KR910005772B1 - Polyimide siloxan and preparation for the poly imidesiloxan - Google Patents

Polyimide siloxan and preparation for the poly imidesiloxan Download PDF

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KR910005772B1
KR910005772B1 KR1019880003066A KR880003066A KR910005772B1 KR 910005772 B1 KR910005772 B1 KR 910005772B1 KR 1019880003066 A KR1019880003066 A KR 1019880003066A KR 880003066 A KR880003066 A KR 880003066A KR 910005772 B1 KR910005772 B1 KR 910005772B1
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bismaleimide
carbon atoms
polysiloxane
alkylene
general formula
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KR890014630A (en
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박정옥
김명중
송주옥
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주식회사 럭키
허신구
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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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences

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Abstract

The polysilozan of formula (I) is prepd. by michael addition-reaction of the bismaleimide of formula (II) and the polysiloxane of formula (III) at 110-150 deg.C. In the formulas, R1, R2, R3 and R5 are each methyl, ethyl, proplyor phenyl; R4 is opt. alkyl substd. C1-8 alkylene contg. secondary amine at the termination position; n and m are polymn. deg., and n+m is 30-400; A is divalent gp. contg. C1-20.

Description

이미드기를 함유하는 폴리실록산 및 그의 제조방법Polysiloxane containing an imide group and its manufacturing method

본 발명은 하기 일반식(I)의 이미드기를 함유하는 폴리실록산 및 이의 제조방법에 관한 것이다. 더 상세히는, 하기 일반식(II)의 비스말레이미드와 일반식(III)의 폴리실록산을 반응시켜 얻어지는 일반식(I)의 폴리실록산 및 그의 제조방법에 관한 것이다.The present invention relates to a polysiloxane containing an imide group of the following general formula (I) and a method for producing the same. More specifically, the present invention relates to a polysiloxane of the general formula (I) obtained by reacting the bismaleimide of the general formula (II) with the polysiloxane of the general formula (III), and a method for producing the same.

Figure kpo00001
Figure kpo00001

상기 식에서, R1, R2, R3및 R5는 서로 같거나 다른 것으로서, 메틸, 에틸, 프로필 또는 페닐기를 나타내며, R4는 탄소수 1-8개의 알킬렌 또는 알킬이 치환된 탄소수 1-8개의 알킬렌으로서, 알킬렌 말단에 2차 아민기를 갖는 것을 나타내며, R4'는 R4의 1차 아민이며, n과 m은 중합도로서 n과 m의 합이 30-400의 값을 갖는 것을 나타내며, A는 최소 2개 이상, 바람직하기로는 2-20개의 탄소수를 갖는 다이벌런트(divalent)그룹을 나타내며, B는 탄소-탄소 사이에 이중결합을 갖는 것으로서, 탄소수 2개 이상, 바람직하기로는 2-6개의 탄소원자를 포함하는 다이벌런트 그룹을 나타낸다.Wherein R 1 , R 2 , R 3 and R 5 are the same as or different from each other, and represent a methyl, ethyl, propyl or phenyl group, and R 4 is 1-8 alkylene or alkyl substituted with 1 to 8 carbon atoms. Alkylenes, which have a secondary amine group at the alkylene terminus, R 4 ′ is the primary amine of R 4 , n and m represent the degree of polymerization and the sum of n and m has a value of 30-400. , A represents a divalent group having at least 2, preferably 2-20 carbon atoms, B has a double bond between carbon-carbon, 2 or more carbon atoms, preferably 2 -Represents a divergent group containing 6 carbon atoms.

실록산 화합물로 개조한 플라스틱은 많이 알려져 있다. 히드록시 말단기를 포함하는 폴리실록산은 합성수지를 개조하는 목적으로 이미 사용되어 왔으며, 영국특허 제880,022호에서는 폴리옥시알킬렌과 말단에 2개의 알콕시기를 갖는 폴리실록산을 반응시켜 폴리옥시알킬렌-폴리실록산디올블록 공중합체를 만드는 방법을 개시하고 있다.Plastics that have been converted to siloxane compounds are well known. Polysiloxanes containing hydroxy end groups have already been used for the purpose of modifying synthetic resins, and in British Patent No. 880,022, polyoxyalkylene-polysiloxanediol blocks by reacting polyoxyalkylene with polysiloxane having two alkoxy groups at the terminal A method of making a copolymer is disclosed.

또한, 미합중국특허 제3,981,898호는 히드록시기가 있는 폴리실록산과 폴리올(polyols), 디올(diols)을 함께 반응시켜 히드록시기를 함유하는 새로운 폴리실록산을 만드는 방법을 제시하고 있다.In addition, U. S. Patent No. 3,981, 898 discloses a method of making a new polysiloxane containing a hydroxyl group by reacting a polysiloxane having a hydroxyl group with polyols and diols.

그러나, 이들 폴리실록산을 불포화 폴리에스테르(Unsaturated polyester)나 에폭시수지등의 열경화성 수지의 개질제로 사용하게 되면, 성형과정에서 플래쉬(Flash)가 과다하게 발생하는 단점이 있다. 또한, 독일연방공화국 특허 제1,618,836호에서는 Si원자에 직접 결합된 히드록시기가 있는 트리실록산올(trisiloxanol)을 유기수지의 개질제로 사용할 것을 제안하였지만, 이들 실록산올은 유기수지와의 공정과정이 어렵다는 단점 때문에 개질제로는 적당하지 못했다.However, when these polysiloxanes are used as a modifier of a thermosetting resin such as unsaturated polyester or epoxy resin, there is a disadvantage in that excessive flash occurs in the molding process. In addition, the Federal Republic of Germany Patent No. 1,618,836 proposed to use trisiloxanol having a hydroxyl group bonded directly to the Si atom as a modifier of the organic resin, but these siloxaneols are difficult to process with the organic resin. It was not suitable as a modifier.

본 발명자는 상기의 결점을 해결하기 위해 광범위하게 연구, 검토한 결과, 이미드기를 함유하는 폴리실록산을 개발하여, 이를 유기수지, 특히 에폭시수지나 불포화 폴리에스테르와 같은 열경화성 수지의 개질제로 사용한 결과 상기의 문제점을 해소할 수 있음을 발견하고 본 발명을 완성하게 되었다.MEANS TO SOLVE THE PROBLEM As a result of extensive research and examination in order to solve the said fault, it developed the polysiloxane containing imide group, and used it as a modifier of thermosetting resins, such as an organic resin, especially an epoxy resin or unsaturated polyester, It has been found that the problem can be solved and the present invention has been completed.

즉, 본 발명의 폴리실록산을 사용할 경우, 기계적 강도 및 제반특징을 유지하면서도 성형시, 플래쉬의 길이가 현저하게 짧아지고 또한 유기수지와 상용성이 높은 잇점이 있다.That is, when the polysiloxane of the present invention is used, the length of the flash is considerably shortened during molding, while maintaining mechanical strength and general characteristics, and high compatibility with organic resins.

본 발명의 제1목적은 상기 일반식(I)의 이미드가 치환된 폴리실록산을 제공하는 것이다.It is a first object of the present invention to provide a polysiloxane substituted with the imide of formula (I).

본 발명의 제2목적은 상기 일반식(III)의 폴리실록산을 일반식(II)의 비스말레이미드와 100-150℃의 온도에서 마이클부가 반응시켜 일반식(I)의 이미드가 치환된 폴리실록산을 제조하는 방법을 제공하는 것이다.The second object of the present invention is to prepare a polysiloxane in which the imide of general formula (I) is substituted by reacting the polysiloxane of general formula (III) with bismaleimide of general formula (II) at a temperature of 100-150 ° C. To provide a way.

이하 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

본 발명에서 사용되는 일반식(II)의 비스말레이미드로서는 N,N'-1,3-페닐렌 비스말레이미드, N,N'-4,4'-디페닐메탄 비스말레이미드, N,N'-4,4'-디페닐에테르 비스말레이미드, N,N'-4,4'-디시클로헥실메탄 비스말레이미드, N,N'-4,4'-디메틸 시클로헥산 비스말레이미드, N,N'-4,4'-디페닐설폰 비스말레이미드, N,N'-3,4'-디페닐설폰 비스말레이드, N,N'-4,4'-디페닐 시클로헥산 비스말레이미드, N,N'-1,3-크실리렌 비스말레이미드, 2,4-비스말레이미드 톨루엔, 2,6-비스말레이미드 톨루엔등을 들 수 있으며, 이의 사용량은 3-10중량부, 바람직하게는 4-7중량부이다.As bismaleimide of general formula (II) used by this invention, N, N'-1,3-phenylene bismaleimide, N, N'-4,4'- diphenylmethane bismaleimide, N, N '-4,4'-diphenylether bismaleimide, N, N'-4,4'-dicyclohexylmethane bismaleimide, N, N'-4,4'-dimethyl cyclohexane bismaleimide, N , N'-4,4'-diphenylsulfone bismaleimide, N, N'-3,4'-diphenylsulfone bismaleide, N, N'-4,4'-diphenyl cyclohexane bismaleimide , N, N'-1,3-xylene bismaleimide, 2,4-bismaleimide toluene, 2,6-bismaleimide toluene, and the like, and the amount thereof is 3-10 parts by weight, preferably Preferably 4-7 parts by weight.

본 발명에서 사용되는 구조식(III)의 폴리실록산의 예로서는 폴리디메틸실리콘, 폴리메틸페닐실리콘, 폴리에폭시변성실리콘, 폴리디메틸디페닐 공중합실리콘, 폴리지방산 변성실리콘, 실리콘 폴리에테르 공중합체등을 들 수 있으며, 이의 사용량은 30-100중량부, 바람직하게는 40-60중량부이다. 이하 실시예로서 본 발명을 더 상세히 설명한다. 그러나 본 발명이 이들 실시예에 한정되는 것은 아니다.Examples of the polysiloxane of formula (III) used in the present invention include polydimethylsilicone, polymethylphenylsilicone, polyepoxy modified silicone, polydimethyldiphenyl copolymerized silicone, polyfatty acid modified silicone, silicone polyether copolymer, and the like. The amount used is 30-100 parts by weight, preferably 40-60 parts by weight. The present invention is explained in more detail by the following examples. However, the present invention is not limited to these examples.

[실시예 1]Example 1

교반기와 온도계가 부착된 100ml 3구 플라스크에 반응성 폴리디메틸디페닐 공중합 실리콘 45g과 N,N'-4,4'-디페닐메탄 비스말레이미드 5g을 넣고 140℃에서 약 10분간 가열하면서 교반기로 계속 교반한다. 이어서 반응을 확인한 후, 겔 상태의 반응물을 상온으로 냉각시켜 최종생성물을 얻는다.45 g of reactive polydimethyldiphenyl copolymerized silicone and 5 g of N, N'-4,4'-diphenylmethane bismaleimide were added to a 100 ml three-necked flask equipped with a stirrer and a thermometer, and heated at 140 ° C. for about 10 minutes to continue with a stirrer. Stir. Then, after confirming the reaction, the gelled reactant is cooled to room temperature to obtain a final product.

원소분석 : N; 1.8%, C; 32.5%, H; 8.1%Elemental Analysis: N; 1.8%, C; 32.5%, H; 8.1%

IR(cm-1)-NH2; ν=3600, -NH; ν=3720, -C-N; ν=1330IR (cm-1) -NH 2 ; ν = 3600, -NH; ν = 3720, -CN; ν = 1330

NMR(ppm) -N-H; δ=0.7NMR (ppm) -N-H; δ = 0.7

[실시예 2]Example 2

교반기와 온도계가 부착된 100ml 3구 플라스크에 실시예 1의 공중합 실리콘 50g과 N,N'-4,4'-디페닐에테르 비스말레이미드를 5g넣고, 140℃에서 약 10분간 가열하면서 교반기로 계속 교반한다. 반응을 확인한 후, 겔 상태의 반응물을 상온으로 냉각시켜 최종생성물을 얻는다.50 g of the copolymerized silicone of Example 1 and 5 g of N, N'-4,4'-diphenylether bismaleimide were added to a 100 ml three-necked flask equipped with a stirrer and a thermometer, followed by heating at 140 ° C. for about 10 minutes. Stir. After confirming the reaction, the reaction product in the gel state is cooled to room temperature to obtain the final product.

원소분석 : N; 2.0%, C; 33.11%, H; 7.9%Elemental Analysis: N; 2.0%, C; 33.11%, H; 7.9%

IR(cm-1) -NH2; ν=3590, -NH; ν3730, -C-N; ν=1300IR (cm- 1 ) -NH 2 ; ν = 3590, -NH; ν3730, -CN; ν = 1300

NMR(ppm) -N-H; δ=0.6NMR (ppm) -N-H; δ = 0.6

[사용예 1][Example 1]

온도계와 교반기가 부착된 300ml 3구 플라스크에 실시예 1에서 얻은 반응물 7g과 에폭시 당량이 213인 크레졸 노볼락형 에폭시 수지 93g을 넣고 150-160℃에서 약 30분간 가열하면서 격렬하게 교반하여 혼합물 A를 얻는다. 이 혼합물을 상온으로 냉각시킨 후 80g을 취하여 에폭시 수지의 경화제인 페놀 노볼락형 수지(수산기 당량 306) 40g과 경화촉진제 1.1g, 이형제 3g, 실리카분말 337g을 충분히 교반하여 혼합한다.7 g of the reaction product obtained in Example 1 and 93 g of a cresol novolak type epoxy resin having an epoxy equivalent weight of 213 were added to a 300 ml three-necked flask equipped with a thermometer and a stirrer, followed by vigorous stirring while heating at 150-160 ° C. for about 30 minutes to prepare mixture A. Get After cooling the mixture to room temperature, 80 g of the mixture was mixed with 40 g of a phenol novolak-type resin (hydroxyl equivalent 306), a curing agent of an epoxy resin, 1.1 g of a curing accelerator, 3 g of a release agent, and 337 g of a silica powder.

이 조성물을 압축기, 니이더, 롤과 같은 혼합기를 사용하여 85-95℃에서 용융혼련시킨다. B스테이지화된 조성물을 상온으로 급냉시켜 잘게 분쇄 후 175℃로 예열되어 있는 알루미늄 몰드에 붓고 3분간 경화시킨다.The composition is melt kneaded at 85-95 ° C. using a mixer such as a compressor, kneader, roll. The staged composition was quenched to room temperature, finely pulverized, poured into an aluminum mold preheated to 175 ° C, and cured for 3 minutes.

알루미늄 몰드는 각각 0.005인치, 0.01인치, 0.02인치의 틈새가 있어 몰드가 발생하는 플래쉬의 길이를 측정할 수 있으며 그 결과를 표 1에 나타냈다.The aluminum mold has gaps of 0.005 inches, 0.01 inches, and 0.02 inches, respectively, so that the length of the flash generated by the mold can be measured, and the results are shown in Table 1.

[사용예 2][Example 2]

온도계와 교반기가 부착된 300ml 3구 플라스크에 실시예 2에서 얻은 반응물 5g과 사용예 1의 수지 95g을 넣고 150-160℃에서 약 30분간 가열하면서 격렬하게 교반하여 혼합물 B를 얻는다. 이 혼합물을 상온으로 냉각시켜 80g을 취하고 실시예 1의 기타 첨가제를 같은 중량으로 취하여 배합한다. 다음에 사용예 1과 동일한 과정을 거쳐 동일한 조건에서 성형한 후에 플래쉬의 길이를 측정하고, 이에 대한 결과를 표 1에 나타냈다.In a 300 ml three-necked flask equipped with a thermometer and a stirrer, 5 g of the reaction product obtained in Example 2 and 95 g of the resin of Use Example 1 were added, followed by vigorous stirring at 150-160 ° C. for about 30 minutes to obtain a mixture B. 80 g of the mixture is cooled to room temperature, and the other additives of Example 1 are taken in the same weight and blended. Next, after molding under the same conditions as in Example 1, the length of the flash was measured, and the results are shown in Table 1.

[비교예 1-2]Comparative Example 1-2

온도계와 교반기가 부착된 300ml 3구 플라스크에 실시예 1-2에서 사용한 각각의 폴리실록산 5g씩을 사용예 1에서 사용한 에폭시 수지 각 95g과 혼합하여 150-160℃에서 약 1시간 격렬하게 교반시켜 혼합물 C와 D를 얻는다. 각 혼합물을 상온에서 냉각시켜 80g씩 취해 2종류의 혼합물을 준비한다. 각각의 혼합물에 사용예 1에서 사용한 기타 첨가제를 동일한 중량으로 배합하여 2가지의 비교용 조성물을 얻는다. 다음에 사용예 1과 동일한 과정을 거쳐 동일한 방법으로 몰드시 발생하는 플래쉬의 길이를 측정한다. 이에 대한 결과를 표 1에 나타냈다.In a 300 ml three-necked flask equipped with a thermometer and a stirrer, 5 g of each polysiloxane used in Example 1-2 was mixed with 95 g of each epoxy resin used in Example 1, and vigorously stirred at 150-160 ° C. for about 1 hour to mix mixture C and Get D Each mixture is cooled to room temperature and 80 g of each is prepared to prepare two kinds of mixtures. In each mixture, the other additives used in use example 1 are combined in the same weight to obtain two comparative compositions. Next, the length of the flash generated in the mold is measured in the same manner as in Example 1 below. The results for this are shown in Table 1.

표 1의 각 성분의 표시는 g을 나타내며, 플래쉬의 길이는 mm이다. 사용예 1-2, 비교예 1-2에서 굴곡 강도 및 굴곡탄성율은 다음의 방법을 사용한다.Indication of each component of Table 1 shows g, and the length of flash is mm. Flexural strength and flexural modulus in the use example 1-2 and the comparative example 1-2 use the following method.

굴곡강도 : ASTM D790Flexural Strength: ASTM D790

굴곡탄성율 : ASTM D790Flexural Modulus: ASTM D790

[표 1]TABLE 1

Figure kpo00002
Figure kpo00002

* 0.005 인치 틈새를 가진 몰드를 사용할 때* When using a mold with a 0.005 inch clearance

** 0.01 인치 틈새를 가진 몰드를 사용할 때** When using molds with 0.01 inch clearance

*** 0.02 인치 틈새를 가진 몰드를 사용할 때*** When using a mold with a 0.02 inch clearance

상기의 사용예 및 비교예에 나타난 바와 같이 본 발명의 이미드를 함유하는 폴리실록산을 플라스틱등의 수지에 사용할 때, 플래쉬의 길이가 현저하게 짧게 되며, 또한, 굴곡강도가 향상되어 가공성이 우수함을 알 수 있다. 따라서, 본 발명을 플라스틱, 합성수지의 개질제로서 우수한 폴리실록산을 제공한다.As shown in the above use examples and comparative examples, when the polysiloxane containing the imide of the present invention is used in a resin such as plastic, the flash length is remarkably short, and the flexural strength is improved, indicating that the workability is excellent. Can be. Accordingly, the present invention provides a polysiloxane excellent as a modifier of plastics and synthetic resins.

Claims (4)

다음 일반식(I)로 표시되는 폴리실록산Polysiloxane represented by the following general formula (I)
Figure kpo00003
Figure kpo00003
 상기 식에서, R1, R2, R3, R5는 서로 같거나, 다르며, 각각 메틸, 에틸, 프로필 또는 페닐기를 나타내고, R4는 탄소수 1-8개의 알킬렌이나, 알킬이 치환된 탄소수 1-8개의 알킬렌으로서 알킬렌 말단에 2차 아민기를 가진 것을 나타내며, n와 m은 중합도로서 n과 m의 합이 30-400의 값을 갖는 것을 나타내며, A는 2-20개의 탄소원자를 포함하는 다이벌런트(divalent)그룹을 나타낸다.Wherein R 1 , R 2 , R 3 , and R 5 are the same as or different from each other, and each represents a methyl, ethyl, propyl, or phenyl group, and R 4 is alkylene having 1 to 8 carbon atoms, or alkyl substituted with 1 carbon atom. -8 alkylenes having a secondary amine group at the end of the alkylene, n and m represent the degree of polymerization and the sum of n and m has a value of 30-400, A contains 2-20 carbon atoms Represents a divergent group. 하기 일반식(II)의 비스말레이미드와 하기 일반식(III)의 폴리실록산을 110-150℃의 온도에서 마이클 부가반응시킴을 특징으로 하는 일반식(I)의 폴리실록산의 제조방법.A process for producing polysiloxane of general formula (I), wherein bismaleimide of general formula (II) and polysiloxane of general formula (III) are subjected to Michael addition reaction at a temperature of 110-150 ° C.
Figure kpo00004
Figure kpo00004
 상기 식에서, R1, R2, R3, R5는 서로 같거나 다르며, 각각 메틸, 에틸, 프로필 또는 페닐기를 나타내고, R4는 탄소수 1-8개의 알킬렌이나 탄소수 1-8개의 알킬렌으로서 알킬렌 말단에 2차 아민기를 가진 것이며, R4'은 R4의 1차 아민이며, n과 m은 중합도로서, n과 m의 합이 30-400의 값을 갖는 것을 나타내며, B는 탄소-탄소 사이에 이중결합을 갖는 것으로서, 2-6개의 탄소원자를 포함하는 다이벌런트 그룹을 나타내며, A는 2-20의 탄소원자를 포함하는 다이벌런트 그룹을 나타낸다.Wherein R 1 , R 2 , R 3 and R 5 are the same as or different from each other, and each represent a methyl, ethyl, propyl or phenyl group, and R 4 is alkylene having 1-8 carbon atoms or alkylene having 1-8 carbon atoms. Having a secondary amine at the alkylene end, R 4 ′ is the primary amine of R 4 , n and m are degrees of polymerization, indicating that the sum of n and m has a value of 30-400, B is carbon- As having a double bond between carbons, it represents a divergent group containing 2-6 carbon atoms, and A represents a divergent group containing 2-20 carbon atoms. 제2항에 있어서, 비스말레이미드가 N,N'-1,3-페닐렌 비스말레이미드, N,N'-4,4'-디페닐메탄 비스말레이미드, N,N'-4,4'-디페닐에테르비스말레이미드, N,N'-4,4'-디페닐실폰비스말레이미드, N,N'-3,4'-디페닐설폰비스말레이미드, N,N'-4,4'-디시클로헥실메탄비스말레이트, N,N'-4,4'-디메틸시클로헥산비스말레이트, N,N'-4,4'-디스클로헥실 비스말레이미드, N,N'-1,3-크실리렌 비스말레이미드, 2,4-비스말레이미드 톨로엔, 2,6-비스말레이미드 톨루엔임이 특징인 방법.The bismaleimide of claim 2, wherein the bismaleimide is N, N'-1,3-phenylene bismaleimide, N, N'-4,4'-diphenylmethane bismaleimide, N, N'-4,4 '-Diphenyletherbismaleimide, N, N'-4,4'-diphenylsilfonbismaleimide, N, N'-3,4'-diphenylsulfonbismaleimide, N, N'-4, 4'-dicyclohexylmethanebismaleate, N, N'-4,4'-dimethylcyclohexanebismaleate, N, N'-4,4'-disclohexyl bismaleimide, N, N'- 1,3-xylene bismaleimide, 2,4-bismaleimide toloene, 2,6-bismaleimide toluene. 제2항에 있어서, 폴리실록산이 폴리디메틸실리콘, 폴리메틸페닐실리콘, 폴리에폭시변성실리콘, 폴리디메틸디페닐 공중합실리콘, 폴리지방산변성실리콘, 실리콘 폴리에테르 공중합체임이 특징인 방법.The method of claim 2 wherein the polysiloxane is polydimethylsilicone, polymethylphenylsilicone, polyepoxy modified silicone, polydimethyldiphenyl copolymerized silicone, polyfatty acid modified silicone, silicone polyether copolymer.
KR1019880003066A 1988-03-22 1988-03-22 Polyimide siloxan and preparation for the poly imidesiloxan KR910005772B1 (en)

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Publication number Priority date Publication date Assignee Title
CN110760047A (en) * 2018-07-26 2020-02-07 万华化学集团股份有限公司 Bis-secondary amine containing siloxane group and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110760047A (en) * 2018-07-26 2020-02-07 万华化学集团股份有限公司 Bis-secondary amine containing siloxane group and preparation method and application thereof
CN110760047B (en) * 2018-07-26 2022-04-19 万华化学集团股份有限公司 Bis-secondary amine containing siloxane group and preparation method and application thereof

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