US5324812A
Expired / Lapsed
US
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Water soluble polyamide from polyalkylene glycol diamines and polycarboxylic acids
Assignee: Huntsman Corp
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Filing: 1993-04-01
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Granted: 1994-06-28
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Expires: 2013-04-01
Abstract
Abstract Water soluble polyamides may be produced by reacting two different dicarboxylic acids with at least one low molecular weight poly(alkylene glycol) diamine and at least one relatively high molecular weight polyoxyalkylene diamine. One dicarboxylic acid may be of low molecular weight, such as adipic acid and the other of relatively high molecular weight such as C36 dimer acid. In one embodiment, some dimer acid proportion is preferred. The poly(alkylene glycol) diamine may include triethylene glycol diamine and tetraethylene glycol diamine. The polyoxyalkylene diamine should have at least some ethylene oxide residue therein; for example it may be a polyoxyethylene/polyoxypropylene diamine. The resulting polyamides have a desirable combination of properties, including high strength with water solubility, the latter making the materials easier to work with and very useful.
Inventors
- 👤 George P. Speranza
- 👤 Christopher S. Henkee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 22:15
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/34; C08G69/44
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
157 words
A water soluble polyamide produced by a process comprising the steps of: (a) reacting (i) at least one low molecular weight dicarboxylic acid having from 5 to 12 carbon atoms, or ester thereof; (ii) at least one poly(alkylene glycol) diamine having the formula: ##STR6## where x ranges from about 2 to 5, R is hydrogen or an alkyl of one to four carbon atoms; (iii) at least one polyoxyalkylene diamine having the formula: ##STR7## where the sum of a+c ranges from about 2 to 8, b ranges from about 12 to about 50 and R' is an alkyl group of one to four carbon atoms; and (iv) at least one high molecular weight dicarboxylic acid having from about 20 to about 36 carbon atoms, or ester thereof; where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 2:1; and (b) recovering the water soluble polyamide.
Claim 2
Dependent Claim
157 words
A water soluble polyamide produced by a process comprising the steps of: (a) reacting (i) at least one low molecular weight dicarboxylic acid having from 5 to 12 carbon atoms, or ester thereof; (ii) at least one poly(alkylene glycol) diamine having the formula: ##STR6## where x ranges from about 2 to 5, R is hydrogen or an alkyl of one to four carbon atoms; (iii) at least one polyoxyalkylene diamine having the formula: ##STR7## where the sum of a+c ranges from about 2 to 8, b ranges from about 12 to about 50 and R' is an alkyl group of one to four carbon atoms; and (iv) at least one high molecular weight dicarboxylic acid having from about 20 to about 36 carbon atoms, or ester thereof; where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 2:1; and (b) recovering the water soluble polyamide.
Claim 3
Dependent Claim
39 words
The water soluble polyamide of claim 1 where the mole ratios of (i) to (iv) and (ii) to (iv) are at least 4:1 and the mole ratios of (i) to (iii) and (ii) to (iii) are at least 4:1.
Claim 4
Dependent Claim
27 words
The water soluble polyamide of claim 1 where the low molecular weight dicarboxylic acid is adipic acid and the high molecular weight dicarboxylic acid is dimer acid.
Claim 5
Dependent Claim
24 words
The water soluble polyamide of claim 1 where in the (ii) polyoxyalkylene diamine, R is hydrogen and x ranges from about 2 to 3.
Claim 6
Dependent Claim
27 words
The water soluble polyamide of claim 1 where in the (iii) polyoxyalkylene diamine, R' is methyl and the sum of a+c ranges from about 3 to 4.
Claim 7
Dependent Claim
116 words
A water soluble polyamide produced by a process comprising the steps of: (a) reacting (i) at least 4 moles of adipic acid, or ester thereof; (ii) at least 4 moles of a poly(ethylene glycol) diamine having the formula NH 2 --(CH 2 CH 2 O) x CH 2 CH 2 NH 2 where x ranges from about 2 to 3; (iii) one mole of a polyoxyalkylene diamine having the formula: ##STR8## where the sum of a+c ranges from about 3 to 4, b ranges from about 12 to about 50 and R' is an alkyl group of one to two carbon atoms; and (iv) one mole of dimer acid; and (b) recovering the water soluble polyamide.
Claim 8
Dependent Claim
116 words
A water soluble polyamide produced by a process comprising the steps of: (a) reacting (i) at least 4 moles of adipic acid, or ester thereof; (ii) at least 4 moles of a poly(ethylene glycol) diamine having the formula NH 2 --(CH 2 CH 2 O) x CH 2 CH 2 NH 2 where x ranges from about 2 to 3; (iii) one mole of a polyoxyalkylene diamine having the formula: ##STR8## where the sum of a+c ranges from about 3 to 4, b ranges from about 12 to about 50 and R' is an alkyl group of one to two carbon atoms; and (iv) one mole of dimer acid; and (b) recovering the water soluble polyamide.
Claim 9
Dependent Claim
35 words
The water soluble polyamide of claim 6 where the mole ratio of (i) and (ii) to (iv) is at least 10:1 and the mole ratio of (i) and (ii) to (iii) is at least 10:1.
Claim 10
Independent Claim
161 words
A method of producing a water soluble polyamide by a process comprising the steps of: (a) reacting (i) at least one low molecular weight dicarboxylic acid having from 5 to 12 carbon atoms, or ester thereof; (ii) at least one poly(alkylene glycol) diamine having the formula: ##STR9## where x ranges from about 2 to 5, R is hydrogen or an alkyl of one to four carbon atoms; (iii) at least one polyoxyalkylene diamine having the formula: ##STR10## where the sum of a+c ranges from about 2 to 8, b ranges from about 12 to about 50 and R' is an alkyl group of one to four carbon atoms; and (iv) at least one high molecular weight dicarboxylic acid having from about 20 to about 36 carbon atoms, or ester thereof; and where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 2:1; and (b) recovering the water soluble polyamide.
Claim 11
Independent Claim
161 words
A method of producing a water soluble polyamide by a process comprising the steps of: (a) reacting (i) at least one low molecular weight dicarboxylic acid having from 5 to 12 carbon atoms, or ester thereof; (ii) at least one poly(alkylene glycol) diamine having the formula: ##STR9## where x ranges from about 2 to 5, R is hydrogen or an alkyl of one to four carbon atoms; (iii) at least one polyoxyalkylene diamine having the formula: ##STR10## where the sum of a+c ranges from about 2 to 8, b ranges from about 12 to about 50 and R' is an alkyl group of one to four carbon atoms; and (iv) at least one high molecular weight dicarboxylic acid having from about 20 to about 36 carbon atoms, or ester thereof; and where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 2:1; and (b) recovering the water soluble polyamide.
Claim 12
Dependent Claim
39 words
The water soluble polyamide of claim 8 where the mole ratios of (i) to (iv) and (ii) to (iv) are at least 4:1 and the mole ratios of (i) to (iii) and (ii) to (iii) are at least 4:1.
Claim 13
Dependent Claim
25 words
The method of claim 8 where the low molecular weight dicarboxylic acid is adipic acid and the high molecular weight dicarboxylic acid is dimer acid.
Claim 14
Dependent Claim
22 words
The method of claim 8 where in the (ii) polyoxyalkylene diamine, R is hydrogen and x ranges from about 2 to 3.
Claim 15
Dependent Claim
25 words
The method of claim 8 where in the (iii) polyoxyalkylene diamine, R' is methyl and the sum of a+c ranges from about 3 to 4.
Claim 16
Independent Claim
127 words
A method of producing a water soluble polyamide by a process comprising the steps of: (a) reacting (i) adipic acid, or ester thereof; (ii) a poly(ethylene glycol) diamine having the formula NH 2 --(CH 2 CH 2 O) x CH 2 CH 2 NH 2 where x ranges from about 2 to 3; (iii) a polyoxyalkylene diamine having the formula: ##STR11## where the sum of a+c ranges from about 3 to 4, b ranges from about 12 to about 50 and R' is an alkyl group of one to two carbon atoms; and (iv) dimer acid; and where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 4:1; and (b) recovering the water soluble polyamide.
Claim 17
Independent Claim
127 words
A method of producing a water soluble polyamide by a process comprising the steps of: (a) reacting (i) adipic acid, or ester thereof; (ii) a poly(ethylene glycol) diamine having the formula NH 2 --(CH 2 CH 2 O) x CH 2 CH 2 NH 2 where x ranges from about 2 to 3; (iii) a polyoxyalkylene diamine having the formula: ##STR11## where the sum of a+c ranges from about 3 to 4, b ranges from about 12 to about 50 and R' is an alkyl group of one to two carbon atoms; and (iv) dimer acid; and where the mole ratios of (i) to (iii), (ii) to (iii), (i) to (iv) and (ii) to (iv) are all at least 4:1; and (b) recovering the water soluble polyamide.
Claim 18
Dependent Claim
33 words
The method of claim 13 where the mole ratio of (i) and (ii) to (iv) is at least 10:1 and the mole ratio of (i) and (ii) to (iii) is at least 10:1.
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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) | 1997-06-27 | 1997-12-27 | 1998-06-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-06-27 | 2001-12-27 | 2002-06-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-06-27 | 2005-12-27 | 2006-06-28 | $7700.00 | Window Closed / Lapsed |