CN1131085A - 热塑性聚酯系树脂发泡体的连续制造方法及制造装置 - Google Patents
热塑性聚酯系树脂发泡体的连续制造方法及制造装置 Download PDFInfo
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- CN1131085A CN1131085A CN95119482A CN95119482A CN1131085A CN 1131085 A CN1131085 A CN 1131085A CN 95119482 A CN95119482 A CN 95119482A CN 95119482 A CN95119482 A CN 95119482A CN 1131085 A CN1131085 A CN 1131085A
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- thermoplastic polyester
- polyester resin
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Images
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Abstract
热塑性聚酯系树脂发泡体的制造方法及装置,包括热塑性聚酯系树脂供给到双轴挤出机,在双轴挤出机内加热熔融树脂,从双轴挤出机的排出孔减压吸引除去树脂中的水分,接着向树脂中压入发泡剂,压出后制成发泡板,而后将发泡板成型,切断后,分成成型体和成型余料,粉碎成型余料,将得到的粉碎物作为回收品加到双轴挤出机供给再使用。
Description
本发明涉及热塑性聚酯系树脂发泡体的连续制造方法及其制造装置。特别是涉及重新使用由再循环的热塑性聚酯系树脂构成的回收品。
热塑性聚酯系树脂(以下称为PET)是一种透明的,耐热性、耐化学药品性、耐气候性优良,而且抗拉强度等机械特性也优良的工程塑料。因而此树脂通过吹塑成形而广泛地利用在大量生产液体容器方面。此外,PET是结晶性的树脂,难以发泡的树脂,但是在美国专利5000991号说明书中记载了添加交联剂将其挤出使其发泡作成发泡板,再将此发泡板热成形为容器,利用在电子加热器上的加热烹调的耐热容器方面。
可是这些容器作为包装商品消费后没有其他用途。而且,这些使用后的大量容器的再循环系统是与环境问题密切相关,各国都制定了法律。因此,迫切要求能有效地重新使用这些再循环下来的容器。
此外,PET具有吸湿性,若将含有水分的树脂直接供给加热成高温的挤出机时,由于加水分解会产生劣化,所以必须干燥到水分为300PPM以下。例如在WO95/15257号说明书中公开了粉碎PET发泡板的加工余料,再使用的方法。而且予先对粉碎品进行干燥。其干燥方法是将通常粉碎品加入干燥机,在其中一边循环干燥的空气,一边进行短时间的加热。发泡体的粉碎品体积膨大,不但要使用大型干燥机,而且加热时间至少需要数小时,所以这种干燥方法复杂,迫切要求干燥方法简化。另外,干燥状态不均匀,引起供给原料的变动。
在特公昭60-54850号公报中,公开了熔融聚苯乙烯系树脂,对挤出机的滚筒进行减压吸引,除去残余单体等的挥发性成分,接着压入发泡剂进行挤出发泡的方法。可是意外地发现将此方法应用在再循环的PET时,可省去PET的干燥工序,在挤出机中用减压吸引可以充分地除去水分,能够稳定地挤出发泡PET未劣化的良质PET发泡体。
本发明的目的是为了解决以往的这些课题,提供使用从大量产生的再循环PET容器的回收品制造优质的PET发泡体的连续制造方法。
本发明其他的目的提供了直接将再循环的PET的非发泡体或者发泡体的粉碎上供给挤出机来连续制造PET发泡体的方法。
本发明的其他目的在于取消PET的复杂干燥工序,提供只对挤出机的滚筒减压吸引除去水分,就能有效地连续制造PET发泡体的方法。
本发明另外的目的在于通过来自挤出机滚筒的减压除去水分,提供在高温挤压时PET不劣化的发泡体连续制造方法。
本发明的另外目的在于提供通过添加交联剂,对劣化的PET改性和制造改善发泡性的PET发泡体的连续制造方法。
本发明的其他目的提供了为实施上述目的,连续制造PET发泡体的装置。
本发明者,为了解决上述目的进行了锐意的研究,结果完成了本发明。
亦即,确定了在挤出机内熔融混炼PET时,不管PET的熔融粘度是否增加,只是通过来自挤出机滚筒的减压吸引,在不劣化条件下可以容易地从PET中充分地除去水分,本发明是基于这些见解而完成的。
本发明的概要包括了热塑性聚酯系树指发泡体的连续制造方法,其特征是向热塑性聚脂系树脂中添加交联剂后,供给到挤出机中,在挤出机内熔融混炼后,在使树脂的重均分子量增加的同时,通过来自挤出机滚筒的减压吸引,除去熔融树脂中的水分,接着向此熔融树指中压入发泡剂作成发泡性熔融树脂,再将其从挤出机中挤出到低压区域进行发泡的方法;它还包括了热塑性聚酯系树脂系树脂发泡体的制造装置,其特征是由在滚筒中与树脂熔融部接触部分具有排气孔的挤出机和在滚筒的中途有发泡剂压入口的挤出机和连接这二个挤出机的连接管和连接上述排气孔的减压装置,以及设置在挤出机前端的摸具而构成的。
图的简单说明
图1是表示本发明发包体制造装置的模型的侧面图、图2是表示本发明另一种发泡体制造装置模型的侧面图、图3是表示本发明其他例模型的侧面图、图4是表示本发明又一例模型的侧面图。
本发明所用树脂是来自新原料或回收品的PET。PET是芳香族的二羧酸和二元醇进行酯结合,生成了高分子量的线性聚酯。作为构成PET的二羧酸,可使用对苯二酸、间苯二酸、萘二羧酸、二苯醚二羧酸、二苯基磺二羧酸、二苯氧基乙烷二羧酸等、作为二元醇,可使用乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、二甘醇等,所以作为PET,可使用这些进行酯结合生成的。另外也可使用在聚合中,聚合后,通过使用交联剂、支链剂,进行改性的PET。
在PET中,优选的是使用聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚萘酸乙二醇酯、聚对苯二甲酸丁二醇酯弹性体、非晶性聚酯、聚对苯二甲酸环己醇酯、及它们的混合物。
另外,作为回收品,是将大量产生的吹塑成形的非发泡饮料水、碳酸饮料、桔汁、酒、化妆品的液体容器等一次性使用的容器进行粉碎的粉碎品、将一次性使用过的包装膜、照相底片切碎的粉碎片。以及热成形PET发泡板,制造成形品时的修整损失的粉碎品。特别是,这些粉碎品若作成通过15mm中孔滤网的大小,就很容易地供给到挤出机中。
回收品与新原料相比,虽然水分含量、分子量分布是各种各样,但本发明对这样的树脂,可以充分地除去水分,而且可以将水分除去到一定量以下。
本发明中,作为PET,可以使用回收品、新原料或它们的混合物。由于回收品一般发生了劣化,分子量变小,因此显示了低熔融粘度,或是非结晶状态。与此相反,新原料一般分子量大,且熔融粘度高。但是,使用这些树脂,为了达到适宜发泡的熔融粘度,在本发明中,可将交联剂添加到树脂或熔融树脂中。而且通过将PET的重均分子量调节成90000~200000,可发泡至3~20倍。该交联剂,也具有支链剂功能。
作为交联剂,可使用已知的各种各样的,例如,多功能环氧化合物、在一个分子中具有二个以上的酸酐基的二酸酐、噁唑啉化合物、多官能异氰酸酯等。在这些之中,从使用的容易性及对人体的卫生方面看,优选的是使用多官能环氧化合物和二酸酐,特别优选的是使用二酸酐。
作为二酸酐,是苯均四甲酸、萘四羧酸酐、二苯甲酮四羧酸酐、环戊烷四羧酸酐。
进而,可以用于本发明的交联剂,是二酸酐开环后,至少1个酸酐基变成为2个羧基的化合物及含有3个以上不含酸酐基的羧酸基的化合物。例如有苯均四甲酸、偏苯三酸、丙三羧酸、苯均三酸、1,3,5苯三酸、没食子酸等。通过用挤出机除去水分,可复活交联作用。这些交联剂从袋中开封后,随着时间的经过,与水分反应的酸酐可以使用,是有价值的。
这些交联剂的优选使用量,相对于PET100重量份,添加0.01~5重量份。
作为交联剂二酸酐为开环物或含有3个以上羧酸基的化合物时,优选的是与其同时并用属于周期表第1族、第2族或第3族的金属化合物。其中,特别优选的是属于第1族或第2族的金属化合物。这些金属化合物可以是有机物,也可是无机物。特别是对于PET100重量份,可添加碳酸钠、碳酸钾、碳酸锂0.01~5重量份。
作为交联剂,二酸酐为开环物或含有3个以上的化合物时,在将PET作成适合发泡的物质时,使用发泡指数的概念是方便的。所谓发泡指数,是通过测定羟基末端对于PET分子的所有末端基的比例和极限粘度而得到的值。PET的特性粘度可通过将0.300g的PET,在140℃下,搅拌溶解在25ml的邻氯苯酚中,在35℃的恒温槽中,用奥斯托瓦尔德粘度计测定该溶液的溶液粘度,而算出。
另一方面,羟基末端基对于PET的所有的末端基的比例计算如下。首先,用下式从上述特性粘度求出数均分子量Mn。
Mn={特性粘度/(3.07×10-4)}1/0.77
接着,从Mn值,从下式,求出每聚合物108g的总末端基数。
总末端基数(eq/T)=108/Mn×2
另外,通过下述方法,求出PET的羧基末端基数。取约100mg的PET,在200℃下,将其溶解在10ml的苄醇中,将该溶液,以苯酚红作指示剂,用1/50当量的NaOH/乙醇溶液进行滴定,算出羧基末端基数。将该值换算成每聚合物108g的羧酸基当量数。最后,通过从总末端基数减去羧酸末端基数,求出羟基末端基。这样,羟基末端基的比例,通过
羟基末端基数÷总末端基数
可以求出。发泡指数,通过
特性粘度×羟基末端基的比例
可以求出。
为了使PET发泡,可选择使用发泡指数为0.4以上的PET,或使用调节到发泡指数达到0.4以上的。
另外,重均分子量Mw,对于PET的发泡性有较大影响。挤出发泡性好,独立气泡性的PET发泡体的Mw是80000~250000,优选的是90000~200000。低于80000时,只能得到2倍以下的低发泡体,若超过250000,发生熔裂(メルトクラクチセヘ),外观变坏。
在此,重均子量Mw是通过将精确称量的PET约5mg,溶解在六氟异丙醇/氯仿等容易的混合溶剂1.0ml中,进而用氯仿,稀释到全量10ml,在溶胶渗透色谱上进行测定。
作为挤出机,由于双轴挤出机,对于不定形的粉碎品咬合好,且与交联剂等混练好,所以挤出量稳定。该双轴挤出机,优选的是使用二根螺旋咬合的形式,特别优选的是使用二根螺旋同方向旋转的。另外,作为挤出量/转速的比,优先的是使用0.28~1.67的,其中,更优选的是使用0.33~1.43的,进而,最优选的是使用0.42~1.25范围内的。在双轴挤出机的滚筒上,在使PET处于正好能熔融的状态的部位,设有排气口。排气口以二个螺旋咬合的部分为中心,在滚筒宽的方向,扩展直到螺旋轴中心线的正上方。
排气口与减压装置连接。若从螺旋侧隔断向排气口进入的空气,驱动减压装置时,在排气口处,优选的产生20Torr以下,特别优选的是产生1.0Torr以下的强减压状态。
压力的变动越小越好,但优选的是9Torr以下,特别优选的是5Torr以下。
在挤出机的树脂供给口,为了进行定量供给,最好设置定量供给器。作为定量供给器,可以使用市售的。市售的定量供给器是通过皮带的移动、弹簧振动或螺旋旋转,可以控制落下的固体量的装置。分别附设定量供给器,最好分别定量供给PET的新原料、回收品和交联剂,但也可通过一个定量供给器,供给予先混合了PET和交联剂的混合物。
在双轴挤出机的前端,通常通过连接管与稳定供给性良好的单轴挤出机连接。在该连接处,也可附设齿轮泵。在单轴挤出机的滚筒途中设有发包剂压入口。从发泡剂压入口,将发泡剂压入滚筒中。在单轴挤压入口,将发泡剂压入滚筒中。在单轴挤出机的螺旋的一部分上,最好设有使块状(ダルメヘヅ)或针状的发泡剂分散的装置。另外,为了使挤出量稳定,螺旋顶端处的计量部分最好长些,计量部分的L/D即长度与直径的比优选的为5以上,特别优先的为7以上,进而,其稳定部分是全螺旋的,最好螺矩及深度不变。
在单轴挤出机的顶端,附设有片、板、异型等其他形状的模具。为了将PET挤出成片,模具具有直线或园环状喷嘴。喷嘴是直线时,可挤出平坦的发泡片,所以只要在平板或辊上进行就可以了,但喷嘴是园环状时,在其顶端,附设园环状的心轴将PET保持成园筒状,进行发包,冷却后,将园筒切开,作成片。
有将这样得到的发泡片继续成形的情况,也有一次将其卷在辊上,暂时放置后,再成形的情况。但其中任何一种情况,都是将发泡片,在加热工序中加热,成为软化状态,在成形工序中挤压成形。加热是将其发包片放入配置多个红外线陶瓷加热器的加热炉中,在此,加热到PET的玻璃转化点(约70~75℃)以上,结晶化温度(约130℃)以下。真空成形的成形模型,可以是凸模型或凹模型中的任何一种组成的,但优选的是由这两种模型组成的。成形的发泡片,有在成形体间设有成形的部分,即成为修整损失部分。
成形了的片,保持成形的形状不变,加热到结晶温度(约130℃)以上、熔点(约250~260℃)以下的温度,进行热固定后,送到修整装置。在此,通过切断,分成成形体及修整余料。就这样制成的成形制品。
然后,将修整余料粉碎。修整余料呈现不规则连续体时,首先,将其切断成短片,将这样得到的短片进行粉碎。粉碎时,使用辊式破碎机、棒磨机、球磨机、锤磨机等。将这样的PET粉碎品通过15mm的冲孔,通过的回收品的挤出机的咬合稳定性特别好。
来自PET发泡片的回收品,由于交联剂而改性,但由于热又产生劣化,具有与聚合物使用的原材料不同的性质。因此,对于回收品,最好再加交联剂。
另外,PET发泡片,若在至少一面上,叠层非发泡薄膜、Al等的金属箔、金属蒸镀薄膜作成叠层发包片,有广泛的用途。在叠层上,有通过热的熔融、通过粘结剂的粘结、通过挤出机的共挤出。作为非发泡薄膜有热塑性聚酯树脂、聚烯经系树脂、聚酰胺系树脂、聚偏氯乙烯树脂、聚丙烯睛树脂、乙烯—乙烯醇共聚体等。这些由于气体屏障性、特别是水蒸气透过性小,所以作为食品容器使用时,食品保存性好。使用AL等的金属箔的叠层发泡片成形的食品容器,即使是多少有污染的发泡片,但渗透盐全被隔断,对收藏的食品没有污染。
本发明中,除了PET、交联剂和发泡剂之外,根据需要,也可使用各种添加物。例如可将含氟树脂的微粉末进行混合,达到补强作用。作为这些含氟树脂(Fluoroplastics),有四氟乙烯树脂(Polytetra+fluoroethylene)、四氟乙烯-六氟丙烯共聚树脂(Fluorinated Ethylene—Propylene Copolymer)、四氟乙稀—氟烷氧乙烯共聚物、三氟氯乙烯树脂(Polychlorotrifluoroethylene)、四氟乙烯—乙烯共聚物(Ethylene—Tetra fluoroethylene Copolymers)、偏氟乙烯树脂(Polyvinylidene Fluoride)、氟乙烯树脂(Polyvinyl Fluoride)等树脂。可添加其他的发泡用成核剂、阻燃剂、抗静电剂、抗氧化剂、紫外线吸收剂、着色剂等。这些添加剂,可从双轴挤出机的供给口,与PET一起加入,可容易均匀地分散在PET中。
作为发泡剂,可以使用已知的各种发泡剂。发泡剂大致可分为物理发泡剂和化学发泡剂,但其中,优选的是物理发泡剂。物理发泡剂进而可分为惰性气体、饱和脂肪族烃、饱和脂环族烃、卤化烃、醚、酮等,在本发明中,也可以使用其中一种。若叙述代表例,作为惰性气体、可使用二氧化碳气、氮气,作为饱和脂肪族烃,可使用丙烷、丁烷,作为饱和脂环族烃,可使用环己烷,作为卤化烃,可使用氯甲烷、四氟乙烷,作为醚,可使用甲基仲丁基醚,作为酮,可使用丙酮。这些可以单独使用,但也可混合使用。
实施本发明的装置,若用附图模型表示其一例时,是图1及图2样的结构。在图1及图2中,1是双轴挤出机,2是挤出机1的顶端,即挤出机的头部;3是连接管;4是单轴挤出机;5是模具;6,7及8是定量供给器;9是PET发泡体;11是排气口;12是树脂供给口或交联剂供给口;13是添加物供给口;14是吸引管;15是真空泵;41是发泡剂压入口;42是发泡剂供给管;43是发泡剂注入设备。
若通过其他例的附图,模拟地表示本发明,如图3及图4所示。在图3中,新原料加入到料斗1中,回收品加入到料斗20中,交联剂加入到料斗2中,它们分别从定量供给装置3及3′,经过原料入口4及4′,投入到双轴挤出机6中。双轴挤出机6具有2个排气口5,从这里进行吸引。在双轴挤出机6中,熔融混炼了的PET,通过齿轮泵7,送入到第2个挤出机8,通过泵9,压入发泡剂,从模具11挤出成园筒状,在园筒状心轴12上进行冷却,通过切割机13进行切割,得到发泡片15。发泡片15通过牵引辊14进行牵引作成辊状。
将辊暂时放置后,送到热粘结装置21中,反卷后,作成发泡片15,发泡片15与非发泡的PET薄膜22贴合,接着,进入加热炉16,在此,进行加热,成为软化状态,在成形装置17中成形,用修整装置18,切断成形体与其余部分,用粉碎机进行粉碎,作成粉末19,送入料斗20,进行再使用。图4表示与图3大致相同的方法,但在图4中,发泡片15,不作成辊,而得到片后,立即送至加热炉16后进行加热,这是与图3方法不同之处。
这样,按照本发明,将由新原料或容积增大的粉碎的回收品组成的PET供给到挤出机,进行熔融混练,从挤出机的滚筒减压吸引除去水分,所以不需要以往的繁杂的干燥工序。特别是将容积增大的发泡体粉碎品可直接送入挤出机,所以不需要大的干燥机,可高效连续地制造PET发泡体。另外,通过从滚筒减压吸引除去水分,在该工序中,PET几乎不产生热劣化。
另外,按照本发明,将PET和交联剂供给到轴挤出机,在挤出机中,熔融混炼,使树脂的重均分子量增加,作成适于发泡的熔融粘度,另外,使劣化的PET改性,可连续地制造优质且高发泡的PET发泡体。
另外,在本发明中,使用双轴挤出机时,由于对于不定形的粉碎品,咬合良好、能定量地挤出,且与交联剂可均匀混炼,所以挤出量稳定可连续地制造优质的PET发泡体。
进而,在本发明中,只要使用通过15mm的冲孔的粉碎品,就可使进料更好,且与交联剂的混炼的均质性更好。
另外,本发明可以通过将制造了的发泡片继续加热,或一次卷成辊暂时放置后开卷,作成发泡片,将其加热的方法,将发泡片进行软化,通过成形模具进行成形,接着,进行切断,分成成形体和其余部分,将其余部分作成粉碎回收品,送入挤出机,所以可将成形体以外的部分全部回收,作成成形品,是可以连续进行发泡工序及成形工序的有效制造方法。
另外,本发明的制造装置,在可以容易地实施上述的发明方法上,是有用的。
以下,举出实施例,具体地说明本发明的优点。以下,所说“份”是指“重量份”。
〔实施例1〕
本实施例使用图1所示的装置。
将粉碎了的特性粘度0.65、重均分子量Mn53200、发包指数0.38的未结晶状态的压力瓶的回收品100份、滑石1份和碳酸钠0.05份的混合物用滚筒混合后充填到具有螺旋加料器的定量供给器6的料斗中,以33kg/Hr的比例连续地加入到第1段挤出机中。另外,将用滚筒混合了的特性粘度0.81、Mw75000、发泡指数0.639的未结晶状态的新原料聚对苯二甲酸乙二醇酯100份、滑石1份、碳酸钠0.05份及苯均四甲酐1.0份的混合物,充填到具有螺旋加料器的定量供给器7的料斗中,以17kg/Hr的比例,连续地供给到第1段挤出机中。
作为第1段挤出机,使用长2400mm、口径65mmφ咬合型同方向的双轴挤出机。第1段双轴挤出机的螺旋转速保持在60rpm、挤出机缸体温度保持在240℃~285℃。第2段挤出机的螺旋,使用挤出量的计量部分的长度为845mm(L/D=13)、注入发泡剂的附近,埋入216根直径为5mm的销钉。另外,从与第1段挤出机途中的真空泵相连的放气孔,排出挤出机内的水份。此时的真空度为4.5torr。在第1段挤出机中除去水分,进行增粘反应后,将熔融混合物通过保持在275℃的连接管3,供给到口径65mm、L/D25的单轴挤出机4中。
第2段挤出机的螺旋转数保持在60rpm、挤出机的温度保持在265℃~275℃。另外,从第2段挤出机的途中,以0.7份的比例,注入发泡剂(丁烷)。含有发泡剂的熔融混合物从口径80mmφ、缝隙宽0.5mm的园型模具5中挤出到大气中。使挤出的熔融树脂混合物一边发泡一边取出。用直径205mmφ、长740mm的园筒形心轴成形成园筒形,切开其园筒形发泡体的一部分,卷成板状物。此时,在园筒形心轴中循环冷却水,保持表面温度为25℃。
得到的发泡板,密度为0.23g/cc、宽度640mm、厚为1.5mm,具有美丽的外观。该发泡板的Mw为118000。
另外,取样后,一边将挤出机保持在相同条件下运转,一边从第1段挤出机的顶盖部取出熔融树脂,测定取出的树脂的重均分子量的结果,其值为125,000。
〔实施例2〕
本实施例,使用图2的所示的装置。
将特性粘度为0.81、Mw为75000、发泡指数为0.639的未结晶状态的新原料聚对苯二甲酸乙二醇酯充填到具有螺旋加料器的定量供给器6的料斗中,以45kg/Hr的比例,连续地将其供给到第1段挤出机中。另外,将特性粘度是0.78、Mw是70800、发泡指数是0.602混有10重量%滑石的未结晶状态的聚对苯二甲酸乙二醇酯母体物充填到具有螺旋加料器的定量供给器7的料斗中,以5kg/Hr的比例,连续地供给到第1段的挤出机中。另外,将用超级混合器混合了碳酸钠15重量%。和苯均四甲酐85重量%的混合物,充填到刷式微粉体定量供给器8的料斗中,以33g/Hr的比例连续地供给到第1段的挤出机中。
以下,大致使用与实施例1相同的装置,在相同的条件下进行制造。
得到的发泡板的密度为0.23g/cc、宽640mm、厚为1.5mm,具有美丽的外观。
另外,取样后,将挤出机一边保持在相同条件下连续运转,一边从第1段的挤出机顶盖部取出熔融树脂,该树脂的Mw为134000。另外,发泡板的Mw为129000。〔实施例3〕
本实施例,用图3所示的方法进行。
作为双轴挤出机6,使用口径65mm的咬合的双轴挤出机,作为第2个挤出机8,使用口径65mm的单轴挤出机。将塑料瓶的重均分子量(以下称为Mw)约为70000的片及成形后的修整余料的回收品以3∶2重量比组成的粉碎物,从回收品的定量供给装置3′以约45kg/Hr的比例,经过原料投入口4′,连续地供给到双轴挤出机6中。
另外,一边混合Mw约为70000的新原料聚对苯二甲酸乙二醇酯树脂(以下称为Pet)100份和、另外混炼了滑石30重量%的Pet17份、苯均四甲酐2份、碳酸钠0.25份、混练了四氟乙烯树脂粉末〔旭硝子(株)制、フルオン L169J〕10重量%的Pet0.6份,一边从定量供给装置3,以12kg/Hr的比例,经过原料入口4,连续地供给到双轴挤出机6中。
双轴挤出机6的滚筒长度为2400mm,螺旋转速控制在84rpm、挤出机缸体温度控制在240~285°。从设在双轴挤出机6途中的2个排气口5,以4.5Torr的减压度,从挤出机内的熔融树脂减压吸引除去水分等其他挥发分。
在双轴挤出机6内,通过交联剂进行交联,提高PET的熔融粘度,供给到单轴挤出机8中。单轴挤出机8的旋转转速取为39rpm、一边将缸体温度控制在265℃~275℃,一边以0.7份的比例,将发泡剂(正丁烷/异丁烷=6/4)用泵9,从挤出机8的缸体的途中注入,作成发泡性树脂。将该发包性树脂,从口径80mm、缝隙宽0.5mm的园环状喷嘴向大气中挤出。每3分钟测定10次此时的挤出波动,是2.72%。
挤出的发泡性树脂,一边发泡,一边在直径205mm的冷却心轴12上进行,其间,将温度从约200℃降低到65℃,成形成园筒形。用切刀13在园筒状发泡成形的一处切开,扩展成板状,再用牵引辊14作成300m的辊。
得到的发泡体的密度为0.27g/cc、厚度为1.43mm、发包板的挤出方向的拉伸破坏伸长为95.3%、宽方向的拉伸破坏伸长为87.5%、结晶度为7%。
将该发泡板15,在卷辊状态下放置二周时间。然后,将该卷辊的发泡板15装入热粘结装置21中,在此开卷,在发泡板15上贴合非发泡的PET薄膜22,进行叠层。非发泡的PET薄膜22是密度为1.3、厚为0.025mm的无拉伸的薄膜,在与发泡板接触的面上,用耐热性油墨印刷上图案。贴合是通过将发泡板15及非发泡薄膜22通过成对辊23和24及25和26之间进行的。在这些辊中,上辊23加热到155℃、下辊24冷却到30℃、辊25和26中任何一个均冷却到25℃。这样得到的叠层楹,在加热炉16的入口,大约达到60℃。
在加热炉16的上下,配置多个远红外陶瓷加热器。叠层板的必要的面积部分间歇地运向加热炉16中。叠层板的表面在加热炉16内,被加热到145~160℃。
成形装置17是由凸型27及凹型28组成的真空、压缩空气成型器,在各型模中,设有加热器,保持可以调整型模温度。凸型27要作成可供给1kg/cm2的压缩空气,凹型28可进行600mmHg的真空吸引。两型模作成可通过油压装置进行接近或离开。各型模均加热到180℃。
将送到凸型和凹型之间的叠层板,通过来自凹型28的真空作用,进行成形,同时通过来自凸型27的压缩空气作用进行成形。成形挤压时间取作为DSC结晶度达到17~30%的时间的7秒。另外,各型模要调整成可以得到以下尺寸的成形体。
在尺寸125mm×155mm×30mm(深)的浅底容器中,底面壁厚2.0~2.5mm、侧面壁厚为1.30~1.45mm。
这样,将叠层板加热到玻璃化点(约70~75℃)以上、结晶温度(约130℃)以下,进行成形,在保持成形的形状下,加热到结晶温度以上,熔点(约250℃~260℃)以下,接着,在冷却型模(未图示出)进行冷却,送至修整装置18进行修整,得到叠层发泡板制的耐热性容器。同时,通过修整,将发生的碎屑连续地送到粉碎机,在此,作成通过10mm的冲孔的小片,以这样的形状,将其作为回收品,送到安装在挤出机6上部的料斗20中,供再使用。
〔实施例4〕
挤出机6和8,使用与实施例3相同的挤出机,如图4所示地进行实施。
在本实施例中,将在Pet中加入苯均四甲酐0.3重量%,挤出发泡得到的发泡板的碎屑的粉碎物(Mw约为130000),以约14kg/Hr的比例,从回收品定量供给装置3′,通过投入口4′,连续地供给到双轴挤出机6中。
一边混合Mw约75000的新原料Pet100份、混炼了滑石30重量%的Pet3.5份、苯均四甲酐0.3份、碳酸钠0.05份、混炼了四氟乙烯树脂粉未〔旭硝子(株)制,フルオン L169J〕10重量%的Pet树脂0.1份,一边以38kg/Hr的比例,从定量供给装置3,通过原料入口4;连续地供给到双轴挤出机6中。
将双轴挤出机6的螺旋转数控制在79rpm、挤出机缸体的温度控制在0~290℃。从设在双轴挤出机6的2个排气孔口5,以4.5Torr的真空度,从挤出机内的熔融树脂减压吸引除去水分等其他的挥发份。
将双轴挤出机6内交联的熔融PEL,通过以45rpm转速旋转的齿轮泵7流向第2个挤出机8。在第2个挤出机8中,一边将螺旋转数控制在28rpm、将缸体温度控制在265℃~280℃,一边将作为发泡剂的氮气以约0.15份的比例,通过泵9,压入到树脂中,作成发泡性树脂。将该发泡性树脂,从口径95mm、缝隙宽0.5mm的园环状喷嘴孔中,向大气中挤出。
挤出的发泡性板,一边发泡、一边向直径205mm的冷却心轴12上移动,温度从约200℃下降到68℃,成形成园筒形。用切割机13切断其园筒形成形体的一处,扩展成平板状,用牵引辊14牵引得到发泡板。该发泡板的密度为0.36g/cc、挤出方向的拉伸破坏伸长为99.7%、宽方向的拉伸破坏伸长为85.6%、厚度为1.02mm、结晶度为8%。
该PET发泡板,不进行卷取,直接送入加热炉16,进行加热,加热炉16是使用与实施例3相同的。发泡板在加热炉的入口处的温度为57℃。向加热炉16运送;是采取间歇移动的方法。发泡板的表面要加热到145~160℃之间。
接着,将PET发泡板送入成形装置17。成形装置17是使用与实施例3相同的。凸型模27要供给0.9kg/cm2的压缩空气,凹型模28要可进行550mmHg的真空吸引,各型模均加热到180℃。
PET发泡板,通过来自凹型模28的真空作用进行成形的同时,通过来自凸型模27的压缩空气作用7秒钟进行成形,成形成与实施例3相同大小的皿形容器。该容器的壁厚;底面为0.65~0.95mm、侧面是0.45~0.60mm。
将这样的发泡板,与实施例3相同地加热到玻璃化点(约70~75℃)以上、结晶温度(约130℃)以下,进行成形,保持成形形状地加热到结晶温度以上,熔点(约250~260℃)以下,接着,在冷却型模中(未画图示出)进行冷却,送入修整装置18进行修整,得到发泡板制的耐热性容器。同时,将通过修整的碎屑连续地送入粉碎机,在此,作成可通过10mm的冲孔的小片,以这样的形状,将其作为回收品,送到安装在挤出机6上部的料斗20,供再使用。
〔实施例5〕
本实施例使用与实施例3相同的装置进行实施,但只是将PET树脂等的原料及其装置的使用条件等作了若干变更而进行实施。对其变更点进行如下说明。
作为回收品是将PET发泡板进行粉碎得到的粉碎物,重均分子量为约130000的粉碎物,送入图3的回收品用料斗20,在此,以约50kg/Hr的速度将其投入到双轴挤出机6中。
另外,作为新原料,在混练了滑石10重量%的Pet100份中,加入苯均四甲酐3份、碳酸钠0.5份、混练了四氟乙烯树脂粉末10重量%的Pet1.0份,将该混合物,从图3的料斗1中,以5kg/Hr的比例,投入到双轴挤出机6中。
一边将双轴挤出机6的螺旋以80rpm的速度进行旋转,一边将缸体温度控制在230℃~290℃。从设在双轴挤出机6的2个排气口5,以5.0Torr的真空度进行吸引,除去熔融PET中的挥发份。
将这样熔融的PET,通过以44rpm的速度旋转的齿轮泵7,供给到单轴挤出机8中。在单轴挤出机8中,将螺旋的27rpm的速度进行旋转,将缸体温度控制在265℃~285℃,将发泡剂(正丁烷/异丁烷=4/6),通过发泡剂压入泵9,以0.55份的比例,压入到PET中,作成发泡性PET。
将该发泡性PET,从口径80mm宽0.4mm的园环状喷嘴,向大气中挤出。此时每3分钟测定10次挤出波动,其值是2.91%。挤出的PET,一边发泡,一边沿着直径205mm的冷却心轴前进,其间,从约200℃冷却到70℃,成形成园筒状成形体。用切割机13,切断园筒状成形体的一处,扩展成板状,用牵引辊14进行牵引,卷成300m长的辊状。
得到的发泡板的密度为0.35g/cc、挤出方向的拉伸破坏伸长为98.2%、宽方向的拉伸破坏伸长为86.5%,厚为1.00mm,结晶度为7%。
将该PET发泡板放置1个月后,与实施例3相同地,成形成皿形容器。这样得到的容器,底面的厚度为0.97~1.35mm,侧面厚度为0.65~0.88mm。切取该容器后的碎屑,与实施例3相同地,进行粉碎,供再使用。将这样的碎屑,通过循环,可不丢弃PET而完全使用。
〔实施例6〕
本实施例中,使用串联挤出机,作为第1段的挤出机,使用口径65mmφ咬合型同方向旋转的双轴挤出机,作为第2段的挤出机,使用口径65mmφ。L/D为25的单轴挤出机。
将特性粘度0.70、Mw为60000的塑料瓶回收片100份,从具有螺旋加料器的原料定量供给装置,以66kg/Hr的比例,从第1段挤出机的原料投入口连续地供给的第1段挤出机中。另外,将用滚筒混合了特性粘度1.10的未使用的聚对苯二甲酸乙二醇酯树脂100份、滑石3份和377天前开封的苯均四甲酐1.0份的混合物,从具有螺旋加料器的原料定量供给装置,以34kg/Hr的比例,从另一个原料投入口,连续地供给到第1段挤出机中。第1段挤出机的缸体滚筒使用12个长为200mm的滚筒单元连续在一起的结构。将第1段的双轴挤出机的螺旋转速保持在120rpm、将挤出机缸体的温度保持在240℃~285℃。另外,从与第1段挤出机途中的真空泵连接的2个排气孔(开口面积分别为12cm2)除去挤出机中的水份。此时的真空度为4.5torr。
在第1段挤出机中除去水份,进行增粘反应后,通过将熔融混合物保持在275℃的连接管,供给到第2段单轴挤出机中。保持第2段挤出机的螺旋转带为65rpm、将挤出机缸体温度保持在265℃~275℃。另外,从第2段的挤出机的途中,以0.7份的比例,注入发泡剂(丁烷)。含有发泡剂的熔融混合物从口径80mmφ、缝隙宽0.5mm的园盘形模中,向大气中挤出。一边使挤出的熔融树脂混合物发泡,一边用直径330mmφ、长为740mm的园筒形心轴,成形为园筒形。将其园筒形发泡体的一部分切开,作为片状进行卷取。此时,在园筒形心轴上,循环冷却水,将其表面温度保持在25℃。得到的发包板的密度是0.23g/cc、宽为1040mm、厚为1.0mm。
〔实施例7〕
本实施例中,使用与实施例6相同的串联挤出机。
将用滚筒混合了的特性粘度为0.81、Mw为75000的聚对苯二甲酸乙二醇酯树脂100份、滑石1份和碳酸钠0.05份的混合物,从具有螺旋加料器的原料定量供给装置,以30kg/hr的比例,从第1段挤出机原料投入口连续地供给到第1段挤出机中。另外,将用滚筒混合了特性粘度为0.81、Mw为75000的聚对苯二甲酸乙二醇酯100份、滑石1份、碳酸钠0.05份和苯均四酸1.0份的混合物,从具有螺旋加料器的原料定量供给装置,以20kg/Hr的比例,从另一个原料投入口,连续地供给到第1段的挤出机中。将第1段的双轴挤出机的螺旋转数保持在120rpm、挤出机缸体温度保持在240℃~285℃。另外,从与第1段挤出机途中的真空泵相连接的二处排气孔(开口面积分别为12cm2)除去挤出机内的水分。此时的真空度为4.1torr。
在第1段挤出机中,除去水分,进行增粘反应后,将熔融混合物通过保持275℃的连接管,供给到第2段的单轴挤出机中。保持第2段挤出机的螺旋转速为33rpm、挤出机缸体温度为265℃~275℃。另外,从第2段挤出机途中,以1.2份的比例,注入发泡剂(丁烷)。这样,将含有发泡剂的熔融树脂混合物,从以孔径1.2mm,横间距2.8mm、纵间距6.0mm的配置,在1列中设有104个喷咀的3列中设有总计312个喷咀的多咀喷头中,向大气中挤出。挤出的发泡体,马上进入接近模具,并调温到温度60℃的定型模具中(厚18mm×长300mm)。使用此定型模具后,可以得到具有密度为0.15g/cc,宽度300mm、厚度18mm互相紧密相接木纹状外观的聚对苯二甲酸乙二酸脂发泡体。
〔实施例8〕
本实施例中,使用与实施例6相同的串联挤出机。
将用滚筒混合了的特性粘度的0.55、Mw为42300的聚2,6一萘二酸乙二醇酯树脂100份、滑石1份和碳酸钠0.05份的混合物,从具有螺旋加料器的原料定量供给装置,以60kg/Hr的比例,从第1段挤出机的原料入口连续地供给到第1段挤出机。另外,将用滚筒混合了的极限粘度0.55的聚2,6一萘二酸乙二醇脂树脂100份、滑石1份、碳酸钠0.05份和偏苯三酸1.3份的混合物,从具有螺旋加料器的原料定量供给装置,以40kg/Hr的比例,从另一个原料入口,连续地供给到第1段挤出机中。保持第1段的双轴挤出机的螺旋转数为120rpm,挤出机缸体的温度为255℃~290℃。另外,从与第1段挤出机途中与真空泵连接的二处排气孔(开口面积分别为12cm2),除去挤出机内的水份。此时的真空度为4.3torr。
在第1段挤出机中除去水,进行增粘反应后,将熔融混合物,通过保持275℃的连接管,供给到第2段单轴挤出机中。保持第2段挤出机螺旋转带为64rpm,挤出机缸体温度为280℃。另外,从第2段挤出机途中,以0.9份的比例注入发泡剂(丁烷)。含有发包剂的熔融混合物,从口径80mmΦ、缝隙宽0.5mm的园盘形摸具,向大气中挤出。一边使挤出的熔融树脂混合物发泡,一边牵引,用直径为330mmΦ、长为740mm的园筒形心轴,成形成园筒形,切开其园筒形发泡体的一处,作成板状,进行卷取。此时,在园筒形心轴上,循环冷却水,保持其表面温度为25℃。得到的发泡板的密度为0.20g/cc、宽为1040mm、厚为1.0mm。
〔比较例1〕
在本比较例中,除了使用除湿干燥机干燥实施例6所用的PET、在第1段挤出机中不进行真空吸引之外,其他与实施例6完全相同地进行实施。
PET的干燥,是将露点为-50℃的空气、在160℃下,进行循环5小时。
将含有发包剂的熔融混合物从口径80mmΦ、缝隙宽0.5mm的园盘模具中,以100kg/Hr的速率进行挤出,但发泡剂和树脂间断地从模具中放出,得不到发泡板。
〔比较例2〕
在本比较例中,除了在与比较例1相同条件下,予先干燥实施例7所用的PET、在第1段挤出机中不进行真空吸引之外,其他与实施例2完全相同地进行实施。
将含有发泡剂的熔融混合物,以挤出量50kg/Hr的速率进行挤出,但发泡剂和树脂间断地从模具中放出,只得到空隙多、外观差的密度为0.68g/cc的发泡体。该发泡体的Mw为78000。
〔比较例3〕
在本比较例中,除了在与比较例1相同条件下,予先干燥实施例8所用的PET、在第1段挤出机中不进行真空吸引之外,其他与实施例3完全相同地进行实施。
将含有发泡剂的熔融混合物,以挤出量为100kg/Hr的速率挤出,但发泡剂和树脂间断地从模具中放出,不能得到发泡板。
Claims (23)
1,热塑性聚酯系树脂发泡体的制造方法,其中包括熔融混练热塑性聚酯系树脂的熔融混练工序,和对上述熔融树脂进行减压吸引除去该熔融树脂中水分的除去水分工序,和向上述除去水分的熔融树脂中压入发泡剂作成发泡性熔融树脂的发泡剂压入工序,和将发泡性熔融树脂挤出到低压区域进行发泡的挤出发泡工序。
2,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中在上述熔融混练工序中,交联热塑性聚酯系树脂,增加热塑性聚酯系树脂的重均分子量。
3,权利要求2的热塑性聚酯系树脂发泡体的制造方法,其中在将上述发泡性熔融树脂发泡成3倍以上的同时,将该发泡体的重均分子量控制在80000~250000。
4,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中将从上述发泡工序挤出的发泡体作成片、板、厚板的形状。
5,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中上述熔融混练工序和除去水分工序是通过双轴挤出机进行的,上述发泡剂压入工序和上述压出发泡工序是通过单轴挤出机进行的。
6,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中上述除去水分工序是通过减压吸引到20Torr以下进行的。
7,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中的热塑性聚酯系树脂是使用新原料或回收品。
8,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中的热塑性聚酯系树脂是使用新原料和回收品的混合物。
9,权利要求7的热塑性聚酯系树脂发泡体的制造方法,其中的上述回收品是使用发包或非发泡的粉碎品。
10,权利要求5的热塑性聚酯系树脂发泡体的制造方法,其中作为热塑性聚酯系树脂是至少使用回收品的发泡或非发泡的粉碎品。
11,权利要求7的热塑性聚酯系树脂发泡体的制造方法,其中的上述的粉碎品是使用可以通过15mm冲孔大小的物质。
12,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中使用预先用交联剂改质了的热塑性聚酯系树脂。
13,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中在熔融混练工序中进一步混合含氟系树脂。
14,权利要求13的热塑性聚酯系树脂发泡体的制造方法,其中在熔融混练工序中进一步混合聚四氟乙烯树脂。
15,权利要求1的热塑性聚酯系树脂发泡体的制造方法,其中进而包括将由上述挤出发泡工序挤出的发泡体成形为规定形状的成形工序和、
在上述成形工序中将产生的成形余料从上述成形体切除的切除工序和、
在上述切除工序中将切除下的上述成形余料粉碎作成回收品的粉碎回收工序和、
将此回收品返回上述熔融混练工序的回收品返回工序。
16,权利要求15的热塑性聚酯系树脂发泡体的制造方法,其中在上述熔融混练工序中,交联热塑性聚酯系树脂,增加热塑性聚酯系树脂的重均分子量。
17,权利要求15的热塑性聚酯系树脂发泡体的制造方法,其中上述挤出发泡工序和上述成形工序之间包括在上述发泡体上叠层薄膜的叠层工序。
18,权利要求7的热塑性聚酯系树脂发泡体的制造方法,其中上述熔融混练工序中至少包括交联含有回收品的热塑性聚酯系树脂,增加热塑性聚酯系树脂的重均分子量,在上述挤出发泡工序中,在挤出的发泡体上叠层由新原料构成的膜或金属膜。
19,权利要求18的热塑性聚酯系树脂发泡体的制造方法,其中将叠层了上述膜或金属膜的发泡体成形为规定的形状。
20,热塑性聚酯系树脂发泡体成形品,其中通过交联增加重均分子量,至少熔融混练混合了回收品的聚酯系树脂,对该熔融树脂进行减压吸引除去该熔融树脂中的水分后,向熔融树脂中压入发泡剂,将该树脂作成发泡性熔融树脂,将此发泡性熔融树脂挤出到低压区域得到发泡体,在其上面叠层有新原料构成的热塑性树脂薄膜或金属膜,同时将该叠层体成形为规定的形状。
21,热塑性聚酯系树脂发泡体的制造装置,其中包括了在相当滚筒的树脂熔融部的部分具有排气孔的第一挤出机和、
在滚筒的途中具有发泡剂压入口的第二挤出机和、连接第一及第二挤出机的连接管和、
连接第一挤出机排气孔的减压装置和、
安装在上述第二挤出机顶端上的模具。
22,权利要求21的热塑性聚酯系树脂发泡体的制造装置,其中上述第一挤出机是双轴挤出机,上述第二挤出机是单轴挤出机。
23,权利要求21的热塑性聚酯系树脂发泡体的制造装置,其中上述第一挤出机上设置有向该挤出机供给热塑性聚酯系树脂的定量供给器。
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JP06339666A JP3086392B2 (ja) | 1994-12-27 | 1994-12-27 | 熱可塑性ポリエステル系樹脂発泡体の製造方法 |
JP339666/94 | 1994-12-27 | ||
JP7066977A JP3059355B2 (ja) | 1995-02-28 | 1995-02-28 | 熱可塑性ポリエステル系樹脂発泡体の製造方法 |
JP66977/95 | 1995-02-28 | ||
JP07240572A JP3126907B2 (ja) | 1995-08-24 | 1995-08-24 | 熱可塑性ポリエステル系樹脂発泡成形体の製造方法 |
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- 1995-12-26 KR KR1019950056327A patent/KR100363291B1/ko not_active IP Right Cessation
- 1995-12-27 DE DE69529733T patent/DE69529733T2/de not_active Expired - Fee Related
- 1995-12-27 TW TW084113980A patent/TW372242B/zh not_active IP Right Cessation
- 1995-12-27 EP EP20000117347 patent/EP1055499B1/en not_active Expired - Lifetime
- 1995-12-27 DK DK95120581T patent/DK0719626T3/da active
- 1995-12-27 EP EP19950120581 patent/EP0719626B1/en not_active Expired - Lifetime
- 1995-12-27 CN CN95119482A patent/CN1081977C/zh not_active Expired - Fee Related
- 1995-12-27 CA CA 2166170 patent/CA2166170C/en not_active Expired - Fee Related
- 1995-12-27 US US08/579,271 patent/US5958164A/en not_active Expired - Fee Related
- 1995-12-27 DE DE1995633340 patent/DE69533340T2/de not_active Expired - Lifetime
- 1995-12-28 AU AU40764/95A patent/AU697806B2/en not_active Ceased
-
1998
- 1998-10-05 US US09/166,073 patent/US6254977B1/en not_active Expired - Lifetime
-
1999
- 1999-02-22 US US09/253,756 patent/US6537404B1/en not_active Expired - Fee Related
-
2001
- 2001-10-20 CN CN011358106A patent/CN1217780C/zh not_active Expired - Fee Related
-
2003
- 2003-02-04 US US10/357,356 patent/US20030155063A1/en not_active Abandoned
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CN1993410B (zh) * | 2004-07-30 | 2012-05-30 | 株式会社杜威腊 | 发泡板、其制造方法和制造装置 |
CN103764738A (zh) * | 2011-08-29 | 2014-04-30 | 积水化成品工业株式会社 | 模内发泡成型用芳香族聚酯系树脂发泡颗粒及其制造方法、模内发泡成型体、复合结构构件、以及汽车用构件 |
CN102431174A (zh) * | 2011-10-10 | 2012-05-02 | 郭大宝 | 一种食品包装具成型设备 |
CN104057592A (zh) * | 2014-06-25 | 2014-09-24 | 天华化工机械及自动化研究设计院有限公司 | 聚酯型材的加工装置 |
WO2020118987A1 (zh) * | 2018-12-14 | 2020-06-18 | 北京化工大学 | 一种用于热塑性聚酯发泡成型装置 |
CN109435194A (zh) * | 2018-12-14 | 2019-03-08 | 北京化工大学 | 一种用于热塑性聚酯发泡成型装置 |
CN109435194B (zh) * | 2018-12-14 | 2024-03-01 | 北京化工大学 | 一种用于热塑性聚酯发泡成型装置 |
CN111867831A (zh) * | 2018-12-18 | 2020-10-30 | 株式会社Huvis | 加工性优异的复合片及包括其的包装容器的制备方法 |
CN109955452A (zh) * | 2019-01-08 | 2019-07-02 | 郑州大学 | 一种等规聚丙烯挤出发泡装置及工艺 |
CN111319180A (zh) * | 2020-04-20 | 2020-06-23 | 江苏聚核高分子功能材料研究院有限公司 | 回收pet进行连续挤出物理发泡制备板材的工艺 |
CN111319180B (zh) * | 2020-04-20 | 2022-01-04 | 江苏聚核高分子功能材料研究院有限公司 | 回收pet进行连续挤出物理发泡制备板材的工艺 |
CN113667090A (zh) * | 2021-08-04 | 2021-11-19 | 佛山林至高分子材料科技有限公司 | 一种人工软骨仿生吸能材料及其成型工艺 |
CN113942208A (zh) * | 2021-10-25 | 2022-01-18 | 广州海天塑胶有限公司 | 一种采用微发泡注塑工艺制备的汽车车内饰件 |
Also Published As
Publication number | Publication date |
---|---|
CA2166170A1 (en) | 1996-06-28 |
US5958164A (en) | 1999-09-28 |
US20030155063A1 (en) | 2003-08-21 |
KR100363291B1 (ko) | 2003-05-09 |
DE69529733D1 (de) | 2003-04-03 |
TW372242B (en) | 1999-10-21 |
CA2166170C (en) | 2002-07-09 |
DE69533340T2 (de) | 2005-06-30 |
EP1055499A1 (en) | 2000-11-29 |
CN1081977C (zh) | 2002-04-03 |
EP0719626B1 (en) | 2003-02-26 |
DE69533340D1 (de) | 2004-09-09 |
EP0719626A3 (en) | 1996-12-11 |
CN1392041A (zh) | 2003-01-22 |
MX9600072A (es) | 1997-07-31 |
EP1055499B1 (en) | 2004-08-04 |
EP0719626A2 (en) | 1996-07-03 |
DE69529733T2 (de) | 2003-10-23 |
US6537404B1 (en) | 2003-03-25 |
AU697806B2 (en) | 1998-10-15 |
CN1217780C (zh) | 2005-09-07 |
AU4076495A (en) | 1996-07-04 |
KR960021467A (ko) | 1996-07-18 |
US6254977B1 (en) | 2001-07-03 |
DK0719626T3 (da) | 2003-06-10 |
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