Composition for producing fuel resistant liquid polythioether polymers with good low temperature flexibility

{
  "publication_number": "US6232401B1",
  "country": "US",
  "kind": "B1",
  "title": "Composition for producing fuel resistant liquid polythioether polymers with good low temperature flexibility",
  "abstract": "A polythioether includes a structure having the formula I - R 1 - [- S - (CH 2) 2 - O - [- R 2 - O -] m - (CH 2) 2 - S - R 1 -] n - I wherein R 1 denotes a divalent C 2-6 n-alkyl, C 3-6 branched alkyl, C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, - [(- CH 2 -) p - X -] q - (- CH 2 -) r -, or - [(- CH 2 -) p - X -] q - (- CH 2 -) r - in which at least one - CH 2 - unit is substituted with a methyl group, R 2 denotes methylene, a divalent C 2-6 n-alkyl, C 2-6 branched alkyl, C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, or - [(- CH 2 -) p - X -] q - (- CH 2 -) r -, X denotes one selected from the group consisting of O, S and - NR 6, R 6 denotes H or methyl, m is a rational number from 0 to 10, n is an integer from 1 to 60, p is an integer from 2 to 6, q is an integer from 0 to 5, and r is an integer from 2 to 10. The polythioether is a liquid at room temperature and pressure.",
  "claims": [
    "1. A polymerizable composition comprising (i) about 30 to about 90 wt % of at least one polythioether, said at least one polythioether comprising a structure having the formula 1 - R 1 - [- S(CH 2) 2 - O - [- R 2 - O -] m - (CH 2) 2 - S - R 1 -] n 1 wherein R 1 denotes a divalent C 2-6 n-alkyl, C 3-6 branched alkyl, C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, - [(- CH 2 -) p - X -] q - (- CH 2 -) r -, or - [(- CH 2 -) p - X -] g - (- CH 2 -) r - in which at least one - CH 2 - unit is substituted with a methyl group, R 2 denotes methylene, a divalent C 2-6 n-alkyl, C 2-6 branched alkyl C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, or - [(- CH 2 -) p - X -] q - (- CH 2 -) r -, X is one selected from the group consisting of O, S and - NR 6 -. R 6 denotes H or methyl, m is a rational number from 0 to 10, n is an integer from 1 to 60, p is an integer from 2 to 6, q is an integer from 1 to 5, and r is an integer from 2 to 10, said at least one polythioether being a liquid at room temperature and pressure, said at least one polythioether having a glass transition temperature not higher than −55 C, (ii) a curing agent in an amount from about 90 to about 150% of stoichiometric based on the amount of at least one polythioether, and (iii) about 5 to about 60 wt % of a filler, with all wt % being based on the total weight of non-volatile components of the composition, wherein said composition is curable at a minimum temperature of 0 C.",
    "2. The polymerizable composition of claim 1 which has a glass transition temperature T g not higher than −60° C.",
    "3. The polymerizable composition of claim 1 which, when cured, has a percent volume swell not greater than 25% after immersion in JRF type 1 for one week at 60° C. and ambient pressure.",
    "4. The polymerizable composition of claim 1 further comprising an additive selected from the group consisting of a pigment in an amount from about 0.1 to about 10 wt %, a thixotrope in an amount from about 0.1 to about 5 wt %, an accelerator in an amount from about 0.1 to about 5 wt %, a retardant in an amount from about 0.1 to about 5 wt %, an adhesion promoter in an amount from about 0.1 to about 5 wt %, and a masking agent in an amount from about 0.1 to about 1 wt %.",
    "5. The polymerizable composition of claim 1 which comprises a mixture of at least two different polythioethers (i).",
    "6. A polymerizable composition comprising (i) about 30 to about 90 wt % of at least one polythioether, said at least one polythioether comprising a structure having the formula 1 - R 1 - [- S(CH 2) 2 - O - [- R 2 - O -] m - (CH 2) 2 - S - R 1 -] n - 1 wherein R 1 denotes a divalent C 2-6 n-alkyl, C 3-6 branched alkyl, C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, - [(- CH 2 -) p - X -] q - (- CH 2 r -, or - [(- CH 2 -) p - X -] q - (- CH 2 -) r - in which at least one - CH 2 - unit is substituted with a methyl group, R 2 denotes methylene, a divalent C 2-6 n-alkyl, C 2-6 branched alkyl, C 6-8 cycloalkyl or C 6-10 alkylcycloalkyl group, or - [(- CH 2 -) p - X -] q - (- CH 2 -) r -, X is one selected from the group consisting of O, S and - NR 6 -, R 6 denotes H or methyl, m is a rational number from 0 to 10, n is an integer from 1 to 60, p is an integer from 2 to 6, q is an integer from 1 to 5, and r is an integer from 2 to 10, said at least one polythioether being a liquid at room temperature and pressure, said at least one polythioether having a glass transition temperature not greater than −50 C, (ii) a curing agent in an amount from about 90 to about 150% of stoichiometric based on the amount of at least one polythioether, (iii) a plasticizer in an amount from about 1 to about 40 wt %, and (iv) about 5 to about 60 wt % of a filler, with all wt % being based on the total weight of non-volatile components of the composition, wherein said composition is curable at a minimum temperature of 0 C.",
    "7. The polymerizable composition of claim 6 which has a glass transition temperature T g not greater than −55° C.",
    "8. The polymerizable composition of claim 6 which, when cured, has a percent volume swell not greater than 25% after immersion for one week at room temperature and pressure.",
    "9. The polymerizable composition of claim 6 wherein said plasticizer is selected from the group consisting of phthalate esters, chlorinated paraffins and hydrogenated terphenyls.",
    "10. The polymerizable composition of claim 6 further comprising an additive selected from the group consisting of a pigment in an amount from about 0.1 to about 10 wt %, a thixotrope in an amount from about 0.1 to about 5 wt %, an accelerator in an amount from about 0.1 to about 5 wt %, a retardant in an amount from about 0.1 to about 5 wt %, an adhesion promoter in an amount from about 0.1 to about 5 wt %, and a masking agent in an amount from about 0.1 to about 1 wt %.",
    "11. The polymerizable composition of claim 6 which comprises a mixture of at least two different polythioethers (i)."
  ],
  "cpc": [
    "C08G 75/00",
    "C08G 75/02",
    "C08G 75/045",
    "C08G 75/12",
    "C08L 61/04",
    "C08L 61/06",
    "C08L 81/02"
  ],
  "assignees": [
    "PRC DESOTO INT INC"
  ],
  "filing_date": "1999-05-25",
  "publication_date": "2001-05-15",
  "grant_date": "2001-05-15",
  "priority_date": "1997-02-19",
  "application_number": "US-31850099-A",
  "family_id": "25182913",
  "citations": [
    "US3506626A",
    "US3697402A",
    "US3725229A",
    "US3734968A",
    "US4366307A",
    "US4609762A",
    "US5225472A",
    "US5516455A"
  ]
}