrylate, hexylene glycol diacrylate, diethylene glycol diacrylate, tripropylene glycol diacrylate, tetraethylene glycol diacrylate, pentaerythritol di-, tri-, tetra-, or penta-acrylate, trimethylolpropane triacrylate, alkoxylated trimethylolpropane triacrylate which contains from 2 to 14 moles of either ethylene or propylene oxide, triethylene glycol diacrylate, tetraethylene glycol diacrylate, polyethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, polyethylene glycol diacrylate, any corresponding methacrylates thereof, and combinations thereof.

17. A method according to claim 16 wherein the monofunctional acrylic monomer is isodecyl acrylate and the polyfunctional acrylic monomer is 1,6-hexanediol diacrylate.

18. A method according to claim 4 further comprising a photoinitiator.

19. A method according to claim 1 wherein the moisture-curable material comprises an isocyanate-functional compound.

20. A method according to claim 19 wherein the isocyanate-functional compound is a polyisocyanate or an isocyanate-functional urethane prepolymer.

21. A method according to claim 20 wherein the polyisocyanate is selected from the group consisting of alkyl, alkylene, cycloaklyl, cycloalkylene, aryl, and arylene polyisocyanates and combinations thereof.

22. A method according to claim 21 wherein the polyisocyanate is selected from the group consisting of toluene-2,4-diisocyanate, 2,2,4-trimethylhexamethylene-1,6-diisocyanate, hexamethylene- 1,6-diisocyanate, diphenylmethane-4,4'"'"'-diisocyanate, triphenylmethane-4,4'"'"',4"-triisocyanate, polymethylene polyphenylisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate, naphthalene- 1,4-diisocyanate, diphenylene-4,4'"'"'-diisocyanate, 1,4-cyclohexylene dimethylene diisocyanate, xylene-1,4-diisocyanate, xylene-1,3-diisocyanate, cyclohexyl-1,4-diisocyanate, 4,4'"'"'-methylenebis(cyclohexyl isocyanate), 3,3'"'"'-dimethyldiphenylmethane-4,4'"'"'-diisocyanate, isophorone diisocyanate, m-tetramethyl xylene diisocyanate and the product obtained by reacting trimethylol propane and 2,4-toluene diisocyanate in a ratio of 1:

3.

23. A method according to claim 19 wherein the isocyanate-functional compound is a polyfunctional aliphatic isocyanate based on hexamethylene-1,6-diisocyanate.

24. A method according to claim 20 wherein the isocyanate-functional urethane prepolymer is prepared by the reaction of an excess of a polyisocyanate with a polyol.

25. A method according to claim 24 wherein the polyisocyanate is selected from the group consisting of alkyl, alkylene, cycloaklyl, cycloalkylene, aryl, and arylene polyisocyanates and combinations thereof.

26. A method according to claim 24 wherein the polyol is selected from the group consisting of polyether, polyester, polycaprolactone, polyetherester polyols, and combination thereof.

27. A method according to claim 1 wherein the ratio of radiation-curable material to moisture-curable material ranges from about 9:

1 to 1;

1.

28. A method according to claim 27 wherein the ratio of radiation-curable material to moisture-curable material ranges from about 4:

1 to 1.5;

1.