Patent US4189550A successfully refreshed from Google Patents.
US4189550A
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US
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Antistatic agents for thermoplastic synthetic resins
Assignee: Henkel AG and Co KGaA
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Filing: 1977-07-27
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Granted: 1980-02-19
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Expires: 1997-07-27
Abstract
Abstract There are used as antistatic agents for thermoplastic synthetic resins compounds of the formulae ##STR1## where R and R' are saturated alkyl groups in which the sum of the carbon atoms in the two alkyl groups is 4 to 30 carbon atoms and wherein one of R and R' can be hydrogen, R 2 is hydrogen, lower alkyl with one to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl o-,m- and/or p-methylbenzyl, o-,m- and/or p-chlorobenzyl, o-,m- and/or p-bromobenzyl, aminoalkyl (C 2 to C 6 ), preferably aminoalkyl (C 2 and C 3 ), alkyl (C 1 to C 6 )-amino-alkyl (C 2 to C 6 ), 2-hydroxyethyl-aminoalkyl (C 2 to C 6 ), 2-hydroxypropyl-aminoalkyl (C 2 to C 6 ) or 2,3-dihydroxypropyl-aminoalkyl (C 2 to C 6 ), R 3 in case the compound is present as the ammonium salt is hydrogen or a lower alkyl group with 1 to 5 carbon atoms, R 4 is hydrogen or hydroxyl, and X - is a monovalent, inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group. The antistatic compounds can be premixed with silica to give enhanced antistatic activity.
Inventors
- 👤 Werner Schwarze
- 👤 Wolfgang Merk
- 👤 Volker Binder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:29
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/17; C08K5/19
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
167 words
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 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 1 can be hydrogen, R 2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen or hydroxy, and X - is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group.
Claim 2
Dependent Claim
167 words
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 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 1 can be hydrogen, R 2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen or hydroxy, and X - is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group.
Claim 3
Dependent Claim
11 words
A composition according to claim 1 wherein R 4 is hydroxy.
Claim 4
Dependent Claim
11 words
A composition according to claim 2 wherein R 1 is hydrogen.
Claim 5
Dependent Claim
11 words
A composition according to claim 3 wherein R 2 is hydrogen.
Claim 6
Dependent Claim
17 words
A composition according to claim 3 wherein R 2 is alkyl of 1 to 5 carbon atoms.
Claim 7
Dependent Claim
17 words
A composition according to claim 5 wherein R 3 is alkyl of 1 to 5 carbon atoms.
Claim 8
Dependent Claim
11 words
A composition according to claim 5 wherein R 3 is hydrogen.
Claim 9
Dependent Claim
22 words
A composition according to claim 2 wherein R 2 and R 3 are hydrogen or alkyl of 1 to 2 carbon atoms.
Claim 10
Dependent Claim
14 words
A composition according to claim 2 wherein R 2 is 2-hydroxyethyl, 2-hydroxypropyl, or 2,3-dihydroxypropyl.
Claim 11
Dependent Claim
19 words
A composition according to claim 2 wherein R 2 is hydrogen, alkyl, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxyethylamino, 2-hydroxypropylamino, or 2,3-dihydroxypropylamino.
Claim 12
Dependent Claim
9 words
A composition according to claim 2 having formula I.
Claim 13
Dependent Claim
11 words
A composition according to claim 1 wherein R 4 is hydrogen.
Claim 14
Dependent Claim
11 words
A composition according to claim 12 wherein R 1 is hydrogen.
Claim 15
Dependent Claim
11 words
A composition according to claim 13 wherein R 2 is hydrogen.
Claim 16
Dependent Claim
17 words
A composition according to claim 13 wherein R 2 is alkyl of 1 to 5 carbon atoms.
Claim 17
Dependent Claim
17 words
A composition according to claim 15 wherein R 3 is alkyl of 1 to 5 carbon atoms.
Claim 18
Dependent Claim
11 words
A composition according to claim 15 wherein R 3 is hydrogen.
Claim 19
Dependent Claim
22 words
A composition according to claim 12 wherein R 2 and R 3 are hydrogen or alkyl of 1 to 2 carbon atoms.
Claim 20
Dependent Claim
14 words
A composition according to claim 12 wherein R 2 is 2-hydroxyethyl, 2-hydroxypropyl, or 2,3-dihydroxypropyl.
Claim 21
Dependent Claim
19 words
A composition according to claim 12 wherein R 2 is hydrogen, alkyl, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, 2-hydroxyethylamino, 2-hydroxypropylamino, or 2,3-dihydroxypropylamino.
Claim 22
Dependent Claim
12 words
A composition according to claim 12 where the compound has formula I.
Claim 23
Dependent Claim
24 words
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.
Claim 24
Dependent Claim
23 words
A composition according to claim 1 wherein the thermoplastic synthetic resin is a monoolefin polymer, polystyrene, polyvinyl chloride, polyvinyl acetate or a polymethacrylate.
Claim 25
Dependent Claim
22 words
A composition according to claim 23 wherein the polymer is polyethylene, polypropylene, ethylene-propylene copolymer, polystyrene, polyvinyl chloride, polyvinyl acetate or polymethyl methacrylate.
Claim 26
Dependent Claim
13 words
A composition according to claim 23 wherein the polymer is polyethylene or polypropylene.
Claim 27
Dependent Claim
29 words
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.
Claim 28
Dependent Claim
38 words
A composition according to claim 26 wherein the silica is pyrogenic silica having a specific surface area between about 50 and 500 m 2 /g measured according to BET and an average primary particle size below 500 nanometers.
Claim 29
Dependent Claim
33 words
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.
Claim 30
Dependent Claim
16 words
A composition according to claim 28 containing 0.1 to 40 parts by weight of the silica.
Claim 31
Dependent Claim
175 words
A composition comprising a homogenous distribution of a compound having the formula ##STR52## where R and R 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 1 can be hydrogen, R 2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen or hydroxy, and X - 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.
Claim 32
Dependent Claim
175 words
A composition comprising a homogenous distribution of a compound having the formula ##STR52## where R and R 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 1 can be hydrogen, R 2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, benzyl, methylbenzyl, chlorobenzyl, bromobenzyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen or hydroxy, and X - 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.
Claim 33
Dependent Claim
33 words
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.
Claim 34
Dependent Claim
18 words
A composition according to claim 30 consisting essentially of said compound of formula I or II and silica.
Claim 35
Dependent Claim
38 words
A composition according to claim 32 wherein the silica is pyrogenic silica having a specific surface area between about 50 and 500 m 2 /g measured according to BET and an average primary particle size below 500 nanometers.
Claim 36
Dependent Claim
105 words
A composition according to claim 1 wherein the compound has formula I and where R 4 is hydroxy, R and R 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 1 can be hydrogen, R 2 is 2,3-dihydroxypropyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl.
Claim 37
Dependent Claim
15 words
A compound according to claim 34 which is in the form of the free base.
Claim 38
Dependent Claim
11 words
A compound according to claim 35 wherein R 1 is hydrogen.
Claim 39
Dependent Claim
11 words
A compound according to claim 35 wherein R 2 is 2,3-dihydroxypropyl.
Claim 40
Dependent Claim
18 words
A compound according to claim 35 wherein R 2 is 2,3-dihydroxypropyl, 2-hydroxyethylamino alkyl, 2-hydroxypropylamino alkyl, or 2,3-dihydroxypropylamino alkyl.
Claim 41
Dependent Claim
100 words
A composition according to claim 1 wherein the compound has formula I and where R 4 is hydroxy, R and R 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 2 is hydrogen, lower alkyl with 1 to 5 carbon atoms, 2-hydroxyethyl, 2-hydroxypropyl, 2,3-dihydroxypropyl, C 2 to C 6 aminoalkyl, C 1 to C 6 alkylamino C 2 to C 6 alkyl, 2-hydroxyethylamino C 2 to C 6 alkyl, 2-hydroxypropylamino C 2 to C 6 alkyl, or 2,3-dihydroxypropylamino C 2 to C 6 alkyl.
Claim 42
Dependent Claim
15 words
A composition according to claim 39 which is in the form of the free base.
Claim 43
Dependent Claim
11 words
A composition according to claim 40 wherein R 2 is hydrogen.
Claim 44
Dependent Claim
17 words
A composition according to claim 40 wherein R 2 is alkyl of 1 to 5 carbon atoms.
Claim 45
Dependent Claim
14 words
A composition according to claim 40 wherein R 2 is 2-hydroxyethyl, 2-hydroxypropyl or 2,3-dihydroxypropyl.
Claim 46
Dependent Claim
14 words
A composition according to claim 40 wherein R 2 is 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl.
Claim 47
Dependent Claim
25 words
A composition according to claim 40 wherein R 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.
Claim 48
Dependent Claim
19 words
A composition according to claim 1 consisting of said synthetic resin and said compound of formula I or II.
Claim 49
Dependent Claim
17 words
A composition according to claim 22 consisting of said compound of formula I or II and silica.
Claim 50
Dependent Claim
21 words
A composition according to claim 22 consisting of said compound of formula I or II, silica and a thermoplastic synthetic resin.
References Cited (Backward Citations)
US3371130A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-02-18 | 1983-08-20 | 1984-02-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-18 | 1987-08-20 | 1988-02-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-18 | 1991-08-20 | 1992-02-19 | $7700.00 | Window Closed / Lapsed |