Claims
- 1. A composition consisting essentially of a thermoplastic synthetic resin containing as the sole antistatic agent an antistatically effective amount of a compound having the formula ##STR51## where R and R.sup.1 are alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms, with the proviso that not over one of R and R.sup.1 can be hydrogen,
- R.sup.2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C.sub.2 to C.sub.6 aminoalkyl, C.sub.1 to C.sub.6 alkylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxyethylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxypropylamino C.sub.2 to C.sub.6 alkyl, or 2,3-dihydroxypropylamino C.sub.2 to C.sub.6 alkyl,
- R.sup.3 is hydrogen or alkyl of 1 to 5 carbon atoms,
- R.sup.4 is hydrogen or hydroxy, and
- X.sup.- is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group.
- 2. A composition according to claim 1 wherein R.sup.4 is hydroxy.
- 3. A composition according to claim 2 wherein R.sup.1 is hydrogen.
- 4. A composition according to claim 3 wherein R.sup.2 is hydrogen.
- 5. A composition according to claim 3 wherein R.sup.2 is alkyl of 1 to 5 carbon atoms.
- 6. A composition according to claim 5 wherein R.sup.3 is alkyl of 1 to 5 carbon atoms.
- 7. A composition according to claim 5 wherein R.sup.3 is hydrogen.
- 8. A composition according to claim 2 wherein R.sup.2 and R.sup.3 are hydrogen or alkyl of 1 to 2 carbon atoms.
- 9. A composition according to claim 2 wherein R.sup.2 is 2-hydroxyethyl, 2-hydroxypropyl, or 2,3-dihydroxypropyl.
- 10. A composition according to claim 2 wherein R.sup.2 is hydrogen, alkyl, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxyethylamino, 2-hydroxypropylamino, or 2,3-dihydroxypropylamino.
- 11. A composition according to claim 2 having formula I.
- 12. A composition according to claim 1 wherein R.sup.4 is hydrogen.
- 13. A composition according to claim 12 wherein R.sup.1 is hydrogen.
- 14. A composition according to claim 13 wherein R.sup.2 is hydrogen.
- 15. A composition according to claim 13 wherein R.sup.2 is alkyl of 1 to 5 carbon atoms.
- 16. A composition according to claim 15 wherein R.sup.3 is alkyl of 1 to 5 carbon atoms.
- 17. A composition according to claim 15 wherein R.sup.3 is hydrogen.
- 18. A composition according to claim 12 wherein R.sup.2 and R.sup.3 are hydrogen or alkyl of 1 to 2 carbon atoms.
- 19. A composition according to claim 12 wherein R.sup.2 is 2-hydroxyethyl, 2-hydroxypropyl, or 2,3-dihydroxypropyl.
- 20. A composition according to claim 12 wherein R.sup.2 is hydrogen, alkyl, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxyethylamino, 2-hydroxypropylamino, or 2,3-dihydroxypropylamino.
- 21. A composition according to claim 12 where the compound has formula I.
- 22. A composition according to claim 1 wherein the amount of antistatic agent is 0.01 to 20% based on the weight of the synthetic resin.
- 23. A composition according to claim 1 wherein the thermoplastic synthetic resin is a monoolefin polymer, polystyrene, polyvinyl chloride, polyvinyl acetate or a polymethacrylate.
- 24. A composition according to claim 23 wherein the polymer is polyethylene, polypropylene, ethylene-propylene copolymer, polystyrene, polyvinyl chloride, polyvinyl acetate or polymethyl methacrylate.
- 25. A composition according to claim 23 wherein the polymer is polyethylene or polypropylene.
- 26. A composition according to claim 1 including silica in an amount of 1 to 500 parts per 100 parts by weight of said compound of formula I or II.
- 27. A composition according to claim 26 wherein the silica is pyrogenic silica having a specific surface area between about 50 and 500 m.sup.2 /g measured according to BET and an average primary particle size below 500 nanometers.
- 28. A composition according to claim 27 containing 0.1 to 20 parts by weight of a compound of formula I or II homogenously distributed in 100 parts by weight of the thermoplastic synthetic resin.
- 29. A composition according to claim 28 containing 0.1 to 40 parts by weight of the silica.
- 30. A composition comprising a homogenous distribution of a compound having the formula ##STR52## where R and R.sup.1 are alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms, with the proviso that not over one of R and R.sup.1 can be hydrogen,
- R.sup.2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C.sub.2 to C.sub.6 aminoalkyl, C.sub.1 to C.sub.6 alkylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxyethylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxypropylamino C.sub.2 to C.sub.6 alkyl, or 2,3-dihydroxypropylamino C.sub.2 to C.sub.6 alkyl,
- R.sup.3 is hydrogen or alkyl of 1 to 5 carbon atoms,
- R.sup.4 is hydrogen or hydroxy, and
- X.sup.- is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group as the sole antistatic agent and silica in the amount of 1 to 500 parts per 100 parts of said compound.
- 31. A composition according to claim 30 including a thermoplastic synthetic resin, the amount of said compound of formula I or II being 0.1 to 20 parts per 100 parts of the synthetic resin.
- 32. A composition according to claim 30 consisting essentially of said compound of formula I or II and silica.
- 33. A composition according to claim 32 wherein the silica is pyrogenic silica having a specific surface area between about 50 and 500 m.sup.2 /g measured according to BET and an average primary particle size below 500 nanometers.
- 34. A composition according to claim 1 wherein the compound has formula I and where R.sup.4 is hydroxy, R and R.sup.1 are hydrogen or alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms, with the proviso that not over one of R and R.sup.1 can be hydrogen, R.sup.2 is 2,3-dihydroxypropyl, C.sub.2 to C.sub.6 aminoalkyl, C.sub.1 to C.sub.6 alkylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxyethylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxypropylamino C.sub.2 to C.sub.6 alkyl, or 2,3-dihydroxypropylamino C.sub.2 to C.sub.6 alkyl.
- 35. A compound according to claim 34 which is in the form of the free base.
- 36. A compound according to claim 35 wherein R.sup.1 is hydrogen.
- 37. A compound according to claim 35 wherein R.sup.2 is 2,3-dihydroxypropyl.
- 38. A compound according to claim 35 wherein R.sup.2 is 2,3-dihydroxypropyl, 2-hydroxyethylamino alkyl, 2-hydroxypropylamino alkyl, or 2,3-dihydroxypropylamino alkyl.
- 39. A composition according to claim 1 wherein the compound has formula I and where R.sup.4 is hydroxy, R and R.sup.1 are both alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms, R.sup.2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, C.sub.2 to C.sub.6 aminoalkyl, C.sub.1 to C.sub.6 alkylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxyethylamino C.sub.2 to C.sub.6 alkyl, 2-hydroxypropylamino C.sub.2 to C.sub.6 alkyl, or 2,3-dihydroxypropylamino C.sub.2 to C.sub.6 alkyl.
- 40. A composition according to claim 39 which is in the form of the free base.
- 41. A composition according to claim 40 wherein R.sup.2 is hydrogen.
- 42. A composition according to claim 40 wherein R.sup.2 is alkyl of 1 to 5 carbon atoms.
- 43. A composition according to claim 40 wherein R.sup.2 is 2-hydroxyethyl, 2-hydroxypropyl or 2,3-dihydroxypropyl.
- 44. A composition according to claim 40 wherein R.sup.2 is 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl.
- 45. A composition according to claim 40 wherein R.sup.2 is hydrogen, alkyl of 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl.
- 46. A composition according to claim 1 consisting of said synthetic resin and said compound of formula I or II.
- 47. A composition according to claim 22 consisting of said compound of formula I or II and silica.
- 48. A composition according to claim 22 consisting of said compound of formula I or II, silica and a thermoplastic synthetic resin.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2504054 |
Jan 1975 |
DEX |
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Parent Case Info
This is a continuation of application Ser. No. 653,834, filed Jan. 30, 1976, now U.S. Pat. No. 4,070,531.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3371130 |
Seifert |
Feb 1968 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
653834 |
Jan 1976 |
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