US4070531A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antistatic agents for thermoplastic synthetic resins
Assignee: Henkel AG and Co KGaA
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Filing: 1976-01-30
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Granted: 1978-01-24
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Expires: 1996-01-30
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 )-aminoalkyl (C 2 to C 6 ), 2-hydroxyethyl-aminoalkyl (C 1 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
2026-10-24 03:30
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/17; C08K5/19; Y; Y10; Y10S; Y10S260/00; Y10S260/15; Y10S260/19; Y10S260/20
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
106 words
A composition comprising a thermoplastic synthetic resin containing 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 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is 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
106 words
A composition comprising a thermoplastic synthetic resin containing 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 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is 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
160 words
A composition comprising a thermoplastic synthetic resin containing an antistatically effective amount 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.
Claim 4
Dependent Claim
160 words
A composition comprising a thermoplastic synthetic resin containing an antistatically effective amount 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.
Claim 5
Dependent Claim
11 words
A composition according to claim 2 where R 4 is hydroxy.
Claim 6
Dependent Claim
11 words
A composition according to claim 2 where R 4 is hydrogen.
Claim 7
Dependent Claim
106 words
A composition comprising a thermoplastic synthetic resin containing an antistatically effective amount of a compound having the formula ##STR53## 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 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen, and X - is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group.
Claim 8
Dependent Claim
106 words
A composition comprising a thermoplastic synthetic resin containing an antistatically effective amount of a compound having the formula ##STR53## 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 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl, R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, R 4 is hydrogen, and X - is a monovalent inorganic or organic acid group or one equivalent of a polybasic inorganic or organic acid group.
Claim 9
Dependent Claim
167 words
A composition comprising a thermoplastic synthetic resin which is polyvinyl chloride or polymethyl methacrylate containing an antistatically effective amount of a compound having the formula ##STR54## 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 10
Dependent Claim
167 words
A composition comprising a thermoplastic synthetic resin which is polyvinyl chloride or polymethyl methacrylate containing an antistatically effective amount of a compound having the formula ##STR54## 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 11
Dependent Claim
24 words
A composition according to claim 3 wherein when X - is an organic acid group it is a carboxylic acid or sulfonic acid group.
Claim 12
Dependent Claim
129 words
A composition according to claim 3 wherein X - is CH 3 SO 4 - , C 2 H 5 SO 4 - , ClO 4 - , R 5 -COO - where R 5 is H, C 1 to C 3 alkyl, CH 2 OH; CH 3 CHOH or C 6 H 5 , NO 3 - , Cl - , R 6 SO 3 - where R 6 is CH 3 , C 6 H 5 , methylphenylene or (OH)C 2 H 4 or an equivalent of SO 4 HPO 4 -- or R 7 (COO) 2 -- where R 7 is a simple direct bond, --(CH 2 ) x -- where x is 1 to 4, --CH═CH, --CH(OH)--CH(OH)--, --CH 2 --C(OH) (COOH)--CH 2 -- or phenylene.
Claim 13
Dependent Claim
24 words
A composition according to claim 5 wherein when X - is an organic acid group it is a carboxylic acid or sulfonic acid group.
Claim 14
Dependent Claim
130 words
A composition according to claim 5 wherein X - is CH 3 SO 4 - , C 2 H 5 SO 4 - , ClO 4 - , R 5 -COO - where R 5 is H, C 1 to C 3 alkyl, CH 2 OH; CH 3 CHOH or C 6 H 5 , NO 3 - , Cl - , R 6 SO 3 - where R 6 is CH 3 , C 6 H 5 , methylphenylene or (OH)C 2 H 4 or an equivalent of SO 4 = HPO 4 = or R 7 (COO) 2 -- where R 7 is a simple direct bond, --(CH 2 ) x -- where x is 1 to 4, --CH═CH, --CH(OH)--CH(OH)--, --CH 2 --C(OH) (COOH)--CH 2 -- or phenylene.
Claim 15
Dependent Claim
12 words
A composition according to claim 6 wherein the polymer is polyvinyl chloride.
Claim 16
Dependent Claim
12 words
A composition according to claim 6 wherein the polymer is polymethyl methacrylate.
Claim 17
Dependent Claim
17 words
A compound according to claim 1 having formula I wherein R 2 is 2-hydroxyethylaminoalkyl, 2-hydroxypropylaminoalkyl or 2,3-dihydroxypropylaminoalkyl.
References Cited (Backward Citations)
US2897170A
Cited
US3371130A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-23 | 1981-07-25 | 1982-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-23 | 1985-07-25 | 1986-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-23 | 1989-07-25 | 1990-01-24 | $7700.00 | Window Closed / Lapsed |