CN104558491A - Preparation method for polyurethane material capable of promoting growth of endometrial tissue - Google Patents

Preparation method for polyurethane material capable of promoting growth of endometrial tissue Download PDF

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Publication number
CN104558491A
CN104558491A CN201410853014.8A CN201410853014A CN104558491A CN 104558491 A CN104558491 A CN 104558491A CN 201410853014 A CN201410853014 A CN 201410853014A CN 104558491 A CN104558491 A CN 104558491A
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hours
preparation
mixture
polyurethane material
polyurethane
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刘芳
胡琛
徐大宝
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Central South University
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Central South University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • C08G18/3278—Hydroxyamines containing at least three hydroxy groups
    • C08G18/3281—Hydroxyamines containing at least three hydroxy groups containing three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Materials For Medical Uses (AREA)

Abstract

The invention discloses a preparation method for a polyurethane material capable of promoting the growth of endometrial tissue. The preparation method comprises the following steps: (1) dropwise adding 0.1-0.3 wt% of triethanolamine into a polytetramethylene glycol and butanediol solution to obtain a mixture I, heating the mixture I to 60-90 DEG C for a 3-6 hours' reaction, and stopping heating; (2) dropwise adding 0.1-10 wt% of an estrogen into the heated mixture I within 30-60 minutes under the condition that stirring is carried out continuously to obtain a mixture II; (3) adding 1,4-butanediol into the mixture II under the condition that stirring is carried out continuously for a 4-6 hours' continuous reaction; (4) after precipitation and filtration, carrying out washing for 3-5 times with distilled water, placing the washed mixture III at 10-30 DEG C for 12-24 hours, carrying out vacuum drying at 50-70 DEG C for 24-72 hours, and carrying out compression molding to obtain the polyurethane material. Through the adoption of the preparation method, modification can be realized during polyurethane polymerization, and an estrogen release system can be formed in polyurethane, so that polyurethane can promote the growth of the endometrial tissue.

Description

The preparation method of the polyurethane material organizing inner membrance to grow can be promoted
Technical field
The present invention relates to a kind of preparation method that can promote the polyurethane material organizing inner membrance to grow.
Background technology
In China, due to special national conditions, artificial abortion and induced labor patient more, add the hysteresis quality of gynecopathy therapeutic, make the risk of Asherman's syndrom to occur up to more than 30%.Asherman's syndrom is the pathological phenomenon due to the impaired rear forming section of uterine endometrium or whole Asherman's syndrom, it is one of gynecological clinic common disease, clinical signs is amenorrhoea or MBV minimizing, periodic abdominalgia and gestation exception etc., if obstinate even can have a strong impact on female fertility ability, cause infertile.The Asherman's syndrom of more than 90% is because operation Endometrial destroys, and has damaged inner membrance stratum basale, has caused uterine endometrium reproducibility obstacle.Only a few causes owing to infecting.At present, under hysteroscope, Asherman's syndrom exclusion has become the standard method for the treatment of Asherman's syndrom, but postoperative uterine endometrium regeneration slowly, (Postoperative recurrent rate that is slight and moderate is 1/3 to the easily adhesion again of uterine cavity after separation, severe person is 2/3), need again to check hysteroscope operation to be about 2-4 time, therefore Asherman's syndrom, particularly severe Asherman's syndrom operative results poor effect.Now clinically after Asherman's syndrom exclusion, in uterine cavity, indwelling metal intrauterine contraceptive loop prevents adhesion again, but metal intrauterine contraceptive loop is a kind of contraceptive device, the Asherman's syndrom patient of 90% has fertility requirement, its psychology is difficult to accept indwelling metal intrauterine contraceptive loop in uterine cavity, and the limited area of metal intrauterine contraceptive loop, be difficult to the Asherman's syndrom prevented in various degree.Many domestic and international clinical research personnel recognize for after Asherman's syndrom exclusion, and effective Film with Preventing Adhesion recurrence has great scientific research value and potential applicability in clinical practice.
Urethane (be called for short PU) is the polymkeric substance be made up of polyisocyanates and polyether glycol or the raw material such as chainextender or linking agent such as polyester polyol and/or small molecule polyol, polyamine or water.By feed change kind and composition, product form and performance thereof can be changed significantly, obtain from softness to hard the finished product.Urethane has the advantages such as biocompatibility is good, excellent in mechanical performance, easy-formation are processed, performance is controlled, is widely used in biomedical sector.From the 1950's urethane first Application in biomedicine, over more than 50 year, urethane purposes is medically increasingly extensive, as artificial valve, artificial heart and supplementary unit thereof, artificial blood vessel, interposing catheter, joint prosthesis, artificial cartilage and artificial ureter etc.But up to now, do not find that urethane is at metrosynizesis Post operation, the application of anti effect aspect in endometrial growth process.
Oestrogenic hormon is that a class has extensive bioactive sterid, it not only has the physiological action promoting and maintain female sex organ and secondal sexual character, and the metabolism of Endocrine system, cardiovascular systems, human body, the growth of bone and maturation, each side such as skin all have obvious impact.In uterus in film post operative recovery procedures, usually need oral estrogen to accelerate inner membrance growth, but also can cause damage to other organs of health simultaneously.How oestrogenic hormon modification is combined with urethane, makes this material in human uterine, can promote that the oestrogenic hormon organizing inner membrance to grow becomes the focus of research by sustained release.
Summary of the invention
Main purpose of the present invention is to provide a kind of preparation method that can promote the polyurethane material organizing inner membrance to grow.
In order to achieve the above object, the present invention includes following steps:
1) in polytetramethylene glycol and butanediol solution, drip the trolamine of 0.1 ~ 0.3% (weight), be warming up to 60 ~ 90 DEG C, react 3 ~ 6 hours, stop heating;
2) drip 0.1 ~ 10% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 30 ~ 60 minutes;
3) add BDO again, Keep agitation, continue reaction 4 ~ 6 hours;
4) precipitate, filter rear distilled water wash 3 ~ 5 times, place 12 ~ 24 hours, 50 ~ 70 DEG C of vacuum-drying compression moldings after 24 ~ 72 hours at 10 ~ 30 DEG C.
Adopt technique scheme, modification in urethane polymerization process can be realized and make oestrogenic hormon in urethane, form a kind of delivery systme, thus make urethane have promote organize inner membrance to grow function.When being made into Asherman's syndrom control device, preventing uterine endometrium again while adhesion, endometrial growth can be promoted.In addition, the physical and mechanical properties of modified polyurethane material can meet the requirement of use.
Embodiment
Embodiment 1:
In polytetramethylene glycol and butanediol solution, drip the trolamine of 0.1% (weight), be warming up to 90 DEG C, react 3 hours, stop heating; Drip 10% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 60 minutes; Add BDO again, Keep agitation, continue reaction 5 hours; Use distilled water wash 5 times after precipitation, filtration, place 12 hours, 65 DEG C of vacuum-drying compression moldings after 48 hours at 20 DEG C.The polyurethane material shore hardness of preparation is 50.6, and during extension elongation rate 200%, tensile strength is 6.23MPa.Implanted and carried out in the female rabbits palace of endometrial surgery.Post operation, endometrium thickness 5.48mm; After 10 days, endometrium thickness is recovered to a certain degree, is 9.45mm.
Embodiment 2:
In polytetramethylene glycol and butanediol solution, drip the trolamine of 0.3% (weight), be warming up to 60 DEG C, react 4 hours, stop heating; Drip 0.1% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 30 minutes; Add Isosorbide-5-Nitrae one butyleneglycol again, Keep agitation, continue reaction 4 hours; Use distilled water wash 3 times after precipitation, filtration, place 24 hours, 70 DEG C of vacuum-drying compression moldings after 24 hours at 10 DEG C.The polyurethane material shore hardness of preparation is 44.8, and during extension elongation rate 200%, tensile strength is 5.06MPa.Implanted and carried out in the female rabbits palace of endometrial surgery.Post operation, endometrium thickness 5.49mm; After 10 days, endometrium thickness is recovered to a certain degree, is 6.20mm.
Embodiment 3
In polytetramethylene glycol and butanediol solution, drip the trolamine of 0.2% (weight), be warming up to 70 DEG C, react 6 hours, stop heating; Drip 7% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 45 minutes; Add BDO again, Keep agitation, continue reaction 6 hours; Use distilled water wash 4 times after precipitation, filtration, place 18 hours, 50 DEG C of vacuum-drying compression moldings after 72 hours at 30 DEG C.The polyurethane material shore hardness of preparation is 47.5, and during extension elongation rate 200%, tensile strength is 5.62MPa.Implanted and carried out in the female rabbits palace of endometrial surgery.Post operation, endometrium thickness 5.48mm; After 10 days, endometrium thickness is recovered to a certain degree, is 8.45mm.
Embodiment 4:
In polytetramethylene glycol and butanediol solution, drip the trolamine of 0.3% (weight), be warming up to 60 DEG C, react 3 hours, stop heating; Drip 0.8% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 30 minutes; Add BDO again, Keep agitation, continue reaction 4.5 hours; Use distilled water wash 3 times after precipitation, filtration, place 12 hours, 50 DEG C of vacuum-drying compression moldings after 24 hours at 10 DEG C.The polyurethane material shore hardness of preparation is 45.9, and during extension elongation rate 200%, tensile strength is 5.63MPa.Implanted and carried out in the female rabbits palace of endometrial surgery.Post operation, endometrium thickness 5.49mm; After 10 days, endometrium thickness is recovered to a certain degree, is 7.10mm.

Claims (1)

1. one kind can promote the preparation method of the polyurethane material organizing inner membrance to grow, it is characterized in that, comprise the following steps: the trolamine 1) dripping 0.1 ~ 0.3% (weight) in polytetramethylene glycol and butanediol solution, be warming up to 60 ~ 90 DEG C, react 3 ~ 6 hours, stop heating; 2) drip 0.1 ~ 10% (weight) oestrogenic hormon, Keep agitation in adding procedure, dripped off at 30 ~ 60 minutes; 3) add BDO again, Keep agitation, continue reaction 4 ~ 6 hours; 4) precipitate, filter rear distilled water wash 3 ~ 5 times, place 12 ~ 24 hours, 50 ~ 70 DEG C of vacuum-drying compression moldings after 24 ~ 72 hours at 10 ~ 30 DEG C.
CN201410853014.8A 2014-12-25 2014-12-25 Preparation method for polyurethane material capable of promoting growth of endometrial tissue Pending CN104558491A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101873850A (en) * 2007-11-22 2010-10-27 拜耳先灵医药公司 Vaginal delivery system
CN101977651A (en) * 2008-01-25 2011-02-16 犹他大学研究基金会 Linear order release polymer
CN102120059A (en) * 2011-03-11 2011-07-13 东南大学 Medicinal stent-graft for preventing and treating intrauterine adhesion

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101873850A (en) * 2007-11-22 2010-10-27 拜耳先灵医药公司 Vaginal delivery system
CN101977651A (en) * 2008-01-25 2011-02-16 犹他大学研究基金会 Linear order release polymer
CN102120059A (en) * 2011-03-11 2011-07-13 东南大学 Medicinal stent-graft for preventing and treating intrauterine adhesion

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
罗致诚: "《中国医学百科全书 生物医学工程学》", 30 November 1989, 上海科学技术出版社 *

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Application publication date: 20150429