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US4477654A
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3-Hydroxybutyrate polymers
Assignee: Syngenta Ltd
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Filing: 1982-06-29
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Granted: 1984-10-16
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Expires: 2002-06-29
Abstract
Abstract High molecular weight copolymers containing 3-hydroxybutyrate residue, i.e. units of the formula -O.CH(CH3).CH2.CO- and up to 50 mole % of residues of other hydroxy acids, viz units of the formula -O.CR1R2.(CR3R4)n.CO- where n is 0 or an integer and, if n=1 and R2, R3, and R4=H, R1 is not methyl. The copolymers are made microbiologically: for part of the cultivation the micro-organism is under conditions such that polymer is accumulated, e.g. by limitation of a nutrient, e.g. nitrogen source, required for growth but not polyester accumulation. For at least part of this period of polymer accumulation the substrate is an acid or a derivative thereof that gives the comonomer units. Proprionic acid, which gives polymers where n=1, R2=R3=R4=H and R1=C2H5, is the preferred acid.
Inventors
- 👤 Paul A. Holmes
- 👤 Stephen H. Collins
- 👤 Leonard F. Wright
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 11:32
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/06; C12; C12P; C12P7/00; C12P7/62; C12P7/625; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/829; Y10S435/872
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
103 words
Copolymers having a weight average molecular weight above 10,000 and containing repeat units --O.CH(CH.sub.3).CH.sub.2.CO-- I and repeat units --O.CR.sup.1 R.sup.2.(CR.sup.3 R.sup.4).sub.n.CO-- II where n is 0 or an integer and R 1 , R 2 , R 3 , and R 4 are each selected from hydrocarbon radicals: halo- and hydroxy-substituted hydrocarbon radicals; hydroxy radicals; halogen atoms; and hydrogen atoms, provided that, where n is 1 and R 2 , R 3 , and R 4 are each hydrogen atoms, R 1 is not methyl, said repeat units II constituting 0.1 to 50 mole % of the total repeat units in said copolymer.
Claim 2
Dependent Claim
103 words
Copolymers having a weight average molecular weight above 10,000 and containing repeat units --O.CH(CH.sub.3).CH.sub.2.CO-- I and repeat units --O.CR.sup.1 R.sup.2.(CR.sup.3 R.sup.4).sub.n.CO-- II where n is 0 or an integer and R 1 , R 2 , R 3 , and R 4 are each selected from hydrocarbon radicals: halo- and hydroxy-substituted hydrocarbon radicals; hydroxy radicals; halogen atoms; and hydrogen atoms, provided that, where n is 1 and R 2 , R 3 , and R 4 are each hydrogen atoms, R 1 is not methyl, said repeat units II constituting 0.1 to 50 mole % of the total repeat units in said copolymer.
Claim 3
Dependent Claim
9 words
Copolymers according to claim 1 wherein n is 1.
Claim 4
Dependent Claim
24 words
Copolymers according to claim 1 wherein R 1 , R 2 , R 3 and R 4 each contain less than 4 carbon atoms.
Claim 5
Dependent Claim
23 words
Copolymers according to claim 1 wherein at least one of R 1 , R 2 , R 3 and R 4 is hydrogen.
Claim 6
Dependent Claim
17 words
Copolymers according to claim 4 wherein R 2 , R 3 and R 4 are each hydrogen.
Claim 7
Dependent Claim
16 words
Copolymers according to claim 5 containing repeat units --O.CH(CH.sub.3).CH.sub.2.CO-- I and repeat units --O.CH(C.sub.2 H.sub.5).CH.sub.2.CO-- II
Claim 8
Dependent Claim
36 words
Copolymers according to claim 5 containing repeat units --O.CH(CH 3 ).CH 2 .CO-- together with repeat units --O.CH 2 .CH 2 .CO-- alone or in conjunction with repeat units --O.CH(C 2 H 5 )CH 2 .CO--.
Claim 9
Dependent Claim
15 words
Copolymers according to claim 1 containing 1 to 40 mole % of repeat units II.
Claim 10
Dependent Claim
58 words
Copolymers having a weight average molecular weight above 10,000 and containing at least 50 mol % of repeat units --O.CH(CH.sub.3)CH.sub.2.CO-- and being characterised by a triplet at 4.3 ppm as measured by proton nuclear magnetic resonance spectroscopy and peaks at 59.89 and 33.83 ppm (relative to a tetramethyl silane standard) measured by 13 C nuclear magnetic resonance spectroscopy.
Claim 11
Dependent Claim
58 words
Copolymers having a weight average molecular weight above 10,000 and containing at least 50 mol % of repeat units --O.CH(CH.sub.3)CH.sub.2.CO-- and being characterised by a triplet at 4.3 ppm as measured by proton nuclear magnetic resonance spectroscopy and peaks at 59.89 and 33.83 ppm (relative to a tetramethyl silane standard) measured by 13 C nuclear magnetic resonance spectroscopy.
Claim 12
Dependent Claim
13 words
Copolymers according to claim 1 having a weight average molecular weight above 200,000.
Claim 13
Dependent Claim
136 words
A process for the production of a thermoplastic polyester wherein a micro-organism that is capable of accumulating a polyester is cultivated in an aqueous medium on a water soluble assimilable carbon containing substrate with at least part of the cultivation being conducted under conditions such that the micro-organism accumulates at least 10% by weight of polyester, characterised in that, at least during part of the period when polyester is being accumulated, the substrate comprises an organic acid, or derivative thereof, that is metabolisable by said micro-organism under said polyester accumulating conditions to a polyester other than one composed solely of --O.CH(CH 3 ).CH 2 .CO-- repeat units, the amount the combined carbon in said acid, or derivative thereof, constituting at least 2% by weight of the total combined carbon in the substrate present throughout said period.
Claim 14
Dependent Claim
136 words
A process for the production of a thermoplastic polyester wherein a micro-organism that is capable of accumulating a polyester is cultivated in an aqueous medium on a water soluble assimilable carbon containing substrate with at least part of the cultivation being conducted under conditions such that the micro-organism accumulates at least 10% by weight of polyester, characterised in that, at least during part of the period when polyester is being accumulated, the substrate comprises an organic acid, or derivative thereof, that is metabolisable by said micro-organism under said polyester accumulating conditions to a polyester other than one composed solely of --O.CH(CH 3 ).CH 2 .CO-- repeat units, the amount the combined carbon in said acid, or derivative thereof, constituting at least 2% by weight of the total combined carbon in the substrate present throughout said period.
Claim 15
Dependent Claim
17 words
A process according to claim 11 wherein the acid is selected from propionic, isobutyric, and acrylic acid.
Claim 16
Dependent Claim
36 words
A process according to claim 11, wherein the acid is the sole substrate for at least part of the period during which the cultivation of the micro-organism is conducted under conditions causing polyester to be accumulated.
Claim 17
Dependent Claim
19 words
A process according to claim 13 wherein the acid is the sole substrate throughout the cultivation of the micro-organism.
Claim 18
Dependent Claim
17 words
A process according to claim 11 wherein the micro-organism is grown using a carbohydrate as a substrate.
Claim 19
Dependent Claim
11 words
A process according to claim 15 wherein the carbohydrate is glucose.
Claim 20
Dependent Claim
34 words
A process according to claim 15 wherein, for at least part of the period when the cultivation is under conditions causing polyester accumulation, the substrate is a mixture of the acid and the carbohydrate.
Claim 21
Dependent Claim
35 words
A process according to claim 11 wherein the micro-organism is caused to accumulate polyester by cultivation under conditions of limitation of one or more of the essential requirements for microbial growth but not polyester accumulation.
Claim 22
Dependent Claim
27 words
A process according to claim 18 wherein the essential requirement for growth, but not polyester accumulation, that is limited, is the nitrogen source, or the phosphorus source.
Claim 23
Dependent Claim
47 words
A process according to claim 11 wherein the acid, or derivative thereof, that is metabolisable to a polyester other than one composed solely of --O.CH(CH 3 ).CH 2 .CO-- units, is the sole organic acid, or derivative thereof, present during the period when polyester is being accumulated.
Claim 24
Dependent Claim
25 words
Cells of a poly(hydroxybutyrate)-accumulating micro-organism containing at least 10% by weight of said polyester wherein said polyester comprises a copolymer as claimed in claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-16 | 1988-04-16 | 1988-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-16 | 1992-04-16 | 1992-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-16 | 1996-04-16 | 1996-10-16 | $7700.00 | Window Closed / Lapsed |