US4379890A
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Water-soluble polymers carrying quaternary ammonium groups, their preparation and use
Assignee: Huels AG
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Filing: 1981-07-09
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Granted: 1983-04-12
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Expires: 2001-07-09
Abstract
Abstract A water-soluble polymer having quaternary ammonium groups, is prepared by reacting (a) a low molecular weight alkylating agent with (b) a corresponding polymer carrying tertiary, quaternizable amino groups.
Inventors
- 👤 Alfred Konietzny
- 👤 Wilfried Bartz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 12:01
CPC Classifications
C; C08; C08C; C08C19/00; C08C19/30; C08L; C08L97/00; C08L97/02; B; B27; B27K; B27K3/00; B27K3/02; B27K3/15; C08L63/00; C08L79/00; C08L79/02; C08L9/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
400 words
A water-soluble polymer having quaternary ammonium groups, prepared by reacting (a) a low molecular weight alkylating agent with (b) a corresponding polymer carrying tertiary, quaternizable amino groups, wherein (a) is a low molecular weight oxirane of the formula ##STR4## wherein R 6 and R 7 each independently is hydrogen or alkyl of 1 or 2 carbon atoms optionally substituted by hydroxy or chloride or R 6 or R 7 together represent a 1,3-propylene or 1,4-butylene chain forming a five- or six-membered ring with the carbon atoms of the oxirane; (b) is a polymer which is prepared by epoxidizing up to a content of titratable epoxy oxygen of 2-10 weight %, a polymer of 1,3 butadiene monomer having a molecular weight (M n ) of 500-6,000, and prepared from at least 70 mole % of 1,3-butadiene and up to 30 mole % of another copolymerizable 1,3-diolefin or an α-unsaturated monoolefin, aminating the resultant epoxidation product with a primary-tertiary or secondary-tertiary diamine of the formula ##STR5## wherein, R 1 is hydrogen and n is an integer of 2 to 6, R 2 and R 3 each independently is hydrogen of alkyl of 1-4 carbon atoms, ##STR6## represents the same or different chain members, and R 4 and R 5 each independently is straight chain alkyl of 1-4 carbon atoms optionally substituted by hydroxy or alkoxy of 1-4 carbon atoms, excluding the α-position of the alkyl residue as a point of substitution, or R 4 and R 5 together can form a five- or six-membered ring together with the tertiary nitrogen atom; or R 1 is alkyl of 1 or 2 carbon atoms, optionally substituted by hydroxy or alkoxy of 1 or 2 carbon atoms, excluding the α-position of the alkyl residue, n and R 2 through R 5 are as defined above, and when n is 2 and R 2 and R 3 each is hydrogen, then R 1 and R 4 together with the two nitrogen atoms can also form a six-membered ring, up to a content of tertiary, quaternizable amino groups of 0.05-0.5 mole/100 g of the amination product, said groups being located in the side chain and linked to a carbon atom stemming either from the primary chain or from a vinyl group of the polymer via 3-7 chain atoms, and in the quaternization reaction, 0.05-0.5 mole of the tertiary amino groups/100 g of the amination product are quaternized.
Claim 2
Dependent Claim
400 words
A water-soluble polymer having quaternary ammonium groups, prepared by reacting (a) a low molecular weight alkylating agent with (b) a corresponding polymer carrying tertiary, quaternizable amino groups, wherein (a) is a low molecular weight oxirane of the formula ##STR4## wherein R 6 and R 7 each independently is hydrogen or alkyl of 1 or 2 carbon atoms optionally substituted by hydroxy or chloride or R 6 or R 7 together represent a 1,3-propylene or 1,4-butylene chain forming a five- or six-membered ring with the carbon atoms of the oxirane; (b) is a polymer which is prepared by epoxidizing up to a content of titratable epoxy oxygen of 2-10 weight %, a polymer of 1,3 butadiene monomer having a molecular weight (M n ) of 500-6,000, and prepared from at least 70 mole % of 1,3-butadiene and up to 30 mole % of another copolymerizable 1,3-diolefin or an α-unsaturated monoolefin, aminating the resultant epoxidation product with a primary-tertiary or secondary-tertiary diamine of the formula ##STR5## wherein, R 1 is hydrogen and n is an integer of 2 to 6, R 2 and R 3 each independently is hydrogen of alkyl of 1-4 carbon atoms, ##STR6## represents the same or different chain members, and R 4 and R 5 each independently is straight chain alkyl of 1-4 carbon atoms optionally substituted by hydroxy or alkoxy of 1-4 carbon atoms, excluding the α-position of the alkyl residue as a point of substitution, or R 4 and R 5 together can form a five- or six-membered ring together with the tertiary nitrogen atom; or R 1 is alkyl of 1 or 2 carbon atoms, optionally substituted by hydroxy or alkoxy of 1 or 2 carbon atoms, excluding the α-position of the alkyl residue, n and R 2 through R 5 are as defined above, and when n is 2 and R 2 and R 3 each is hydrogen, then R 1 and R 4 together with the two nitrogen atoms can also form a six-membered ring, up to a content of tertiary, quaternizable amino groups of 0.05-0.5 mole/100 g of the amination product, said groups being located in the side chain and linked to a carbon atom stemming either from the primary chain or from a vinyl group of the polymer via 3-7 chain atoms, and in the quaternization reaction, 0.05-0.5 mole of the tertiary amino groups/100 g of the amination product are quaternized.
Claim 3
Dependent Claim
15 words
A polymer of claim 1 wherein the polymer of 1,3 butadiene monomer is a homopolymer.
Claim 4
Dependent Claim
50 words
A polymer of claim 1 wherein the polymer of 1,3 butadiene monomer is prepared from at least 90 mole % of 1,3-butadiene, the molecular weight M n is 1,000-2,500, less than 40% of its double bonds are trans-double bonds, and the iodine number is at least 100 g iodine/100 g.
Claim 5
Dependent Claim
50 words
A polymer of claim 1 wherein the polymer of 1,3 butadiene monomer is prepared from at least 90 mole % of 1,3-butadiene, the molecular weigt M n is 1,000-2,500, at least 40% of its double bonds are cis-double bonds, and the iodine number is at least 100 g iodine/100 g.
Claim 6
Dependent Claim
26 words
A polymer of claim 1 wherein the epoxidation is carried out up to a content of 3-9 weight % of titratable epoxy oxygen in the polymer.
Claim 7
Dependent Claim
19 words
A polymer of claim 1 wherein the amination produces a product having 0.07-0.3 mole/100 g of quaternizable amino groups.
Claim 8
Dependent Claim
10 words
A polymer of claim 1 wherein the diamine is N,N-dimethyl-1,3-propylenediamine.
Claim 9
Dependent Claim
24 words
A polymer of claim 1 wherein, in addition to the diamines, the amination is conducted in the presence of a primary or secondary monoamine.
Claim 10
Dependent Claim
11 words
A polymer of claim 1 wherein the oxirane is ethylene oxide.
Claim 11
Dependent Claim
23 words
A polymer of claim 1 wherein 0.07-0.3 mole/100 g of polymer of the quaternizable amino groups has been quaternized in the quaternization step.
Claim 12
Dependent Claim
16 words
A polymer of claim 1 wherein the quaternization is conducted in the presence of carbonic acid.
Claim 13
Dependent Claim
25 words
In an aqueous impregnant for wood and wooden materials comprising water and a binder, the improvement wherein the binder is a polymer of claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-04-11 | 1986-10-11 | 1987-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-11 | 1990-10-11 | 1991-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-11 | 1994-10-11 | 1995-04-12 | $7700.00 | Window Closed / Lapsed |