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Patent · US9796858B2 · B2 · US

Thiolene-based compositions with extended pot life

(11) Publication number
US9796858B2
(21) Application number
15/263,412
(22) Filing date
2016-09-13
(30) Priority date
2015-03-12
(43) Publication date
2017-10-24
(45) Date of grant
2017-10-24
(52) CPC
  • C09D Coating compositions, e.g. paints, varnishes or lacquers; filling pastes; chemical paint or ink removers; inks; correcting fluids; woodstains; pastes or solids for colouring or printing; use of materials therefor: 5/086, 133/08, 175/14, 5/082
  • C08G Macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds: 75/045
  • C08K Use of inorganic or non-macromolecular organic substances as compounding ingredients: 5/37
(73) Assignee
PPG IND OHIO INC
(54) Title
Thiolene-based compositions with extended pot life
(57) Abstract

A method comprising (a) applying a composition to a substrate as a substantially continuous coating on the substrate, (b) curing the coating, wherein the composition comprises: (i) a polyene, (ii) a polythiol, (iii) 0.001 to 20 percent by weight of an anhydride, and (iv) up to 80 percent by weight of a pigment, particularly wherein the mole ratio of (ii) to (i) being from 0.1 to 10/1; the percentage by weight of (iii) being based on weight of resin solids in the composition and the percentage by weight of (iv) being based on solids weight of the composition.

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Claims (23)

  1. A method comprising: (a) applying a composition to a substrate as a substantially continuous coating on the substrate, (b) curing the compostion; wherein the curable composition comprises: (i) a polyene, (ii) a polythiol, (iii) 0.001 to 20 percent by weight of an anhydride, and (iv) up to 80 percent by weight of a pigment, wherein the mole ration of (ii) to (i) being from 0.1 to 10/1; the percentage by weight of (iii) being based on weight of resin solids in the composition and the percentage by weight of (iv) being based on solids weight of the composition.
  2. The method of claim 1 in which the composition is applied to the substrate by spraying.
  3. The method of claim 1 in which curing is done at temperatures of −10 to 80° C.
  4. The method of claim 1 in which the substrate is metal, plastic or a composite.
  5. The method of claim 1 in which the pigment is a corrosion-inhibiting pigment.
  6. The method of claim 1 in which the polyene has the structural formula A-(X) m where A is an organic moiety; X is an olefinically unsaturated moiety and m is at least 2.
  7. The method of claim 6 in which X is selected from - C(O)CHR═CH 2 and - CH 2 - CHR═CH 2, where R is hydrogen or methyl.
  8. The method of claim 6 in which A contains groups selected from ester and urethane.
  9. The method of claim 6 in which A is derived from a polyisocyanate.
  10. The method of claim 6 in which A-(X) m is a polyurethane (meth)acrylate.
  11. The method of claim 6 in which A-(X) m is a polyester (meth)acrylate.
  12. The method of claim 9 in which the polyisocyanate is an aliphatic including a cycloaliphatic polyisocyanate.
  13. The method of claim 6 in which m is from 2 to 6.
  14. The method of claim 1 in which the polythiol has the structural formula R 1 - (SH) n where R 1 is an organic moiety and n is at least 2.
  15. The method of claim 14 in which R 1 contains ester groups.
  16. The method of claim 14 in which R 1 is derived from a polyol.
  17. The method of claim 14 in which the polythiol is the reaction product of a thiol-functional organic acid and a polyol.
  18. The method of claim 14 in which n is from 2 to 6.
  19. The method of claim 1 in which the anhydride is an anhydride-containing polymer.
  20. The method of claim 19 in which the polymer is a (meth)acrylic polymer.
  21. The method of claim 1 wherein the curable composition further comprises a catalyst.
  22. The method of claim 21 in which the catalyst is a secondary or tertiary amine.
  23. The method of claim 21 in which the catalyst is present in the composition in amounts of 0.001 to 10 percent by weight based on weight of resin solids in the composition.

Citations (19)

  • CA2371636A1
  • EP0810251A2
  • GB1469935A
  • JPH059415A
  • JPH09255741A
  • US2005027082A1
  • US2009047442A1
  • US3898349A
  • US3908039A
  • US4076917A
  • US4097298A
  • US4374235A
  • US4425472A
  • US4698385A
  • US4767804A
  • US4908397A
  • US5236967A
  • US6639046B1
  • WO2008003498A1
Record as JSON
{
  "publication_number": "US9796858B2",
  "country": "US",
  "kind": "B2",
  "title": "Thiolene-based compositions with extended pot life",
  "abstract": "A method comprising (a) applying a composition to a substrate as a substantially continuous coating on the substrate, (b) curing the coating, wherein the composition comprises: (i) a polyene, (ii) a polythiol, (iii) 0.001 to 20 percent by weight of an anhydride, and (iv) up to 80 percent by weight of a pigment, particularly wherein the mole ratio of (ii) to (i) being from 0.1 to 10/1; the percentage by weight of (iii) being based on weight of resin solids in the composition and the percentage by weight of (iv) being based on solids weight of the composition.",
  "claims": [
    "1. A method comprising: (a) applying a composition to a substrate as a substantially continuous coating on the substrate, (b) curing the compostion; wherein the curable composition comprises: (i) a polyene, (ii) a polythiol, (iii) 0.001 to 20 percent by weight of an anhydride, and (iv) up to 80 percent by weight of a pigment, wherein the mole ration of (ii) to (i) being from 0.1 to 10/1; the percentage by weight of (iii) being based on weight of resin solids in the composition and the percentage by weight of (iv) being based on solids weight of the composition.",
    "2. The method of claim 1 in which the composition is applied to the substrate by spraying.",
    "3. The method of claim 1 in which curing is done at temperatures of −10 to 80° C.",
    "4. The method of claim 1 in which the substrate is metal, plastic or a composite.",
    "5. The method of claim 1 in which the pigment is a corrosion-inhibiting pigment.",
    "6. The method of claim 1 in which the polyene has the structural formula A-(X) m where A is an organic moiety; X is an olefinically unsaturated moiety and m is at least 2.",
    "7. The method of claim 6 in which X is selected from - C(O)CHR═CH 2 and - CH 2 - CHR═CH 2, where R is hydrogen or methyl.",
    "8. The method of claim 6 in which A contains groups selected from ester and urethane.",
    "9. The method of claim 6 in which A is derived from a polyisocyanate.",
    "10. The method of claim 6 in which A-(X) m is a polyurethane (meth)acrylate.",
    "11. The method of claim 6 in which A-(X) m is a polyester (meth)acrylate.",
    "12. The method of claim 9 in which the polyisocyanate is an aliphatic including a cycloaliphatic polyisocyanate.",
    "13. The method of claim 6 in which m is from 2 to 6.",
    "14. The method of claim 1 in which the polythiol has the structural formula R 1 - (SH) n where R 1 is an organic moiety and n is at least 2.",
    "15. The method of claim 14 in which R 1 contains ester groups.",
    "16. The method of claim 14 in which R 1 is derived from a polyol.",
    "17. The method of claim 14 in which the polythiol is the reaction product of a thiol-functional organic acid and a polyol.",
    "18. The method of claim 14 in which n is from 2 to 6.",
    "19. The method of claim 1 in which the anhydride is an anhydride-containing polymer.",
    "20. The method of claim 19 in which the polymer is a (meth)acrylic polymer.",
    "21. The method of claim 1 wherein the curable composition further comprises a catalyst.",
    "22. The method of claim 21 in which the catalyst is a secondary or tertiary amine.",
    "23. The method of claim 21 in which the catalyst is present in the composition in amounts of 0.001 to 10 percent by weight based on weight of resin solids in the composition."
  ],
  "cpc": [
    "C09D 5/086",
    "C08G 75/045",
    "C08K 5/37",
    "C09D 133/08",
    "C09D 175/14",
    "C09D 5/082"
  ],
  "assignees": [
    "PPG IND OHIO INC"
  ],
  "filing_date": "2016-09-13",
  "publication_date": "2017-10-24",
  "grant_date": "2017-10-24",
  "priority_date": "2015-03-12",
  "application_number": "US-201615263412-A",
  "family_id": "55650708",
  "citations": [
    "CA2371636A1",
    "EP0810251A2",
    "GB1469935A",
    "JPH059415A",
    "JPH09255741A",
    "US2005027082A1",
    "US2009047442A1",
    "US3898349A",
    "US3908039A",
    "US4076917A",
    "US4097298A",
    "US4374235A",
    "US4425472A",
    "US4698385A",
    "US4767804A",
    "US4908397A",
    "US5236967A",
    "US6639046B1",
    "WO2008003498A1"
  ]
}

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