WO1992021708A1 - Biodegradable polymer, production thereof, and use thereof - Google Patents

Biodegradable polymer, production thereof, and use thereof Download PDF

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Publication number
WO1992021708A1
WO1992021708A1 PCT/JP1992/000732 JP9200732W WO9221708A1 WO 1992021708 A1 WO1992021708 A1 WO 1992021708A1 JP 9200732 W JP9200732 W JP 9200732W WO 9221708 A1 WO9221708 A1 WO 9221708A1
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scan
ru
ch
down
les
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PCT/JP1992/000732
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French (fr)
Japanese (ja)
Inventor
Ichihiko Yamamoto
Makoto Kurihara
Taku Sato
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Kirin Beer Kabushiki Kaisha
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    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12RPROCESSES USING MICROORGANISMS
    • C12R1/00Processes using microorganisms
    • C12R1/01Processes using microorganisms using bacteria or actinomycetales
    • C12R1/38Pseudomonas
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/62Carboxylic acid esters
    • C12P7/625Polyesters of hydroxy-carboxylic acids

Abstract

A novel biodegradable copolyester composed of the structural units represented by general formulae (I) and (II) and having a number-average molecular weight of at least 50,000; a novel pseudomonas which can produce the copolyester; and a process for producing the copolyester by culturing the pseudomonas in formulae (I) and (II) wherein X and Y represent each an integer of 0 to 16.

Description

Akira willow biodegradable polymer compound, good preparation you of its beauty its APPLICATIONS technology fraction field of

The present invention is related to the co-po Li et scan Te le that having a biodegradable, that is is rather to more in La having a biodegradable co-po Li et scan Te Le, had use a new micro-organisms As a manufacturing method, your good beauty, about the APPLICATIONS of it.

Heat

冃 technology

In recent years, or that people interested Do Ru high or Ri Tsu One ransom for against the boundary problem, synthetic-flops La scan Chi-click the viewpoint et al serious ri ¾ of environmental pollution Ya resource recycling P «J τάί ing the optimum is, Po representative examples of biodegradable-flops La scan switch click the attention is One Tsu Oh Ru ο biodegradable that have been conventional inform blanking La scan switch click to

• J - 3 - human de σ key shea-flops Chi-les-over door (Ρ Η Β) Chikaraku Oh Ru. Second material, E, channel formic storage material and to many Ku also to the Ah Ru force Ru is 蓄 ¾ to cells within the microbial, while the thermoplastic high that have a good biodegradability Oh Ru in the molecule. And follow, the son of Ρ Η Β Ri Oh a place I old port Li Ma over do not want to depend on oil, the environment Ru conservation be - the "click re-down-flops La scan switch click" Oh Ru in to attention is to 0 Mr. Kaka that has such power ", et al., including diverse physical properties of the current-flops La scan Chi Tsu biodegradable that have been asked Me, et al. to click, Ρ Η Β your good beauty Ρ Η Β the Ri Oh is impossible with this you force bar with only the including both heavy case body, Ρ Η B alone is we have a Ru Tei have a problem that you have with the brittle this whether et al while creating had Ru synthesis Oh is that not new plus switch-click with doubles as a biodegradable regardless of the non-synthesis is required, et al. are.

The present inventors have found that the search of cormorants Ru novel high-content child answer to Do you Yo this demand as a purpose, a large number of microorganisms separated from soil or et al., Separated search the production eggplant that the polymer of its this filtrate and was, Oh Ru species of micro-organisms is heading a call that forms produce a useful co-po Li et scan Te le with the new, and have completed the present invention.

The present invention and follow is, Ru a call that provides a novel co-po Li et scan Ter that have a biodegradable and purpose Tei.

Or the present invention is, Shi purpose a call that provides a novel microorganism that have a novel biodegradable co-po Li es Tel ability that eggplant production of this C 'o

Of the present invention et al., It had use of the microorganisms of this, that has a call that provides a process for the preparation of novel biodegradable co-po Li et scan tape Lumpur and purpose o

The present invention was or in of et al., Ru Tei to a call that provides port Li Ma one-flops down de with improved flexibility and Hishibo to PHB and purpose

Other purpose the following description force of that of the present invention, intends der filtrate Do that whether Akira Luo, et al.

Inventions of disclosure

That by the present invention co Po Li et scan te Honoré, the structural units and the force is the table by the following general formula structural unit general formula that will be table in (I) (II), the number-average molecular weight et ing 5 0, 0 0 0 that have a more than o (

Of, in Ru Oh C c I.

HH

2

) C

HX

2 C

HC (I)

o 3

And H one to H = CH, CH c) one yCH

OCH - in CH single CO (II) formula, X Contact yo beauty Y is an integer of 0-1 6. ) In addition, a novel microorganism that by the present invention, Ru Oh in a novel strain you belong to Shi Yu over de 乇 na scan ♦ off Norre O LESSON cell down the nest.

Et al. Is, the co-po Li et scan Te le of the production process that by the present invention belong to the down Yoo over Γ · Mo na scan the genus, you said co-po Li et-scan capability that forms produce a Te le culturing the bacteria, also of, in Ru Oh it said a call you collect the culture at the foot matter whether we the co-po Li E scan te Norre.

It was or to of, et al., That due to the onset Ming Po Li Ma over Breakfast Les down soil, also of, in Ru Oh ing and a pre-Symbol co-po Li et scan te Norre and PHB.

Brief description of the drawings

FIG] is Example: shows the polymer of the infrared absorption scan Bae click preparative Le of I (key Ya scan Bok off I Honoré beam method).

Figure 2 shows a polymer of profile Bok emission nuclear magnetic resonance scan Bae click Bok Le of 施例 1 (5 0 0 MH z, heavy click B port e in Le beam).

Figure 3 shows the polymer carbon nuclear magnetic co-sounding scan Bae click preparative Le (1 2 5 MH z, heavy click B B E Honoré in beam) Example 1.

Figure 4 is a first embodiment of a polymer or we obtain et a, Table 4 your only that mono Ma one A 2 of profile tonnes nuclear magnetic co-sounding scan Bae click preparative Le (5 0 0 MH z , show a heavy click b b e Norre in-time).

Figure 5 is a first embodiment of a polymer or we obtain et a, Table 4 your only that mono M a B 2 of profile tonnes nuclear magnetic co-sounding scan Bae click preparative Le (5 0 0 MH z . shows the double-click b b e Norre in-time).

6, embodiment or we obtained we were polymers 1, Table 4 your only that mono M a A 3 of profile tonnes nuclear magnetic co-sounding scan Bae click preparative Le (5 0 0 MH z show a heavy click furnace opening e in Le-time).

Figure 7 shows infrared absorption scan Bae click Bok Honoré heavy of Example 1 5 (, key Ya scan walk I Le beam method) the.

Figure S shows a profile tons nuclear magnetic resonance scan base click preparative Le t SOOMH zs heavy click B B E Honoré in beam) of the polymer of Example 1 5.

Figure 9 shows the heavy Carbon nuclear magnetic resonance operative click preparative le of Example 1 5 (1 2 5 MH z, heavy click B port e in Le beam).

BEST MODE order to you the Invention

Co-Po Li et scan tape Norre HY - 1:

That by the present invention co Po Li et scan Te Le, the general formula I) Contact good beauty ([pi) structural units that will be respectively table in (I) Contact good beauty ([pi) force, also et ing der of Ru (tail, and have your herein, the that by the present invention co-po Li es Te le simply - Ru this and there referred to as the "HY 1").

HY - array of one to you only that the structural units (I) your good beauty (!!) is, blanking lock, but it may also be Oh Tsu in the shift had run-dam. The composition of the structure units of (I) your good beauty (II) is, up La scan switch Tsu physical properties of the click material and to, but ∎ You can at appropriately determined in consideration of the etc. biodegradable, structural units of ( in good or was rather the assembled formed a molar% of I) 0. 1 ~ 9 9. 9, good Ri rather than the good or the Ri Oh in the range of 7 0-9 8, or structural units of the (H) composition force "9 9.9 to 0.1, good Ri rather than the good or the Ru Oh in the range of 3 0 to 2.

And have you in the general formula (I) your good beauty (11), X your good beauty Y is an appropriately determined in the range that you to realize the physical properties Nozomi or is that in APPLICATIONS of as a polymerized compound but ∎ you can, its Re respectively 0-1 6, good or was rather the 〇 to ​​1 2, good Ri rather than the good or the Ru Oh in the 2 to 9. In addition, the structural units of the Soviet Union was the general formula (I) or other (Π) range contains or is Ru limit is, is it different X your good beauty γ to have you in the structural units in the molecule of even though Tsu not good.

Et al is, HY - 1 of physical properties, the ends of its structural units were or in the molecule of the biodegradable especially, the influence by the given example has name range to as the third component, eg if you via e scan te Lumpur. binding, but it may also be present.

HY - 1 of molecular weight properties of the flop la scan switch click material, but Ru appropriately determined in consideration of biodegradability, the molecular weight obtained it is Ru in One by the gel filtration law good or and rather than the 1 0, 0 ◦ 0 ~

5, 0 0 0, 0 0 0, good Ri good or to rather than the 1 0, 0 0 0 ~ 2, 0 0 U, Ri Oh in the range of ϋ 0 0, the number average molecular weight

5 0, [] Oh Ru 0 0 or more. HY - 1 is Ru are obtained found by a high viscosity like material viscous at room temperature generally Ri by the Ru When METHANOL precipitation good to the preparation that by the microorganism you later, the solvent in vacuo also the even Ru Oh resulting et been Ru as a you completely remove the solid product (full I Le beam-like material). This Η Υ - 1 is Ri soluble der to click furnace opening Ho Lum, Ri § Seto sparingly soluble der in emissions, METHANOL, error data Roh Lumpur, Ru insoluble der in water.

Said that due to this bright Η Υ - 1, the microorganism Ru η η Is the production in Tsu by the co-po Li et scan te Rudea is, energy sources of 蓄 you are life activities in cells of microorganisms originally it is estimated that Ru Oh in function and Tei Ru material as a. Chi I sand, the Eta Upsilon - 1 is self Shikakai ο Ri substance der that obtained incorporated into carbon Size Lee click Le, Re et suspect to be a polymer compound that could be resolved by One in microorganisms that.

Also, Η Υ - 1 Waso second and if we in the molecule that have a double bond, using the double bond of this, Η Υ - Ru can der - one molecule to qualify ' . For example, the Manko ^ using the double bond of this Η Υ - is and this you improve the physical properties of the 1 to be that in Tsu by the and the child as a plus switch-click 衬钭 be introduced possible Ru der.

Et al is, Eta Upsilon - 1 are biodegradable high content Ryo-reduction is heading in this Rema ¾, and Oh Ru two generally flexible material in comparison with the example, if [rho Eta beta or al , it was added to this to be the, that Ki out and this Ru physicians use as a port Li Ma one blanking Les down mode. Also, Η Υ - 1 Ri by the on and this you added to other biodegradable ¾-molecular-weight compounds, that Ki de properties of the polymerization product of its, and this you improve flexibility For example is . Chi be, HY - 1 is that having a use of a physical property-improving agent of the other polymer compound.

HY - 1 a biodegradable polymer compound softening agent to you use if, blanking Les emission de ratio of its generally HY -. 1 3 0-2 5 by weight%, . other biodegradable polymer compound 7 0-9 7 5 wt% is good or teeth rather, is good or to have flop Les emission de ratio La, HY -. 1 Chikaraku 2 5-2 5 weight %, other biodegradable polymer compound force 7 5-9 7. Ru Ah with 5 wt%. Is the other biodegradable polymers of compound PHB is not to good or. In particular, 0 the number average molecular weight is 1 ◦, Oh Ru PHB force good or was not in the 0 0 0.

HY - 1 is the port re M a blanking les down de of the PHB, compared to PHB Ri Contact is improved the flexibility of its potential for use as a molding materials of that is wide Ru example have stomach.

Po Li Ma - method of manufacturing a-flops down soil have such limited especially, but example if PHB your good beauty HY - 1 you dissolved rather than good to the co-solvent

(Eg example, click B B E Norre arm, di-click B B meta-down, etc.) to good rather than dissolved, mixed ^ and, after evaporation of the solvent, how that turn into heated crystal, both components after mixing by heating dissolved, Ru are methods Dogakyo up al that turn into heating crystals.

Also, said port Li Ma over Breakfast Les emissions de Tsu was Oh the use of, stabilizers, mold release 剂, lubricants, plasticizers, etc. of additives, pigments, dyes, moth La cellulose fiber, etc. of the filler Do etc. also have the good or a child you added.

Contact name, HY - 1 is, if the resulting et al is Ru as a full Lee Le beam-like product Ri Yi to by that process a microorganism you later was ¾ Hate示 tests Example 2 below 1 to jar I wonder if the mechanical properties or Akira Luo, et al., HY - 1, food packaging for a full I-le-time for example, shopping bags, obtained directly molded etc. off I-le-time for agriculture, was or, paper Ceiba click of a water-resistant co-over door agent, Te I first class of the field scan port over Tsu for capital material of Gore-le-off, DDS for the material, the use of the etc. surgical sutures Ru is in the expected 0

New Shi Yu over de mode na scan bacteria belonging to the genus:

Deposit of Microorganisms

Microorganisms that by the present invention, Gunma Prefecture of soil ¾ or we separated, new strains (2 types) that have been taken adopted Ru der. To this is we strain door also mycological properties you later, Bergey 's are Manual of Det erni i na tive B cteriol o the 8th edition by reference to the same 疋, Shi Yu over de mode na scan ( Pseudomonas) of the genus full O LESSON cell down the scan (Π uorescens) this and the force is bacteria der Ru and recognized et al belonging to ¾, et al., push from one each Domona vinegar off Norre au-les-Tsu cell down vinegar 0 - it was named 0 shares your good beauty Shi Yu over de mode na scan ♦ off Norre au-les-Tsu cell down the scan · G 1 2 0 1 share. This is al strain accession number "Bye Kenjo nearest third 3 5] Patent and third 8 7 No. 5 (FERMBP - 3 3 5 1 and BP - 3 8 7 5)" to be in the door its Resolution Re April 1991 1 0 days you good in 1992 May 2, 7 days beauty has been deposited with the International Trade and industry Ministry Agency Fermentation Research Institute o

Mycological properties

(A 3 present invention by that Shi Yu over Domu na scan the genus ^ a Oh Ru Shi Yu over de representative examples of bacteria to model na vinegar full-O-les-Tsu cell down the scan ♦ 0 - 3 0 shares bacteriological of if the enumeration of the nature Ru der Ri following through.

I. Morphological properties (3 0 ° C in 1-2 days observation)

. 1 cells form your good beauty large can of: bacillus

. 2 multi-formation presence or absence of cells: found in JP et al Rena had

. 3 (epiphytic state of flagellar) motility of the presence or absence: Yes (Tankyokuke)

. 4 presence or absence of spore: formation to have such

. 5 g stainability: negative

. 6 anti-acidic: negative

. II you only that growth state in each medium (~ 1 3 0 ° C: L 4 days observation)

Ru Der your Ri When the next Ru are shown in Table.

Table 1

Surface slip force, in the raised circular

Broth agar plate medium

The color is light brown

To grow and spread thinly

Gravy heaven slants

The color is light brown

Grow to turbid, resulting in precipitation

Broth liquid medium

Well grown in broth gelatin stab culture medium surface,

It is recognized liquefaction

peptone

. III Physiological properties (3 0 ° C in 1-2 1 days observation) 1. Reduction of nitrates of Li Thomas milk: negative

2. denitrification: negative

3. MR Te be sampled: negative

4. VP Te be sampled: negative

5. generation of fin Dawe Lumpur: negative

6. Generation of hydrogen sulfide: Negative

7. oxidation of Dar co-phosphate: negative

. S decomposition of error scan click Li emissions: positive

9. decomposition of horse urea: positive

10. A Rugini down di human mud La over Ze: positive

11. Li di down decarboxylation: negative

12. Oh Le two Chi emissions decarboxylation: negative

. 1S full two-two Le § La double down de § Mi Roh reaction: negative

14. § Shi Rua Mi da one Ze: negative

15. T ween 8 0 decomposition: positive

. 1 β Devon-flops down of hydrolysis: negative

17. use of click E phosphate: positive

15. use of inorganic nitrogen source

Nitric acid mosquito Li cormorant-time: positive

Sulfuric acid A down monitor © 厶: positive

〗 9. generation of dye: spread the water-soluble fluorescent dye in the medium

20. © Les A over Ze: positive

21, O key compressed into one zero: positive force cod one Ze: positive

Range of growth

Growth in the p H 5 ~ 8, the optimum p H 6-7

Growth at a temperature 1 0 ~ 3 0 ° C, that the optimum temperature against the 2 0 2 5 ° C oxygen Attitude: aerobic

0 - F Te be sampled: oxidative

The presence or absence of production of sugar or these acid your good beauty gas

(Base-flops tons water)

L over § La bi-door over the scan one

D - key was filtered over scan +

D - grayed Le courses +

D - Ma down node on the scan +

D - off La click Bok over scan +

D - moth La click bet over the scan

maltose

Tio sugar +

lactose

DOO Les /, and Russia over the scan +

D - Soviet Norre bi Tsu Bok

D - Ma down two Tsu Bok +

Lee raised to the power of Tsu Bok soil

Grayed Li cell Li down +

Devon-flops down + 2

Dutch studies nature of the CB j present invention by that Shi Yu over Domu na scan the genus other Oh Ru Shi Yu over de a typical example of a bacterium in model na vinegar off Noreo Les Tsu cell down the scan ♦ G 1 2 0 1 share if the enumeration Ru der Ri following through.

I. Morphological properties (3 0 ° C in 1-2 days observation)

. I form of cell Hoyo 'beauty large can of: bacillus

Multi-formation presence or absence of the cell: especially recognized et al Rena had

The presence or absence of motility (epiphytic state of flagella): Yes (Gokumuchike) the presence or absence of spore: formed such t,

Gram staining: negative

I :. growth state your only that in each medium (1 in 3 0: L 4 days between the view you,)

IX 'Ru der your Ri and shown to Ru in Table.

The second table juice agar plate surface slip force, in the raised circular

The color is growing spread thin, light brown

Broth agar slants

Color grows light brown juice broth turbid, resulting in precipitation

Well-grown meat Γ Tozerachin 穿剌 surface of the medium,

Liquefaction is re Thomas ♦ milk Pepubokun reduction observed [II (observed between 1-2 per day at 3 0 ° C) Physiological properties 1. MR Te be sampled:. Negative

2. VP Te be sampled: negative

3. generation of fin de LUMPUR: negative

4. generation of hydrogen sulfide: negative

5. A Le Guinea emissions di human mud La over Ze: positive

6. Li di down decarboxylation: negative

7. Oh Le two Chi emissions decarboxylation: negative

8. use of click E phosphate: positive

9. generation of dye: spread the water-soluble fluorescent dye in the medium] 0. © Les A over Ze: positive

11. O key sheet Dark-Ze: positive

12. mosquitoes cod over Ze: positive

13. range of growth

Growth in the p H 5 ~ l 0, the optimum p H La-7

14.0 - F Te be sampled: acid of specific

15. presence or absence of production of sugar or these acid

Medium composition: dihydrogen phosphate Anmoniumu 0, 1%

Potassium chloride 0.02% magnesium sulfate 0.02%

Ten%

L Ara bi Bok over scan

D- xylose +

D one glucose + D- mannose +

D- Fracture toast +

D- galactopyranoside door Ichisu +

maltose

Sucrose soil (growth is permitted) lactose

Bok Les -, ヽ π-- scan

D- Sorubi' Bok

D- Man'ni' Bok

Ino N'Bok

(Acid growth is also observed not generate) glycerin +

Starch one

Identification of strains

The identified grounds and Ru novel strain der that then belong to by that strain of the present invention to push from one de mode na scan ♦ off Norre O LESSON cell down the scan are shown below.

This strain Remind as the above mycological properties "in the gram-negative rod bacteria, it does not form spores, in absolute aerobic, Ru mosquito cod over zero and O key shea peptidase positive der" this and a throat force, et al., would Yo this Do bacteria, previous remarks Ru suitable der that you and belonging to the push from one Domu na scan the genus According to himself the Bergey 's Manual. Its this in the present strain and the of Bergey 's Manual described the death of Yu over de mode na scan that Kusasu to the genus 2 7 of the species and the ratio 铰 to this and tried to filtration, this strain is te down bra click staining except that Ru Oh positive and intends line Bergey 's Manual described the death of Yu over de mode Na vinegar full-O-les-Tsu cell emissions Graphics and you can almost match microbiological properties. As a result of the above or, et al., Strains that due to the present invention is judged and Ru Oh death Yu over de mode + scan ♦ off Ruo Les Tsu cell down the scan novel strain of, the strain that due to the present invention in Yu over Domo Na vinegar off Ruo Les Tsu cell down the scan ♦ 0 - 3 0 strain was named with your good beauty G 1 2 0 1 share. Culture conditions

Culture of the new sheet Yu over de mode na scan bacteria belonging to the genus that by the present invention, also of the Oh Ri cormorant Ru of any such case Purpose manner Te location of the type you good beauty 培菝 conditions including Me the culture. Also, it is grown in Tsu by the culture of that, that Ki out and give Ru this the desired cell amount.

Is as a medium carbon source, but that by the bacterium of the present invention is Ru Oh also possible the power of "use Ru Oh et al Yu Ru cormorants and assimilation, specifically, METHANOL, error data node on Le, acetate, etc. synthetic carbon sources, diacid carbon, etc. inorganic carbon source, yeast et key scan, molasses, Bae flop tons, meat e key scan, etc. natural products, off La click Bok over scan, grayed Le courses, Shi Yu over click and Russia over the scan, etc. of sugars, Soviet Norre bi door over Norre, Ma down two Bok one Norre, raised to the power of capital Lumpur acids, soybean oil, etc. Oh Li one blanking oil fats and oils, click E phosphate, saw blade click acid, Dar co-phosphate, etc. of organic acids such Dogakyo up et al is Ru. In particular, up La click bet one scan, grayed Le courses, push from one click and Russia - scan, etc. of sugars is not the good or.

As well as a nitrogen source, A down mode double-A, A down mode two © salt-free, nitrate, etc. inorganic nitrogen compounds, urea, co-over emissions ♦ scan tape I-loop Lee mosquitoes and foremost, Gaze Lee down , Bae-flops tons, yeast-et-key vinegar, etc. meat e key scan soil exist machine nitrogen-containing substance, the bacteria were or synthesis of various Ru cormorants using 'natural product is Ru possible der use. In particular, G 1 2 0 In the case of one share, the addition of yeast d key vinegar rather than the preferred on the growth, 1 during its 1-8? . The addition of the Ru extremely effective der.

And follow the conventional method of microbial cultures in of, et al., Mosquito Le Shi cormorant salt-free, Na door Li cormorant salt-free, re-phosphate salt of any inorganic salts, Ma down gun, zinc, 鋇, model Li Breakfast Devon , co-bar Norre door, two-Tsu Ke Norre, salts of gold m clauses Russia-time, etc., boric-containing compounds, iodine compounds, bi- data Mi down, respond to need Ryo Mi Roh acid of any trace nutrient sources and this you added Flip is Ki that out.

培簦 temperature 2 0 ~ 4 0 ° C approximately, good or to rather is Ru 2 5 ~ 3 5 ° C about der. p H is 6 ~ 1 ◦ about at the start of cultivation, and preferred rather than the Ru 6.5 to 9.5 about Der. Under the above conditions:! ~ Is aerobically was stirring or three days I O and vibration to intends line the length, et al culture. Culture n method is batch culture, but it may also in the stomach deviation of the continuous gun culture.

Or more of the conditions in the case of outside and in 培筵 is the growth of microorganisms that Do rather than relatively evil, not such hinder a call you cultured outside the children are these conditions.

HY - 1 of production:

That due to the present invention in Yu over Domu na scan bacteria belonging to the genus, the HY - 1 Ri you to have a nature that eggplant production, and between growth that has been Tsugiju, the HY - to 1, wherein the microorganism synthesized Tsu good, Ru is 蓄稜 in mainly within the bacterial cells. And follow, cultured by that bacterium to the present invention of this, the culture of that or we the HY - 1 One by the and the child you collected - 1 1 - Te HY - is and this you manufacture 1 it can .

The HY - is a good or to have culture conditions 1 production, temperature Doryokuku 2 0 ~ 4 0 ° C, good or to rather than 2 5 ~ 3 5 ° C, p H Chikaraku

6 ~:.. L 0, good or to rather 6 5-9 5, in Ru Oh. Between microorganisms that by the present invention that has continued growth is the HY - 1 continue only that produced the. And follow, such is 增殖 the by One in the cells in culture in normal medium said although al HY - that Ki out and this you manufacture one. On the other hand, that due to the present invention in Yu over Domu na scan bacteria of the genus, and Oh Ru this a sufficient amount of that exist in the substrate assimilative-carbon compound as a condition, the microorganism is you growth small Do rather than one also of the essential components of eyes, good or was rather the nitrogen your good beauty or is re-down, if you cultured in a medium under that restrict, is high have Les bell in La and until in synthesizing the polymer, it accumulates (Yo I Do HY this - see below experimental examples in its one to 1 good or to have medium composition to produce). Is Oh Tsu to the new m strain that by the present onset Akira, the Ru have use sugars as the assimilable carbon source is good or tooth rather, that by the present invention strains in the sugars as a carbon source its a child in the molecule that forms produce a co-po Li et scan Te le that having a double bond Ru seems that the specific child.

By that HY to the present invention - is Tsu Oh to 1 of the production method, is a bacteria that was 增殖 was filtration or in the normal culture land Tsu by the ordinary solid-liquid separation means Do you Yo of centrifuge separation recovered, HY to further cells of this - you 培薆 in 1 Me producing other media, two-step culture H and is not to good or. Name your, temperature your good beauty p H at the time of the 培藤 the latter stage of this is not good in Tsu Oh the same as the coagulation front of the culture. 8 said of good cormorant culture or et al., Including the cultured cells to, then HY - 1 you collected. The HY - 1 mainly either with this Ru accumulated in microbial cells, et al., Culture or et cells was separated, cells of that or we HY -. 1 a have to preferred for that release single is . Cultures or isolated cells or these H 'Y - Isolation of 1, after washing the cells, lyophilized, HY Ri by the click B port E Lum after their - 1 extracted, ¾ solvent (e.g., water, a Le co Lumpur) If you precipitate recovered have use the 'in Tsu by the O methods have to preferred the intends line. Shi two-over-de-Mo Na vinegar off Norre au-les-Tsu cell down vinegar 0 - 3 0 shares,

5 L Lee following composition-out in the triangle off La scan co-with volume (distilled water 1 L Oh r ') * the medium implanted in 1 L that Yusuke, p H 7. 5,

2 4 hours at U, was aerobically oice bovine culture growth. I over the scan Bok et key scan: 1 0 g

! 1 ^ off Bok emissions: 1 0 g

Bae two - Γ "■: 5 g

: 5 g

One technique centrifugation the bacterial cells to (6 0 0 0 rp ra, 2 0 min) by Ri recovered in, 5 L Lee the following composition of the board can meet many in the triangle off La scan co (distilled water 1 L Oh was Ri j implantation in the medium 1 L that having a said similarly to p H 7. 5, 3 0 ° C for 2 4 hours, the gel courses 2 aerobically oice cormorant culture 0 g

^ HP 0 A one g 9

N a HP 4 • 2 H 0 1 g

N a C 1 1

M g S 0 H 0:. 0 5

4 · 7 g

Trace 兀素 solution: 1 0 ml

In trace elements solution, the following composition (INHC 1

That having a 1 L Oh was Ri) is also of the Ru Oh.

M n S 0

4 ♦ 4 H one 0:. 1 9 8 g

Z n S 0 H 0:. 0 2

4 * 7 9 g

. C u C 1 2 - 2 H two 0: 0 1 7 g

C a C 1 2 ♦ 2 H 0:. 1 4 7 g

C o S 0 H 9 0: . 2 8

4 - 7 1 g

F e S 0 H ^ 0:. 2 7 8 g

4 ♦ 7

The cells centrifuged (6000 rpni, 2 Om in) Tsu by the was taken, and Kiyoshi in § Seto, after the freeze-dried, 1 2 o'clock question-click opening ports in the Soviet click Threshold Level one Extraction unit There row sail Le beam extractions, extract out product in 2 0 times the amount of the main evening Roh - pressure to give a Norre, colorless, HY Ru Oh transparency of viscous - 1 was precipitated recovered. As a result, the cells 4. And 6% (weight / weight) polymer of including this is shown. Profile tons a or polymer

In Tsu by the two and subjected to the NMR measurement to determine the ratio of the structural unit of the (I) and (II). The results of its is Ru Oh the Ri through Ru is shown in Table 3

The composition of the heavy ^ body is in is et al., METHANOL Li Shi scan Ru is generated Tsu by the main Chi Le one 3 - the human mud key sheet acids in high-performance liquid Russia Ma Bok grayed La off I HPLC) and Tsu good to 则定, was or, in its structure Nitsu of inclusions, METHANOL Li Shi scan Ru is generated Tsu by the main switch Norre - the human mud key sheet acids in HPLC - 3 after prep purified Tsu, Yui粜 of its determined Ri by the NMR and GC Ma scan spelling click door Lumpur analysis Ru der Ri through Ru is shown in table 4.

The molecular weight of the heavy base body was determined Tsu by the Geruro over-law had use the HPLC of the following conditions is found. I had use of the port re-scan switch-les-in as the standard substance.

Equipment: TOSOHLC - 8 0 2 A

De I Te click Turn-: RI

Solvent system: click B B E Norre-time 1 0 0? . , 1 m 1 / mi n

Mosquito ram: had for four following a series Nitsu brew.

TSK gel G 2 0 0 0 H

TSK gel G 3 0 0 0 H

TSK gel GMHXL

TSK gel GMHXL

Et molecule S is Ri Ah to 1 5, 4 0 0 1 7 0 0 0 0 range, a number average molecular weight of Tsu 1 1 2 0 0 0 der.突施 Examples 2 ~ S

It said the production of cells in the culture you good BiShigeru Taytay was Tsu line as the Example 2 to 8 under the same conditions as in Example 1.

Example 9 ~: L 2

Other than at the time of culture ¾ had use the Shi Mu Yi Bo triangle off La scan call the actual Example 1 and in to the real 施例 9-1 2 the production of 培蓰 your good BiShigeru ^ body's cells similar was Tsu line was. Example 1 3, 1 4

Grayed Le courses to exchange e and Yu over click and Russia over the scan, except that had use between emissions node on be performed in the production of Good Example 1 in the same manner as in cell culture beauty heavy Taytay It was Tsu line as an example 1 3 your good beauty 1 4. Example 1 5

Push from one de mode na scan ♦ full-O-les-Tsu cell down the scan 'G 1 2 0 1 share a 5 L I (Ri was Oh distilled water 1 L) the following composition in-out triangle off La scan co-with the ball Yu medium planted appraised write to 1 L you, p H 7. 5,

3 0 ° C between 2:00 4 was aerobically oice bovine culture growth.

I one scan Bok et key scan: 5 0 g

Po Li Bae-flops t: 5 g

Meat E key scan: 3 g

Group courses: 5 g

One trick the cells were recovered Ri by the centrifugation (6000 rpm, 2 Ora in) to, that Yusuke the following composition in a 5 L I-out with ball triangle off La scan child (distilled water 1 L Oh was Ri) medium 1 L planted appraised write to, in the same manner as described above

PH 7. Ϋ, 7 2 hours at 3 0 ° C, was oice cormorants cultured aerobically.

Grayed Le courses: 7 5 g

K ^ HP 0:. 2 1 g

Four

N a H single P 0 2 H 0: 1

4 9

N a C 1: 1 g

M g S 0, ♦ 7 H 9 0:!. 0 5 g

Traces of the original purple solution: 1 0 in 1 while - in trace element solution NHC 1

That having a 1 L Oh was Ri)

M n S 0 4 H single 0 9 8 g

4 ♦

Z n S 0 7 H one 0 0 2 9 g

Four ·

C u C 1 2 * 2 H 2 0 0 1 7 g

C ac 1 2 · 2 H one 0 1 4 7 g

C os 0 7 H 0 2 8 1 g

4 ♦

F es 0 7 H two 0 one 7 8 g

Four ·

The cells centrifuged (6000 rpiii, 20rai n) were collected Tsu by the, washed with § Se Bok down, after lyophilization, 12 hours click B port E in source click Threshold Level over 抽岀 device It performed Le beam extraction, the extract 2 0 times the amount of METHANOL addition to colorless, transparent viscous product was fold-out, one had to removal of the solvent under reduced pressure a solid (full Lee Le It was recovered 1 - HY-free form). As a result, the cells 1 8.5? . :: and containing the heavy ^ body of (heavy Roh m) has been shown. Or a heavy table body was determined Tsu by the and the child to be subjected to profile tons NMR measurement and [I) the ratio of the structural units of (H). Yui粜 of that is Ru der Ri suitable that will be shown in Table 3.

The composition of is found in the polymer, METHANOL Li Shi scan main switch Le Ru generated Tsu by the -3 - arsenide mud key sheet acids and high-performance liquid b Conclusions grayed La off I one (HPLC) Tsu by the human mud key sheet acids in HPLC - measured Tsu by the, or, structure information about inclusions, METHANOL Li Shi scan Ru is generated Tsu by the main Chi-le-3 after Te preparative purification was determined Ri by the NMR and GC Ma Status This Bae click door Le minute fold. The results of its is Ru Oh the Ri through Ru is shown in Table 4.

Wherein the molecular weight of the polymer was determined Me in Tsu by the gel filtration law had use the HPLC of the following conditions is found. I had use of the port re-scan switch-les-in as the standard substance.

Equipment: TOSOHLC - 8 0 2 0

De I Te-click data one: RI

Solvent system click B port E Le beam 1 0 0% 1 πι 1 / mi n

Mosquitoes ram following two had for Less One such are in the series.

TSK gel GMHXL

TSK gel GMHXL

The resulting et molecules m Ri Ah to 1 0, 6 0 0 7 6 7 0 0 0 range of the number average molecular weight was Tsu Ah at 8 0, 6 0 ◦.

Embodiment 6 1 9

Said Tsu rows producing cell culture Contact good beauty polymer in Example 1 6 -1 9 under the same conditions as in Example 1 5.

HY in the same manner as 突施 Example 2 1 4 Contact good beauty 1 6 1 9 resulting et microbial cells or found in Example 1 Contact good beauty 1 5 above - 1 isolate, As a containing Yuryou your good beauty composition was determined Me. As a result the Ru Oh the Ri through Ru is shown in Table 3 below. Table 3

Heavy base body content 9. Ratio structure of the structural unit (I)

1 4, 6 SO. 1 19. 9

- 2 79.7-time U. -?

3 丄 u, 丄 SO. 6 丄,

. 4 1 丄 one 81. 5 O 丄 C>, -> r 16, 0 79. 6 20. 4

丄 and j »η Li 79. 9 n U ♦ 丄 1

14, 1 79.8 20.2

1 7 75.9 4-丄 η J. U 93. 3 D · / nn 91. 7 «re nn U 4 * 4 91. 7 O, J

: 0.01 97.2 2.8

3.6 79.0 21.0

2. S 78. 0 22. 0

IS. 5 94. 5 5. 5 Bok, 1. 0 92. 4 7. 6 i 15. 1 94. 1 5. 9, '12. 4 94. 5 5. 5 C 13. 6 92. 8 7. 2 example 2, 1 3, 1 4, 1 5 this filtrate that the II combined resulting et a in Tsu by your good beauty 1 8 is analyzed al, the composition of their being these polymers below and of the Son and of the Ru Oh in your Ri's described is shown in Table

Table 4

Mol% of the monomers in the polymer

Example

AB 1 A2 B 2 A3 B 3 A4

1 4.7 6.1 39.3 9.7 36.1 4.1 - one 14. One 10. 6 47. 0 7. S 20. 4

13 3.3 57.3 14.4 21.7 three -

14 9.8 8.7 51.5 13.3 16.7

15 28.3 52.2 5.5 10 0 4.0

18 19.5 69.4 5.5 5.6

In Table, A 1 ~ A 4 represent the following structures

A 1: (one to II) 4 Mr. α · ^

1

0CH-CH C0

B 1 CH CH = CH (CH ) 3 CH 3 OCH - CH single CO -

A2 (CH single) ^ CH ^ OCH- CH single CO B 2 CH 9 CH = CH (CH single) 5 CH

0CH-CH C0-

A3 Mr. xi one) one gCH

OCH - CH 9 CO

B 3 CH one CH = CH (CH) 7 one CH

OCH- CH one CO-

A 4: (CH one) one 丄 Q CH

One OCH- CH single CO- Example 2 Y

[Rho Eta beta (Sigma Co., Cat o P-8150..) And, said HY obtained in real Example 1 - a 1, click B port ho le in spite that will be shown in Table 5 follows It was dissolved in arm, after good Ku combined to obtain a full I Lum like molded product the solvent was evaporated. A full I Lum of this 7 0. During-out 2 B in C, and was heated crystallization.

Two Rabbit to have One to the port Li Ma one-flops down de not I Noremu shape was obtained, in accordance with JISK 7 1 1 3, elongation degree, to measure the breaking strength your good beauty turbocharger emissions gain rate. The results of that, the Ru der Ri suitable that will be shown in Table 5. Table 5

p HB · HV - 1 mixing ratio (weight ratio)

P Fibers 50: 1 40: 1 20: 1 10: 1 6 1 4: 1 3: 1 2: 1 elongation degree

4.6 4.4 6.8 10.0 14.8 64.0 133.6

(%)

Breaking strength 1.1 1.1 1.0 1.0 0.8 0.4 0.3 0.3 0.2 (kg)

Yangu rate

114 114 95 51 39 34 31 25 14 (kg / mm 2) Example 2 1

HY obtained in Example 1 5 - 1 was dissolved in click B port ho le beam and the solvent was evaporated and the full I le arm-like molding product. A full Lee Norre-time of this one 8 hour left solvent under vacuum and cormorants this was divided into fully ί ': the port Li Ma over of ί was full I-le-time shape, the Soviet Union re-menu tio as a down ♦ key catcher scan support down pull-prepared in my method, follow the JISK 7 1 1 3, was Haka疋 the breaking strength and the Bi Naka degree o

Also before HY obtained in d Example 1 5 - 1 was dissolved in click B B E Honoré arm, the solvent was evaporated and the full I le arm-like molding product, one hour 8 vacuum under allowed to stand for 2 0 0 arsenide over door-flops of the scan machine also of the was dividing the solvent completely. Was heated forces <et 5 seconds flop Les scan in C, and is are in Chi's other liquid nitrogen Motochu, and left one hour 8 at room temperature is al, the full Lee Honoré beam shape had to try this the port re M a, and the sub emission pull-produced in main Le Bok-click E down Chi method in accordance with JISK 7 1 1 3, was measured elongation degree of breaking strength.

Result of this is found that Ru shown by Ru through Ri der in Table 6.

Table 6

HY-1 of the physical properties

Growth level (¾) cutting the congregation (kgZ eyebrows :)

H Y- 1 (solutions ♦ cast) 4 1 2- 5 Q _ 0. 2

HY - 1 (melt ♦ quench) - availability of on 64 0 0.6 industry

The present invention also that provide co-po Li et scan Ter that have a novel biodegradable of the Oh is, this to be of particular, co-po Li et vinegar combines the biodegradability and Flexibility Te Rudea Ru this and force the et variety objects of - the bra scan switch click material and then is that Ki out and this Ru physicians use to et you, co Po Li et scan ether of the present invention other biodegradable polymer of ^ goods and Breakfast Les emissions dos Ru this and I Resona in addition to that Ki out and the child that to improve the properties of the polymer of base material in, molded in various quarters Muraryo this and force also has the mechanical strength Ru cormorant Re et al have use as a, 禾 U river field La Seo cormorant by example have a wide.

Claims

Asked of range
1. That have a 5 0, 0 0 0 or more structural units of the general formula that will be Table (1) The number average molecular weight or et ing the structural units that will be tables in the following general formula (I) , co-po Li et scan Te le.
(CH one) - ^ - CH 2
One OCH- CH single CO (I)
CH one CH = CH (CH one) Y CH
OCH CH single CO (II)
(In the formula, X your good beauty Y 0 to: an integer of I 6.)
. 2 is te down blanking rack positive staining of the city Yu over de mode na scan * Full O Les Tsu cell down vinegar 0 - 3 0 shares.
3. Is te down blanking rack staining positive push from one de mode na vinegar, full-O-les-Tsu cell down the scan · G 1 2 0 1 share.
4. Shi Yu over de mode belong to Na scan genus, culturing the bacteria that have a capacity that forms produce a co Po Li et scan Te le according to claim 1, culture
A 5έ product or al i¾ Motomeko 1 in this you collect co Po Li et scan Te le of Ki载 and Toku徵 method for producing a co-Po Li et scan Te le according to claim 1.
5. ¾ bacteria force "Shi Yu over de mode Na vinegar off Norre au-les-Tsu cell down the scan ♦
0 - 3 Ru Oh 0 strain, process of claim 4.
6. Bacterium force "Shi Yu over de Mo na scan 'off Norre au-les-Tsu cell down vinegar
G Ru 1 2 0 1 Kabudea process of claim 4.
. Ding TsumeMotomeko 1 and co port re es ether according - ing contain other biodegradable polymers of ^ things, port Li Ma-loop les down mode.
. S said other raw 'degradable polymer compounds port Li one 3 - arsenide mud key sheet Petit Le chromatography preparative (P Eta B) Ru der, port Li Ma-loop les down de of claim 7 .
9. TsumeMotomeko 1 ing include co Po Li et scan Te le according, minutes of ¾ flexibility imparting agent molecules.
PCT/JP1992/000732 1991-06-07 1992-06-05 Biodegradable polymer, production thereof, and use thereof WO1992021708A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP16383191 1991-06-07
JP3/163831 1991-06-07
JP27196791 1991-09-24
JP3/271967 1991-09-24

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0526850A2 (en) * 1991-08-03 1993-02-10 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Copolymer and method for production thereof
US5489470A (en) * 1994-01-28 1996-02-06 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers
US5498692A (en) * 1994-01-28 1996-03-12 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers
US5502116A (en) * 1994-01-28 1996-03-26 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers of 3-hydroxyhexanoate
US5614576A (en) * 1994-08-12 1997-03-25 Minnesota Mining And Manufacturing Company Poly(β-hydroxyorganoate) pressure sensitive adhesive compositions
EP0726325A3 (en) * 1994-11-28 1998-02-04 Director-General Of The Agency Of Industrial Science And Technology Enzymatic decomposition of polycarbonate resin
US5990271A (en) * 1994-01-28 1999-11-23 The Procter & Gamble Company Films and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate comonomer units
US6077931A (en) * 1998-12-21 2000-06-20 The Procter & Gamble Company Biodegradable PHA copolymers
US6143947A (en) * 1996-01-29 2000-11-07 The Procter & Gamble Company Fibers, nonwoven fabrics and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate
US6160199A (en) * 1998-12-21 2000-12-12 The Procter & Gamble Company Absorbent articles comprising biodegradable PHA copolymers
US6174990B1 (en) 1998-12-21 2001-01-16 The Procter & Gamble Company Films comprising biodegradable PHA copolymers
US8728778B2 (en) 1998-03-30 2014-05-20 Metabolix, Inc. Microbial strains and processes for the manufacture of biomaterials

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58212792A (en) * 1982-04-05 1983-12-10 Ici Ltd Polymer composition derived from microorganism
US4468461A (en) * 1981-12-10 1984-08-28 General Electric Company Microbiological removal of chromate from contaminated waste water

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4468461A (en) * 1981-12-10 1984-08-28 General Electric Company Microbiological removal of chromate from contaminated waste water
JPS58212792A (en) * 1982-04-05 1983-12-10 Ici Ltd Polymer composition derived from microorganism

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0526850A2 (en) * 1991-08-03 1993-02-10 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Copolymer and method for production thereof
EP0526850A3 (en) * 1991-08-03 1994-06-22 Kanegafuchi Chemical Ind Copolymer and method for production thereof
US5489470A (en) * 1994-01-28 1996-02-06 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers
US5498692A (en) * 1994-01-28 1996-03-12 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers
US5502116A (en) * 1994-01-28 1996-03-26 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers of 3-hydroxyhexanoate
US5602227A (en) * 1994-01-28 1997-02-11 The Procter & Gamble Company Biodegradable copolymers
US6027787A (en) * 1994-01-28 2000-02-22 The Procter & Gamble Company Films and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate comonomer units
US5618855A (en) * 1994-01-28 1997-04-08 The Procter & Gamble Company Biodegradable copolymers and plastic articles comprising biodegradable copolymers
USRE36548E (en) * 1994-01-28 2000-02-01 The Procter & Gamble Company Biodegradable copolymers
US6013590A (en) * 1994-01-28 2000-01-11 The Procter & Gamble Company Fibers, nonwoven fabrics, and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate
US5990271A (en) * 1994-01-28 1999-11-23 The Procter & Gamble Company Films and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate comonomer units
US5753364A (en) * 1994-08-12 1998-05-19 Minnesota Mining And Manufacturing Company Poly(β-hydroxyorganoate)pressure sensitive adhesive compositions
US5614576A (en) * 1994-08-12 1997-03-25 Minnesota Mining And Manufacturing Company Poly(β-hydroxyorganoate) pressure sensitive adhesive compositions
EP0726325A3 (en) * 1994-11-28 1998-02-04 Director-General Of The Agency Of Industrial Science And Technology Enzymatic decomposition of polycarbonate resin
US6143947A (en) * 1996-01-29 2000-11-07 The Procter & Gamble Company Fibers, nonwoven fabrics and absorbent articles comprising a biodegradable polyhydroxyalkanoate comprising 3-hydroxybutyrate and 3-hydroxyhexanoate
US8748139B2 (en) 1998-03-30 2014-06-10 Metabolix, Inc. Microbial strains and process for the manufacture of biomaterials
US8728778B2 (en) 1998-03-30 2014-05-20 Metabolix, Inc. Microbial strains and processes for the manufacture of biomaterials
US6160199A (en) * 1998-12-21 2000-12-12 The Procter & Gamble Company Absorbent articles comprising biodegradable PHA copolymers
US6174990B1 (en) 1998-12-21 2001-01-16 The Procter & Gamble Company Films comprising biodegradable PHA copolymers
US6569990B1 (en) 1998-12-21 2003-05-27 The Procter & Gamble Company Plastic articles comprising biodegradable PHA copolymers
US6077931A (en) * 1998-12-21 2000-06-20 The Procter & Gamble Company Biodegradable PHA copolymers

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