CN1024351C - 液态氧化改性乙烯类无规共聚物的制备方法 - Google Patents
液态氧化改性乙烯类无规共聚物的制备方法 Download PDFInfo
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- CN1024351C CN1024351C CN88102774A CN88102774A CN1024351C CN 1024351 C CN1024351 C CN 1024351C CN 88102774 A CN88102774 A CN 88102774A CN 88102774 A CN88102774 A CN 88102774A CN 1024351 C CN1024351 C CN 1024351C
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- random copolymer
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- oxidatively modified
- ethylenic random
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Abstract
-80摩尔%乙烯和20-80摩尔%α-烯烃的液态乙烯类无规共聚物的氧化改性的产物,并且(I)其数约分子量(Mn)为200-10000,(II)分子量分布(Mw/Mn)为4以下以及(III)氧含量为0.1-20%(按重量计)、酸值为0.1-50、皂化值为0.1-100。另外它是通过乙烯类无规共聚物与含氧气体在100-250℃的温度下接触制备的。
Description
本发明是关于液态氧化改性乙烯类无规共聚物及其制备方法和用途。更具体地说,是提供一种在润滑油配合剂、涂料用配合剂和树脂用改性剂等用途方面能发挥优良性能的液态氧化改性乙烯无规共聚物及其制备方法和用途。
对于齿轮润滑油、机油、润滑脂、金属加工油和脱模剂等润滑油来说,根据其使用目的配合使用种种添加剂,以提高其性能,而这些添加剂大部分都是极性化合物。为使这些添加剂达到初期的目的,最好的是使这些添加剂溶解于上述那些润滑油基油中。但是,这些添加剂有的对基油的亲和性较低,在这种情况下,常常没被溶解,多数的只在基油中呈单分散状态。近来,润滑油基油正由过去的矿物油被以烯烃聚合物油为代表的合成润滑油所代替的方向迈进,而这些合成润滑油有更明显的上述倾向,而且多半润滑油性能的提高效果不很明显。因此,在润滑油的用途领域,非常需要能提高各种润滑油添加剂在基油中的溶解性的相溶化剂。
此外,在涂料领域中,也在配合适应于各种目的的添加剂,例如,对于填料防沉降剂,防淌剂、低温可挠性付予剂来说,过去一直都是采用超微二氧化硅粉、超微细沉降性碳酸钙、膨润土及有机膨润土类等等。根据使用目的看,任何一种都很难说它能充分地发挥作用。因此,在涂料的用途领域中,人们也一直强烈地希望能生产出上述性能优良的涂料用配合剂。
本发明者们,认识到在以往的润滑油配合剂方面存在的上述问题,并专心地研究了能更好地发挥其性能的配合剂,结果发现具有特定性状的液态氧化改性乙烯类无规共聚物就是这样一种新物质,该液态氧化改性乙烯类无规共聚物就可达到上述目的,从而完成了本发明。
本发明的目的在于,提供一种新物质,即液态氧化改性乙烯类无规共聚物。
本发明的目的还在于,提供液态氧化改性乙烯类无规共聚物的制造方法。
另外,本发明的进一步的目的在于,提供一种由液态氧化改性乙烯类无规共聚物构成的润滑油用配合剂以及一种由该液态氧化改性乙烯类无规共聚物构成的涂料用配合剂。
若按照本发明,就可以作为物质发明提供一种液态氧化改性乙烯类无规共聚物,该液态氧化乙烯无规共聚物的特征在于,它是一种由含量为20~80摩尔%乙烯和含量为20~80摩尔%α-烯烃构成的液态乙烯类无规共聚物的氧化改性产物,以及
(Ⅰ)用气相渗透压法(VPO)测定的数均分子量(
Mn)为200~10000、
(Ⅱ)用凝胶渗透色谱法测定的分子量分布(
Mw/
Mn)为4以下、
(Ⅲ)氧含量为0.1~20%(按重量计)、酸值为0.1~50、其皂化值为0.1~100。
另外,还可提供具有下列特点的液态氧化改性乙烯类无规共聚物的制备方法,即该方法是将乙烯含量为20~80摩尔%和α-烯烃含量为20~80摩尔%、用气相渗透压法(VPO)测定的数均分子量(
Mn)为200~10000、用凝胶渗透色谱法测定的分子量分布(
Mw/
Mn)为4以下的液态乙烯类无规共聚物,在100~250℃的温度下,与含分子状态氧的气体和/或含臭氧的气体接触,使其氧
化达到氧含量为0.1~20%(按重量计)。同时还可以作为用途发明提供一种由该液态氧化改性乙烯类无规共聚物构成的润滑油用配合剂,以及由该液态氧化改性乙烯类无规共聚物构成的涂料用配合剂。
本发明的液态氧化改性乙烯类无规共聚物是由20~80摩尔%、较好为30~70摩尔%、最好为40~60摩尔%的乙烯和20~80摩尔%、较好为30~70摩尔%、最好为40~60摩尔%的α-烯烃构成的液态乙烯类无规共聚物的氧化改性产物。作为构成该液态乙烯类无规共聚物的α-烯烃,可例示如下:丙烯、1-丁烯、1-戊烯、1-己烯、4-甲基-1-戊烯、1-辛烯、1-癸烯、1-十二碳烯、1-十四碳烯、1-十六碳烯、1-十八碳烯、1-二十碳烯等碳原子数为3-20的α-烯烃。
用4气相渗透压法(VPO)测定的本发明的液态氧化改性乙烯类无规共聚物的数均分子量(
Mn)为200~10000、更好的为300~3000、最佳的为500~5000,分子量分布(
Mw/
Mn)在4以下,较好的在3.5以下,最佳的在3以下。该液态氧化改性乙烯类无规共聚物的数均分子量(
Mn)小于200或大于10000时,都会降低该物质作为润滑油用配合剂或涂料用配合剂的性能。另外,该液态氧化改性乙烯类无规共聚物的分子量分布(
Mw/
Mn)大于4时,同样也会降低该物质作为润滑油配合剂和涂料配合剂的性4能。
本发明的液态氧化改性乙烯类无规共聚物的氧含量为0.1~20%,较好为0.5~15%,最好为1~10%(按重量计),酸值为0.1~50;较好为0.2~40,最好为0.5~35,皂化值为0.1~100,无论该液态氧化改性乙烯类无规共聚物的氧含量小于0.1%(按重量计),还是酸值小于0.1,或其皂化值小于0.1时,也都会降低该物质作为润滑油配合剂或涂料配合剂的性能。另外,若该液态氧化改性乙烯类无规共聚物的氧含量大于20%(按重量计),酸值大于50,或其皂化值大于100时,也都同样会降低其作为润滑油配合剂或涂料配合剂的性能。
本发明的液态氧化改性乙烯类无规共聚物,是液态氧化改性乙烯类无规共聚物的分子末端及共聚物链内部的乙烯成份和丙烯成份,无规地被氧化的产物,作为通过氧化所形成的含氧官能基,可例示如下:羧基、羰氧基(酯键)、甲酰基、羰基、羟基等。而且每1000克液态氧化改性乙烯类无规共聚物中羧基含量为0.001~1摩尔,较好的为0.01~0.8摩尔,羰氧基(酯键)的含量为0.001~2摩尔,更好的为0.01~1.5摩尔、甲酰基和羰基的总含(全羰基)的含量范围为0.01~15摩尔,最好为0.05~10摩尔,羟基的含量范围为0.01~15摩尔,最好为0.05~10摩尔。
本发明的液态氧化变性乙烯类无规共聚物是对乙烯含量为20~80摩尔%,较好为30~70摩尔%、最佳为40~60摩尔%和α-烯烃的含量为20~80摩尔%更好为30~70摩尔%、最佳为40~60摩尔%的液态乙烯类无规共聚物进行氧化改性的产物。另外,该液态乙烯类无规共聚物用气相渗透压法(VPO)测定的数均分子量(
Mn)为200~10000,更好的为300~8000,最佳的为500~5000,该分子量分布(
Mw/
Mn)要在4以下,更好的要在3.5以下,最佳的要在3以下。另外,作为构成该液态乙烯类无规共聚物的α-烯烃成份,同样可以用上面所列举的碳原子数为3~20的α-烯烃作为例示。
该液态乙烯类无规共聚物的乙烯成份组成的标准偏差值(δ)通常在3以下,更好的在2以下,最佳的在1以下。如果该液态乙烯类无规共聚物的乙烯成份组成的标准偏差值(δ)大于3的话,对润滑油或涂料等的溶解性都会降低。
另外,用式(Ⅰ)表示的该液态乙烯类无规共聚物的B值,应满足于式(Ⅱ)的范围,即,
B= (PoE)/(2PòPE) (Ⅰ)
1.0≤B≤1.5 (Ⅱ)
(式中:PE表示共聚物中含乙烯成分的摩尔份数、PO表示含α-烯烃成份的摩尔份数、POE表示全二单元链节的α-烯烃·乙烯链节的摩尔份数。上述B值是表示共聚物链中的各种单体成分的分布状态的指标,B值越大,表示嵌段的链节越少,乙烯及α-烯烃的分布是一样的。
该液态乙烯类无规共聚物的理想B值如下所述
共聚物中乙烯的含量在50摩尔%以下的情况是:
1.0+0.2×PE≤B≤1/(1-PE)、更好的一般式为,
1.0+0.3×PE≤B≤1/(1-PE)、最佳情况的一般式为,
1.0+0.4×PE≤B≤1/(1-PE),
共聚物中乙烯含量在50摩尔%以上的情况是:
1.2-0.2×PE≤B≤1/PE,更好的一般式是:
1.3-0.3×PE≤B≤1/PE,最佳的一般式是:
1.4-0.4×PE≤B≤1/PE
只要按照本申请人在特开昭57-123205号公报及特愿昭60-259835号专利申请所提供的方法,再适当地选择聚合条件,就能制造出该液态乙烯类无规共聚物。
本发明的液态氧化改性乙烯类无规共聚物可以借助于将上述的液态乙烯类无规共聚物用含有分子氧和/或臭氧的气体并任选在惰性烃介质中进行氧化而制备。在氧化中作为所使用的含分子状态氧的气体,除可举出氧、空气之外,还可举出用氮、氩和二氧化碳等不活泼气体将氧稀释为适当浓度的混合气体等为例。另外,作为臭氧气体,除有臭氧及臭氧与氧或空气的混合气体之外,还可例示的有将臭氧和/或氧或空气用氮、氩、二氧化碳等非活泼气体稀释成适当浓度的混合气体。其次,作为含臭氧的气体,除可例示出臭氧及臭氧与氧或空气的混合气体之外,还可例示出的有,将臭氧和/或氧或空气用氮、氩、二氧化碳等惰性气体适当稀释的混合气体。
在氧化反应时所使用的惰性碳氢化合物,可例示如下:戊烷、己烷、庚烷、辛烷、癸烷、十二碳烷、煤油、汽油、苯、甲苯、二甲苯等。
该液态乙烯类无规共聚物的氧化,通常是在没有催化剂的情况下实施的。但在有自由基引发剂或氧化催化剂存在的情况下,也可以实施。作为自由基引发剂,可具体例示如下:过氧化苯甲酰、二叔丁基过氧化物、叔丁基过氧化氢、过氧化二异丙苯、2,5-二甲基2,5-双(过氧化苯甲酸酯)己炔-3等有机过氧化物。作为氧化催化剂,可具体例举的有:醋酸钴、氯化锰、铜、氧化镍、二氧化锰、环烷酸钴等无机化合物。
该液态乙烯类无规共聚物氧化反应时的温度为100-250℃,理想的为120~230℃,最佳的为130~200℃。氧化反应所需要的时间为10分钟~20小时,理想的为30分钟~10小时。该氧化反应无论是在常压或加压的压力条件下均可进行。将氧化反应后的混合物通过常规方法处理,就可获得本发明的液态氧化改性乙烯类无规共聚物。
本发明的液态氧化改性乙烯类无规共聚物还可作为润滑油配合剂使用。作为润滑油配合剂时,均可使用矿物油润滑油基油,烯烃类聚合物或共聚物油等烯烃类合成润滑油、硅类合成润滑油、酯类合成润滑油等的任何一种合成润滑油。该液态氧化改性乙烯类无规共聚物对于100份(按重量计)的上述润滑油基油的配合比例,通常是0.5~300份(按重量计),较好为0.8~200份(按重量计)最好1~150重量份。在该润滑油中除可以配合该液态氧化改性乙烯类无规共聚物外,还可以配合众所周知的其他能与润滑油配合的各种添加剂。作为润滑油用添加剂,可以具体地添加矿物油(中性油)、低分子量的α-烯烃聚合物、硅类合成润滑油、酯类合成润滑油、氧化稳定剂、耐特压添加剂、防锈添加剂、消泡剂、防磨损剂等。这些成份的配合比例要在适当的范围内选用。
配合该液态氧化改性乙烯类无规共聚物的润滑油,可用于齿轮润滑油、机油、润滑酯、金属加工油、脱模剂等用途中。
本发明的液态氧化改性乙烯类无规共聚物还可作为涂料配合剂使用。作为可配合本发明的液态氧化改性乙烯类无规共聚物的涂料的具体例子有:例如,作为漆膜形成用树脂成分的醇酸树脂或其改性物质、不饱和聚酯或其改性物质、酚醛树脂、环氧树脂或其改性物质、脲树脂、密胺树脂等氨基树脂、聚氨酯树脂、干性油等缩聚型涂料用树脂;以及丙烯基类树脂、橡胶类涂料用树脂等(加成)聚合型涂料用树脂等。对于涂料中的漆膜形成主要成分为100重量份时,该液态氧化改性乙烯类无规共聚物的配合比例,通常为0.01~20份、较好的为0.1~10份(按重量计),在配合了本发明的液态氧化改性乙烯类无规共聚物的涂料中,还可以配合一定量其他已知的各种添加剂,例如,颜料、溶剂(在溶剂型涂料的情况下),分散剂(在乳液型涂料的情况下),涂平剂和耐气候稳定剂等。
实施例:
以下通过实施例对本发明进行具体地说明。
本发明的液态氧化改性乙烯类无规共聚物及其原料液态乙烯类无规共聚物的组成及物性值的测定方法和评价方法如下所示。
(1)按照碳13核磁共振检索系统(13C-NMR)的测定求出乙烯成分及α-烯烃成分的组成。
(2)数均分子量的测定方法
以二苯基乙二酮和2,6,10,15,19,23-六甲基廿四烷作为已知分子量的标准试样,用气相渗透压法(VPO)在甲苯溶剂中,80℃的条件下按常规方法,测定数均分子量(
Mn)。
(1)使用已知分子量的标准聚苯乙烯(东洋ソタ(株)制、单分散ポリスチレン测定分子量M及其GPC(Gel Permeation Chromatograph)的计数,绘制分子量M与Ve[洗提体积(Elution Volum)]的关系图形校正曲线,使之此时的浓度为0.02ωt%
(2)根据GPC测定方法记取试样的GPC色谱吸附分析结果,按上述(1)的方法,标出聚苯乙烯换算的数均分子量Mn和重均分子量
Mw,再求出
Mw/
Mn值。这时试样的配制条件及GPC的测定条件如下。
试样的配制:
(a)取一定量的试样和使该试样配制成0.1ωt%浓度所需要量的邻-二氯化苯溶剂一起放入三角烧瓶中;
(b)将三角烧瓶置于140℃的温度下加温一小时后,用不锈钢制的过滤器(孔径为0.5μm)进行过滤,将此过滤液进行GPC测定。
GPC测定按以下条件实施:
(a)装置:
Waters社制造的(150C-ALC/GPC)
(b)色谱柱(カラム):
E.I.du pont de Nemours and company制造的(Zorbaメタィプ)
(c)温度:
140℃
(d)流速:
1毫升/分
(4)乙烯成分组成的标准偏差值(δ)
采用混合比不同的丙酮/己烷混合溶剂,按下述条件及方法并使用分液漏斗进行溶剂提取,将液态低分子量的乙烯类共聚物分割成不同组成的三个级份。
分别溶剂提取的实验方法:
将精确称量的40克试样,溶解在300毫升己烷溶剂中,并放入分液漏斗,然后在25℃的条件下,放入500毫升丙酮,(在此,己烷/丙酮的混合溶剂的容量比为3/5)振动后静置时,则分离为两层。将其下层称做级份溶液-1。然后向上层溶液中追加400毫升丙酮,振动后静置时又会分离成两层,将下层称做级份溶液-2,把上层称做级份溶液-3。
通过蒸馏除去各级份溶液中的溶剂,便可得到级份-1、级份-2、级份-3。
按照13C-NMR分析方法求出各级份中的乙烯组成,用各级份的乙烯组成及重量份数,按下式计算出乙烯组成的标准偏差(δ)。乙烯组成的标准偏差值(δ)越大,则表示其组成分布越广。
E=
上式中Ei表示i级份的乙烯组成,Wi表示i级份的重量分数,E表示共聚物的平均乙烯组成。
(5)B值:
该液态低分子量乙烯类共聚物的B值定义如下:
式中PE表示共聚物中乙烯成分的摩尔份数,PO表示α-烯烃成分的摩尔份数,POE表示全二单元链节的α-烯烃·乙烯链节的摩尔份数。B值是表示共聚物中各单体成分分布状态的指标,并且B值可以基于G·J·Rag[Macromolecules 10,773(1977)]、J·C·Randall[Mocromolecules 15,353(1982)、J·Polymer Science、Polymer physics.Ed.,11,275(1973)]K·Kimura[Poigmer,
25,441(1984)]的报告,通过求出上述定义的PE,PO及POE即可计算出来。上述B值越大,嵌段链的链节就越小,还表示出乙烯与α-烯烃的分布是一样的。
通常在测定温度为120℃,测定频率为25.05MHz,光谱带宽度为1500Hz,滤波器宽为1500Hz,脉冲重复时间为4.2秒,脉冲幅度为7微秒(μSec),累计次数为2000-5000次的条件下,测定在直径为10毫米的试样管中,均匀地溶解在1毫升六氯丁二烯中的大约200毫克的共聚物试样的13C-NMR光谱值。然后,通过从测得的试样光谱求得PE、PO及POE来算出B值。
(6)酸值:
按JISK2501-1980中记载的全酸值测定方法进行测定。
(7)皂化值
按JISK0070-1966中记载的皂化值测定方法进行测定。
(8)氧含量
按有机元素分析方法进行测定。
(9)羟基的测定
按照S·SIGGIA著,桑田勉译的《根据官能团的有机定量分析》所记载的乙酰化作用法来进行测定。
(10)羧基含量,羧氧基含量以及全羰基(羰基、甲酰基)含量按下式计算。
(Ⅰ)
羧基含量= (酸值)/(KoH的分子量)
(羧基摩尔/1000克改性共聚物)
(Ⅱ)羰氧基含量= (皂化值-酸值)/(KoH的分子量)
(羰氧基摩尔/1000克改性共聚物)
(Ⅲ)全羰基含量=(全羰基摩尔/1000克改性共聚物)
=( (氧含量×10)/16 )-
[(羧基含量+羰氧基含量)×2+羟基含量]
本发明的液态氧化改性乙烯类无规共聚物除用作上述的润滑油配合剂及涂料配合计外,还可在其他各种用途中使用。例如:用于润滑油的固态添加剂的分散剂,橡胶或树脂的加工助剂,纤维加工助剂,橡胶或树脂的改性剂,增塑剂,油墨添加剂,金属离子补充剂,离子交换剂,农药展粘剂,涂料的可塑性付予剂,涂料用的底漆改良剂以及粘接剂的改良剂等。
实施例1
在装有空气吹入管,废气口和温度计的搅拌机玻璃反应器(操作容量为1.5升)中,装入乙烯组成为49摩尔%,数均分子量(
Mn)为1000、分子量分布(
Mw/
Mn)为1.43、乙烯成分组成的标准偏差(δ)为0.1,B值为1.2、粘度(20℃)为1040CP的液态乙烯-丙烯无规共聚物800克,一边以1000转/分的转速进行搅拌,一边升温到200℃,然后,将干燥空气以100升/小时的速度通入空气吹入管,吹入时间为6小时。其后停止空气吹入,换由氮气吹入口一边吹入氮气,一边冷却至室温,即制得氧化改性共聚物。所制得的氧化改性共聚物,是具有下面所示物理性质的黄色透明液体。数均分子量(
Mn)为940,分子量分布(
Mw/
Mn)为1.52,酸值为3.7毫克KOH/克,皂化值为5.40毫克KOH/克,氧含量为2.94%(按重量计),粘度(20℃)为1640CP,羧基含量为0.066摩尔/1000克改性共聚物,羰氧基含量为0.030摩尔/1000克改性共聚物,羟基含量为0.60摩尔/1000克改性共聚物,全羰基含量为1.50摩尔/1000克改性共聚物。
实施例2
除采用乙烯组成为49摩尔%,数均分子量(
Mn)为1240,分子量分布(
Mw/
Mn)为1.74,乙烯成分组成标准偏差(δ)为0.1,B值为1.2,粘度(20℃)为4670CP的液态乙烯-丙烯无规共聚物作原料,反应温度为130℃,空气吹入时间为10小时之外,其他操作均与实施例1同样地进行。所获得的氧化改性共聚物是具有下面所示特性的黄色透明体。其数均分子量(
Mn)为1130,分子量分布(
Mw/
Mn)为1.64,酸值为15.3毫克KOH/克,皂化值为25.1毫克KOH/克,氧含量为5.97%(按重量计),粘度(20℃)为12400CP,羧基含量为0.27摩尔/1000克改性共聚物,羰氧基含量为0.17摩尔/1000克改性
共聚物,羟基含量为0.62摩尔/1000克改性共聚物,全羰基含量为2.23摩尔/1000克改性共聚物。
评价例1
按下述方法,对本发明的氧化改性乙烯类无规共聚物作为润滑油用配合剂的性能进行了评价。
(1)试料的调制
取聚α-烯烃低聚物-A(Mobil Chemical社制的MobilSHF-1001)65重量份和聚α-烯烃低聚物B(Chevron Cemical社制的Synfluid GostpAO)35重量份,在300毫升的烧杯内用玻璃棒充分混合后,加入市售的齿轮润滑油组合型添加剂(Texaco社制、TC9535;S24.1%、P1.8%)1重量份以及由实施例1所获得的氧化改性共聚物2重量份、进一步搅拌,调制成评价用的润滑油试样(Ⅰ)。用同样的方法,不加氧化改性共聚物进行调制,制得评价对比用的润滑油试样(Ⅱ)。
(2)评价方法
(Ⅰ)相溶性
取100毫升试样,放入直径为40毫米的玻璃容器中,静置一夜后,用分光光度计,测定了波长为660nm的光吸收率。[吸收池(ヒル):玻璃制,长50毫米(硝子50mm);参比物(对称):己烷]检查透明性。
《评价》
消光率 0.05 0.05~ 0.15~ 0.25~ 0.35
以下 0.15 0.25 0.35 以上
评级 5 4 3 2 1
(Ⅱ)加热稳定性
将装有相溶性试验后的试样的玻璃容器,置于80℃的恒温槽中,放置一个月后取出,在室温下冷却一夜,用与上述(1)同样的方法评价透明性。
(Ⅲ)抗乳化性
按JIS K 2520的方法检查乳化层的消失时间。
《评价》
乳化层消失时间(分) 10 10~ 30~ 60~ 480
以下 30 60 480 以上
评级 5 4 3 2 1
(3)评价结果
表1
试样名称 润滑油试样 润滑油试样
评价项目 (Ⅰ) (Ⅱ)
相溶性 5 2
加热稳定性 4 1
抗乳化性 5 5
评价例2
按下述方法,对本发明的氧化改性乙烯类无规共聚物作为涂料用配合剂的性能进行评价。
(1)试样的调制
将环氧树脂A(三井石油化学工业(株)社制、ェポミッタR-140)85重量份和环氧树脂(同上、ェポミツクR-094)15重量份以及按实施例2所获得的氧化改性共聚物3重量份,充分混合后,再在其中加入硅石粉(竜森工业社制、クリスタラィトA-1)35重量份,再充分搅拌,获得为评价而使用的环氧涂料(Ⅰ)。再以同样的方法,用市售的植物油聚合物类沉降防止剂取代氧化改性共聚物,制得为评价对比用的环氧涂料(Ⅱ)。
(2)评价方法
(Ⅰ)颜料沉降率
在内径18mm,高45mm的带盖玻璃容器内,装入试样,并使试样的装入高度为40mm,静止放置一个月后,按下式求出颜料沉降率。
颜料沉降率(%)= (L)/(Lo) ×100
式中,Lo:颜料的填充高度(40mm)
L:静止放置1个月后,颜料沉降后出现的上部澄清层的高度(mm)。
(Ⅱ)流挂性
对100重量份的评价用涂料,加入28重量份的改性聚胺类固化剂(三井石油化学工业(株)社制、エポミックQ-636),并进行充分地混合后涂敷在玻璃板上,然后将其垂直固定静置固化。在观察流挂情况的同时,求出不发生流挂现象的最高涂敷厚度。
(Ⅲ)评价结果
(表2见文后)
本发明的液态氧化改性乙烯类无规共聚物作为
润滑油用配合剂,涂料用配合剂及树脂用改良剂,都具有优良的效果。
下面对附图作一简要说明
图1为实施例1的液态氧化改性乙烯类无规共聚物的红外线吸收光谱图。
图2为实施例2的液态氧化改性乙烯类无规共聚物的红外线吸收光谱图。
表2
试样名称 环氧涂料 环氧涂料
评价项目 (Ⅰ) (Ⅱ)
颜料沉降率 0 60
(%)
流挂性
最高涂敷厚度(μ) 120 75以下
Claims (3)
1、一种液态氧化改性乙烯类无规共聚物的制备方法,所述方法包括:
让含20~80摩尔%乙烯和80~20摩尔%α-烯烃的液态乙烯类无规共聚物在100~250℃的温度下,与含分子氧、臭氧或其混合物的气体接触,以氧化该共聚物,
其中,制得的液态氧化改性乙烯类无规共聚物具有以下的特性;
(1)用气相渗透压法(VPO)测定的数均分子量(
Mn)为200~10000,
(2)用凝胶渗透色谱法测定的分子量分布(
Mw/
Mn)4以下,
(3)氧含量为0.1~20重量%、酸值为0.1~50、皂化值为0.1~100。
2、根据权利要求1所述的方法,其中所述氧化温度是在130至200℃范围。
3、根据权利要求1所述的方法,其中,作为起始原料的所述液态乙烯类无规共聚物具有用气相渗透压法(VPO)测定的数均分子量(
Mn)为200~10000、用凝胶渗透色谱法测定的分子量分布(
Mw/
Mn)为4以下。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62070216A JPH0778096B2 (ja) | 1987-03-26 | 1987-03-26 | 液状酸化変性エチレン系ランダム共重合体、その製法およびその用途 |
JP70216/87 | 1987-03-26 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN93104658A Division CN1025436C (zh) | 1987-03-26 | 1993-04-20 | 液态氧化改性乙烯类无规共聚物的用途 |
CN93120781A Division CN1044714C (zh) | 1993-12-06 | 1993-12-06 | 含有由液态氧化改性乙烯类无规共聚物构成的配合剂的涂料 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN88102774A CN88102774A (zh) | 1988-11-02 |
CN1024351C true CN1024351C (zh) | 1994-04-27 |
Family
ID=13425118
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN88102774A Expired - Lifetime CN1024351C (zh) | 1987-03-26 | 1988-03-26 | 液态氧化改性乙烯类无规共聚物的制备方法 |
CN93104658A Expired - Lifetime CN1025436C (zh) | 1987-03-26 | 1993-04-20 | 液态氧化改性乙烯类无规共聚物的用途 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN93104658A Expired - Lifetime CN1025436C (zh) | 1987-03-26 | 1993-04-20 | 液态氧化改性乙烯类无规共聚物的用途 |
Country Status (9)
Country | Link |
---|---|
US (1) | US4943658A (zh) |
EP (1) | EP0284425B1 (zh) |
JP (1) | JPH0778096B2 (zh) |
KR (1) | KR910005669B1 (zh) |
CN (2) | CN1024351C (zh) |
CA (1) | CA1307539C (zh) |
DE (1) | DE3862788D1 (zh) |
MY (1) | MY103249A (zh) |
SG (1) | SG4892G (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4981605A (en) * | 1987-06-08 | 1991-01-01 | Mitsui Petrochemical Industries, Ltd. | Liquid modified ethylenic random copolymer and its uses |
US5554310A (en) | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
IL107927A0 (en) | 1992-12-17 | 1994-04-12 | Exxon Chemical Patents Inc | Oil soluble ethylene/1-butene copolymers and lubricating oils containing the same |
DE69834305T2 (de) * | 1997-06-19 | 2007-02-01 | Mitsui Chemicals, Inc. | Harz-formmasse |
WO2004060933A1 (ja) * | 2002-12-27 | 2004-07-22 | Nof Corporation | 水酸基変性エチレン−α−オレフィン系共重合体の製造方法 |
CN111154538A (zh) * | 2018-11-08 | 2020-05-15 | 晟通科技集团有限公司 | 基于工业废油的水性脱模剂 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2970164A (en) * | 1956-09-07 | 1961-01-31 | Sun Oil Co | Preparation of esters by partial oxidation of petroleum fractions |
NL288516A (zh) * | 1962-02-06 | |||
US3692877A (en) * | 1969-12-25 | 1972-09-19 | Sanyo Chemical Ind Ltd | Emulsifiable oxidized polyolefins |
US4323703A (en) * | 1971-02-04 | 1982-04-06 | Standard Oil Company | Process for the oxidation of olefins to aldehydes and acids |
-
1987
- 1987-03-26 JP JP62070216A patent/JPH0778096B2/ja not_active Expired - Lifetime
-
1988
- 1988-03-25 EP EP88302691A patent/EP0284425B1/en not_active Expired - Lifetime
- 1988-03-25 DE DE8888302691T patent/DE3862788D1/de not_active Expired - Lifetime
- 1988-03-25 MY MYPI88000308A patent/MY103249A/en unknown
- 1988-03-25 CA CA000562477A patent/CA1307539C/en not_active Expired - Fee Related
- 1988-03-26 KR KR1019880003308A patent/KR910005669B1/ko not_active IP Right Cessation
- 1988-03-26 CN CN88102774A patent/CN1024351C/zh not_active Expired - Lifetime
- 1988-03-28 US US07/173,102 patent/US4943658A/en not_active Expired - Lifetime
-
1992
- 1992-01-20 SG SG48/92A patent/SG4892G/en unknown
-
1993
- 1993-04-20 CN CN93104658A patent/CN1025436C/zh not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE3862788D1 (de) | 1991-06-20 |
CN1025436C (zh) | 1994-07-13 |
CN1076474A (zh) | 1993-09-22 |
MY103249A (en) | 1993-05-29 |
CA1307539C (en) | 1992-09-15 |
EP0284425A2 (en) | 1988-09-28 |
EP0284425B1 (en) | 1991-05-15 |
SG4892G (en) | 1992-03-20 |
KR910005669B1 (ko) | 1991-08-01 |
EP0284425A3 (en) | 1989-03-15 |
US4943658A (en) | 1990-07-24 |
CN88102774A (zh) | 1988-11-02 |
JPS63238106A (ja) | 1988-10-04 |
JPH0778096B2 (ja) | 1995-08-23 |
KR880011215A (ko) | 1988-10-27 |
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Free format text: CORRECT: CO-PATENTEE; FROM: MITSUI SEKIYU K.K.K. TO: MITSUI CHEMICALS, INC. |
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C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
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